From Transaction to Participation

My guest today is James Rutter, Chief Creative Officer at COOK, the pioneering frozen food company, where he oversees internal and external branding and communications. COOK is a founding UK B Corp, committed to using its business as a force for good in society, and has been ranked in the top 100 Best Companies To Work For every year since 2013. COOK’s award-winning frozen meals and puddings (which are desserts, btw) are made by hand in Kent and Somerset, and sold from 98 of its own shops nationwide, in 950 concessions and through its own home delivery service. 

James joined COOK in 2010 after 15 years as a financial journalist and editor, and he speaks and writes regularly about purpose-driven business and brands. You should really follow him on LinkedIn!

James and I talk about the glory that is a proper Fish Pie, and about citizenship and participation. James’ leadership philosophy for his internal team is grounded in a sense of play and a recognition of community.

He shares some of his favorite insights from Peter Block’s book, "Community: The Structure of Belonging" and the deep value he’s found in working with Jon Alexander on Citizenship and Participation. Jon Alexander is the author of the bestselling book, "Citizens." James references Jon Alexander’s Participation Premium Equation in the opening quote.

There is so much goodness in this episode!

At Minute 27 James shares his community and transformation insights from Peter Block, including the essential idea that a small group, a community, is the fundamental unit of change, especially when that group is grounded in possibility. He also goes to share the impact that Block’s ideas of Inversion have had on him:

As James says, summarizing Block:

“It's not the performer who creates the performance, but the audience… And again, in a conversation sense… it's the listener who creates the conversation whereas we often think it's the speaker who creates the conversation… it's the child who creates the parent, not the parent who creates… this is (not) some kind of answer, but… a thought to play with. What if that's the way it works? How would you approach it differently? If the audience creates the performance, then how are you seeking to bring the audience into it? How are you giving them the power?”

At Minute 42 we discuss the importance of Connection over content: 

“...you've got to seek to build the human bonds first before you seek to do whatever the worky thing is you want to do.”

In essence, we are marinating in Danny Meyer’s ideas of an Employee-First workplace, which is why we talk, at the end of the episode, about how Happy Cooks make Happy Food, referencing an earlier conversation we had. 

And James insisted on talking about my Mom being on the Mike Douglas show with John Lennon, Yoko Ono and Chuck Berry in 1972, hosting a historical cooking segment -  this episode is famous because it’s the first time John and Chuck met and Played together. You can see A Tiny Video Clip of my mom on TV here (most of them seem to get pulled down). At a crucial moment in the cooking segment, my mother, just 22 and not actually my mother yet (or anyone’s!) realized that the studio band was playing chaotic music, and that everyone was in a chaotic space, and she announced that unless we had a calm, peaceful environment, the food would taste chaotic - our intention and our energy would flow into the food. The Host, Mike Douglas, asked the band to play something quieter and more mellow, and John Lennon, assigned to cut cabbage, began reciting the mantra he wanted to suffuse the food:

“Rock n Roll…Rock n Roll…Rock n Roll”

What do YOU want to suffuse your work with?

Links, Quotes, Notes, and Resources

James Rutter on LinkedIn

Fish Pie Recipes!

Peter Block on Community: The Structure of Belonging

Jon Alexander’s book Citizens

Jon’s Agency Equation: A Proposal

Agency = Purpose + Belonging + Power

Agency: the ability to shape the context of one’s life

Purpose: the belief that there is something beyond your immediate self that matters

Belonging: the belief that there is a context to which you matter in turn

Power: practical access to genuine opportunities to shape that context

Exit, Voice, Loyalty: An essential book on people and organizations

Finding flourishing and play at work - inspiration in https://www.punchdrunk.com/work/

Quotes no one said: “Teach Them to Yearn for the Vast and Endless Sea”

Via quote investigator: https://quoteinvestigator.com/2015/08/25/sea/

Minimum Viable Transformation

Matt LeMay on Agile Conversations

Happy Cooks make happy food: On Daniel’s Mom being on the Mike Douglas show with John Lennon, Yoko Ono and Chuck Berry Hosting a cooking segment: Context and History! 

Why this episode is famous - it’s the first time John and Chuck met and Played together.

A Tiny Video Clip of my mom on TV! (most of them seem to get pulled down)

Key Quotes

Min 27 “If we're seeking to…restore community, then people have to come together and have a conversation about what's possible, not be anchored on what the problem is, what the solution it is that needs to be found to the problem, what power needs to be exerted to make things work better, but to be open minded to the possibility of what they can create together. And that ultimately that is where community drives from…the unit of transformation is a small group.”

Min 29 “I think you might like this idea as well from this community book, which is about inversion…inversion in terms of thinking about: It's not the performer who creates the performance, but the audience…And again, in a conversation sense… it's the listener who creates the conversation whereas we often think it's the speaker who creates the conversation. He says it's the child who creates the parent, not the parent who creates. I think there's some really interesting kind of. That's not meant to say this is some kind of answer, but it's just a thought to play with. What if that's the way it works? How would you approach it differently? If the audience creates the performance, then how are you seeking to bring the audience into it? How are you giving them the power?”

Min 42 “I do think that in this kind of “be an overnight success, kind of move on, climb the career ladder, have a million jobs in ten years” type vibe. People overlook the real value of established teams and what teams that work together for a long time can really deliver and achieve. Because that's when you do get really high trust. You do get a sense that people turn up and are much more open, are much more willing to be vulnerable. It's human nature. We're not prepared to risk so much with people we don't know so well. If you want people to come and take the mask off, you've got to seek to build the human bonds first before you seek to do whatever the worky thing is you want to do.”

Min 49 “Genuinely, I think the more time we collectively spend thinking about how we are together within our organizations, our businesses… The more productive we're going to be…fulfilled…the more we're going to feel able to take those masks off and be who we genuinely are together and hopefully help each other into a kind of more flourishing future.”

AI Summary and Key Moments

James Rutter and Daniel Stillman discuss creating a sense of community and enabling creativity throughout an organization, with a focus on giving everyone a voice and establishing trust.  

They also talk about the power of playfulness in leadership and the value of established teams and long-term relationships in achieving high trust and vulnerability. James emphasizes the importance of starting with people and their relationships in organizations to create a great product.

Key Points

James explains the importance of giving everyone a voice and creating a sense of community at a diverse workplace with 1800 employees (3:43)

James and Daniel discuss the importance of human flourishing and how it relates to creating a sense of community and enabling creativity throughout an organization (5:56)

James discusses the challenge of enabling people working in a factory to flourish and how their company provides benefits and opportunities for growth (8:30)

James discusses the importance of individuals seeing their own impact on the world and how their company tries to bring that to life through initiatives like care cards for retail teams (12:48)

James shares a story of a customer who received a care card and how it made him feel seen and recognized, highlighting the impact of creativity at an organizational level. (14:10)

The company runs a program called Raw Talent that trains and employs people who have been in prison, homeless, or dealing with addiction or mental health problems (17:15)

James talks about giving everyone a voice and pushing them out of their comfort zones to create creative tension, and mentions an impactful session they had with immersive theater group Punch Drunk. (32:17)

They discuss the atomic unit of change - conversations - and how they can create alignment within a group, and James talks about his role as Chief Creative Officer in holding space for creative team conversations (37:55)

James suggests that building human connections and establishing trust is key to creating an environment where people feel safe to be themselves and take off their masks. He also emphasizes the value of established teams in achieving high levels of trust and vulnerability. (41:05)

More About James Rutter

James is chief creative officer at COOK, the pioneering frozen food company, overseeing internal and external branding and communications. He joined COOK in 2010 after 15 years as a financial journalist and editor. COOK is a founding UK B Corp, committed to using its business as a force for good in society, and has been ranked in the top 100 Best Companies To Work For every year since 2013. COOK’s award-winning, frozen meals and puddings are made by hand in Kent and Somerset, and sold from 98 of its own shops nationwide, in 950 concessions and through its own home delivery service. James speaks and writes regularly about purpose-driven business and brands.

Full AI-Generated Transcript

Daniel Stillman 00:01

I will now officially welcome you to the conversation factory. James, I actually am really pleased that all of our conversations have led to this next conversation, because I've learned so much from you, not only the joys of fish pie.

James Rutter 00:21

You're going to have to explain that to everybody a bit later.

Daniel Stillman 00:24

Yeah. Yes.

James Rutter 00:25

Recipe in the show notes.

Daniel Stillman 00:26

Is that what you meant to say? Yeah. Well, I'm still waiting for the official recipe.

James Rutter 00:31

I've kind of, like, send you the official recipe.

Daniel Stillman 00:34

I've had to hack it together, but I was trying to make a low carb version, so I use solariac and anyway, let's just start with fish pie, because this is a great example of culture, because I think we talked about this in our last conversation. Many of the recipes for fish pie just sort of assume that I live in Britain because it's a very british dish, and they say, oh, go to your shop and get a fish pie frozen mix, which includes various types of fish, and then bang some peas and carrots and what, and then everything that comes out. Those are all things I knew about. I was like, what kind of fish is in a fish pie? No one could really explain. It took me a lot of research to try and pierce the veil of the cultural chasm separating England and America, which was shocking.

James Rutter 01:23

Yeah. Two nations divided by a common language. And fish pie.

Daniel Stillman 01:26

There you go, fish pie. Exactly. So maybe you can put yourself in context. What on earth does a chief creative officer do and where do you do it and why?

James Rutter 01:39

Gosh, I don't know what a chief creative officer should do, but what I do is an entirely, probably different kettle of fish. Back on fish. So I was thinking about this the other day, actually, because people always ask me and I usually just kind of shrug and I said, yeah, it sounds good, doesn't it? I'll tell you when I know what it means, but I kind of just stretch across a lot of things from the obvious, I guess, brand marketing type of creative stuff that probably springs to mind when people think of chief creative officer type roles and then into kind of strategy. And for cook, a lot of internal kind of comms, a lot of internal culture work.

Daniel Stillman 02:28

Yeah.

James Rutter 02:28

So I try and help other people be more creative in their roles rather than assume the crown of creativity, as it were, hopefully. Anyway, that's what I do. And so I try and kind of nudge, facilitate, as you would like to say, no doubt, and generally encourage people to be more creative in whatever they're doing at cook. That's how I like to think of it. Whether I accomplish that or not is another matter entirely.

Daniel Stillman 02:59

Well, we can have one of your employees on.

James Rutter 03:01

Yeah, exactly.

Daniel Stillman 03:03

How do you determine whether or not, I mean, we were talking a little bit before we started around some of the things you're learning around community and thinking of work as a community and bringing a citizen lens. You're really intentionally trying to craft what I would sort of describe as like this cloud of conversations, rivers and valleys of conversations between everyone that eventually lead them to become more creative but also more connected. How are you thinking about the ways in which you're trying to design the conversation at work differently?

James Rutter 03:43

I think

James Rutter 03:48

the obvious thing is that we try or we seek to just give everybody a voice, and that sounds blindingly obvious, I guess. And yet is often in any larger workplace, and we have 1800 people, which obviously is small by some standards, but very big by others, but across 1800 people working all around the country because we got getting on for 100 shops or 100 small retail outlets. So we got kind of 700 people in that kind of context. We've got another 700 people in a kind of classic blue collar manufacturing context in three different sites, four different sites. And then we've got kind of a central office in a classic office type environment. So seeking to give everybody a voice across that incredibly diverse workplace is actually really difficult. Yeah, I wouldn't say we achieve it all the time. Some of the time I really hope we do. But in terms of conversations and connections and relationships, which is what we use relationships as our kind of catch all for human connection, whereas you would go with conversation. But in terms of relationships, that's what we're seeking to. We're seeking to help everybody feel that they have strong relationships with their colleagues, but also with people in other parts of the business, that they have a voice and that they are therefore part of a community rather than a corporation.

Daniel Stillman 05:33

What's important about that shift you mentioned you're reading Peter Block's book on community. What are you learning in that book that's sort of shifting how you shape community? And why is it important to get to that place where people feel like this is a community and not just work, not just a job? It's not just fish pie.

James Rutter 05:56

Yeah, right. I think a lot of this comes down to a little bit. What do you believe about people and human flourishing? In a way? What's the point of it all? Carl? We're going deep early. Daniel.

Daniel Stillman 06:12

Why? Let's go there.

James Rutter 06:14

Yeah.

Daniel Stillman 06:14

Eudemonia is one of my favorite words. That is the greek term for

Daniel Stillman 06:22

the highest state for a person, right? The tippy top of Maslow's hierarchy. Flourishing.

James Rutter 06:28

Yeah, absolutely. And I think there's that sense in which all any of us can hope for is to achieve flourishing however you want to define it. And therefore, when we come together in a workplace, if that experience, if that collection of people isn't helping us move in whatever small way towards our idea of flourishing, then really what's the point? And so when you think about all a business is, at the end of the day, is a bunch of people coming together to do something collectively that they couldn't do on their own. That's all it is. It's a fiction. Otherwise, it doesn't really exist, other than those people's willingness to come together and do stuff. And so when we're together, when we're in the same room or over a call like this, or we're in a shop or in a kind of kitchen, in our respects, what we do there together has got to feel like it's both worth something to us, individually and collectively, and is somehow helping us progress. Baby steps, it might be towards our idea of flourishing.

Daniel Stillman 07:44

Yeah.

James Rutter 07:45

So that's kind of, I think, where it comes from a little bit is that belief in what we should be striving for as people. And how can we enable that, not just for the people up at the top of the pyramid, but for actually everybody in the organization.

Daniel Stillman 08:02

Yeah. So how does creativity and community look different throughout the organization? How do you approach giving everyone a voice and making everyone feel connected and creative? There's like the coal face, as it were, which is maybe the worst. Absolutely right. And then there's communications. There's the people who are wearing different colored collars, as it were.

James Rutter 08:30

Yeah, right. Absolutely. And I think that's one of the biggest challenges and kind of struggle sometimes I have with our ambition, when you take it down to a root level, that we have people working in what most people will call a factory. We never call it a factory. It is a kitchen. But people would see it and say, that looks like a lot like a factory. And they're working in what you might say is a production line, an assembly line. They're doing a pretty repetitive manual task. How can we possibly say that we're enabling those people to flourish? Is kind of a bad day. Look at that kind of context. And then, if you like a good day, look at that context is okay. We've got these people in a room. They got smiles on their faces. They're talking to their colleagues. They're having a laugh. They're getting paid enough to live on, which is really important. Yes. They get breaks when they get fed, they get some lovely little kind of benefits, which means they can use a free holiday home, because we got a little holiday home that they can go and stay in. They get together with their colleagues and they have some fun, and they actually, every so often, they look up and they feel part of a bigger whole, and they can say that. They can see that that's doing some good in the world. And so they feel a little prick of pride. And so when they go and meet their friends and they talk about their week at work and their friend just kind of moans on about the drudgery, they can say, oh, you know what? But we did this great thing as a business, or that we get free doctor's appointments or whatever it is. We get our birthday off little things, but they feel a little bit of pride about where they work, and they feel that actually they can stay there for a period of time, they can learn, they can grow, they can move on, they can achieve something that perhaps they didn't think was possible a few years ago.

Daniel Stillman 10:42

Yeah.

James Rutter 10:42

And so even at that level, I say even that's a very kind of condescending thing to say, but at that level, we are hopefully bringing the possibility of flourishing to people in a way that another company wouldn't.

Daniel Stillman 10:59

Yeah. Is some of that have to do know? I'm wondering how the narrative of the B Corp is held throughout the company, because you are a benefit corporation, and we can talk a little bit about what that means for those folks who maybe aren't familiar with it. Do the people throughout the organization understand what that means to be part of not just their own flourishing and organizational flourishing, but also societal flourishing, which is presumably part of what a benefit corporation is meant to.

James Rutter 11:42

Know, the B Corp movement. And again, this is a classic transatlantic divide. So whereas in the US, you have benefit corporations, which is a legal structure.

Daniel Stillman 11:57

Yes.

James Rutter 11:58

You then also still have certified B Corps, which is a certification, kind of an independent certification process that is different from being a benefit corporation.

Daniel Stillman 12:11

Right.

James Rutter 12:11

And over here in the UK, we only have certified B Corp, so we don't have a legal structure.

Daniel Stillman 12:17

Right. You're still whatever the equivalent of our S Corp or LLC is to the government, you look the same.

James Rutter 12:23

Yeah, to the government we look the same. We have to change some wording in terms of how we're incorporated, say we actually take people and planet into consideration, not just profit, when making any decision, but we're not in the same legal structure as us benefit corp people. But as a B Corp, certified B Corp, yeah, the whole kind of goal is using business as a force for good in society. Now, how many of our 1800 people know about that, buy into that, get up in the morning feeling good about that? I don't know. Hopefully some. Definitely not all, I would say, but certainly some. And I guess in all this realm, be it B Corp, be it talking about kind of higher purpose of business, however you want to frame it, I do think a lot of it comes down to your role, your job, what you do day to day, and how can you witness your impact on the world. So you're going to get some pride from what the organization does, but to really have a sense that what you are doing is contributing, I think everybody needs to see their own impact.

Daniel Stillman 13:37

Yes.

James Rutter 13:40

Over the years we've tried to bring that to life with people in a number of different ways, I guess. And like I say, it's often much easier if you're like my direct team in the marketing team and you're talking about all this wonderful stuff and posting stuff on social media and what have you. Or like I say, for somebody who's in more of a manufacturing environment, it's tough. For somebody who's on the shop floor in a retail environment, it's more difficult. Two of the things we've done that I think goes some way towards achieving that. For the retail teams,

James Rutter 14:15

every year we give them, if you like, two little cards, and these are called care cards. And care is one of, we have, we have core values, of course we do called essential ingredients, and care is one of those. And each of those cards gives the holder 30% off our food for a year. And they can give that card to whoever they like, who they think needs our food because they may have health problems or their spouse may have health problems, or they may be bereaved or struggling somehow. And it's just for that member of card to see somebody who thinks needs it and say, oh, here you go, have a card, take 30% off. And the story of that really brings us to life that that kind of has the desired effect was a guy just sent us in a letter just to say, I was in one of your shops and I'd rushed in and grabbed some food, got to the till, I said, could I come back and pick it up later? And I said, yeah, of course, because he had to get to the hospital for his wife's chemotherapy treatment because she had cancer and he had two young kids and they were screaming. He was trying to get out the store and said, don't worry. Don't worry at all. So he came back a couple of hours later to pick his food up, and they just presented him with this card. And he said in his little letter, I just had to leave the shop because I was really emotional and I didn't want to cry in public. And he said, it wasn't the fact that it gave me money off, it wasn't the discount. It was the fact that somebody had seen me in my moment of need and recognized that for that kind of shop team member, that is them witnessing their impact.

Daniel Stillman 16:03

Yes.

James Rutter 16:04

And thinking, actually, I'm doing a good.

Daniel Stillman 16:05

Thing in the world and being creative. That's an example of creativity being harnessed at an organizational level. And it's a lovely story. And honestly, I can hear how it hits you because you feel it telling.

James Rutter 16:22

It, and then it gets.

Daniel Stillman 16:25

The hope is that everyone who gets one of these care cards in the organization feels that narrative impact, that they get that story.

James Rutter 16:37

Yeah, absolutely. And again, I don't think maybe this speaks a little bit to the community idea as well. We can't direct people to kind of use the cards in that way. We are giving them the possibility of having that impact and feeling that emotional connection and going home with a warm glow that night. That's almost the most we can do. We can't force it, but we can say, look, here you go, if you want to step into that, and here's your opportunity.

Daniel Stillman 17:10

I mean, they can give it to their mom if they want.

James Rutter 17:12

Yeah, no, they can.

Daniel Stillman 17:13

Genuinely legitimate.

James Rutter 17:15

Yeah, no, they can. So on the shop side, there's that kind of thing. And then, if you like, on the kitchen side of things, we run what is now quite a big, long standing program of taking people who've been spent time in prison or homeless, dealing with addiction or mental health problems. And we have a program called raw talent that then gives them kind of two weeks of, kind of quite intensive training, and then at the end of that, the possibility of a job in the kitchen. And so we've now taken, I think, 150 people over the last seven years. And again, those people then go into work, and the people they work alongside who aren't from the program when it's most successful, they feel genuinely invested in those people's future, and they feel a real sense of responsibility, but also of impact when it works and equally when it doesn't work, they feel absolutely gutted if people leave. And again, the kind of story that brings that to life for me was when we first started doing this program about seven or eight years ago, I think one of the first people we took into the program had been convicted. I think it was either manslaughter or murder. Very long standing case. And we'd said at the start, look, of the first, particularly this is early days, we're not going to take in anybody who you might feel is going to be potentially risky for your team and one of the teams in the kitchen, I think our pastry team was particularly nervous about the program and a bit resistant to letting it happen, but had reluctantly agreed. So we were a bit worried about this guy going. But anyway, he had him. He'd met lots of people in the kitchen, so we thought, well, let's let it keep going. We'll see how it goes. And first day, he kind of turned up. And at their break, at lunch, he kind of went to sit in the canteen and he didn't have anything to eat for lunch. These are date. We feed everybody there. We didn't back then. And one of the women in the pastry team just noticed it. So the next day when he came in for lunch, she just came over and gave him a sandwich and said, I made this for you today, so you can eat it. And again, it's just that sense of human connection, of suddenly feeling like you're responsible for somebody else that you're taking an interest in and that actually you can help them through.

Daniel Stillman 19:51

I think it's lovely. And this is sparking my brain to ask you about the citizens book that you're reading and if what you're learning from that is shaping how you're shaping culture now and in the future.

James Rutter 20:12

This is from the Peter Block one.

Daniel Stillman 20:14

Well, so you mentioned also John Alexander's book Citizen.

James Rutter 20:17

There's two. There's community, peter block, and citizens. So John is a guy, he's a british guy. He speaks our language literally, so he knows what fish pie is. And he's got a little consultancy or a partnership called New Citizenship Project. And they've been going for a while working around this idea that we need to reclaim our sense of citizenship. So move beyond the sense in which we're a consumer and where our only sense of agency in the world is to consume something, to kind of give over our power to the corporations who are pushing stuff at us and say that's all we can do, and to actually reclaim our agency as citizens, to come together, to decide, to create, to kind of, I guess in conversation to your theme, kind of move ourselves forward and get out of this hole we're collectively in. And so a lot of their work, where we've kind of found the amount of value in working with them, is around this idea of participation and how to really resonate with people, with customers, you need to give them an opportunity not just to buy from you, but to buy into you and participate in what you're doing. And they've got a lovely little equation, which they call the participation premium, which is a higher purpose. So as a company, to have a higher purpose plus participation. That's right. I'm trying to remember how this equation works now. Higher purpose.

Daniel Stillman 22:10

I know.

James Rutter 22:11

Higher purpose plus something in return. So it's not to deny that actually, people kind of need to feel they get something from it. Times participation creates huge value. And so where we've been playing with that from a kind of customer facing side of things is, okay, so how can we give customers the opportunity to participate in a way that isn't just buying a product? What more can we do? So is there a conversation we can involve them? Can they somehow help us solve a problem? Can we invite them into a shop to somehow create something with us? I think that side of the citizens idea from a business perspective is really interesting. So how do you open your doors a little bit to participation and enable people to be more than just if you're, like a blind consumer of whatever it is you're doing?

Daniel Stillman 23:07

Yes. So this is really emergent for you. This is like something you're noodling on, how to make this real.

James Rutter 23:16

Yeah, completely. And a lot of it can just revolve around language.

James Rutter 23:27

So we do some kind of healthy kind of pot type of deal, dishes that are kind of for lunch. And so we had a promotion on. You can get three of these pots for ten pounds. So obviously that's one way you can just talk about it, save whatever, get three for ten pounds is a very obviously consumer driven way of talking about it. But you could reframe that language as kind of one for you and two for your friends, get together and eat. And so in a way that is just slightly taking people out of the. I'm just a consumer mentality into something that is more about, well, actually, this is enabling me to do something productive in the world. Does that make sense?

Daniel Stillman 24:17

It does. And it's a reframing. There's, like, this tiny axe in the back of my head that I need to grind because there's this famous quote. One of my favorite websites is this website called quote investigator. And very often people say, like, oh, there's this famous quote from so and so. And I'm like, they never said that. There's so many famous quotes that nobody ever said. And there's this famous quote that people think they attribute to Antoine Song. I can't pronounce his last name anymore. The guy who wrote the little Prince

James Rutter 24:49

The french guy.

Daniel Stillman 24:50

The french guy. And there's this quote that everyone attributes to him. It's like, if you wish to build a ship, do not divide men into teams and send them into the forest to cut wood. Instead, teach them to long for the vast and endless sea. It's a very beautiful quote, but unfortunately he never said it. And it's not really clear that anybody ever said it. But that doesn't mean that the idea isn't true. And even something as simple as, like, I think very often people think money is the lever to pull because it's very obvious and brutish. Lever, right? Like buy three, get one off. Right. I forgot the deal already. See, because it's not that important, it's not that impactful. But when you frame it as community, when you frame it as feeding your friends, when you frame it as gathering people together and potentially harness what comes out of that somehow, like, make people feel like they're sharing those stories that they are absolutely writing society, invite someone you don't agree with to dinner. These are ways of really being part of a very different conversation than we make food and it's affordable and we're making it slightly more affordable for you. And that is a very creative approach to changing the conversation about what it is that you do and what people would say it is that you.

James Rutter 26:21

So to my other book, I'm reading my community Peter block book, which I was saying earlier, he talks about community is a conversation around possibility.

Daniel Stillman 26:31

Can you say that one more time? Let's let that sink in. That's a really great. Community is a conversation around possibility.

James Rutter 26:40

Possibility, yeah.

Daniel Stillman 26:41

What on earth does that mean? Say more about that. That's beautiful.

James Rutter 26:45

I think his point is quite a big kind of mind expanding one. If we're seeking to. He talks about restore community, then people have to come together and have a conversation about what's possible, not be anchored on what the problem is, what the solution it is that needs to be found to the problem, what power needs to be exerted to make things work better, but to be open minded to the possibility of what they can create together. And that ultimately that is where community drives from. Yes, and he's got this again, there's lots of lovely little sentences, long quotes in this book.

James Rutter 27:41

I'm going to misquote this. But anyway. But the unit of transformation is a small group.

Daniel Stillman 27:46

Yeah.

James Rutter 27:48

And that immediately reminded me of that classic Margaret Mead quote. If she really said it, you can check.

Daniel Stillman 27:54

She did say it, but I'll double check.

James Rutter 27:58

Fact checking.

Daniel Stillman 27:59

Margaret Mead.

James Rutter 28:00

Yeah, exactly. That whole never doubt the ability of a small group of people to change. The world is what it ever has. And I think it's actually a really powerful idea around how do you bring together small groups that then can be kind of energized and create real ripples through a business, through society, through a community. And the power of small groups is really interesting.

Daniel Stillman 28:32

I think this is really.

James Rutter 28:34

How do we even get onto that?

Daniel Stillman 28:35

What were we doing? Well, we're talking about community and citizenship. Yeah.

James Rutter 28:39

Because I was going to say, I think you might like this idea as well from this community book, which is about inversion. So inversion in terms of thinking about. It's not the performer who creates the performance, but the audience.

Daniel Stillman 28:58

Yes.

James Rutter 28:59

And again, in a conversation sense. So it's the listener who creates the conversation whereas we often think it's the speaker who creates the conversation. He says it's the child who creates the parent, not the parent who creates. I think there's some really interesting kind of. That's not meant to say this is some kind of answer, but it's just a thought to play with. What if that's the way it works? How would you approach it differently?

Daniel Stillman 29:23

Right.

James Rutter 29:24

If the audience creates the performance, then how are you seeking to bring the audience into it? How are you giving them the power? How are you.

Daniel Stillman 29:32

Well, recognizing that they have the power?

James Rutter 29:35

Yeah.

Daniel Stillman 29:36

I recently had a guest on my friend Matt Lemay. We talked about his one page, 1 hour manifesto, which I will link to in the show notes where he just thinks teams should only any. Nobody should spend more than an hour working on anything longer than one page to share back with the team. Just to close the cycle of conversations. He has another talk that we unpacked in the conversation around. You don't get anyone to do anything because people come up to him after his talks and say, like, well, these are great principles about leadership. How do I get people to do this? And you're like, well, you don't get anyone to do anything. We invite them. We create the conditions for. We create a space for. They have the power. Yeah, the power is yours. That's a captain planet reference for those who understand. So I was thinking, when you're talking about the Margaret Mead quote it's really interesting to think about what the atomic unit of change is because obviously in my book I would assert that the unit of change is a conversation, and I think we can have a conversation with ourselves and we can have a conversation with another person to try and create a lime or whatever. But I agree that getting a group of people to have their vector maps instead of being everywhere, to being at least directionally the same, this is leadership. And I'm curious with your. We've talked about lots of spheres of conversation. We've been talking a lot about the big community, the organizational conversation and how it exists in different strata. I'm curious, in terms of your team, how do you see yourself as a designer of conversations, in terms of getting that group of people to discuss, deliberate, decide, any other ds that we can think of.

James Rutter 31:28

Explain more. Just what are you digging at?

Daniel Stillman 31:31

Well, because you are the chief creative officer, but I presume you don't operate by fiat. There is a group of people who discuss things together and say, ought we to do a, b or c, or should we take a plus b divided by c or none of the above. Right. The creativity at the creative team level, your creative team level, you're the one who's holding space for those conversations.

James Rutter 32:06

Yeah.

Daniel Stillman 32:07

How do you do it? What's your trick, assuming you're doing it well.

James Rutter 32:17

Do I have a trick? That's a good question.

Daniel Stillman 32:20

Well, I mean, there's no tricks, obviously, there's no tricks.

James Rutter 32:23

Again, I think

James Rutter 32:27

a lot of it does come back to giving everybody a voice, making sure people feel confident enough to use it, and then seeking to push them into places where they might feel a bit uncomfortable, because that's where the creative tension you hope, will really start to grip and move them forward.

James Rutter 33:04

I don't know if there's a trick, but one of the most impactful things I ever did was do a session with the theatre group called Punch Drunk. Have you ever come across punch drunk?

Daniel Stillman 33:20

No.

James Rutter 33:20

I know they've been to New York at times, so they do these incredibly grand, immersive theatre experiences. So they've got one on in London at the minute, which is all about the fall of Troy. And it's the kind of things where you queue up, everybody has to wear a mask, like a classic half face mask, masquerade type mask. It's usually really dark. You get let out at various places, usually in a big industrial type of site where it's very dark and you're just free to wander.

Daniel Stillman 34:01

Were these ones who made sleep no more?

James Rutter 34:04

Could well be. Was it sleep no more?

Daniel Stillman 34:06

It's because it's giant, because I remember wearing such a mask? And it must be running around early, early days when it was only supposed to run for. I'll just pull rank. It was only supposed to run for a month, and then they just kept doing it. But I think that may be them, and I feel like I should know that. But, yes, sorry, please proceed. Yeah, they totally did sleep no more. That's right. Because it's beyond immersive. It's in a warehouse and there's many, many scenes going on, and it's like beyond an escape room. Right.

James Rutter 34:42

The whole thing is just all going on. But they very cleverly guide and everybody to the same place, the denumont. So everybody experiences the same. So going back some years, I was lucky enough to do a session with them where they were just showing people mostly from kind of brand marketing, creative industry types, people, how they prepare their actors for the performance, some of the things they go through. What that just really brought home to me was the power of play, because it was all around, genuine play around, kind of very unstructured, kind of improvisational games, techniques with some loose rules and frameworks, but within which you were able to do kind of what you wanted, create scenes in your mind, write down kind of letters as if you were writing to somebody who was the thing in your head, all this kind of stuff. And then the best bit was when they open the set, they let everybody into the set one at a time, at two minute intervals. And the sets are always really dark and gloomy. And hidden around the set are candles, little candles, electronic. They were but little electric lights. And by each light is a task. And so when you get led into the set, they say, right, your job is not to be seen by anybody, so you're not allowed to be seen. And you've got to find as many tasks as you can and just do the task. And so you're let into this set and suddenly it comes flooding back to you. The experience of being a child playing hide and seek, and it being the most exhilarating experience in the world to be just in a little bundle in the corner with your heart beating and hoping the person who walks past isn't going to stop and see, and then finding this little light and opening up the paper and just reading what it says and without even thinking, just doing it. And so there was one that was like, sprint down the corridor behind you. There was another one that was pick up the mannequin and dance a waltz on the dance floor. And there's all these kind of things. And it was just such a powerful experience? Because it just reminded me that if you allow people to get beyond their tram lines, that they're told they've got to stay in and really kind of play and immerse themselves in what it really means to create your own experience, you then just ignite people's kind of imagination for what they can do.

Daniel Stillman 37:32

Yes.

James Rutter 37:35

I obviously don't do anything like punch drunk, but at least seek to have a little drop of that in every gathering.

Daniel Stillman 37:44

Yeah, but you brought your team out to something, to one of those, did I understand correctly?

James Rutter 37:51

No, this was me on my own, sadly. But I tried to bring it back. Yeah.

Daniel Stillman 37:58

How did you talk to me about that? Because you talked about giving everyone a voice and bringing in play and playfulness. How do you try and create the conditions for playfulness? In what ways are you trying to nourish your team so that they have the food, the materials to do it?

James Rutter 38:21

I'm a big lover of games, full stop.

James Rutter 38:28

And you see it with any group of people. You'll know this. You'll see it with any group of people, that you give them some silly little simple game to play.

James Rutter 38:41

I think I've seen a video of you doing, like, the shaky thing.

James Rutter 38:47

Anything like that. I think ones that involve pairs of people are particularly good. So if you can do anything that involves an interaction and is a little game,

James Rutter 38:59

you'll have done this thousands of times. You'll go from, like a quiet, dull, kind of slightly lethargic room into a room that's full of energy and laughter and possibility and what have you.

Daniel Stillman 39:11

Yes.

James Rutter 39:14

In that sense, I don't think it's rocket science. It's like figuring out ways to kind of ignite the playfulness that lies inside of all of us and to make people, oh, hey, it's okay. We're allowed. This is playtime.

Daniel Stillman 39:31

Yeah, I think it's beautiful. I have a very difficult question to ask you, and I'm not sure if I've been poking at something, and I don't even know how to ask this question, so I'll try. I'm thinking about the event that I invited you to, the leadership gathering. We were talking about difficult conversations and the sense that what I find often with people is when they're in a challenging context, there's one way that they want to be something that they want. There's ways that they think they ought to be or should be in the sense that we're angry or disappointed or frustrated, but we need to be calm or patient. We're nervous, but we feel like, we need to be confident. And I'm wondering for you as a leader, how you thread that needle. Because the reason I've been poking at this is I love this idea of everyone being themselves and feeling like we're safe to be ourselves. And I also get this sense from a lot of the clients that I coach of this idea of, like, I have to put this mask on, I have to be a certain way. And I've been really thinking about, well, how do we be the other ways and how do we do it in a way that feels good to us and good to the other people? And I imagine that in your work, it's not all play. There are some challenging conversations. I'm wondering how you sort of create a shift in yourself so that you can show up in the ways that you feel you need to in an authentic way.

James Rutter 41:05

I might throw this back as another question, because do you not think ultimately that's built on human connection? So it's very hard to come without a mask if I'm meeting you for the first time. It's just difficult. Some people maybe have that superpower that it's always out there and they just are who they are, but most of us will come with a little bit of a mask on because we're not quite sure how that connection is going to go, whether there's going to be any connection, whether we just miss each other on the way past type thing.

James Rutter 41:42

So finding ways to build that relationship in a personal way as quickly as you can, I guess, would be my sense of how you get then to a place where you're going to be comfortable to show your true self rather than your master. So.

James Rutter 42:08

So again, so in a kind of cook context, we're mostly very fortunate. People tend to stick around for a long time. So you build relationships over years. And I do think that in this kind of be an overnight success, kind of move on, climb the career ladder, have a million jobs in ten years type vibe. People overlook the real value of established teams and what teams that work together for a long time can really deliver and achieve. Because that's when you do get really high trust. You do get a sense that people turn up and are much more open, are much more willing to be vulnerable. It's human nature. We're not prepared to risk so much with people we don't know so well. If you want people to come and take the mask off, you've got to seek to build the human bonds first before you seek to do whatever the worky thing is you want to do.

Daniel Stillman 43:18

Yeah, that makes sense. That's really interesting. Thank you for. I appreciate that. It's a question I've been sort of scratching at for myself. I appreciate your perspective on it. Well, so listen, we're getting close to the end of our time together. My lord, the time goes fast. You are a delightful person to converse with, James. What's your secret? How do you do it? What? Haven't I asked you that? I ought to have asked you what? Haven't we talked about that you think we ought to have?

James Rutter 43:48

What should we have talked about? We've done a lot. Haven't we talked about inversion. Inversion of all that stuff. Citizenship, community.

James Rutter 44:03

We haven't talked about your mum. It's a well known story.

Daniel Stillman 44:08

It's not a generally well known story.

James Rutter 44:11

And it's such a great story.

Daniel Stillman 44:15

I.

James Rutter 44:16

Feel like, about the coolest mum story I think I might have ever heard.

Daniel Stillman 44:20

Well, could we put it in context? How did it come up and what was your experience of being like, oh, I should definitely look into this because I feel like we were talking about food and how happy cooks make happy food.

James Rutter 44:34

Exactly. It came up because that's exactly what we were talking about. We were talking about how happy cooks make happy food.

Daniel Stillman 44:41

Yes.

James Rutter 44:41

And that led us directly to your wonderful, glamorous mother, who came across like this celebrity tv chef before there even. Were celebrity tv chefs in 1973.

Daniel Stillman 44:57

I will put a link in the show notes. In 1972, I believe, less than a year before my brother was born, before my parents were married, my mother was invited to be a cook. She was a macrobiotic cook at the time, and she did a cooking segment with John Lennon, Yoko Ono and Chuck Berry on what was called the Mike Douglas show, which was like Donahue and Oprah of its day. And what was extraordinary, this is a very famous moment. John Lennon. Yokono agreed to come on the Mike Douglas show for a whole week with the caveat that they could bring any guests that they wanted and they were into macrobiotics. Although from the look of know, I think John was on a lot of heroin at the time. It didn't look like he'd eaten in weeks.

James Rutter 45:40

He was on more than your mum's onion cakes.

Daniel Stillman 45:43

Yes. Tajiki egg rolls. And what is quite delightful about is that many of us. I saw it for the first time when I was like 15 1415, where my mother got the video through. They offered her a tape of it and she was like, I'm never going to have a machine like this. My mother was somebody who'd given up her silverware because she thought she was going to eat with chopsticks for the rest of her life. But there was a still shot of John Lennon feeding my mother an egg roll, which happened between takes. And it was just sort of accepted, like, that's a thing that happened, but it is an extraordinary thing. And what's funny is that sometime in the think VH one had the whole week on because it was a very famous. They had lots and lots of famous people on the Mike Douglas show. And so people called my mother and they're like, hillary, are you on VH one? And now it's in. Actually, that bit is in the rock and roll hall of fame because it's the first time that John Lennon and Chuck Berry ever met and played together. You can find footage of that with Yoko ono ululating in the back. Should you care to engage. I just love that and that sound.

James Rutter 46:52

That would be my go to story for every social occasion ever.

Daniel Stillman 46:55

Let me. It does come up.

James Rutter 46:56

Mum, cook for John, Yoko.

Daniel Stillman 46:59

Right. But the point is, there's this moment where they're all. It's just kind of a cluster fuck. And my mother's like, we need to have a calm and peaceful environment, otherwise the food will taste very chaotic. And she just gives everyone a job. And they start playing very nice soft jazz. And so they're playing very weird, sort of like, very chaotic music. They chilled it down. I'm so glad you enjoyed it. Hanging out with my mother circa 1972. This is a very special time.

James Rutter 47:26

I love it. I encourage everybody to watch that clip and marvel over your glamorous mother.

Daniel Stillman 47:32

Oh, thank you. I really appreciate you giving my mom a shout out. She'll enjoy this episode a great deal. Well, besides that, anything else?

James Rutter 47:46

It literally says here, your mom.

Daniel Stillman 47:48

Yeah.

James Rutter 47:48

Rock and roll cabbage.

Daniel Stillman 47:49

Rock and roll. Yeah, that's what Sean Lennon was saying as he was cutting the cabbage. Rock and roll. Rock and roll. Rock and roll.

James Rutter 47:55

No, I mean, I guess the thing we didn't touch on, which maybe we said we would, which just to finish on it, because it's a little bit encapsulated and that good cooks make good food comment. This sense of, again, organizations working from in to out. And how actually, if you don't start with your people and their relationships or their conversations in your world.

Daniel Stillman 48:20

Yeah.

James Rutter 48:20

And how those are back again. Back. And if. And how those are promoting flourishing. How on earth can you hope to have a great product out of the world that's going to connect with the people you hope will be your customers?

James Rutter 48:34

Genuinely, I think the more time we collectively spend thinking about how we are together within our organizations, our businesses. The more productive we're going to be, the more kind of fulfilled we're going to feel, the more we're going to feel able to take those masks off and be who we genuinely are together and hopefully help each other into a kind of more flourishing future.

Daniel Stillman 49:02

What's not in that mike drop. You're right. So if you were to look back on all that we've discussed, and you were to give this talk, this conversation, a title, what would be the title of our conversation?

James Rutter 49:18

Rock and roll cabbage, surely.

Daniel Stillman 49:21

Rock and roll. Yeah, that's a good one. Rock and roll cabbage. Well, then I'll call scene.

Daniel Stillman 49:35

Thank you so much, James. This has been an absolute delight. I appreciate you making the time.

James Rutter 49:39

It's fun, yeah it was fun!

Divorce by Design - Shifting the Default Conversation with Suzanne Vickberg

Today I share my conversation with Suzanne Vickberg, aka Dr. Suz. She is a social-personality psychologist and a Research Lead at Deloitte Greenhouse. Along with her Deloitte Greenhouse colleague Kim Christfort, Suzanne co-authored the best-selling book Business Chemistry.

But there’s another type of Chemistry - or Alchemistry - that I sat down to talk to Dr. Suz about - shifting the default track of a conversation from protection and opposition to collaboration,
Some years ago I interviewed Dr. Elizabeth Stokoe, a Professor of Social Interaction at Loughborough University, who speaks in her book “Talk” about conversations as having a landscape or a “track” that participants asses and orient to rather quickly…and that we glide down that track, while we monitor the texture of that landscape, and navigate the bumps in the road…so that we can keep things on safely on track. Check out our podcast conversation here and her TEDx talk here. In the opening quote to this podcast, you can hear Dr. Suz describing this process of “landscape orienting” happening very rapidly in a divorce context.

Knowing the default path is very helpful when navigating a “hello, how are you?” kind of “small talk” conversation in a non-wierdo-way. Knowing the default track can help make things smooth and easy…when you’re visiting the store, or a bowling alley. And when you don’t know the basics of the track, things can be hard - Doing simple things in a different culture can be surprisingly slippery to navigate when you don’t know the basics of the track. 

But sometimes the default path can be extremely detrimental - especially when the default is ineffectual or becomes unconscious and habitual - we keep doing things out of rote, not intent.

In business, a common default/habitual conversational path is looking at an underperformer and putting them on a Performance  Improvement Plan in order to be able to fire them more easily,

A non-default, more conscious conversation is taking the time to learn *why* they are underperforming and helping them actually transform themselves, their work performance and their lives….and in the process deeply benefiting the company and even the community.

Seems impossible, right? Or grandiose? Carol Sandford, in her book about Regenerative Business talks about an organization that did just this… a manager discovered that a chronically underperforming and late employee was just functionally illiterate. That employee, once they felt safe to share more, helped that manager learn that many of their employees were facing similar issues. Instead of a PIP, this employee got literacy training, and became an advisor to a new literacy program developed inside the organization, which spread out to the larger community, in ripples of growth and transformation.

That is a *non* default conversation - turning a PIP conversation into a community-transformation conversation.

On a micro-scale, Dr. Suz’s book tells the story of rethinking or re-designing the “default track” for a very, very common conversation - Divorce. When that word gets said out loud, people find lawyers, put up a shield, and start digging trenches. 

There is a better way! It takes effort to deeply empathize with your “opponent” in a difficult conversation. It takes patience and imagination to collaborate with your “opponent” to design a win-win scenario. 

But the default design for divorce doesn’t usually create ideal outcomes…just conventional ones. It’s possible to create something better than you can imagine if you create the space for a transformational conversation.

Dr. Suz helps break down how “design” in these situations just means really understanding the REAL problem we’re solving and what our IDEAL outcome really could look like… BEFORE we jump to solutions.

Also check out my podcast conversation with Adam Kahane, author of, among many other amazing books, the book Collaborating with the Enemy - which is what I know a divorce can feel like. Some of his perspectives take this “divorce by design” mindset into the broader business and strategy arena.

Enjoy this conversation as much as I did…and think about how you might transform the most challenging conversations in your life and work. With more conscious creativity and intention, with empathy and collaboration…with more design you can create more of what you really want, just like Dr. Suz did for her own divorce and for her own life.

Links, Quotes, Notes, and Resources

https://www.divorcexdesign.com/

https://www.linkedin.com/in/suzannevickberg/

https://www2.deloitte.com/us/en/profiles/svickberg.html

https://theconversationfactory.com/podcast/facilitating-breakthrough-with-adam-kahane

AI Summary and Key Moments

Dr. Suzanne Vickberg shares her experience of redesigning her own divorce process with empathy and finding a solution that met both her and her husband's needs. She emphasizes the importance of focusing on the problem being solved and encourages others to consider different ways of approaching divorce. Daniel Stillman and Dr. Suzanne Vickberg discuss negotiation and the concept of growing the pie versus splitting the pie.

Key Moments

• Dr. Suzanne Vickberg defines design as intentionally creating something that leads to a desired outcome (1:18)

• Dr. Suzanne Vickberg talks about redesigning their own divorce and reverse engineering the process to help others do the same, including the conversational work involved in negotiating a new way of being (4:19)

• Dr. Suzanne Vickberg explains how she rejected the idea of protecting herself and instead focused on empathy and finding a solution that met both her and her husband's needs (12:46)

• Dr. Suzanne Vickberg emphasizes the importance of focusing on the problem being solved and envisioning the ideal outcome, rather than just trying to end the pain in the present moment (23:16)

• Dr. Suzanne Vickberg shares her unique solution of co-parenting with her ex-husband and encourages others to consider different ways of approaching divorce (25:37)

• Dr. Suzanne Vickberg talks about her values of not enjoying winning when someone else loses and loyalty, and how she applied them to her divorce process (35:34)

• Daniel Stillman and Dr. Suzanne Vickberg discuss negotiation and the concept of growing the pie versus splitting the pie (37:16)

• Daniel Stillman asks what people should say when someone tells them they're getting divorced, and Dr. Suzanne Vickberg suggests asking "how are you feeling about that?" instead of saying "I'm sorry" (48:13)

More about Suzanne Vickberg (aka Dr. Suz)

Dr. Suz is a social-personality psychologist and a leading practitioner of Deloitte’s Business Chemistry, which Deloitte uses to guide clients as they explore how their work is shaped by the mix of individuals who make up a team. Previously serving in Deloitte’s Talent organization, since 2014 she’s been coaching leaders and teams in creating cultures that enable each member to thrive and make their best contribution.

Along with her Deloitte Greenhouse colleague Kim Christfort, Suzanne co-authored the book Business Chemistry: Practical Magic for Crafting Powerful Work Relationships as well as a Harvard Business Review cover feature on the same topic. She also leads the Deloitte Greenhouse research program focused on Business Chemistry and is the primary author of the Business Chemistry blog. An “unapologetic introvert” and Business Chemistry Guardian-Dreamer, you will never-the-less often find her in front of a room, a camera, or a podcast microphone speaking about Business Chemistry or Suzanne and Kim’s second book, The Breakthrough Manifesto: Ten Principles to Spark Transformative Innovation, which digs deep into methodologies and mindsets to help obliterate barriers to change and ignite a whole new level of creative problem-solving.

Suzanne is a University of Wisconsin-Madison graduate with an MBA from New York University’s Stern School of Business and a doctorate in Social-Personality Psychology from the Graduate Center at the City University of New York. She is also a professional coach, certified by the International Coaching Federation. She has lectured at Rutgers Business School and several colleges in the CUNY system, and before joining Deloitte in 2009, she gained experience in the health care and consulting fields. A mom of two teenagers, she maintains her native Minnesota roots and currently resides in New Jersey, where she volunteers for several local organizations with a focus on hunger relief.

Full AI-Generated Transcript

Daniel Stillman     00:00

Allow me to officially welcome you to the conversation factory. Suzanne, I'm so glad we made the time for this conversation. I appreciate you being here today.

Dr. Suzanne Vickberg     00:10

Me too. Thank you for inviting.

Daniel Stillman     00:12

So let's. We have so much to talk about. Oh, my God. When did you first start to value.

Dr. Suzanne Vickberg     00:23

Know? I'm not sure I really thought all that much about design per se until sometime probably in the last ten years. I work for Deloitte in part of the organization called the Greenhouse. That is about designing experiences. And that's when the word design and the idea of design really started to be something I was conscious. Yeah. But of course, that doesn't mean that I wasn't designing things before.

Daniel Stillman     00:58

That sounds like, what are the boundaries of design as you see them now? Because it's clearly in your work and in your writing, what is designable and what design is for is not the sort of maybe more conventional definition of some people who might be listening.

Dr. Suzanne Vickberg     01:18

Yeah, I don't think I've ever been asked that question. So for me, design is really about intentionally thinking about how you want something to be, how you want it to be used, how you want to see it, how you want to feel about it, how you want to experience it, or you want other people to experience it, and then creating something that will lead to that outcome that you're looking for.

Daniel Stillman     01:46

Right. I think one of the things that's so powerful and such an interesting proposition about your book divorce by design is this idea. When we look at the world, everything is designed. I think years ago, I saw a talk with John Maida where he know showed a street, and he's like, look, this street was designed. These buildings were designed. The lamppost, the clothing, everything. And there's also that famous Steve Jobs quote about design being how something really works. Everything is designed. Who designed divorce?

Dr. Suzanne Vickberg     02:30

Yeah. Who did design divorce? I mean, it was probably not usually the people who are getting divorced. And even now, while you can design your own divorce, if you are legally married, there will be other people who have something to say about how you do it. Yeah. Right. The end of the day, a judge somewhere is going to approve your divorce and how you're doing it depending on.

Daniel Stillman     03:02

What state you live in. And this is the thing of, like, there are ways that things are already designed that may not be working. Well. I feel like there's this meme of like, am I depressed? Or is it capitalism? Am I sad? Or is it the fact that cities were not designed to be walkable? Right. So there are designs that are not designed for how we are built and what our psychology is.

Dr. Suzanne Vickberg     03:29

Yeah, I feel that really strongly. I'm an introvert, and I recognize that the world, in a lot of ways, is not designed for me, and that's why things feel hard. But I can design my life around having a little less of the things that don't work for me and a little more of the things that do. Yeah.

Daniel Stillman     03:49

So you took your design mindset and redesigned your own divorce, which is the seed of this book. It is a very powerful reimagining of the traditional ways that don't necessarily serve us. I'm wondering if you can just talk a little bit about your journey in deciding to take a creative, problem solving approach to your divorce and also to help others do it.

Dr. Suzanne Vickberg     04:19

Yeah. Well, I think that I was like many people who are struggling in their marriage, I struggled for a long time. I mean, we both did. Just really pretty unsatisfied and unhappy, but not really seeing an alternative that felt at all acceptable. We had two small children, like, two year old and a four year old. It didn't seem like something that I could even imagine doing was breaking up our family at that point. And it was this feeling of being really stuck between a rock and a hard place. It's sort of like, I can stay in this and be unhappy, or I can leave and sort of make everyone else also unhappy. And so, like a lot of people, what I essentially did for quite a while was nothing.

Daniel Stillman     05:17

You can just ignore the problem and just kind of certainly try.

Dr. Suzanne Vickberg     05:22

Yeah, that's one solution, yes. But I just kind of kept working it. I tend to ruminate on things. Usually not a great thing, but every once in a while, it's to my benefit. I just kept thinking, this can't be, like, the only possibility, these two options. And so I really tried to focus in on what is the part of this that's not working for me? And it was the marriage. It wasn't our living situation. It wasn't the family. It was really the marriage. And the way I felt in it. And I won't even say that the problem was my ex husband. The marriage, the romantic part of our relationship, the sort of lifetime partnership as a romantic couple, was the part that wasn't working. And once I sort of really started to think about it that way, I thought, well, can't we just end that part and keep the stuff that works? And I started talking to him about it, and I said, let's just call that over. But no one has to leave. We can stay in our home. We can raise our kids together. Why not we do that? Well, let's just call the marriage over, sort of remove that part from the picture and continue on with the things that do work for us and don't change anything else. I mean, that's really how it came to be. And the book and sort of the process that I help people through to think about their own marriage and their own divorce and how to get creative in their own way was something I sort of reverse engineered after the fact, when I realized what we ultimately were doing. I think it would have been easier to do if I had had this mind frame from the beginning, but it was more a realization. Like, we designed this to be very different from the traditional.

Daniel Stillman     07:52

I mean, well, what you did was, there's this great diagram I don't know if you've ever read collaborating with the enemy by Adam Cahane. He's an amazing facilitator, and he basically has this flowchart diagram of, like, well, if you can't force your way to a new wave with someone, and if you don't want to leave and you can't accept things the way they are, and you don't want to just give in, like, there is this last approach, which is engaging with someone in rethinking or reimagining or redesigning the way things are. It seems simple on the face, but we're subsuming years and years and years of rumination and avoidance, and you finally being able to broach the conversation. And this is really what we were talking about before we started recording. At the conversational level, you had a whole series of conversations with yourself that led you to decide to have a conversation with your then husband, and an almost infinity number of conversations afterwards that had to happen to continue to negotiate a new way of being, to explain it to others, to defend it to society. Can you just talk? Because it seems, on the face, so obvious that divorce needs to be redesigned, because the normal design would be, go get another house, not see your kids as much, spend a whole bunch of money, and we're not optimizing for what we really want. That seems simple, but I know that on a conversational level, it was work. And I'm wondering what you can share about the conversational work that went into getting to that new state and then sustaining that new state.

Dr. Suzanne Vickberg     09:49

Yeah. Well, I think one of the things that most people do either before or after they've started talking to their spouse about divorce is they talk to other people about it. Right. And those people might be their loved ones, or they might be their therapist or there might be an attorney, they will go and just, I just want to get the lay of the land. I just want to understand what my rights are or how this would work. And there's nothing wrong with doing that, of course. And for a lot of people, it's a really important step. But if you start talking almost to anyone else about divorce, what's going to come back at you is sort of all the traditional stuff. It's how people view divorce. And the first thing that most people will start encouraging you to do is to protect yourself.

Daniel Stillman     10:44

Yeah.

Dr. Suzanne Vickberg     10:46

And again, I'm not saying some people don't need to do that, but you're immediately, when you start thinking about this in terms of protecting yourself, you are immediately setting up a dynamic, at least in your mind, if not actually with your partner, that we're not in this together, we are against each other in this. And so the conversations you start having sort of usually send you down in a certain direction, which is going to be some kind of combative situation, even if you're reasonably cordial. Let's set everything up. Let's make sure we have all these agreements, because we probably will not be able to get along in the future. We will not be able to manage things together. So those conversations that I had early on with people and that most people do, I mostly found not very helpful, frankly, loved ones who did the same. First of all, the first reaction, at least of my family and friends, was like, really, your marriage is not that bad. You should stay. The assumption always that you should stay. If you can in any way find a way to stay, you stay. Yes, that's what you do. And then once people start to accept that, in fact, I'm not going to stay, or at least not stay married, then they start pushing you down this path of. Because I started telling people right away, well, we're going to get divorced, but no one's going to move out. We're going to live together and we're going to raise our kids together.

Daniel Stillman     12:42

Everyone's hair, I'm assuming, moved back a few inches.

Dr. Suzanne Vickberg     12:46

Everyone says, you can't do that. That's a terrible idea. Why is that?

Daniel Stillman     12:53

There's no good or bad ideas in a brainstorm, guys. We're brainstorming here exactly why is that a terrible idea?

Dr. Suzanne Vickberg     13:02

And because people just couldn't wrap their brain. Like, they just couldn't see it. It seemed weird.

Daniel Stillman     13:10

And your experience has proved that it is, at least for you in your situation, in terms of what you were trying to optimize. For a great solution.

Dr. Suzanne Vickberg     13:21

Yeah.

Daniel Stillman     13:22

Right. You got more time with your kids than you would have had if you were splitting time between two houses. I was just telling my wife about this, giving her the thumbnail of like. And you don't have to buy another house, and you don't have to see them only half the amount of time. And because there's three adults in the house, you got to have more flexibility and more consistent care for the kids. Like, all these things that everybody in these conversations were like, that's a terrible idea. So the conversation you had with yourself after those conversations, somehow you kept feeling like, this is still the right approach.

Dr. Suzanne Vickberg     14:02

Yeah, I think I'm not a very good advice taker.

Daniel Stillman     14:08

That's good.

Dr. Suzanne Vickberg     14:11

Most people really aren't, frankly. I mean, any of us who's ever given advice and watched the people we're giving advice to never ever do the thing that we told them to do. But I'm stubborn. I'm not easily convinced of things. I can be convinced, but it takes a while, and usually I have to sort of hear something multiple times. And I didn't buy it, I didn't see it, and I was the one living in it. And so I think I had a clearer picture than anyone else of what our relationship was like, what I could imagine it could be in the future. And, I mean, honestly, at the time, what we agreed was, we'll just do this as long as it works for both of us. And it's been 13 years. Did I know that we would be doing this for 1315 years? No, I didn't know that we wouldn't have. It was open ended. Yes, but I don't know. I just felt like I don't want to do what everyone else is telling me to do.

Dr. Suzanne Vickberg     15:27

I don't believe them when they say it can't work. And the other thing people told us was like, okay, fine, maybe you can make it work for a little while, but one of you is going to meet someone, and then what? That could never work.

Daniel Stillman     15:39

Right. And then you have to have those conversations.

Dr. Suzanne Vickberg     15:41

Yeah. And in fact, he met the woman who's now his wife, Anna, almost right away. Within two months of us calling our marriage over, he had met her. And again, he didn't know he was going to marry her. They waited ten years before they got married, but she was sort of like, within a year was in the picture. And I continued to think, I'm glad. I still don't see why this can't work. And she moved in with us. Once we added onto the house so that we had a little bit more space.

Daniel Stillman     16:20

So I think this is what we would call varsity level conversation design and innovative thinking. There's some layers that I think are worth peeling back on this, because in my way of thinking around design, we're optimizing for something. There's some heuristic we're using to judge whether or not this is a good design. And so when people were saying to you, you've got to protect yourself, you looked at that. What I'm hearing is that heuristic optimizing for protection. There's costs to optimizing for protection. There's pluses to being aware of protection. But there's another set of design principles that you wanted to design your conversation with your husband and your family for. And I think curiosity, bringing an options mindset versus. There's got to be one way or a goal setting mindset of, like, what am I really trying to create here? Mindset. What do you feel like you were trying to design for in those conversations? You weren't necessarily designed to protect yourself. You were really trying to optimize for something else.

Dr. Suzanne Vickberg     17:44

Yeah, no, I definitely rejected the protect yourself heuristic. And again, I'm not saying that that's not important for some people. I know every marriage is different, and people are sometimes in a marriage that is

Dr. Suzanne Vickberg     18:02

much more challenging in certain ways than mine. But for me here, I'm looking at this person that I've been with for ten years, and while we're not working as a married couple, I just didn't feel like there was a reason he would be out to get me.

Dr. Suzanne Vickberg     18:25

So I sort of just outright rejected it. We didn't even have any kind of financial agreement or anything for the first few years. And we did put one in place eventually because it was sort of like, oh, he had a business, I had a retirement account. We wanted to sort of figure out, well, how is that all going to work? So we did get an agreement in place eventually, but I think what I was really focused on, number one, is empathy. I was looking to have my needs met, but I didn't want to do it at the expense of him getting his needs met. And not all the needs were compatible in the moment because he wanted to stay married and I wanted to get divorced. That was an incompatibility. But digging underneath that and trying to understand why did he want to stay married was the important thing. And it really wasn't about me. It wasn't about staying married. To me, yes, it was about the family. It was about the home. It was about being in the community as a married person.

Daniel Stillman     19:43

Yes.

Dr. Suzanne Vickberg     19:45

There were things about being married that he really valued that. And I'm not saying he didn't value me as a person, but to me it didn't feel like, oh, this is about, you must be with me.

Daniel Stillman     19:58

Right. It was about the Perry marriage. It was the marriage trapping all the pieces around it in the people that you advise and coach. It is very hard to tap into these resources when we are in a state of scarcity and survival, to get into empathy, to get out of protection and into curiosity and empathy and being generative. I would say nontrivial. They say in the mathematics world, the solution is nontrivial.

Dr. Suzanne Vickberg     20:41

Right.

Daniel Stillman     20:41

Which means we don't know if a solution exists and we don't know how long it will take to find the right solution. So how do you get people into these really important design mindsets of a willingness to prototype, an openness to empathy and being generative? I mean, I suppose if I was going to do it in the design thinking order, it'd be empathy, a generative mindset, and a willingness to prototype, because you and your husband at the time said, like, well, let's try this for now and let's inspect the results as we go. How do you coach people to get out of that protection and panic survival mindset into this design thinking mindset to really reevaluate their approach? Because it does not come for free.

Dr. Suzanne Vickberg     21:36

No. Well, it's not easy, as you said. Although I will say that I think that people, anyone who would approach me for coaching around this would already be a step ahead because they're already thinking, yeah, that sounds good. I think your solution may not be the exact right solution for me, but I would like to do this differently. So that is one thing. It's sort of like some people are starting out with a little bit more of an optimistic and open mindset that, well, maybe I don't just have to do whatever someone else told me to do. Another thing is that it's not something that happens in a linear way. It's like there are days when even the most open minded person is feeling really hurt and they're angry and they're just not right now. They're not able to be empathetic because they feel their partner is not empathetic and they're mad and heartbroken. But you could see the same person a week later being in a totally different place as things progress.

Dr. Suzanne Vickberg     23:04

That's another piece of it. And then what I really try to do with people is get them to focus in on what problem are you actually solving for? And then how would you want it to be if you could? This vision of what's the perfect divorce, which is not the same for everybody, but is a new way for a lot of people in terms of thinking about it and thinking just, like, let's just forget all the realities of the situation for a minute, like we do with almost any kind of creative problem solving. Let's put aside some of the constraints and let's focus on blue sky thinking, like, if I could have anything, what would it be? And then start thinking about, like, okay, well, I may or may not be able to get all of that, but how can I get closer to that than to the traditional path? Yes.

Daniel Stillman     24:04

This is such a powerful idea. It's what my coaching coach would call creating from the future. Right. And very often, we're in this present moment, which is just filled with pain, and we're trying to optimize for the cessation of pain. And the way you tried to do that and the way many of us try to do that is to avoid it, to numb it out, and to just ignore it for as long as possible, because that's actually one of the most efficacious solutions in the present moment, is just try not to feel it. Try not to feel anything. Numb it down. And what you're talking about is not the first step of, like, well, how do I end this pain? Sometimes the most efficacious way to do that is just to go to a divorce lawyer and serve them papers and say, I want a divorce. But you're talking about a much, much harder thing, a much more challenging thing, which will produce greater results for somebody, which is to think about, what do I really want? Not just a month from now, when I'm feeling less pain, but a year from now, two years from now, do I want to still be able to see my cat, our cat? Do I want to see our kids? Do I want to be able to go on vacations together? Like, whatever that optimal dream is. You want people to dream a little bit and then work backwards. And that is so powerful.

Dr. Suzanne Vickberg     25:37

That's really the point of sharing my story, because, let's be honest, a lot of people don't want to live with their ex for a decade and a half after they.

Daniel Stillman     25:48

It's not for the faint of heart.

Dr. Suzanne Vickberg     25:50

Not for everyone, but that's not what we're talking about here. That is my solution, our solution for our family, which has worked great for us, but it's so unique. We're not the only ones who do it, by the way. There are other people who have maybe slightly different flavors, but it's still pretty unique. And so the reason that it's so important to me for people to hear about it is because it helps them see, like, oh, okay, well, there are different ways, and maybe I can come up with my own different way.

Daniel Stillman     26:27

Yes. That there are many, many ways of being, and that really changes. I mean, we're talking. My favorite axe to grind is the conversation. Right. Changing the conversation in the culture around divorce. It's a profound shift that can happen, especially if somebody like you did goes and tells some people, I want to make a change. Maybe they won't get the response of, like, you can't do that. So I feel like, will there be a sequel called marriage by design? Has somebody written that book? I should have checked on this, because, in a way, I mean, I actually wrote this in my book. Some people think divorce is an end to the conversation of marriage, but it's actually an agreement to continue. And it either means. I had an ex who she and her boyfriend at the time divided up the bars in Philadelphia. You know what? These are your bars. These are mine. We will never see each other again. That is our agreement. And then she saw him in one of her bars, and it was like, you're violating the agreement very clearly. I got all the bars south of Market street. So it's an agreement to continue the terms of the conversation, and you had a very different set of terms. Like, we're going to co parent. That's a very different set of terms. To be together in a different way. Do you think there was a time, if you'd thought about redesigning your marriage, that it could have been redesigned? I also know that you talk about, like, you tried many things, and so I think there's a danger to that approach of thinking.

Dr. Suzanne Vickberg     28:19

Yeah, I think that he and I are fundamentally just like, a mismatch. So could we have redesigned it? Sure, we had some conversations about that along the way, but I have the privilege that very few people on earth have of watching my ex husband succeed in a relationship with someone else up close and personal. I am there every day.

Daniel Stillman     28:55

And you celebrate it.

Dr. Suzanne Vickberg     28:57

And I do celebrate it. I'm happy for both of them. I'm so happy for my children. But I watched their relationship, and she and I were very good friends. We get along really well and are very compatible in a lot of ways and similar in a lot of ways. And we're different in a lot of ways. And her relationship with him is very different than the relationship I had with him. Not that I'm saying that's the only thing that could have worked for him, but watching that and how that works for him and frankly, just watching my own life and what works for me now, I'm like, yeah, those two things, they just weren't compatible. We want different lifestyles.

Daniel Stillman     29:43

Yes.

Dr. Suzanne Vickberg     29:44

And they're compatible for raising kids together and for living here, but not for sort of, like, going through life as a couple. Yes. But for other people, sure. Redesigning marriage. I mean, you will hear this once you start talking to divorce people. A lot of people will say, if I had had every other weekend off to myself to do the things that I care about, I could have stayed married a lot longer.

Daniel Stillman     30:12

Yes.

Dr. Suzanne Vickberg     30:13

We have this idea that, oh, we have to be with the family all the time or with the partner all the time, or taking care of the kids all the time. We don't get time alone to live our own life once we're married.

Daniel Stillman     30:26

Most of us.

Dr. Suzanne Vickberg     30:28

And then you get divorced, and many people are forced into it, like they didn't want every other weekend without their kids. But now they have it, and they figure out how to make the most of it, and they can learn to really appreciate it. And a lot of people will say, if I could have had that, the marriage might have worked.

Daniel Stillman     30:47

Yeah. I feel like I interviewed one of my high school friends who happened to write a bestseller called Fair Play. I had her on some time ago, and she designed a card game for couples to literally put all the cards on the table around who's holding which cards in terms of managing the life. And women hold more of the cards in many relationships and don't have the time to live their whole lives, which is why she wrote a second book called Unicorn Space. Shout out to Eve, sorry, but it needs design. It needs a redesign. The process of being married certainly needs a redesign. And the process of getting divorced needs, as you said, it's a cyclical design process. So I think one of the other things I'm curious about is I imagine that in coaching someone to be creative about their process of getting divorced, they, too, will need to become a coach to the people in their lives, especially their spouse, to continuously. Because one of the things I heard you say in your conversation with your then husband is, oh, it sounds like this is using an appreciative inquiry lens, like, oh, this is the thing you really want. Yeah, this is what staying married means to you. And so I think what would it be like if you could have that and it was still compatible with the thing that I want? Because I think it is that conversation. How can people who want to have this conversation with someone that they are in an agreement with get into the process of coaching them through renegotiating that level of clarity, of detail?

Dr. Suzanne Vickberg     32:43

And I think one of the things that can help is honestly reading about negotiation. And there are different, obviously, lots of different schools of negotiation. And so you want one that's going to be focused on maintaining a relationship long term with the person that you're negotiating with, not like a one time negotiation, and I don't care what happens to the person.

Daniel Stillman     33:08

Right.

Dr. Suzanne Vickberg     33:10

But we had more of a trivial situation when we first split up. I moved into the guest room because I wanted the space most, so I just moved. But then we had to kind of have this negotiation about who keeps the main bedroom because it was bigger and more closets, and we both wanted it.

Daniel Stillman     33:29

Yes.

Dr. Suzanne Vickberg     33:33

So we had to have this conversation. It's like, I want the room while I want the room. Well, we can't both room. So why do you want the room? And for me, it was like the closets. We just painted it this color that I loved. For him, it was like, because I feel like I should be able to get it because you're the one moving out. The tv is in here. There was no tv in the guest room. Tv is in here. The kids come looking for us in here. Like, I don't want to be in a different room when the kids come looking. But we wanted it for different reasons.

Daniel Stillman     34:13

Yes.

Dr. Suzanne Vickberg     34:14

And so once we talked about that, it's like, okay, fine, I don't care about the tv. I feel like the kids can find me, and I will move into the guest room. I will paint, have it painted color that I like. I will keep half the closet in the master room, and I'll get the closet in the guest room and part of the closet. So it's figuring out what is the disagreement actually about, again, what's underneath. Whatever it is I'm saying I want. And whatever you're saying you want. Yes. And if we can find out what's underneath it, then we might be able to both have what we want.

Daniel Stillman     34:56

Yes. Getting to that level of curiosity and empathy is a tremendous accomplishment.

Dr. Suzanne Vickberg     35:06

Yeah.

Daniel Stillman     35:06

I think I just feel like it remains to be said, like, if we're talking about the conversational level of redesigning divorce as a broad idea,

Daniel Stillman     35:19

it seems good and valuable on the face, but each one of those conversations takes some juice.

Dr. Suzanne Vickberg     35:26

Yeah. And I think a lot of it's about getting very clear on about who you are and who you want to be. I have never been a person.

Daniel Stillman     35:38

Who.

Dr. Suzanne Vickberg     35:39

Can enjoy winning when someone else loses. I don't want to play a board game with you. I would rather you win because if I win and you care about it even in the least bit, and now you feel bad, then I'm going to feel bad. And I don't enjoy winning that way. Yes. When I watch a sports game on tv, even if I care about which team, I always feel for the other team. So that's part of who I am and who I want to be. Yes. And so in every little interaction we had, as we were figuring things out, I wasn't going to appreciate whatever I had won if it meant that he lost. That was important to me. I also write in the book about my really strong value of loyalty and how that for a long time is part of what kept me married. Well, I'm loyal to him. I cannot divorce him. But instead I took that loyalty and said, what does divorce look like when you're loyal? How can you apply loyalty in divorce? It's by continually thinking about how what you do is going to impact the other person. And it's not martyrdom. It's not that I just said, oh, well, whatever he wants is great, or that, oh, I'll just suffer and he can have everything his way. But it's just about the balance and really doing best to find.

Daniel Stillman     37:16

For you. We talked about negotiation, and I'm just thinking about getting to yes, which is the Harvard project and negotiation classic. I actually went to the Harvard Negotiation Institute for a week long negotiation intensive. I always tell people it's the best business vacation I ever went on, like going up against all these lawyers and losing and learning the process. I had my teacher, Bob Bordon, on the podcast years ago, and one of the things that I learned was this idea of growing the pie versus splitting the pie. And that's really what you're talking about here, is this protection mindset is coming from a scarcity mindset. And the idea that we can both have what we want and what we need and make something better than we thought was possible is a profound shift. And believing that it's true, believing that it's possible means that we can be willing to create it.

Dr. Suzanne Vickberg     38:18

And I actually talk about getting to yes. I included a little section about it in my book and growing the pie. And that's probably even where I told the story of that example. I just gave and it's funny because when I was, I went to business school many years ago, and I read getting to yes. And I thought, should I be updating this? I'm sure there's more current models of negotiation. Like, maybe I should be reading a new negotiation book. But I just decided, you know what? Okay, fine. Yeah, I can do that. But it works. The model makes sense still today. And so I decided ultimately, I was going to stick with it.

Daniel Stillman     39:00

So, speaking of books, this is not your only book. I know there's another book of yours that's hiding behind you in your virtual screen. How do you put those together in context? Do you see a connection between your two books? What's the yin and yang of them in your perspective?

Dr. Suzanne Vickberg     39:17

And so, actually, I have a third book that come out in November.

Daniel Stillman     39:21

Oh, so embarrassing of me to not know that.

Dr. Suzanne Vickberg     39:23

Well, it's not really been out there yet because we've turned it in, but it's not going to come out till November. And the reason I'm raising it is not just to talk about all my books, but because I have had to think about the thread. Like, what is the thread in my career and my mission? So the new one is called the Breakthrough manifesto, and it's about creative problem solving in teams. And then my first one, which you can see there, is called business chemistry, which is about relationships at work and how each of us prefers to work and communicate and make decisions, and how understanding what someone else wants and needs is one of the most important ways that you can create a stronger relationship with. Know that first book, business chemistry, and the third one, Breakthrough Manifesto, are both books that I have written with my co author, Kim Christford, as part of my work at Deloitte. Divorce by design is my personal book that sort of falls in the middle, but I really see them all three as like, the thread is really about relationships and creative problem solving.

Daniel Stillman     40:35

That's a good thread. I'm wondering, we had this little snippet before we started recording about whether or not we have a personality, what our self is, and the ways in which we like to be can rule our lives. This is what we've been talking about, in a way, is dialoguing with ourselves in order to find more useful and effective ways to collaborate to get what we really want. Which begs the question, like, do we? You know, if, let's say there's somebody who's like, I like to win, but they realize that it's not helping them get what they want. The question is, how do we be another way? And then begs the question, who are we? Who am I? Is there a way I am? Or how do I access other ways of being?

Dr. Suzanne Vickberg     41:33

Yeah, well, I certainly don't have the answer.

Daniel Stillman     41:38

I don't either. That's why I'm asking the question.

Dr. Suzanne Vickberg     41:40

I am on the journey of exploring that. But I've been thinking of, I mean, I've been reading a lot of books lately about this question, essentially, and what is the self? And also, what are all these thoughts that just constant in our brains and how they're often so not helpful. But I am a person. I am very self reflective, and I analyze myself all the time. And I have just been starting to be open to the question that is that good for me? Does it do more harm than good to insist that I am this type of person or that type of person? Does it close me off to a whole nother range of new possibilities? So I've started thinking, like, well, then how would you express something about yourself? And I've started thinking, well, maybe the language is more like instead of, I like to win. I have often enjoyed winning.

Dr. Suzanne Vickberg     43:01

I have been a person who likes to win. I don't know. Somehow, instead of saying I am, is there other language we can use that leaves us more open to evolution? Yes.

Daniel Stillman     43:18

And it seems like in my own experience, and certainly in your experience and in what we are and you are advising to your clients, is we have to be able to access other ways of being from time to time in ways that are authentic. And I think the thing that I've struggled with is this idea of, like, well, I want to be as I am, but sometimes I have to be more than I feel like I can be. Or that terrible phrase, tone myself down. Right. But this is the use of self and coaching ourselves to bring the right amount of blank into the conversation.

Daniel Stillman     44:05

It's a pickle.

Dr. Suzanne Vickberg     44:06

Yeah. It's similar to the same question of how do I use empathy in my relationships at work or with my ex and understand what he wants? And then I understand what I want. And then we're trying to figure out how we can both get what we want. And I sort of feel like it's similar in what of myself if I have a self? Do I bring to the world? If I'm an introvert, as I often think of myself, I'd really rather not be in the front of the room a lot of the time, or maybe ever. But my role at work requires that sometimes. And so do I double down and say, no, this is me, and I don't enjoy that. And therefore we'll never do it. That would be legitimate. I probably wouldn't be able to keep the same job. Or do I say, well, I'm going to figure out a way that I can do that only once a month and not every other day, and that will be like a good balance between what's comfortable for me and how I like to do things versus what's needed of me in my job. So I think it's all understanding, ultimately, what do I want? And if I want this job, for whatever reason, then I have to find the right balance between how much of my preferences can I bring to it?

Daniel Stillman     45:41

Yes.

Dr. Suzanne Vickberg     45:42

And how much do I need to flex?

Daniel Stillman     45:44

Yes. It's a negotiation with yourself and the world, a conversation. So, man, oh, man, I've really enjoyed this conversation. The time's flown. What have I not asked you? What have we not talked about? What is important to say that has not had a chance to be said?

Dr. Suzanne Vickberg     46:04

Yeah. I think one of the things is, even though I have said that having conversations with other people around, for example, trying to get creative around divorce is often not helpful because everybody tells you how you have to do it. Yes. And it's really important to be able to listen to your own voice. At the same time, I have found it very valuable to me for me to talk about it because I'm not embarrassed or ashamed or sad or lonely or heartbroken or any of those things. I for a long time, felt like divorce would ruin my life and my family's life.

Daniel Stillman     46:58

Yes.

Dr. Suzanne Vickberg     46:59

And it didn't because we found a way to do it so that it didn't. And I'm proud of it. And we are all proud of it.

Daniel Stillman     47:08

Yes.

Dr. Suzanne Vickberg     47:09

My son is going to college in the fall. He wrote his college essay about our family and our household and our divorce.

Daniel Stillman     47:17

That's wonderful.

Dr. Suzanne Vickberg     47:17

And how it has helped him be more creative and seeing more options. So for me, instead of sort of hiding something that other people might think is weird or that's their problem, there are people who are like, oh, often I think they sort of maybe misunderstand the situation or whatever. But I do think talking about what you're doing or what you're trying to do is that sort of like bring it out into the light. Yes. Can make you feel differently about it than if you're trying to keep it close because you don't want other people to know that this is happening. Yes.

Daniel Stillman     48:08

So this begs one final question and one of my own personal axe to grind. What would you like people to say when someone tells them that they're getting divorced. If you could wish, if you could give everyone the card that says exactly, like, just read off the cue card and say blank, what would you want people to say? Because what they say now is, I'm so sorry. And I think there's probably a better response in that conversation.

Dr. Suzanne Vickberg     48:37

Yeah, I do have a response, but I do think this is important, and I would like to keep perfecting it. So I think it's something along the lines of, oh, how are you feeling about that?

Daniel Stillman     48:50

Damn, that's good. That's really great.

Dr. Suzanne Vickberg     48:54

You also don't want to say, oh, great, you're getting divorced, because I usually.

Daniel Stillman     48:59

Say, I'm sorry and congratulations.

Dr. Suzanne Vickberg     49:02

Right.

Daniel Stillman     49:03

But you're threading that needle in a much more even way that opens up the opportunity for them to express what they're. Thanks for sharing that with me. How are you feeling about that?

Dr. Suzanne Vickberg     49:15

Yeah, there's no judgment there.

Daniel Stillman     49:19

That is, it's almost like you wrote a whole book about this and have thought deeply about these conversations. So that's a wonderful redesign moment for everyone. The next time somebody offers this piece of information to them, to us to welcome it and to be curious not to judge it. Suzanne, where should people go on the Internet if they want to learn more about all things Suzanne Vickberg?

Dr. Suzanne Vickberg     49:51

Well, they can. I have a website, suzannevickberg.com. I'm on Instagram at Suzanne Vickberg, so they can find me in those two places. The book divorced by design is available on Amazon and Barnes. And, and, you know, it may not be in your local bookstore, but you could request it. And there's a way to contact me on my website or know through Instagram.

Daniel Stillman     50:18

I can attest to. I, that's how we started this conversation.

Dr. Suzanne Vickberg     50:23

And also LinkedIn. I love connecting with people on LinkedIn. And on LinkedIn. It's sort of like the multiple parts of my interests in life. More of the divorce stuff is on Instagram. More of the other creative problem solving stuff is on LinkedIn. I do cross it over a little bit, but I'm happy to connect with anyone on LinkedIn, too.

Daniel Stillman     50:45

Wonderful. Suzanne, thank you so much for your generosity in this conversation. Thanks for writing the book. And I think we can call scene. That was wonderful.

Dr. Suzanne Vickberg     50:56

Thank you for designing a great conversation.

Daniel Stillman     51:00

That's great.

Conversation Wisdom from an AI-savvy CEO

My guest today is Jay Ruparel, co-founder and CEO of VOICEplug AI, a Voice-AI company empowering restaurants to leverage AI and automate food ordering using natural language voice ordering at drive-thrus, over the phone, websites, and mobile apps. VOICEplug's technology integrates with existing systems and apps, allowing customers to interact with the restaurant using natural voice commands, in multiple languages and be serviced seamlessly.

I wanted to sit down with Jay to unpack what he has learned about how conversations are structured (for computer-to-human interaction) that he brings into his CEO (human-to-human) conversations - crucial conversations, with his senior leadership team and his broader organization - does an AI-savvy conversation-aware CEO approach conversations and interactions with a different eye?

We also focused on a few questions of deep concern for our culture today: the responsible and ethical use of AI and how it might impact the future of work.

Through our conversation, it became clear that:

AI is great for:

Repetitive or highly similar and constrained tasks. Ordering fast food at a drive-in, VOICEplug’s use case, is a perfect context for AI. In these kinds of conversations, there are boundaries on the scope of the interaction and a clear set of intents and possible goals.

Jay also points out that his AI is trained on many, many different instances of people ordering food from other people. So, the voice-driven bot can get better and better at these kinds of conversations, all the time.

Humans are best for:

High-risk and high-complexity conversations with no clear comparables or no clear scope. For Jay’s conversations with key industry stakeholders, at company-all-hands, and with his leadership team, AI can give him ideas or first drafts, but ultimately, he needs to navigate nuance with his human conversational intelligence.

++++++++++++

AI is great for:

Crunching lots of data (which is always from the past) and summarizing it.

Humans are best for:

Deciding what kind of future they want to create.

Jay points out in the opening quote that the Human mind can think, reflect, envision and CHOOSE an ideal future, creatively. AI can do a lot of that…but it can’t choose the future it wants. That is still a uniquely human strength - to dream and to choose to create that dream.

Jay dreams of a future where work is a deeper and deeper collaboration between humans and AI, where humans focus on higher-value activities while AI takes over repetitive tasks.

Jay goes on to suggest that curiosity and powerful questions are THE most critical of human skills.

When I asked Jay to share his favorite ways of designing conversations, he shared three tips:

Take just a few minutes before a meeting to be very clear about your key one or two objectives for the conversation. In other words, start the end in mind. Another way of putting it is to take time to set an intention. You might enjoy my conversation with Leah Smart, the host of one of LinkedIn’s top podcasts, on just this idea.

If Jay is meeting with folks he doesn’t know as well, from outside the company, like new clients or stakeholders, he’ll deliberately slow down the conversation and delay getting to the core objective. Instead, he’ll spend 20-30% of the meeting time getting to know them, talking about other things, all in service of trying to understand them as people, and their conversational style

Jay consciously chooses some conversational areas to NOT be highly scalable or automated - he shares a story about being offered an AI tool that would send automated and personalized birthday emails to his employees. As he says

“What is the point of me having to use that as the CEO (when)…that relationship, that wishing someone on their birthday as a personalized conversation means so much to me. That's the last thing I would want to ever automate.”

Not all conversations, even ones that can seem small and inconsequential SHOULD be automated. It is possible that a real, human touch will be the ultimate in luxury in the future.

Links, Quotes, Notes, and Resources

https://voiceplug.ai/

Jay on LinkedIn

Min 38: The Importance of asking the right questions in an AI-driven world

“In this new AI driven world, the answers are out there, but the questions are really important. And that's why this whole subject of prompt engineering, it's going to get more and more important. In the organizational context also, we have kind of given up a little bit on curiosity as a human trait. somehow that has been waning and now has to come back to the fore, basically, getting answers is easy. That's the way I think the future is going to be. You can ask a bunch of people and you'll get answers, but what questions to ask, how to ask them.

What context to keep in mind, how to make the questions, have the right language, the right conversation style. This is very, very important.”

AI Summary and Key Moments by Grain

Jay started VOICEplug to improve human experiences with technology, specifically in the food ordering industry, by using AI to understand human language (0:32)

Jay and Daniel discuss the difference between augmented and artificial intelligence, with Jay emphasizing that AI should augment human capabilities rather than replace them (2:42)

Jay acknowledges the limitations of AI in envisioning the future in isolation of the past, and emphasizes the importance of human creativity and envisioning capability (7:52)

Jay discusses designing conversations to enable humans to have better conversations rather than just replacing them with bots, including using voice biometrics to personalize interactions at a drive through. (20:29)

Jay shares an example of choosing not to automate personalized birthday wishes and discusses his approach to designing conversations as a CEO, including starting with clear objectives and considering the context and participants (25:04)

Jay notes that AI is past-oriented while visualizing an ideal future is the job of humans (35:11)

Daniel and Jay discuss the positive and negative aspects of AI learning from existing workforce and pushing everyone to reinvent the way they deliver value, and the future of work involving a mix of humans and AI bots working together (47:47)

Full AI-generated Transcript

Daniel Stillman 00:00

I'll record here and then I'll officially welcome you to the Conversation Factory. We're live. Jay, thank you so much for making the time to have a deep dive conversation with me. I really appreciate it.

Jay Ruparel 00:14

Well, thank you for having me. I'm really excited being a part of this podcast.

Daniel Stillman 00:18

Thank you. So can we put VOICEplug in context and if you could talk a little little bit about why this problem is important to you and why you started the company.

Jay Ruparel 00:32

Yeah, so I have been in the broadly, you can say, data science, analytics, AI space for over a decade and I've always been looking for what AI can do to really impact human experiences with technology. And my previous company, we were doing some work around AI in retail and often it was about the technology has moved so fast. But there is a whole segment of people that is struggling to learn and understand how to best use technology, how to have the right sort of interactions, conversations with technology. And so really what Brock got me thinking about this problem is how can technology do the hard work of understanding the human language rather than humans having to understand how do I deal with technology? And so we really took that as the basis and said, if you look at industries today, what are some of the big problems that we see in human computing interactions that we can solve through AI? And that's where we built initially a minimum viable product for voice based ordering and also voice based shopping and took it out to the customers, got their feedback, we got overwhelming feedback, positive experience that customers had when we showed them the voice ordering feature. And we felt that there was a real need for that with just the kind of labor issues that existed in the hospitality industry and the not so pleasant experience that people have had when ordering food, whether it's at the drive through or over the phone. And that's where the journey of voiceplug started, is basically with the idea that how can we make the human experiences with food ordering using AI significantly better than what it has been?

Daniel Stillman 02:42

So on our last conversation, we talked a little bit about augmented versus artificial intelligence. And it seems like your technology sits at a layer where the human eventually can interact with a human, but there's technology that's mediating a layer and maybe eliminating the human at one level, but in other instances making their lives on the other side of the technology easier and more efficient too. Instead of a direct human to human interaction with a phone in the middle, there's a bot in the middle that's helping smooth over the interaction. Can you talk a little bit about your view of augmented versus artificial intelligence?

Jay Ruparel 03:27

Of course. So most of us think artificial intelligence is basically what would replace natural intelligence or human intelligence. And so a lot of the activities or jobs are thought to be. If AI comes saying the fear psychosis that prevails about AI taking over jobs is because it is thought of as something that replaces humans. Right. Whereas whether it is our solutions and a lot of companies are approaching it with this angle is to say how can we really augment current human capabilities by using AI to do tasks that can be automated, that are routine, that don't necessarily need the best of human creativity. Really dividing the set of activities to what can be best done by automation and AI and what activities still need the human creativity, the human compassion. So for example, when it comes to dealing with guests in the kind of hospitality industry experience that we have had, the compassion with which the staff can deal with guests in a lot of different scenarios, the creativity involved in solving specific problems, however good an AI solution you create, cannot replace that. But there are things that are automated that are done day in and day out. Like for example, I want to just order the same thing at the drive through every time I go there. You don't want necessarily human stop dealing with that. The AI can remember the customer say, would you like to repeat your last order or your favorite order? Yes. And then within 30 seconds they are through because the customer is looking for quick throughput efficiency at that time. So really augmented intelligence is really augmenting the human capabilities, human intelligence to really deliver the best output for the end customer.

Daniel Stillman 05:48

Yeah. Where do you feel like the limits are? You talked a little bit about where sort of a voice activated bot shouldn't be used. Where else do you feel like the limits are versus where it's best deployed?

Jay Ruparel 06:04

Yeah, well, actually, I think if you really look at the bots are best used where good quality and relevant data is available. Because the whole premise of AI is that you need to feed patterns and data sets for the AI to really learn from it and then be able to interpret real world scenarios by using that learning to extrapolate results. Right.

Jay Ruparel 06:46

Where there is a steady set of data, trends, patterns that can be extrapolated, that's where the bots can best be used. But where there is a fair degree of uncertainty, ambiguity, the level of abstraction of the problem is higher, that's where AI bots would struggle. So clearly that's where you can kind of separate the capabilities of the bots from the human to say if it's a new scenario, if it's a completely new initiative that has no relevant data that you can extrapolate from AI is not going to be useful there. Maybe once it evolves to a stage where you have operationalized it, now you can have AI step in and take over that activity.

Daniel Stillman 07:49

Yeah, we talked about this a little bit in our last conversation. The idea that AI is taking data and trying to extrapolate or learn from that, but it being fundamentally past oriented or past based. There is a limit there. And so I'm wondering how you think about being clear on that limitation for yourself and in the application of this technology.

Jay Ruparel 08:19

Yeah, the beautiful thing about the human mind is that we can think what we are thinking and we can reflect on what we are thinking and that allows us to really not be limited to future envisioning creativity based on past reflections. The bot has this limitations or AI in general has this limitation that it cannot really think about the future in isolation of the past. And that's what is fascinating for me in terms of when understanding human computing interactions is that if there is a bot to bot conversation, that bot to bot conversation. And a human to bot conversation is differentiated by the fact that the bot to bot is all based on just reflection of what they have dealt with in the past. And the moment something new comes up, they can't really envision a new feature out of it. Whereas with humans it's different. So I think that capability that exists, it's something that when a lot of people say will AI rule humans? And this whole we hear about all this Sci-Fi kind of themes about AI taking over the world, I think it's not going to happen for this very reason. I think the way we can think about the future

Jay Ruparel 10:08

is clearly something which is a very powerful capability that only we have and with however, sophistication whatever sophistication you use to build the AI, it will always be limited and can never match that human envisioning capability.

Daniel Stillman 10:30

It's so interesting and I think it's really profound. This is something that I've thought about shameless plug for my own book when I was thinking about this, as we all have been for years. It's like it can free us up to be uniquely human, right? That automation and pulling some of these things off of our plate can free us up to do the things that we are uniquely good at, which is to dream, to be creative. What's interesting, when you were talking about being data and learning focused and more transactional, I definitely know people where they get stuck in that type of conversation where we're looking at the data and we're trying to sort of like look at the near term versus we are dreaming, whereas we're being creative, we're letting conversations flow. And I'm wondering how you and your own work with your team make space for these really deeply human conversations because I think it's actually very easy to get pulled back into maybe a little bit more of a mechanical approach. Even though we're not mechanical, I think we can get pulled into, well, where's the data, where's the analytics? What's next? What's next versus thinking three, five years out? So I'm wondering how you thread that needle because I don't think it's an easy needle to thread.

Jay Ruparel 11:56

Yeah, I think you brought up a fascinating point. It's something that we are constantly thinking about at the workplace is where do you strike the right balance between how much to use AI for your own work? So starting with, for example, we have engineers and we now have AI based coding tools that can basically generate a piece of code, right? And so we have discussed with our engineering team and we have had some debates about should we use some of that capability that the AI throws up for either validating a core or for generating ideas

Jay Ruparel 12:46

not just restricted to the engineering team, even to the marketing team to say, hey, I want to write a blog. Can I use Chat GPT or other generative AI to basically help build that? For example, when someone told me this that you want to give a speech, we have a town hall that we do every month and someone said you want to talk about this? He said I use Chat GPD to just basically write my whole speech that I give to the employees. And I thought, well, let me try that. And across all these different examples, what we have realized is that you can use generative AI, you can use any such AI tool for giving you some ideas to explore with. You could generate some code and look at is this maybe a good way to solve this particular design problem I'm dealing with? Or I can say, okay, I want to talk to employees about this theme. Can you generate help me with some ideas? And because it deals with large data sets, right, it is about someone that is assisting you, scanning the whole range of different articles and books and coming up with themes for you, right? So that's a great help. But then being able to decide what is right or not appropriate for that context, how to use some part of it, what part to use, that is where really I think we need to differentiate ourselves and say that's where the human capabilities come up. So in terms of that human connect. So when I'm actually talking to my employees in a town hall, I would never use a speech that is generated by Chat GPD because it would be cold to me because it's not my own. It may be a great speech written, but it's not my own. So for me, because the way I connect with my employees and I connect with how I can personalize every bit of what I want to say is not something that can ever be replicated with an AI completely. So that is one part of it. The other is just human to human conversations, like how we are talking now and we have discussions over zoom or in person because they're remote employees that we have, we are always looking for how to have conversations beyond using technology tools because in our day to day life. We are already doing too much of it. Right? So we had this classic case of and this happened in my previous organization. Someone had a loss in the family and everyone across the organization was sending like condolence messages whereas they were just on different floors. I mean they could have walked down. Right? And that caught us. We said this cannot be happening, we can't allow for this. I think it's important for organizations and we are consciously working on that is to say how can we have that human to human element still kept alive? And there are so many benefits of that. Having those short conversations near at the coffee station or just chitchat before and after the meeting and the kind of connections you develop is not something that you can do with a bot or using any technology or tools.

Daniel Stillman 17:02

No. So this goes to one of the conversations I wanted us to have, which is around conversational intelligence because we give these bots a certain level of conversational intelligence based on them trying to learn what it is that we do in normal conversations. And then there's us as human beings being really intentional about continuing to expand our own capabilities to connect and to develop relationships and to learn and create meaning with other people. So I'm wondering, I learned a lot in my own research around designing human conversations by seeing how conversational theorists and technologists were trying to understand and model human conversation. So I'm curious if understanding human conversation from a technical perspective has changed how you think about building good human conversations.

Jay Ruparel 18:05

Yeah, no, that's a great question. I would say one of the things we do and that kind of is differentiating us as a company in building these AI solutions is that we record live conversations between humans and the staff at, let's say the drive through and then use those live audio to actually train the AI. Yes, because there are others that for example use synthetic data where you basically imagine the conversations that people will have in ordering food versus us using these live conversations. It helps us really understand the whole variety of ways that people talk for just one use case which is ordering food. Right? So the AI learns from that conversation and builds on that. What is interesting though is that when humans are doing these conversations and they know that there is a bot at the other side, they basically adjust their expectations because now they know that I'm not talking to a real person, I'm talking to a machine. And so the way when we are going to the bank and going to the cashier versus when we go to the ATM, our expectations are very different in terms of what we would ask, what we would do and not do. Similarly, the human expectations are reset just by whether they're talking to a bot or another human. And that kind of changes the whole conversation style, the level of the relationship, the level of compassion, all those elements are completely different. And so when we started our learning from this has been a couple of things. One that there are certain types of conversations that we would never want to replace. There are conversations that are important to happen between a human and human and you shouldn't want to use technology there because although it may give some benefits in the short run in terms of cost savings or efficiency, over the long run, it is actually a deterioration of the whole human to human relationship. Yeah, the other thing is that even in terms of how we design these conversations, we are now looking at can we actually enable humans to just have a better conversation rather than we were looking at the problem as saying how can we replace some of the automated conversations by plugging in the bot? Now we are saying that there are situations where we want the humans to continue having the conversations, but how can we use that augmented intelligence approach where we actually give the humans enough tools so that they can now converse more intelligently? So for example, using voice biometrics you can identify if the person there is a repeat customer at the drive through. Now the AI can use that and say welcome John and would you like to repeat your order? But if we don't want to do that and continue with the human interaction, how about if the drive through staff gets the same intelligence to say hey, this is a repeat customer. By the way, he ordered XYZ last time. And so start with personalizing say hey John, would you like to order the same burger and fries that you ordered last Friday? And what a great human experience that would be. So really looking at this angle of assisting or augmenting the human capability in doing the right kind of conversation, that's.

Daniel Stillman 22:48

Very interesting because you're basically sort of like giving people potentially a field of data. We've talked about this in the past. I use a tool like Grain that transcribes my coaching conversations and summarizes them. And I have a document that I share with my clients where it's there. It's extremely valuable to me to be able to see that high level summary anytime I want to. It's also really interesting to think about this idea of transactional versus I wouldn't say non transactional conversations, maybe more relational conversations. Because I remember when I was first starting to study conversation design from a technical perspective, google talked about this idea of the collaborative theory of conversations, that we each come to a conversation and we try to exchange meaning and act or transact. Based on that conversation, I reached out to you and said hey, would you like to be on this podcast? And we had a conversation about like, well, what does that mean and can I do that? And what is daniel looking for and what am I looking for? And then now here we are. We're acting and transacting based. It's relational, but it's still, on one level, an action that we want an action to happen at the end of a conversation. And one of the things I heard you talk about was the human conversations that we have in the meat space or in relationship to other people inside of the company. It's very easy to get caught in transactionality versus having a conversation in service of the other person, in service of their growth, in terms of their development. And so being really clear on what the goal of a conversation is, is really important because you're right, when we're going into a drive in, we're talking about ordering a sandwich, we're in our car. It is a transactional conversation. But I think it's very hard to remind. I certainly have a hard time remembering that there's value in slowing down. There's value in not having a transaction and not even having a point to the conversation. Like small talk.

Jay Ruparel 25:04

Yeah, absolutely. I'll give you another example. Two weeks back, our HR brought up this someone from our HR team basically said came to me saying, hey, by the way, there is this tool that everyone has started using. What the tool does is that you can create a template of happy birthday emails and you just upload all the employee data to it. And then it would basically just send out a personalized email. And then you could actually personalize it to a great extent to say. But I said, what is the point of me, for example, if I have to use that as the CEO, as someone who for me, that relationship, that wishing someone on their birthday as a personalized conversation means so much to me. That's the last thing I would want to ever automate and have my Bot. I would rather not do it rather than have

Jay Ruparel 26:08

like you said, the drive through could be very transactional, but this is not something I want it to be ever transactional. Right. It is that one day in the year where you really get the opportunity to wish the person you don't want to automate that.

Daniel Stillman 26:23

I think that's beautiful because this brings in the perspective that I see it as. I mean, everything is a spectrum, and in this sense, there's over design or underdesign, but that's just all a perception. I often quote my mother when she was reading my book. She was like, Dangle, I don't always want to design my conversations. And I said, mom, that's a choice. Choosing to not design the conversation means that you're saying, like, I want to do it myself in my own way. That is a design. I don't want it automated. I don't want it scripted. I want it to be new every time. And I'm curious how you think about the structures that you do like that you do use as a CEO to manage all the complex conversations that you have. Because it's not just I presume winging it every day with your leadership team, with your other key stakeholders. I'm curious how you think about what is the minimum viable structure, what Jay's conversational intelligence guidelines are for, how you think about designing some of those conversations.

Jay Ruparel 27:39

Yeah, this may be like maybe a secret recipe that you're asking me to share, but I'm happy to do that in the sense that and this is something I've learned from some of my mentors as well. One of the things I do is even for specific meetings that I have, I would basically plan just taking a few minutes in advance to think through what is it that I want to convey.

Jay Ruparel 28:21

The objective of the conversation is something that I start with to say and I try to keep it to as minimum as possible and having that piece of communication made very clear. So, for example, if I'm going to have a 30 minutes meeting with a group of four or five members, but my core objective from that meeting is to communicate that one or two things, right? I will basically either write it down or phrase that in my mind to say these are the two most important things I want to convey through the meeting. And then based on the context and the nature of participants, I would then basically decide the way I would like to convey that. Sometimes it could be direct, sometimes it could be through some examples or citing some data to say why that needs to be done. So it starts with the objective, it factors in the context and the type of participants, and then it comes to how it needs to be delivered. And in this, one of the things that I pay special emphasis to is when I'm looking at the nature of participants, I'm not only looking at for each individual because sometimes you're dealing with people that you may not know so much about, right? When it is internal teams, usually I understand what type of communication style will lead to the right impact that I want. When it comes to others, clients, other stakeholders whom I don't know that much, I usually take the first few minutes, maybe even the first 20%, 30% of the meeting, to really understand them. So there will be discussions that we will have which are not really related directly to the topic, but which will just help me understand what is the effective way for me to communicate. But in my mind, I'm clear that I'm going to discover that in the meeting and then use that style which will create the right impact, that little bit of homework. So one of the things this is something I learned from a mentor is I have on my calendar actually scheduled, I have what I called a me time, which is in the morning. So that me time is really from eight to 09:00 A.m., I don't set any other meetings because my calendar is blocked for that me time. And that is the time when, for all my meetings through the day, I'm doing this objective setting. What do I want to achieve, how do I do it? All of that is being planned and other activities are being planned as well.

Daniel Stillman 31:40

It's funny, you answered so many questions. There's so many layers there. And I want to peel a little bit of that onion because blocking out that me time is so important, like, absolutely essential, because if you don't have that preparation time, you're going in a lot more blind unclear about what's going on. And I imagine you've seen the impact of the me time, and so you do not. What would it take for you to skimp on your me time? Would you? Have you I mean, I'm sure we.

Jay Ruparel 32:17

All have, but I try not to because it's a big deal. Now, I have seen the benefits of that. I would not do it unless it is like something which is super urgent, unexpected, coming up. Yeah, that's the sacred time I have for myself. I will never compromise on that.

Daniel Stillman 32:40

And that's to really look at your day and say for each of these conversations, what is my goal or objective, what do I know about the context and what do I feel like? Is my tailored approach? Is it direct? Is it more example or data driven? Do you do that in a sort of structured way or do you feel like it's a little bit more intuitive now that you've been doing it for some time?

Jay Ruparel 33:07

Yeah, I started doing it in a very structured fashion. So I would actually look at every meeting and then I would actually make bullet points in my notes app to say, and I would have that in front of me on my iPad when I'm in the meeting. So I used to do it that way, but it has become less of structure, more now it's more intuitive, but I need to think through that process. And one of the things that I've also learned is that and this might sound

Jay Ruparel 33:49

it might sound bit OD. It sounded OD to me when someone told me this. And I started practicing. I actually look at, I imagine, the impact that I want to get out of the meeting and I just think about it for like 15, 30 seconds. For example, if the impact of the meeting that I want to have is we are behind schedule, let's make sure that we put in all our efforts to get this done by end of the week. Right. And that's what I want the team to agree to. I would basically imagine that situation where someone is saying that at the conclusion of the meeting. And that kind of allows me to also reframe some of the way I was thinking about that meeting. Right. To achieve that. Once you visualize the end result, you have a better understanding of how it will play out and then it just gives you that energy to then make it happen.

Daniel Stillman 35:11

And this goes back to what we were talking about, about AI being past oriented. Visualizing an ideal future is your job. Yeah. I don't think anybody else can or anything else can replace that job for you.

Jay Ruparel 35:31

Absolutely. Yeah. And because that is so individual to you, the way you visualize an outcome is so individual to you. There is no one prompting you like you would do to a Chat GPT of what that outcome has to be. Absolutely. I think you've connected the dots very well. In fact, there was a fascinating article on is ChatGPT a Reflection of Humans? Or something around that title. And basically what it threw some very interesting observations about. Ultimately, when you are interacting with an AI or a ChatGPT, it is basically reflecting on

Jay Ruparel 36:22

what prompts you are giving. Right. A lot of times, yes, you get some bits and pieces of knowledge there, but ultimately your prompts really dictate what you get out of it and also what you interpret out of what you've got. Right. So it's really your own reflection. Right. And some people like that reflection, some people don't like that reflection. But it's like a mirror. I think the article was, is it a mirror to the human soul? And I thought it was a fascinating article.

Daniel Stillman 36:55

Well, you bring up a really valid point, which is like the questions we ask dictate the quality of the answers we get.

Jay Ruparel 37:02

Right.

Daniel Stillman 37:02

I'm curious how you think about because that's an aspect of conversational intelligence. I think often we think about conversational intelligence as what I say. It's also how I listen, but it's also how we ask. And I'm curious in terms of trying to get the best out of your team, which is, I think such a fundamental role of the CEO, presumably everyone reports to you and they are better because of it. I'm curious how you think about how you ask, how you elicit and how you reflect because you're not a bot, but we're still doing those same components that a bot is doing. What's the operating system of your CEO bot when you're doing those CEO level conversations?

Jay Ruparel 37:52

Yeah. I'll give you a real example. Just last week we had our meeting of the product team and one of the things we asked everyone to do as a pre work was describe our products in five sentences. But each of those has to be questions. So don't say our product does this ask a certain question and that should describe the product. And the reason why this is important is that, like you said, it is all about what questions you ask. In this new AI driven world, the answers are out there, but the questions are really important. And that's why this whole subject. Of prompt engineering as they're calling it, it's going to get more and more important. So I think in the organizational context also, the way I feel is that we have kind of given up a little bit on curiosity as a human trait. And I think humans were far more curious earlier than and I think somehow that kind of has been waning and it kind of now has to come back to the fore, which is basically getting answers is easy. That's the way I think the future is going to be. You can ask a bunch of people and you'll get answers, but what questions to ask, how to ask them, what context to keep in mind, how to make the questions have the right language, the right conversation style. This is very important. That's what we want to and we're doing like we did this in this product meeting, want to create ways that we can facilitate employees to really ask questions. And even in meetings it's not necessary to end with answers, but just to end a meeting with lot of floating questions to say, oh, we spend 30 minutes and we came up with fascinating eight questions. That's a great outcome of a meeting, right? It doesn't matter whether you had the answers or not, but we ask great questions and that will create a very healthy organization in terms of the quality of interactions you can have.

Daniel Stillman 40:31

I think that's a very interesting value to apply to conversations because somebody could easily say at the end of 30 minutes, I want to have a clear decision or a yes or a no or a next action. And that's one way to design a meeting which is just a group conversation. But it's really interesting to hear you talk about valuing, getting to a small set of interesting questions at the end of that conversation because that will fuel the next valuable conversation, presumably.

Jay Ruparel 41:11

Yeah, absolutely. I completely agree with that and I think the value that we will start seeing in humans and as we employ professionals is going to be in that is going to be even in interviews when we are interviewing people, it was always about asking questions and seeing who has the smartest answers. I think we are already seeing that change and it will be seen even more is what are the questions that you're getting from the candidate and are those interesting, relevant, meaningful questions? Right, yeah,

Jay Ruparel 41:58

I'm very excited about how I think the true human capabilities in terms of creativity, curiosity, compassion, ability to envision the future, all of this could be augmented even better with what's happening with AI.

Daniel Stillman 42:23

It's so interesting, and I'm really glad we covered a lot of what I was hoping to from, and I said, this is one of the reasons why I wanted to have you on is that conversational intelligence is such an important topic, and you're one of the sort of few people, I think, that can speak to it from both sides of it. Technical and emulation of simulation of conversational intelligence and also making choices and optimizing for human conversational intelligence. And so I feel like we've covered a lot of what I was hoping we should cover. But I'm curious if there's anything we have not talked about that you think we should have touched on because we still have a couple of moments.

Jay Ruparel 43:07

Yeah, I think we have covered some really good points. I think I do want to mention about. One thing that is going to be interesting as it plays over the next few years is how we understand the ethics governing some of these AI based conversations and interactions. Because the regulation has still to catch up and right now it's kind of freewheeling for all the technology companies and they're using AI the way they want. But there are some concerns around to what extent you should use AI and where do you cross the boundary in terms of ethics and privacy and other compliances.

Daniel Stillman 44:05

It's a huge topic. I mean, how should we even be framing the conversation? How should we be designing that conversation about ethics? Like you said, law is always going to be trailing well behind technology. How are you thinking about it.

Jay Ruparel 44:27

Obviously, when it comes to human to human conversation, because there is a human at the other end that has norms around privacy and ethics, you are automatically framing conversations, being careful with the bot and the kind of access to data that they have. I think it is about really reimagining what those boundaries could be. And we had a couple of instances where conversations came up about can we understand the ethnicity of the person of the customer and customize the offering around that now? Well, the AI can maybe do that, but is it right to do that? Those are the kind of conversations so I think there's a lot that needs to be done in terms of just understanding the implications of AI. And I think the term that I keep hearing about is responsible. AI is how can you act responsibly towards the society, the environment and just make sure that while the technology has a lot to offer, we tread on that path carefully without violating anyone's privacy and any ethical norms.

Daniel Stillman 46:06

Basically, privacy is a really interesting aspect of the conversation and also how it's implemented and potential discrimination is an interesting lens. There's another one that I'm curious how you think about the AI supply chain, because you mentioned and I've read about this before, we're training the AI on humans who then potentially don't do that job anymore or do that job less. And I don't think you necessarily have control over how a company brings this into their brand architecture and into their employment habits. But I remember reading a story about how, like, you know, we've got a sales team of 100 and we basically train the customer service bot on the top 10% and then the bottom third of the sales force then becomes much more effective. The top 10% is still great. They don't really need the AI that they've trained. They aren't getting bonuses anymore because of performance. If that's how they were getting compensated, the compensation structure changes. And now the whole rest of the company is doing better because of the people who were doing the best in the first round. I see these the AI is learning from us often and then what happens? And I think that's a part of the ethics that people don't often think about. I'm wondering how you noodle around that.

Jay Ruparel 47:47

Yeah, no, I think it's a really good point because we often think about AI in terms of replacing specific activities or jobs or taking that over, but in terms of just being able to learn from existing workforce and then being able to do that and pushing the envelope really for everyone in the workforce. So it could be obviously there are positive aspects to it in the sense that you could actually have a lot of complicity that may be existing in certain parts of the organization now. Everyone has to kind of reinvent the way they deliver value because the same thing that they were doing is probably some of those or most of those can be done by the AI. So now you need to look at higher value added activities. But then the other side is also how you can as an organization become there's always this challenge about knowledge and expertise residing in individuals versus the organization. An organization is always trying to look at what are the ways to extract that knowledge and expertise so that the organization becomes less dependent on specific individual talent. I think there are both sides to this, but there's a lot of work being the people involved in broad the future of work and how you'll be working. Instead of having human workers in a typical office, you'll be having think of it as almost some humans, some AI bots and you're all working together to achieve the task. I clearly can see that that's the future that will be emerging.

Daniel Stillman 49:59

I think if we're going to talk about ethical AI, then it's a broader conversation well outside of our scope today in terms of what ethical capitalism looks like. Because in an individual company, you're absolutely right. It's optimized to learn as much as possible as an organization and to not rely on the knowledge or expertise of one individual because the goal is to deliver reliably a service or experience regardless of that person is sick or leaves someplace else. So that incentive structure is there. So I think this is a much bigger conversation. I'm glad we touched on some of this. It's an ongoing conversation I think everyone needs to be having.

Jay Ruparel 50:48

Absolutely.

Daniel Stillman 50:49

But I know we're at time. Time goes so fast. Jay, where should people go to learn more about all things Jay and all things Voiceplug. Where should we point them to on the Internet if they want to stay in touch or stay part of the conversation with you guys.

Jay Ruparel 51:08

Yeah. Voiceplug is at voiceplug. AI. And then you can always search Voiceplug on LinkedIn and Twitter. We have some good posts that we do blogs on LinkedIn. And then of course, you can reach me on LinkedIn, just J Ruparel and I'll be happy to connect if there are any questions, any thoughts, comments. Happy to do some follow up conversations as well.

Daniel Stillman 51:38

Thank you so much. And I'll put links to both of those in the show notes. I am so grateful we had this conversation. It was very far ranging. I'm glad we touched on some thorny topics and I really appreciate your openness and your honesty.

Jay Ruparel 51:53

Oh, I really enjoyed the conversation. I think you asked some really nice questions. You brought in some great points. I didn't know where time flew by. So this is a great conversation. Appreciate you having me on the show.

Daniel Stillman 52:07

Thank you so much, brother. Well, the feeling's mutual. We will call scene. Thank you.

Jay Ruparel 52:14

Thank you.

Designing Conversations to Unlock Strategic Foresight and Innovation with Kevin Bethune

I’m excited to share my conversation with Kevin Bethune, a multidisciplinary design executive, entrepreneur, best-selling author and keynote speaker based in Redondo Beach, California. He’s been a VP of Strategic design at BCG Digital, A global process product manager at Nike and a Nuclear Engineer at Westinghouse. He currently leads his own firm, https://dreamsdesignandlife.com/

One of his key ideas is “Open your aperture.” -ie, shifting the lens that you are looking at a problem from or through. Design and Design Thinking has so many tools to help us do just that, and find creative approaches to our biggest challenges.

In our conversation, we discussed the importance of embracing creative approaches (since our habitual approaches most likely can’t solve them!) and the need for bold leadership to optimize for curiosity and creativity - because going with business as usual is usually a lot easier than spending time on curiosity.

It takes a willingness to slow down to optimize for curiosity in a business environment that is often so focused on quarterly capitalism.

We also highlight the lack of diversity in design and innovation, particularly in black representation, and the cognitive dissonance of claiming to serve certain communities without actually representing them - an unresolved critique of many innovation firms.

The S-Curve and the Cone of Possibility

Kevin’s book, Reimagining Design: Unlocking Strategic Innovation, is CHOCK A BLOCK with diagrams (and I love diagrams!) that will stretch your thinking, but we spent some time on one diagram in particular that combines two classic models of thinking: The cone of possibility and the s-curve.

The Cone of possibility is a cone on its side, with the tip at the present, and the sides of the cone stretching out like rays of sunshine to the right. The rays represent possible futures along the timeline. There are many versions of this diagram online. Kevin’s version calls the center of the cone the “most likely” or projected future. The cone of possibility invites us to consider widening edges - future scenarios that are plausible and even impossible or preposterous futures, not just the projected or ideal future

Opening our aperture to consider multiple possible futures means that our plans can be more resilient, adaptable and even antifragile.

The S-curve is a visual representation of one of my favorite Shakespeare Sonnets. #15:

When I consider everything that grows
Holds in perfection but a little moment,
That this huge stage presenteth nought but shows
Whereon the stars in secret influence comment;
When I perceive that men as plants increase,
Cheered and check'd even by the selfsame sky,
Vaunt in their youthful sap, at height decrease,
And wear their brave state out of memory;

Things are born (or emerge), they grow, mature and then fade away. Kevin’s version of the S-curve includes more detail:

  1. Emergence

  2. A dip - the trough of disillusionment

  3. A hyper-growth phase that slows into..

  4. Maturity and then…

  5. Decline, or retirement.

Kevin overlays the cone of possibility with a set of cascading s-curves, representing a host of possible trends rising and cresting as we look out into the possible futures.

As Kevin describes this diagram in our conversation, his hands are making waves of opening and closing, diverging and converging. That's what he’s seeing when he looks along the cone of possibility: all of these different trends, multiple pathways. It’s this complex, undulating space that he tries to illustrate for the teams that he works with to help them see a bigger aperture to think inside of.

These diagrams, these mental models, help redesign the conversation about strategy and innovation. We’re not designing for a single, simple, ideal future. We’re looking out at a complex landscape with multiple possible twists and turns. That is how you unlock strategic innovation - step back, widen the aperture and change the conversation.

In short - creative visualization facilitates dialogue and widens perspectives.

More About Kevin

https://www.linkedin.com/in/kevinbethune/

https://dreamsdesignandlife.com/

Kevin Bethune is the Founder & Chief Creative Officer of dreams • design + life, a "think tank" that delivers design & innovation services using a human-centered approach. Kevin's background spans engineering, business and design in equal proportion over his 25 year career, positioning him to help brands deliver meaningful innovations to enrich people's lives.

His work represents creative problem-solving that brings multidisciplinary teams together to see the future through an open aperture, and a deep industrial design approach to inform and influence desirable, feasible and business-viable design outcomes.

Kevin also serves as a Board Trustee for ArtCenter College of Design and the Board Chair for the Design Management Institute (DMI).

AI Key Moments

(0:19) - Kevin discusses the challenges of implementing design thinking in business environments, including a bias towards formulaic approaches and a lack of collaboration across disciplines

(4:09) - Kevin suggests that it takes bold leadership and a willingness to slow down to optimize for curiosity and creativity in business

(10:28) - Kevin reflects on how his book has served as a mirror for others and helped them see themselves in his story, as well as how it encourages creative courage and confidence to experiment on curiosities and become a source of influential change within organizations

(13:58) - Kevin explains how opening the aperture and considering a wider range of perspectives can enrich team conversations and inform them with more diverse perspectives

(15:05) - Daniel and Kevin discuss various diagrams in the book related to strategic foresight, including the cone of possibility and S curves of emergence and saturation

(20:02) - Daniel and Kevin discuss the importance of requisite diversity in solving complex challenges and the lack of representation in design and innovation industries

(23:16) - Daniel asks about where conversation design fits into a diagram in Kevin’s book and they discuss the power of visualization in facilitating dialogue and widening perspectives.

(40:50) Kevin emphasizes the importance of tapping into the value criteria of stakeholders and creating new avenues of utility for them.

(43:05) - Kevin suggests being subversive with a good heart and showing what design can bring to help the business, while also considering the implications of every business or design decision.He also talks about value creation and mapping value criteria across stakeholders, emphasizing the need to anticipate where value will be and show up for people in new and novel ways

Full AI Transcript

Daniel Stillman

With that, Kevin, I will officially welcome you to the Conversation Factory. Welcome aboard. Thanks for making the time.

Kevin Bethune

No, thank you for having me. Daniel.

Daniel Stillman

So why does design need reimagining? Can we start right there in the center?

Kevin Bethune

Yes. What I can say is that in my business, this experience is, unfortunately, there still lingers a glass ceiling of ambiguity. It's probably the best way I could describe in terms of how the larger business landscape understands design, or even design thinking, for that matter.

Daniel Stillman

Yes.

Kevin Bethune

And the differences in between. I think it's just time to sort of revisit where are these approaches sort of coming from, and how do organizations think about potentially wiring themselves to really embrace these philosophies and these capabilities that design could bring to the table?

Daniel Stillman

I love that phrase, wiring themselves to embrace that. What is the glass ceiling of ambiguity, and how should organizations be rewiring themselves to embrace the power of design and design thinking? Which are we allowed to talk about design? I mean, it's like it's gone in and out of fashion so many times. So I appreciate you bringing it back into the conversation. What needs to shift?

Kevin Bethune

There's a couple of things that come to mind. Unfortunately. I think in most business environments, I think a lot of times, we feel this pressure to derisk our approaches, our methods, how we create product. There's just a general derisking. And with that, also, the speed of the clock only seems to be getting faster, thanks to digital. So sometimes I think there's an unfortunate bias toward looking at a methodology. And if a business community is looking at design thinking for the first time, there might be just a bias to want to march through the process in a very formulaic manner.

Daniel Stillman

Yeah.

Kevin Bethune

And those who are perhaps more familiar with creative approaches, creative processes, understand the nonlinearities that one must take to understand how to react to the information that you have available to make the next step forward. And it's very nonlinear. There's a lot of loopbacks, a lot of pivots, a lot of wayfinding that needs to happen that perhaps the frameworks that the business community might read about don't necessarily get into. And the framework can easily fall down in the face of real business complexity. So that's one thing. And then secondly, in a good way, I think design thinking has brokered a conversation to bring different disciplines to the table to at least begin to entertain their creative process. I think that's good. But in reality, I think especially the larger organizations get the bandwidth to actually collaborate, and problem solve across disciplines is still very much the exception. It's not the general rule.

Daniel Stillman

Yeah.

Kevin Bethune

There's not a lot of time to collaborate. And I still find that with organizations big and small.

Daniel Stillman

Yeah, you mentioned this. So when we were talking about what we wanted to talk about, the ability, the interest, optimizing for curiosity, creativity, and having an open aperture is really challenging because most many businesses are in the business of optimization and maximization and forward moving. What does it take for business to be willing to step back and have that creative open aperture?

Kevin Bethune

Well, it does take a healthy dose of courage and believers in the power of what these creative approaches could offer. And not just I'm not talking through the lens of just design any discipline. I think it takes bold leadership to empower the different disciplines within their watch, give them the space. And it's something like the old adage around going slow to go fast later. If we sort of slow down to appreciate what each discipline can bring to the table. I don't think it happens over the postit note dance or the whiteboarding. Each discipline has their own depth of expertise and their own strengths that we need to make room for. And if we do that thoughtfully and allow teams to sort of norm and find their optimal chemistry, which isn't necessarily equated to speed all the time, true magic can happen. And once we get to epiphanies that are actually more meaningful to the stakeholders that we're serving, then we can go fast later and shift the stuff that's the most relevant. That's going to hit the need right on the head.

Daniel Stillman

Yeah. Can you talk a little bit about if we take a step back and talk about your journey? Because the earlier part of the book is there's too much we can't do it justice here. I think your story is worth reading about. You've had a crazy journey. Not everyone has had the opportunity to work on nuclear reactors and sneakers. Not everybody has built an entire new business for a global agency. Right. So what made you want to finally share it and undergo because writing a book is a pain in the ass. Just acknowledge that writing a book is a journey. What made you want to really undergo the travails of book writing to share your story?

Kevin Bethune 06:09

No, I appreciate that and yes, it was a pain in the ass.

Daniel Stillman

Anybody out there thinking about writing a book, think twice. Ask yourself, how long do I want to deal with this pain? And then how long do I want to be talking about this thing?

Kevin Bethune

And I do have to shout out the MIT press. They've been wonderful sages to get me through the process. But as you mean, it's been a unique journey of multidisciplinary leaps and I could say that now, hindsight being 2020. And I can say also that it wasn't surely easy like as I started my career as a nuclear engineer working on reactor mechanical systems to wanting to garner the language of business just by sheer fact of a natural curiosity to want to understand the bigger picture around. The engineering work led to an MBA came into Nike, which created an environment that offered not just the strategic aspects and technical stuff, but that was the first time I was in an environment that had actual formal creativity embodied in the organization as well. And so that really opened my eyes to the power of design and how it could plug into technical and business concerns. Yeah, and I'm thankful that the Nike environment afforded me some runaway to begin to cut my teeth on Nike product and also start to entertain some early forays and quick wins on design and ended up going back to school for design to really solidify that creative foundation. And that was a big gamble when I thought I was done with school to go back to school for more education. But it was a career bet to really solidify my career positioning at the intersections of these disciplines because I think I honestly believe the future is going to require more multidisciplinary collaboration and conversations to breed the next generation of innovations that will be required to meet the needs of the future. And yes, that's where I wanted to plant my flag. And as I mentioned, it wasn't difficult, it surely wasn't welcome traversing these different disciplines. And I think based on recent experience navigating the environment of BCG in recent chapters where we had to stand up new capabilities that were new to BCG, new to BCG's clientele. I did walk away from BCG with this appreciation for the intellectual curiosity that was a huge part of their culture. This notion of eminence, of sharing what you've learned and the act of sharing through written word articles or keynote speaking at industry conferences, that act of freeing up in communities, that knowledge. You open your mind up to embrace new information from those communities and you can bring that back into your work. And so I think that immersion in BCG culture sort of planted the early seeds that perhaps a book could be written based on what I had to help stand up. But interestingly enough, the timing of when I started the writing process was at the very start of the COVID-19 pandemic. And so, surprisingly, the book went to a very personal place, more so than what I initially expected when I entertained the project with MIT Press.

Daniel Stillman

It was a very reflective time, having all that weird spaciousness in some

Daniel Stillman

you know, you talked about a book being I love this word eminence. And what you sort of sketched out is a classic feedback loop of the way I would describe a book should be. We want it to be a conversation. You're taking all the conversations you've had in your life and turning it into a new conversation. You want people to read it, you want to engage in those dialogues. You want to share ideas from that book and learn. And it creates a new cycle of learning. What's that been like for you now that it's been out for a while now? Is it creating the conversation you were hoping it would start?

Kevin Bethune

Yeah, it's been a year since it's been out. And I'm very thankful for what I've learned over that year of just understanding how it resonates with folks. And I think the consistent thread of feedback was that it served as a mirror of sorts for other people to say through someone's story like take my name out of it. But in diving into someone's story that's had this weird journey, they begin to see a little bit of themselves in that and their own journey. And I think the book helps them open their aperture to understand what they could potentially do, how they could potentially garner more creative courage and confidence to experiment on their curiosities and then taking it a step further. It's also helped them see how they might become a source of more influential change within the organizations and the teams that they're tasked to shepherd.

Daniel Stillman

Yeah, that's exciting. For those of you there's no video of this, but Kevin's smiling. I don't know if you may be able to hear it in his that's that's given you some joy. Yes, I think that's really awesome. What are some of your favorite diagrams in the book? Because it is chalk, a block of diagrams. I'm a big fan of a diagram. Clearly you're a bit of a framework nerd yourself, sir.

Kevin Bethune

Clearly. I'm happy that I got a chance to sketch all the figures that you see in the book. I'm a very visual communicator that's I guess why, you know, my editor was like, you need to sketch all your figures. But I do gravitate to the lens a lot. There's a figure of a looking glass staring at the distant time horizon.

Daniel Stillman

Yes.

Kevin Bethune

And that lens is all about just it's a constant reinforcement I use with all of the collaborations that I'm involved in all around encouraging the teams that I'm a part of to open our aperture. This idea of opening the aperture to regardless of whatever the brief is, whatever the immediate business concern is, we can all stand to take a step back and look at the future through a looking glass. That forces us to really lean into our multidisciplinary collaboration. And if we do that and really leverage the diversity from that, we can populate that lens with all kinds of data points, inspirations, observations, spanning stakeholder needs to business paradigms to trends and exemplars and not taking what is happening in the business world today or the present consensus of how things are supposed to behave as a given.

Daniel Stillman

Yes.

Kevin Bethune

And by opening our aperture, we can interrogate everything.

Daniel Stillman

Yeah. So let's talk about that because that's in chapter four and the lens. You talk about industry, people, trends, exemplars. This is about future strategic foresight. Right. So let's talk about opening up the aperture and what that means to you because again, this is about stepping back and this is about being curious about more elements of the conversation than just what is the thing we're trying to make now? How do we create immediate value? It's stepping back and looking at the big picture. What's important about that to you? And how can we leverage this diagram, this beautiful, starry eyed aperture that you've created?

Kevin Bethune

I think it's a helpful visual to understand, like whatever we're working on in the short term, if we're not tracking at least an appreciation for what's happening across the landscape, across the continuum of time, across not just what's most likely, like right in front of us as a most likely future, but considering dynamics that maybe force us to diverge and think about scenarios beyond that most likely future. If we cast that net wider, we're basically giving our teams a much richer conversation. We're informing the table with a much more enriched and diverse set of perspectives yes. Than what they might have had or they might have had limited if we were to just attack the brief that's in front of us.

Daniel Stillman

Yeah. You're also kind of implicating another diagram in that chapter around sort of the cone of possibility diagram, which I think is a really important one.

Kevin Bethune

Absolutely.

Daniel Stillman

Can you hold those two intention for me when it comes to strategic foresight? And then there's a third one, which I really loved, where it's just a bunch of S curves of emergence and saturation. That was a pretty trippy diagram. That's what you look at when you see the world. That's what Kevin is seeing. It's a cone of possibility and endless S curves of growth and renewal.

Kevin Bethune

Yeah. This is sort of a weird dive into my head in terms of the visualization, because in my mind, it's one visual. Like, if I look through the looking glass at the distant time horizon, that's your lens. But if I turn it sideways, you have your cone of possibility.

Daniel Stillman

Whoa. Oh, I might have missed that. That's looking at the cone of possibility head on.

Kevin Bethune

Absolutely.

Daniel Stillman

Wow.

Kevin Bethune

And as we interrogate how forces of change are commingling across that horizon or through the different parts of that cone over time, trends will sort of EB and flow. Innovation that are making traction in the market will ebb and flow. This idea of the S curve, it's like every new innovation is going to go through a process of emergence. There might be some initial disillusionment in terms of the market's appetite for that, as we well have experienced, and then someone figures it out, and eventually we have some scale, and eventually that will need to be matured for something else that comes along to replace it. So this ebb and flow, this intertwining mix of trends and the wake and the decline and maturity, all those things, we sort of have the opportunity to map, do our best to map and illustrate for teams to figure out what scenarios across our future time horizon might we anticipate to better position our organization for success.

Daniel Stillman

Yeah. Again, your hands are just in this. We're making this wave of opening and closing, diverging and converging. And that's what you're seeing when you're looking along that cone of possibility, all of these different trends, and you try to illustrate that for the teams that you work with to help them see what you see. There are so many layers I want to peel on this onion, one that I think would be really important and I would be highly remiss if I didn't bring it up, is diversity. You are a man of color. You talk about this a fair amount in your book, and I feel like there is a conversation that needs to happen more about what diversity really means in these types of transformation conversations. I don't even know where I'll just be honest with you sometimes I don't like to bring it in unless you bring it up explicitly, indirectly, because as far as I'm concerned, your ideas stand alone, and I don't want to racialize them and I don't want to racialize you and your perspective in total transparency. But you are a man of color and you talk about it in your book, and I think it's really important to talk about what diversity means in all of its layers and the conversations you want more people to be having about race after having read your book a lot.

Kevin Bethune

No, I do appreciate that and I do appreciate the safe space that you're creating to have this conversation. It is a very important one. I think it goes the other way as well in that I'm very careful when I engage people around the topics that I bring in the book to say that I can only speak for me. Yes, I am a black African American male that has navigated some really weird multidisciplinary leaps. And so I do understand what marginalization feels like and reflecting on some of the rooms that I've navigated before. At the same time, I also understand as a male, as a tall male, navigating corporate America. And the presence that my presence can embody in a room might be different than someone else who doesn't have the privilege of what certain business communities might feel. When I walk in the room versus I, especially as a male in corporate America, I understand what privilege feels like. And given the benefit of the doubt based on my stature and my voice compared to someone else, so I can only speak for me. And thankfully, we all get to navigate a world that is this beautiful tapestry of intersectionalities and diversity from every slice of the imagination. But unfortunately, when we speak of our experiences navigating a world that is the way it is by design, who's at the table absolutely matters.

Daniel Stillman

Yes.

Kevin Bethune

And unfortunately, in many of the world class studios and innovation centers and brands, some that I've navigated, some that I've encountered, whether it was through recruiting conversations, I look into those organizations and they don't mirror the beautiful tapestry that is the world. No, especially in design and innovation. Black representation is 1% to 3%, depending on the discipline you're looking at. And they might be claiming to serve an urban demographic that might be half black.

Daniel Stillman

Yeah.

Kevin Bethune

The cognitive dissonance is real.

Daniel Stillman

Yes. The Oscars are so white design is also so white. And what you're highlighting, which is really important, is that there's this concept of requisite diversity in conversation design and complexity theory that if you're going to solve a challenge that's complex, you need to have a group of people that is at least as complex as the challenge they're trying to solve. And I think trying to offer products for a community that you do not represent or relate to in an authentic way is problematic, to say the least. And so you talk about multidisciplinary conversations and the marginalization. That's so easy to have happen. We need to be including people. We people need to be included. Everyone needs to be included in the conversation. That is a really challenging thing to navigate because this idea of inclusion also has the concept of positionality in it. Who is including who?

Kevin Bethune

It sure does. And even the best intentioned practitioners may not realize the harm that they might be complicit with regard to their work. Because representation in the teams is one thing, but what process are they following? That process might have been wired by some limited few in places of power and prestige that have informed the pedagogy in the first place.

Daniel Stillman

Yes.

Kevin Bethune

And many times what's frustrating is there's a lot of quote unquote, world class studios that will design for certain communities they claim to be designing for. But design for is problematic.

Daniel Stillman

Yes.

Kevin Bethune

And you take it a step further, design with becomes the next answer, quote unquote. Like, of course we should co create with our stakeholders and be in there with them and using them as an equal thought partner. But even that, I would argue, is not enough.

Daniel Stillman

Yes.

Kevin Bethune

To your earlier point, why don't we just ensure that our teams are representative, where we actually have representative teammates that come from those communities that can actually form authentic inroads into those communities.

Daniel Stillman

Yes. So there's so many layers there and that's a whole conversation. One of my favorite diagrams in your book is the one around design as concept creation to product creation and execution versus strategic. It's a sort of two by two space. And in the sort of the upper left hand corner of concept creation and strategic design, which we've talked a little bit about foresight design. And on the lower right, I guess you'd say, is motion design. Industrial design is kind of in the middle. Where my heritage? Where is conversation design and gathering what I would call conversation design, which other people might call gathering design. Kind of what we're talking about now. The ability to create multidisciplinary inclusive, non marginalizing processes, gatherings, conversations by which we create things that create more justice. What is that type of design and where does that go on this diagram? Because I feel like it's missing.

Kevin Bethune

No, you are very correct in that it's missing. And I appreciate the words that you're using because especially in today's climate, these are paradigms that are absolutely important. They're also being interrogated with, like, does a human being do that or is the AI engine with the prompts and the conversations with AI?

Daniel Stillman

Yes.

Kevin Bethune

And the speed of the digital clock getting even faster. These are absolutely important. So, yeah, this is an opportunity to even break the visual that I created for this book to expand it. And it's almost like if you take the strategic design corner of the image, this should blow out even further to include the elements that you're describing.

Daniel Stillman

Because I imagine that you are a skilled gatherer. When I looked at all these strategic diagrams, you have so many wonderful two by twos. Of course, you have

Daniel Stillman

vertical versus horizontal innovation, which I loved. I haven't seen that one in a long time, and I still have a hard time really grocking it, whereas you've lived it for years. And I know that you use these to facilitate dialogue. And so I'm wondering if you can talk about what types of conversations you really love to have and how you use all these visuals to facilitate the kinds of conversations you want to have with the companies and teams that you enjoy working with.

Kevin Bethune

I appreciate the question because it makes me reflect that there's been a lot of moments of truth where creative problem solving manifested in very unforeseen ways. And many times, especially over the last 1015 years of my career, there may have been an acute business need, a brief or whatever task that was in front of us. But if there was a moment to leverage my newfound creative skills, many times those stakeholders in the room didn't necessarily know what to ask for or know what to even expect from me beyond the requirements of the brief. And there were moments of truth where there was a brewing connection of dots in my mind that at least spawned the conviction to get out of the chair and walk over to the whiteboard with a sharpie or a whiteboarding marker and visualize what I believe the conversation was provoking. And just by putting a visual on the whiteboard. And granted, I never was your alpha extroverted person or leader in the room. I'm very introspective, very introverted. But there was enough dot connections in my mind that said, you know what, you need to get out of the chair and contribute, and here's a way that you can. So I walk over, I put a grounding visual on the whiteboard, and as much as people are convincing over the conversation, they could look at the visual. And I just felt that power of the visual recentering or reframing or reimagining the course of discussion. And then when they were there, when I had their attention there. And again, this is all about team cohesion around that visual. It gave me a doorway to contribute verbally on top of the visual as well. And so that's been the experience in many instances lately, in that there's an initial ask, but there's always an opportunity to open the aperture. And thanks to the power of visualization, I can use these frameworks, these vehicles, to facilitate a widening of inputs and information and diversity of a perspective that can inform where we're going.

Daniel Stillman

Yeah, the power of a visual to ground a conversation as what are they called, chaotic attractors, because conversations can go everywhere. But when you draw two by two, it really does frame the conversation to say, hey, I know you're asking for this type of innovation or this type of transformation. There's also this other quadrant, this other scenario. How are we designing for this? And so I think that's one of the powers of the two x two scenario planning diagram where you were like, we're talking about this future, but this other future is possible and this future and this future is possible. And what is our optionality for each one of these quadrants? It really does help people zoom out.

Kevin Bethune

Absolutely.

Daniel Stillman

Can you talk more about what it feels like to do that? As I don't identify as an introvert, I think we're all ambiverts. We all live on a spectrum of introversion and extroversion. And so I'm really curious what it feels like, what it's felt like for you to take up the pen and to lead the conversation through providing visuals, with providing a framework, with getting layering more contribution on top of that, what does that feel like in that moment to step into the circle that way?

Kevin Bethune

It definitely was let me just start over.

Daniel Stillman

Sorry.

Kevin Bethune

I can say that it felt magical in the moments. And the other side of that coin of magic was definitely the fear of making a misstep, making a very visible misstep that was out of my character. But I think in the lead up to the last second half of my career, I do remember feeling the frustration of being that introvert in the room and feeling all the inhibitions of speaking up when those convictions were. Bubbling when I was able to naturally connect the dots in my mind. But fearing the political misstep or doing something that might run contrary to people's expectations of me and making the faux PA. But still we navigate and there's all kinds of mismatches, there's all kinds of biases and myopic sort of tendencies in business to meet the needs of where people are and meeting the needs of where people will be. And if I don't speak up, who will? And so I think that courage eventually presents itself to get up out of the chair and do something. But then I realized the mapping of leadership that has been celebrated in my past career. Chapters was the alpha archetype, the alpha person, always driving the agenda, always driving the smart answer. And I realized, again, we're still navigating with all these biases, all these mismatches. Is there a different way that I could lead? And then I started looking at some of the leaders that were truly role models for me, and they didn't necessarily match to that archetype that had been historically celebrated.

Daniel Stillman

Yes.

Kevin Bethune

I've always enjoyed the quiet leader that knows to step away from the team room in a gnarly situation. They might go into their depth of expertise, whether it's coding, drawing, sketching, whatever making, and they bring something back to the team. And they're leading by example, by quietly showing what is possible, then they get out of the way and let the team have a try. Yes, that's leadership, too. You can lead and move the team forward by making, by speaking, by writing, by visualizing. There's many ways to lead, especially with this multidisciplinary opportunity upon us. I'm a fervent believer that we need to embody all kinds of leadership more and more.

Daniel Stillman

Such a beautiful way to lead the conversation, by framing the most important question, by framing the tension in the tension that you see in the challenger in the room and speaking to serve the conversation, not necessarily to say the smartest thing and to bring the attention to yourself. I think that's a beautiful way to look at what I might call conversational leadership. It doesn't have to be driving it, it can be gathering it, it can be corralling it. How else do you love to lead conversations? What are your ideal ways of hosting and bringing people together?

Kevin Bethune

Um,

Kevin Bethune

I think it probably stems from both optimism, but as well as, if I'm honest, past trauma of what it was like to be either recognized as a leader or be accused of being lukewarm or ineffective because I didn't match the archetype of what the organization might have celebrated as leadership. And I've been told in my past, why aren't you like this person? I'm not that person, that's why. But these are things, unfortunately, people hear, and especially when you're not representative of the majority.

Daniel Stillman

Yes.

Kevin Bethune

How that lands. I don't think people will fully appreciate the harm that that causes. And again, these are things I had to unpack. But with optimism and also recognizing that I've had huge opportunities of privilege navigating my career in terms of the spaces I've been able to navigate, I'm very optimistic, no matter how hard something is to say, like, what can we pull together as diverse ingredients? And through a collaboration, having a hope that we can answer the call? So I guess in the work, what drives the optimism is the chance to serve someone and actually impact the human experience in a very meaningful way. Does it manifest that way all the time? I think we all fall short of that hope sometimes, but that hope does keep us moving. Forward.

Daniel Stillman

I think that is an extraordinary aspect of the real design mindset. I'm going to remind myself by saying it now to put a link to my friend. I don't know if you know Aisha Bursell and her work. She wrote a book called how to Design the Life You Love, and it's a wonderful book. I had her on my podcast ages ago. She's a Turkish designer, and she talks about optimism as a fundamental aspect of design. And by golly, it is for realsies hard because we live in a very complex, very challenging world. And to maintain your curiosity and your optimism, kevin, how did you get those superpowers?

Kevin Bethune

Honestly, curiosity has been the defining thread. Again, easy to say that now, but I'm always excited by what you can do when you put two and two together and making two from less than obvious places. Sources of inspiration.

Daniel Stillman

Yes.

Kevin Bethune

And learning over my career to always look up, look out, get out of the office walls, and be open source to just like a fisherman, casting the net wide and getting as many rich and different ingredients as possible, no matter the ask, no matter the brief. Good things tend to happen when you do that.

Daniel Stillman

There's that optimism again. Kevin so can you talk briefly about the name of your firm, dreams, Design and Life? I feel like that's an important thing for us to touch on, because I know that's a significant combination for you.

Kevin Bethune

It's funny, the name came from a hashtag that I used on Instagram and Twitter and years prior to me starting the practice, and where the name comes from. I think that optimism analogously. You think of dreaming of what future possibilities could be had. So the idea of being childlike and dreaming and always keeping that hope alive at the other end of the branding is life. And that life is very concrete. There's pragmatic things, there's constraints, there's concrete realities that we have to navigate. But in a beautiful way, I've discovered how and learned how design could transform my life. And design can be a powerful broker or medium in between the dreaming and the life circumstances to create a path toward a better way forward.

Daniel Stillman

Yeah, what else would do that but intentionality, right? That's the core of design, believing that optimistically, it is possible to create something different. Boy. All right, Kevin. We've covered a lot of territory. Our time is shockingly, running short. What have we not talked about that is important for us to talk about? Because obviously there's more in your book than we could possibly cover in the time we have. There's more in your life than we could dig into. But what haven't we unpacked that would be worth circling back around and unpacking more?

Kevin Bethune

You know, I am I am even more bullish and fascinated by a lot of the nonlinearities and nuances that are involved in any effort that we have to go after a new innovation opportunity or to even investigate what might be a possibility to go pursue. And I am spending a lot of time noodling on what does nonlinearity mean in our journey toward innovation? What are some of the nuances that make innovation endeavors more successful? And I think of the work of friends like Myro Percini, who's a chief design officer of PepsiCo. His book that came out recently, of course, it's not going to be with an Eyeshot. Give me 1 second.

Kevin Bethune

Where is it?

Kevin Bethune

Of course, it would have walked away from my office. Give me 1 second. I want to get the name right out of respect for him.

Daniel Stillman

It's all good.

Kevin Bethune

So. Yeah, his book is Myra Percini's book, the Human Side of Innovation the Power of People and Love with People. That's just one great example of the nuances around. Like, we have to remember that people still drive the pursuit of innovation versus a framework or a methodology. And some of the attributes, the nuances that he brings to light the characteristics of what he calls unicorns or even designers. And are people in love with people bringing the nuances out? And I think if more people appreciate what to look out for and what to sort of appreciate, that's different than the typical archetypes of leadership that are often celebrated in business. Yes, he's giving us a whole landscape of attributes, of the nuances, of what makes our differences actually compelling when we think about innovation. That's just one facet of these nuances and nonlinearities that I think we really need to unpack for people so that they can identify those attributes and recognize that they're valuable. And that's something that is left on the cutting room floor for what's prioritized.

Daniel Stillman

The idea that it's the people and not the framework is a really beautiful perspective because going back to the name of your firm, Dreams, it really does come down to what is the dream? What are the dreams of the people in the room? What's the dream of the organization? Like, what are we really trying to create? There's no objectively perfect way to do it. It really is driven by the people.

Kevin Bethune

Absolutely. And the people that we were designing for, designing with, or including, they have dreams too. And instead of engaging them with whether do you like this handbag I'm about to sell you? What are their dreams? What are their unmet aspirations? What are their motivators? How can we tap in and show up for them correctly?

Daniel Stillman

Yeah, you mentioned this word wayfinding a couple of times and nonlinearity at the beginning of our conversation as well, that there's a lot of ambiguity in the design process and the process of going from curiosity to product market fit and growth and scale going through that S curve, it's nontrivial. It is complex. What helps you wayfind through that process? How do you be a good wayfinder for the teams that work with you to help them through that process in a way that feels safe.

Kevin Bethune

I do think that fluency is important and especially in environments where maybe design might be the youngest discipline to be at that table of conversation, which is typically the case. So I definitely have seen the disservice of design talking theoretical about its benefits, of why we exist and how great design is. If I beat my chest on that all day, I'm going to sound very theoretical to these other communities that matter equally at the table. So the more that I can be, as one of my mentors puts it all the time, the more I can be subversive with a good heart and show what design can bring to help the business. The collective team. Achieve its goals and ideally, at the same time, be systematically respectful of how we visualize and shine a light on the implications of every business or design decision. We have that opportunity to be subversive, to open everyone's aperture, to think about broader ramifications. And that I think is a beautiful thing when it's allowed to sort of have the breathing room to shine and be delivered.

Daniel Stillman

Yeah, lovingly subversive, being subversive with a good heart. I guess I'm paraphrasing when I think about you stepping up and drawing a diagram about what you are seeing, that seems to me to be wayfinding and to be lovingly wayfinding to say I believe that this is where we are and helping other people see what you see. It's a huge act, but it doesn't have to be so effortful. You just have to get up and draw.

Kevin Bethune

Yeah, honestly, instead of using the word design all the time, instead of not just saying open the aperture all the time and encouraging people to do that. But I'm in the business of value creation and no matter the business opportunity in front of us, it's always a question of like, who are the stakeholders? It's never just about the end, consumer consuming, there's a myriad of stakeholders and oh by the way, the planet is a stakeholder. So let's map the value criteria across that constellation of people or entities and ask ourselves, do we have the convictions and capabilities to answer the call, to answer the need? And oh by the way, those needs are shifting all the time thanks to trends and new paradigms. So can we anticipate where the value will be, where that value criteria will be? And again, all that gives me hope that we can figure out new and novel ways and how to show up for people.

Daniel Stillman

Can you say a little bit more about I love that phrase, new and novel ways to show up for people. Put a little color.

Kevin Bethune

Yeah, I guess. Sort of. The negative paradigm of that is, unfortunately, in a digital hyperconnected world, many times we can feel trapped in this flywheel of marketers marketing things to us and consumers consuming. And we see the perils of that paradigm in terms of the unsustainability of it and the disrespect on ethics and privacy and these kind of things. But instead, if we figure out how to tap into the value criteria of where people are, where people will be, I think we'll be more thoughtful of creating new avenues of utility for people to say, oh, that product or service. I could see that being a part of my life. I'm willing to take a bet and give that a try because maybe that's driving new meaning for me, and I'm willing to go down that avenue of utility you've just created for me by your new product or service. At the same time, that person's also navigating an information rich world with emails and messages and ads and pinching from every single direction. But how can we do a better job of clearing the noise for them and giving them the information that matters so that they would want to use that utility, that meaning that we've created for them. And if we show up consistently and are aligned with their value set with our values, we'll create emotional resonance where they'll keep coming back to that same experience consistently and we'll have a loyal relationship yes. Versus this transaction.

Daniel Stillman

Yes. I can't help but think that we're not just talking about organizations creating products and services for consumers, but also the way you'd like designers, anybody who's creating value to be thinking about all the people that they collaborate with.

Kevin Bethune

Absolutely.

Daniel Stillman

Because

Daniel Stillman

creating value with and for other people in a way that helps them clear out the noise is nontrivial. It's very easy to get lost in, well, here's my big deck and I'd like to take you through it slide by slide versus making it easy for somebody to work with you and for you to all to create value together.

Daniel Stillman

I'm going to assume that I can take that message and apply it not just from the inside of an organization to the outside, but between all of the different components of an organization, between all of the stakeholders within a value creation chain. That lesson, I think, is a really beautiful, almost parting moment. We're almost at the end. So where should people go to learn about all things Kevin Bethune? Where can we send people to the Internet so that they can learn more about your book and your work and learn about what?

Kevin Bethune \

I appreciate that. If folks go to Kevinbethun.com Just My Name, there's all kinds of forks in the road to get you where you need to go, whether it's dreams, design and life or the books. And then on social media, it's just at Kevin Bethune. I'm easy to find on all major platforms, so I appreciate the opportunity.

Daniel Stillman

It's my distinct pleasure. So one last micro question. What's your next book going to be called?

Kevin Bethune

Title TBD. But I think folks got a preview a little bit by our conversation around these nonlinearities and nuances.

Daniel Stillman

Nonlinearities and nuances that sounds like the beginning of a trade. PM. Yeah. I love it. I love it. Nonlinearity is oh, boy. I mean, that's a tough one, navigating all that ambiguity.

Kevin Bethune

Yes. I think that's what we're mired in, if we're honest.

Daniel Stillman

Yeah.

Kevin Bethune

So how do we handle it?

Daniel Stillman

How do we handle it? How do we handle it? Kevin, give me the Tweet before I buy the book. How do I handle all that ambiguity? I've got lots. What do I do with it?

Kevin Bethune

Well, I'm going to do my best to shine a light, to give people some wayfinding tools. How about that?

Daniel Stillman

Okay. All right. I might click the preorder button on that.

Kevin Bethune

Awesome.

Daniel Stillman

Awesome. Thank you so much. I really appreciate your time and sharing all of this goodness. And I'm also going to hopefully put some of these diagrams in the post so people know what we're all talking about. Thank you so much for your time, Kevin. I really appreciate it.

Kevin Bethune

Thank you for the opportunity. Nice to chat with you.

Daniel Stillman

Okay, we'll call scene.

A Leader's Guide to Managing Organizational Emotions During Layoffs and Beyond with Emily Levada

My guest today, Emily Levada, is a seasoned Chief Product & Technology Officer. Currently, she is the Chief Product Officer and Interim co-CEO at Embark Veterinary, a company dedicated to leveraging genetics to enhance the health and longevity of dogs. During her tenure, the company has achieved notable recognition, ranking as the #3 fastest-growing private company in Massachusetts and earning a spot on Forbes' list of promising venture-backed startups.

She also serves as a Board Member at JCC Greater Boston, bringing her expertise to contribute to the organization's growth and development and holds a significant role as a Member of the Customer Advisory Board at UserTesting, where she actively engages in guiding and advising the company.

Emily is also a two-time podcast guest, my first ever! We did an episode a few years back where she shared some wonderful insights and frameworks about Trust, Communication and Psychological Safety in teams.

Emily was also gracious enough to be a guest mentor for the Innovation Leadership Accelerator cohort I co-ran with my friend Jay Melone from the product innovation consultancy New Haircut some years back.

In this conversation, we sat down to talk about managing organizational emotions, especially negative emotions, and especially during critical junctures, like layoffs - something that many folks have been through, and many folks in the past year. I knew that Emily had some experience with this in the past and had some great thinking to share around this crucial leadership topic.

There’s no *good* side to be on in a downsizing event - the people who are losing their jobs and income are also losing a sense of identity and need to navigate an uncertain future. But the loss of identity and the need to face an uncertain future is also true for the folks who are still with the company - both the “rank and file” and the leadership.

Layoffs done poorly can dent a company culture.

Emily emphasized the importance of transparency in the period leading up to a layoff, as it builds trust and can mitigate negative emotions.

On the other hand, leaders often have a desire to protect people from such difficult conversations until the last possible moment, so the whole team can focus on their day-to-day jobs.

I explored this polar tension between these two fundamental values, transparency and protection, with Emily using a tool called Polarity Mapping, developed by Barry Johnson Ph.D., the creator (and registered trademark holder!) of The Polarity Map®! You can read more about polarity mapping in my friend Stephen Andserson’s short blog post here and check out Dr. Johnson’s company, Polarity Partnerships here. IMHO, Stephen’s version of Barry’s diagram (below) is a bit clearer!

The basic idea of Polarity mapping is that often we feel pulled by two values, like:

Should we focus on Innovation or Efficiency?

Should we prioritize Deadlines or Quality?

Growth vs. Consolidation?

Short-term Gains vs. Long-term Organic Growth?

Centralization vs. Decentralization?

(thanks for these examples, Stephen!)

In my own coaching work, I’ve found leaders can struggle to navigate conflicting parts of themselves, forming inner polar tensions that leave them feeling stuck, like:

“I need to be flexible vs I need to be firm”

“I need to lead the conversation vs I need to let the conversation flow”

“I need to be aggressive or I have to be more passive”

“I need to listen more vs I feel the need to fix challenges”

“I want to be authentically myself vs I need to be a chameleon to get by”

And because we get pulled between them, and feel the polarity to be an unwinnable double bind of “damned if I do,” we kind of flub the balancing act. Polarity mapping asks us to be ultra-specific about the positives of both values AND to be very clear on the downsides of over-indexing on one value to the detriment of the other.

Doing a mapping like this can help us thread the needle of polarity, and look out for the early warning signs of over-indexing in one direction or another.

Below is a version of a polarity map for the tension Emily describes in our conversation, between Transparency and Protection.

Emily points out that these polarities pop up, not just at crucial moments in a business like layoffs, but in day-to-day operations, too.

Leaders can feel that Emotions are Inconvenient, but Team Emotions have real impact

Emily shares the top three negative organizational emotions she finds can deeply impact a team’s ability to learn (i.e., be willing to experiment), be creative (i.e., being able to innovate) and be fundamentally effective:

Anxiety (Fear)

Boredom

Apathy

Fear, anxiety, and boredom are detrimental to creativity and productivity in knowledge work. Leaders need to address these emotions and create an environment that fosters engagement and challenge - and ultimately, create a learning organization.

“People cannot do creative knowledge work when they feel fear and anxiety and boredom. Those things are just incompatible.”

Emily suggests that well-run one-on-one meetings are crucial for understanding how team members are feeling and detecting signs of overwhelm, underwhelm, or “whelm” in their job. One-on-ones can help build a foundation of trust and safety, on which we can build honest and productive conversations.

Emily also shares some straightforward approaches for shifting these key negative emotions:

Anxiety: focus on building psychological safety for teams experiencing anxiety, and provide more transparency and context.

Boredom: create relevant challenges

Apathy: create accountability and challenge for teams experiencing apathy

AI Summary By Grain

Daniel and Emily discuss the importance of transparency and managing emotions during layoffs, emphasizing the need for psychological safety and building trust with team members. They suggest regular check-ins, icebreakers, and pulse surveys to gauge team emotions and prevent negative impacts on productivity. Emily explains that effective accountability requires understanding how a person's job connects to company goals, setting appropriate metrics, and articulating success with clarity.

Key Points

Emily discusses the importance of clarity and messaging in advance of a layoff, and how it can build trust with employees (11:06)

Emily shares an example of how to signal potential risks without creating panic, and they discuss the balance between protecting employees and providing transparency (16:08)

Daniel and Emily discuss the need to optimize for creativity and adaptability, especially after major changes like layoffs (32:41)

Emily suggests developing a measurement system to understand where the team is emotionally, including individual conversations, surveys, and observation. She also recommends doing a listening tour to hear from team members at all levels. (34:45)

Daniel and Emily discuss the belief that people want to do great work and the role of psychological safety in creating a context for great work (48:54)

Links, Quotes, Notes, and Resources

Trust, Communication, and Psychological Safety with Emily Levada

The Joys of Polarity Mapping, by Stephen Anderson

Polarity Partnerships

Minute 1

Daniel Stillman:

And this is something that comes up a lot, which is like, how do we do layoffs? How do we manage the process, but also the emotional space and damage, blow back that happens. And what do we do about the team that's left over? As a product leader, how do you think about this thing that is pretty much inevitable and currently very common?

Emily Levada:

Yeah. I mean, I wish it wasn't inevitable. I mean, I wish we all were able to manage our businesses effectively enough that we never over-hired, overstaffed, had imbalances in the skills and capabilities or anticipated changes in the market. All of those things. At some level, doing a layoff is a failure of leadership's ability to plan for the future effectively. And of course, leaders are humans and it's impossible to predict the future. And that's sort of what I think makes it feel inevitable at some level. I do think that there's a couple of things that are really important. And the first, which I think is the hardest, and the one that I find people push back against the most is actually transparency in the period leading up to a layoff. Because the reality is that... Well, I think people know this, and being a product manager is a lot about managing other people's expectations. And there's this notion that when reality is better than your expectations, you experience delight and when reality is worse than the expectations, you experience disappointment or other negative emotions.

And usually we're talking about customers here. And one way that you can solve for that or drive customer delight is by making the reality better. But another way you can do it is by mitigating people's expectations. And you don't want to sort of overpromise and under-deliver. And I think that the more I've done layoffs, the more I felt like, hey, look, there's something about clarity when a layoff happens about why that decision is being made, about either the business hasn't been in a good place, or the business has this problem and we need to solve this problem. A lot of layoffs come out of the blue and you have leaders who saying, everything's going great, everything's wonderful. Oh, by the way, we're laying off 15% of the company. And that all of a sudden breaks trust because those things are not compatible with one another.

Minute 15

Daniel Stillman:

So do you want to talk about why it's important to learn how to navigate negative emotions and what's important about being able to lean into those?

Emily Levada:

Yeah, sure. I think there are also these misconceptions. I think a lot of managers think emotions, well, a lot of managers think emotions are inconvenient.

Somehow a thing that they have to deal with, but not their responsibility, explicitly, not their responsibility. And also that emotions are only the realm of the individual and versus the realm of the team or the organization, which isn't to say that individuals don't have emotions, but I'm also interested in this sort of organizational emotion that the sort of team emotion and thinking about how you manage that. And I think the real reason why, I mean, what I'm interested in is, how do you create organizations that can move as quickly and effectively as possible towards the results they're trying to drive? And the framework that I use when thinking about this is basically focused around learning. The idea being that if you can learn effectively, you can do anything. You can sort of move into any new space. You can find value sort of anywhere, and you're sort of gated by your ability to learn what's going to be of value quickly.

But I find that that goes hand in hand with a bunch of other things that we care about, creativity and risk taking and resilience and a bunch of other things. And so how do we get our organizations and the individuals in our organizations into this headspace, into this mood, into this emotion where they can be focused, they can be in the zone, they can be resilient and optimistic. And my perspective is that there are sort of three major negative emotions that detract from our ability to do this effectively. Those are fear and anxiety, boredom and apathy.

And a lot of the reason that I have come to those three is they show up over and over again as you review organizational behavior work. And a lot of the frameworks that I've come to really love and to utilize in my day-today, you see these three emotions or versions of these three emotions show up over and over again. And at some point I've started to feel like, hey, look, a lot of what it takes to actually create the conditions for success in my team is about how do we manage anxiety, boredom, and apathy in the team. Because if you can manage those effectively, you can create a team context and a team environment where that learning and that creativity and that resilience is possible.

Minute 35

Daniel Stillman:

So the value of challenge can activate someone in a good way. It can give them a sense of, there's impact. We want to connect with what they're doing to not just output, but impact. And if we over-index on challenge, then people will just feel, we'll go back into that anxiety zone.

Emily Levada:

I think that's right. And I think also there's an underlying value here, which is maybe not in a polarity, but which is as a leader, in order to do this effectively, in order to create effective accountability for that team, you actually have to get your shit together.

Daniel Stillman:

You want to break that down for us a little bit?

Emily Levada:

You have to understand how that person's job connects to the company goals. You have to be aligned on what you're trying to accomplish. You have to set an appropriate metric or measurement for that person to hit. You have to be able to articulate to them with clarity what success looks like.

And a whole bunch of things that sometimes managers are not good at, but it's a good opportunity to say, oh, this is what my team needs from me, and therefore this is what I should focus on in creating this accountability and this productive pressure.

More About Emily Levada

Emily Levada (She/Her), is a seasoned Chief Product & Technology Officer. Currently, she is the Chief Product Officer and Interim co-CEO at Embark Veterinary, a company dedicated to leveraging genetics to enhance the health and longevity of dogs. During her tenure, the company achieved notable recognition, ranking as the #3 fastest-growing private company in Massachusetts and earning a spot on Forbes' list of promising venture-backed startups.

She also serves as a Board Member at JCC Greater Boston, bringing her expertise to contribute to the organization's growth and development and holds a significant role as a Member of the Customer Advisory Board at UserTesting, where she actively engages in guiding and advising the company.

Full Transcript

Daniel Stillman:

Okay. So Emily, I'm so grateful that you made the time for this conversation. You're actually the first, second time interviewee conversationalist.

Emily Levada:

Wow.

Daniel Stillman:

And I'm-

Emily Levada:

What an honor.

Daniel Stillman:

Well, yeah, it's very kind of you to say. Welcome back to the conversation factory. I get to say it for the first time.

Emily Levada:

Thank you. I'm glad to be back.

Daniel Stillman:

The association, when I think of layoffs, I think of... I saw you post recently on, well, I guess it's not that recently anymore now, on LinkedIn around, a leader's guide to managing organizational emotions and your desire, your interest in creating a learning organization. And I know that you've been involved in and have been responsible for layoffs in the past. And this is something that comes up a lot, which is like, how do we do layoffs? How do we manage the process, but also the emotional space and damage, blow back that happens. And what do we do about the team that's left over? I've watched you try to find jobs for people from your last company after layoffs, find jobs for people you've had to lay off. You do put a lot of love and care into it. As a product leader, how do you think about this thing that is pretty much inevitable and currently very common?

Emily Levada:

Yeah. I mean, I wish it wasn't inevitable. I mean, I wish we all were able to manage our businesses effectively enough that we never over-hired, overstaffed, had imbalances in the skills and capabilities or anticipated changes in the market. All of those things. At some level, doing a layoff is a failure of leadership's ability to plan for the future effectively. And of course, leaders are humans and it's impossible to predict the future. And that's sort of what I think makes it feel inevitable at some level. I do think that there's a couple of things that are really important. And the first, which I think is the hardest, and the one that I find people push back against the most is actually transparency in the period leading up to a layoff. Because the reality is that... Well, I think people know this, and being a product manager is a lot about managing other people's expectations. And there's this notion that when reality is better than your expectations, you experience delight and when reality is worse than the expectations, you experience disappointment or other negative emotions.

And usually we're talking about customers here. And one way that you can solve for that or drive customer delight is by making the reality better. But another way you can do it is by mitigating people's expectations. And you don't want to sort of overpromise and under-deliver. And I think that the more I've done layoffs, the more I felt like, hey, look, there's something about clarity when a layoff happens about why that decision is being made, about either the business hasn't been in a good place, or the business has this problem and we need to solve this problem. A lot of layoffs come out of the blue and you have leaders who saying, everything's going great, everything's wonderful. Oh, by the way, we're laying off 15% of the company. And that all of a sudden breaks trust because those things are not compatible with one another.

Daniel Stillman:

Right.

Emily Levada:

And so I think particularly with the last layoff that I did, it was very important to me that the leadership team was messaging in advance. And it was as simple as, hey, we're having trouble balancing the budget, which was the reality. We were having trouble squaring our revenue projections with our costs, and the largest part of our costs was headcount. And we were going through the process of trying to figure out what are all of the other ways that we can balance this budget that are not doing layoffs, but we try to be at least open about the fact that that process was happening and not that everything is wonderful and the plans are all coming together and it's all going to be great. And I think part of the reason that people are afraid of doing that is because they feel like it creates unnecessary anxiety in the organization in advance, and it creates sort of discontent or fear. And for me, I think there's some amount of trading off anxiety before a layoff for trust building in your willingness to be transparent with an organization after a layoff.

Daniel Stillman:

Wait, so let's underline that because you're saying that the blow-back for not being... Well, the downside of being transparent is you can create anxiety, but if you are as clear and transparent as you can be or as you feel you can be gain trust?

Emily Levada:

Right.

Daniel Stillman:

Both of the team before, but also really importantly of the team that's remaining.

Emily Levada:

That's remaining.

Daniel Stillman:

Afterwards.

Emily Levada:

Right. And that also the problem that I have seen where you don't give any indication the layoffs coming, you do a layoff. Now the people who are remaining are saying, well, how can I trust you that when you say things are going well, that they're actually going well. And you have to start earning back trust with the people who are there. But really, I mean, what I'm talking about now is basically all sort of emotional management.

Daniel Stillman:

Yes.

Emily Levada:

None of this is the actual ticking and tacking of how you do a layoff. It's all about how you think about what is fair and right and just and produces the overall fewest negative emotions, both before and after.

Daniel Stillman:

So what's the opposite value? So on one hand, transparency is valuable because if we index on it, we create trust. And if we under index on transparency, we can create anxiety because people don't have clarity, we create anxiety for them. On the other hand, I feel like people say, I want to play this close to the vest. And there's reasons for that. What's valuable and good about being thoughtful or cautious or intentional about what you share with your team?

Emily Levada:

Yeah. I mean, I don't want this to sound like there's not a lot of discretion that goes into what's shared or when it's shared. I think there's a difference between the sort of simmering of anxiety of, hey, there might be a correction that needs to happen in the business and it could impact me, and does that make me demotivated or even consider leaving this company? But I think, what I'm not suggesting is the kind of transparency that creates panic.

Daniel Stillman:

Right.

Emily Levada:

Which I have also seen. So I have seen some leader be like, "Oh yeah, the layoff's coming in two weeks." And then everybody's like, "Wait, give me all the rest of the information." And then they're like, "Yeah, nope. Can't share that information. Don't have more details." Then you just have panic for two weeks. But I think it's the signaling of there is hard work being done to understand what's going to be best for the business, for our stakeholders, for the majority of our employees, potentially at a cost to some other employees. And we are working hard to solve this problem in every creative way that we can. But this happened not that long ago. We were sort of signaling this, and there's a board meeting coming up. We need to do the budget. We're having trouble balancing the budget, we're working through the options. And a very astute individual in an all company meeting said, does that mean that there could be another riff?

And we said, yes, it does mean, that is the very last lever that we would want to pull. And as of right now, we don't have concrete plans to do a riff, but if we cannot solve the budgetary problems other ways we could end up having a conversation about needing to do it. Right, that's the honest answer. But I think that would be a very difficult answer for a lot of leaders to give, because I do think that the other value, and it's a protection mechanism. You want to protect your team. These are the things that managers worry about so that employees don't have to worry about.

Daniel Stillman:

Yes.

Emily Levada:

And there's a desire to shield your team from uncertainty and from ambiguity because it makes it easier for them to do their jobs. It provides a sense of clarity and stability and all of those things, which we value. But I think there's some line where you can go too far.

Daniel Stillman:

Yeah. Yes.

Emily Levada:

In that direction, into a false sense of clarity and civility, which then ultimately ends up feeling like a lie after the fact.

Daniel Stillman:

Yes. Okay. So this is great. I think we're where I was hoping we would get to, because one of the tools that I was actually really excited to do a whole other interview with you about is, this idea of polarity mapping as a leadership skill, having to manage paradox as a leadership skill. And I think you've identified the paradox and the two by two of this tool and people can Google it, I'll put a link in, but it's like, we have these two values and plus and minus of both of them, because both values have goodness in them.

And over-indexing on them, over to the negation of the other creates dysfunction. So if we're talking about protection and transparency as two values where it's like I want to protect them, but I also want to be transparent, what I'm hearing is, I want to protect them because what's good about this, I want to shield them from things they don't need to know about because I want them to be able to focus on doing their job and creating value. And I want to give them transparency because I want them to build trust. And if I over-index on either of those, I can get anxiety and panic, I think, is what we're talking about.

Emily Levada:

Yes.

Daniel Stillman:

And so you're kind of just... Go ahead.

Emily Levada:

By the way, I mean this polarity exists in everyday management all the time. You hear this all the time, the leader, your employees, let's say you come to them and you say, I've made this decision. We've had this discussion, I've made this decision. They get upset because they want it to be included in the discussion and the decision. But when you come to them and say, I have this big problem and I don't really know the answer and I want you to help me figure it out, then they feel like you're not giving them enough clarity in the direction that you're providing. And this trade off between, what is the right moment to bring employees something that is clear enough that they feel they can understand it, they can run with it, but transparent enough in the sort of sausage making of it that they don't feel blindsided by the decision. And I think this is just a very amplified version of that polarity.

Daniel Stillman:

Yeah. Because I think I've definitely been in situations where leaders have over-indexed on protection and everything's going to be fine because they really believe that they're going to pull the fat out of the fire and they don't. And it comes as a serious whiplash. And I think what we're positing here is the negative emotions that come as a result of over-indexing on protection. People are thinking about now, in protection and people are maybe not thinking so much about, and then after, with protection, and they're on reduction of harm now and not long-term management of organizational emotions. So maybe, sorry, is there more that you want to?

Emily Levada:

No, go ahead.

Daniel Stillman:

Well, because I think this is maybe an interesting place to, a lot of people resist dealing with negative emotions because they are uncomfortable. And for those of you, because there's no video for this, Emily just did a very deep nod that I felt that in my chest. You're like, yes. So do you want to talk about why it's important to learn how to navigate negative emotions and what's important about being able to lean into those?

Emily Levada:

Yeah, sure. I think there are also these misconceptions. I think a lot of managers think emotions, well, a lot of managers think emotions are inconvenient.

Daniel Stillman:

And sorry, that's not funny at all. Funny because that hurts.

Emily Levada:

Somehow a thing that they have to deal with, but not their responsibility, explicitly, not their responsibility. And also that emotions are only the realm of the individual and versus the realm of the team or the organization, which isn't to say that individuals don't have emotions, but I'm also interested in this sort of organizational emotion that the sort of team emotion and thinking about how you manage that. And I think the real reason why, I mean, what I'm interested in is, how do you create organizations that can move as quickly and effectively as possible towards the results they're trying to drive? And the framework that I use when thinking about this is basically focused around learning. The idea being that if you can learn effectively, you can do anything. You can sort of move into any new space. You can find value sort of anywhere, and you're sort of gated by your ability to learn what's going to be of value quickly.

But I find that that goes hand in hand with a bunch of other things that we care about, creativity and risk taking and resilience and a bunch of other things. And so how do we get our organizations and the individuals in our organizations into this headspace, into this mood, into this emotion where they can be focused, they can be in the zone, they can be resilient and optimistic. And my perspective is that there are sort of three major negative emotions that detract from our ability to do this effectively. Those are fear and anxiety, boredom and apathy.

And a lot of the reason that I have come to those three is they show up over and over again as you review organizational behavior work. And a lot of the frameworks that I've come to really love and to utilize in my day-today, you see these three emotions or versions of these three emotions show up over and over again. And at some point I've started to feel like, hey, look, a lot of what it takes to actually create the conditions for success in my team is about how do we manage anxiety, boredom, and apathy in the team. Because if you can manage those effectively, you can create a team context and a team environment where that learning and that creativity and that resilience is possible.

Daniel Stillman:

Yes. So my first follow up question for that is, in my book, I sort of posit that nobody has a conversation thermometer or speedometer, and yet somehow we all... Oh God, this is moving too slow. This is moving too fast, this conversation is too hot, this conversation is too cold. With what organ of you, do you feel like you detect that there is apathy, anxiety, or boredom in the team, right? Because we can feel a person-ish, that's empathy or mirror neurons, but how do you feel like you read that room, especially given the fact that maybe you aren't seeing them all together in one place at one time, very often, how are you reading what's going on?

Emily Levada:

So I do think to some extent for the people that I do interact with more frequently, there is relationship building and you just start to learn. You sort of know when someone's on and when they're off or when they're right, when they're nervous about something or whatever. And so there's some amount of that. I will say at the team level, it's much harder virtually. And I remember saying when we first went virtual that I felt like I had lost the sensory organ because there was so much observation in a team meeting of who's paying attention, who's disengaged, who's talking to who, who got excited physically by those ideas, or what were the hallway conversations that happened after a meeting?

I do think that it's possible, however, to read a fair amount of this based on the signals around what your team is outputting and also where the problems are cropping up. So for example, teams who are in apathy are just much less likely to actually deliver results, and they're much more likely to be engaged in conflict or miscommunication. And even your attempts at moving the team top down don't actually produce the results that you want, right?

Daniel Stillman:

Yeah. Apathy is a kind of inertia.

Emily Levada:

Right. People who are bored tend to start... Boredom often goes hand in hand with your bureaucracy. And they'll often complain about, just, I didn't need to be in that. Why are we in so many meetings about things that we all already know? Or they start looking, they start job crafting, they're not feeling challenged enough, and so they start finding other things to do that aren't their actual job. And so it's a little bit of that, just so fear and anxiety tends to create, people tend to turtle, they stop sharing information as freely.

And so you can start to see some of those things in terms of where are the conflicts happening, what's getting escalated to you, which projects are actually moving and which ones aren't. And I think it's one of those things when you start paying attention, but sometimes you do have to get in and evaluate. You and I have talked about my trust and conversation framework, which actually happens to have these four emotions in it. And there are tools like that that you can go in, you can just say, okay, how's everybody feeling? Right? I think we've talked about doing icebreakers where you get into a room and you have everybody just draw a picture of how you're feeling and see what people come up with.

Daniel Stillman:

And if you wait until things are terrible to do that, that's a signal. So it's doing this regularly, really taking a reading.

Emily Levada:

We have a question on our employee pulse survey that is, I don't remember how it's worded, but it's like, what's your predominant feeling? Or how are you feeling most days? And the choices are fatigued, anxious, optimistic, something else, but they're basically synonyms of these things. And so you can get a pulse of, oh, this team is feeling this way, and that team's...

Daniel Stillman:

Yes. Now this is clearly a great reminder that regular one-on-ones done well are so important. I think somebody shared with me recently one of their favorite questions, which was like, are you overwhelmed, underwhelmed or whelmed in your job? And in a way, that's kind of what you're trying to get from that pulse survey. And you want to have a human response from your team members and be listening to how they're responding. So these are... Yeah, sorry. Go ahead.

Emily Levada:

And that's obviously particularly for direct reports and one-on-ones, that is also a skill and a conversation that you build over time. You can ask that question of anybody, even if it's your first day managing them, but you want to build a relationship where an employee walks into the room and says, I'm overwhelmed, or says, you know what? I've been really bored. Right? And where you can just have those conversations openly without having to go dig for that information.

Daniel Stillman:

And this is psychological safety, which is why it matters. And I want to loop us back to the question of, what we're trying to optimize for. And if I'm understanding you right, it's that if we can keep our team in the learning zone, they can adapt to anything. And what we're trying to optimize for is getting their creativity, both pre but also post layoff, that if we over index on protectionism and don't lean into managing and anticipating some of these negative emotions, especially when we're going to need it most after we've had a reduction in force and we want people to do more with less, we're not going to be able to get that creativity out of them if we've lost trust, if we've afraid of telling us what's really going on.

Emily Levada:

And you're always going to see a drop in productivity after layoff. Actually, you're going to see a drop in productivity after any major change of transition, not just a layoff. And the question is, how quickly do you get back? And I will say this is particularly important in roles and jobs and companies where there's a really high degree of uncertainty and complexity and ambiguity.

Daniel Stillman:

So most of them.

Emily Levada:

Right, so most of them, if you're making widgets, actually managing by fear might work just fine.

Daniel Stillman:

Fear and Fiat, all the apps, but we're talking about not, the other thing. You need to get the best of people.

Emily Levada:

But people cannot do creative knowledge work when they feel fear and anxiety and boredom. Those things are just incompatible.

Daniel Stillman:

So when we talk about driving resilience and creativity, how can we build our toolkits as leaders to set ourselves up for success pre layoff? And you've talked a little bit about this, but I think we could double stitch on it and then post to reduce that refractory period.

Emily Levada:

Yeah, I mean, I think the first and most important thing, and sometimes the hardest is developing this measurement piece to sort of know where your team is. And part of that is because you're going to do different things. If your team is bored versus your team is anxious, you're going to do different things to solve those problems. And so you kind of have to know where your team is. And so as we talked about, some of that can be individual, talking to people on your team. Some of that can be quantitative measures by doing surveys.

Some of it can be observation of what's not working, or what questions are people asking. And after our last layoff, I just did a listening tour that was, go talk to as many people as I can in three weeks from all across my organization at different levels and different functions and hear what people are saying and then try to distill down from there. And so I think that's the big one or the big first step is actually getting good at figuring out where your team is. And then there's basically two levers that you're going to pull.

One is creating better systems of accountability and challenging your team more. And the other is building psychological safety or trust with your team. And we could talk about when you do which things, but ultimately I think it comes down to having those two skill sets or those two tools in your toolkit.

Daniel Stillman:

So my follow-up is going back to a point you made earlier, sharing, being transparent about what some of the challenges are. It sounds like if you want to involve your team in helping you solve that challenge, share that challenge with them in a way that they can participate in that challenge.

Emily Levada:

Yeah, I think so. And certainly I think if you're running a large enough organization, at least tapping the middle management layer or the layer below you to say, hey, here's how I'm thinking about this. Here's what I see. This is what I think we need to be driving, because they're going to be right that much closer to all of the individual employees on ground.

Daniel Stillman:

So what do you feel like is the most effective way to pull the most effective lever for you?

Emily Levada:

Well, I think it depends on where your team is. I think in today's environment, it's sort of most likely that people are in... Sorry, that's my dog squeaking his squeaky toy.

Daniel Stillman:

What's amazing, Zoom has filtered so much of it out.

Emily Levada:

Okay. Good. Can you not hear him squeaking?

Daniel Stillman:

I think I can. I'm aware that he's really got his jaws around that, but I'm cool with it. It's not showing that bad.

Emily Levada:

Okay.

Daniel Stillman:

I think they know that we're talking about them right now. He just looked up. It's like, me?

Emily Levada:

Okay, sorry. What was it?

Daniel Stillman:

No, it's all good. We're talking about where most people are right now is, there's a lot of fear.

Emily Levada:

Where most people are right now is either sort of apathy or anxiety. And I say that because those are the two states where you don't have psychological safety, and that lack of psychological safety is going to get you into one of those places. The difference is that in anxiety, the thing that creates anxiety over apathy is actually the high expectation. There's an expectation to do something, to be accountable for something. And there's some fear that if I don't do my job effectively, I'm going to be held accountable. With apathy, you actually have that fear, you're like, whatever. I can do this job in my sleep. I don't need to worry. Or who cares?

Daniel Stillman:

It doesn't really matter.

Emily Levada:

And so the important thing to do is, in that sort of apathy state is actually, I mean, the first thing to do is actually to drive that accountability. And when I say accountability, I don't necessarily mean if you don't hit X number, you're going to get fired. I mean, that sense of ownership and that sense of urgency, that little bit of stress that makes you really productive.

Daniel Stillman:

The dog requires attention. But it seems like you're also asking us to give people, it seems like in a way, the antidote to apathy is engagement, giving people things that they are truly excited about, that matter most to them, where they feel like they're impactful.

Emily Levada:

Yes. And I think sometimes that looks like a challenge, it looks like saying, hey, I have high expectations of you, and I believe you can meet those expectations, and I'm challenging you to do this thing, to own this thing, to deliver this result. And oftentimes, there are sometimes teams where that ownership actually isn't clear and people don't understand how their work connects to what the company is trying to accomplish. And so it is about how do you drive down to a discrete enough thing, an ask that feels like it's going to be meaningful and valuable and impactful and purposeful, because that's what people want. They want to feel that they're having an impact and having a purpose.

And that is going to challenge someone, right? Because ultimately, if you don't feel a little... Not really, not an exceedingly hard challenge, but that little bit of a challenge that makes someone sort of have to work. And I think that in some way, I know that's counterintuitive. If someone's feeling apathetic, give them more to do. But it's a little bit of this, it's easier to act your way into a new way of thinking than to think your way into a new way of acting kind of thing.

Daniel Stillman:

Wait, say that one more time.

Emily Levada:

It's easier to act your way into a new way of thinking than think your way into a new way of acting.

Daniel Stillman:

Yeah.

Emily Levada:

Right?

Daniel Stillman:

Yeah.

Emily Levada:

Sometimes it is just doing of the task that gets us engaged, and sometimes it's hard to start. And apathy, as you said, apathy in many ways is an inertia problem. And it's like how do you break people out of that inertia? The challenge is when you do that with apathy, you're going to put people into the anxiety zone. And that in many ways is why people avoid doing it because they're not comfortable with this idea that they're going to do something that creates anxiety for their team. But anxiety is at least active. It's an active state instead of an inactive state.

Daniel Stillman:

So what's the value going back to our two by two? So the value of challenge can activate someone in a good way. It can give them a sense of, there's impact. We want to connect with what they're doing to not just output, but impact. And if we over-index on challenge, then people will just feel, we'll go back into that anxiety zone.

Emily Levada:

I think that's right. And I think also there's an underlying value here, which is maybe not in a polarity, but which is as a leader, in order to do this effectively, in order to create effective accountability for that team, you actually have to get your shit together.

Daniel Stillman:

You want to break that down for us a little bit?

Emily Levada:

You have to understand how that person's job connects to the company goals. You have to be aligned on what you're trying to accomplish. You have to set an appropriate metric or measurement for that person to hit. You have to be able to articulate to them with clarity what success looks like.

Daniel Stillman:

Yes.

Emily Levada:

And a whole bunch of things that sometimes managers are not good at, but it's a good opportunity to say, oh, this is what my team needs from me, and therefore this is what I should focus on in creating this accountability and this productive pressure.

Daniel Stillman:

Productive pressure. And that's a very delicate guiding because on one hand... Yeah, go ahead.

Emily Levada:

Well, and so then there's the second lever, which is it was just creating psychological safety. And that is the lever you need to pull when your team is in the anxiety zone. And I say it that way in that sort of order because I find if you have a team that's apathetic, it's sort of easier to get them moving, to be doing and to see results. That makes it a lot easier to then build psychological safety and trust. It's much harder to build psychological safety and trust in this sort of inactive state.

Daniel Stillman:

Why is that? There's some things bubbling up for me, but I'm curious, why do you think that is the case?

Emily Levada:

Yeah. I think that some of it is just people are not as receptive to it. And some of that is just, they're just not engaged in the conversations. It's something about doing the work that creates the context for the conversations that help us build trust, where we can get into a room and say, okay, why is it that you care about this? Or why do you want to do it this way? The work gives us a context or content for the conversations which help us build trust. Does that make sense?

Daniel Stillman:

It does. I also think conversations are about feedback loops. And certainly when we're talking about organizational emotions, I think of a one-on-one conversation as like it's here, you and I are talking one-on-one, but an organizational emotion and an organizational conversation is this longer amplitude, and it requires time to know what's happening. And so you have to get things moving in order to have a feedback loop. There's no feedback loop-

Emily Levada:

And presumably you can pull these levers at the same time, but the trust building's going to take longer.

Daniel Stillman:

Yes.

Emily Levada:

And so it's actually not a bad thing if you see your team moving from apathy to anxiety. You just need to know that in both of those cases, you're living a world where you don't have enough psychological safety. And that should be then the focus. And the other thing that I see people make a mistake on, is they see a team has this high accountability and is feeling fear and is feeling anxiety, and they're worried about what's going to happen if we don't do our jobs effectively, or there's going to be another layoff or there's going to whatever. And some leaders' instinct is actually to pull back on the level of challenge that they're giving their team, that somehow they believe that psychological safety involves going easier.

Daniel Stillman:

But.

Emily Levada:

But it's not really what it means. Psychological safety is about creating an environment where we can have productive conflict and where all of the voices and opinions are heard, and we can be proactive about resolving problems, it's not the same thing. Now, that doesn't mean that you might not be overworking your people, and you might need to pull back a little, but if you create psychological safety, then you have a scenario where someone can come to you and say, "Hey, I have too much on my plate, and can we talk about what the most important things to do are?" Or they can go to a stakeholder and they say, "Hey, you made this ask to me, but I really don't think that's going to be the most important thing for us to do to our customer." We talk through that.

Daniel Stillman:

And you want people to be able to say that to you.

Emily Levada:

You want people to be able to do that. And if you, as a manager, again, getting back to protection versus some other value, if you try to protect them by just taking things off their plate, you're actually not creating the ability for them to get into this place where they're really doing this productive, constructive problem solving that delivers the most possible value.

Daniel Stillman:

And the hope is, the belief is, that people want to do the best work of their lives. I think there's this implicit assumption and the idea of psychological safety that if we produce the right amount of productive pressure and hire well and create the right context, people want to do great work.

Emily Levada:

Yes.

Daniel Stillman:

I know.

Emily Levada:

Yeah. Yes, you are right. People do want to do great work, and great work requires ambitious goals, and it requires conflict. It requires working through difficult things. I don't know, great things don't come easily.

Daniel Stillman:

No, they do not. Then they would be common. And in a way, I'm looking at apathy and fear and creating clarity and creating productive pressure is your way of getting people out of the apathy zone and to get them activated.

Emily Levada:

Right?

Daniel Stillman:

Yeah. So I mean, it's crazy. The time goes so fast. What have we not talked about that we should talk about? What have I not asked you that we should have asked you?

Emily Levada:

Well, I think just going back to the beginning, I think it's important to recognize when you do a layoff, that you're going to see fear and apathy, and it's maybe boredom. It's less common. It can happen. And the thing I think is important to stress is that, I mean, not only is seeing those things as normal and natural, but it's a thing that a manager can actively address in the way that they approach the team. It's not just the thing that happens to them that they have to wait for it to go away. And it's also incredibly unnatural after a layoff to say, oh, the thing I should be focused on is putting pressure on my team. And I think that learning, getting comfortable with this idea that there's a certain type of production pressure that allows the team to move forward and to feel like they understand that impact that they're having, they see results, and that allows them to create a context in which they can build back trust and psychological safety, actually gets you to where you want to be faster.

Daniel Stillman:

And that before, during, and after one of these events, knowing that they're coming, one of the things I heard you say is, get your shit together. The job of knowing what's going on with your team will determine which approach to use to get the most out of them.

Emily Levada:

I think-

Daniel Stillman:

And to create the best context for them to work through this.

Emily Levada:

Yeah, I think that's right. And again, to what we're talking about before, I think there's also a lot you can do before and during the process that helps you get there faster, right? Yeah. I mean, obviously I'm not helping former employees find jobs just because it creates psychological safety. I'm doing it because it's the right thing to do. And because I think they're amazing performers, and I want to see them be successful, and I would never have wanted to cut them for my team in a different situation. But it does help to be able to authentically say, this is why we are where we are. This is why we made the decisions. And by the way, we really believe, even though we've let these people go, we want to see them be successful, we want to help them. We're going to do right by them in the ways that we can. Those things all do contribute to your ability to build trust and psychological safety as quickly as possible back with the team that is still in this.

Daniel Stillman:

Yeah. You can't withdraw from the bank of psychological safety if you haven't invested in it.

Emily Levada:

That's true. And you also can't just hide and pretend that it didn't happen.

Daniel Stillman:

No. So I think the surprising bit of feedback from this is that post layoff, if I've set myself up for success, well, and there is psychological safety, creating positive pressure post layoff may be the most unexpected move to make.

Emily Levada:

Yeah. I mean, in a world where you did have psychological safety, I think what you would most likely see is boredom. Because basically the boredom happens in a world where you have psychological safety, but people aren't really sure what to do. They don't feel challenged.

Daniel Stillman:

Yes.

Emily Levada:

Oh, they don't have alignment. They don't know which direction to go. And so being able to sort of step in and say, focus on this thing, run in this direction. Here's the expectation, I'm setting a high bar. Actually, it creates that forward movement that is self-reinforcing.

Daniel Stillman:

So when will we have you on for a three-peat to talk about your book? Because you're just in the early stages, right?

Emily Levada:

Yeah, we are in the early stages. I don't know. I'll let you know.

Daniel Stillman:

Okay. That's a strong commitment. It's a challenging and emotional process. I'm glad you're working with someone.

Emily Levada:

Thanks.

Daniel Stillman:

I have someone I had on this podcast a while ago who talked, describes your work as being a book doula, and I think it's a very apt metaphor.

Emily Levada:

Yeah. This book has been rattling around in my head for seven years, and so it feels great to finally start getting some of it out into the world.

Daniel Stillman:

I'm really excited to see it real. In the meantime, how should people interact with you post this conversation? If they want to stay in the loop about all the things Emily Levada, how are they to do it?

Emily Levada:

Yeah. The best way is probably on LinkedIn. That's where I'm the most sort of active and plugged in.

Daniel Stillman:

Yes.

Emily Levada:

Nowadays.

Daniel Stillman:

Hit that follow button on LinkedIn. I hope you have that as your first.

Emily Levada:

I do.

Daniel Stillman:

Yeah. As your default action. Well, good God. An hour is barely enough time to scratch the surface of this topic, but I really appreciate your generosity in working through some of these questions, and I know that there's a lot of goodness in this. So thank you so much for this time.

Emily Levada:

Thank you for having me.

Daniel Stillman:

Well, we'll just call scene then if we feel complete.

Emily Levada:

Yes.

Daniel Stillman:

And we are complete.

Unpacking Mentoring with Jason Knight and Sandra Monteiro

My guest today is Jason Knight, the creator, host, producer, editor and promoter of the One Knight in Product podcast, a B2B SaaS product consultant, and fractional Chief Product Officer for companies that have gotten to product market fit and need help scaling their product team. Jason is also the founder of My Mentor Path, an inclusive, accessible and cloud-based mentorship service. 

Sandra Monteiro, a Product Manager at SAGE Publishing and a mentee of Jason’s, joined us halfway through to share her own experiences with mentoring, how she found her way to working with Jason as a mentor and what some of her learnings and insights from working with Jason as a mentor have been. She also shares her thoughts on what mentees should be thinking about as they search for and work with mentors.

We explored Jason’s mentorship journey and why mentorship matters to him, the challenges of Industrializing mentorship pairing and productizing the matching of the lopsided mentorship marketplace.

We also touch on how to measure the impact of the work and the subtle and important difference between Mentoring and Coaching. Jason suggests that many people who say they want coaching really want mentoring from someone who has “been there and done that”…and that great mentoring leverages coaching mindsets and skills in a practice he affectionately calls “centering”.

Some fundamental questions we explored were the differences and relative merits of FORMAL vs INFORMAL mentorship as well as working with someone INTERNAL vs EXTERNAL to your Organization

One of the big insights Sandra shared was shifting her expectations on the nature of the mentoring relationship from one centered around SOLVING vs conversations centered around TOOLS (ie, being offered relevant examples, learning materials and frameworks, holding space for emotional distance, and being offered broader context for challenges).

Links, Quotes, Notes, and Resources

Sandra Monteiro

Jason Knight

https://www.oneknightinproduct.com/bio/

https://www.oneknightconsulting.com/

My conversation on Unapologetic Eating and Living with Alissa Rumsey is here

AI Summary

Part One: Daniel Stillman with Jason Knight

The conversation was about mentoring and the challenges of being a mentor. Jason Knight discussed his experience with mentoring and his idea for setting up a platform for it. The discussion also touched on the differences between coaching and mentoring, the importance of honesty and transparency, and the need for mentors to recognize their limits.

Meeting summary:

(0:22) - Jason Knight talks about his path to mentorship, starting with a call center job where he had a mentor, then doing structured mentoring sessions in corporate, and finally offering himself as a mentor on Twitter and getting overwhelmed with bookings

(4:46) - This experience led him to consider setting up a platform for mentoring

(5:20) - Jason Knight discusses the challenges of being a mentor, including context switching and the importance of knowing someone over time for effective mentoring

(6:57) - Jason Knight discusses the benefits of long-term mentoring relationships and how they can lead to accountability and knowledge accrual over time

(9:29) - Jason Knight explains their two-sided marketplace for mentors and mentees, the challenge of matching, and how they encourage multiple mentorship relationships to address the imbalance between those seeking mentorship and those willing to mentor.

(17:16) - Coaching and mentoring share similarities but have big differences, with coaching being a craft that uses specific skills and techniques while mentoring requires experience in the industry being mentored in

(21:09) - Jason Knight emphasizes the importance of being honest about not knowing the answer and exploring together with the mentee

(22:31) - Jason Knight agrees and emphasizes the need for mentors to know their limits and stay in their lanes, recognizing when real support is needed

Part Two: Daniel Stillman with Jason Knight and Sandra Monteiro

The participants discussed the importance of both formal and informal mentorship, with a focus on qualities such as trust, respect, and open communication. The speakers emphasized the importance of providing tools and resources rather than direct solutions, and recognizing when a mentoring relationship isn't working out. They also discussed the value of paying it forward by being the mentor you wish you had in your career.

Meeting summary:

(28:54) - Jason Knight asks Sandra Monteiro what makes a good mentor, and Sandra Monteiro lists qualities such as trust, respect, unbiased perspective, providing tools instead of solutions, and having a breadth of knowledge and resources available.

(33:23) - Jason Knight summarizes the conversation so far, highlighting the value of both informal and formal mentorship and the difference between internal and external mentors

(34:55) - Sandra Monteiro agrees that having both internal and external mentors can be valuable and shares her experience with a previous mentor who was also her manager

(36:06) - Sandra Monteiro shares that her mentor focused on providing tools and resources rather than giving direct solutions, which helped her develop her own solutions and rationalize her thoughts

(38:00) - Jason Knight emphasizes the importance of empowering mentees to make their own decisions and take action based on experience and resources provided by the mentor

(41:41) - Sandra Monteiro emphasizes the importance of honesty, trust, and openness to feedback in a mentoring relationship

(43:48) - Jason Knight explains that while there is an imbalance in experience, mentoring is still a relationship between equals with open communication and responsibility for one's own needs and goals

(46:21) - Jason Knight emphasizes the importance of open communication and feedback in a mentoring relationship, and the symmetry of responsibility for communicating needs and wants

More about Jason and Sandra

Jason Knight is a 22-year veteran of tech & product who has worked for big corporates and scrappy startups. He has been building disruptive B2B products for years and is completely in love with product management. A pragmatic idealist, he has long since realised that product management isn’t always like the books and is passionate about helping product managers, and product companies, survive in the real world.

By day, Jason is a product coach and consultant who works with startups and scale-ups to help them build great products and build great teams that build great products. By night he speaks to some of the biggest names in and around product management, as well as inspirational leaders, founders and practitioners on his podcast One Knight in Product. He’s also the co-founder of My Mentor Path, a platform that aims to make mentoring accessible to all.

Sandra Monteiro is the product Manager for Video at Sage Publishing, where she helps shape the future of Video streaming services for Higher Education in the Social and Behavioural Sciences, across Sage Video and Sage Research Methods Video platforms. She is also a plant collector, enjoys watercolour painting and urban sketching.

AI Transcript

Daniel Stillman

Welcome officially to The Conversation Factory. We're here to talk about all things mentoring. So I'm really curious how you sort of found yourself on the path of mentorship, like, why it matters to you, why you think it's important.

Jason Knight

Well, it's good to be here and obviously thanks for having me again. We'll talk about the other conversation another day. But it's a really good question, like the whole kind of path to mentorship and as with many of my life choices and general neuroses and all of the kind of drivers that I have, I think I can trace a lot of this back to dropping out of university, back when I was like 19 years old or so.

After one year, I'd worked so hard to get in, got to the bright lights of Liverpool and just realized that university wasn't for me. And going out and drinking and partying and being a heavy metal addict was absolutely my future at that point. I just kind of collapsed under the weight of the educational system and then ended up going back to Maidstone in southeast of England, my hometown, and kind of being a bit lost and not really with anything to do, and ended up taking a call center job. I took that call center job for two weeks. It lasted two and a half years before I got something else. But I was kind of in a bit of a slump at the time. And I was in a slump because really, I kind of felt that I'd failed and I didn't really know what to do with myself. And I was kind of just scattergun applying for any old random job out there. Admin assistant here, other type of admin assistant there. Like, I didn't really have a path or a plan. And the good thing about call centers is that you have quite a lot of diversity of different types of people.

Now, let's just call out we're talking about the southeast of England here, so not that much diversity in certain senses, but there are certainly a lot of different types of people coming through that place on a regular basis and ended up buddying up with a slightly older guy who we'd kind of just hang out. We'd go to the pub every now and then after work. And he'd had a bit of a career before, but then I guess himself falling a bit on hard times. And it really helped me to just be able to kind of almost lay everything out in front of this guy and just say, look, I don't know what to do with my life. I don't know what's good in my career, I don't know what my career is going to be. And he was really like the first, I guess, mentor that I would say I never called him that at the time, but the first experience I had of having a vaguely interested but still fairly neutral and totally uninvolved in many senses, basically friends that I could deal with. Now I don't know what he's doing these days, I'm hoping he's still okay. But that was kind of my first touch point and it really started to get me thinking.

But I'm going to emphasize over a very large number of years, but if we think about then my career, I spent quite a long time working in corporate. I originally was asked as I moved into leadership positions there, if I wanted to maybe do some mentoring within the corporate structures within the company. And I was like, well yeah, sure. I'd been about a bit by that time. There are other people that were more junior than me. And I started chatting to people in fairly structured mentoring sessions to try to help them with their careers and help them thrive and all of that good stuff at work. So that was my first introduction to kind of serious mentoring in the sense that it's actually something that's sponsored by a company and ends up being a real thing.

So I did that a few times for a few people, then moved out into the world of startups. And one of the things I realized, and I realized this in the worst way possible, because what I did was I went online a couple of years ago now, went on Twitter back when that was still a good thing to do. And I basically put a thing up like a tweet that basically said, hey product managers, if anyone fancies a mentor, why not drop a call in into my calendar? Here's my link and you can book me, we'll have a chat, I'll help you with whatever's on your mind.

And I was expecting two or three handful of people maybe give me a pity booking just to make me feel better. But I got 76 bookings from January through to April, like one a day. And I was like, wow, that's a lot.

Daniel Stillman

Now there's a hunger for it.

Jason Knight

Not clearly 100% there's a hunger for it. And I think product management is a very ambiguous role at the best of times. And there's a lot of people out there that maybe feel that they're not doing it right or that they're underperforming or that their company isn't doing it right. And a lot of uncertainty about whether product management is going well or what's okay, what's not okay. All of these things that mentors can help with. So I did a bunch of those calls, helped a bunch of people, hopefully. And that then really started me down the path of saying, well, hey, maybe we should mentor more people. And eventually to the point where I'm like, well, maybe we should set up a platform to help mentor people.

Daniel Stillman

Not surprisingly, you thought to yourself, how might I productize? Well, you have a systematic approach to things, right?

Jason Knight

Well, yes, although not as such. I mean, yes, obviously it turned out to be but at the beginning, it was very much like, wow, I've just helped 76 people, give or take. That was amazing. But I never want to do it again.

Daniel Stillman

It's a lot of context switching. It's not a time of your day.

Jason Knight

It's a lot of contest, which it was only like 45 minutes or an hour out of each day. And I did it around work, like, before work or after work. It wasn't a big burden, but it's a lot. And just seeing that kind of backlog of people into the future of all these different people, none of whom you know, none of whom you have any idea.

Daniel Stillman

So I'm gonna this is a really interesting point because it's a lot, but in a way, it was also not enough, because I love this idea of an interested but neutral party. And I think some of the gold and mentoring comes from not just having one person. I love that scene of you just finally having someone to unburden your like, this is what's going on. And when we all have these nonlinear pathways in work, like, M I okay, just being seen by another person is really powerful. But I think some of the golden mentoring comes from someone knowing you over time. Is that fair to say?

Jason Knight

I think it is fair to say, and I have to call out that maybe, technically speaking, what I offered these 76 or so people wasn't really mentoring, because a lot of them were one offs.

Daniel Stillman

Well, I don't want to take that away from you. I think you can't. Now I sound like a jerk. Oh, my God, thanks for calling me out. One call can have a lot of value, like just being able to just say what's going on. But I think some of the returns accrue because Sandra, who's going to be joining us in about 15 minutes, you've been working together with her for how long now?

Jason Knight

I think I've been working with Sandra for maybe two or three months to check when we actually started out. And yeah, I think that the return there is a benefit to the return. There is a benefit from the accrual of knowledge that you have about someone's situation and also, somewhat selfishly, the satisfaction of knowing that things change over time. Like, obviously, if you're having a one off discussion with someone, you give them the best advice you can, and they go off, and maybe you keep in touch with them, maybe you don't, but there's not like, a longitudinal element to it. Whereas when you're speaking to the same person repeatedly over time, be it through coaching or mentoring, obviously different sort of sides of a similar coin, I guess.

But the idea that you can basically check in and part of that checking in can be about accountability, like, hey, did you do that? But part of that checking in could just be, well, how's it going? How has your situation changed? And I think that that's one of the most powerful things of a more longitudinal approach where you're going back time after time. I don't think it needs to last forever. I think that there's a natural lifespan for mentoring. But at the same time, I think it is important to a have that context. It's like with chat GPT. Right? Like it remembers a certain amount of stuff. If you say things in the same window, then it will remember some of those things until eventually it forgets. But it ultimately can have a kind of a coherent conversation with you based on the stuff you told it before. And it's just that. But biological with mentors, you're sitting there saying, well, I remember that you had this problem last time. How's that going for you now? And oh, did you try these things? Well, maybe we could try this other thing. So yeah, it does compound definitely for sure.

Daniel Stillman

In our previous conversation leading up to this one about mentoring, we talked about one of the challenges being from a sort of platform approach is how lopsided the marketplace seems to be. And I'm wondering what you've done to I guess specifically, it seems like there's more people who say, I'd really love to get some mentoring, versus people who say, I'm going to carve out some time regularly for a person to do this. What have you done to try and equalize or industrialize the matching process? Because it seems like that's one of the one of the one of the barriers to having this happen more often.

Jason Knight

No, 100%, and just to kind of briefly resume like what it is that the platform that I've set up does. So we've got effectively a two sided marketplace of mentors and mentees, as you kind of touched on that's. Been going since about January, very slow burn. We're kind of growing organically at the moment because there's never enough time to put all the features in you want and we want to make sure that it's right. But yes, you've got a problem. Generally speaking, and this is something I saw last year before the platform was even a twinkle in my eye, when I ran a mentoring scheme with a friend of mine based out in the US. And basically what we did was we put a Google form up, basically circulated it in all of our social channels and said, hey, anyone to be a mentor or be menteed or be mentored, sorry. And there was good feedback or good take up of that, but ultimately we then ended up having to semi automatically match these people. I wrote some terrible Python script to kind of algorithmically match people together. And I'm being very charitable when I call it an algorithm, but there was a certain decision tree that was going on to try and get people and you're right, there were far more people wanted to be mentored than there were to do the mentoring. And I think that that's natural because a mentoring is massively beneficial to a mentee, it is also beneficial to a mentor, but maybe not in as many obvious ways, whereas for a mentee it's super obvious.

And also the lower down the career ladder you are, the more likely you are to feel that you don't quite have it all sorted out yet. And maybe a more wise old bird can come and tell me some of the things as kind of discussed before. So I do think it's natural for there to be a hunger, or more of a hunger for people to be mentored than maybe to be a mentor. What we've done with my mentor path, the platform that we're putting together and continuing to develop is we've encouraged people, for starters, to be multiple mentors. So rather than just Daniel stillman signs up to be a mentor and gets one person to be his mentee, great. But actually, if Daniel stillman has space in his schedule for four or five people, or two or three, then Daniel stillman is absolutely encouraged to do that. Because an hour a month or 45 minutes a month or whatever the session length that you decide to go with is that's not too much time. And if you can handle it, we definitely encourage that.

We also do encourage mentees to reach out to multiple mentors because obviously there's a certain there's differences. Like you can get differences from different types of people, different advice, different perspectives. Maybe if you want someone that's worked in your specific industry or certain types of stages of company or something like that, it's good to potentially get various different people kind of matched up with as well.

So we do encourage kind of both sides to search for multiple or make themselves available to multiple. And as far as I can remember, I'd have to check the figures. I think we actually, technically speaking, have more mentors than mentees available at the moment because of that kind of multiple, that suggestion of multiple. So technically speaking, we probably have fewer physical mentors, but because people are generous enough of their time that they maybe take two or three people on, then technically speaking, we have availability for a lot more. Now, obviously another solution to that is just to pour more people into the top of the funnel and get more mentors and mentees. But at the moment, that seems to be working pretty well.

Daniel Stillman

That's really lovely. And I think selling the value to a mentor, what are the challenge with getting people on boarded, saying, yes, this is worth giving your time to? Is there a mental model shift that has to be invited in them?

Jason Knight

Well, I think if we think about it, there's that kind of classic vitamin versus painkiller. I've translated it into vitamin for the American audience. Vitamin versus painkiller. You can use whichever of those you prefer. But in any case, there's this whole idea, and this is something, to be honest, that affects a lot of effectively well being or workplace well being, apps, this kind of idea that I really want to care about this, but at the same time I'm busy and also it's free, or it's free for me, and therefore the commitment is a challenge. Like people easily forget to do these things.

But I think there are benefits that are easy to espouse, certainly for the mentees. Like if you're a mentee, you can find a mentor who has more experience in your industry that's prepared to spend time with you and is prepared to give you the benefits of their experience to help you and encourage you to make progress in your own career. That's a no brainer in many ways. If you can find the time and if you can find the right mentor. I think if you think for a mentor, it could be considered a little bit lopsided, that arrangement in the sense that, well, I'm giving my time away for free probably to someone. Now I can do that because I feel good about that or because I want to pay it forward or because maybe even selfishly, I just want to feel good about myself that I'm helping someone. Like, these are all reasons that people could do mentoring.

But I think that there's also another thing that I don't know if you remember the film Interview of the Vampire or the book obviously as well, but the story of Interview of the Vampire where basically there's this concept that vampires have to kind of somehow stay in touch with the youth or with the zeitgeist to stop fading away. Like they need to continuously update themselves or they turn into fossils.

Now, it's not quite that dramatic. It's not quite that dramatic, obviously, but this idea that there's this kind of concept of reverse mentoring as well, where maybe a mentor, maybe a bit older, bit further in their career, maybe a little bit out of touch. With the day to day concerns of the average worker maybe gets a little bit back as well from mentoring people that are up and coming and sharing experiences and hearing about the problems that people in today's workplace that 1020 years behind them. I think that's incredibly valuable as well. But again, there is generally a there's there's a certain fluffiness to mentoring as well though, which is something that needs to be discussed, this idea that there's not like a concrete output of it often, sometimes there is. If you're sitting there saying, hey, I want to be mentored so that I can get better at public speaking or something like that and I need someone that's done that to help me or whatever, okay, cool. Like maybe if you then go and do a talk or something like that that you don't think you could have done before, maybe that's an outcome, maybe that's a concrete output. But a lot of the time it's more just a sense that things are better than they were before. But how do you measure that? And how do you attribute that to just mentoring versus all the other things that you're doing to develop your career?

So there isn't certain fuzziness around mentoring, but it doesn't mean that mentoring hasn't helped. I absolutely believe that it does. It's just part of the system. But when you're sitting there saying, well, I need to either do this thing that I really need to do or have that mentoring chat, it can be a barrier. I do think that we need to make sure that we enable people as best as we can to have those discussions, even if they have to postpone them, but to at least see that there is value in the concept of reaching out empathizing with people and just sharing experiences and hearing from people that maybe you haven't heard from before or hearing perspectives that you haven't heard from before and using those to develop yourself as well.

Daniel Stillman

It's a human output. It's human input. It's a human conversation. And what's the value of talking to a friend? So we only have a few more minutes before Sandra comes in. If we were to only answer one more question about mentoring, what should we dive a little more deeply into? What layers should we peel?

Jason Knight

That is a very interesting question. I mean, I guess one thing that people often ask about or maybe are unsure about is the difference between coaching and mentoring and where you'd use both of those things. And I think it's an interesting question because coaching and mentoring, obviously you're a coach, I'm a coach. They do share some characteristics.

Nice human discussions, possibly about goals, regular cadence, build up over time. So you've got that context and the kind of attention window from the past and stuff as well. So I do think that there are similarities, but there are also big differences. And I think a lot of the time when you see people talking about coaching online, they're really talking about mentoring. Because what they're effectively doing is saying that you need to have some person who's super credible in a certain space, like a person or a conversation designer or whatever that type of person is hypothetically. And hypothetically, whoever would have that kind of job, but then they're sort of sitting there saying, well, this person's got to come in and kind of share their experience and guide and train and all of these things.

Now, don't get me wrong, there's nothing wrong with guiding and training people, but it's not really coaching in the classic sense of the word. Like, coaching is all about actually using coaching skills to have great conversations and use all of the coaching techniques to reflect those back. And arguably, you don't even need to really be a conversation designer or a product manager to coach conversation designer or a product manager. I think that's an important distinction, whereas I think you'd find it very hard to be a credible mentor if you didn't have experience in the job or the industry or whatever that the person is being mentored in. And I think that's a big difference.

Coaching is a craft. You can think that that would be the thing, that the sort of thing that a coach would say. Sure you can think that, but coaching is a craft. It's a certain very specific set of skills in kind of Liam Neeson terms that gets you to an outcome in a certain way. And of course, there is always a chance for coaching to kind of blend into mentoring as well. I kind of call it centering. It's like the idea that you can kind of take different approaches, like the more directive approach of mentoring versus the less directive approach of coaching and do whatever you can to effectively get someone towards that goal.

Daniel Stillman

So it's like a little bit of a coach and a little bit of mentoring. Not centering with a man and a horse. Centering.

Jason Knight

Well, the original Mentor was actually a mythical character from Greek mythology.

Daniel Stillman

He was! his name was Mentor.

Jason Knight

Mentor was the tutor of Odysseus's son Telemachus. That's where the word originally came from.

Daniel Stillman

That is so true. That is amazing. So in a way, it's interesting because I think this is a very fine line of like, a mentor has to have some. We need to feel like they get us. And yet there's no way that you can have had the exact same experiences. And the industry may have changed a great deal in the intervening decades or whatever. And so there is a line between, well, I don't have the answer. So where is the switch between mentoring and coaching and how do you know when to grab for it?

Jason Knight

I think one of the most important things is if you don't have the answer, if you just don't know, then just call that out and be honest about that. Obviously it's great for a mentor to have effectively the answer to everything or an opinion on everything. But if you literally don't know, I think it's important to call that out and then maybe just explore it together. Now that exploring could be, well, you both go away and look it up and try and form an opinion on it. Maybe you go and ask Chat GPT or maybe between you, you just realize that we've got no skin in this game and I can't make a difference in this area. In which case, again, I think that one of the most important things about a mentoring relationship is that it's based on trust and openness and transparency and adds with coaching as well, obviously. But you should not be in a situation where you're basically lying to your mentee to make them think that you're clever. That's not a good outcome if you don't know the answer or if you're in a situation, as can happen, where the mentee is starting to require some other type of intervention, like maybe they actually need counseling. Maybe they need urgent support or something like that, realizing that as a mentor, you're not necessarily equipped to handle all of these situations and that it's your job in that case to get them to the right help as soon as possible, rather than somehow trying to work something out and potentially making it worse.

Daniel Stillman

We are not therapists. And to recognize 100% one of my past guests, Alyssa Rumsey, who's a registered dietitian and helps people with profound food traumas. There's still a line. We were just talking about it this weekend. Which is why it's top of mind of having a client who really should be in therapy and separate from the food coaching. And so if somebody's just literally in distress, right, some of that can be alleviated by just somebody who's been there before saying, yeah, it's going to be okay, and here's some things you can do. But some of that may need real support, real counseling support. So I think it's really important for us, to all of us to know our limits, which is really good.

Jason Knight

We need to stay in our lanes as best we can. That doesn't mean that we shouldn't experiment and push the limits of our shared understanding and all of those good things like we learn together. But we 100% need to stay in our lanes and realize when basically any intervention that we try to do could end up making things worse and that there are professionals that do these sorts of things for a reason.

Daniel Stillman

Well, speaking of staying in our lanes, I'm going to let defender.

Jason Knight

All right.

Daniel Stillman

Right on time, I believe. Sandra. Welcome to the Conversation factory. I'm so glad you decided to join us. I appreciate it.

Sandra Monteiro

Thank you so much for having me.

Daniel Stillman

Yeah. So I'm really curious if you can share a little bit of your own experience with deciding. Sometimes I think about jobs to be done with people in their lives, like the moment when we decide we need the thing and then the search to go and find it. I'm curious when you decided, you know what, I really need a mentor, and then how you found your way to Jason and working with him.

Sandra Monteiro

Yeah, well, it's a bit awkward, actually. I saw Jason until it took me as a mentee, basically. So when I first wanted to transition from I was a salesperson from sales to product management, I was looking for a mentor. And I wanted I i knew I needed someone that would help me, you know, do this transition, give me advice, how to do this, what should I do? And so basically, this was a few years ago, and I was looking online, how do I find a mentor? What is a mentor, basically? How can they help me? And I remember there were a few platforms at the time, but they were very exclusive. So you can join our platform if you have X amount of years of experience in product management, because we have very few mentors and this is very exclusive and it's not for everyone. So obviously I didn't make it into any platform, so I had to go through things without a mentor. And when I found my first job, I took my manager at the time as my mentor because she was this amazing person, super experienced. She knew everything about product management. So I took her as a mentor. It doesn't mean that she took me as a mentee.

Daniel Stillman

Can you say a little bit more about that? Because I've heard other people say this in the past of just treating someone as a mentor. It may not even be an official relationship. What does it mean to sort of just treat someone as a mentor in that moment?

Sandra Monteiro

I guess that my thing with her was that because she was so knowledgeable about everything and she was very kind with her time as well. So whenever I had a question, she was always there to answer it, and she was always there to help me whenever I came across any challenge that I didn't know how to work around. And I really deeply trusted her and I respected her. And I think that is the basis of any good relationship, is trust and respect between both. And when she left the company, I made sure that I kept that relationship going, even though she was not my manager. But she's still knowledgeable and she's still an amazing person and very experienced. So I think it stays the same way. I think I still look at her as my mentor, but she might not look at me as my mentee, as her mentee. So, yeah, I think that was one of the things. It's just trust and respect and being kind with the time as well. It's not like, come on, come on, we need to do this quickly. Let's set things up.

Daniel Stillman

I love this idea of informal versus formal mentorship. I'm really curious how you decided to how does one stalk Jason? What are the steps to stalking a mentor? Because this is clearly a nontraditional path to mentor acquisition. I think what you're saying is actually what many people do you're like? It's a wooing process sometimes, yes.

Sandra Monteiro

I don't know if that's what Jason would call it or just scary, but basically I was already listening to his podcast before transitioning into PM, and I really like the way that he, you know, the way that he interviews people, what he uncovers within these interviews and how he connects with people, how he's funny. I love that we have this kind of saying silly things and having fun with it. And I saw that he was invited to be a speaker at an event in London, so I made sure that I was at that event. And once I was there, I was just with my glass of wine, just trying to be cool and relaxed while being super nervous all about it. And I just went up to him and I said, Hi, I'm a fan.

Sandra Monteiro

And that was basically it. And I was following him on Twitter, on Link, LinkedIn. So again, stalking him, basically. And once I saw that my mentor path platform was on, I made sure that I was on that platform, and I was tweaking my profile, what can I do to make sure that I am matched up with him? But they have so many mentors available that I was being with a lot of people, and I assumed, okay, so he probably has a lot of mentees, so that's why I'm not being matched up with him. Again, LinkedIn. Chad, hi. Can I be your mentee? Do you mind being my mentor? And I said, fine, let's do it. And that was.

Daniel Stillman

It.

Sandra Monteiro

So stalking sometimes, persistence. Yes.

Jason Knight

I think I've realized why we're 100% matched on the platform now as well. I just thought that was a coincidence. But I think it turns out that you basically chose all the different settings until you were 100% matched. Makes a lot of sense.

Daniel Stillman

It's really brilliant. So, Sandra, what makes a good mentor in your mind, in your perspective? Because you've had a few now, what would you say are the qualities of a great mentor?

Sandra Monteiro

Yes. So this is my first official, proper mentor mentee relationship that has a structure. First of all, again, trust and respect. He is someone that I respected already. I knew something about his career and the way that he approached things and how he talked to people. And then as soon as we started this relationship and making it more formal, I also saw that I could trust him so I can be honest and open with him, and I know that he will be honest and open with me as well. Another thing that it's very important for me is the fact that he is unbiased. So he doesn't know my company, he doesn't know the people I work with. He doesn't know my overall context of things. So he's very unbiased. And especially when he's talking to me about things, I might be a little bit worked up when I have some kind of challenge, and I might be a bit more emotional. And he's very objective and clear and dispassionate about things. And I think that is extremely important because it also creates some perspective on my side, as in, it's just a job, let's be cool, be calm. We can work things through. Another thing that is really that I find really interesting is that he doesn't tell me how to solve my problems, or he doesn't give me the solutions. He gives me the tools so that I can find my own solutions and work my way through my own issues. So he always gives me examples of things that he went through in the past, in his previous jobs situations that are similar to the ones that I'm going through. And that not only, again, gives me perspective on things, but it also makes me realize this is not a me problem, it's not a me thing. This is something that happens with other people as well. So I'm not at fault here. It's just growing pains. And the way that we need to do that, we need to go about our jobs and life overall. And the other thing, apart from his own examples, is there is always material. So here's this book, just read through this, here's this Twitter thread. It's very interesting. Or check out this video because it also has some information around that. So I think that

Sandra Monteiro

the breadth of knowledge that he has and how quickly he is able to access that knowledge and share it with I find it really good and really helpful because it's at the time, it's not something that he will say, let me look through things, and eventually I will send you something that will help you. It's just I have this resources available that you can look through and I think that's amazing. I think that's really helpful.

Daniel Stillman

It's really interesting. There's three things that I've heard so far. One is the difference between and the possibility of informal versus formal mentorship and how both can have a lot of value. The story that Jason told before you came on of his first sort of informal mentor, where it's just someone you feel comfortable telling things to. The second sort of interesting tension you pointed out is the difference between somebody who is in your organization versus someone who is outside of your organization. And Jason hooked me up with his friend Talia, who predominantly builds internal mentorship programs. And it seems like, Sundry, you've had experience with internal versus external mentorship. I think there's a lot of value in having somebody who's internal because they know everything and there's a lot of value in having somebody who's outside of the organization and that they are unbiased and you can tell them more things without, I would think, any risk whatsoever.

Sandra Monteiro

Yeah, exactly.

Daniel Stillman

So in your estimation, is it a both and or is it an either or? If you had your druthers, I mean, obviously if you Jason's, you're forever a mentor, he's your ideal, but you've had internal versus external. If somebody else who's listening to this is thinking about either finding a mentor or being a mentor, which direction do you think they should direct their attention for maximum value?

Sandra Monteiro

I don't think it's an either or. I think it's perfectly fine to have both. And it can work to your advantage as well. Because, again, my previous mentor, she was my manager, so she knew exactly

Sandra Monteiro

I would be going to her for things that weren't directly related to what I was doing at that point and how to approach this problem or how to approach that specific stakeholder, or how to deal with this situation within the company, someone from outside the company. It gives you more of a holistic kind of approach. As in this situation, I would do this and this and that. So that is also something that I can take not just for my day to day job, but also if tomorrow I go to a different job, I can still take those with me because they're much more holistic and they are applicable to other situations. So I think that ideally have both. Why not?

Daniel Stillman

There's another point you made, and it goes to a question that Jason and I were trying to pick at, which is the line between coaching and mentorship and solving versus giving tools, examples, materials. Emotional distance, I think is another tool context in the industry. And yet we do want someone who's sort of been there, who knows, who's been along the path we've been before. So I don't know what my question is here. You are not going to get a solution from Jason. So what is my question then? How do you manage that for yourself? Because I think there is often in a mentee relationship, there's a desire for answers because you're coming with a pain, a problem, frustrations with a process. How do you manage that for yourself, your own expectations?

Sandra Monteiro

Yeah, so that was something that that's how I thought it would be. I thought that I would come up with a situation, a problem, and that he would give me the answer and I would be, hey, so this is the answer. I'm the best. And that never happened. Never. And from the first session that we chatted, he was always, there are these tools, there are this book, there are all these resources that you can look into, where you can find your answers. And there's also my experience, and I was in a similar situation in the past and this is what I did. But also the fact that I have to explain everything to him in the sense he doesn't know, he doesn't have the context. It forces me to bring my thoughts outside and speaking them out loud. So I have to rationalize things. I have to try to get some distance from it as well. And that also helps me create my own solution. So it was very organic. It was not something it said, I will not give you the solutions you need to find them. It was just the way that we built this relationship is the talking, the going through all the steps that I've been through, how I approach them, how he approached them and me seeing the difference between my approach and his approach and just trying to find out that middle term, like, the best for me in my specific to approach the problem again. So I think that was one of the things that I appreciate the most in this.

Daniel Stillman

It's really interesting. Oh, sorry. Go ahead.

Sandra Monteiro

Yeah, it's just I'm not telling you what to do. I'm helping you figuring out what you need to do.

Jason Knight

Yeah.

Daniel Stillman

So one thing I'm hearing, if you were to write a manual for mentees, somebody's thinking about finding a mentor, it sounds like one of your pieces of advice is come with a really specific problem, but also expect to be open about how it gets resolved because it's your job to find a solution.

Sandra Monteiro

Yeah, that is one of the learnings. Again, I know I've said it before, but I thought that he would solve my problem.

Jason Knight

I don't have any solutions. I don't really know anything. But I do think one of the most interesting aspects of and again, talking earlier about mentoring and coaching, which both share similarities and they also have differences, but I think that the sense of empowerment is the most important thing. Like, Sandra is not my puppet, that I can just kind of do the strings and just get her to do whatever I think is the right thing to do. And kind of almost like a father looking at his kids through trying to get them to play football because he can never do it or whatever. That's not the point. I very much see my role and the role of all mentors. That role is really to empower people to make the right decisions in their context and to make the right moves based on a combination, for sure, of experience. As Sandra said, this is what happened to me when I tried to do that. Maybe don't put your hand in that hole, and that sort of thing. But also then there's also some other stuff to back up. Here's some books that people who also got bitten when they put their hand in that hole, and maybe you should read those as well and just try and then inspire people to some extent to take action themselves. I think that's really where the sweet spot is, rather than just sitting there saying, right, Sandra, here's nine things that you have to do. Tell me next week if you've done them. Otherwise you've failed. That's not the goal.

Daniel Stillman

So what haven't we talked about that we should talk about? What's an important aspect of mentoring menteeing relationships and doing this dance between solving and asking, what haven't we talked about that's important to talk about? I'd be open for either of you to offer something.

Jason Knight

Trying to think. Feel free to step in. Sergeant, if you're looking for me to empower you.

Sandra Monteiro

I just want to reiterate that I think that the key to any relationship, any good relationship, is being open and trust, because you need to be able to trust each other if you're going to make this relationship work in the long run. And you need to be honest as well. It makes no sense for me to be talking to Jason and saying, so I've achieved this and I've done that. When it's a lie, it doesn't help me and it doesn't help anyone, basically. So being just honest, I think honesty is very much the key. And also being open to feedback. There was this session that we we had a couple of weeks ago when I was very keen and working and I want to do this and I want to do that, and he just asked me why, and I was like, I don't know. Well, then maybe you should find out the why. And I said, great feedback. Yes, maybe that's something that I really need to work on. So also being open to the feedback and not just taking just thinking that everything is just very nice and perfect, you need to receive the feedback as well for things that you might need to improve and also give the feedback. If something is not working between us, I need to be able to tell him this doesn't work. This is not being helpful in any way so that we can work on that and improve the relationship.

Daniel Stillman

This is a really valuable point, Sandra, because this idea of like, oh, it's just going to be all these endless stream of amazing tools and solve problems with wonderful perspective. And sometimes the reality is you're going to hear something that maybe you don't want to hear or you're going to be asked a question that you don't feel comfortable answering yet and walking into the conversation with that expectation. Jason, do you want to say, it sounds like you were nodding your head? You remember that moment?

Jason Knight

It sounds like, yeah, I do. But I think also there's an even more important point I was thinking about as Sandra was talking, is this idea that whilst there is a certain, I guess Imbalance in a mentoring relationship, in the sense that obviously I'm the one giving, for the most part, the, let's say, advice or the places to look, that it's still very much kind of a relationship of equals. Right. Like, I'm not sitting here as Sandra's boss or her better or anything like that. That's not what mentoring is. Mentoring is all about kind of co creating the future that you want to have whilst obviously accepting that one of the people has in that partnership is more experience in a certain area, which means that they naturally have more to bring to certain parts of the conversation. But it's still very much a conversation between two equals that are trying to get to some kind of goal, which is ultimately one person's goal. Like, Sandra has goals. Those goals are not ultimately my goals. If Sandra decides that she's had enough of me, then she will continue towards those goals and I will not. So it's not up to me to live those goals. It's up to me to do my best in the time that we have together to help her towards those goals and try to inspire action in certain areas and point me in the right direction and give the benefit of any experience that I do have. But again, it's not that I'm either the puppet master or the boss or the superior or anything like that. This is a relationship between two equals where just one person has more context and the other person has maybe more breadth.

Daniel Stillman

Anything you want to add to that, Sandra?

Sandra Monteiro

No, I agree with him. It may come a time where I'm just, hey, Jason, this is not working anymore. Let's stop this. It may not happen either.

Daniel Stillman

Well, in my coaching training, one of the things that I try to hold in the space is this is one relationship where you should never have to guess where you stand, and that openness to feedback that you pointed out. Sandra is something that there is some asymmetry, I think, both in the coaching and also in the mentoring relationship. But the symmetry is that we're both choosing to be here. We can both leave at any time, but we're also responsible for communicating what's going on with ourselves. Right. I think one of the things that people are so ghosting is something that happens on online dating, and it's awful to be ghosted by someone. It's terrible. It feels terrible. And this is a relationship where you don't ghost. You say, hey, this is what I'm not getting, or this is what I'd like to get more of, ideally before you get to this is what I'm not getting. So I think that the symmetry is in the expectation of feedback and open communicativeness of needs and wants and goals. So I think that's really the asymmetry isn't that Jason's problems in the conversation are less important than Saunders problems.

Jason Knight

Right. My problems are generally less important than most people's problems. So we should just accept that.

Daniel Stillman

We just have a couple of moments left. Anything else that we haven't talked about that we should talk about, sandra around what makes a great mentor mentee relationship or how to think about it, especially from the mentees side.

Sandra Monteiro

I don't know what you've covered before, but I think that it's just that it's important for people, when they're looking for a mentor, to be clear on what they are looking for, but also to be patient, because you don't necessarily find the mentor at your first. That might just not be the person that you are looking for for whatever reason. Maybe there's just no chemistry, or maybe it's just the experience that is different, or maybe it's just a personality issue, maybe a million things. Just be patient. And if it doesn't work, it doesn't work. You just need to do what's best for you in relationship and just try and find someone else that might be better for you. And if you're on the side that you're being refused, just don't take it personally. It needs to work for both sides regardless. So I think that is important. If it's not working for you, then it makes no sense to invest the time on it, and it might be better for both parts to just start over.

Jason Knight

Yeah, I had some feedback recently from a couple of people that used the platform that were like, I really don't like that button that says end relationship, because it just sounds a little bit too harsh. And I'm like, well, okay, maybe we can come up with some fuzzier words. But at the same time, Sandra's point is really valid. Like, sometimes even the most matched on paper, two people that have maybe they've worked in all of the same types of companies, they've basically got very similar career paths. They're from the same part of the world. Like, all of these different things, they could look like brilliant mentor mentee relationships on paper. But actually, you look at it and you're like, well, actually, we had a chat. We just didn't like each other. We didn't click, we didn't get on. We couldn't find enough common ground for this to be a productive relationship. And we could kind of just tell. Now you've got two options there. You can either try and soldier on, because, like black mirror, we've been matched together and somehow that's now our future, or you can sit there and say, well, okay, fine, let's move on. As Sandra says, no harm, no foul. It didn't work out. There's plenty more fish in the sea from both sides. You can go and find another mentor. You can go and find another mentee, find someone that's going to help you, and don't be afraid to. I mean, look, you should always give people a chance. Like, if you're halfway through a mentoring relationship, like, maybe you're sitting there three or four sessions in and you're like, oh, well, that last call didn't go very well, then maybe there's something that can be corrected. But if you're just sitting there up front and saying, I just don't think this person gets me, or I don't think there's enough commonwealth, just move on. I think it's important not to get too hung up and feel like you're hurting people's feelings. Sometimes it just doesn't work out. Yeah.

Daniel Stillman

And Jason, if you could place a billboard on the A one to encourage more people to like to to jump into the pool and to start mentoring more, what would you what would you want to put on that billboard? To to get people.

Jason Knight

To be a.

Daniel Stillman

Mentor to be a mentor, to start to start doing it more? Yeah.

Jason Knight

You'Ve probably had a lot of support in your career, or maybe you haven't and you wish you had, but in either case, take a leaf out of the book of the person that you wish you could have been and start to pay it forward to the next generation. 100%. Sure. That scans I kind of made it up as I went.

Daniel Stillman

No, that's really on those lines.

Jason Knight

This idea of being I've literally never said that before.

Daniel Stillman

No. The idea of being the person you wanted to have had, even if we didn't have that person and there's a lot of people who feel like I've just bootstrapped myself. There's a possibility of paying it forward 100%. That's really beautiful. We are at time. I'm really grateful that both of you made time for this conversation. I think the mentor mentee relationship is a really special, very powerful conversation patient that's worth doing well. So I'm really glad you both came on to talk about it.

Jason Knight

Thank you very much for having us. And I'm going to go get that restraining order now for Sandra as well.

Sandra Monteiro

Thank you so much.

Daniel Stillman

All right.

Jason Knight

Thank you, Sandra. Thank you so much.

Daniel Stillman

Jason. Be well.

Jason Knight

Thank you. All right.

Sandra Monteiro

Thanks.

When the Mission Drives the Tech: Co-Founder Conversations

It’s not every day that a patient-doctor relationship turns into a Techstars-Funded medical innovation startup. In this episode I sit down with Dr. Onyinye Balogun and Eve McDavid, the co-founders of Mission-Driven Tech, a women's health venture in collaboration with Weill Cornell Medicine dedicated to the transformation of cervical cancer care with modern technology.

Onyi, as her friends call her, is the CMO of Mission Driven Tech and also an Assistant Professor of Radiation Oncology at Weill Cornell Medicine specializing in the treatment of breast and gynecologic malignancies and does research into improving cancer care in low and middle income countries.

Eve, the CEO, is a former Google executive who is also a Stage IIB Cervical Cancer survivor. Eve and Onyi met during the pandemic, when Eve was undergoing cancer treatment under Onyi’s care.

I heard Eve and Onyi’s presentation at the 2023 Techstars Demo day in New York and was stunned by the fundamental disparities in historical improvement in gynecological cancer outcomes - as they point out in this conversation, in recent years, Prostate cancer treatment has achieved a nearly 100% five year survival rate. In the same period, cervical and uterine cancer mortality has gotten worse, while cancer treatment for all other cancers has improved exponentially. Their company exists to change that story.

Co-Founder Communication Insights

This conversation is one of a series on co-founder communication. Check out my interviews with the co-founders of online gaming start-up Artie on Pivoting while staying sane (the secret - have a coach and a therapist!), a conversation with Carolyn Gregoire and Scott Barry Kaufman, the co-authors of the 2015 bestseller, Wired to Create, on navigating Paired Creativity, and this interview with the co-founders of collaboration tool Range, Jennifer Dennard and Dan Pupius, on the keys to healthy conflict. One key that Beth Bayouth and Mario Fedelin, the COO and CEO (respectively) of Changeist, a non-profit organization dedicated to youth empowerment, discussed was the importance of co-founders sharing how they are really doing so that they can be sure to not fall apart at the same time, a sentiment that Eve and Onyi echoed.

I also discussed the idea of “prototyping partnerships” with Jane Portman and Benedikt Deicke, co-founders of Userlist - and they helped me see that the healthiest companies have partners that have worked together in some capacity - and indeed, in this interview, Onyi and Eve called Eve’s cancer treatment their “first collaboration”.

Know yourself and each other

The start of a startup journey can be optimistic, so we explore what they have learned about each other that has helped them to better communicate and collaborate together since they started the project.

Accelerators can’t do it all for you

Eve and Onyi share how the accelerators can help with structure, mentorship, capital and community, but that ultimately you need to have something worth accelerating - a key customer insight or a core technology - both of which Mission-Driven Tech has!

Have multiple modes and frequencies of communication

Eve and Onyi have a weekly meeting just focused on their flagship product, the Blossom device, and another meeting weekly for other issues, and to simply connect. Meanwhile, they have a Whatsapp thread that enables them to constantly stay connected and in touch with each other. Balancing always-on connectivity and scheduled connectivity is key.

A partnership is a marriage and reflective listening is key!

Onyi shared their perspective that being in a co-founder relationship is like marriage, and that communication is key for any marriage to work. As she says, “The future of this company rests partly in how well we're able to communicate. So we tell each other the good, the bad and the ugly.” She shared their simple and effective approach to communication - making specific time for it, and using active listening intentionally:

“I hear what you're saying, I reflect it back to you. You hear what I'm saying and you reflect it back to me.”

Know who your real audience is

We discuss user-driven product development, which Eve and Onyi, as a former patient and doctor, are a unique example of…but we also discuss how in their current stage, investors are their actual “buyers”. Onyi discussed how she’s developed a keen sense of “push vs pull” when they are making their investment pitch - some investors just get the commitment required to make a startup like this successful, and those people are their real audience. It’s not about convincing the wrong people, it’s about finding the right people.

Balance Now and Next

Every startup needs to balance managing their current challenges and opportunities with putting energy into strategic vision and planning. Eve points out that this is a particular challenge for medical and device companies - the rate of change can be slow, due to fundamentals of the problem space. So, there needs to be more patience and intention put into planning and hypothesis testing. As Eve pointed out, There is immense pressure to achieve immediate results, but real impact takes time.

Links, Quotes, Notes, and Resources

https://missiondriventech.com/

LinkedIn:

Onyi: https://www.linkedin.com/in/onyinye-balogun-md-ms-22b57283/

Eve: https://www.linkedin.com/in/evemcdavid/

AI Summary

Eve and Onyi collaborated to improve medical devices for cervical and uterine cancer treatment, driven by a passion for improving women's health outcomes. Mission-Driven Tech aims to provide a less painful medical device and raise awareness to improve equity in outcomes for gynecologic cancers. Eve and Onyi emphasized the importance of finding aligned investors and noted the slow process of change in medicine.

Key Points

(3:02) - Onyi points out that The Techstars accelerator provided scaffolding, capital, mentorship, networking, and connections to investors. They learned that accelerators cannot do everything for you and it's important to have critical mass for acceleration. They also discussed how they met through Eve's cervical cancer diagnosis and treatment, where Onyi was her treating radiation oncologist, and this was their first collaboration.

(10:41) - Eve and Onyi discussed their collaboration to improve medical devices used in procedures for cervical and uterine cancer treatment

(12:57) - Eve's persistence and passion for improving the devices and their shared a belief in wanting things to be better in women's health led to them founding the company

(19:38) - Women's survival rates for cervical and uterine cancer have worsened since 1970, due to underfunding and lack of awareness

(22:45) - The startup aims to improve equity in outcomes for gynecologic cancers by providing a less painful medical device and raising awareness

(30:15) - Eve discusses the slow process of change in medicine and their goal to have their device approved for use in clinics globally

(41:22) - Eve discusses the importance of finding investors who understand the impact of their capital and are aligned with the mission, and shares their success in identifying those investors through conversations where they see people lean in and their eyes open

(45:47) -Onyi notes that when someone is for you, they get it, and even when they say no, it's better than a maybe

More About Eve McDavid and Dr. Onyinye Balogun

Eve McDavid is the CEO and Co-Founder of Mission-Driven Tech™, a new women's health venture in collaboration with Weill Cornell Medicine dedicated to the transformation of cervical cancer care with modern technology.

Eve is a Stage IIB Cervical Cancer survivor and former long-time Google Executive who uses her expertise in tech, business & media to fight for change in women's health. She is a passionate advocate for women's healthcare access, literacy and equity and has been named an expert in survivorship and innovation by the World Health Organization. Her story has been featured in The Washington Post, Insider, Thrive Global and ABC-7.

Dr. Onyinye Balogun is an Assistant Professor of Radiation Oncology at Weill Cornell Medicine specializing in the treatment of breast and gynecologic malignancies. She is also the Co-Founder and Chief Medical Officer of Mission-Driven Tech. Onyi is a graduate of Harvard University and Yale University School of Medicine. Dr. Balogun initiated her residency training at the University of Chicago and completed her final year at New York University.

She has conducted and published breast cancer research in novel therapeutics for triple negative breast cancer and brain metastases. She is also engaged in gynecologic cancer research as well as global health activities with a focus on improving the delivery of radiation therapy in low and middle income countries.

Full Transcript

Daniel Stillman

So I will officially welcome you both to the Conversation Factory. Eve McDavid, Onyinye Balogun, thank you so much for making the time for this conversation…I really appreciate it!

Dr. Onyinye Balogun

Thank you for having us.

Eve McDavid

Great to be here, Daniel. Thank you.

Daniel Stillman

Thank you. And by here, you're where you are, I'm where I am. We're here in a digital space, but you two are together, which I think is nice, actually, to have you not separated by the Brady Bunch window, which is great. How much time do you two spend together versus in your bubbles or in heads down work in your own just I'm kind of curious.

Dr. Onyinye Balogun

Yeah. So it mean. I think we just were part of the techstars. New York City powered by Morgan Cohort So we were together for chunks of hours at a time, at least like twice a week or so. That was kind of more intensive time that we have spent together compared to a lot of remote work has happened since we've partnered. But yeah, so I think we found that we liked spending time together, which is always good.

Daniel Stillman

It's always nice when you like that.

Eve McDavid

Since that's one part of absolutely. We do really well when we get together and we sprint and then we're able to work remotely on asynchronous sort of items and projects and things like that. So we do a mix together.

Daniel Stillman

This is so interesting because I feel like the dynamic of the co founder and how work happens and how conversations happen is so individual and very nuanced. So now that you're not in Techstars, how do you feel like you're structuring your time together?

Dr. Onyinye Balogun

Yeah, so, I mean, prior to Techstars, we know the importance of touching base regularly, so at least once or twice a week we have a meeting for the hardware tools that we're developing, or the engineering meeting, as we call it. And then we also would have a weekly sync where we just check in on various items. And of course, there's real time texting and talking. But prior to Techstars, we definitely knew that we needed a regular working times and meeting times. So that was already established. It just got amplified with the accelerator.

Daniel Stillman

Yeah. I'm curious and we're just going to meander, but what would you say were some of the biggest things you got out of being in that accelerator?

Eve McDavid

Yeah, one of the great opportunities of an accelerator is that it gives a startup scaffolding. So all the resources that a startup frankly needs, the oxygen it needs to grow, to build and to grow. So there's capital, there's mentorship, there's networking, and then there's connections to investors on the other side. We have been really fortunate to participate in two different versions of two very different types of accelerators. We were part of a program at Cornell Tech this past fall that is intended for typically academically driven founders who are now commercialize technology that they've created in their academic careers and bring it out into the wild. And what does that path look like going from academia into a commercial environment, then Spring, we had a very different experience in a commercial environment with Techstars that was very much akin to some of the environments I've worked in previously. In Tech, where there's a really singular focus, everyone is there building a software product, and all the companies are fairly similar in terms of either their staging or their needs or their resources or things like that. So the accelerator we have found is a great way just to put a little bit more structure around the startup as we're building it and figure out what is it that we're specifically looking for, how do we identify those needs within this program, whether those be actual people or specific resources, and then get what we need to keep going.

Dr. Onyinye Balogun

Yeah, and I think one of the major takeaways one was it's good to have more face to face time in this era. We definitely work well remotely, but there was a flow, a synergy that happens when you come together. So I think that's one of the things we got from it. Two is, of course, the capital that was invested. Three were the other founders. Just seeing their drive, their brilliance, the success that they've had since. That has been inspiring. And then finally, I actually think one of the biggest lessons I got was they cannot do everything for you. And that's actually something I, someone else say on a recent podcast, love podcast, they said, do not expect the accelerator to do everything for you. They can take you a certain distance, maybe provide certain things, but they cannot do everything for you. So I think that's one of the takeaways from the experience.

Daniel Stillman

That's so interesting. I'm a former science nerd, so I'm just thinking of F equals Ma. And of course, acceleration is dependent on another variable. You got to have the mass.

Dr. Onyinye Balogun

You got to have the mass, right. You got to have the critical mass. Which way is that acceleration going? Are you decelerating? Don't get me into no.

Daniel Stillman

As you know, I assume well, you may both know this, but the acceleration is the derivative of velocity. It's the rate of change of velocity is acceleration. But the rate of change of acceleration, there's a unit for that. It's called the jerk. The jerkiness of something is the acceleration is changing too much. It's one of my favorite physics fun facts. Completely.

Daniel Stillman

Well, thank you. Maybe not irrelEvent to our conversation because you want to be able to grow at a pace that you can sustain.

Eve McDavid

Yeah, absolutely.

Daniel Stillman

I would say mildly obsessed with the question of how two people meet in this topsy turvy, mixed up world. And it's like hearing somebody's story of how they met in a romantic relationship. I find them fascinating. And this is like the co founder relationship, I think, is beyond a romantic relationship. It's much more complex and deeply entangled. And I'm wondering if you can take us back to the early parts of the conversation. Would you two today and the two of you at the beginning recognize each other?

Dr. Onyinye Balogun

We've never been asked that question.

Eve McDavid

Yeah, that's a good one.

Dr. Onyinye Balogun

That's a good one.

Eve McDavid

Yeah, I think from an ideological standpoint, yes, we would recognize each other. Yes, absolutely.

Eve McDavid

Yeah. Okay, you can tell them this story. This story.

Daniel Stillman

So for those of you listening, on Union did like very hard air quotes.

Eve McDavid

Okay, well, buckle up. It's really good.

Daniel Stillman

Yeah, it's an intense story.

Eve McDavid

It is. That's right. So we are here today because of the extraordinary care that I received when I had a cervical cancer diagnosis three years ago. Onyi was my treating radiation oncologist. And there was a combination of the best medical care that's available in the world that Onyi, as a physician, can administer in a really sort of just in time capacity because there was a lot of stuff going on. I was pregnant at the time of my diagnosis. I was being treated in New York City for both the delivery of my son and for cancer treatment. And then the sort of big sort of explosion within the explosion that happened at the time was that the pandemic started in the middle of treatment, and it was at the beginning of the end of treatment. But it's also the most intense time of this type of cervical cancer treatment called brachy therapy, where a patient has five internal radiation procedures administered over the course of a two week period. And the care windows are really tight, so the care has to be delivered at a very specific time so that the patient is able to receive a very specific dose of radiation so that she's able to effectively have her disease cured. And even in the throes of a global pandemic, where other providers had to make really difficult choices about care that they would continue or not, Onyi kept going and kept and I'm just good. She's stubborn and I'm really good at following the rules. I showed up and Onyi showed up, and we did it together.

Dr. Onyinye Balogun

Yeah, that was our first collaboration.

Eve McDavid

That was our first collaboration, exactly. And what happened in terms of how we put our heads together around this. So these procedures are incredibly important. They cure cervical and uterine cancer, but they are also nearly possible to endure because they're so incredibly painful. And before my first procedure, Onyi let me know that this was going to feel like childbirth, that's how painful it was going to be. And I thought, well, one, that's really scary, but two, this is like a really strange thing that my doctor is letting me know. Something that's about to happen is about to be so excruciating. What is going to happen and why is it that way and how does this go? And so at a point during treatment, we started talking about the medical devices that are used to administer these procedures. The medical device brings the radiation source right to the tumor so that you can have a really hyper targeted, very focused radiation dose and spare the surrounding tissue and organs that are really important in the pelvis. And it turns out that the medical devices are from the early 1970s. They were designed 20 years before women were included in clinical trials. They were never properly designed to properly fit a woman's anatomy. And so you have physicians who are the best in the world at this practice, in the craft, who are using a tool from 50 years ago. And at the time I'd been in an executive function at Google and I'd seen great technology and some of the best technology in the world. And so I was like, I don't understand. What do you mean that in cancer, the tools are so dated, this doesn't seem right. And so we put our heads together on what a better design for that radiation device could look like. And by just beginning the process of what could this be and what could this look like, we really realized that this is a field within women's health that hadn't gotten much love in many, many years and was really due for an update. And from Onyi's incredible clinical expertise and my lived experience as a patient, we put our heads and our backgrounds together to start to make a change here.

Dr. Onyinye Balogun

I think one of the key things know Eve is still being treated, right? It's a pandemic, right? She's still know a couple of treatments of this internal radiation procedure called Brachytherapy. And Eve is asking me all these questions. She's like Onyi, do you think this could be done better? Do you think these devices could be improved? And I was like, I'm trying to take care of your cervical cancer. You have all these questions. You're asking me to see the device. It's great, but I want to focus on preserving your life, getting you back home to your beautiful children, to your husband. We said, let's get you to remission first and then we'll talk about the devices. And sure enough, after her first, I think even at your first visit, after you finished treatment, you were still like, hey, can I see those devices? And it was her persistence, I think, when she first asked me, I said, I know this can be done better. You feel as a physician as though you're not 100% happy with how things are, with the status quo, and you know, in the back of your mind this can be better, but you have so many responsibilities, so many duties, how do you find the time to act on that knowledge that's back there? So it kind of like took Eve, who I think is the catalyst, as we thus to nerd out science a little bit. Eve was the catalyst that activated this because she was so persistent and passionate. And when she came and I said, sure, at a follow up visit, let's look at these devices. And it just went from there, the collaboration. So I think, as we were saying, ideologically, we are still similar. We're dreamers. We are aspirants for people who are not satisfied with, well, that's just how we've done things. So I think we've that core belief of we want things to be better, especially as it pertains to women's health. That's our passion. That's our calling. That's what brought us together.

Daniel Stillman

Yeah. This is so interesting to me because obviously you've been in this problem space for an exceedingly long time and have thought these aware of the limitations and the challenges. And you have to say, like when you said the you said 50 years, I was like, oh, God, that's true. It's a hard number anyway, just pausing over that. Yeah, I mean, hip hop just turned 50, 1973, which is just crazy. So it is really interesting that you'd thought these thoughts and were aware of the challenges. I presume had noodled on this, but you needed a little bit of a catalyst. If you're the active ingredient, you're the reagent. In this analogy, you had some pent up activation energy ready to release.

Dr. Onyinye Balogun

But I think this is the case for a lot of physicians, right? You get caught up in the day to day. You know, I think this could be better. I know that could be better. But they're pressing things the immediate right. There are immediate things that have to get done. And I think a lot of our time goes to that and rightfully know, seeing people writing the notes, making sure orders are in, doing the procedures. But one of the things that really helped us was being part of Wild Cornell. In addition to having Eve as this catalyst and persistent and passionate. And we could see that we both wanted this to improve this device. While Cornell has an ecosystem, they nurture entrepreneurship. And I think that was one of the things that really helped us because it's kind of like, how do you yes, I know something needs to be done, but what are the next steps? And being at an institution that nurtures innovation, that says, okay, come and do this program together, that was key. So we were part of ICORE. We were part of this BioVenture e labs at Wild Cornell. And one of our proudest moments is we were just getting started in this and they had a competition. And so we looked at each other, we were like, we really can pep, like, talk each other like nobody's doing this at key events. And so we were like, we're going to win. Yeah, we're going to win. Yeah. So we go and we give what we hoped was a phenomenal pitch and then it's time for them to announce the winners. And so they called one group and we were like, oh, okay, fine. And then they called another person who won because they said there was a two way tie for second. And we were like, oh, that's interesting as well. And I think we both did not think we had won the competition. And so when they called the third group's name, we were just cheering. We were like, yeah, good for them. And then we realized it was our name, and we started we were jumping up and down.

Eve McDavid

I don't think anyone had ever said our company name other than us in public at that point.

Daniel Stillman

It's a thing.

Eve McDavid

Good for them.

Dr. Onyinye Balogun

And it dawns on us that it's us. And I think that was a moment in which we were like, we can do this.

Eve McDavid

Yeah, we can do this. Absolutely.

Daniel Stillman

So can we talk about mission driven tech and around the challenge of eve, I remember your presentation, both of your presentation during the techstars pitch day, where you're talking about some of the major challenges in the numbers looking at a women's gynecological health. So for those people who are listening, who do not know this situation, could you paint why this company, why your mission is important and the challenge that you're facing here, that we're all facing here?

Eve McDavid

Yeah, absolutely. So I'll start and then the clinical data, I think Onyi really your vantage point here is so important. The data that we see globally for two cancers that specifically impact women, cervical cancer and uterine cancer, women's survival rates today from those two cancers and cervical in particular, which is preventable, treatable, curable survival for those cancers today is worse in 2023 than it was in 1970. And when you look at all cancer survivorship since the 70s, that entire field has advanced exponentially. But these two cancers that specifically affect women that are gynecologic diseases are going in the opposite direction, and that is incredibly alarming. But when you start to double click into this field of women's health and then gynecologic health, and then you get into this field of an overlap of sexual health and public health and oncology, it all starts to make sense. These are fields of cancer research that have been underfunded, underinvested, in, and the layperson with a cervix. The lay woman on the street has very little general education and knowledge and awareness that she has a cervix. It's an organ that oftentimes and does get sick from a common sexually transmitted virus called the human papillomavirus, and that it is a normal part of her overall health to have preventative appointments and screenings to make sure that infection clears on its own versus turning into a cervical cancer diagnosis. So there's a really sort of big problem within a problem. And we started to look at the entire care continuum of cervical health, realizing that our innovation in treatment was just one part of the problem we're trying to solve for across this entire care continuum that includes prevention, intervention, treatment and survivorship and you can't solve everything at once. So as a startup, you have to pick one area of focus and do that really well, which is why we started with the medical device. And so once that work got underway and on a path and we can talk more about where we are in our development work now, we realized, okay, it's going to take time for that to get to market. So how do we also do work across this entire care continuum to draw attention and investment and awareness and research to this field so that we can advance the entire field forward?

Daniel Stillman

Anya, you want to put some more color on that?

Dr. Onyinye Balogun

Yeah, absolutely. And I think one of the things that's really important to us.

Eve McDavid

Is just.

Dr. Onyinye Balogun

The question of equity, right? We are a black woman and a Caucasian woman together working on this. And we know that Eve talks about it. She had incredible care, she had incredible outcomes, but that's not the case around the world. And we believe that one of the things that we can do to improve the equity in terms of outcomes for uterine cancer, for cervical cancer, one of the things we can do is provide this device so that women are not afraid to undergo the procedure. The procedure is very painful. And we have a patent right now, an international patent for a device that we believe will decrease the pain, improve the patient experience, improve the physician experience, because you feel awful when you're causing the individuals that have entrusted you with their care that you're causing them so much pain. So by doing that, we hope to also narrow the gaps in terms of racial disparities in these cancers. Also by just drawing attention to the issue itself. It's so taboo to talk about sexual health, to talk about women's health. They're all interlinked. And I think that and shouting it a mystery is part of why women don't come in early enough for treatment. And that's why part of our work is to amplify these issues to talk about. Look, cervical cancer, uterine cancer, they exist. Make sure you go for your screenings, make sure you present early if you have symptoms. So that's all part of what we're doing because right now we should not have 600,000 women a year being diagnosed with cervical cancer right now. We should not have mortality rates for cervical cancer and uterine cancer going backwards. Do you understand that in the same time span, prostate cancer has now moved to nearly 100% five year survival rate? In the same period of time that cervical cancer and uterine cancer mortality rates have gone backwards. Men diagnosed with prostate cancer in the United States can basically expect to survive at least five years. And that inequity should not be it just shouldn't.

Daniel Stillman

Yeah. So what happens during Gynecological Awareness Month? What should be happening? What is the process of how do people get involved? What are you all doing for September that will move the needle from your perspective?

Eve McDavid

Yeah, that's a great question. So you can look at a starting point of awareness for Gynecologic Cancer Awareness Month by looking at search trends on Google. So if you were to compare searches for Gynecologic Cancer Awareness Month relative to Breast Cancer Awareness Month, and it's not a leaderboard, right? Like it's a North Star, it's not a leaderboard. Right. There's no ranking of their winning. I think they've done a great job and they've created a great model. Yeah, the pink ribbon. I mean, everything pink, right? Like corporate sponsorships. And we're comfortable saying breast cancer, right? You couldn't say breast cancer before. Right. So you had leaders, men and women, you had people in positions of power who had capital to draw on the attention of policymakers of research institutions that, again, created a tremendous amount of awareness and research and funding that then helped drive these fields forward. Same thing happened in prostate cancer over the last 30 years. And so we look to those two different disease states as these are great models for what happens when people know about them and when people are comfortable talking about them, and then people have the ability to act and bring others into the mission with them. So for gynecologic cancers, of which cervical and uterine are a part, that awareness is very small. There are zero searches relative to, say, breast when you look at the data on Google. And so we want to make it easier for women to realize, okay, this is a time during the year where we want to make it more comfortable than maybe it was last year talking about this. Encourage women to make sure that they're up on their annual, well, women's visits if they are having concerning symptoms or anything that they want to discuss, that they're not nervous or anxious or uncomfortable having those conversations with their providers. It's just a great time to check in with yourself about are you up to date and when you get into those care appointments, are you getting the questions that you have answered and are you receiving the care that you need? So we're really excited about this time because it gives us all an opportunity to have a conversation about gynecologic health and staying up on care and handling any required interventions in a timely and safe manner as best as possible.

Daniel Stillman

Yeah, well, so I do want to shift gears because you talked earlier about strategy and your roadmap and what you built first versus what you want to build next. And I want to pull back to the next two or three years of your evolution as a company and how you think about the road ahead. I think one of the biggest challenges that every startup faces is managing the present right. What the opportunities that the world's throwing at you versus just being sort of like reactive and proactive with things that yesterday and has put on our calendars versus being really strategic and creating what we want to create and just moving through that energy field of what the world's throwing at us and all the things we could do versus the things that we really, really want to do. And I'm just curious how you manage reactivity versus proactivity versus strategy in your dialogue. Right? Because there's a lot of signals and a lot of noise you have to parse through on a day to day basis.

Eve McDavid

Yeah, absolutely.

Daniel Stillman

We can't wait for it to be a double blind. You can't wait till the data is perfect for us for you to act on a sort of like weekly, quarterly basis.

Eve McDavid

No, I think what you're describing is every challenge of every company and especially every young company. How do you do the right now? Really well. So you're setting yourself up for a great future and in medicine and Onyi talks a lot about like change is slow and it's slow for good reason. We're talking about humans who are the recipients of advancements in technology. And so it's slow and it's deliberate for good reason in two to three years time, from a very tactical standpoint, we'd like to see our device, the blossom with regulatory approvals so that it's starting to be used in clinics here in the US and globally. And in order for that to happen, the seeds of change had to have been planted. So that's what we started doing. We knew it was going to be a long road to change medicine, but we also know that it's for that very reason that this type of change hadn't already existed. So fundamentally, we identified this is a very clear problem statement. There's a very clear, critical, unmet need. Physicians are frustrated and making unnecessary compromises. Patients are uncomfortable, in pain, in distress and having terrible outcomes. And it's like no one's fault. Everyone is there to do their best and this is the outcome of what today's care looks like. So that's where we got started. And then to your point around how do you stay focused and what do you do? The market pulls us to having a product now and having revenue now and having customers now and having all the milestones. Rack them, stack them, knock them down, right. Check those boxes. Right? And it's very difficult. And then you add on the layer that we are two women, we are a diverse founding team. The data in who gets capital and who doesn't couldn't be more clear. Right? So we are constantly balancing how do we tell a clear story to the market about what our company needs to be successful, how much time that will take and what's possible for us to produce with that. And the reality that not everything happens overnight. So it takes persistence, it takes tenacity. You got to be in it, you got to stay in it, you got to keep going. And when you have those really crappy days, you have to be real that those are part of it too. And they're going to be days that totally knock you sideways, and you got to recover from those and at some point get back up and then get back in it so that you have the next two to three years to keep looking forward.

Daniel Stillman

I think you bring up a really valid point Onyi I'm curious what your perspective is on processing. I feel like in any relationship, dealing with healthy conflict is important, but we're talking about something else here, which is just processing of events and continuing to plan and exist together. And I'm curious what your perspective is on your communication, your collaboration style, how you manage some of these, because you come from very different worlds. You're very different people. How are you similar? How are you different in your perspective with how you deal with some of these things?

Dr. Onyinye Balogun

Yeah, so I think

Dr. Onyinye Balogun

we had a conversation. I think we were like, this is a marriage, and how does a healthy marriage work? Communication. So I think we had the conversations where you just need to be real with me, and I need to be real with you. If you're having doubts about something, don't let that simmer and fester. So I think we're very good about understanding that

Dr. Onyinye Balogun

the future of this company rests in partly in how well we're able to communicate. So we tell each other the good, the bad, and the ugly. So I think that's key and to have the time right. If you don't have a time where you can both set aside to deal with, one, what's going on with the company, and also, two, what's going on with us. Eve does a really good job of how are you doing? Are you feeling okay? And I hope I reflect that back to ask you about how you're doing. It can't just be, oh, what are the numbers? Oh, what's the strategy? It has to be what else is happening? Because we call ourselves mompreneurs sometimes. We're mothers, we're partners, and we exist. This company, building this company is part of that ecosystem. Sometimes someone gets sick and we have to shift a meeting. So I think we try to have the space, the scheduled space. And also if you need to just touch base about something that's on your mind, we have that opportunity. And I think we're both good listeners. That's one of the things that's really helpful in that I hear what you're saying. I reflect it back to you. You hear what I'm saying and you reflect it back to me. So that's been, I think, really helpful. I think we're very similar.

Eve McDavid

I actually feel that too. Okay. When I first met you, I was like, this woman is incredible. She's incredible at her job. She's incredible.

Eve McDavid

I think we felt like we were working together from very early on, and. That we sort of knit together that way. There was so much trust involved.

Dr. Onyinye Balogun

I'm trying to figure out how we are different.

Dr. Onyinye Balogun

Maybe we're different in that sometimes maybe I'm a little more like I want to just be efficient and be done and sometimes my thoughts are just but you do a really good job of mapping it out, so I'm finding it hard to verbalize. How are we different? What are the differences?

Eve McDavid

I think you made a really good point. You have a great ability of just cutting through crap and being like, yes, no, yes, no, yes, no. And I'll look at that same list and be like, well, what if and how about? That's really helpful to see the perspective and understand. Sometimes it just very much is a judgment call and you make that decision and you move on and you realize there are very few things that can't be unwound or addressed once you get to that decision point. So that has been, I think, really healthy in our ability to both be creative and dream of what a better world where better women's cancer care is experienced by the patients who receive it and delivered by the physicians who deploy it. And what does it take to actually get us there and how do we build that and execute against it?

Dr. Onyinye Balogun

And I want to double back on what you said about Reactivity, because we're a medical device company, right. One part of what we're doing, we started out focused on medical devices, and

Dr. Onyinye Balogun

people would tell us multiple times, oh, wow, you chose a really challenging part of entrepreneurship to get involved in. And we like a good challenge. But especially in this economic downturn, it's particularly tempting to want to pivot and say, okay, let me give you what you want. Let me morph myself into something that's more appetizing to investors. And so I think what we've done a good job of, we've done a good job of being true to who we are. We're never going to drop the medical device aspect of who we are. Talking with mentors, talking with some other individuals, we found that there were some digital tools that can enhance what we are doing with the that can enhance the education about why do we need this device?

Eve McDavid

Right.

Dr. Onyinye Balogun

That can enhance the education about cervical cancer in general. But at the heart of it all, we began with the medical device. And I'm really proud of us that we weren't just like, oh, well, people don't really like medical devices. So goodbye to the medical device. We forward with it. We now have the international patent. And I think that I think is key. I think we can't be reactive. You have to be true to who you are and follow that. The North Star.

Daniel Stillman

Yeah. It's a very different business model, a very different time frame. And I will reference I'll put a link for people who are listening and you may find it also interesting. I interviewed Avantika Dong from Plum Alley, which she and I talked on this podcast extensively about the gap in female and diverse founder funding, but also this idea of dressing your cap table and really being intentional about the kind of capital you're taking. People who really want to be part of the conversation, people who really get what you're trying to do, because somebody who thinks that you're a SaaS who's going to scale through enterprise sales, that's not your model, that's not the problem you're trying to solve. And it's a very different set of eyes that need to be looking at what you're doing to be able to get what it is that you're doing and to be part of the conversation. I'm curious, as you think about fundraising, which is obviously a huge part of the job, how do you engage investors in an intentional dialogue? Because I think it is clearly one of the most important conversations, and I think treating it like a conversation makes it much more productive, in my experience.

Eve McDavid

Absolutely. And we've had the success of finding folks who really understand what we're doing. They see the need. They are huge supporters of our work. And when you describe to them the state of care and what's possible, it's like an open and shut case, right? It's like, oh, this is so incredibly obvious. We see exactly what you're doing and we really love what you're doing. We want to be part of this. And there's a big conversation happening in medicine around patient centric innovations because so much of an outcome has to do with the trust and the partnership between the provider and the patient. And it isn't a one sided exchange. It's really symbiotic. And it's incredible that just the way that that partnership sort of is built and then grows can have an incredible impact on the patient's outcome. And it's incredible. And so when you're having conversations about outcomes in human lives and you have an investor who understands that that type of impact is where they want to be placing their capital, we do incredibly well in those rooms. And that, I think Onyi talked earlier about this win that we had last year. That was the first time that we did so much of this work over Zoom. It was the first time that we'd been in an open air environment where we're talking about the work, and as each of us are speaking, we're watching the room and we're seeing people lean in and then our eyes open. And when you see that, you know, you're like, okay, I'm in the right room with the right folks who are going to want to help us do something here. And we feel those environments, we know what those environments look like, and we win really well in those environments. In other areas where you'd love to be in a conversation with someone who has an enormous fund and they write enormous checks, and you want to be the recipient of one of those enormous checks. You also figure out, really quickly that no, this is not something that in a quarter's time you're going to have the type of metrics that their fund needs to show in order for their investors to be satisfied and fulfilled. And unfortunately, there's a lot more investors that fit into that latter camp than folks who are investing their capital to do great work in the world that also has a great return. And so part of our fundraising journey has been to identify those people and those rooms where there is that focus on the human impact of that capital. And so this fall, we'll be exploring a crowdfunding campaign to make our work more accessible from an investment standpoint so that we're able to get the message out to folks who are interested in supporting our work and interested in seeing this type of impact really be possible in the field that we're working in.

Daniel Stillman

That's really exciting. And I love this idea of knowing your room and being like, yeah, it's just not my room. Because we can be very hard on ourselves. Just speaking. I can be hard on myself. Use I statements we all can be and be like, but not everybody's for you. I'm not for everybody.

Eve McDavid

That's right.

Daniel Stillman

But it can be very hard to be like, oh, this guy doesn't get me. Right. And that's on me. But no, it is what it is. Sorry Eve, you're going to add some.

Eve McDavid

Flavor to no, that's exactly right. We would have meetings where we were just not clicking and we'd hang up on the close the laptop and then we'd call each other and be like, okay, I'm not discouraged. Are you discouraged?

Eve McDavid

That a lot. And we've had to find those rooms. Right. Like no one is laying out a roadmap to how to find those rooms and how to find those people. We've had to find them and we've had to do a lot of sifting some insufficiently to get there.

Daniel Stillman

Yeah.

Dr. Onyinye Balogun

I think one of the good things is you can tell when the person is for you. We've been fortunate and when the person gets it, they get it. And frequently when they just are opposed and they're not in support, a lot of them have been just very loud and clear about not seeing why this needs to really happen or how it's going to happen. So I thank them for the no's.

Daniel Stillman

No is always better than a roll.

Dr. Onyinye Balogun

Yes.

Daniel Stillman

It's just being confident and clear that aware of the signal of push versus pull. I think of it, it's like am I pushing this or are they like pulling it out of me? They're excited. You can feel that energy. You're aware of that. We're sadly getting close to the end of our time. What haven't I asked you that? I should have asked you all what haven't we talked about that you feel like is important for us to touch on? We talked about the crowdfunding, we talked about Gynecological Awareness Month, your amazing story, the product. What haven't we touched on that's important to maybe touch on?

Dr. Onyinye Balogun

Trying to think.

Eve McDavid

I can chime in. Yeah, okay. I got nothing.

Daniel Stillman

That's good. I call that a plus.

Eve McDavid

Yeah, that's good. We covered a lot of ground. I want to just do a super quick plug for what prevention looks like in cervical cancer, because that's a big.

Daniel Stillman

Question that plug away.

Eve McDavid

Talk to a room about what does it actually mean to prevent cervical cancer. So if you are a parent to a child, the most effective time, the most effective tool that we have today to prevent cervical and actually a number of other cancers that are also caused by the human papillomavirus that affect both men and women. The most effective time to have that vaccine that almost entirely prevents these cancers is between the ages of nine and twelve. So if there are parents in your audience listening and they're wondering whether they should have their child vaccinated, the most effective window is before any exposure to sexual activity. So between the ages of nine and twelve, if you are someone who is listening, who is outside of that window, or your children are outside of that window, that's okay, that's actually really common. The vaccination rates in this country are not nearly as high as where they could and should be for actual elimination of this disease. But if you're outside that window, you or your child, then what you need to be doing is having routine path and HPV tests with your gynecologist or your primary care provider. And those tests happen anywhere from every year to every five years, depending on your risk factors. And so having a conversation with your provider about when you need to be screened, what those results mean, and what any follow up care is required is the key to preventing this disease. If you are up to date on vaccination, if that's an option, and if you are up to date on screening, then you can almost entirely prevent this disease.

Dr. Onyinye Balogun

Absolutely. And I'll chime in that nine to twelve is ideal. But even if you're outside of that window, you should discuss with your medical provider because there may still be efficacy, it may still have value for you to the vaccine. And again, if you see anything concerning, go to your physician. Some of the key signs for cervical cancer are you may notice bleeding in between your periods. If you're still having periods, you may notice bleeding after intercourse or have pain with intercourse. Sometimes there's a strange discharge. It may not be bleeding, but sometimes people don't have symptoms and it's caught, like Eve said, when you go for screening. So I cannot overemphasize the importance of screening. So there you have it, prevention and screening hand in hand.

Daniel Stillman

Well, I think that's a good place for us to write on time, and I want to respect your time. I really appreciate you making the time for this conversation and sharing everything that you're working on. It's really important stuff. I wish you two the absolute best. And where should people go on the Internet to learn more about all things mission driven tech?

Eve McDavid

Yes. Perfect. So check out our website@missiondriventech.com, and then you can also find me and Onyi on LinkedIn, where we share live updates as we build in public.

Daniel Stillman

We'll put links to both of those in the show notes. Excellent. Well, we'll call thank you so much. Thank you. We'll call scene. And I really appreciate you being so generous and thoughtful with your responses. Thank you so much.

Eve McDavid

Thank you, Daniel. Thank you so much.

Give First: The Long Conversation of Being a Co-Founder

David Hoffman built and sold big-data and data analytics company Next Big Sound to Pandora in 2015. He's now building Beam, which helps people create shoppable mood boards for DTC brands.

David reflects on his experience with mentorship and the long arc of the conversation that is being a co-founder and being in community. We unpack the Techstars motto "give first" and discuss the power of the Techstars community and the importance of community relationships in entrepreneurship.

We talk through the complex evolution that is founding and scaling a startup and his experience doing just that with Next Big Sound, and the challenges of becoming a leader inside a growing company.

One challenge is always scaling culture as a company scales, and David outlines some of the routines and structures that helped in defining his startup's culture. David also shares some insights on the post-startup-sale emotional roller coaster and the decision to build another company. Some of my other favorite insights from David:

  • Living the “Give First” motto requires approaching everything with curiosity.

  • “Grown ups” is a construct: When it is your idea and your company, you can make the decisions you need to make.

  • Your Culture is made of your routines, whether it’s Friday bagels or snap-clapping after people share wins.

  • Your MVP product can be much, much more simple than you think if it creates value for your customers.

David’s nuanced reflections are a gift, and I’m so glad he sat down for this conversation.

AI Summary

David reflects on his experience with mentorship and the power of the techstars community. Daniel and David discuss the principle of "give first" in Techstars and the importance of community relationships in entrepreneurship.He discusses the evolution of his company, Next Big Sound, and the challenges of becoming a leader. He emphasizes the importance of routines in defining a startup's culture and reflects on the emotional roller coaster of the past eight years.

Conversation timeline summary:

(0:51) - David  talks about the value of mentorship and giving back in the techstars program

(2:30) - David  discusses how he tries to save people time and be thoughtful in his conversations with others

(5:25) - David  reflects on the power of the techstars community and relationships that have evolved over time

(18:54) - After realizing their initial idea wasn't working, they shifted their focus to answering the question of how a band becomes famous and started tracking song plays on MySpace to gather data

(24:47) - They launched on Demo Day despite advice not to and landed major record label deals, collaborated with them to build a pro version of their product, and generated SaaS subscription revenue

(27:58) - The transition to becoming leaders of an organization was challenging, especially while trying to build bleeding-edge software and manage people with unknown skill sets. They learned the hard way about relinquishing moral authority too early and the importance of having confidence in themselves rather than seeking a "grown up in the room."

(31:05) - David  emphasizes the importance of routines in defining a startup's culture, citing examples from his time at Next Big Sound

(43:00) - David  reflects on the emotional roller coaster of the past eight years and the importance of taking time to decompress and figure out what's next

Links, Quotes, Notes, and Resources

Beam

Minute 1

David Hoffman:

one of the things they taught us was the value of mentorship and learning from people who'd done what you were trying to do, and both what worked and what didn't work, and just being really intellectually honest and open to feedback, and criticism, and ideas. And, as part of that mentorship, it was instilled in us as we went through the program, successfully raised money, built a business, later sold the business, that giving back and giving first is the way to approach things and to approach life. So for me, in conversations with potential partners, or employees, or customers, or other entrepreneurs, I'm always looking for what I can provide in value before expecting anything in return.

Minute 31

David Hoffman:

We were like, we need a senior person who can teach us and who can be the "grown up" in the room, with big air quotes. Now, more than a decade later, I am realizing that the, big air quotes, "grown up" in the room thing is very much a, I don't know, made-up construct. Yes, there's wisdom that can be learned, but I think I learned the hard way that when you start something and you have insights and you have conviction around it, there's moral authority that's attached to that, especially as it relates to decision-making, and when you start to relinquish that moral authority or decision-making... and still in the early days of a startup, which I consider Series A... it puts you at major risk for wasting time and wasting money.

David Hoffman:

So, with the new business, when we started it, I brought on some more senior people and had a similar experience again of, I have the unique insight here, I have the conviction, I have the ability to execute on it. Why am I relinquishing moral authority and decision making on something? Is it imposter syndrome, lack of confidence, fear? And I think the healthy thing and that I've gone through is facing all those things head on and being confident in making those decisions myself.

Minute 33

Daniel Stillman:

What was that shift for you, realizing that you could find that part of you to rely on?

David Hoffman:

I think it was just reflection and being honest with myself about what was working and what wasn't and where I was spending time, and that's... Going back to the Next Big Sound story, the piece that was really interesting as we matured and got some confidence there, A: we found some really great senior people who we loved having in the room and who made everyone better. They didn't need to be the, big air quotes, "adult in the room". It was more just seeing them as peers and collaborating.

And the other was just getting into and being really thoughtful about the routines by which we ran the business. And this has been a pattern for me in life, both personal and work, is when things get stressful I lean on routines and try and create good routines. And with startups, it's amazing. When people talk about culture, I literally think, "What are your routines?" That's all I want to know about, because that's in my mind: what defines a culture?

Minute 37

David Hoffman:

We did regular Demo Days at Next Big Sound, and it was mostly engineers presenting, and designers and teams presenting what they'd been working on ahead of it being released, and sometimes going into the backstory or how it worked, mostly showing in.

And so, creating that both opportunity and expectation that every Friday new work is going to be shown, the person who did it's going to be sharing it with everyone. It's not a feedback session, it's a "Here's what's going on" session, being explicit about the intention of it, kept it personal and kept it so it was across the team and not just a small group.

Daniel Stillman:

Hmm. That sends really interesting message, that it's the person who made it is sharing it. It's not feedback. Was it explicitly celebration or is it a "Here it is"?

David Hoffman:

We had a big clapping culture, so after anyone would present anything, people would snapper clap, and I think that sort of just celebrating small wins and being excited for each other's progress was sort of key to the culture we built.

MOre About David

David Hoffman built and sold big-data and data analytics company Next Big Sound to Pandora. He's now building Beam, shoppable mood boards for DTC brands.

Full Transcript

Daniel Stillman:

Right. So, you actually... We're going to jump around. You said there's this principle in Techstars of "Give first". How is that delivered to you, and how do you feel like you're living that principle?

David Hoffman:

Wow. Big question to kick it off. I love it.

Daniel Stillman:

Yeah, were in.

David Hoffman:

Yeah, so it's been a long time. We went through my first business, went through the third class of Techstars in Boulder, Colorado in 2009. David Cohen, who started Techstars, was actually running the program at that time. They had just launched Boston. It was their first city besides Boulder, they're still in the early days of figuring out the program. So, I'm sure it's come a really long way in the many years since then, but even then one of the things they taught us was the value of mentorship and learning from people who'd done what you were trying to do, and both what worked and what didn't work, and just being really intellectually honest and open to feedback, and criticism, and ideas. And, as part of that mentorship, it was instilled in us as we went through the program, successfully raised money, built a business, later sold the business, that giving back and giving first is the way to approach things and to approach life. So for me, in conversations with potential partners, or employees, or customers, or other entrepreneurs, I'm always looking for what I can provide in value before expecting anything in return.

Daniel Stillman:

That's a really... I mean, that's a beautiful and important shift. How-

David Hoffman:

Yeah. It's funny how these small phrases root themselves in your brain and then you try and live them. I guess that's what values are.

Daniel Stillman:

Yeah. Give... And it's a stance, right?

Yeah. How does that show up for you? Because you said you've been talking to some first-time founders more and you feel like you're ready, you have more to give back now.

David Hoffman:

Yeah, yeah, totally. I think it's in trying to save people time, and I think it's also in being really thoughtful that your... Or I'll just speak about myself, my experiences... But one data point and what happened for me doesn't necessarily mean it'll happen for someone else, but hopefully the story and learnings are inspiring. And likewise, on the other side, when someone takes advice or tries something that's recommended and reports back how it works, I can't think of anything more gratifying. The learning that everyone gets is awesome.

Daniel Stillman:

I always like to tell people that the price of free advice is telling me how it went.

David Hoffman:

Yeah, it's, yeah.

Daniel Stillman:

Very few people pay that price, but I always tell them, "Please, I'd love to know if it was bad advice."

David Hoffman:

Yeah. I love the etiquette around double opt-in intros and moving people to BCC . It seems like that's well-rooted in the world. The thing that I try and do is boomerang that message for after I've had the meeting so I can follow up with the person who introduced me and say, "Hey, here's what I learned. Here's how it went," and close the loop.

Daniel Stillman:

And thank them for the introduction.

David Hoffman:

So few people do that.

Daniel Stillman:

Oh boy.

David Hoffman:

Yeah, exactly.

Daniel Stillman:

So, boomeranging is a really great principle here, because we're going to be going back and forth on the timeline a fair bit, because I think in a way, at the beginning of your Techstars journey, if he were in this room talking to you, I imagine he wouldn't necessarily... Well, I'll ask you, how do you think he'd sound? I won't put words in your mouth. Like, if both you now and you then were in the room together, what would he think looking at you, do you think, given everything that you've accomplished so far?

David Hoffman:

I don't know. I mean, I think Techstars has done a tremendous job of creating very valuable businesses at scale. And my first business, Next Big Sound, was one of the sort of early outcomes of that program, but it's certainly been surpassed many times over by lots of other companies and entrepreneurs now. So when I think about that, I think I am but a drop in a bucket of a huge number of entrepreneurs that have benefited from this and can learn this. And I think the scale is what, rather than me individually, is what's most exciting about it.

Daniel Stillman:

Yeah, well, I'm thinking more specifically in terms of what you were hoping to accomplish at the beginning of your entrepreneurship journey.

David Hoffman:

Yeah, yeah.

Daniel Stillman:

And now you exited well and you're starting your second company. Is that what you, what he was imagining then? Do you think he saw that?

David Hoffman:

I think so. Yeah, I think that was the hope, is people finding a path and building businesses that create value for society, and stakeholders and shareholders, and having a great enough time doing it that they want to do it again. And that's, it's funny now. I know we're definitely jumping all over in time and we can tell more backstory whenever you want to, but I just was seeking some advice and help on the new business, and one of the people that I went to was one of the LPs in the bullet time fund that invested from Techstars that invested in Next Big Sound. And so it's these people that I met now 13, 14 years ago, 2009 at Boulder, that I still have relationships with and that still are able to provide massive help and are excited about what we're doing, and vice versa. So, I think that the thing I underestimated, and maybe everyone did, is the power of that community at scale and how those relationships evolve over time.

Daniel Stillman:

Yeah. Wow, and that's a long arc. It is very hard to... And this is one of the things that's really interesting and challenging. One founder who I'm coaching, I think one of the challenges we all have is it is hard to imagine what a 13-year arc is. It's hard to know what an opportunity or a conversation or a person in front of you is going to become, which is maybe why the give first principle is so powerful, because we literally can't know, and yet we also have to balance how much we give and what we focus on.

David Hoffman:

Yeah, yeah. As calendars get busy and people are asking for time, saying yes can be hard, but you're exactly right. You never know who you're actually going to help and what impact you could have on them, and then the cherry on top of who they're going to turn into or what it could become, that's been really gratifying too now, over the last 13 or 14 years, is seeing our peers that we went through Techstars with then, seeing our friends that we were graduating from undergrad with, seeing other entrepreneurs we met around that time, and what they've gone on to do, a lot of them are now in the second or third act of their career, and it's so inspiring.

Daniel Stillman:

So, Samir isn't here to speak for himself, so we can't get his side of the meet-cute. This is the way I think of this, in the rom-com-

David Hoffman:

Yeah, yeah, you always have meet-cute.

Daniel Stillman:

I don't know if you're a rom-com fan. Yeah, there's meet-cutes like, oh, you knock over their coffee. You're like, "Oh, I'm sorry."

David Hoffman:

Yeah.

Daniel Stillman:

Do you remember the first time you met Samir, and what happened? How you two started this conversation that is now a 14-year conversation that you've been in?

David Hoffman:

Yeah, it has been a long conversation. Yeah, so we were both in undergrad at Northwestern, and Next Big Sound was started by myself, Samir, and Alex White, also, at undergrad. Alex was a year older than us, and there was an entrepreneurship class taught by this professor who was adjunct, who we knew had sold his last company and was working on something new, and also teaching, and it was a very well-regarded class. The professor name was Troy Henikoff. He went on to run Techstars Chicago, early angel investor in our first business, and then it's been running Math Venture Partners since then. So, it's a small world, and crazy, again, how that conversation with him has evolved over the 14 years.

Anyway, back to the co-founder story. We got to the first day of class, and Alex and I knew each other because we were in the same major, and we'd met a few times and talked at class and decided we wanted to work together. Samir, I think, showed up late or at the last possible minute and was brought there by another mutual friend of ours, Neil Sales Griffin, who also would actually go on to run Techstar Chicago, and run for mayor of Chicago at one point.

He had run into Samir at Norris and said, "Hey, I'm taking this entrepreneurship class. You should come check it out." And, just kind of by random encounter, Samir ended up in this class. And we knew of each other prior to that: there'd been a big student government election, and Samir and I were, as we found out later, two of the only people on campus that knew how to build websites, and we built competing websites for each candidate.

So, I built one for Neil and he'd built one for the other guy running, Mark, and we were like, "Hey, we both build websites. This is interesting." And Alex was very smart to go, "Hey, these two guys build websites, and this is interesting. We should all work together." So that was the first time we really started working together, was in that class in undergrad, and it's gone on since then.

Daniel Stillman:

Well, it feels like you're skipping some steps, but-

David Hoffman:

Yeah. And rest is history.

Daniel Stillman:

Yeah, the rest is... And a miracle occurs. So you're all in this class and you clearly all value entrepreneurship, because you're there, or Samir found himself there through serendipity or good social pressure. How did the conversation around "Let's make this thing"... Or were you thinking, "We want to make anything," and you found the thing?

David Hoffman:

Yeah. So I found, I fancied myself a designer at the time, so first print design... I'd been doing newspaper and magazine, and then web, like doing themes for blogs, and then software down the line. Samir was a designer too, but he was also a comp-sci major, so he'd been studying computer science; and Alex said a lot of great ideas and was very charismatic. He'd actually pitched me on this idea prior to the class around fantasy sports for music, and I had given him some feedback, and that's kind of where the conversation ended. When we got to the class, that was one of the early things, was figuring out what problem we wanted to solve and what the solution was. We went wide and brainstormed a lot of different ideas, but ultimately Alex, being as charismatic as he is, was very convincing that we should build The Next Big Sound and a fantasy sports for music site, and so we all got on board with that and started building.

Daniel Stillman:

That's crazy.

David Hoffman:

Yeah, so... And it was a funny... You hear about these companies that get started in classes. I don't think any of us thought anything would come of it. The sort of first indication we had were mentors and other successful entrepreneurs that Troy would bring to class. We would practice pitch them, all the different teams in the class, and they'd ask questions and give feedback. And we were getting really consistently engaging questions and feedback to the point where, as we near to the end of the class, Troy, the professor, and some of the mentors that he brought through would take us aside and say, "Hey, if you guys are serious about this you should really consider devoting some proper time and money to it and exploring it."

And there was a entrepreneurship pitch competition on campus, and we enrolled in it, and it was against all these Kellogg grad school kids, and medical device kids and people doing different things, and we ended up winning the competition and getting an oversized check, and we were like, "All right, that's more incremental positive validation." And then we found out there's this accelerator... This is pre Techstars... that was operating in Chicago, down in Champaign, Illinois, and we managed to just squeeze our way into their first or second class that they were running. And so, we spent the summer... Packed up the car, moved down to Champaign, and spent a summer just working on this idea, and that's when we built Next Big Sound 1.0.

And it was the first time any of us had ever really built software, built a business, worked together on something like this. And the way Samir talks about it, and what we'd probably say if he was here, is that that was when we learned how to work together. That was so much of the conversation that was like: who does what, how do we do this? How do we be in alignment and not conflict? What does that look like?

Daniel Stillman:

Yeah. How did you learn to navigate conflict? Because I imagine there was some.

David Hoffman:

I was going to joke and answer, "We learned to navigate it poorly," but that's not doing anyone justice. I think we got really lucky. Alex and Samir were both and are both really thoughtful, patient, kind, smart people, and I think we all approached things with curiosity. One of the things Alex would say to me many years later, that I think about all the time, is in meeting a bunch of people through building a business, he'd ask them about what they valued and how they thought about the world, and the word that always came up was "truth" and just trying to find the truth. And I think over time our collaboration got towards that too, of this isn't about our singular egos or anything else. We just need to find what's true in this world that we're operating in and build based on that.

Daniel Stillman:

That is so interesting. So, what that is sparking for me, somebody had just posted this on Instagram. So, I follow Neil Strauss who... I mean, this is a total side. I'll just read you the quote from Rick Ruben, because I don't know if you-

David Hoffman:

Oh, sure.

Daniel Stillman:

He just came out with this big book, he's been hitting hard everywhere, and there's this thing about making decisions around the moment one collaborator gives into another. By settling on a less preferential option for the sake of moving forward, everyone loses. Great decisions aren't made from a place of sacrifice; they're made by the mutual recognition of the best solution available.

David Hoffman:

Yeah. That resonates.

Daniel Stillman:

Yeah. To me, it's not about my truth or your truth.

David Hoffman:

Yeah.

Daniel Stillman:

It's about the truth.

David Hoffman:

Exactly, the Truth. Yeah. Like, capital T. Totally. It's funny, I think that's one of the things Samir and I initially bonded over, was that we both just had a love for making things, and designing things, and building things, and it happened to be software. And I remember being 20 or 21, brightest... Next Big Sound was getting started, and being frustrated, right? Because you're handling all these things that you are ill-equipped to handle, and really just leaning on this thought that I'd have every day of, "I just want to build things that people love," and just being motivated to make stuff and get it out in the world, and having that be sort of a guiding thing was very helpful. And Samir was very much of the same mindset.

Daniel Stillman:

Mm-hmm. So, the question that I'm tempted to ask is: what do you feel like you were most ill-equipped to handle together as co-founders?

David Hoffman:

Yeah. The list is too long to go into detail, but I can tell a little bit more of where the story unfolded from there, and I think it'll shed some light on it. So, we built a web app. It was a streaming app inspired by Pandora. This was when Flash was still the default technology for streaming music online-

Daniel Stillman:

Good times

David Hoffman:

... to date myself a little bit... And we signed up all these bands. Alex had a ton of connections in the music industry. We had them upload four song demos and then we sent out the site so people could listen to the music, to as many people as we could find, and they could sign with big air quotes the bands they thought were going to become famous. And we were trying to answer this question... this was sort of the genesis of the whole idea from Alex... was how does a band become famous? What happens from that small band playing in a garage to headlining a nationwide tour? What are the steps in between? What's repeatable, what's luck? How does this actually work?

And we got this... I mean, thinking back, this is amazing. We're 20, 21 years old. We've put together this site, we get a writeup in the New York Times, just dream press piece, and it sends some traffic, but what we're seeing in the numbers are just crickets. So no one is using this thing that we've built.

Daniel Stillman:

They're coming to look, but they're not playing with it.

David Hoffman:

Yeah, yeah. Exactly. And growing bands is hard, growing listeners is hard. We're talking to one of those mentors and he's like, "How are you going to make money?" We're like, "We're going to sell T-shirts." And he's like, "So, is this a T-shirt company?" We're like, "No, we don't want to build a T-shirt company."

Daniel Stillman:

Was that seriously a monetization strategy at one point?

David Hoffman:

That was earliest ideas, yeah, and Threadless was really big in Chicago. Then we had met the founders and were really inspired by them. But regardless, we realized this thing wasn't working. We went back to class, it was Samir and I's senior year Alex had graduated. He and Samir and I discussed it, and we wanted to keep pushing and figure out a way to make it work. So he pushed back his job offer and was sleeping on couches and just trying everything he could to get it off the ground. I mean, talk about grit. He really just pushed it through. And, we'd heard about this thing called Techstars and Hail Mary-applied with this idea. We weren't spending too much time on it anymore. We thought it'd be really cool to go to Techstars, though. Ended up getting in, flew out for Techstars for a day and met a bunch of people there.

We were so excited, must have made a good impression, and we drove from Chicago to Boulder overnight. Straight shot in my car... Alex, Samir and I all packed in... and when we got there on the first day, it was this full-day orientation.

David Cohen talks for the whole day, it's the only day he does that. And at the end of it, you can tell he is fried, but we really wanted to talk to him. We went up and said, "Hey, we've got something we need to share." And he goes, "What is it?" "You know that idea that you just accepted into Techstars, fantasy sports for music? It's not working and we don't want to build it." And he said, "That's fine. We invest in people, not ideas. But you need to figure out what you're going to do." And it was the best possible reaction. I mean, so much affirmation that we were there because it was us, not for a specific idea, and acknowledging that we could figure out something that we could actually build.

And so, we went back to the drawing board and we kept coming back to that first question of "How does a band become famous?" And what we realized is that we didn't need to build another destination site where bands and fans were connecting and track everything based on that. Fans were already consuming music online in massive quantities, and the most popular streaming site at the time, to date myself again, was MySpace. So we started tracking how many song plays artists were getting on MySpace, and rest is history, to use that expression as many times as possible while we chat today.

Daniel Stillman:

That's a really interesting shift, from, "We make a place" to, "We're going to go where the people are and where the information is."

David Hoffman:

I think it's, the reason I tell that story is, well, because it's the next thing that happened in that sort of journey, but also because that thing about the truth of and being married to a problem and not a solution. It's like, we want to answer this question. There's so many different ways we can do that, as opposed to, "We came up with this idea; this idea now has to be in the world."

Daniel Stillman:

And where did the seed, do you think, for monetization come from? Because clearly you were jamming on this question of this, how does a band become famous, and that was something you were passionate about, and you really found a shift in going to learn about that, and to get a better answer to the emergence of that happening. But T-shirts to getting acquired by Pandora is a big jump.

David Hoffman:

Yeah, absolutely. During Techstars, once we realized that this was something that was possible... So, as soon as we saw this on MySpace we called a bunch of people in the music industry and asked them, "Hey, are you paying attention to what's happening online and how often your artists are being played?" This is mostly managers and some labels. They're like, "Yeah, we know it's happening, but we don't know how to track it." Some of the more sophisticated ones had hired armies of interns to write down numbers by hand, in spreadsheets,

Daniel Stillman:

Spreadsheets. This is, I feel like every startup is finding a way to eliminate a spreadsheet. Is this a-

David Hoffman:

Every good SaaS startup is. Yeah, for sure. We had them send us the spreadsheets and we were like, Great. We can automate this for you, track way more artists, send it on a regular basis." And they said, "That sounds amazing." And so, we set off to build it and-

David Hoffman:

Well, we weren't that smart. So, being a designer... And this is a lesson I've had to learn over and over again, of the risk of over-designing things. I said, we can just send them a beautiful PDF of their stats and we can show time series graphs and it'll feel like an official report, and we'll send it to their inbox. So, we manually put these together before our crawling abilities were across the board, and put them together for 10 different artists, and sent them out to all their managers on a Tuesday. And we were waiting to hear back, and it was nothing. No one responded, and we were like, "This is bizarre. We've just talked to all these people. They've said they want this, we did it. We sent it to them. What is going on?" And we kind of got that feeling we had with the first version, where we built it and they didn't come.

We're like, "What did we miss?" So we were more persistent this time now, when we emailed all of them and said, "Hey, did you see the report? What's going on?" And I think more than half of them wrote back and said, "I'm on my Blackberry..." To date myself again. "It doesn't open PDFs. Can you please send it another way?" So the next week we switched to plain text emails, just writing in the body of the email a table of the stats that they cared about for their artists, and nine out of 10 of them wrote back and said, "Hey, can you please add this person? Can you track this artist? Can I share it with this person?" And the reaction was exactly what we were looking for and we were off to the races.

But, to answer your question about how do you go from those early days to the monetization piece, we put up a site in private beta and started inviting people in the music industry to it, and got the advice from everyone we spoke to not to launch on Demo Day. So, Techstars has this thing called Demo Day where all the companies present at the end, there's a bunch of investors in the audience, and get some press coverage, and you're kind of introducing the business to the world. We ignored the advice and launched on Demo Day. Luckily, it ended up working and we didn't get crushed too badly, and it got a lot of attention from the major record labels, and we found out that they were spending a lot of money trying to solve this problem already.

And, we are also very lucky to get introduced to someone who had been at the major record labels for a long time, had a deep Rolodex, and knew people there. And the timing... And this is another one of those... Like, I mentioned the word persistence earlier, that I think about constantly. Timing is the other thing I think about a lot based on these experiences. The timing was amazing. Sony had built this team that was trying to measure what was happening, and they were running a pilot for a software provider, and they didn't know who they were going to use yet, and we ended up being just in the right place at the right time to participate in this pilot, have direct connections to a bunch of people there, and I remember going into their offices... We'd fly from Colorado to New York every six weeks... and showing them a blank screen and some of the stats we had and asking, "What do you want to see here? What would make this a part of your daily workflow and incredibly valuable to you?"

So we collaborated with them super closely to build out a pro version of our free product, where you could just get stats on the artist to answer some of their more sophisticated questions, and that led to our first major label deal and SaaS subscription revenue.

Daniel Stillman:

Wow. And that's when things really took off, in that sense?

David Hoffman:

Yeah. So that, we had landed, I think, two of the three major record labels by... Started the company, went through Techstars in 2009. We were working with two of the three major record labels by 2010, 2011 and had a bunch of the smaller sub-labels signed up separately. And so, had licensed charts to Billboard. Alex is an incredible people person and great at getting to know people, and he also really believes in serendipity and just exposing yourself to chance and opportunity, and one of those things that happened were Billboard Magazine licensing charts for Next Big Sound. That gave us this big stamp of credibility.

Daniel Stillman:

Wow.

David Hoffman:

And with that progress we raised a series A in 2012 and moved the company to New York City to be closer to our customers. I think that's around the time we met, actually.

Daniel Stillman:

That's around the time we met, yeah.

At that time, when you moved to New York City and you had your series A, this is a really interesting inflection point in any company.

David Hoffman:

Yeah.

Daniel Stillman:

Right, because I presume you started to hire, and you had to become leaders of an organization.

David Hoffman:

Yeah, yeah.

Daniel Stillman:

What was that transition like for the three of you at that moment?

David Hoffman:

It was challenging, and I think it... some of the things that I learned then are mistakes I've repeated the second time around and really learned deeply from. Yeah, we were hiring pretty aggressively, and we were most focused on data science at the time, which, super nascent practice in 2012. And we were looking at all these predictive models around weather and other industries and asking, "How do we actually use this massive data set that we've amassed to predict who's going to become famous before they're famous, and make accurate predictions?"

And so, not only were we leaders for the first time in a growing group of people, and needing to figure out org charts, and routines and cadences, and one-on-ones, and all the stuff you're supposed to do, but we were also trying to build software just at the bleeding edge of what was possible at the time and manage people who we had no idea the depth of their skillsets and what they were able to do.

So, I think it was a lot of trial and error, honestly, and a lot of trying to bring in senior people who could help. And that's sort of the lesson that I've learned, more than once, is... Especially then. I think when we moved to New York... I was 25 and we were all so young we felt like kids. We were like, we need a senior person who can teach us and who can be the "grown up" in the room, with big air quotes. Now, more than a decade later, I am realizing that the, big air quotes, "grown up" in the room thing is very much a, I don't know, made-up construct. Yes, there's wisdom that can be learned, but I think I learned the hard way that when you start something and you have insights and you have conviction around it, there's moral authority that's attached to that, especially as it relates to decision-making, and when you start to relinquish that moral authority or decision-making... and still in the early days of a startup, which I consider Series A... it puts you at major risk for wasting time and wasting money.

So I know I'm not speaking in a lot of specifics here, but there's definitely a lot of learning around that time of how do we grow up in this business, and how do we just have the confidence to know that we can learn and do this ourselves, and we don't need to necessarily find someone to be the grown up in the room.

Daniel Stillman:

Yeah. So, it sounds like... You said that you're doing that again, or you're trying not to do that again?

David Hoffman:

Trying not to do that again, yeah. So, with the new business, when we started it, I brought on some more senior people and had a similar experience again of, I have the unique insight here, I have the conviction, I have the ability to execute on it. Why am I relinquishing moral authority and decision making on something? Is it imposter syndrome, lack of confidence, fear? And I think the healthy thing and that I've gone through is facing all those things head on and being confident in making those decisions myself.

Daniel Stillman:

Yeah. What was that shift for you, realizing that you could find that part of you to rely on?

David Hoffman:

I think it was just reflection and being honest with myself about what was working and what wasn't and where I was spending time, and that's... Going back to the Next Big Sound story, the piece that was really interesting as we matured and got some confidence there, A: we found some really great senior people who we loved having in the room and who made everyone better. They didn't need to be the, big air quotes, "adult in the room". It was more just seeing them as peers and collaborating.

And the other was just getting into and being really thoughtful about the routines by which we ran the business. And this has been a pattern for me in life, both personal and work, is when things get stressful I lean on routines and try and create good routines. And with startups, it's amazing. When people talk about culture, I literally think, "What are your routines?" That's all I want to know about, because that's in my mind: what defines a culture?

Daniel Stillman:

So when you think back on the routines that saved your life-

David Hoffman:

Yeah.

Daniel Stillman:

... what do you feel like is the baseline in... Especially in, when we're talking about multiple co-founders and complex decision making in a fast-paced context?

David Hoffman:

So we had a superpower at Next Big Sound, which was all living in the same house together. So-

Daniel Stillman:

The three of you?

David Hoffman:

Yeah, the three of us, and then up until we were, I think, nine people, everyone who joined the team moved into a house.

Daniel Stillman:

Wow.

David Hoffman:

And, yeah, we were all 22, 23 people were moving in from out of state.

Daniel Stillman:

What neighborhood were you living in?

David Hoffman:

Well, this was in Boulder before we moved to New York.

Daniel Stillman:

Oh, gotcha. Gotcha. Yes.

David Hoffman:

We were up on the hill in Boulder, by the university.

Daniel Stillman:

I was going to say. It's like, where do you find a place for nine people and-

David Hoffman:

Yeah, in. New York City. I know.

Daniel Stillman:

New York City, where you're living in Jersey City.

David Hoffman:

But we're deep in Brooklyn.

Daniel Stillman:

Yeah.

David Hoffman:

Yeah. But the routine that we developed there was just having dinner together every night. So even if someone had been on client calls all day, or deep working on a project, or whatever it was, we'd all decompress after at dinner and share what happened during our days and kind of stay in sync. And, as the team grew, I noticed the customer support person and the backend engineer never talked to each other. They didn't have a natural reason to at work. So we started bringing bagels in on Friday, just with the idea that we'd all have breakfast together every Friday so that we're doing something as a team on a regular basis, and that evolved into what was called Friday Bagels or Fragels: an all hands meeting once a week where we'd just go over the business and talk about what was going on. And so those sort of routines, of founders having regular dinners and team coming together regularly around a meal, you know, I think are some of the only things that kept us all pointed in the same direction.

Daniel Stillman:

Yeah. How big were you all when you got acquired?

David Hoffman:

I think we were just shy of 30 people, so not huge.

Daniel Stillman:

So it was still possible to have a reasonable all-hands at that point?

David Hoffman:

Yeah.

Daniel Stillman:

Yeah.

David Hoffman:

We'd all cram into a conference room at, benches around the table, and make it happen.

Daniel Stillman:

Did it shift... I mean, this is something that I'm obviously obsessed and nerdy about. There are major differences between a conversation of nine people and 30 people. It goes like, it's a graph theory, right? It's not the log, but it goes up fast. There's a lot of conversational density, and how did you make it as useful and rewarding at 30 as it was at nine?

David Hoffman:

Yeah, and I think it definitely changes. This was pre-remote days, but we were hybrid at that point, so there's also people calling in on Zoom every time, creates these tensions, and at 30 that communication became more challenging. I think we always approached it as a chance for anyone to share and not a "leadership is telling everyone else what's going on" type of meeting. And the way we did that was actually... Trying to think if we switched it at some point, but we had, from Techstars, the idea of Demo Day. We did regular Demo Days at Next Big Sound, and it was mostly engineers presenting, and designers and teams presenting what they'd been working on ahead of it being released, and sometimes going into the backstory or how it worked, mostly showing in.

And so, creating that both opportunity and expectation that every Friday new work is going to be shown, the person who did it's going to be sharing it with everyone. It's not a feedback session, it's a "Here's what's going on" session, being explicit about the intention of it, kept it personal and kept it so it was across the team and not just a small group.

Daniel Stillman:

Hmm. That sends really interesting message, that it's the person who made it is sharing it. It's not feedback. Was it explicitly celebration or is it a "Here it is"?

David Hoffman:

We had a big clapping culture, so after anyone would present anything, people would snapper clap, and I think that sort of just celebrating small wins and being excited for each other's progress was sort of key to the culture we built.

Daniel Stillman:

Yeah, that's really awesome and beautiful stuff, and I wish I could push more on this, but I do want to respect your time and tie up the end of what it's like to reach out to Samir, because I know you took some time between when Next Big Sound was acquired. You stayed for a while and then you had a child, you traveled the world, you took a real breather. And then, at some point, what was it like calling him up and saying, "Strap in", or, "Are you interested in..." How did you start that conversation with him?

David Hoffman:

Yeah. I would love for Samir to be here for... But I can tell you some of the pieces along the way. So, I think while we were still at Pandora, I remember... Let's back up just a little bit. So, the quick connection on the story is we get to New York, have the series A, build all this software, have all these great clients, and we launch Next Big Book. Same thing for music, but in the book publishing industry. Bring on Macmillan as our first of the big five book publishers, and are gearing up for this vertical media strategy to provide analytics and insights for every major vertical as the world's changing.

At the same time, Pandora is our only blind spot. We've tried scraping them and gotten letters from their lawyers. We've met them a few times, we've put together some concepts for them, nothing's gone anywhere. They see the progress we're making, realize that they're not being included, and want to really own it, and we're their first-ever technology acquisition. They make us an offer we can't refuse. We decide to go that route instead of raising a Series B, great outcome for everyone involved.

So we get to Pandora, first time I've ever worked anywhere that wasn't for myself, trying to just learn as much as I can, but also getting curious about things. I mean, I spent my twenties, 20 to 27 or 28 when we sold the company, working nonstop, literally living with my coworkers. You suddenly have this luxury of time, which is even more impactful than money, and you're like, "Who am I? What do I want to do with my life? What did I miss over the last eight years?" Because I was so heads-down. How do I want to spend my time? And so I did a lot of soul-searching, and walking around museums in New York, and exploring interests, and I kept coming back to design. I love design more than anything, and I kept coming back to physical things. I spent so much time staring at screens at that point. I was like, "What is in the physical world?"

And so, we were spending all this time outside of New York up in the Catskills and ended up buying this tiny little two-bedroom vacation cottage 20 minutes outside of Woodstock, and we did a gut renovation from top to bottom, and we didn't have any knowledge of this process. We didn't hire a designer, we didn't hire an architect. I talked to a few. I just hired a contractor and we designed everything ourselves. And, we would stay up at night till three o'clock in the morning, looking at pendant lights, and I narrowed down 500 choices to three, and then we'd pick one, and then they'd be the wrong size and we'd return and buy another one.

And just, we were shopping very intentionally and thoughtfully for products to design this space and design our life. We were at that sort of moment in life when you have the opportunity to do that. And that's kind of what opened the door on the next chapter. So, I remember being at Pandora and being out with some people on the team, and Samir one night, and telling them about shopping for this project and saying, "You know, we've built this taxonomy of data. We've learned from Pandora, the Music Genome project, how you can tag everything and organize it. This doesn't exist for home, and what would a taxonomy of home look like?" And we riffed on it for a little bit and then kind of dropped it. And we got to the two-year market Pandora, and I left and traveled and explored, and I just kept coming up with prototypes and building them and sending them to people and asking for feedback, Samir included.

And I thought I was building a remodeled operating system for a while-

Daniel Stillman:

Yeah, I remember that. That is-

David Hoffman:

... A marketplace. Kept coming back to this selection sheet. So, what are all the things that need to be specified when you're designing a space, and how does that live? And then I ended up working with a few different people on it, and I remember it got... I was getting frustrated with Samir. I was like, "Come work with me on this." He's like, "Man, I'm busy." And so, I would do things like say, "Hey, I don't care what we work on. I just want to work on something together."

And I was in Florida at the time, he was in New York. I flew up for two nights and stayed at his apartment, and we just built a stupid side project that didn't go anywhere, but just had fun building together; or I'd be visiting the city and go out to lunch with another friend and talk about an idea. It's just this exploration process. I finally got frustrated because he was still at Pandora, and then taking some time, and I just hired a developer on Upwork and designed everything myself. Wrote the HTML and CSS and had him build this contract proposal application software where a part of it was selections.

And on the selections piece, I wanted it to be able to support any product that you could add so you could see the products together, and the Upwork developer didn't know how to do that, and it was very similar to what we built at Next Big Sound, adding artists from anywhere online. So I sent it to Samir. I'm like, "Samir, I've got the smallest project for you. I just need you to build this scraper so you can add products to this selection sheet thing I'm building."

And so we built it and got it in there and it was working, and it was really cool. And we were like, "There's something here." So we went out to... I met up with him in Green Point where I was living at the time, and we walked over to the river there. I was like, "Look, I really want to work with you again on this next thing. I don't know what that looks like, but it's been fun working on this piece. Let's keep exploring." And it was this... it wasn't the sort of thing where it was like, okay, we sold the last thing. We're obviously going to work together on the next thing. It was like a, "Holy shit, that was an emotional roller coaster. Crazy last eight years. We all need time to decompress and then figure out what we're doing next."

Daniel Stillman:

Yeah. And I can see how the arc of this conversation was planted in that one and you kept returning to it.

David Hoffman:

Yeah.

Daniel Stillman:

We're at time, so I guess I will ask you for your parting thoughts. I mean, obviously I'll stay on this call as long as you'll let me, but I want to respect your time, because I know your wife's in the background.

David Hoffman:

No.

Daniel Stillman:

You have a life. But-

David Hoffman:

Sorry I've been long-winded. I do actually have to jump to talk to a VC right now, but-

Daniel Stillman:

No, that is more important. What is the-

David Hoffman:

But I think-

Daniel Stillman:

... the one... Yeah, sorry. What would be your closing thoughts? Wherever you want to end this.

David Hoffman:

The thing that you made me see on this call... And I'm really grateful for, I want thank you for... is this idea of a conversation over a long arc of time, over a decade or multiple decades. And I rarely reflect at that sort of scale, but the serendipity of how things connect over time and the way the small decisions that you make ripple really stood out to me in this.

Daniel Stillman:

That is beautiful. That touches me. I really, I'm so grateful for that. I'm grateful for the time. Good luck with the call.

David Hoffman:

Thank you.

Daniel Stillman:

I'll just assume that we can call scene and we don't have to bleep anything out.

David Hoffman:

No, it was perfect. Thank you so much, Daniel. Let's talk soon.

Daniel Stillman:

Thank you, brother.

Cofounder Conversations: Pivoting while Staying Sane

My guests today, Ryan Horrigan and Armando Kirwin, bonded over their mutual fascination with the future of entertainment and their desire to do something innovative, which led to the creation of their current company, Artie. We talk about pivots and micro pivots and staying sane through the million tiny conversations Cofounders need to navigate.

Ryan, the CEO, and Armando, President and co-founder of Artie have a pretty radical vision for the future of social media— namely, to make TikTok, Instagram, Twitter and other social media apps the gaming consoles of the future.

Before co-founding Artie, Ryan served as Chief Content Officer of the Comcast-backed VR & AR startup Felix & Paul Studios. He oversaw the development and production of feature films, including Academy Award Best Picture Winner “12 Years A Slave.” at Fox/New Regency, and is a two-time Emmy Award winner for immersive entertainment projects he produced with President Barack Obama and NASA, as well as a Peabody Award winner.

Armando has been in the VFX world for over fifteen years, working with numerous award-winning directors, including two-time Academy Award nominee Lucy Walker, Sundance Grand Jury prize nominee Sandy Smolan on The Click Effect, which was nominated for an Emmy; and Imraan Ismail on The Displaced, which won the Grand Prix at Cannes. He also produced Take Flight, starring Benicio del Toro, Michael Fassbender, and Charlize Theron. His most recent VR film, Nothing is Safe (2022), was an official selection of the Cannes Marché du Film.

While movies are a wonderful industry, they both saw the power and potential of gaming as a storytelling platform - and a financial juggernaut. If you didn’t know: According to a report by SuperData Research, the global gaming market was valued at $159.3 billion in 2020. This includes revenue from console games, PC games, mobile games, and esports. Let’s put that into perspective: the music industry was valued at $19.1 billion in 2020, and the movie industry at $41.7 billion. That means the gaming industry is more than three times the size of the music industry and almost four times the size of the movie industry.

TikTok used to be where people just watched videos (as of this writing, TikTok and Netflix are nearly tied for eyeball-hours). Now, hundreds of thousands of people are playing games on TikTok thanks to Artie and the technology breakthroughs that make streaming app-quality games from within social media apps possible.

But how did they get here? Through a million micro conversations about data, signals, stakeholders and what it all means. Artie is where are are today not because of one big pivot, but many, many micro-pivots over the course of years.

Pivots impact the team - who you needed on staff when you were focused on one path isn’t always who you need when you’ve decided to shift directions. Communication between departments and involving the team more is important - which means being intentional about regular check-ins and interdepartmental communication, but eventually, it comes down to the co-founder conversation - owning the choices that need to be made and moving forward, all while making sure you stay healthy and sane.

Pivots vs Shaping Clay

I loved this metaphor from Ryan, where he suggested that, from the outside, to investors, bloggers and customers, a company may have pivoted once, or a few times. From the inside, there are daily conversations, where the product is being shaped like clay, remade, refocused, almost constantly.

“Listen to your body, Have a Coach and a Therapist”

This was one of my favorite insights from this conversation. It’s not often that men talk openly about mental health and needing support. Ryan and Armando both have a coach (although they meet with that coach separately) and Armando advocated for having a therapist, while Ryan discussed how they got much much more intentional about listening to their bodies and taking down time. Armando suggests that therapy focuses on self-awareness, learning about yourself and your patterns, while his coaching focuses on future outcomes and goals.

“You have to care deeply about your people, but at the same time, you can't care about what they think of you”

Ryan quotes what he describes as a harsh-sounding notion from Dick Costello when he was at Twitter: In Ryan’s experience, when you make a tough decision, you can't worry about everyone's collective feelings (even though you DO care about them as people and teammates). You have to make the decision that you, as the leader, believe needs to be made.

As a founder, you have to make and own tough decisions.

Ryan points out that, at the end of the day, you can't ignore tough decisions. You can’t have someone else do it for you. He suggests that while these moments are hard, it’s helpful to focus on the people who are still with you and the ultimate goals you’re trying to achieve.

Links, Quotes, Notes and Resources

https://www.artie.com/

Armandokirwin.com

Minute 13

Daniel Stillman:

Armando, I'm wondering how you as a co-founding team approach the dialogue, the deliberation, the discussion, the decision around, let's do more of this, let's do less of this, and to make the decision to be all in. How does that get navigated. Because it's complex?

Armando Kirwin:

I wish it was a decision. Because honestly, it's not. It's more a year of throwing yourself against a wall and then eventually being like, okay, well we tried really hard and that's just not working. So like Ryan said, when we were attempting to combine AI and game engines and do all of that instantly on social media, we tried really, really, really hard. We made demos with huge IP that we can't talk about. We hired all the right people, which we had to poach from other bigger companies. And it's a lot. And then you're hearing, "Oh wait, this investor's saying that, or the feedback we're getting from this person who is trying this game out is this."

So it's not just one decision, but eventually, if you're honest... I think it's really hard, I think people get stuck when the decision that they made, they should have made 12 months ago and they're still not confronting it. That's when you're in trouble. But it's okay to take a little bit of time to make sure. And for us, that's what we did. We sunset a lot of our AI efforts in our second year, and then we just doubled down on... Everyone will tell you, you'll be like, "Oh, this AI stuff is not quite working. But I love the idea of playing a game on Instagram and TikTok." That's so crazy to me. So you'll be hearing it and then you just have to come to terms with bit.

Minute 22

Daniel Stillman:

What do you think are the conversational skills that founders should be thinking about that enable them to have those dialogues on a regular basis? Because it's not one big conversation, it's many, many smaller conversations. What are the skills that you feel you're bringing into those dialogues with each other that make it possible to have those?

Armando Kirwin:

...that's a hard one. But I think part of it is, I think you have to be okay. You have to be able to function in this really messy, noisy situation without wanting to kill each other. So that's a big part of it. Because you are, it's just so asymmetrical. I might hear one thing from one person, Ryan might hear another thing from someone else, or we might learn something a week apart or what... We have to constantly be sharing, but also with the team. So you're really signing up for a... It's pretty frothy environment. So I think part of the skillset is to somehow be okay with that. I think a lot of people can... It can be hard to take, and you can maybe end up just doubling down on your vision and not listening and then you're screwed. So I think that probably one of the skills is just somehow trying to stay calm, knowing that it's just really... It is a pretty sloppy process, to be honest.

Ryan Horrigan:

Yeah, I agree. I think you have to be willing to kill your ideas, basically. You have to be willing to have these moments where you think you have brilliance, but then on the other hand, be ready to kill them at a moment's notice and be okay with it. So you have to constantly find some source of energy to keep coming at it with new angles and ideas. And you need to know when there's a big thing when you're like, "Hey, we're going to let go of all this AI stuff and put it on the shelf and just focus on this other thing." You have to be willing to do that.

Minute 25

Armando Kirwin:

So we're always trying to figure out what, what's actually working here? What do people want? What are people interested in? How can we reach a lot of people? Stuff that. And that helps get you through the more emotional side of like, wow, we just spent a year on this crazy thing and we're going to not use it.

Daniel Stillman:

So it sounds like keeping the north star in mind is something that's helpful. I saw Ryan, yes you, sir, in the back. You're raising your hand.

Ryan Horrigan:

Well, there's one other thing, which I don't know if this is part of another conversation you want to have, but also when you make a pivot, as Armando alluded to earlier, you may then find yourself with some mismatch or imbalance on the team, where now suddenly you have the wrong people on the team. So that then requires, in many situations, either recalibrating those team members into different roles or different functions or parting ways with people, which as you know, anyone can imagine is very difficult. And then feels as a founder, you have to A, own that, and B, you have to acknowledge that your decision-making process along the way bears responsibility in that, right?

So if you've decided to pivot the company, and now there's three people who you're going to have to part ways with, that's on you. And you have to own that. And I think the wrong decision would be to bury your head in the sand and try to keep them if they really shouldn't be there, because you're also stifling their careers too.

Minute 32

Ryan Horrigan:

Can I say one thing that was a quote from, I think it's from a few years ago, at a TechCrunch Disrupt. I just saw it on YouTube.

I think it was Dick Costello when he was at Twitter. And he was talking about team building culture and making tough decisions and dealing with tough things like these things. And he said something that really resonated with me. It sounds cold, but if you think about it makes sense from a founder point of view. He said, "As a founder, you have to care deeply about your people, but at the same time you can't care about what they think of you." And I thought that was really interesting. And his point there, what I think he was trying to say was, you actually do have to operate authentically in a way that shows empathy and caring. It has to be real because these are your people and this is your company. But when you make a tough decision, you can't worry about everyone's collective feelings. You have to make the decision that you as the leader believe needs to be made. And you can't get weighed down by what someone might think about that. You have to move forward. And that is the hard part, right?

AI Summary

Ryan and Armando bonded over their mutual fascination with the future of entertainment and their desire to do something innovative, which led to the creation of their current company, Artie.

Pivoting may require recalibrating team members or parting ways with people, which can be difficult and requires owning the decision-making process. Communication between departments and involving the team more is important for successful check-ins and interdepartmental communication.

Key Moments

(1:59) - Ryan and Armando bonded over their mutual fascination with the future of entertainment and their desire to do something innovative

(5:24) - Ryan talks about how the film industry was changing and how VR was seen as a potential outlet for the future of entertainment

(9:51) - Ryan talks about the opportunity in mobile content and how it led them to explore bringing speech recognition and computer vision into mobile gaming

(12:02) - Ryan Horrigan had a midlife crisis in his 20s and left the film industry to pursue VR as an outlet for the future of entertainment

(15:39) - Ryan explained how they explored incorporating AI into mobile gaming but ultimately decided to strip it away and focus on solving problems and reducing friction for players

(22:35) - Ryan and Daniel discuss the challenges they faced with creating an AI-driven narrative game and how it wasn't scalable or replayable, and how they struggled to pitch it to other game publishers.

(26:12) - Pivoting may require recalibrating team members or parting ways with people, which can be difficult and requires owning the decision-making process

(29:33) - Ryan and Armando discuss the importance of owning tough decisions as a founder, even if it affects team members

(32:37) - Ryan shares advice from Dick Costello about caring deeply for your people but not worrying about what they think of you when making tough decisions

(44:57) - Ryan discusses different types of pivots and how to communicate them to investors, emphasizing the importance of having the right data points and assessing the pivot intelligently

(26:24) - Daniel asks about conversational skills needed for founders to have regular dialogues with each other, Armando mentions the need to be okay with a messy process, Ryan emphasizes the need to be willing to kill ideas and defend others, and keeping the North Star in mind helps

(34:36) - Ryan adds that founders must take ownership of tough decisions and prioritize their own health, as stress can manifest physically

(54:04) - Ryan suggests aiming for consent rather than consensus when making decisions as a company, and shares a process for identifying dissenting opinions based on business considerations rather than emotions or egos

MOre About Armando and Ryan

About Armando

Originally from New Mexico, Armando began his career in 2007, working primarily as a VFX and indie film producer.

In 2015, he embarked on a journey into the nascent virtual reality industry, joining one of the leading VR production companies as a Post Producer, Executive Producer, and Head of Post Production. During this time he worked with numerous award-winning directors, including: two-time Academy Award nominee Lucy Walker on A History of Cuban Dance and The Vodou Healer; Sundance Grand Jury prize nominee Sandy Smolan on The Click Effect, which was nominated for an Emmy; and Imraan Ismail on The Displaced, which won the Grand Prix at Cannes. He also produced Take Flight, starring Benicio del Toro, Michael Fassbender, and Charlize Theron.

In 2016, Armando began working as a freelance Director of Virtual Reality. He collaborated with Academy Award Best Picture nominee, Luca Guadagnino, on two VR films featuring acclaimed artists Rob Pruitt and Taryn Simon, and with Independent Spirit Award winner Gina Prince-Bythewood on LA Noir, a nine-episode VR film noir series, starring Natalie Portman, Kristen Stewart, and Don Cheadle, which won an AICP Next award.

In 2017, Armando began writing and directing his own work, starting with Mercy, a VR film shot on location in Cameroon that combined 360-degree documentary footage with 3D animated dream sequences designed by social impact artist, Sutu. The film was an official selection at Tribeca and SXSW and was exhibited at the National Center for Civil and Human Rights in Atlanta, Georgia. He then directed A Life in Flowers (2019), featuring renowned botanical sculptor, Azuma Makoto. Participants reflected on themes of life and death during a conversation with artificial intelligence-powered, real-time renderings of flowers. The project was in competition at the Venice Biennale, received a favorable review by Art Critique, and was on display at the Phi Centre in Montreal, Canada. His most recent VR film, Nothing is Safe (2022), was an official selection of the Cannes Marché du Film.

Armando’s work in interactive VR and artificial intelligence led to an interest in video games. In 2018, he cofounded Artie, a next-gen video game company that has attracted nearly $40 million in venture capital from numerous notable investors, including: Warner Music Group, Tyler and Cameron Winklevoss, and YouTube founder Chad Hurley.

In 2023, LA Weekly named Armando one of the top ten innovative minds disrupting the entertainment space. He has spoken frequently about the future of entertainment at venues such as: Sundance, Google, Facebook, SXSW, and the Toronto International Film Festival.

About Ryan

Ryan is the co-founder and CEO of Artie, a next-gen mobile gaming platform. We bring high-quality games directly to players on the world’s most popular social media and video apps – with no additional app download required. With Artie, people can easily discover, instantly play and share games with their friends on TikTok, Instagram, YouTube, Facebook, WhatsApp, and more.

By circumventing app stores, we eliminate the friction of app downloads, bypass Apple and Google’s 30% store fees, and dramatically reduce customer acquisition costs while boosting virality compared to today's mobile games.

The Artie team is from Riot Games, Activision/Blizzard, EA, Zynga, King, Glu Mobile, Playtika, Jam City, Playstation, Tencent, Apple, Amazon, Meta, Snap, Lyft, and Disney.

Artie's investors include Digital (Steve Cohen, Mark Daniel, Benjamin Milstein); YouTube founder Chad Hurley; Zynga founder Mark Pincus; Roblox Chief Product Officer Manuel Bronstein; Kevin Durant & Rich Kleiman; Naomi Osaka; Tyler & Cameron Winklevoss; Cyan Banister; Warner Music Group; Allen & Company; Harris Blitzer Sports & Entertainment; and former Disney D2C Chairman and TikTok CEO, Kevin Mayer.

Before co-founding Artie, Ryan served as Chief Content Officer of the Comcast-backed VR & AR startup Felix & Paul Studios, where he oversaw content and business development, strategy, and partnerships.

Prior to Felix & Paul, Ryan was a studio executive at Fox/New Regency. He oversaw the development and production of feature films, including Academy Award Best Picture Winner “12 Years A Slave.” He began his career in the Motion Picture department at CAA and at Paramount Pictures.

Ryan is a two-time Emmy Award winner for immersive entertainment projects he produced with President Barack Obama and NASA, as well as a Peabody Award winner. He’s a former Hollywood Reporter 35 Under 35 honoree and has spoken at E3, Cannes, Sundance, Google, Meta, among other events.

Full Transcript

Daniel Stillman:

I will officially welcome you both to the Conversation Factory. Ryan, Armando, thanks for making time today. I really appreciate it.

Ryan Horrigan:

Thanks for having us.

Armando Kirwin:

Good to be here. Yeah, excited.

Daniel Stillman:

So my first question is how did you two meet and what are your favorite snacks?

Armando Kirwin:

So we met at a conference site, I think officially, but I had known about Ryan because we had both gone into virtual reality when that was at its peak. And we were both at two really successful VR companies. And Ryan had this reputation of being this absolute killer who could get all the money and all the best partnerships and all the best IP.

Daniel Stillman:

That's a pretty good rep.

Armando Kirwin:

So I knew of Ryan, but I don't think we officially met until the conference, right Ryan? Like in San Francisco, I think?

Ryan Horrigan:

Yeah, it was the San Francisco Film Festival. We were on a panel together. And I don't remember what we were talking about, probably just VR and how it's going to change the world. And this was probably in 2016, I'm guessing, or '17.

Armando Kirwin:

Yeah.

Daniel Stillman:

So you guys were on a panel together, hadn't met, and this is the meet cute.

Armando Kirwin:

Yes.

Daniel Stillman:

This is the moment.

Armando Kirwin:

Yeah, and then we started chatting, and I remember thinking, "This dude should be the CEO of a company." I think I even told Ryan that. I was like, "You should be the CEO." But yeah, those were the early days for sure.

Ryan Horrigan:

And I also was like, "Well, Armando, you understand technology in a way that I don't. I'm just a business content strategy guy," almost like a salesman in better terms.

Armando Kirwin:

No, maybe in the beginning. I think that you've become a technologist as well at this point. But maybe in that era, yeah.

Ryan Horrigan:

Yeah. But we started talking about the future of entertainment. I think that was the reason why we started hanging out and talking is we had this mutual fascination with the future of entertainment. And I think that's one of the reasons why we were in VR, because we both had come from traditional film entertainment, the movie business, from different corners of it.

Armando Kirwin:

Yeah.

Ryan Horrigan:

And we both wanted to leave that business to do something more innovative, more bleeding edge and interesting.

Armando Kirwin:

Yeah, exactly. And we-

Daniel Stillman:

[inaudible 00:02:31] going to avoid the snack cover question completely.

Armando Kirwin:

Oh yeah, the snacks.

Daniel Stillman:

You're just going to leave that aside. I only asked this specific-

Armando Kirwin:

That's hard.

Daniel Stillman:

...because I just had a snack before I got here, and I'll just go first because I had a little spoonful of peanut butter. And for me, peanut butter is just this deeply soothing... It just always gets a little bit of protein, a little bit of flavor, and just gets me above the line again. So that's the reason why it's top of line for me is the snack that helps you just get through that bridge in the day. It's a completely personal and totally irrelevant question.

Armando Kirwin:

Does coffee count as a snack?

Daniel Stillman:

That's a great question, Armando.

Ryan Horrigan:

Yeah.

Daniel Stillman:

Now we're going to have a philosophical-

Armando Kirwin:

I drink a lot of coffee these days. Yeah,

Ryan Horrigan:

I think it does, it's a like ritual.

Armando Kirwin:

Yeah.

Daniel Stillman:

How much milk and sugar do you put in your coffee? Is it enough to...

Armando Kirwin:

That number's been creeping up for sure. Slowly but surely. I used to be like, no, you can't do that. And now I'm like, ah, I need all the support I can get. You know?

Daniel Stillman:

Yeah. No, I totally understand.

Ryan Horrigan:

So my answer would be if I'm trying to be healthy, which is hard, some nuts or a smoothie. And if I'm being my true self, it would be french fries probably, or something like that.

Daniel Stillman:

French fries as a snack is a really interesting concept.

Ryan Horrigan:

Yeah. Because it could go with a meal or you could just have a side of french fries for no reason, for your lunch. Which is a little strange, but I do that sometimes.

Daniel Stillman:

Whatever to get you over the hump. So that's good to know. Now I know what to send you guys in the middle of the day. If I was going to send a delivery to just make your day peak, that would be hot fries and a steaming cup of Joe. That's really good to know.

Armando Kirwin:

I mean, what else do you need, really?

Daniel Stillman:

Honestly, nothing else.

Armando Kirwin:

Yeah. Honestly, yeah.

Daniel Stillman:

So this moment when you two met is really fascinating to me. I have to be honest, because the formation of human relationships is always a crazy mystery. Because there's tons of people you've met, tons of people you've probably been on panels with where you didn't have a second conversation and a third and a fourth and a fifth. What do you think kept you having a conversation all that time?

Armando Kirwin:

I think, well, part of it is that we had both been in the film industry for about 10 years, even though I was coming up through visual effects and Ryan was coming from the studio side. So there's different perspectives, but there's a shared knowledge base. So we could have conversations easily on a range of topics that we didn't have to start at basics. There was a lot of shared knowledge. But there was also a lot of shared pain because we had been through VR. And in a lot of ways our company today is based on that experience, like the way we're distributing games is almost an answer to how difficult it was to get things done in VR. So I think it was a shared context, both good and bad, that kick started things and made it pretty natural.

Ryan Horrigan:

Same with film and TV too. I think I was in the film business when it was starting to shrink and become different. I came to Hollywood to start my first job out of college when the first writer strike was happening, or the most recent writer strike... Well, I don't even know if it's... One of the most recent writer strikes. In 2006, and that was when we had iPhones. We had, not yet streaming, but we had maybe early YouTube if my dates are correct or we were on the precipice of that. So everything was starting to change, but people in traditional media hadn't recognized it yet. But I think there's some people like myself who were younger who were living online, who were starting to read the tea leaves.

So I think people like Armando and I were just of this generation where, I don't know, I'm not going to speak for Armando, but I grew up my whole life wanting to be in the movies. Not in the movies, but working on movies as a producer or a executive or a writer or a director. And to go from being 10 years old and being a cinephile to dreaming about that for the next 10 years while you're in school and then getting to do it, but then the rug gets pulled out from under you and you're like, oh wait, this whole medium has changed. Not because it's not a great medium, but consumer habits have changed. Technology is changed the way we consume content.

So I had this, it was almost having a midlife crisis but in your twenties over your profession that you had obsessed about forever. Where you're like, wait a second, this is not what it was supposed to be. And I'm like a decade too late, at least.

Daniel Stillman:

Oh man.

Ryan Horrigan:

So that's kind of what led me into VR. I had five years in the film business where I was climbing the ranks and I was working on some Oscar winning movies, but I was deeply unhappy because I felt movies were becoming less culturally relevant, particularly with young people. And I could see that economically the business was shrinking and changing and not in a good way. So for me, VR was an outlet or a stepping stone to the future where I was like, okay, I can have one foot in Hollywood and one foot in Silicon Valley. VR is being supported by Google and Facebook, among others, in a significant way.

This might be the future of entertainment where I can now be in the content, which is a whole different experience. And I still think that the concept of that is incredible. It's just that everyone got way too ahead of themselves in terms of how long or hard it would be. It's kind of like that quote, and I'm going to butcher it: a lot less happens in a year than you expect, but a lot more happens in 10 years than you could imagine your wildest dreams. It's that kind of thing. I think we all thought VR would just change the world in a year or two, but it might end up doing so in 10 plus years.

Daniel Stillman:

So Armando, was that some of the shared pain that Ryan was talking through, what the state of the industry and where you saw it-

Armando Kirwin:

Yeah.

Daniel Stillman:

...where it was and where you wanted it to go?

Armando Kirwin:

Exactly. And I think we were both at these really cool VR startups, some of the best funded, doing the best work. But just in a nutshell, there just weren't enough people. We couldn't reach enough people. 'Cause there was so much friction, right? You have to go buy this thing. And at the time, they were even much clunkier than they are even today.

And so I think it's hard when you're doing your best work creatively and technically, you're pushing the envelope, you're learning new things, and then no one even knows what you're doing.

Daniel Stillman:

Yeah.

Armando Kirwin:

It's fun, it was really fun. And some of the coolest people I've ever met were in VR because they were true mavericks and they were just such interesting thinkers. But when we started this company, the thing that's actually been persistent for our entire journey was this idea of how do we reach the most people as easily as possible? And that's the one part of our vision that's never changed. And I think it was a direct response to VR. In hindsight, I don't know that I was super aware of it at the time-

Ryan Horrigan:

Yeah.

Armando Kirwin:

...but now it's like really-

Ryan Horrigan:

In Hollywood.

Armando Kirwin:

...it was crystal clear. Yeah.

Ryan Horrigan:

And film and TV too. It was film, and maybe not TV with Netflix and streaming, but theatrical film in a theater, it was reaching fewer people, particularly young people. So I think we were just thinking to ourselves, well, if VR is not here today like we all thought it was, in a massive way, then mobile is still the dominant platform for this foreseeable future. But what is the opportunity in mobile, in the content space? We have YouTube, we have streaming video, we have social networks, we have app based mobile games that go through Apple and Google. Where's the white space? And that's what led us to a number of thoughts.

The first was we were actually super early, because right now we're in this AI, generative AI hype cycle right now it seems like. And some of this stuff is awesome, but we were actually in the first hype cycle of that when we started Artie in late 2018, there was a little hype cycle. And what we were trying to do was bring speech recognition, natural language understanding and computer vision into mobile gaming in a way that would let players interact with game characters or NPCs in a more personalized, pseudo intelligent way. So imagine talking to your game characters and having a conversation as you play the game. That'd be pretty cool. Or instead of watching boring cut scenes or cinematics, those were more interactive and more human, more uniquely human. So we went down this path for about a year or so exploring that, and that was what we started Artie to do, all while also trying to do it over the top and through the mobile web. Which goes to what Armando was saying, which is reaching a lot of people.

And we're trying to do these two things at once. And I think, as you find in startups, don't try to do more than one thing, do one thing really well. And I think we've had a couple of instances over our trajectory where the bringing interactive entertainment or games to people over the top, to use a video term, has been the constant. But we've gotten involved in a couple of other things along the way, AI being one of them. I think what we found out with AI stuff is also that VR is going to take a long time. We had cracked the input side of things of we can get a game listening to your voice and then converting that into text and then using that text to make decisions in the game. But we hadn't figured out the generative dialogue part, the stuff that GTP-4 I guess today does really well.

And then the output of real time speech synthesis and coding that generative dialogue into a voice of a character you know in real time. So there's a lot of hard stuff there. And then the computer vision, whole separate thing, recognizing your engagement or your contextual stuff to your environment. So we still believe in all that stuff in the long term, but we also found it really limited us in terms of the type of games or interactive experiences we could make.

Daniel Stillman:

Yes.

Ryan Horrigan:

So we at some point decided to strip that away for now and put that on the shelf, and then just focus on bringing really great mobile games to people in a unique and differentiated way that would solve problems, mainly friction, for players.

Daniel Stillman:

So this, I think, a really fundamental question for us to peel some layers of the onion on around the conversation at the heart of a pivot, deciding to double down on one thing or to leave something else behind. Armando, I'm wondering how you as a co-founding team approach the dialogue, the deliberation, the discussion, the decision around, let's do more of this, let's do less of this, and to make the decision to be all in. How does that get navigated. Because it's complex?

Armando Kirwin:

I wish it was a decision. Because honestly, it's not. It's more a year of throwing yourself against a wall and then eventually being like, okay, well we tried really hard and that's just not working. So like Ryan said, when we were attempting to combine AI and game engines and do all of that instantly on social media, we tried really, really, really hard. We made demos with huge IP that we can't talk about. We hired all the right people, which we had to poach from other bigger companies. And it's a lot. And then you're hearing, "Oh wait, this investor's saying that, or the feedback we're getting from this person who is trying this game out is this."

So it's not just one decision, but eventually, if you're honest... I think it's really hard, I think people get stuck when the decision that they made, they should have made 12 months ago and they're still not confronting it. That's when you're in trouble. But it's okay to take a little bit of time to make sure. And for us, that's what we did. We sunset a lot of our AI efforts in our second year, and then we just doubled down on... Everyone will tell you, you'll be like, "Oh, this AI stuff is not quite working. But I love the idea of playing a game on Instagram and TikTok." That's so crazy to me. So you'll be hearing it and then you just have to come to terms with bit.

Daniel Stillman:

Ryan, does that line up with your perspective? A million small discussions around-

Ryan Horrigan:

Oh yeah.

Daniel Stillman:

...signals you're hearing.

Ryan Horrigan:

This sounds horrible to say, but if you're a founder I think you understand this. If you would be like, how many times has the company pivoted? I think to anyone from the outside looking in, it's once or once and a half. But to us it feels like micro pivots every day. It's almost like you're trying to constantly get data points from users or from investors or other people. And the more data points, obviously the better. And you're constantly shaping this clay.

Daniel Stillman:

Yes.

Ryan Horrigan:

You're kind of like, together, you're shaping this thing with new information every day. So to Armando's point, it's really hard to say do a pivot in a day. I think that there's probably almost no company that has done that.

Daniel Stillman:

Yeah.

Ryan Horrigan:

It might look that, But there's a lot of conversations and data points, and it's probably different for every company and every pivot. But for us, yeah, I think this first one, this one out of AI was over the course of maybe a year in 2019 and early 2020 probably. But I think by the time the pandemic started, we knew directionally where we were going, except we had a whole new problem, which is a global pandemic.

Daniel Stillman:

Yeah. And we can get to that in a moment. I wanna-

Armando Kirwin:

You also have to imagine, okay, now certain people on your team aren't relevant, but you need all these new people. And hiring, and that takes a long time. And also sometimes you learn certain things as you're building. As we built out some of our AI tech and we got a really, really nuanced understanding of the costs of operating it, that also factors in. So there are certain things you just can't even know conversationally that involve the types of people on your team or the nitty-gritty of getting this tech actually working and stuff that. So yeah, it takes time. It takes time.

Ryan Horrigan:

And that stuff's really hard, to those two points. We found out with this AI stuff that the only type of game that made sense for us to create was a voice driven narrative game. Think of it like a game meets Alexa, if you've ever done any of those interactive stories or choose your own adventures on Alexa. Or if you're familiar with the choose your own adventures on Netflix, like Bandersnatch is probably the first and most popular one. We were making games like that where you could be with a superhero character or a movie character and go through an interactive story where you're like their companion. And that is or was a genre that has been successful. But what we learned is it's actually a really tough genre, because it's actually more akin to film or TV in the sense that you have to make lots of content that will be experienced one time, or much of it will not be seen by the player at all because you're choosing your own path.

Daniel Stillman:

Oh my Lord.

Ryan Horrigan:

So it's exponential content creation. So there was this irony. It was like-

Daniel Stillman:

Which doesn't, all that surface material, that surface area doesn't even get exposed to the customer-

Ryan Horrigan:

Correct.

Daniel Stillman:

...necessarily. Wow.

Ryan Horrigan:

Correct. So that was the only genre that really made sense, that was so obvious to us. But it was also the genre that required the most art resources and production resources. And it wasn't a replayable game. So we were like, oh, this is actually horrible because this doesn't scale right? And it's really expensive and laborious, and it's antithetical to the idea of AI. AI should make things easier and more automated. And in fact, by having AI as a feature for players, it was making our game creation more complicated. And then when we went to go talk, this was the real test, we went to go talk to the founders of some of the biggest game publishers, mobile game publishers in the world. We happen to know three or four of them, one of them's our investor. What became clear to us was everyone thought this was neat, but they didn't feel there was a way to make it make sense for their current hit games. And their current hit games didn't need it, they were already successful.

So we started to compare ourselves as an analogy to Niantic, who makes Pokemon Go. In that we had heard a lot about their early story, and ours was starting to feel similar. And obviously they're very successful and it worked out for them, but we felt the outcome was going to be very much a coin flip or binary, and we didn't like the odds. So what I mean by that is Niantic was pitching a new type of gameplay experience to other game developers initially as a platform. So they were pitching GPS or out in the world games, there's probably a better... Location based games. And they were pitching AR, the combination of the two. And that's what Pokemon Go is. And I think the game publishers out there, from what I heard, didn't really respond to that. They're like, "Hey, we're not making games like that right now, and our games are already successful, so why are we talking?"

And then when they actually thought about it, they were like, "Okay, we're going to have to do this ourselves. We're going to have to make our own game," which they did. And then they re-skinned it as Pokemon Go and they got the rights and the game is still very successful, but there haven't been other games like it, which is interesting. No one has copied them. There aren't any other GPS AR games out there of note. Not really. And most people don't use the AR mode when they play Pokemon Go according to the data.

So anyway, it's really interesting, and we felt like we were going to go down that path. We're like, "Okay, we're going to be make these voice voice-driven games. No one else is going to care, none of the other publishers because it's just weird. And we're going to have to make a hit game with huge IP to make this work.

Daniel Stillman:

Right, which is very heavy approach.

Ryan Horrigan:

Yes. It doesn't feel a startup, like a scalable startup.

Daniel Stillman:

Right. Whereas the idea is let's make a platform and many people will use the platform.

Ryan Horrigan:

Yes.

Daniel Stillman:

So a couple of things that I'm hearing, which I want to make sure I've gotten this right, 'cause this is important stuff. One is that the feedback loops, the concept is sometimes this idea of a pace layer. That certain things take a while to get the feedback loop, to find out what customers think, to find out what the market wants, to find out how the technology really plays out to find out what the costs really are. It can take multiple months up to a year to make sense of all of those signals that are... and what all the constraints really are.

And you're having conversations constantly. Micro-pivoting on what does this mean? What does that mean? Are we seeing what we're seeing? And I think the question I have is, because you mentioned we're having lots of conversations, and that's of course the thing I care the most about. What do you think are the conversational skills that founders should be thinking about that enable them to have those dialogues on a regular basis? Because it's not one big conversation, it's many, many smaller conversations. What are the skills that you feel you're bringing into those dialogues with each other that make it possible to have those?

Armando Kirwin:

That's a hard-

Daniel Stillman:

It is.

Armando Kirwin:

...that's a hard one. But I think part of it is, I think you have to be okay. You have to be able to function in this really messy, noisy situation without wanting to kill each other. So that's a big part of it. Because you are, it's just so asymmetrical. I might hear one thing from one person, Ryan might hear another thing from someone else, or we might learn something a week apart or what... We have to constantly be sharing, but also with the team. So you're really signing up for a... It's pretty frothy environment. So I think part of the skillset is to somehow be okay with that. I think a lot of people can... It can be hard to take, and you can maybe end up just doubling down on your vision and not listening and then you're screwed. So I think that probably one of the skills is just somehow trying to stay calm, knowing that it's just really... It is a pretty sloppy process, to be honest.

Daniel Stillman:

Yeah, yeah.

Ryan Horrigan:

Yeah, I agree. I think you have to be willing to kill your ideas, basically. You have to be willing to have these moments where you think you have brilliance, but then on the other hand, be ready to kill them at a moment's notice and be okay with it. So you have to constantly find some source of energy to keep coming at it with new angles and ideas. And you need to know when there's a big thing when you're like, "Hey, we're going to let go of all this AI stuff and put it on the shelf and just focus on this other thing." You have to be willing to do that. And not everyone is, and I think there's this spectrum of when's the right moment to make that decision? When is too early, when is too late? But I think on the other hand, you also want to have conviction on the things that really matter.

So you have to be able to do both things. You have to be able to kill things and not get too bummed out and have fresh ideas, but also be able to defend things and continue with things when they get hard. So knowing the difference between the two is difficult.

Daniel Stillman:

Yeah, that is a needle to thread. You're right, Armando, it's not trivial, for sure.

Armando Kirwin:

Yeah, it's not trivial. But that's also the difference between a goal and a piece of technology. If you're just broadly interested in the future of entertainment, yeah, you're going to be messing around with all kinds of stuff. You're going to be looking into the VR, AR, you're going to be curious about blockchain, you're going to be curious about AI. You might bring some of that stuff into your efforts, learn some stuff. So I think that you're still moving forward if you don't get too married to a specific idea or technology, per se.

Daniel Stillman:

Yeah.

Armando Kirwin:

So I think that that also helps. It's remembering the big picture, I guess is a cliche way of talking about it, but it's true.

Daniel Stillman:

Yeah.

Armando Kirwin:

So we're always trying to figure out what, what's actually working here? What do people want? What are people interested in? How can we reach a lot of people? Stuff that. And that helps get you through the more emotional side of like, wow, we just spent a year on this crazy thing and we're going to not use it.

Daniel Stillman:

So it sounds like keeping the north star in mind is something that's helpful. I saw Ryan, yes you, sir, in the back. You're raising your hand.

Ryan Horrigan:

Well, there's one other thing, which I don't know if this is part of another conversation you want to have, but also when you make a pivot, as Armando alluded to earlier, you may then find yourself with some mismatch or imbalance on the team, where now suddenly you have the wrong people on the team. So that then requires, in many situations, either recalibrating those team members into different roles or different functions or parting ways with people, which as you know, anyone can imagine is very difficult. And then feels as a founder, you have to A, own that, and B, you have to acknowledge that your decision making process along the way bears responsibility in that, right?

Daniel Stillman:

Yeah.

Ryan Horrigan:

So if you've decided to pivot the company, and now there's three people who you're going to have to part ways with, that's on you. And you have to own that. And I think the wrong decision would be to bury your head in the sand and try to keep them if they really shouldn't be there, because you're also stifling their careers too.

Daniel Stillman:

Yeah.

Ryan Horrigan:

Like we had some brilliant AI people who should go do brilliant AI things, but when we were no longer doing it doesn't make sense for them to be here with us. But that's a tough conversation.

Daniel Stillman:

Yeah, it really is.

Armando Kirwin:

It's really hard because these are high performers, they're your friends. They've done nothing wrong, you've done nothing wrong. It's really hard to sever that relationship.

Daniel Stillman:

Yeah, and you sold them a vision.

Armando Kirwin:

We actually, even last week I had to do this. And it's been years, and it was still terrible. So it's hard.

Daniel Stillman:

How do you take care of yourself? Because this is, I don't think many people think or have this discussion about the cost of a pivot. We think about, "Oh, we pivoted and we succeeded, we won. That was great." And we don't think about the shedding and the fact that, as you said, we have sold a vision, recruited these people, sometimes poached them. They may be friends and collaborators. And then we get to a point where we say, "Hey, this is where we part ways." Armando, that's hard. How do you take care of yourself emotionally and mentally? Because I definitely have friends who talk about the challenge of letting someone go just around pure economics. This is a decision you made.

Armando Kirwin:

Yeah.

Daniel Stillman:

Right?

Armando Kirwin:

It's really hard. I don't do anything special aside from therapy. We have an awesome coach. And only in the last year or so, Ryan and I have gotten much more serious about downtime and other things that we didn't have the liberty of doing in the first few years. And also just your body is pretty intuitive too. You'll crash hard and you'll phase in and out a little bit in those moments of stress, those weeks or days where you just can't. So I don't have a brilliant answer. Ryan, do you have a better answer? That wasn't great.

Daniel Stillman:

I think it's-

Ryan Horrigan:

No, I mean I-

Daniel Stillman:

We'll come back to you, Armando. 'Cause there's lots of [inaudible 00:29:31] there. But Ryan, what's on your mind?

Ryan Horrigan:

Well, I was going to say all of that is true in my experience too. I think that there's a human decision happening and real implications. So you have to take that seriously. You have to handle that eloquently and with compassion or empathy. But you also can't ignore a decision like that if it has to be made. You have to own it. You have to be the face of it. You have to stand up to it. You can't have someone else do it for you. It's yours. It's your thing to own. So I think as founders, we know that. It does get a little easier in that when you've had to do it a couple times, or if you've ever gone through a layoff situation, it sucks but you also have to learn how to get through it for your team. Because there are a lot of people who are still with you and you're doing it for a reason, to get better. So you have to focus on that.

But I would say to Armando's point, taking care of your health and your mental health is really important as a founder. And I think there's been times when myself and Armando have both found ourselves not doing that, and we try to be a little bit more aware of that today. Like I would say I'm getting older. I'm not that old, but I'm getting older. But I would say my health has never been probably poorer than the last few years of being a founder. And I do think a lot of that is just the stress manifesting as things like back pain or trouble sleeping or just stuff like that. And then just trying to make the time to work out more or be more intentional about how you eat. I think those things start to matter more when your body is reacting to say this mental stress that being a founder brings with it.

Armando Kirwin:

Yeah. I think Ryan hit on a big one for me that I forgot to mention, which is the team. So when you're in the process of doing this, when you know you're going this way and everyone knows that say this person doesn't fit the new model, there's cognitive dissonance with every day that they're still there. Even if everyone loves that person and that person loves everyone... I'm not talking about that. I'm just talking about... You know what I mean? So-

Daniel Stillman:

Yeah.

Armando Kirwin:

...when you do it, you actually help the team too though. So it's almost the hit you have to take as a founder, but your team will thank you because they have that extra clarity and they don't have the cognitive dissonance now of, "Well, what's that person doing if we're all over here doing this?" So-

Daniel Stillman:

Right, people know that. It's not like nobody's aware of this.

Armando Kirwin:

...that context is good. Everyone knows. They're all smart, they're all... So pretending that they're not is just such a waste of time. So getting really head on is great because even the person you're letting go also knows what's happening. So you can't just beat around the bush or pretend it's about this or something else, it's best to just do it. But yeah, thinking about the team helps, thinking about that boost helps a lot.

Ryan Horrigan:

Can I say one thing that-

Daniel Stillman:

Of course.

Ryan Horrigan:

...was a quote from, I think it's from a few years ago, at a TechCrunch Disrupt. I just saw it on YouTube. I think it was Dick Costello when he was at Twitter. And he was talking about team building culture and making tough decisions and dealing with tough things like these things. And he said something that really resonated with me. It sounds cold, but if you think about it makes sense from a founder point of view. He said, "As a founder, you have to care deeply about your people, but at the same time you can't care about what they think of you." And I thought that was really interesting. And his point there, what I think he was trying to say was, you actually do have to operate authentically in a way that shows empathy and caring. It has to be real because these are your people and this is your company. But when you make a tough decision, you can't worry about everyone's collective feelings. You have to make the decision that you as the leader believe needs to be made. And you can't get weighed down by what someone might think about that. You have to move forward. And that is the hard part, right?

Daniel Stillman:

Yes.

Ryan Horrigan:

But I thought that was really interesting.

Daniel Stillman:

It is. I'm so glad that there's these layers of conversation that we're talking about. The conversation that you're having with yourself. I think Armando, I appreciate you bringing up, and Ryan, you bringing up listening to your body. Because that's the base level, the signals that I am giving to myself. And also it's not, sometimes men don't often seek therapy. And so the idea that a founder needs a therapist and a coach is not something that people... You need a therapist and a coach. I think it's great to hear you've advocate for that. 'Cause I think there are very different types of conversations that you're having.

Ryan Horrigan:

Yeah.

Armando Kirwin:

Yeah.

Daniel Stillman:

How would you characterize what you get from one versus the other?

Armando Kirwin:

Well yeah, in therapy you're learning about yourself and hopefully recognizing certain patterns that you have. Not that they're easy to fix, but at least you know what's going on. But a lot of the coaching that I get, I think Ryan, we have the same coach. That's more about where we're trying to go. It's more about the future and how to get there and how to think about things. So one's about you in the moment and maybe why you're this way. And the other is a lot more future oriented. Like okay, what are the steps you should be taking over the next 12 months to achieve this goal? That's where the coaching is about increasing future outcomes, whatever they might be.

Ryan Horrigan:

Tactical stuff of how you want to deal with this problem or these players or people in this situation. And it's interesting that Armando and I have the same coach, but we see the coach separately, which I think is really interesting. And we never see this person together. And I really like that. I think it, for whatever reason, that really works. Because sometimes there's this connection that's made between this person and Armando and I that there's certain things that Armando and I can talk about together, but then there's probably certain things that are better discussed separately where this person can build a bridge or help us. So it's been really good, I think, for both of us. But then also just personally, regardless of how we relate to one another, just for each of us individually it's quite good.

Daniel Stillman:

Yeah, it's very interesting you mentioned that. 'Cause I think there's some people who think, "No, no, no, we should have different coaches so that we can have total silence," versus the benefit of them hearing the stories or the complexity of them hearing stories potentially about the other person.

Armando Kirwin:

Yeah, [inaudible 00:36:21] makes sense. Again, it's future oriented though. So it's about helping us achieve certain goals. I think the added context is what makes that coaching even more powerful.

Daniel Stillman:

Yeah. Yeah. That's awesome.

Armando Kirwin:

Yeah, if it was about our childhoods or something, then you could totally keep that stuff separate. Yeah.

Daniel Stillman:

Fair. So I think there's two more layers that I think that are important that I want to talk about. One is the cadence and format of how you two structure your own regular check-ins. Like how often you're having your own appointment with each other and how you structure that. And then there's another piece, if we think about the layers of conversation, we've talked about the pivot that you're having and this sensing that you're having with yourself and the conversations you're having. But we haven't talked about how you have the conversation with your funders, your investors as you go through that pivot. And I imagine that there's a level of complexity there.

So I'm hoping we can address both of those, are two very, very different questions. I probably shouldn't have introduced both, and that's bad hosting. But I'd love to talk about first how... You guys have your coaches, your coach. You got your emotional check-ins. How often are you two meeting and is there any specific structure you're using when you meet to make sure you're having the right conversations?

Ryan Horrigan:

I would say no, there's no specific structure and there's no specific time. And we talk once or twice a day, I would say, for 10 to 60 minutes. It really depends on what the conversation is.

Daniel Stillman:

That's interesting. So it's ad hoc?

Armando Kirwin:

It used to be a lot more. We used to call each other 20 times a day and it was craziness, but the company was smaller. In the last 15 months we've built a executive team for the first time. And so Ryan and I attend reoccurring meetings together, certain meetings with the team that operationally it's just easier for us, also for our team to not... Because the problem with telephone calls is no one else is there. No one else is learning and hearing and working through stuff. So it reached a point where it was actually harmful for us to have so many one-on-one conversations. It was driving our team crazy.

Daniel Stillman:

Yeah, because you're moving forward without your team.

Armando Kirwin:

Right.

Daniel Stillman:

Yeah.

Armando Kirwin:

Exactly. So we had to retrain ourselves in the last year or so. At this stage of the company, as you're approaching maybe 50 people or whatever, you have to retrain yourself to actually not have all these one-on-one conversations because they're black holes of information. So we do talk still a couple times a day, but we used to make all of decisions on phone calls and we had to stop. So depends on where you're at, I think, in your journey. And also remote wise and stuff like that where people can't pick up what we're talking about in the office or whatever.

Daniel Stillman:

Yeah.

Armando Kirwin:

Yeah.

Daniel Stillman:

That's a very interesting shift. Because obviously having, I've heard this from lots of early stage founders, a lot of conversation, just open dialogue, a lot of honesty and a lot of iteration. But you're at the point now where your senior leadership team needs to be part of the dialogue more frequently.

Ryan Horrigan:

Yeah. And I would say we've been really trying to work on right now in our company interdepartmental communication, because sometimes we find that different departments, let's say marketing and operations, and in our case, in a game company, art, engineering, product. There's all these different pods of people and they're all working towards this...

Daniel Stillman:

Uh oh.

Ryan Horrigan:

...goal, but-

Daniel Stillman:

Ryan warned us that his internet might do that.

Ryan Horrigan:

...sometimes they have different information, they have different strategies, agendas. Oh, sorry.

Daniel Stillman:

No, it's okay.

Ryan Horrigan:

Am I back?

Daniel Stillman:

We just had a tiny blip. You're back.

Ryan Horrigan:

Oh, okay.

Daniel Stillman:

So yeah, different strategies, different information.

Ryan Horrigan:

Yeah. So one thing we've been trying to do is create systems and processes that are simple and not too many of them that will bog us down to better disseminate information in an a sync manner, through a wiki, through Slack, through calendar invites. So we recently, and it's probably too late that we did this, we incorporated a process for agendas or meeting notes that gets shared through the whole company, except for sensitive ones like an HR meeting or something.

So let's say you're in engineering, you will have a multitude of ways to find out what happened in marketing this week, if you are so intrigued or if it matters to you. But then also getting departments to write weekly recaps and then larger monthly recaps and do some show and tell, sharing stuff during our all hands that's more about educating people on the great work they're doing.

Because one thing I think every company eventually finds out is you end up in meetings where people just go through status updates or slides, and that's terrible. If you have someone just reading to you what's on a slide that you should have read before the meeting started, that's just a waste of everyone's time. So what we've found is we need to get people actually having a discourse and having healthy debates or disagreements and also showing people how things work that they've built or that they're doing. So we're just getting more intentional with all that stuff. And it's taken us a while. But it's that thing where you don't want to do too many things, you don't have too many systems, too many processes. 'Cause then you get bogged down, right?

Daniel Stillman:

Yeah. You don't want to over structure, certainly not the size you're at.

Armando Kirwin:

Yeah. And it's remarkably hard. You'd think, oh, there's so many startups, there's so many companies in the world or teams, this stuff has all been figured out. No, it's so hard. It's really remarkably hard to get 50 people to always have the same information as each other at the same time and be running in the same direction. You do all of these things, and then you still end up having to... It's very clear. It's like, oh, I'm probably two months ahead of certain people on the company right now in terms of what we're thinking about, whatever. It never really ends. So that part's also just part of the learning, I think, of hitting the stage that we're at. It's you can maintain a real time sync when it's two people and they're talking to each other [inaudible 00:43:04]-

Daniel Stillman:

Yeah.

Armando Kirwin:

...times a day.

Ryan Horrigan:

Well another thing that we often talk about is in a company like a startup, you go from a small group of people, let's say less than 10 or five, where you're doing stuff and you're managing people who are doing stuff. That's the first phase. The next phase is you're doing stuff still and you're managing managers, I guess. And then at some point you really shouldn't be doing stuff. And I mean stuff like building stuff, you should just be... Or as a CEO, you got to do the fundraising, you got in charge of communication and culture and alignment. Which maybe for us is expressed through OKRs, right?

Daniel Stillman:

Yes.

Ryan Horrigan:

But if you find yourself making too many granular decisions, then you're probably doing something wrong and you're probably micromanaging people. So we've really tried to over the last year say to ourselves, "Hey, how many decisions are we a part of?" And sometimes, myself included, Armando knows, we'll make mistakes and we'll get too granular on something. For example, why is this red and not blue? But then the minute you do it, you know you shouldn't be doing it. That's someone else's decision to own.

Daniel Stillman:

Like, d'oh. I do care, but I shouldn't be making this decision.

Ryan Horrigan:

Yeah.

Daniel Stillman:

What a fascinating metric as a startup founder, number of decisions you are not touching but making and being a part of, it should drop.

Ryan Horrigan:

Right.

Daniel Stillman:

That's so interesting.

Ryan Horrigan:

Yes.

Armando Kirwin:

Yeah, it should drop. If you're hiring the right people, it should drop.

Daniel Stillman:

So we're getting close to the end of our time, which is shocking because we really hit a great vein, and I'm really... This is wonderful stuff. Is there anything that we have not talked about that we should talk about with the few minutes we have?

Armando Kirwin:

Well, do you want to talk about how you communicate pivots to investors, Ryan?

Ryan Horrigan:

Yeah. Look, I think it's not a secret that many, many startups, if not maybe more than people realize, do go through pivots. I actually think even companies who set out to build a particular product and end up succeeding have probably done a version of a pivot in terms of a product feature or who the customer is or their strategy of is it bottoms up? Is it top down? So I think there's different types of pivots. There's the real hard pivot. For lack of better examples, just the one in my brain, Slack was a gaming company that became a chat app. That's a pretty hard pivot, right?

Daniel Stillman:

Fair.

Ryan Horrigan:

And I think there was probably somewhere along the way, but they would probably tell you it wasn't a day that they decided. They had built this product for themselves, I think this is the story. And then they started using it, and then they were like, "Okay, we're going to actually just... this is the product." It's no longer a gaming company. Then there's like, "We were doing X and now we're doing Y," and it's a completely different industry. Those are super hard pivots. Then there's companies like us where it's like, "Oh, you were doing this thing and this other thing, and then you got rid of one of them." But you kept doing the same thing. You basically were doing two things and then you said, "Okay, it's just one thing now."

And then there's like the thing we just talked about where it's like, "Oh, I just changed my go-to market strategy and I'm going bottoms up instead of top down." But they're all versions of pivots. So I think when you go to an investor, A, you got to explain that succinctly and you got to prove that you have the right data points from the customer or the right people. But I think everyone's generally open to the idea if they feel you've assessed it intelligently with the right point of view or lens, with the right resources.

So yeah, we've never had an issue with that. I mean, I think if we were pivoting six times every year, that'd be a huge problem. But I think going from AI to bringing games into social media when that was already with us foundationally, for us that's worked out. But also building stuff in the gaming space is very hard and takes many years. It's a lot different than building a widget for Google Chrome that's going to do cool calendar stuff. Not to disparage that stuff, because those are huge businesses, by the way. But just gaming is a different level of complexity. And there are businesses that are way more complex, like in biotech or defense or something, right?

Daniel Stillman:

Yes.

Ryan Horrigan:

So-

Daniel Stillman:

It's quite a spectrum.

Ryan Horrigan:

...it's all relative. Yeah, yeah. So-

Daniel Stillman:

So one thing I'm hearing is you get one or two pivots.

Ryan Horrigan:

Yeah, that's it.

Daniel Stillman:

You can explain it with the narrative core, especially as you said, with the right data, saying, "Look, we've done our homework and our thesis we now know needs to be revised." Nobody's going to say, "No, stay where you're at." If they've bought into your vision, they may buy into your new narrative if you're sticking with the narrative core. So that's really helpful.

Armando Kirwin:

Especially investors. Investors theoretically are going to be like, "Yeah, that makes sense. I support you." I think the team can be a little harder, especially if someone's been working on... someone who's actually building whatever it was that you're not using anymore. Or even, "Oh shit. Well, this..." I don't know if I'm supposed to say that, but anyway-

Daniel Stillman:

You can curse as much as you want, it's all good.

Armando Kirwin:

...Oh darn, now you're going to lay off my friend. You're going to lay off my friend. So anyway, I think you get more feet dragging for sure on the team side, and that is obviously probably the most important relationship. So that you have to really manage in a more nuance way over a longer period of time.

Ryan Horrigan:

Or you get a fracture where half the people are gung-ho, and they're like, "Yeah, we see it too, and you're right." And then the other people are like, "No wait, why are you... What about this thing that we spent all this time on?"

Daniel Stillman:

How do you heal a fracture like that, when there are camps, factions?

Ryan Horrigan:

I don't think there's a perfect answer for that. I would say sometimes you're trying to bring people to the middle, but that's not always the case. Sometimes you're very firm like, "No, this is the direction." So it really just depends.

Daniel Stillman:

That's really interesting.

Armando Kirwin:

Yeah. And also your team composition, you'll have people on different sides of lots of debates. And as long as you can get them working together, even temporarily, it still makes sense. I'm sorry, it's torrentially down pouring so my [inaudible 00:49:27] is terrible now-

Daniel Stillman:

Actually, I can't hear... Zoom is really good at pulling away repetitive... So I can't hear it at all, you're amazing. It's all good. Yeah, sorry Ryan, go for it.

Ryan Horrigan:

One more just on that topic, something else I heard someone say, and I wish I could remember who recently. Someone who's sort of a operations guru, they said you ideally aren't looking for consensus, because consensus weighs you down. You're looking for consent.

Daniel Stillman:

Yeah.

Ryan Horrigan:

I really like that. You don't want a company where the CEO decides everything, that's not going to be good for anyone or for culture. And you might move quickly, but you're not going to get the best ideas. You're going to have bad ideas because it's going to be one person's idea. But then if you go for consensus, it's going to take forever and you're also going to revert to some sort of mean or middle ground that's not amazing.

But consent, like the way it was laid out to me, and there's a process for it. There's a high bar to actually challenge an idea when a group of people or whoever's putting this idea forward is put it out there. Let's say it's status quo or we're proposing something new. You want to make sure that you can identify when there's a dissenting opinion for a different strategy, that that opinion is pure from a business standpoint and it's not emotional or from a ego standpoint. And there's some ways to suss that out in a process that I read recently. I thought it was really interesting and just like, yeah, just get to consent not consensus.

Daniel Stillman:

If you have that link, if you dig it up, I'd love to see that.

Ryan Horrigan:

I'll share it with you, yeah.

Daniel Stillman:

And this really sounds like the disagree and commit mindset. Like we may disagree, but we need to get some data to learn and so let's get consent to at least try.

Gentlemen, this has been a wonderful, vital, vibrant conversation, but our time together is almost done. Where should people go to learn more about all things Ryan, Armando, and of course Artie. Where shall we direct people to the internet if they want to connect more to you two and the thing you're making together?

Armando Kirwin:

Just artie.com, A-R-T-I-E.com. You can keep up with us there. And our platform is already functional, so our first game is live on our platform so check it out. It's in alpha stage, so I'd love to have people playing the game and helping us improve it. And we have a second game that we're starting to work on as well. So lots of fun stuff. But yeah, I think that's probably the best way.

Daniel Stillman:

Awesome. Anything to add to that, Ryan?

Ryan Horrigan:

No, that's it. I mean, if you want to work at Artie, we're on LinkedIn too.

Daniel Stillman:

Excellent. Well, gentlemen, this has been a deep and nourishing conversation, so I will thank you for your time and call scene.

Ryan Horrigan:

Thank you.

Armando Kirwin:

Thank you so much.

Daniel Stillman:

All right.

The Power of Intention

I am excited to share my conversation with Leah Smart, who I had the pleasure of meeting at the Culture Summit where we were both giving main stage talks. Leah is brilliant! She’s all about helping people become the authors of their lives, which she does through her work on the LinkedIn Editorial team and hosting her LinkedIn podcast, In the Arena with Leah Smart, which is out every week wherever you find your podcasts.

She loves facilitating human development work for leadership teams through coaching and workshops and sharing science-backed actionable concepts and strategies to transform your life, your work, and your relationship to everyone around you.

Today we talk about how she approaches designing her conversations with guests as a dance, how she molds her conversations with herself through personal mantras, and her perspectives on the power of intention.

Links, Quotes, Notes and Resources

https://www.leahsmart.co/

Minute 2

Leah Smart:

I used to think that when I went into an interview, I had to show the person on the other side, that I was just as smart or close in knowledge, because I wanted to show them, "I'm your equal," in a way. What was really behind that, it for me probably, created more anxiety.

What was really behind that was, I have done a lot of work, and though I speak to so many people, who have gone the traditional educational route, I have a lot of experience and I read a lot and I learn a lot and what's funny is, it's like the more you know, the more you actually want to feel comfortable knowing very little and being more curious and a close friend of mine, who used to dance for the Royal Ballet of Denmark said to me, I was freaking out this one day, earlier last year, I was speaking to Deepak Chopra and he was my first in-person interview.

I was going to lose it. I call my friend Shelby, and I was like, "I don't even know, I'm so nervous. I can't even..." I was in my apartment waiting to go downtown to the office, to do this interview and she just said to me, "I used to dance." She used to dance for years and she said, "The thing I told myself, my mantra was, nothing to prove, only to share," and I've used that actually every time I've been in a situation, where I've felt my own performance anxiety jumping up. I'd say that's one, is realizing I do have expertise, but I'm not here to prove it to you.

I'm here to share with the other person in a conversation. I'm here to look at them as simply a human being, because that's all they are.

Minute 16

Leah Smart:

No matter where you sit on the socioeconomic spectrum, you are likely to experience some level of pain and/or suffering. I believe that we have put so much emphasis on what we have and what we succeed at and what we achieve at and I am totally guilty of this. I have dreams and goals and things I want to create and I think, "Gosh, all of us should have that, because it keeps you going," but what is missing, or I should say what we're doing, is putting all of our stock and investment in these external things. What do I have? How many people know me? What does my social following look like?

Do I look the right size today? Or is my hair okay today? How do people accept me? It's all these things, that are superficial that we all do it. We all fall victim to it. The challenge, is when you don't have anything to go back to, to re-tether you to what's real and to me, what is real, is not all of these things that have been created around us to keep us going, like little hamsters on a wheel.

It's the internal, it's the stuff in your inner world, where you want to invest and take stock and slow down and get connected and recognize how meaningful and small life is, right? It's the recognition that there is so much more beyond what you're experiencing now and that you are a small part of a huge world, but that your life is very meaningful and that you are so much more than the things that you are valued for, when you walk outside of your house or not valued for.

Minute 33

Leah Smart:

When we have a desire, the immediate thing to do, is to look at all the ways in which it's not happening and we're going, "I have a desire, and here are all the ways I lack. Here are all the ways, in which it's not going down." How do you feel when you have a desire and then you spend the next couple of days telling yourself how shitty it is, that you don't have it yet?

You feel pretty bad, and then you expect that thing to happen. If you just think about it logically, it's like, "I want a new job. I hate my job so much. I hate it. I hate it. I hate it. I hate it. I hate it. I hate it. I hate it," and then you think that your dream job's just going to show up and you're going to be happy? I haven't had that experience. The time that I hated my job, I went into another job, another company, that I also didn't love.

It wasn't like life turned around from that place. It's similar to, do you want to suffer on the way? And also, is the outcome of what you are trying to create, potentially is there an upside by not suffering along the way? For me to feel, is to feel the experience of what it will be like when, not from a place of lack, but from a place of familiarizing yourself, your brain, your body, to the experience of what it's going to be like when.

Minute 36

Leah Smart:

To truly experience something, can also show you that it's already yours. I'm 35, and a lot of women that I know and who are in my life, are are wanting partners and when you want a partner, what do you do?

You go, "I don't have one." You look at all the couples around. It's like there's couples everywhere. You're like, "I cannot walk a step, without seeing people who love each other," and you can either choose to get really pissed off and feel like you're never going to get it, or you can choose a little bit differently and what I realized was at the time when I was wanting partnership, if I could just sit in the feeling of love, I could realize that actually it was already mine.

Nobody was going to create that for me. It's actually just that there's someone I can point it toward, and that meant that I could feel it, without another person sitting in front of me. Because guess what? That person's going to come and they're going to piss you off sometimes and they're going to make you happy sometimes. They're going to... It's just the same. It's like, you have so much more autonomy and power when you can recognize what is inside of you and not that someone else is going to make it possible for you. It's just, they're presenting an opportunity for you to bring out what you already have.

AI Summary

Leah and Daniel discussed Leah's approach to interviews and the importance of being real in conversations. They also talked about the importance of investing in one's inner world, setting intentions before conversations, and creating what one desires through intentional action.

Meeting summary:

(3:56) - Leah discussed her recent interview with Rainn Wilson and her interest in exploring spirituality and ancient wisdoms in her work

(21:17) - Leah discusses LinkedIn's values and how they prioritize being a good person, doing the right thing, and acting like an owner

(24:46) - Leah emphasizes the importance of investing in one's inner world and recognizing the meaningfulness of life beyond external validation

(27:30) - Leah discusses the tension between accepting the current situation and driving towards what we want to create, and suggests focusing on changing our orientation to the gap between where we are and where we want to be to find contentment and calm along the way.

(30:41) - They talk about the importance of grounding oneself in spirituality or something greater, and how going inward can lead to being a better person when interacting with others

(35:54) - They discuss the need for human connection and meaningful conversations, and how everyone needs each other to function.

(45:30) - Daniel talks about the importance of being intentional in creating what one desires, rather than just running away from what they don't want

(46:52) - Leah discusses the importance of sitting with what one wants and becoming clear and intentional in their life, including routines and rituals that bring richness and ease

More About Leah

I'm on the LinkedIn Editorial team exploring the stories and ideas that increase clarity in our lives so we can work and live in a better world. My podcast, In the Arena with Leah Smart, is out every week wherever you find your podcasts. I'm also a keynote speaker for companies and events sharing science-backed actionable concepts and strategies to transform your life, your work, and your relationship to everyone around you.

With over 10 years of experience in learning, consulting, and coaching, I am passionate about human development and potential.

Previously, I was a Principal Learning Partner at LinkedIn, where I consulted, built, designed, and facilitated human development work for leadership teams through coaching and workshops.

Full Transcript

Daniel Stillman:

Oh, well now see, we'll just keep the messy intro.

Leah Smart:

Let's keep it.

Daniel Stillman:

Yeah. I officially welcome you to The Conversation Factory. I've been thinking about where to begin this conversation. Just generally speaking, what would you say are your favorite kinds of conversations?

Leah Smart:

I find that of all the interviews I've done, my favorite ones are the ones where I'm learning something or looking at something differently, where I get to be curious, where it feels more like a dance than a Q&A, where it's like you're just vibing and flowing and the outcome's going to be the outcome, but that the experience for the two people or however many people are in the conversation and then those who are listening and/or missing, because they're listening to a show weeks later or a month later, feel like they got to tune in to two friends. I was saying this yesterday, I got to speak with Rainn Wilson and afterward looking back, I was like, I really hope it felt like you got to peer into the window of two friends hanging out in a house, talking about something that you got to join in on and I want it to feel friendly, casual, but also interesting, respectful, relational, relatable, while also giving people space to learn something new and approach life differently.

Daniel Stillman:

Yeah. How do you think you do that, because you are a great interviewer. I've listened to some of your interviews. What are you bringing into that room? How do you feel like you're doing that?

Leah Smart:

Well, I think it starts with realizing what you're an expert in and what you are not an expert in and what you expect of yourself and what you shouldn't expect of yourself. I used to think that when I went into an interview, I had to show the person on the other side, that I was just as smart or close in knowledge, because I wanted to show them, "I'm your equal," in a way. What was really behind that, it for me probably, created more anxiety.

What was really behind that was, I have done a lot of work, and though I speak to so many people, who have gone the traditional educational route, I have a lot of experience and I read a lot and I learn a lot and what's funny is, it's like the more you know, the more you actually want to feel comfortable knowing very little and being more curious and a close friend of mine, who used to dance for the Royal Ballet of Denmark said to me, I was freaking out this one day, earlier last year, I was speaking to Deepak Chopra and he was my first in-person interview.

I was going to lose it. I call my friend Shelby, and I was like, "I don't even know, I'm so nervous. I can't even..." I was in my apartment waiting to go downtown to the office, to do this interview and she just said to me, "I used to dance." She used to dance for years and she said, "The thing I told myself, my mantra was, nothing to prove, only to share," and I've used that actually every time I've been in a situation, where I've felt my own performance anxiety jumping up. I'd say that's one, is realizing I do have expertise, but I'm not here to prove it to you.

I'm here to share with the other person in a conversation. I'm here to look at them as simply a human being, because that's all they are. We're not all that different and then finally, before I go into an interview, what I love to do, and it's not always easy, but is to take just two or three minutes to just sit quietly, whether that's just focusing on my breath or just sitting, setting intention. It allows me to just turn off my mind and then I can be fully present versus worrying about what I'm supposed to be asking next and how it's going to look, how it's going to sound, it's like you've got to be fully there.

Daniel Stillman:

Yeah. Do you feel like you come back to that, for lack of a better word, a mantra, that nothing to prove? Are you bringing that in as internal self-talk? Does it come up during the conversation, where you're just, "Serenity now," was always my classic internal mantra. It's like nothing to prove. Do you sometimes remind yourself of that, during the conversation?

Leah Smart:

Yeah. Yeah. Yesterday, and I don't know if the mantra specifically, the nothing to prove, only to share, specifically came up during the conversation, but really, that mantra is let go of performance anxiety. Let go of the fear you have of what people are supposed think of you and just show the hell up. Yesterday I was like, "All right, I'm sitting here. It's a live interview. There are 1,000 people watching. Just show up. That's it." Yeah.

Daniel Stillman:

I love that you use the term dance and this is interesting, because for me, I think about conversations 100% as a dance, but dance can either be totally unstructured, there's just fluid dance, but even then you're dancing to the music, you're responding to the music. What do you feel like are your moves, when you're dancing in these conversations?

Leah Smart:

I like that question. I go into most conversations, realizing that the people I've talked to, have done a million conversations like this before. They've had people who have moves that feel very structured, that feel like, "And then I will ask you this question next," and, "To follow this up," that have a harder time being in the moment or when I was becoming a coach, it was called dancing in the moment and that's what I mean. My dance moves are probably, they're not spontaneous, but in listening to this book and reading this book, Soul Boom by Rainn Wilson, he shared, and I've heard Oprah share this before, one of her favorite quotes and Marion Williamson also is, "God, use me. Use me. Have me go where you want me to go, do what you want me to do, say what you want me to say and be what you want me to be, all for the purpose of the highest good."

I honestly believe when I'm in an interview, I am truly in what Mihaly Csikszentmihalyi, one of the positive psychology researchers early on, I'm in flow. It means that I am so there, that my dance moves are just about whatever's there. Something is clicking in my mind that's saying, "Grab that word, grab that phrase. This reminds me of this." It's like everything's firing, to the point where yesterday I had two interviews, but this big one I had, I got home and I had to just lay down. I went to sleep for three hours.

Daniel Stillman:

You left it all on the stage.

Leah Smart:

I leave it on the stage and how else are we supposed to live? If I can't amplify this person's incredible message, by putting everything on the dance floor and being so damned present, then I'm not really doing the kind of job I want to do, for this person's message. Now do you do that all the time? No. Sometimes my dance looks like, I'll go in and tell my producers, "This is a light conversation. I'm going to let it be fun and light and let's just see where it goes," or I'll go in and I'll say, "This is a short conversation. Let's see what that looks like," and I think my dance moves change, based on where I'm at, based on the person's message. It's like, "Read the room."

Daniel Stillman:

That seems like a good poster for us all to have, "Read the room, Daniel."

Leah Smart:

Read the room.

Daniel Stillman:

Well, something I'm sitting with is, your whole life is not doing the interview, right? Because, you also work as a one-on-one coach. All the conversations that happen, with all of the people you collaborate, to make all of these conversations happen and I wonder, the dance of those conversations and the mantras of those conversations, how you feel you are looking at those conversations and designing them, either differently or maybe exactly the same as you do.

Leah Smart:

The first thing that just came up for me is, what's needed now? I am not always designing conversations perfectly and sometimes what shows up, is the shit I'm bringing with me. Last week I had a bike accident, so I was not in a good mood. I was hurt. I'm okay. I lived. I have some...

Daniel Stillman:

How's the bike?

Leah Smart:

Bikes in great shape.

Daniel Stillman:

That's good.

Leah Smart:

Held up fine and there was no car involved and all that, but I wasn't in a good mood last week, and that's hard for me to really accept, when I'm not in a great mood and maybe I'm not being my best self with other people, but that was the reality. I think it's less of planning every conversation and more of, how am I showing up in this conversation? What am I potentially likely to have to apologize for later? Or what am I bringing right now? It's a great day. I'm happy. I'm in a great mood. Things are good, that's great. If it's not a great day, I'm not happy, I'm not in a great mood, I tone things down a little bit. Maybe that means we're a little more focused. Maybe that means we shorten the conversation. I think it's just knowing what's needed now.

Daniel Stillman:

Yeah. The phrase I sometimes think about is, is serving the conversation? And it seems like that's really what you're... You're serving the person in front of you in their message, sometimes and sometimes you're serving the conversation as a whole and you're in the conversation too, which means if your energy is what it is, you have to serve you. You have serve yourself as well and take care of yourself. That seems like all those things.

Leah Smart:

Yeah, I think we all do.

Daniel Stillman:

Yes.

Leah Smart:

Yeah. It's all of that and for you and I, we're not journalists. We don't go into conversations simply, not simply, but just to collect a story, collect the data, and then report out the story. We bring ourselves in a different way than many trained journalists. Most trained journalists are not taught to bring all of themselves and their opinions. That's the whole point of journalism in general, or at least it used, was that we get the objective story, unless it's an opinion and an op-ed. Yeah and I'd say, of course journalists are people too, so they're bringing their stuff too, but for us, it's a little more complex, because we want to bring our stuff and we're walking in saying, "I'm showing up with my stuff and how do I still serve, based on that?"

Daniel Stillman:

Yeah. I want to transition. I have an image here. It's actually a terrible drawing I did, of your wonderful talk from the Culture summit and.

Leah Smart:

Oh, I love...

Daniel Stillman:

The reason I was looking at this, when you were talking about needing something, our pre-chat about we need more, we need something in this modern era, there's this little sketch, something you said during your talk as the organization, as a church, a place for creating meaning and we do spend a lot of time at work and your work is at LinkedIn, which is a church for work, for sure and I'm wondering what you feel like, church has evolved a lot, what we need as people, is ever evolving. What do you think our work church should be like?

Leah Smart:

I feel really fortunate. I've worked at LinkedIn since 2010. I left for a year and a half. I came back, because that work, church quote, was the most intentional I'd ever had and I haven't worked at a lot of different places, but our values at LinkedIn have stayed the same. Yeah, light shifts and things like this, but generally, it's about being a good person. It's about doing the right thing. It's about acting like an owner. I remember when I first started out, there were only 400 employees. There are over 20,000 at LinkedIn now.

Daniel Stillman:

Wow.

Leah Smart:

Act like an owner was, pretend that you started this company and you're running it, what would you do?

Daniel Stillman:

Yeah.

Leah Smart:

Humor was a big one and still is, being open, honest and constructive and I think we've changed it since then. I can't remember what it is now, but it's all things that, if you raised a kid and told the kid, from the time they could speak and show them from the time they could watch you interact with the world, the values LinkedIn has, they'd lead a pretty good life.

That to me, told me all I needed to know, because not only was it something that LinkedIn said, it was something that I saw done. Now, do we all make mistakes? Of course. Are you going to hire only people who do that perfectly? Of course not, but to me, I'd say if I were picking a company today, and I think a lot of GenZers and millennials are picking their companies based on the company's values and their beliefs around social issues, around climate, around things that are happening in the world and how they're interacting with those things.

Daniel Stillman:

Yeah.

Leah Smart:

You have to act like you care and it's not just that you wrote it down or you gave a little bit of money here or there. It's like, you have to act like you care and I will say as a caveat too, I'll say, I don't know that workplaces should be our new churches. I do know, that church attendance is down. I know that people who ascribe to a religion has massively decreased and continues to decrease.

As I was saying that, I was illustrating that people put more trust in companies than they ever have before, in corporations and expect so much more out of CEOs and C-level executives, when it comes to social issues, that used to be the issues we'd talk about at home and then we'd walk over to work and we'd sit and do our job from nine to five and clock out and what I'm highlighting, is that there has been this in the last [inaudible 00:15:26]. That means that there's got to be something more given by workplaces, which many of them have, but also, I think that for us to put our faith into just that, another governing body, that also is associated with our paychecks, isn't necessarily the only way and it may not be the best way.

Daniel Stillman:

Yeah. I guess what are the other options, right? Because, you're talking about, we need more of something in the world, in our own lives. What do you want to bring more of into your conversation, broadly?

Leah Smart:

I think and listen, I'm just a normal person like you and everybody else, but when I turn on the news, when I walk around in the world, and I live in New York City and so do you, I think there's so much good, and I think there's a lot of suffering and a lot of struggling.

Daniel Stillman:

Yeah.

Leah Smart:

No matter where you sit on the socioeconomic spectrum, you are likely to experience some level of pain and/or suffering. I believe that we have put so much emphasis on what we have and what we succeed at and what we achieve at and I am totally guilty of this. I have dreams and goals and things I want to create and I think, "Gosh, all of us should have that, because it keeps you going," but what is missing, or I should say what we're doing, is putting all of our stock and investment in these external things. What do I have? How many people know me? What does my social following look like?

Do I look the right size today? Or is my hair okay today? How do people accept me? It's all these things, that are superficial that we all do it. We all fall victim to it. The challenge, is when you don't have anything to go back to, to re-tether you to what's real and to me, what is real, is not all of these things that have been created around us to keep us going, like little hamsters on a wheel.

It's the internal, it's the stuff in your inner world, where you want to invest and take stock and slow down and get connected and recognize how meaningful and small life is, right? It's the recognition that there is so much more beyond what you're experiencing now and that you are a small part of a huge world, but that your life is very meaningful and that you are so much more than the things that you are valued for, when you walk outside of your house or not valued for. Yeah.

Daniel Stillman:

Yeah. Yeah. This comes back to, I think I can connect this to this idea of, you talked about self-awareness and optimism, as two things we wanted to touch on and it seems like being grounded and tethered to who you really are and what you really want, is really important and powerful and I think there's a fundamental tension between what is and what we want to create, accepting the current situation and driving towards what we want to create. How do you think about balancing that out, when you think about the things we need to feed ourselves, to sustain ourselves?

Leah Smart:

I think there's always got to be tension between what's happening and what you want to see happening. I call that, when I'm working with someone and I'm coaching them or working with a team or whatever, we talk about different areas of this thing called the Wheel of Life. It's an eight sectioned wheel, that has all of the areas of life that we all concern ourselves with, career, romance, family and friends, our fun and recreation, where we live, our health, our money and I have people, don't have to tell me, but tell themselves, how satisfied they are with each area of that wheel, on a scale of zero to 10 and then I ask them, "What would contentment or satisfaction look like for you, in each of those areas?" And what we generally find, is at least in one or two, sometimes more, a gap.

A space between where I am and where I want to be. I don't think that life would be interesting or meaningful or fertile ground for growth, if there weren't a gap between point A and point B. Now, what we all fall victim to, and what I hope to support people in doing, and what I do my best to shift, is not your relationship, to the lack inside the gap, but your relationship to the understanding that there will always be a gap and if you can focus on changing yourself and your orientation to that, then life will change around you, versus, "I need to change that thing. I make $50,000 a year today, I need to make $100,000 and I'll be happy."

Well, no. Yes, we should all have goals, but that can't be the answer to your contentment, or I shouldn't say can't. I should say, how much do you want to struggle on the way to your goals? How much suffering do you want? If you make $50,000 today, how can you find some level of appreciation, gratitude, and calm in that, knowing that you're moving towards something else, something bigger, something greater, so that you're not suffering, as you get to that goal, in the same way.

Daniel Stillman:

Yeah. It's interesting, because you talked about the change equation in your talk, God, it seems like... It was so long ago. It was almost a year ago. Dissatisfaction, times vision, times first steps, if that's greater than the resistance, change happens, but what I'm hearing you talk about now, is dissatisfaction can be a positive motivator, for our internal dialogue, but you also don't want people that you're working with and trying to help, you don't want them to be suffering through that dissatisfaction and that is very subtle. It's like we want them to feel the dissatisfaction, we also want them to feel the vision, what they want and find movement that is not self-abuse.

Leah Smart:

Yeah. I want them to see the hole, but not jump in it.

Daniel Stillman:

Yeah.

Leah Smart:

You know what I mean? There's the hole. That's my dissatisfaction.

Daniel Stillman:

Like you say, I want them to feel the hole, but not jump in it.

Leah Smart:

See the hole, but don't jump in the hole. We all have it. We're all going to have dissatisfaction. You could call dissatisfaction desire too. If you want to reframe it, fine. It can be such intense desire, that moves you. It can also be really intense satisfaction. We've all had that dissatisfaction. We've all had that moment where we're like, "I'm so damned sick of myself. I've got to fix this," but then we also have that moment, where we're like, "Oh my God, I want... I feel this thing," and then the vision is then, let me paint that, paint done for me, paint the picture of it.

Daniel Stillman:

Yes.

Leah Smart:

But yeah, when it comes to dissatisfaction, there's the hole. See it, know it's there, change your relationship to it by shifting... The fact that you can look at the hole, without having to bury yourself.

Daniel Stillman:

That's really interesting. To use your word, to stay grounded and tethered to...

Leah Smart:

Tethered.

Daniel Stillman:

And what is that thing, going back to the conversation you were having with Rainn and this work on spirituality, what is it that we stay grounded and tethered to? What do you think we want to have more of, you want us all to have more of?

Leah Smart:

To me it's, you can call it whatever you want, God, spirituality, the universe. For me and according to Rainn, it's also 31% of millennials and many more GenZers, file ourselves as the nuns, the people who when you say, "What religion are you affiliated with?" We say none.

Daniel Stillman:

Yeah.

Leah Smart:

I remember OkCupid, when I first started dating, it was like, "Spiritual, but not religious," and I was like, "That's me."

Daniel Stillman:

Yeah. Yeah.

Leah Smart:

No, for me, that means it's creating the space in my life, to connect to myself, to remember and connect to something greater and to be connected deeply and meaningfully to someone else too and I added that recently. When I first started on my own, just like, how do I figure out what spirituality means to me? Because I realized that, that was missing from my life, I just went on a solo thing. I was like, "I'm going inward. I'm meditating every day, trying to do it for long periods of time, for an hour, for whatever, and I'm journaling and I'm doing all this stuff."

And it was so enriching, but what you realize over time and what studies have shown, they just finished this Harvard study, it was a 75-year longitudinal study, to say, "What makes a good life?" It was meaningful relationships. It didn't matter how much money you made, it doesn't matter who you are, where you are, that's it. I add that in to say, "Now, I recognize, you can't just go inward and stay inward. The point of going inward, is to be a better person when you go outward and then continue to do the work.

Daniel Stillman:

Yes.

Leah Smart:

And yeah.

Daniel Stillman:

What's interesting about what you're saying, one of my past interviewees, Michael Burin described, he's a more of a conversation design nerd, than I ever could hope to be and I used to think of conversations as a spectrum of size, from little to big, and he put it as an onion and in the center, is the conversations we have with ourself and it's the core in some sense, it's what it's all grounded in.

If we don't invest in the core, we are hollow and we don't have anything to bring to those bigger conversations, talking to other people, community, but you're talking about a much bigger conversation, that's containing it all, which is a, "What's it all about? What do I think this means to me? How do I ground it in my own sense of what life means?" Is that fair to say? Because, I see you as very much taking care of that conversation with myself and grounding myself, but that larger conversation seems to be what you are really tethered to, that makes you feel like you're not just flung out into the universe. It's like you see it as something's being held.

Leah Smart:

Yeah. Yeah, it's for the sake of. Self-care has become commercialized, right? It's like, "Take a bath, have a glass of wine, have a me day, get rid of toxic people."

Daniel Stillman:

That is such a trend. Getting rid of toxic people, is very on trend.

Leah Smart:

Yeah, and that's a whole other can of worms, because it's like, if everybody's toxic, then you might want to look in the mirror. We all have our own work to do.

Daniel Stillman:

You heard it here first, everyone. You are the constant in all your relationships.

Leah Smart:

You sure are. It's the quote, "If a fight breaks out in every bar you go to, maybe it's you." That's a whole set for me of like, you've got to be so careful. Yes, there are people out there who are not the right match for you, who are not the right people, who maybe aren't doing their work. All of that, but yeah, I think the focus goes here and for me, when I can focus here, I can focus there. When I'm not focused here, this becomes so much harder and it is what fuels me.

Daniel Stillman:

And for those of you who don't know, Leah's a hand talker. This is an audio podcast.

Leah Smart:

I sure am. I'm not a conversation designer.

Daniel Stillman:

No, no. Your hands are... That's a very common way. She's making the small gesture and then the big gesture, right? You're holding them both. You want to be there with both of those conversations.

Leah Smart:

Yeah. Yeah, and every part of the human body, in order to function, needs each other. We all need each other. I just happen to be a person who is so driven by this and driven by having deep and real and meaningful conversations and sharing them and getting them out there. Somebody else, might know that there are so many other people out there, who never want to have these conversations. They don't know how to go there. They don't want to go there. Whatever it is, their lives are too bad. I don't care. They have another role to play in this body of humanity. That's my job. If that's what I'm here for, which I do believe it is, then I've got to do my best to help reveal those things, so that people can have access to the information that can help them feel tethered and tethered isn't always bad. It's something to return to.

Daniel Stillman:

Yeah. Tethered is great, when you're doing a space walk.

Leah Smart:

Mm-hmm. Correct.

Daniel Stillman:

Really, really want to be tethered and we are. Tethered is great, when you want to feel connected to something. Tethered and grounded, we're using them as broad synonyms for each other, which I think is really great.

Leah Smart:

Yeah.

Daniel Stillman:

I want to make sure we have some time for talking about, I'm a big fan of, and I have fundamental tensions with this, recipes. I think recipes are really powerful ways of learning, because they're how we... I usually look at two or three recipes before I cook anything and then I take one, and then I just make it my own, which is I think, a great step that everyone needs to get to become a Chef, of their own life. We're not talking about recipes for cooking, we're talking about recipes for conversations and you shared one with me, "Desire it, feel it, experience it, create it," which seems like a very nice recipe, a very handy recipe, to whip up a journey of self-discovery. Is that fair to say?

Leah Smart:

Yeah. Well, in the kitchen, I am a follow the recipe to the tee, freak out if there's any more or any less of the thing.

Daniel Stillman:

You don't tap into your ancestors for the...

Leah Smart:

No ancestors have any information I am taking. Print out the recipe, are you sure that was a teaspoon? Yeah, don't mess with...

Daniel Stillman:

Well, first of all, this has nothing to do with what we're talking about, but I was saying this to my wife the other day. I was like, "There needs to be something better than... Teaspoon and Tablespoon, just sound so similar. They should have totally different names or it should be all metric.

Leah Smart:

Correct. Big spoon, little spoon would even work for me.

Daniel Stillman:

Big spoon, little spoon. Yeah. It's just totally dumb and I am a very, very well accomplished baker and each time I'm like, is there a TBL? Is that a TSP?

Leah Smart:

Yeah. Correct. TSP, yeah. What are we doing here?

Daniel Stillman:

It's way too much cognitive load. That being said, am I right about, because we haven't talked about this desire it, feel it, experience it, create it. Is that a recipe that you use, to map out a journey from where I am now, to where I want to be?

Leah Smart:

Yes. Yes. I think, like you said before, the natural tension between being in one place and wanting something different, is going to be the way of our lives. We will never be at a 10 in every area on the wheel of life and perfectly satisfied and nothing could change. That's life and I'm still learning that. It's like we're all still learning that. I hope some of us maybe believe that that's not the case, but on this idea of, we are all here, we do, I believe all have free will. We do have agency over how we experience our life.

I also think and believe and through experience and I'm like, "Experience is the best teacher," I've got evidence through experience, that when I get really clear and connected, that I have a desire. That desire has been for me, not like, "I want a green car." It's like, "This is what I want to be doing for work," or, "This is where I want to be living," or, "This is who I want to be partnered with." I have used those desires, to go inward and to really get clear on what that means for me. What's that feel like, to have that thing? And I don't want to get all woo-woo, but I'm going to a little bit, and now...

Daniel Stillman:

You can get woo-ish.

Leah Smart:

Great. Let's get woo-ish. I love that. When we have a desire, the immediate thing to do, is to look at all the ways in which it's not happening and we're going, "I have a desire, and here are all the ways I lack. Here are all the ways, in which it's not going down." How do you feel when you have a desire and then you spend the next couple of days telling yourself how shitty it is, that you don't have it yet?

You feel pretty bad, and then you expect that thing to happen. If you just think about it logically, it's like, "I want a new job. I hate my job so much. I hate it. I hate it. I hate it. I hate it. I hate it. I hate it. I hate it," and then you think that your dream job's just going to show up and you're going to be happy? I haven't had that experience. The time that I hated my job, I went into another job, another company, that I also didn't love.

It wasn't like life turned around from that place. It's similar to, do you want to suffer on the way? And also, is the outcome of what you are trying to create, potentially is there an upside by not suffering along the way? For me to feel, is to feel the experience of what it will be like when, not from a place of lack, but from a place of familiarizing yourself, your brain, your body, to the experience of what it's going to be like when. I have found that doing that, is what creates the experience.

Daniel Stillman:

Yeah.

Leah Smart:

I've truly focused on it three times, in three very clear ways, and I couldn't have told you how it was going to happen. I didn't know, but the fact that I was able to desire it, to feel it, to sit with the experience of it, to really sit with it and to believe in it, because sometimes we sit with it. It's doing your daily affirmations, it's like, "I am this." You don't believe it half the time. That's why I'm not necessarily a believer in only doing affirmations. I think they're great, but they only go so deep. To truly experience something, can also show you that it's already yours. I'm 35, and a lot of women that I know and who are in my life, are are wanting partners and when you want a partner, what do you do?

You go, "I don't have one." You look at all the couples around. It's like there's couples everywhere. You're like, "I cannot walk a step, without seeing people who love each other," and you can either choose to get really pissed off and feel like you're never going to get it, or you can choose a little bit differently and what I realized was at the time when I was wanting partnership, if I could just sit in the feeling of love, I could realize that actually it was already mine.

Nobody was going to create that for me. It's actually just that there's someone I can point it toward, and that meant that I could feel it, without another person sitting in front of me. Because guess what? That person's going to come and they're going to piss you off sometimes and they're going to make you happy sometimes. They're going to... It's just the same. It's like, you have so much more autonomy and power when you can recognize what is inside of you and not that someone else is going to make it possible for you. It's just, they're presenting an opportunity for you to bring out what you already have.

Daniel Stillman:

Yeah. Yeah. What's interesting about this to me, is I still have the change equation up on my screen and with the analogy of dating, it's a good one, but if we bring it back to the other one you talked about, which is your job, if you're just always running away from, "I hate this job," and you just keep running away and you just say, "Well, not this job," and eventually maybe somewhere down the line, you'll say, "Oh, this feels good. This job feels better," but you won't be as intentional, in terms of creating it and what I like about this model of desire it, feel it, experiences it, to me, I sometimes use this idea of double stitching, and really, you're not just saying desire it, you're saying, "No, no. Desire it, then feel it, and then really know what it's like to have something that you really want."

Look around, what does it look like? How do you know? And this is why reverse interviews are so powerful. A lot of people are going to an interview and think, "I'm just here to answer all their questions," but if you really know what you're trying to create, you could say, "Oh, well, can you tell me more about blank, because I'm looking for blank," and that's where creating it really comes in, because the more you really understand what it is that you do want, not what you don't want, you have the capacity to know whether or not you are creating it.

Leah Smart:

Yeah. Most people don't know what they actually want, if it slapped them in the face, because they haven't actually thought about it. They just know what they don't want, but they forget the other part of that is, what you said, "When you know what you don't want, you know what you do want," but actually sit with that. Sit with that, sit with that, sit with that. Because then when it shows up, you can go, "Nope, I don't want that. Moving on. Yes, this is what I want," and then, the whole purpose of this, is to become more clear and intentional about the way that you operate within your life.

And in your life, I do believe there are recipes. I do believe there are routines and rituals, that will just make your life feel richer and I used to not believe that. I used to think, "I want pure freedom. I want to do what I want to do," all that. Once I started connecting more with myself and getting closer to my own experience of spirituality, I was like, "Oh, I want this," and I'm doing this with my hands, and "I want calm. I want contentment, I want ease," and a lot of that for me, gets created through the routines, through the recipes, and through the ability to sit and just show up for my life, in an intentional way.

Daniel Stillman:

Well, man, and we're running out of time, which is crazy. If there was another recipe...

Leah Smart:

I hate it.

Daniel Stillman:

Do you have another favorite recipe for designing amazing, powerful conversations, that you feel like is in your back pocket, that you'd like to share with the world?

Leah Smart:

I got this from Oprah, who I grew up watching every day. There wasn't a day I got home most days, that Oprah wasn't on at 4:00 PT and I've listened to a million of her podcasts. She's probably so deeply ingrained in me and her work and all that, but she shares a story about an interview she'd done, and I believe it was with two members of some white supremacy group, that she'd had on the show and they were live, and they were sitting with her and you can imagine how that went.

Daniel Stillman:

Yeah.

Leah Smart:

It wasn't long after, that she decided with her team, that she would force herself and them to, every single time they were going to have a conversation or pitch a guest, they'd say, "What's the intention behind this?" And she forced that. I actually forced it on myself and my team the beginning of this year. We have a document that has the guests we're all pitching, and it's, "What's the intention?"

If we can't check off a good intention or an intention that's aligned to the work that we're doing and what we're trying to put into the world, then we don't interview that person. We don't reach out, but when I get on an interview and when I'm interviewing and when I'm interviewing someone else, I ask them, before we even start, I'm like, "What's the intention for you, for this conversation or for this work that you're doing?" And that, talk about conversation design, the floodgates open, because that's their heart. If they're truly doing a work that they can get behind, that they believe in, their heart opens right up, and then you flow from there. To me, that's an amazing conversation design, and it lets guards down.

It lets my guard down. When I'm jumping into an interview and I'm running from meeting to meeting, I'm sitting down and I'm like, "Okay, I have to interview this person, and I didn't have time to meditate and da, da, da, da, 18 things happening. What is my intention for this conversation?" And I'm like, "Got it." And to me, let's put it this way, you don't have all the control over where the conversation's going to go. We didn't have it today or exactly what it's going to become, but when you set an intention, you set a direction, and that's a navigational path toward what you're hoping to create and then the rest to me, is faith, that both of you can show up and figure it out together and make magic.

Daniel Stillman:

Yeah. Dance the dance.

Leah Smart:

Dance the dance.

Daniel Stillman:

Oh man. That is so good. That's so powerful. Is there something I haven't asked you, that I should have asked you? Something we haven't talked about, that we should talk about?

Leah Smart:

I don't think so. Oh, wow. Maybe the one thing I'll say, is in all this, I've had multiple experiences, that I get the opportunity to share about the life I'm creating for myself and what I'm learning and I'm wanting to share that with so many people and that it's all a series of trial and error. Even when you've created the thing, you've done the thing, the dream came true, you have your this, you have your that, you're going to come right back to status quo at some point, or you're going to lose yourself and you're going to have to refine the thing.

Daniel Stillman:

Yeah.

Leah Smart:

I've certainly experienced that in the last six months is, "What is my vision? What am I doing? What does good look like now?" And I come back to this idea of, "You'll get it, you'll experience it, you'll feel it. You'll be so appreciative of it, and then it will become a fold in your life. It'll fold right in, and it'll be unrecognizable that you ever lived without it." It'll be life all over and you finding your way again, and you losing yourself again and figuring out and that's something that I think people also don't like hearing, because we like a happy ending and there sure is one, I think, but I think it happens over and over and over again.

Daniel Stillman:

In a way, this is what you talked about last year. It's not a ladder. It's a series of growth and homeostasis and then stagnation, and then more growth, if we are constantly looking at ourselves and what we really want.

Leah Smart:

Mm-hmm. Yeah. It's like summiting a mountain. You climb a bit, you make base camp, you set up, put your stuff down, okay, feel good and then, you've got to keep going.

Daniel Stillman:

Yeah. Yeah.

Leah Smart:

You've got to keep climbing. There's more to go.

Daniel Stillman:

If you were to give this whole conversation a title, what's the title of this episode? Top three titles.

Leah Smart:

How to Stop the Crazy, is one.

Daniel Stillman:

That's good. That's good.

Leah Smart:

I would also call it just Tethered or Re-Tethered is actually what I would call it.

Daniel Stillman:

Oh, it's a good title for a book, if you're thinking about your first magnum opus.

Leah Smart:

It's on the list. I'm currently at base camp right now, but it is on the list.

Daniel Stillman:

Re-Tethered. Could be.

Leah Smart:

Re-Tethered. Yeah.

Daniel Stillman:

Third option, not that I don't like the first two. They're great.

Leah Smart:

The Importance of Intention. Yeah.

Daniel Stillman:

I love it. I like that one. I like that one a lot.

Leah Smart:

I like literative types of things. Anyway, so there we go.

Daniel Stillman:

I love that you dug deep for that one too, with moments to spare, where should people go to learn about all things Smart, IE Leah Smart?

Leah Smart:

Yeah.

Daniel Stillman:

Where should we direct them?

Leah Smart:

Yeah, you can go to my podcast, which today is called In the Arena with Leah Smart. It's a LinkedIn podcast. You can go to my LinkedIn profile. Leah Smart on LinkedIn. You can find me on Instagram. I'm just starting to get myself back into social media. Leah__Smart and my website, Leahsmart.co.

Daniel Stillman:

Sweet. All right. Thank you so much for the conversation. I learned a lot. This was great.

Leah Smart:

Yeah. This was great. Thank you for having me. So easy. We danced, we flowed. Here we are and we didn't even set intention, but we knew.

Daniel Stillman:

Well, I'll call scene.

Leaders as Humble, Audacious, Z-Shaped Coaches

I am excited to share my conversation with AJ Thomas, who I had the pleasure of meeting at the Culture Summit where we were both giving talks. AJ was sharing her perspectives on being a Chaos Pilot at Google’s Moonshot Factory, Called “X”. At the time of this conversation, she’s been with Google for nearly four years, starting as Head of People. 

AJ is also A CxO in Residence at A.Team AND an Advisor at Magic Eden and SemperVirens Capital. She is also an Executive coach on the side. 

She’s got a full calendar.

X, A.Team, CxO. This is starting to sound like the credit roll on Sesame Street! That is a lot of letters, but we’ll add a few more, like T, I and Z.

You may have heard of being T-shaped, as in having breadth of knowledge in general and having depth in one particular area…versus being “I” shaped - having just depth, but no breadth. Breadth is important in any position, because having some breadth means you can more readily engage a broad swath of people in productive dialog, partially because you “get” their inside language enough to collaborate with them. This breadth of collaborative potential is especially important for Leaders.

AJ is a fan of being a Z-shaped-leader, which for her means having depth across many different areas, over time, and the ability to connect the dots between them. But while being able to connect the dots, to scan the horizon for innovation and emergent opportunities, to be able to see an Audacious and almost-impossible future AND communicate that vision to others is a powerful leadership skill, AJ sees Humility as an equally powerful leadership value. This puts AJ in excellent company with Dr. Marilyn Gist, PhD, Professor Emerita of Executive Programs at the Center of Leadership Formation at Seattle University, author of "The Extraordinary Power of Leader Humility," and a past guest on this podcast! Check out our conversation here where Dr. Gist shares her Six Keys to Leadership Humility.

I love AJ’s idea of keeping Audacity and Humility in dynamic tension - staying “Humbacious”! That balance, the ability to “sprinkle” one quality or another into a conversation, shows up as tremendously powerful and generative in AJ’s leadership and coaching work. Audacity holds space for people to explore potential - the biggest vision and possibility. And Humility drives us to assume that we might be wrong and to leverage the mind of a scientist to de-risk the road ahead with powerful questions and intentional experiments.

Enjoy this powerful deep dive into these ideas and a lot more.

AI Automated Summary

AJ and Daniel discuss the concept of being a "Z-shaped" person, with depth across many different areas and the ability to connect the dots between them. They also discuss the principles of coaching, including being present, listening for what has heart meaning, and telling the truth without blame or judgment. They emphasize the importance of balancing audacity and humility in leadership.

Meeting summary:

(3:41) - AJ shares her favorite question to ask in conversations: "Can you tell me what led you to that?" to learn about people's approach rather than just their destination (7:04) - AJ describes the T-shaped person and how they have broad experience in their field and deep expertise in a specific area

(7:36) - AJ describes herself as a Z-shaped person, with depth across many different areas and the ability to connect the dots between them

(15:21) - AJ explains how exploring parallel universes can be valuable for leaders, allowing them to access different perspectives and create more compassionate ways of being and doing

(25:00) - AJ shares the four principles of coaching that have influenced her, including choosing to be present and derisking problems through questioning.

(29:16) - AJ notes that it can be difficult for leaders to hear the truth without blame or judgment, but earning trust through presence and deep listening can help facilitate this (37:30) - AJ introduces the concept of "humbatious" - being audacious yet humble in approaching the future

(41:10) - AJ and Daniel discuss the importance of balancing audacity and humility in leadership

Links, Quotes, Notes, and Resources

https://www.couragetakesflight.com/

www.itsAJthomas.com

Minute 1

Daniel Stillman:

Why do you think you enjoy the unpacking side of a conversation?

AJ Thomas:

I love going a little bit deeper in the conversations just because I'm ever the explorer. I'm just curious about where asking the right question can take you. And unpacking, and maybe it's just because I do this, but it's literally unpacking. When you're packing suitcases and you're unpacking different suitcases, there's always little surprises that you never knew were actually in there. Like the little side pockets where maybe you put a $5 bill or some nice little thing that maybe was just packed away on your journey. I see that as something about conversations as well. You never judge the contents of a suitcase by the suitcase itself, like you never judge a book by its cover. But if you ask the right questions and you're curious enough and you're unpacking enough, you just might find something pretty amazing.

Minute 13

AJ Thomas:

It's just a certain sense of, I think it's just built in for me, but I started describing myself as a Z-shaped person because I'm also very visual. So I was like, okay, the T shape, I get. We learn about it through design thinking. We learn about it in business school, but the Z-shaped has always kind of looked scattered to everyone. And I guess what I wanted to do was describe a way where that is just like a linear path is not wrong, a T-shaped path is not wrong, a Z-shaped path is also not wrong as well.

And so there's probably many different kinds of these things, but for me, what tended to describe my journey most was the ability to go from one vertical to another domain, take learnings from that, then go back and take learnings from that thing and go to something completely different. And then continuing to do that formula. And then really it wasn't until hindsight and I looked back and I stretched that thing that I found that everything in common, whether I was in sales and operations and marketing and product, building for a sports center, in HR, working in talent, whatever it may be, the through line was always about people, culture and organizations and how to build the future of what that looks like. So I think there was no foresight into it. Everything was just as a reflection. And quite frankly, I got tired of defending myself, as I saw it as defending myself. And everyone's like, you do all these things, how do you do all these things?

And I always get the question, how do you do it all? And I always have the same answer and it's only two words and it's always I don't. I don't. But again, it's not until I had the hindsight, I think I'm a little bit later on in my career now where I can say, wow, when I was doing this, was I like, yeah, I'm totally doing the Z-shaped thing? No. I was like, I don't know what's happening, but I'm just going to keep asking questions that's going to lead me to these different things.

Minute 26

AJ Thomas:

the four principles that have really influenced me is one, showing up and choosing to be present is so important. And I said that so fast, you probably almost didn't catch the nuance. A lot of people are told to show up and be present, are you present? Be present. And I think what Professor Angeles Arrien encourages us to do is be present, choose to be present. Being present is a choice. Being active in that is a choice. You're not distracted by anything else but that person you're having a conversation with, and it really helps hold the container for whatever you're going to be talking about or coaching through. The second principle that I loved was the ability to listen for what has heart and meaning for somebody, and it could be what they're not saying. Like when you ask somebody, how are you? And they say, I'm fine. If you really chosen to be present with that person-

Daniel Stillman:

How are you really?

AJ Thomas:

Exactly. You're like, well, let's talk a little bit about that because you say you're fine, but I'm hearing outside of what you're saying through your physical presence that you might not be. So it's really interesting, it helps you pay attention when you choose to be present. You listen for what has heart and meaning for somebody. Or when they say something over and over, but it's kind of glib but then when you really get to the heart of it, they're like, oh yeah, that actually means a lot for me. That's a really interesting one. The third one which I love is the ability to tell the truth without blame or judgment. You have to do that as a coach. And I think especially with working with leaders, it can be really isolating to be at the top. And again, I work with a lot of founders and CEOs where they're probably the only person that feels like they're carrying the burden of all the things.

And sometimes because they're in such positional power, people will not tell them what is wrong or what they feel could be worked on, or what they feel is a blind spot because one, they either have not been invited, or two, because society or the way in which they've interacted with communities has told them that there's a respect for hierarchy. But the respect for hierarchy is also the ability to be able to tell that person in that hierarchical relationship the truth without that blame or judgment. You can't do that without earning trust of course, that's really hard to do. So it's almost a little bit of a paradox. So it's a very interesting navigation of how you're able to really tell the truth without blame or judgment, but you have to be able to choose to be present, listen to what has heart and meaning for people 'cause that burdens the trust to be able to do that.

And then lastly, as a coach you're never advising. You always have to ask and be curious and hold the space, connect back, connect the dots, but that also means you have to be open to outcome and not attached. Which is why giving advice is not coaching.

Minute 36

AJ Thomas:

And I talk a lot about how Moonshot mindsets are accessible for everyone. I think one that I love in particular, an Astro talks about this all the time, is the ability to both be humble and audacious. Which I've then jammed into a word called humbacious. But anyway, it's the ability to be audacious enough to articulate an idea or a path forward, but to also be humble enough to say, I don't understand the entire problem set just yet and so it might not be right so I need to de-risk it, and here's how I'm going to do that.

More About AJ

A lot of what fuels my interests and passions intersect at bridging the gaps in talent, culture and career. The three words above matter to me in the grand scheme of things. The result of what I do moves people and organizations forward to create a future of infinite possibilities. I'm very passionate about building the leaders and organizations of tomorrow. It's never easy, but it is my own definition of meaningful work. I currently serve as the Founder and & Executive Director of Infuse Program Foundation where we turn at-risk youth into entrepreneurs in nine weeks. I also have the wonderful opportunity to serve as the People & Culture leader for one of the nation's largest real-estate online marketplaces. I consider what I do with Infuse and work as a key contributor to developing talent for the future.

Building culture is my knack and creating the conditions for people and their talents to come to life in a meaningful way is what excites me. I am often described as a big picture thinker and fanatic executor, though I consider myself an entrepreneur at heart that's just naturally curious. I like thoughtful approaches to complex problems and creating high impact solutions. I fall deeply in love with problems and am energized by the journey in discovering why they exist and how to solve them. The work I do centers around moving people and organizations forward by way of creating, building and institutionalizing process, and designing/experimenting innovative approaches. I get most of my joy in discovering leadership from those around me and have continuously found that a vast knowledge of intelligence exists untapped just waiting for the right question to be asked.

Full Transcript

Daniel Stillman:

All right. Well AJ, thank you for making the time again and thank you and welcome to the Conversation Factory. I'm so glad you're here. We're doing this and you sound amazing today.

AJ Thomas:

Oh, thank you. I'm really thrilled that we got this mic set up working pretty well for us, so I'm glad to be here with you, Daniel.

Daniel Stillman:

Awesome. So my first question for you is, what are your favorite kinds of conversations?

AJ Thomas:

My favorite kinds of conversations are I think ones you can build on. I never like conversations that are just linear, might as well just be a to-do list or an action item. But I like conversations where you can unpack, get curious, and learn things from. Those are usually the best kinds of conversations without even knowing you were going to learn, going into it.

Daniel Stillman:

Yes. Man, unpacking is like... That is a leadership skill.

AJ Thomas:

That's hard to do.

Daniel Stillman:

Why do you think you enjoy the unpacking side of a conversation?

AJ Thomas:

I love going a little bit deeper in the conversations just because I'm ever the explorer. I'm just curious about where asking the right question can take you. And unpacking, and maybe it's just because I do this, but it's literally unpacking. When you're packing suitcases and you're unpacking different suitcases, there's always little surprises that you never knew were actually in there. Like the little side pockets where maybe you put a $5 bill or some nice little thing that maybe was just packed away on your journey. I see that as something about conversations as well. You never judge the contents of a suitcase by the suitcase itself, like you never judge a book by its cover. But if you ask the right questions and you're curious enough and you're unpacking enough, you just might find something pretty amazing.

Daniel Stillman:

I agree completely. I feel like we could have a whole side conversation about luggage, clearly. I believe that bags are maybe the main thing that differentiates us from the rest of the animal kingdom. And I'm obviously I'm obsessed with bags and I agree with you. I actually love leaving things in my bag from if you travel a lot, it's nice to... When I switched bags recently, I was like, I need earplugs because this hotel's walls are thin. And I was like, damn it, I don't have any earplugs in this bag. I'm so sad. What are your favorite unpacking questions? You talked about how, and I agree with you 100%, the right question can help you with exploration. When you are trying to unpack with people, do you have a favorite question or is it more of a stance or an attitude, do you think, that you bring to it?

AJ Thomas:

I think it's the whole piece of loving conversations that you can build upon. And so it really takes... Crafting the right question often doesn't come with, here's a zinger. She's always going to ask a zinger, right? Yeah, I'm going to talk to AJ. She's always going to ask me this question. It always comes with kind of the exchange of perspectives that you have with somebody and then you build the right question from there. I love that question. The thing I tend to ask quite a bit when I'm in different conversations with folks is just, oh, that's really interesting. Can you tell me what led you to that? Whatever it was, I think it helps people reflect back. It helps people themselves unpack. Or if someone tells me, oh yeah, I ended up doing this thing and then I created this project, which ended up this thing.

Oh, that's really interesting that it ended up in that specific space. Did you ever know it was going to go there? Tell me what led you to that? What were the one or two things that you decided to either follow on a hunch or intuition or whatever that may have led you to wherever that thing is? So I think those are really interesting conversations because you learn a lot about people's approach versus just their destination. And sometimes that's much more fun than like, oh, I won this thing, or I experienced this thing. Oh, awesome. How was that?

Daniel Stillman:

Asking about the journey. Okay. Well, so now I feel like I have to ask you, 'cause we don't always unpack the how you got here question. But you mentioned being an explorer and I'm curious what questions you've been asking yourself on your journey that have brought you to go through some of the journeys that you've been going through. What if I said... This is a really fluffy question, but you see what you can do with it. I don't know.

AJ Thomas:

Yeah, no, for sure. Let's build on it.

Daniel Stillman:

Yeah, let's build. Thank you. Yeah, you're a builder and explorer, so I feel like I can ask a crappy question and you'll just do something good with it, so please proceed.

AJ Thomas:

No, no. There's never any crappy questions, by the way. So just keeping that in mind and riding on that wave and building that, I think what has led me to be an explorer, I could tell you all the motherhood and apple pie things like, oh, I'm just naturally curious and I just really love to see where these destinations take me. But it really is just an interest in the dots that connect things. So for me, for example, because of the profession that I'm in and the line of work that I've been doing, people tend to ask me about my career. What places have you ended up? I'm the epitome of the non-linear person, and it's not by design. It is led by asking the questions. And I think we talked about this previously in other conversations where you have your linear shaped folks, you have your T-shaped folks within an expertise, for example, HR.

I can go really broad on that, and then I'm probably really deep in compensation or in engineering. I'm a really great hardware engineer as a depth piece, but broadly I know everything about full stack. But I think that's the T-shape. For me, I'm really more of a Z-shaped person where I like to explore things here and there. And then I like the alchemy of mashing them up to see if there's any parallels. So for example, I've had the opportunity of having in my background sales and marketing roles, I've been in ground up builds of operational teams, support center teams. I had the opportunity of really diving deep into HR early in my career and then diving out of it and going into something completely different like product, and then becoming a customer of the expertise I spent a lot of my early career trying to hone, and then going back into it as a practitioner with those skills from that parallel universe.

And I've been doing a lot of that in my work to date, to date. Knock on wood. But to date, I've never been in a job that I've ever done before. And it's nice because you proceed until apprehended, but you just can ask all of the questions because you can reimagine certain things in different ways because you haven't traveled it before. Some folks I know that makes them really queasy 'cause it's like, well, how do you build expertise? I think being Z-shaped stacks your expertise because for me, if you think about this zigzag shape of a career, if I then pull it, the through line has always been people, culture and organizations. And I think that's beautiful. I can layer in coaching in that, which I've done. I can layer in the understanding of financial markets, which I'm currently doing right now with the work that I'm studying around venture capital and private equity.

I can layer in operationally, how do you build a tech stack into that? And sometimes people are like, you know a little bit about everything as you're a jack of all trades and master of none. Actually, no, I'm not. I'm just actually innately curious of where I can connect the dots. And I think that's where, for me being an explorer is fun. I want to come prepared to an unknown situation with... I use a lot of analogies, so tell me if this is a lot, but think about it as my most creative self is maybe a chef, we'll put that as a thing. They create amazing dishes and experiences, et cetera for people, but they travel the world tasting different ingredients. And at the off chance that they're somewhere where they need to then cook a dish, they have all of this access of these spices that they have collected.

For me, those spices are perspectives, those are skills, those are experiences that I never would've been able to do if I were just trudging along this linear path. There's nothing wrong with the linear path, by the way. I want to make sure that that's clear because I think there's a lot of vocations and professions that have that. But I think for me, what works because of the work that I do is this explorer mentality and then giving back to that exploration through connecting the dots in whatever journey you're going after. And you leave a little bit of what you've found before included in the new thing that's being created and I think that's fantastic. I mean, that's the way I think about coaching as well, is where can we collect these different perspectives and then how do we connect the dots to an insight?

Daniel Stillman:

So when did you start thinking about yourself as a Z-shaped person? And so just to review, 'cause this is interesting, I want to make sure I understand it. The T-shaped I'm familiar with the model and you described it. You have broad experience in your field and then have or actually brought experience outside of your field. You can maybe collaborate across multiple fields 'cause you know something about many things, which I think is, I can't remember if that's the hedgehog. The hedgehog knows a lot about one thing. The fox knows many things, but the hedgehog knows a lot about one thing. And you want that. You do want that depth in a person that you're hiring where you know what you're hiring and that they have deep expertise in this.

But a Z-shaped person, it sounds like there's multiple depths. There's depth across many things. You know many things about many things and there's a slash across everything where it's transdisciplinary. Tell me more about this mental model and I actually don't know if it's your model or if it's something that you started to absorb from... Is it out there in the ether that I just missed this or we just need to buy your book when it comes out about Z-shaped people?

AJ Thomas:

Hopefully it's the latter. I don't know. I'm a self-described Z-shaped person. I don't think there's ever been a model out there, but I think it just came out. And if there is, awesome. I haven't even Googled it or anything. Maybe we should and just see.

Daniel Stillman:

Pause for a moment, everyone.

AJ Thomas:

The rise of the Z-shaped person. No, I think for-

Daniel Stillman:

It's a good title. That sounds...

AJ Thomas:

For me what I think is really interesting is the depth doesn't have to be vertical. The depth can also be horizontal. And when I started describing myself as this Z-shaped person is when I started getting into conversations where people were asking me, how did you end up doing these many different things? You're a singer, you're a sales, you're in marketing, you're coaching.

Daniel Stillman:

By the way, I'm going to interrupt you. So if you don't know, you missed the first five minutes everyone when AJ went through three different microphones that she was choosing amongst to hack into her computer. And one of them, it was Chrome, beautiful microphone. I know.

AJ Thomas:

Wait, hold on.

Daniel Stillman:

Yeah, I know. It's amazing. It's a gorgeous microphone. So yes, you maybe you'll get an... It's like an EGOT. It's the person who can get the Emmy, the Grammy, and the Tony.

AJ Thomas:

Oh my gosh, I don't know if I'm in that category, but I will say I have the heart of just trying things, things that are unknown. Typically, if you put me in a predictable environment and I have to be there, I'll find a way to make it unpredictable. If I'm in an environment where it is unknown, I'll find a way to build. It's just a certain sense of, I think it's just built in for me, but I started describing myself as a Z-shaped person because I'm also very visual. So I was like, okay, the T shape, I get. We learn about it through design thinking. We learn about it in business school, but the Z-shaped has always kind of looked scattered to everyone. And I guess what I wanted to do was describe a way where that is just like a linear path is not wrong, a T-shaped path is not wrong, a Z-shaped path is also not wrong as well.

And so there's probably many different kinds of these things, but for me, what tended to describe my journey most was the ability to go from one vertical to another domain, take learnings from that, then go back and take learnings from that thing and go to something completely different. And then continuing to do that formula. And then really it wasn't until hindsight and I looked back and I stretched that thing that I found that everything in common, whether I was in sales and operations and marketing and product, building for a sports center, in HR, working in talent, whatever it may be, the through line was always about people, culture and organizations and how to build the future of what that looks like. So I think there was no foresight into it. Everything was just as a reflection. And quite frankly, I got tired of defending myself, as I saw it as defending myself. And everyone's like, you do all these things, how do you do all these things?

And I always get the question, how do you do it all? And I always have the same answer and it's only two words and it's always I don't. I don't. But again, it's not until I had the hindsight, I think I'm a little bit later on in my career now where I can say, wow, when I was doing this, was I like, yeah, I'm totally doing the Z-shaped thing? No. I was like, I don't know what's happening, but I'm just going to keep asking questions that's going to lead me to these different things.

Daniel Stillman:

Yeah, you were just chefing.

AJ Thomas:

That's it.

Daniel Stillman:

So you mentioned the parallel universes, in your perspective, is some of the bars of the Z the parallel universes, or is it more the exploring multiple cuisines and sampling spices and understanding like the salt, fat, acid, heat of other ways of doing things? Tell me your perspective on parallel universes as an important metaphor for a leader to be looking at their work in.

AJ Thomas:

I think a parallel universe. So for example, and again this is the analog, for me was seeing the way that product managers approached user testing. Taking the designing from outside in so that you can design for an experience versus just an event was really valuable for me. So for example, in HR, I see this in the function and I see this with leaders where we'll take, someone's going to have a hard conversation and it's going to happen on April 19th at 2:00 PM because that's the next one on one so we designed for that event. Everything's got to go right and here's what I'm going to say, and we're going to use this method and we're going to ask these questions. But rarely is going into that conversation about, I'm going to have that conversation on the 19th at 2:00 PM, but I want to design it from May 1st backwards.

I learned in product the power of future casting that because you could change the factors. If you just switch the parameters a little bit, you can change the factors of the design of whatever your apparatus is, whether it's a hard conversation or a decision or a strategy. It allows for you to be more aware of the things surrounding your decision making as a leader. And I think the parallel universe is really grabbing some of those things. I mean, each of the different functions are interesting, but there are ways in which finance teaches us about empathy. There are ways in which engineering can teach us about ways in which we approach unlocking hard problems. There are ways in which customer support can teach an engineer the other side of unpacking the huge problem, but then being able to tell the story about the huge problem. So I think there's a lot of those that I tend to think about when I think about parallel universes and what leaders can access.

It creates compassion in your way of being and doing because you're going to then be naturally curious, that's interesting. How does that work in support? Why does the utility of this function process in this way? And how do I get a little bit of that into this? I mean, you're seeing it in recruiting where there's the parallel universe of marketing and people want to take that aspect of building a CRM and nurturing a pipeline the way you would before you launch an event or a product. How is that different from you want to bring a hire into your organization and you want to make sure that they know about that organization? Rather than, oh, I'm going to hire somebody and I'm going to tell them about the company. What if through the journey of them coming to your company, they're already getting to know you? So there's a lot of parallels that I think if we stopped and really got curious around the organization, the utility and the things that they're known for that they're really good at, what could we take in?

Like I said, what's engineering known for? Building great things and tackling huge problems. Okay, well, where are we building great things and tackling huge problems? You could be doing that in any vertical.

Daniel Stillman:

Yes.

AJ Thomas:

But find out what's the best things they're doing in there. And then how do you implement that in your universe?

Daniel Stillman:

Well, it seems like there's actually two flavors of parallel universes that you delineated. One is, and I think this is a classic design thinking perspective of how do I learn about hospitality? Who does hospitality well in the universe? How can a hospital learn about hospitality from a hotel? What can a hotel learn about hospitality from a hospital? What does customer service really mean? And what are all the ways to absorb and cross fertilize excellence in an organization? Which is super powerful. But there was another type of parallel universe you were talking about, which is designing a difficult conversation, not as a, okay, I'm going to have conversation about topic one, two, three and four, and then I'll be done. But saying, what do I want it to be like two days, two months, two years after? Designing for what are all the ways that this conversation could continue?

AJ Thomas:

Could manifest, yeah.

Daniel Stillman:

Could manifest. And that's designing from almost a multiverse approach of this conversation could go many, many different ways. It could go to shit. It could create amazing positive alignment. It could create forced agreement. And it sounds like you're also designing your conversations. I would call this is the question going forwards or backwards in time? You're almost saying which of the many scenarios that are possible do I want to design backwards from?

AJ Thomas:

Well, if you think about that if you're sitting as a CEO, and I coach a lot of founders and advise a lot of founding teams, and one thing I always encourage them is... So for example, I had a CEO that was rolling out their performance management program and was like, "Hey, let's look at this narrative, this deck. Does this look good?" And the question I really had for them was, I mean, that's great. Would your content change if you designed it not for the event you were going to roll it out for, but a quarter after?

Daniel Stillman:

Yeah.

AJ Thomas:

Would there be anything added to that? Would there be anything taken away? And that's how you begin to future proof through scenario planning. I would say, a more elegant and slightly elevated way of thinking about scenario planning is looking at all of the other possibilities. Now, they may never come through fruition because you're really just trying to nail this one specific thing, but I think it makes you more organizationally aware and agile because if it did come up, you'd have at least thought about it.

Daniel Stillman:

Yeah. Well, I think it's very easy to be in survival mode and say like, well, I just need to get this plan so I can get out to this next thing. And you're asking them, what are we really trying to do here? So this gets to the question, the other thing we really wanted to talk about was being a coaching leader or having a coaching mindset based on whatever your coaching philosophy is, which I want you to unpack for us versus a therapist, which is a very different, maybe much more reactive and palliative approach of, yeah, well, let's work through the feelings and get you to the next thing versus a coaching approach, which at least what I'm hearing from you say is what would create a real lasting transformation? A moonshot, if you will.

AJ Thomas:

Impact. Yeah.

Daniel Stillman:

Impact.

AJ Thomas:

Yeah. No, I mean it's really interesting because when I was going through and doing my coaching journey, I was at the service of an executive team and I felt like my utility was really just being a therapist, because you have to hold space. You have to hold space in those spaces. You must. It is a requirement of the job to do that, but it felt like it was really-

Daniel Stillman:

When you say holding space, explain what you mean by holding space for that kind of a conversation.

AJ Thomas:

I mean, really letting people unload on you sometimes because that's what they need because they don't have that safe space to be able to do that. But I felt incapable of holding the right space without challenging as their leader also to give them back their agency, right?

Daniel Stillman:

Yes.

AJ Thomas:

I'm going to say, this is going to sound funny, there's a fine line between a brainstorm and a bitch fest.

Daniel Stillman:

Yes.

AJ Thomas:

And I think coaching helps you give people back the agency that they always had, by the way.

Daniel Stillman:

Yes.

AJ Thomas:

And it's done through a series of unpacking with the right questions. And so as I think about it, my whole coaching approach and again, was really influenced by these four principles by Dr. Angeles Arrien, which I learned through the Berkeley Executive Coaching Institute. It was a really interesting approach in a sense of how she studied the ways that Shaman Tribes communicated with each other, and it's actually been a very near and dear principle to me that I hold in certain spaces when I'm having conversations with folks. Which really, when you're coaching somebody you're really just having a conversation and you're holding that space for that person and then holding up the mirror back to them to make sure that they at least get a playback of what that looks like. And then you ask questions to help them de-risk their problem. And in some cases, that's kind of what we do with Moonshot's too. Identify a huge problem, ask questions to de-risk. That's simplifying it, of course.

But the four principles that have really influenced me is one, showing up and choosing to be present is so important. And I said that so fast, you probably almost didn't catch the nuance. A lot of people are told to show up and be present, are you present? Be present. And I think what Professor Angeles Arrien encourages us to do is be present, choose to be present. Being present is a choice. Being active in that is a choice. You're not distracted by anything else but that person you're having a conversation with, and it really helps hold the container for whatever you're going to be talking about or coaching through. The second principle that I loved was the ability to listen for what has heart and meaning for somebody, and it could be what they're not saying. Like when you ask somebody, how are you? And they say, I'm fine. If you really chosen to be present with that person-

Daniel Stillman:

How are you really?

AJ Thomas:

Exactly. You're like, well, let's talk a little bit about that because you say you're fine, but I'm hearing outside of what you're saying through your physical presence that you might not be. So it's really interesting, it helps you pay attention when you choose to be present. You listen for what has heart and meaning for somebody. Or when they say something over and over, but it's kind of glib but then when you really get to the heart of it, they're like, oh yeah, that actually means a lot for me. That's a really interesting one. The third one which I love is the ability to tell the truth without blame or judgment. You have to do that as a coach. And I think especially with working with leaders, it can be really isolating to be at the top. And again, I work with a lot of founders and CEOs where they're probably the only person that feels like they're carrying the burden of all the things.

And sometimes because they're in such positional power, people will not tell them what is wrong or what they feel could be worked on, or what they feel is a blind spot because one, they either have not been invited, or two, because society or the way in which they've interacted with communities has told them that there's a respect for hierarchy. But the respect for hierarchy is also the ability to be able to tell that person in that hierarchical relationship the truth without that blame or judgment. You can't do that without earning trust of course, that's really hard to do. So it's almost a little bit of a paradox. So it's a very interesting navigation of how you're able to really tell the truth without blame or judgment, but you have to be able to choose to be present, listen to what has heart and meaning for people 'cause that burdens the trust to be able to do that.

And then lastly, as a coach you're never advising. You always have to ask and be curious and hold the space, connect back, connect the dots, but that also means you have to be open to outcome and not attached. Which is why giving advice is not coaching. Sometimes people can flame-

Daniel Stillman:

Fine, fine line.

AJ Thomas:

Exactly. Well, there's also that fine line of being that therapist. You don't just say, tell me more. You say, huh, I really see that this is affecting you.

Daniel Stillman:

So what's the fine line between telling the truth to someone and giving them advice? Because I could see how in a way you're revealing something to someone, that's not telling them necessarily to fix it, but by telling it to them you are telling a truth about the fact that that's something that they could look at.

AJ Thomas:

I mean, it could be something as simple as we've talked about we can say, "Hey, Susan, we've talked about this topic a few times now, and I've heard you say the word I don't mind at all. And then I see you get really passionate about the specific example when we talk about it. Can you tell me a little bit more about that?" Okay, we'll unpack. All right. And then the reason why I'm asking that is because I sense there's a little bit of you do care about this, that you do care deeply because of the way we've unpacked these specific examples. So telling the truth without blame or judgment could just be pointing them to that one thing that they might unconsciously not even know they're doing. Like oh, this is really great, but I don't really care about that. It's fine. You know when people say that, it's fine and then you unpack it a little bit and they're like, well, actually, there's these couple things that have happened in the last couple of weeks. And I'm really curious you've said it's fine three times describing the specific situation, is it really fine?

That's a way of being able to tell the truth without blame or judgment. And also it comes with trust. You got to get to know folks and say, hey, I know in our last conversation, this is where you connect the dots as a coach, I know in our last conversation what was really important to you was that people collaborated well to get to the outcome you were looking for. And now I'm hearing that you think it's fine that they're not. That's really interesting. You find that interesting? So stuff like that where it's you're really bringing those pieces in from what they're reflecting to you is a way to be able to tell the truth without blame or judgment. Without saying, hey, I don't think you really care, but I've heard you say these couple of things where actually you do, don't you? So it's a very fine line, but it's about connecting it and reflecting it back to them in a way where they have the agency to ask that question for themself without you telling them.

Daniel Stillman:

Well, so this is the other piece that I wanted to pull back a layer on, because agency and being directive versus evoking or provoking people to think for themselves. A lot of people feel like leadership is about being directive and authoritative, and you have a value of bringing your coaching skills into your role as a leader. So I'm wondering if you can talk a little bit about how you balance those roles, because occasionally one must be directive, or can you just lead through good questions and deep listening and telling the truth and being open and not directive?

AJ Thomas:

Well, I mean, I'll tell you it's really hard to do it. It's really, really hard to do it because as a leader with your coach's hat on you still have to get shit done, right? It still needs to happen. But again, what I put in the center is whoever that person is am I giving them back agency in how I'm showing up for them? Again, that could be in a question, that could be in a directive to say the only directive is the goal. So that's how I think about it. And if we agree on the goal, you can go kick the ball however you want to. We can agree on the approach, but your technique is your technique, and I'm going to ask. And sometimes I think there are team members who want you to outline it for them, but I always have to say that's great. One idea is to do it X, and then I don't let them off the hook and I will say, what is your idea? Let's hear your idea. Let's see if we can build on that.

If they're lost and they want you to tell them something, I would say, well, how would you approach it? How would you approach it? Okay, that's really interesting. Why don't we build on that with what we know? Let's go back to the goal. So my job as a leader is to align people to the goal because the goal is in service to the mission to help the company succeed. And so as long as I know that's my role, I can continue to play the coach role. If I forget that that's my role, I'm going to be directive and authoritative because I need to get shit done. And I know that's oversimplifying things, but I think for me, that's what I've learned. I used to be the leader that was like, here's our task. Here's what we got to do, da, da, da, da, but what people need is also the context and the agency to say, okay, I can get this done. It is well within my power to be able to do that. And if I'm lost, I can always anchor back and I can anchor back if I'm lost on what the goal is.

Because then people get to see themselves whether or not it's a stretch or it's easy or whatever. And again, it's about giving them back their agency. If I've forgotten as a leader that my job is to clarify the goal and to make sure that the mission is clear, then I will end up being directive and authoritative. There's no other way around it.

Daniel Stillman:

Well, I'm wondering, because I want to talk about your title of chaos pilot, and I feel like in a world of complexity and maybe even chaos, to me it seems almost hubris to say that there is one right way to do things. It seems like a lot of humility comes from the recognition that we are just in a very complex, borderline chaotic situation and our job is to move through that and with a view of alternate worlds and parallel universes, there may not be. You are not coming as a leader saying that there is one best way, and that you know it.

AJ Thomas:

Yeah. You just really can't.

Daniel Stillman:

Unless I'm just putting words in your mouth, but that's the vibe I'm getting.

AJ Thomas:

Well, no, it's true because it's also working in the space that we work in. And I talk a lot about how Moonshot mindsets are accessible for everyone. I think one that I love in particular, an Astro talks about this all the time, is the ability to both be humble and audacious. Which I've then jammed into a word called humbacious. But anyway, it's the ability to be audacious enough to articulate an idea or a path forward, but to also be humble enough to say, I don't understand the entire problem set just yet and so it might not be right so I need to de-risk it, and here's how I'm going to do that. I think it's particularly important when you're working on things that are huge. I always like to say as well, there are people that are really passionate about their work. I can be so passionate about everything that I'm doing right now, but I also feel a sense of responsibility because the work that I'm doing touches the future in some way.

I have three kids myself, and the legacy I'm going to leave behind for them if I'm going to spend 80% of my time at work doing the things that I do is going to be shaped by how the future can show up in the work that we do in the present. And so I think it's really crucial that you don't... I always say, first rule of working on the future is for you to know you don't know it. And anybody out there who is working on the future that says I know exactly what it's going to look like, what we're going to do, here's where we need to go is automatically wrong. Because if I could be so bold to say or audacious enough to say, because the future requires you to constantly ask questions, to constantly de-risk, to constantly test things, and that's fine. But I think in the meta of things, you're always building on something. You're always building on something, and it's never that that one thing that was done is final.

You think about technology and the internet, we're all done for Y2K. Internet is here and now at the rise of generative AI and artificial intelligence or machine learning, there's always something to build on.

Daniel Stillman:

Yes.

AJ Thomas:

Once you plateau at the infrastructure and you create a new operating system, new apps will be built on that. New features and skillsets will be built on top of those new apps.

Daniel Stillman:

Yeah, that we can't participate.

AJ Thomas:

And the cycle starts all over again. So I think, yes, you should assume that you don't know, but be audacious enough to still explore anyway.

Daniel Stillman:

These two values of humble and audacious are really interesting. Lately, there's this wonderful concept of polarity mapping and polarity thinking in management. If you've got these an two angels on your shoulder, one's humble and one's audacious, we can over index on one and there's positives of each pole, and there's negatives of over indexing on each pole to the detriment of the other.

AJ Thomas:

Absolutely.

Daniel Stillman:

Do you feel like you're navigating those two poles in your work? What happens if you lean too much in one way or another for you?

AJ Thomas:

Well, I mean, I think if you lean too much on being audacious you end up really leaving a trail of folks behind you because you're not bringing them into the conversation in a way where you can get collectively curious. I think if you lean too much on humility, you'll never get anything done because you're never going to want to start it 'cause you're always thinking, okay, well, maybe not now, maybe tomorrow. So you got to have a little bit of that-

Daniel Stillman:

Yeah, and why me?

AJ Thomas:

Yeah, the imposter syndrome are settling in rather than having just a little sprinkle of that audacity can really take you there, and then a little sprinkle of humility on the other side. You don't want to change who you are, but you do want to live in the tension of what's the other side of this look like, right? I think some of the greatest leaders out there can see both or four or three sides of an argument, and I always think there's three sides to an argument; yours, mine, and the truth. So it's a very interesting, again, paradox, but I think it's also just very important to hold that tension. I navigate it every single day, and I got to tell you it's not easy.

Daniel Stillman:

No.

AJ Thomas:

It's hard.

Daniel Stillman:

Yeah.

AJ Thomas:

The part that I have to constantly work on is when I get triggered, when do I know I'm being too much of one? It's like your strengths, right? Strengths overused are detrimental to you, but if you have them just toned in the right pocket you're fine. Same thing with much of a good thing. So I think it's not the ability of whether or not you're ambitious or humble. It's not that at all. It's the ability of being able to know when you need to sprinkle a little bit of each in moderation to whatever it is you're working on because some tasks-

Daniel Stillman:

Yeah, or de-sprinkle or to pull back on one versus the other.

AJ Thomas:

Yeah, Absolutely. Absolutely. And again, that's the tension. A lot of people will say, that's context switching. No, it's not. It's being aware that it's there. Half the battle is knowing you're going to encounter that.

Daniel Stillman:

Yes. And to have control in the use of self to say, how may I... 'Cause I have a sticky note in front of me that says audacity from one of my good friends who's actually a therapist. And he was the one who said like, yo, I try to really remember to be audacious, to lean in and say what my clients may not want to hear, but they need to hear. And that's a lever that we can pull.

AJ Thomas:

That is.

Daniel Stillman:

But also let go because as you said, if that's all I'm doing is just pressing the audacity button, I'm not going to get what I want.

AJ Thomas:

Yeah, you won't get the utility of the audacity button.

Daniel Stillman:

Which is not always pressing it.

AJ Thomas:

That's right.

Daniel Stillman:

We've gotten so close to our time, God, we've covered a lot. What have I not asked you that I should have asked you, AJ? Because I have the humility to know I can't know all the things to ask.

AJ Thomas:

I love that. I don't know. I mean, yeah, no, that's a really good question. I mean, I would say we covered a lot of things. I think there's probably some areas where being a mother is a different intersection as well, and a working mother as well, but we can have a whole other conversation on that.

Daniel Stillman:

Happily, yeah. If you coach your kids.

AJ Thomas:

I think it's the other way around. I learn a lot from them. I learn a lot from their very interesting questions. Actually, my daughter and I, we wrote a children's book all from her question of, well, how hard could it be? It was really hard, but it was more of the curiosity of, okay, well, even if we don't know let's just try. And the next thing you know, we've got an award-winning children's book in our hands, which was really awesome. But discovering little things like that. I mean, because I work a lot in the future like I said, it's not just a passion for me. I feel responsible because I'm literally raising three humans who are going to be in the future.

Daniel Stillman:

They live there. That's where they're from.

AJ Thomas:

Yeah, that's right. And so I want to make sure that whatever I pour into it has that consideration in mind, because it can be so easy to be wrapped up in what's happening day to day that you forget that what you're actually working on is never going to be something that you may ever see in your lifetime. At least for me, that's true, right?

Daniel Stillman:

Yeah.

AJ Thomas:

So I think that, but other than that it's all kind of relative to our conversation today.

Daniel Stillman:

Well, I've never asked this question before, what would be the title of this conversation do you think? If you were to give this conversation one or two titles, what would you say this conversation-

AJ Thomas:

Oh, this conversation?

Daniel Stillman:

This conversation, yeah. What was this conversation about? What's on the cover?

AJ Thomas:

Oh, that's a really good one. I don't know, purveyor of perspectives.

Daniel Stillman:

I have a vote for there's a fine fine line between a bitch fest and a brainstorm.

AJ Thomas:

Oh, that's a good one. I got a lot of love for that one. I got a lot of love for that one. That one was just off the cuff, but-

Daniel Stillman:

I mean, there's so clearly so many books that you will one day write AJ, one of them might be these Z-shaped people and it's another really interesting overarching theme for this. So what it's like to be a Z-shaped coaching leader, it's a very different approach.

AJ Thomas:

Yeah, it is. I mean, I'm pondering a little bit more on that. I'm trying to learn as much as I can in the spaces that I'm in. I mean, because there's other spaces of access. I'm a Filipino first generation immigrant. I don't have a lot of folks that I can look up to in the industry that's doing stuff like this. And so in some spaces I feel like I'm breaking into these types of conversations, but I know I'm not alone. And I'd love to see more folks that look like me that have these different experiences in parallel universes talking more about what it feels like for them as well.

Daniel Stillman:

Yeah. Well, thanks for being part of the conversation and being so generous with your perspectives. It's been really, really delightful. Where ought people to go to learn about all things AJ Thomas on the internet if they want to get to know you better?

AJ Thomas:

I'm on LinkedIn, or you can find all of the ways to connect with me on, it's ajthomas.com.

Daniel Stillman:

Sweet. We will direct people there. Well, I think we will call scene.

AJ Thomas:

Woo.

A Company Must be a Community of Practice

In this episode I talk with my friend Chris Murchison, who is a coach, a facilitator and a talented artist, too!

We talk about his Four principles of Communities of Practice and how building a positive culture within an organization requires, essentially, creating a community of practice. Your team, your organization, is already practicing something…and that practice is either mindful and intentional, or it’s habitual and haphazard. 

Communities of practice are groups of people who share a passion for something they do and so, have a shared purpose or goal for learning how to do it better…and so, they interact regularly with the intention of continuous improvement of that thing.

An example of intentional practice that Chris shares in the opening quote is what he calls a “Sunset Meeting”, a special, extended, and deeper version of a Retrospective, that asks, not just how did the work go, but how did we do? Stopping to look back and look forward means that the space for continuous improvement is being created.

But without fostering deep psychological safety for people to say what needs to be said, a leader and a team can never get the continuous relevant learning they need from the conversation. How to lead that kind of safety is a whole other conversation, but Chris and I do unpack some of the facilitation skills leaders need to master in order to be able to host these types of continuous improvement conversations.

Communities of practice require ongoing conversations and intentional practices. Chris shares four key principles to help you architect an effective community of practice for your own context:

  1. Meaningful connection (In order to, as Chris says, plant the seeds of trust and safety)

  2. Relevant learning (So people want to be full there AND so the organization benefits)

  3. Purposeful practice (so we’re focused on what matters most)

  4. Sharing and reflection (slowing down to notice and share what we’re each practicing and learning )

Make sure to check out the links and show notes which include Chris’ wonderful Community of Practice Guide and his more general Community Principles & Practices.

AI Automated Summary

9:39

Chris explains his interest in learning and community, and how they led him to the idea of communities of practice

11:56

Chris and Daniel discuss the idea of organizations as communities of practice and learning organizations

15:13

Chris discusses the importance of psychological safety in organizations and how to create a sense of trust and safety for employees to express themselves

19:36

Daniel adds that safety, expression, and learning are all interconnected and that regular intentional practice is necessary to create transformative conversations and communities of practice

41:05

Facilitation skills are important for creating meaningful connections and purposeful practice within a community of practice

47:35

Chris Murchison and Daniel Stillman discuss how building a positive culture within an organization requires ongoing conversations and intentional practices, and how everyone in the organization can be considered part of a community of practice

Links, Quotes, Notes, and Resources

Chris's Website

Community of Practice Guide

Community Principles & Practices

Minute 1

Chris Murchison:

And the community of practice concept is essentially that. It's just the idea of bringing people together who have a common kind of domain, if you will, share a profession or share something that's of interest to them so they have a reason to be together. And then within that reason there's a sense of connection and community and then there's within that community something that they want to do together and learn together. And so I think I was just so drawn initially to this idea of learning and learning with other people. And so when I came across this concept of communities of practice, it just rang so beautifully for me as something that felt true and youthful and powerful.

Minute 6

Chris Murchison:

In my work within organizations, both as an internal employee and more recently as a consultant, one of the things that I observe and have experienced is a constraint or the difficulty of expression. And oftentimes in organizations, I will experience employees being fearful of speaking up or fearful of speaking the truth to leadership or fearful of, if I say this, I'm going to appear stupid or less intelligent. Or if I say this, I might get reprimanded or there might be some kind of retribution of some kind that I imagine. And it's interesting, and these are all smart people and organizations that support things like showing up authentically and bringing your best self to work, that there can still be this interesting underlying fear.

So I think this relates to this concept of psychological safety and so how do you actually go about building an organization community where there is a sense of trust and greater sense of safety to be courageous and speak more of your truth? I think that's an aspiration and a challenge for many individuals and for many organizations. And so when I think about your question, I think what I would say to a leader is now how do you create ways for people within your workplace community to feel more safe, to feel more courageous, to create the space for people to experiment with expressing themselves more?

And so it might be creating opportunities for people to practice, make these micro practices of connecting. And I mean maybe that's at the root of it sort building the relationships and building enough trust within those relationships across the organization, across your community, so that over time you kind of build a sense of trust and with that, a sense of safety. But then I think allows you to step forward more and to be more courageous in expressing yourself when maybe you have a disagreeing opinion or when you have a piece of feedback that might be more constructive, that you will lean into that because you really trust the relationship and trust that it'll be fine no matter how nervous you might be, that the outcome will likely be trusted and fine. I think also creating some structures to help people begin to practice sharing more. And so I think how do you be thoughtful about creating and you're [inaudible 00:09:25] is creating conversation structures where people are invited to share things.

Another example is a sunset meeting, for example, after a project, rather than getting together and just talking about did you hit your milestones and how did you improve this system or that system and blah, blah, blah, blah, in a typical retrospective, but how do you include in that, how did we do? How did we collaborate? How did we get along? I've sat in many or observed many project teams where there were clear interpersonal challenges or struggles at different points as is naturally human. But how do you create the space for a conversation to also include those reflections on, well, where were those moments where things got a little tricky or hard and how do we reflect on those and how do we learn from those so that we can collaborate better in the future?

Minute 25

Chris Murchison:

And I've been doing a lot of work with art-based coaching recently and learning a lot about it. And one of the things that I find quite remarkable is that sometimes words are just not adequate. And this might be helpful advice for leaders as well, sometimes it might take using a different medium to support people in engaging with their feeling about a topic or a question. And so it might mean engaging in some art-based activity or engaging in a movement activity or taking your team out for a walk in nature to inspire them in a different way in response to a question you're wanting to discuss with them or have with them.

So I think that's really interesting is that sometimes it isn't asking a question and getting words back. Maybe it's asking a question and maybe there's some other medium that you might engage people in that helps them engage that subconscious below the water line kind of level of experience. That might help different words come out eventually, but I think that experience with the art or with nature or even poetry or other mediums can really sometimes help people come up with an even better answer.

Minute 41

Chris Murchison:

I mean, organizations also move fast these days, and so I could imagine people saying there just isn't time to have these kinds of conversations. I certainly have clients who feel that this is a good idea, but we have 10 items on our agenda list, and we maybe have five minutes or some kind of check-in or conversation about how we're doing. So yes, crises require attention, but at a certain point, I imagine a community would want to pause and think about, well, why are we in constant crisis? Or how might we engage and look differently to maybe get out of this loop of constant crisis?

Or how has this experience of being in crisis all the time affecting me and my work or my relationships with this team or with the organization? I mean, being within an organization is a complex experience. And so I always feel like you need time and space to reflect on that experience and to collectively understand what's being developed from that collective experience because sometimes to your point, sometimes that's all it's developing underneath the water line, and it could be developing in positive ways or it could be developing in some destructive ways. And if you don't create the space to understand and allow people to express what they're feeling, you may never know.

More About Chris

My career has spanned the higher education, for-profit, non-profit, and philanthropic sectors. This have given me a unique and diverse perspective on the experience of work and workplace culture.

I have held roles in student services, employee development, human resources, talent and organization development, and more. As a practitioner and consultant, my work is inspired by the research and frameworks of positive organization psychology, art and movement, mindfulness, emotional intelligence, appreciative inquiry, and applied improvisation.

I am constantly learning and evolving my practice. I appreciate multi-disciplinary approaches and the unique solutions that are created as a result.

Full Transcript

Daniel Stillman:

I will officially welcome you to the conversation factory. Chris, I'm really, really glad we're having another conversation and to be talking about this topic specifically. It's a really rich topic, so thanks so much for making the time for this. As you mentioned in your busy, busy, over busy schedule. So thank you.

Chris Murchison:

You are so welcome. I really enjoyed our first conversation, so have been anticipating this one. I'm looking forward to it.

Daniel Stillman:

There are so many delightful, the designed conversations, the toolkits on your website that I really cannot remember how I stumbled upon, but the community of practice guide and the way you break it down, it's such a rich conversation topic. And I want to start at the origin for you about why you value, how you came to value the idea of a community of practice. Can you take us back and take us to how it came to be something that matters to you enough to put that whole beautiful document together?

Chris Murchison:

Yeah, I think if I were to boil it down, I would bring it to probably two interests that I have. One is learning, and then the other is community. And when I put those two things together, learning in the presence of others or with others, to me that just creates a powerful vehicle for growing together. And the community of practice concept is essentially that. It's just the idea of bringing people together who have a common kind of domain, if you will, share a profession or share something that's of interest to them so they have a reason to be together. And then within that reason there's a sense of connection and community and then there's within that community something that they want to do together and learn together. And so I think I was just so drawn initially to this idea of learning and learning with other people. And so when I came across this concept of communities of practice, it just rang so beautifully for me as something that felt true and youthful and powerful.

Daniel Stillman:

One of the things as we were just having our planning conversation, the thing you mentioned blew my mind, the idea of thinking of an organization itself as a community of practice. This seems to connect to the idea of learning organizations.

Chris Murchison:

Absolutely.

Daniel Stillman:

What organization should not be intentionally connecting people to learn, to grow, to create rituals of connection.

Chris Murchison:

Absolutely. I think that's definitely an aspiration. I think what many organizations are searching for or experimenting with are what kind of structures really support being a learning organization. And yeah, there might be ways of looking at it through the lens of training and development or learning and development or lens of organization development to think about how to build a learning organization. I love this idea of community. And so when I was in my last organization, Hope Lab, this is something that we kind of stumbled upon was what if we think about ourselves as a community rather than as a culture? And the focus for in recent years for organizations has been how to build a strong culture, how to build a positive culture, which is definitely a good thing. But I found myself thinking about what if you took that a step further? What have you thought about the organization as a community and a community within which you practice building culture and sustaining culture?

And there was something deeply resonant in that idea for me because if you think about the idea of community, to me it sort of signifies certain kinds of behaviors. But then the community, you participate, you are a citizen of that community, you feel like you have an obligation to support that community and it's growing over time. You're a part of it. You're a what builds it and makes it happen and sustains it. And for me, within that idea, I thought, well, culture fits within that as a culture isn't necessarily something handed down to you. It's something that I think you build within community together and you create this thing that we call culture and then that evolves over time and molds based on leadership, based on the individuals within the organizations and how they relate to it to each other and the kinds of behaviors and rituals that they build with each other intentionally or unintentionally sometimes as well.

Daniel Stillman:

If you were talking to the leader of an organization who knows that they want to improve their culture, who's thinking about having a more learning oriented, growth oriented culture, it is a really interesting shift to think about coming at it from a, well, I don't want to fix my culture, but I want to grow our community. How does the approach shift for them? What would you want them to be thinking and doing and being? How would you want them to be showing up differently to lead a community rather than trying to develop or shift a culture?

Chris Murchison:

In my work within organizations, both as an internal employee and more recently as a consultant, one of the things that I observe and have experienced is a constraint or the difficulty of expression. And oftentimes in organizations, I will experience employees being fearful of speaking up or fearful of speaking the truth to leadership or fearful of, if I say this, I'm going to appear stupid or less intelligent. Or if I say this, I might get reprimanded or there might be some kind of retribution of some kind that I imagine. And it's interesting, and these are all smart people and organizations that support things like showing up authentically and bringing your best self to work, that there can still be this interesting underlying fear.

So I think this relates to this concept of psychological safety and so how do you actually go about building a organization community where there is a sense of trust and greater sense of safety to be courageous and speak more of your truth? I think that's an aspiration and a challenge for many individuals and for many organizations. And so when I think about your question, I think what I would say to a leader is now how do you create ways for people within your workplace community to feel more safe, to feel more courageous, to create the space for people to experiment with expressing themselves more?

And so it might be creating opportunities for people to practice, make these micro practices of connecting. And I mean maybe that's at the root of it sort building the relationships and building enough trust within those relationships across the organization, across your community, so that over time you kind of build a sense of trust and with that, a sense of safety. But then I think allows you to step forward more and to be more courageous in expressing yourself when maybe you have a disagreeing opinion or when you have a piece of feedback that might be more constructive, that you will lean into that because you really trust the relationship and trust that it'll be fine no matter how nervous you might be, that the outcome will likely be trusted and fine. I think also creating some structures to help people begin to practice sharing more. And so I think how do you be thoughtful about creating and you're [inaudible 00:09:25] is creating conversation structures where people are invited to share things.

Another example is a sunset meeting, for example, after a project, rather than getting together and just talking about did you hit your milestones and how did you improve this system or that system and blah, blah, blah, blah, in a typical retrospective, but how do you include in that, how did we do? How did we collaborate? How did we get along? I've sat in many or observed many project teams where there were clear interpersonal challenges or struggles at different points as is naturally human. But how do you create the space for a conversation to also include those reflections on, well, where were those moments where things got a little tricky or hard and how do we reflect on those and how do we learn from those so that we can collaborate better in the future?

Daniel Stillman:

I love so many things in that response, I drew this little triangle of learning, requiring safety to express. And unless we have all of those pieces there, if a leader is not creating the conditions, this is the way I define leadership, is that creating the conditions for a transformative conversation for people to say what needs to be said. If we cannot create the conditions to say what needs to be said, we won't express what needs to be expressed and what I think maybe if I were to put something at the center of that triangle, it's practice not for nothing. That's what a community of practice, this is our topic of the day is how do we actually create regular opportunities for people to intentionally practice these things? And that doesn't come for free.

Chris Murchison:

No. And it's not necessarily easy. So I mean, acknowledge that that can be really hard.

Daniel Stillman:

That's when I say it doesn't come for free that's my general bucket for what we used to say in physics, non-trivial. There's no trivial solution for this. It takes money, time, effort, focus.

Chris Murchison:

Yeah. Takes all of those things. Definitely. I had a thought and it's flown out the window.

Daniel Stillman:

Oh, that's wonderful. What color was it? Let's see if we can follow it.

Chris Murchison:

Yeah, it might have been orange.

Daniel Stillman:

I'll look for an orange streak in the sky. Well, while you're remembering what you forgot, I have a card here on the four principles of communities of practice from one of the resources from your website, meaningful connection, relevant learning, purposeful practice, and sharing and reflection. And I would welcome you speaking either to all of them as a whole or to one that you think is highest value and highest leverage for a leader thinking about creating these conditions. I'd love to peel the onion of what does it take to actually create these opportunities for regular expression of relevant meaning.

Chris Murchison:

Yeah. Well I first, I remember that thought that went out the window. The orange one with the-

Daniel Stillman:

He's big in orange. He's come back in.

Chris Murchison:

Which I think relates to what you were just asking.

Daniel Stillman:

That's amazing.

Chris Murchison:

So people oftentimes use the iceberg to describe culture, organizations. And so above the water line you might see all of the observable things, artifacts, behaviors within an organization, values, observable practices, et cetera, but beneath the water line and as we know with icebergs, what's beneath the water line as often bigger than what's above. So beneath the water line might be all the kind of unexpressed values or the implicit knowledge, tacit knowledge, the routines and things that are more quiet or underground, less expressed or on sidelines, on unexpressed emotions, feelings, even ideas and thoughts might live below the water line.

And so I think if you think about communities of practice within an organization, I think your question speaks to how do you create the environment within which the waterline lowers and you're creating greater opportunity for people to express all of those things that might be beneath the water line and bringing them to above the water line. And so I do think connection, as we were just talking about before, I think connection plays a big part. So the quality of your relationships, the quality of your connection with each other can really support your sense of safety or trust within that space, within that community. And with that hopefully builds your courage to be able to express more, speak more.

Daniel Stillman:

What structures, because you mentioned... Oh, sorry, go ahead. You were taking a breath now. Keep going.

Chris Murchison:

Yeah, I was thinking about your other points, your four points that you were sharing. Sharing a reflection was the fourth one of the four that you described. I do think structuring opportunities for people to practice sharing, how do you maybe create structures within meetings that invite people to share and maybe pose questions to them that are really thoughtful questions that really invite people into them. And so not a question like, oh, how was that? But a question that really takes it to a deeper level. What was your experience when you... So really I think that kind of a question invites someone to step into it and hopefully speak with some truth rather than the larger broad question, which might even overwhelm people because they don't really know how to answer it.

Daniel Stillman:

So this comes to a point of one of the other things I wanted to poke at was, I loved your check-in deck because I love recipes, but we're really talking about rituals, structures that as you said in that document, supporting people feeling welcomed, which is a value for you that comes from how you were raised from your life experience, that it's important to welcome people and use the word invite, which is one of my favorite words. We're really trying to create powerful invitations for people to really say what needs to be said. How can a leader who's listening to this tap into that power of invitation to make people feel welcomed, to ask questions that actually help people feel comfortable, to peel just a little bit more?

Chris Murchison:

Well, I think I can connect this again back to the four points that you mentioned earlier, connection, learning, practice, and sharing and reflection. I mean, I think the idea of coming from this check-in deck that I produced, but the idea of drafting or structuring exercises that invite people into conversations that support them learning. And so a good question can also inspire people to think at a meta level about how they're engaging with their work or how they're engaging with each other and what are they learning from that engagement and how might they want to improve that the next time or build upon that the next time or within their work tasks.

Really thoughtful questions or activities can help people be really meaningfully reflective on what risks they took, how they tried something, maybe it didn't work out as well as they wanted to, or what have supported them reaching their goal or what got in the way, what might they try differently? So I think through thoughtfully structured questions, thoughtfully crafted even activities for a team can really help group reflect and to learn together from their experience. And that's how you also build your practice together. So if you're a team that's focused on collaborative collaborating to work on a project together or you share a common practice across an organization, being able to come together and reflect collectively allows you to improve upon that practice as well.

Daniel Stillman:

Yeah. It's funny, when I was writing down these four principles from your own document, I wasn't thinking, when I put that together with this idea of an organization as a community of practice. Those become leadership principles. Let's lead meaningful connection so that we feel safe to express. Let's make sure that we're providing relevant learning to feed purposeful practice so that we can actually get better at what we're trying to do here. And I think that's one of the core issues of psychological safety is its we can't do it all the time. It's absurd to think that we can do it all the time. There is always going to be learning and practice and sharing and reflection so that we can continuously create that loop of becoming better at what we're doing together.

Chris Murchison:

Yeah. And it's a virtual loop. So the more we're willing to extend ourselves to try things, to be courageous to experiment, the more we're able to reflect on those actions that we took, then that feeds our learning. And when we go back to do that thing again, we have the wisdom that we've just garnered that we can apply to the next round and then hopefully the next and the next and the next in this upward beautiful upward spiral.

Daniel Stillman:

It is a virtuous loop. I think it's very well said and something I'm looking at the iceberg that I sketched while you were talking about it and just being aware that there is a line and that there is something below the line, I feel like creates some more empathy. One thing I post reposted this or someone reposted this of that I wrote way back, the gap between the amount that we think, the pace at which we can think and the pace at which we can talk. And I think it's very... I'm curious what you think and how you would respond to this perspective. I think it's a very easy to have the expectation that people say and are saying all that they can say that when somebody says what they've meant to say, we've heard everything that they can say on it.

But there's always a very huge fundamental gap between all that we can think about something, all the things that we might say about something and what we actually did say in the time that we had, it's very easy to just assume as a leader, well why wouldn't somebody just say everything that they meant to say and what they've said is what they've intended to say and there's nothing below the line because why would there be? I just asked them a question and they gave me an answer. Let's keep going. Let's move on with the conversation. But it takes, I think, a real shift in empathy and also willingness to slow down to go below the line because it's not easy to go below the line. It's much easier to say, "Okay, thanks for your answer, let's go."

Chris Murchison:

Yeah, I love that. I think I came across that same piece of data recently, and it seems so true that, I mean similar as you were just describing with the iceberg model for us as individuals as well, that we have these thoughts that we can share quickly perhaps with our words or we say something with our words in response to a question. But to your point that there's only so much our brains can pull together and express with our mouths, but there's a lot more-

Daniel Stillman:

It's so true. Just can't pull more together in the time of us.

Chris Murchison:

Yeah, there's so much more happening I think in our belts experience in the subconscious that to your point, takes more time to understand and to connect with and to be able to express and your earlier metaphor of an onion. I mean, there's probably many layers to the onion when we think about a question. They're probably, if you sit with it long enough, there might be many different ways to answer that question or how I answer it now might be different to how I would answer it tomorrow morning or next week. And I think there's definitely power to allowing enough time to in a way mine all of the perspectives that can come if we give people the structure and the time to get below the water line into their more different kind of their deeper feelings or emotions or thoughts about a topic.

Daniel Stillman:

Yeah.

Chris Murchison:

I think this has an introversion extroversion element to it as well. I mean, I know as an intro introvert, I oftentimes need more space. I mean, I can say something, but whatever I say in the moment quickly never feels satisfactory. I know if I had more time to think about it, that there's probably a better answer or a different answer or a deeper answer. And in a similar way, I think everyone can benefit from more time to sit with the question and fully grasp it and fully grasp the different ways they might think about it.

Daniel Stillman:

Yeah. It's the thought, the thinking, talking, intention, Venn diagram might be shifted differently for people who self-identify as introverts versus extroverts. But I think the fundamental math of we can think at 4,000 words per minute and we can only speak at 125 means that the physics is against us.

Chris Murchison:

Yeah.

Daniel Stillman:

There's just no way we can say everything that we intend to say. No one can.

Chris Murchison:

And some things are just difficult to express in words at all. And so I've been doing a lot of-

Daniel Stillman:

Makes my heart just melt, just it's so true. I feel that.

Chris Murchison:

And I've been doing a lot of work with art-based coaching recently and learning a lot about it. And one of the things that I find quite remarkable is that sometimes words are just not adequate. And this might be helpful advice for leaders as well, sometimes it might take using a different medium to support people in engaging with their feeling about a topic or a question. And so it might mean engaging in some art-based activity or engaging in a movement activity or taking your team out for a walk in nature to inspire them in a different way in response to a question you're wanting to discuss with them or have with them.

So I think that's really interesting is that sometimes it isn't asking a question and getting words back. Maybe it's asking a question and maybe there's some other medium that you might engage people in that helps them engage that subconscious below the water line kind of level of experience. That might help different words come out eventually, but I think that experience with the art or with nature or even poetry or other mediums can really sometimes help people come up with an even better answer.

Daniel Stillman:

It's so interesting because I assume you've been exposed to the Johari Window at some point in your work, and I'm thinking about one of the check-ins in your check-in deck and your artwork. So the random box of objects where people just pull out a random object from a box and basically confabulate, say this object connects to the core challenge or my key insight from this because blank and people just make something up, right? They literally make something up because that's what we do as humans. We confabulate, and I'm thinking about your collage work and how it is a way to tap into that quadrant of the Johari Window of the unknown unknowns. It is to tap into the subconscious or the collective unconscious in some way.

Chris Murchison:

Yeah.

Daniel Stillman:

I'm just freewheeling here, but I feel like there's a connection between what you just said around peeling back layers and getting into the unconscious and using unexpected approaches to try and get people to express and some of the things that you're clearly attracted to in your own work, some of your own expressive modalities.

Chris Murchison:

To me, there's different modalities, are just a different way of expressing, and I find it quite powerful. I know that when I have brought in kind of unusual activities to help a group think into the future or begin to envision the future of the organization or to think about themselves in their personal development in five years, or to think about some complex dynamic that they might be experiencing in a team or with a coworker, sometimes again, it's hard to find the words or saying the words might feel a little scary even.

But to be able to use a different source to help channel those emotions and those feelings and eventually those words. So again, finding a poem that somehow captures the essence of your feeling. That could be amazing and beautiful and allows you to express what you're feeling in a different way. Or for me, with collaging, thinking about a question or a situation and being able to piece together quite intuitively images that seem to express how I'm feeling about that situation or that person. It just allows me to express myself in a different way and sometimes in a more honest way than if I were just using words.

Daniel Stillman:

Yeah.

Chris Murchison:

Yeah. I think if you also think about centers of intelligence, I mean, we are in our heads so much, and so it's helpful for me as well to get out of my head. And by using other methods like art or again, poetry or other things, it kind of takes me out of my head and draws upon other kinds of wisdom that I have. It might be more emotional wisdom or physical wisdom or creative wisdom, but it gives me different kinds of information than I'm just coming at a situation or a question from my head. And I find all of that information, all of the sources of wisdom really helpful. And so if we can balance them all as we think about how to respond to a question, to me that's beautiful. That's powerful.

Daniel Stillman:

Yeah. And this goes to... Sorry, was there something else that you wanted to-

Chris Murchison:

Well, I was going to say, to me, to loop it back to communities of practice, I mean, to me that's the beauty of intentionally building a community of practice, whether that's an organization as a community, and thinking about that body as a group that elevates its own practice and learning together. Or if it's in designing a group of people to come together and to meet regularly for the same purpose of learning together, connecting with each other and elevating or improving your practice together. I think that at the core of that is creating that structure that really supports people in having a successful experience.

Daniel Stillman:

Yeah. Well, that actually connects with one of the cards that I have not talked about that I'm curious about, because you mentioned the power of facilitation skills to when you think about creating meaningful connection and these opportunities for purposeful practice and your value of supporting people and feeling welcomed. It is a skill to host these kinds of spaces, to provide the structures that make it happen within one instance, but also to facilitate it as a cadence of conversations because a community practice doesn't mean wants, right?

Chris Murchison:

Right.

Daniel Stillman:

I'm thinking about what's the minimum viable structure, the minimum viable community of practice. How should someone really get started? Obviously meeting once is a good start, obviously psychological safety, having that ethos and the empathy to look beneath the water line is important. But what are the structures that you'd like to see more organizations putting into place to get started in creating more shots on goal for meaningful connection and purposeful practice?

Chris Murchison:

I think facilitation is needed and important. I used to think that groups could be more self-initiated, self-sustaining, and I think that's possible if you have a purely skilled group of participants. But I would say in my experience that my experience in groups has been if you don't have someone who is holding the space for that group, helping that group keep organized, it doesn't have to be a heavily managed kind of organizing or facilitating, but I think it has to be a gentle enough kind of herding and shepherding, if you will, to keep the group focused and moving forward together. And so in my facilitation of communities of practice, whether that's in an organization or outside of organization, to me, one of the first things out the gate is establishing connection. And so if you have a group of people who are coming together, I think initially you want to create a strong foundation of relationship.

And so what can you do, what can you structure to support people engaging with each other, beginning to share information about each other, getting to know each other in a way that feels meaningful so that you begin to plant those seeds of trust and safety within the group. And also not just trust and safety, but also people begin to care for each other. They begin to be curious about each other, hopefully beginning to be interested in each other and what they're practicing, what they're doing in the world. And then that creates a kind of energy of excitement of wanting to meet with these people. So I think once you've established that foundation, then you can move into that sphere of what we want to learn together. And so I think that also requires some facilitation to help the group surface kind of what's important to them. What's something that they can agree on that they want to spend their time together discussing or learning together.

And it's not as easy as you think, sometimes in a group people are bashful and it can be hard to... People might be willing to go along with what Sally says or what Joe says. And I think that's a part of the dance of building enough trust in the group that people are willing to put out there what it is they're interested in so that you're able to see the full kind of menu. And then the group can decide what priorities they want to tackle first. Then there's the question of how, once you identified topics, I think there's how do we want to engage in these topics. And again, if you've built up enough of a strong foundation, the group can participate in kind of co-creating, well, do we want to just have an open discussion or do we want to bring in a speaker or do we want to read something together? I mean, there's so many different ways that you can engage learning and building your practice that ideally you want the group to all weigh in on deciding together collectively, both the what and the how.

Daniel Stillman:

That is a lot of work.

Chris Murchison:

It's an investment in the beginning, maybe that's true of most things they tackle in life. Make that initial investment to get it started. And hopefully once it's off the ground, you've got enough momentum that it can begin to move more easily on its own. Maybe people begin to volunteer to help with different sessions, or you develop a structure for the meetings, which carries itself from meeting to meeting to meeting, or you begin to develop rituals. And so people come knowing what to expect in a meeting. So I think it's yes, an investment in the early part to establish those structures, and then some gentle support and facilitation ongoing to keep it moving.

Daniel Stillman:

One thing that I'm hearing is that leaders should expect that it's going to take some time and some investment to get a return on a community of practice that is not a chocolate bar, a quick fix, it's not a sugar rush, it's a long arc.

Chris Murchison:

It is. Well, I think if you're talking about communities of practice outside of an organization, like a group of professionals, for example, who come together or they want to form a cohort and meet together, focus on their practice together, that can have a lifetime or a lifespan of its own. It could last for six months or a year. It depends on a number of factors. Within an organization, that's an interesting question because by the sheer nature of this group of people working together, they're probably in the same environment, in the same community for some time whether or not this community of practice idea takes off or not. But I think maybe it depends a little bit on what the goal of the community of practice is. And so if the goal is a more broader, how do we build community within our workplace?

How do we make sure we're mindful of culture and building all the practices and processes that support our positive culture? Yes, that's an ongoing thing. Everyone in the organization could be considered part of that community of practice. And so therefore, you would want to be really thoughtful about how you craft conversations at your staff meetings or your team meetings or supervision meetings or your performance conversations or onboarding. And it kind of permeates everything. But how do you be thoughtful about all of those different conversations to make sure that everyone's engaged in this idea that building culture is a practice, it's an ongoing practice, and how do we collectively support that practice and improving it over time.

Daniel Stillman:

Yeah. In a way, this sense of we are a community together and we are continuously co-creating our culture through the conversations we're having, the ones we are, the ones we're not, and the quality of the conversations we're having. And it sounds like in a way, regularly reflecting and sharing and practicing intentionality around what are the conversations we want to be having more of and less of, really keeping our eye on that ball.

Chris Murchison:

Absolutely.

Daniel Stillman:

It's a big vision and it's really powerful. What else? There's more there.

Chris Murchison:

I mean, organizations also move fast these days, and so I could imagine people saying there just isn't time to have these kinds of conversations. I certainly have clients who feel that this is a good idea, but we have 10 items on our agenda list, and we maybe have five minutes or some kind of check-in or conversation about how we're doing. So yes, crises require attention, but at a certain point, I imagine a community would want to pause and think about, well, why are we in constant crisis? Or how might we engage and look differently to maybe get out of this loop of constant crisis?

Or how has this experience of being in crisis all the time affecting me and my work or my relationships with this team or with the organization? I mean, being within an organization is a complex experience. And so I always feel like you need time and space to reflect on that experience and to collectively understand what's being developed from that collective experience because sometimes to your point, sometimes that's all it's developing underneath the water line, and it could be developing in positive ways or it could be developing in some destructive ways. And if you don't create the space to understand and allow people to express what they're feeling, you may never know.

Daniel Stillman:

Yeah. Where are we rushing to? Or I think there was a check-in your deck about what is my relationship to busy? What is busy winning us right now? What kind of busy do we want to be? Really investigating in busy. Speaking of busy, I'm going to assume that, well, I know you're busy, so we have a little bit of time left. What haven't I asked you? What have we not expressed? What is still below the line that should be above the line? What have I not asked you that I should have asked you, Chris, on this very, very rich topic that clearly we couldn't bring to full expression in the time we have, but is there anything else that we haven't said that should be said?

Chris Murchison:

Yes, I have been very delighted by some of the work done by a couple names, Beverly and [inaudible 00:43:33], [inaudible 00:43:33] Trainer. They actually live not too far from me here in Portugal, but they've done decades of research and work about social learning and developing this concept of communities of practice. And if you go online, maybe we can link to it in your podcast, but they have some beautiful writing about what they have seen as the core elements that create a community of practice, the core principles that support them being successful, the common things that communities of practice tend to discuss or the kinds of things that help people feel that the time is valuable in a community of practice.

But I think their work is particularly useful in thinking about the possibilities coming out of communities of practice. I think the idea, we started out with this, but the idea of thinking about communities of practice as something an organization can be, can inhabit is a little unusual and different. I love the idea and I think I'm really happy that we had a chance to play around with that thinking a little bit, but I think it's interesting to apply it to an organization setting and the idea that an organization as a community can be a community of practice. I love that.

Daniel Stillman:

Yeah. I mean, definitely from my experience, communities of practice that exist organizationally or where people are showing up as an individual, there's high investment, each individual's bringing a lot of juice from their own passion to get better. But the other piece that we're talking about, an organization, seeing themselves as a learning organization and investing in the skills that they want to invest in, it's a very different problem, and I think people do show up differently in those contexts. I'm happy to include a link to the work of these folks that you were mentioning. If people want to learn more about all things, Chris Murchison, where else can they go on the internet to learn more about the things? I'm happy to link to all of the resources we've talked about today as well.

Chris Murchison:

Well, I did courageously create a website last year that is available. It includes some of my musings about the workplace. It includes some of my artwork. It includes some of the products that I've designed and built. You've mentioned one, the check-in deck. It also includes a document produced with the University of Michigan's Business School about building communities of practice specifically for groups of people who are practitioners of positive organizations, psychology. So yeah, my website is a good source. I wouldn't say that's all things Chris Murchison.

Daniel Stillman:

We know there's more below the line.

Chris Murchison:

Yeah.

Daniel Stillman:

There's parts of you that will be forever unknowable. Well, I really appreciate you making the time to express and elucidate these really, really important pieces of your work and this work that is creating communities where people can get better at the things that they really, really value together. So thank you so much, Chris.

Chris Murchison:

Thank you.

Coaching from Essence, Creating from the Future

Today, I sit down for a conversation with *my coach* Robert Ellis, about his new book, Coaching From Essence.

Robert has been described as “one of Silicon Valley’s best-kept secrets” and has been coaching leaders at startups, mid-stage companies, Fortune 500 giants, and nonprofits for over 30 years. Robert has taught leadership and coached entrepreneurs at Singularity University and developed Level UP, the leadership curriculum for the Global Startup Program, and taught leadership courses at Stanford University. We met through radical serendipity and I’m grateful for the generosity and grace Robert has coached me with. All of his teaching materials are now publicly available on his free circle community and on youtube.

Robert’s book is like sitting in a fireside chat with Robert, absorbing his profoundly wise and profoundly simple approaches to coaching. Sometimes, a new idea can feel so true that it lands like common sense - all the pieces fitting together so seamlessly and effortlessly. Roberts’ metaphors, stories and models hit like that - like powerful truths you knew all along.

Robert’s visual models help ground a coaching conversation, make it easy to follow along, and make the conversation incredibly sticky. And literally every time I’ve drawn one of these diagrams for a client, it lands with them and becomes a new metaphor for thinking about their challenge and their path forward.

This book isn’t just for coaches who want a more effortless and human approach to doing this work, it’s for anyone who wants to be deeply helpful to their clients, their teams, their organization, and to lead conversations in a more impactful way.

Coaching from Essence is based on the radical idea that everyone has an essence, and that, when we work from it, we can effortlessly create value and impact. Coaching from essence works both ways - the coach coaches from *their* essence, their natural approach…and the coachee is coached to work from their *own* essence - their own natural approach. We’re not telling people how to be. We are here to help them remove the obstacles that get in the way of them finding their own way.

According to Bill Gates, everyone needs a coach. 

I would flip this suggestion on its head and say that at some point in everyone’s lives, accessing a Coaching from Essence mindset can be a generous, powerful and transformative way to help someone in our lives.

Some of us choose to make coaching our life's work, but Coaching from Essence is a powerful, generous and transformative approach to helping people that everyone can (and should?) access at the right moment for the right person. 

Robert Ellis is the embodiment of what he teaches - he is a generous, powerful and transformative coach who I’ve had the pleasure of working under for several years. I’m so glad this book is finally out in the world so that everyone can have the experience of working with him.

Links, Quotes, Notes, and Resources

https://coachingfromessence.com/

https://www.futurosity.com/

Coaching from Essence, by Robert Ellis

Minute 1

Daniel Stillman:

I love that you quote Dolly Parton, I think she's under-quoted, and there's this beautiful quote about, "Find out who you are, and do it on purpose." And I'm curious, if you can put that in context for you. Who are you, and what is it that you do on purpose?

Robert Ellis:

What I do on purpose, is I help people create things. So the book is called Coaching from Essence, and briefly, the idea behind that is, I believe that everyone has an essence, which I think of as, everyone has a way of being valuable in the world without any real thought or effort on their part.

Or another way of thinking of it, a shorter way of thinking of it, is just that everyone has a way of being good.

And so I think, what Dolly Parton is talking about is find out who you are, find out what your essence is, find out why you're here, and what you can contribute naturally, and do that on purpose.

And what most of us do, is we do something else. I know I spent the first 60 years of my life doing something else, trying to be someone I wasn't, because I thought that would earn me more money, or get people to love me, or help me survive, or get status, or something like that.

And so what Coaching from Essence is really about, and what that quote means to me, is find out who you are naturally, what do you naturally good at? Well, what do you naturally have to offer the world? And trust that if you create a life out of that, you'll actually create a, not only be more successful in all of the usual terms, but you'll be happier and more fulfilled.

Minute 3

Robert Ellis:

I have a particular way of thinking about leadership, as you know, but kind of the short version of it is, that a leader is someone who can help people navigate through the unknown, to something better than they can imagine when they leave, wherever they start. And one of the best ways to help people navigate the unknown, is to coach them.

And coaching is really just a way of helping someone find out what their essence is, and begin to create from that, but also how to go on a quest, or how to navigate the unknown to create some something, to create more possibilities than they would otherwise have available.

Minute 17

Robert Ellis:

Leadership is, if you really want to live an adventurous life, you open yourself up to the possibility that the universe knows better than you what you could create, what's possible, and so you go on a quest to find out what's possible. You aim for B, but in this case, B is the best thing that you can imagine, and you conduct experiments, you try different things, and that's how you learn and grow.

Minute 18

Robert Ellis:

Growth to me is also not necessarily bigger. It's better, more congruent, more resonant, more authentic, more aligned with who I am. The more I create a life that is more resonant, congruent, and aligned, the more fulfilled I am, the happier I am.

Minute 41

So the futurosity continuum, and the reason it's called the futurosity continuum, is that, basically, what we're trying to describe is, what is your stance toward time? Are you creating from the past, or are you creating from the future?

Okay, so the continuum goes from the past to the future, and it starts with reactive. Reactive, meaning, something happened already and now you're just reacting to it, and you're putting out fires, or you're just in problem-solving mode. You're just reacting. You're not in control. You're just reacting to things that have already happened, so that it's very much, you're trying to manage the past.

Daniel Stillman:

Which is a really hard thing to do, by the way, given that it's already happened.

Robert Ellis:

It's a hard thing to do, right? Exactly.

So now, you're trying to fix the past, okay? You're a fixer, if you're reacting, or you're proactive.

Proactive is just, so something has happened often enough that you finally catch onto it, and you say, "Okay, let me see if I can avoid that happening again." That's proactive, but if you're reactive or proactive, you're still responding to the past, so you're what I call a fixer. That's a fixer.

After proactive is opportunistic. Once you start to create from the future, in other words, once you start to move towards something you think you want, once you start creating, you will create all kinds of possibilities. Some of which, will be aligned with your quest. They'll be directionally appropriate for what it is you're pursuing, and others that are shiny objects, they're distractions. And this is one of the problems that leaders and entrepreneurs, especially, can fall right to. So, opportunistic, but at least now you're moving toward the future. You're creating possibilities, that didn't exist before, that might lead to something good.

Strategic. The way I define strategic, is you're intentionally setting about creating a future of your own choosing. So you have an idea of what you want, and now you're taking action to create what it is you think you want.

And again, if you're on a quest, you don't know it's possible, but you have an idea of the best thing that you can imagine, so being strategic, is intentionally taking steps to create something, the best thing that you can imagine. Okay.

Then beyond strategic, is emergent, which is, now, you're in conversation with the universe. In other words, you're paying attention to what results you're getting, what response you're getting, and so you have to pay attention to weak signals. You're noticing just what's showing up for you, and you're seeing whether or not some of these things, whether or not you're creating possibilities now, that are potentially better than you might have entertained before.

So the difference between emergent and opportunistic, is that opportunistic is kind of random, and emergent is things are responding to what you're putting out. You're more intentional.

Summary

(6:49) - Robert explains that he helps people create things from their essence and discusses the importance of coaching for leaders in navigating uncertainty and creating more possibilities

(23:51) - Robert defines growth as becoming more resonant, congruent, authentic, and aligned with who you are, rather than just getting bigger

(32:13) - Robert talks about the balance between path-like and quest-like approaches in organizations, and the need for experimentation and learning to avoid being outpaced by competitors

(34:28) - Robert discusses the antidote to self-interest, status-seeking, scarcity, and survival, which he sees as essence, abundance, service, and trust. He emphasizes the importance of giving oneself away and trusting in one's natural abilities and creativity.

(45:40) - Daniel introduces the Futurosity Continuum as a model for navigating uncertainty and creating from the future

(47:36) - Robert discusses the ideal curve of spending more time on strategic and emergent thinking, with most organizations and startups spending more time on reactive and proactive thinking.

(1:00:13) - Robert explains that the purpose of his work is to help individuals and organizations express their essence and create something meaningful that improves the world

More About Robert

Robert is an executive coach and the founder of Futurosity and the Coaching From Essence training program for executive coaches.

Robert has over 30 years of experience working with global companies—spanning startups, mid-stage, Fortune 500 giants, and non-profits— guiding leaders to take their impact to the next level at any stage of growth. His proven strength in coaching entrepreneurs and CEOs to become better leaders, think more strategically, create high-performing teams, foster future-friendly cultures, and deliver compelling presentations—including several high-profile IPO roadshows—has earned him praise from one client as “one of Silicon Valley’s best-kept secrets.”

He’s taught leadership and coached entrepreneurs at Singularity University, and developed Level UP, the leadership curriculum for the Global Startup Program.

He was one of the original coaches for the Nasdaq Milestone Maker program, helping late-early to mid-stage entrepreneurs grow their businesses to the next level.

He also taught Facing Challenge, Navigating Change: Leadership and The Hero’s Journey, an 8-week course at Stanford University using Joseph Campbell’s Hero’s Journey as a framework to explore mindsets and skillsets for leading yourself and others on a heroic journey in business and in life.

Full Transcript

Daniel Stillman:

I will welcome you, officially, to the Conversation Factory.

Robert Ellis:

Thank you.

Daniel Stillman:

Robert, thanks for being here.

Robert Ellis:

I'm thrilled to be here, Daniel. It's always nice to have a conversation with you.

Daniel Stillman:

So where shall we begin? I feel like I was leafing through the early copy of Coaching from Essence, and I love that you quote Dolly Parton, I think she's under-quoted, and there's this beautiful quote about, "Find out who you are, and do it on purpose." And I'm curious, if you can put that in context for you. Who are you, and what is it that you do on purpose?

Robert Ellis:

What I do on purpose, is I help people create things. So the book is called Coaching from Essence, and briefly, the idea behind that is, I believe that everyone has an essence, which I think of as, everyone has a way of being valuable in the world without any real thought or effort on their part.

Or another way of thinking of it, a shorter way of thinking of it, is just that everyone has a way of being good.

And so I think, what Dolly Parton is talking about is find out who you are, find out what your essence is, find out why you're here, and what you can contribute naturally, and do that on purpose.

And what most of us do, is we do something else. I know I spent the first 60 years of my life doing something else, trying to be someone I wasn't, because I thought that would earn me more money, or get people to love me, or help me survive, or get status, or something like that.

And so what Coaching from Essence is really about, and what that quote means to me, is find out who you are naturally, what do you naturally good at? Well, what do you naturally have to offer the world? And trust that if you create a life out of that, you'll actually create a, not only be more successful in all of the usual terms, but you'll be happier and more fulfilled.

Daniel Stillman:

Yeah. Why is coaching a useful modality? Both for leaders to utilize for themselves, but also to use for their teams, and their organizations? Like why coaching, rather than other ways of helping in a conversation, for lack of a better word?

Robert Ellis:

Well, I think that coaching is one of the most important skills for any leader. I have a particular way of thinking about leadership, as you know, but kind of the short version of it is, that a leader is someone who can help people navigate through the unknown, to something better than they can imagine when they leave, wherever they start. And one of the best ways to help people navigate the unknown, is to coach them.

And coaching is really just a way of helping someone find out what their essence is, and begin to create from that, but also how to go on a quest, or how to navigate the unknown to create some something, to create more possibilities than they would otherwise have available. And so coaching is a way of being, which creates more possibilities.

So it's important for leaders, it's the reason I love it, is because it's a form or a context. People can enter into a conversation with me, as a coach, and there's an understanding that we're in conversation in order to create something different than what they already know or have, so it opens up tremendous possibilities, and that's exciting for me.

Daniel Stillman:

So navigating uncertainty.

Robert Ellis:

Yes.

Daniel Stillman:

How does coaching someone help them navigate through uncertainty, rather than, I think, what many people want when they're in uncertainty is, tell me how to be, tell me to think, tell me what to do. We all have a feeling of wanting a playbook, a handbook, a path when we're in uncertainty. There is a tendency, and you could point it to patriarchy, or fear. I mean, I don't know what you would pin it to, but there is a move in many of us to say, to grab for the handrail of certainty, in uncertainty.

Robert Ellis:

Yes. Yes. Well, the way I think about it is, first of all, we're all taught, what I think of as, the unconscious curriculum, we're all taught what will make us happy, is self-interest, status seeking, scarcity, and survival. And so if you're creating from self-interest, status seeking, scarcity, and survival, there's a lot of fear there.

And so, the way I think of it, sometimes, I'll draw this out for a client. I'll say, "All you're trying to do is get from A to B," and I put a dot under A, and a dot under B.

And when you're looking at a piece of paper with A and B, with these big bold dots underneath them, they look kind of like planets.

Daniel Stillman:

Yes.

Robert Ellis:

And so A is a little bit like earth, and B might be like the moon. Well, the earth has a lot more gravity than the moon, if you're on earth, and so, one of the things that keeps us wanting to be in a place where we know, is that it's safer.

So I agree with you, part of it is this sort of curriculum we've been taught about what will make us happy, is we cling to self-interest, we cling to what we think will help us survive.

And then there's fear. And there are some specific fears, that tend to come up when someone tries to navigate uncertainty. There's, what I call, thresholds, silliness, trust, sanity. The most important threshold is the love threshold, which is that we're all afraid that if we really pursue what we want, we'll discover that we're not worthy, not lovable, there's something, we don't deserve it.

Daniel Stillman:

Yeah.

Robert Ellis:

So to navigate the unknown, we have to be willing to go on that journey, and go through those thresholds, and escape the earth's gravity. We have to escape from our comfort zones, and be willing to go where it might be a little bit uncomfortable.

And so, part of coaching, is to support that. People usually come to me and most coaches, I think, with a problem, looking for a solution. And so we start there. We create some value, we help relieve some of the tension. We find some strategies for making the current situation more tolerable, but that's not a very big payoff.

And so when someone experiences some movement from where they've felt stuck, or where they've felt burdened in some way, then the invitation of coaching is, "Well, now let's see what you really want to create, and let's go on an adventure."

What could be possible for you? What do you really dream of? What's your longing?

And so that's the invitation of coaching.

Daniel Stillman:

In a way, I love that you're removing all the next questions I was going to ask, but bleeding into them, which is perfect.

This is one of the reasons why, I think one of your quotes that is one of my favorites is that, "All life coaches aren't executive coaches, but all executive coaches are life coaches."

And the idea that if we're going to create something that we really, really want to bring into the world, if we're going to go into uncertainty, if we're going off the beaten path, if there's really an adventure, we're going to hit some roadblocks.

Robert Ellis:

Yes.

Daniel Stillman:

And the deepest of those roadblocks is, who the hell am I to do this? And that often comes up. So then what is the boundary, because you and I are not therapists?

Robert Ellis:

Right.

Daniel Stillman:

Right. When we are in a coaching relationship, what do you feel like is the right way to approach things like the love threshold, which is always there?

Robert Ellis:

Yes. Well, so the first thing to understand is that, we talked briefly about essence, everyone has a natural way of being in the world that's valuable, without any thought or effort on their part. That's essence.

But we live in a world of form. All of the material things around us, my desk, my computer, it's surrounded by forms, right?

Thoughts are forms too. They're thought forms, our beliefs, our identity, our values, those are also all forms. Coaching is a form. By form, I mean that, we have a certain idea of what coaching is.

It's a kind of conversation that's different from other conversations. It's different, for example, from therapy. Coaching can be therapeutic, but it's not therapy. Therapy is a different form. They're different. There are different boundaries, different agreements about what happens in a conversation with your therapist.

But for me, the only criteria for whether or not I can talk about something with a client, is really two things. Number one is do I have permission? And two, is it helpful?

So the quote that you mentioned, "Not all life coaching is executive coaching, but all executive coaching is life coaching." What that means is I believe that we can't separate who we are personally from who we are professionally, so just because you're an executive, and just because you're coaching someone-

Daniel Stillman:

You can, but there are costs to doing it. Let's speak. Let's speak.

Robert Ellis:

Exactly. There are people who try to do that, but it doesn't work very well, and it's an illusion, I think.

Daniel Stillman:

Why not? Why doesn't it?

Robert Ellis:

You always bring yourself.

Daniel Stillman:

Why is it an illusion? Can you peel back to a little earlier on then?

Robert Ellis:

Oh, it's an illusion, because we're not ChatGPT, we're not robots, we're people. We have feelings, we have blind spots, we have history, we have background, we have beliefs, we have identity, we have values. We are human beings, and we bring that to work whether we believe that or not.

Daniel Stillman:

Yes.

Robert Ellis:

And I think it's actually disastrous if we don't acknowledge that, and don't honor it. And the evidence is, we're surrounded by the evidence of that. If you look at the world, and you see all the problems that we're facing, I think many of them are caused by the fact that we try to separate our humanity from our activity, what we're creating.

So we bring all of us to work, and that's why, if you are an executive coach, and I'm an executive coach, I'm not a life coach, meaning that I don't just work with people who are trying to improve their lives. I work with people who are trying to create things, that have the potential to impact many people.

And so my work is to help them personally.

I work with people who are trying to create something that's so aspirational, it requires a personal transformation. In other words, they're trying to create something that, as they are now, they won't succeed. They need to grow into the possibility of what they're trying to create. So that's how I think about it.

Therapy is different. I'm not a therapist, and if I feel like someone needs therapy, I'll refer them to a therapist, but in the meantime, I may have a conversation with them that may be very therapeutic, and that it can be helpful on a personal level, as well as a professional level.

Daniel Stillman:

Yeah. I'm wondering if we can, this is something that I've, I myself have, I would say, have worked to navigate, to thread the needle in my own coaching between the idea that essence, that everyone has a way of being that is natural and good, that if they can release all the barriers they have, that something will be unleashed, with the growing into.

There is this idea of growing into something more. And I feel like there can be this fundamental tension from, I need to be more, I need to be bigger than, I need to be less than I currently am, I need to tone it down, or be more than I am, with how I am is enough. How do you put those...? Those two things feel intention to me.

Robert Ellis:

So are you asking, how do you navigate when someone comes to you with something that feels too big, or where they're playing too small?

Daniel Stillman:

I think I'm more asking, maybe, more on a meta level of the idea that somebody has an essence, and that means that they are enough. There's also a sense that they want to create something that requires a personal transformation, that they have to grow into something.

Robert Ellis:

Yes. So yes, your essence is enough, but that doesn't mean you can't get better at it. It just means that you, you're good at something, you have something valuable to contribute, and the more you create from that, the easier it is, and the happier you'll be, because you'll be more fulfilled.

Most of us don't think about essence. We tend to discount the things that we're naturally good at. First of all, we're not aware of it, because it comes so easily. We don't pay attention to that.

But yes, if we aspire to something, we may have to grow. A part of growth is becoming more congruent with your essence.

Daniel Stillman:

Yes.

Robert Ellis:

Because, you see, most of us are living and creating from a false persona, which is, I like to think of it as, we're all the solutions to problems that no longer exist. And what I mean by that, is we all have adopted strategies to, again, to navigate life, and to get the attention, and love, and in order to survive. We've adopted strategies that are not authentic, or not congruent with our essence. We've become, to some degree, greater or lesser degree, something that we're not, in order to survive.

So part of growth, is letting go of some of that, and becoming more and more who you are, finding out who you are, and doing that on purpose, creating from that place. But it also is about learning and growing, so we can get better at things that we're already naturally good at, and we may need to learn other things, and we learn and grow as we go on a quest.

Like you said earlier, you can be on a path, or a quest. If you're on a path, you're doing something that you already know how to do. It's fairly predictable, it's not very aspirational or complicated, doesn't require a lot of resource or cooperation.

And so if you're trying to get from A to B, you can just start at B, and reverse engineer it, and it's a project management challenge.

Daniel Stillman:

Yeah.

Robert Ellis:

That's a path.

Leadership is, if you really want to live an adventurous life, you open yourself up to the possibility that the universe knows better than you what you could create, what's possible, and so you go on a quest to find out what's possible. You aim for B, but in this case, B is the best thing that you can imagine, and you conduct experiments, you try different things, and that's how you learn and grow.

Daniel Stillman:

Yeah.

Robert Ellis:

So.

Daniel Stillman:

So.

Robert Ellis:

So.

Daniel Stillman:

Dot, dot, dot.

Robert Ellis:

Does that...?

So that's how I think about it. Growth is, part of growth, is letting go of what doesn't serve you anymore. That's also growth. Part of growth, is learning, and gaining things that you don't already have. That's growth.

And we mostly think of growth in terms of that. How are we going to get bigger? Growth to me is also not necessarily bigger. It's better, more congruent, more resonant, more authentic, more aligned with who I am. The more I create a life that is more resonant, congruent, and aligned, the more fulfilled I am, the happier I am.

Daniel Stillman:

I think that does scratch the surface. So there are a few other layers I want to pull back, and one of them is, how this modality of Coaching from Essence, how you feel it applies throughout an organization.

Because one of the things that comes up in a lot of my coaching work, is an eventual realization of, wow, this is a fundamentally different way of interacting with someone in a conversation to accomplish more than we can imagine, something that's better than can imagine, and many leaders are exhausted from micromanaging, and are not getting the results they want to be getting from their teams.

So I'm curious how you feel, somebody, who isn't a coach, would read Coaching from Essence, and what parts they should be thinking about bringing back to their teams.

Robert Ellis:

So until I write the Book for Leaders, which is the next book that I'm working on, now that Coaching from Essence is published. In fact, I should be getting the proof of the, so the ebook is available now. I think I'm getting the proof of the paperback today, and assuming that it all looks good, I'll hit publish, and it'll be available by the time you post this.

But everything in Coaching from Essence, applies to leaders, or really anyone who wants to create a life they love. Coaching from Essence, is really a loosely connected network of ideas and models, and language for how to create things. That's really all that it is. And everything in the book, with the possible exception of, there's a section called The Red Paperclip, which is about practice building, that will be more of interest to coaches, or consultants, or anyone who is in a service business, and works with clients, but everything else is applicable to leadership.

So we talk about essence. Organizations have essence too. Organizations have, they have a natural way of creating value. Organizations get into trouble when they depart too much from their natural way of creating value, when they try to be something they're not, and that's one of the reasons that most mergers and acquisitions fail, because when you are just motivated by self-interest, status seeking, scarcity, and survival, meaning that you're just trying to make money without any sense of purpose, it's very easy to try to create business, or look for opportunities that have nothing to do with who you are, your core competencies, or anything like that.

So organizations have essence too, and leaders, if Coaching from Essence is a language for creating, what leaders do, is they help people to create things. And like you say, if you don't want to be a micromanager, one of the best things you can do is teach people how to create things.

Another way of thinking about it, this isn't in the Coaching from Essence book, this is what I'm working on in the Leadership Book, is I think of leadership as, most people think of leadership, or entrepreneurship, as sort of climbing the mountain.

Daniel Stillman:

Yeah.

Robert Ellis:

You're constantly overcoming obstacles, and you're climbing the mountain, and eventually you get to the peak where you're going to get to, whatever success it is that you envision.

But really, leadership is about building the mountain underneath you. It's about making, if you're a leader, one of your primary tasks is to make everyone that you work with more valuable. And if you want to grow as a leader, then wherever you are in an organization, and by the way, anyone can be a leader wherever they sit, simply by doing everything they can to make everybody around them more valuable, including themselves.

And so then you think, well, what are the most valuable things that leaders do? What's at the top of the mountain as you move up the mountain, what are you doing more and more and more of?

Well, it really, I think, it boils down to just a handful of things. It's how you think about the future, how you think about impact, systems, strategy, culture, and leadership. And leadership being, how do you do that, how do you help people become more valuable? How do you help people navigate the unknown, on the way to something better than they can imagine?

So that's how I think of leadership, and that's how these ideas can be applied in organizations.

Daniel Stillman:

It's so interesting, because at the core, something my dad used to say, was that, or one of my dad's teachers in truth, but everybody's living their lives according to the precepts of a defunct economist, and every economist has a model of how a person is.

There's this idea of like, oh, we act through self-interest, right? And Adam Smith would say, "Yeah, the whole economy just runs, because it's just all seeking profit, and self-interest." And the idea of how change really happens, and what a person really is, I think is one of the things that's really fundamentally different about your approach, Robert.

Because the idea that everyone has an essence, and it's my job to evoke it, and maybe even provoke it, is very different than the idea that I have to download the correct instructions into everybody in my organization, and build the right matrix, and program them, and it'll just be perfect, and run, if a mechanistic approach, or a computing approach, this is an essence based approach, is a very human approach, and really resonates with one of my perspectives, which is that invitation is the best way to create a change. Not through force, but through somebody wanting to step forward, and that is a very different model for change.

Robert Ellis:

Yes.

Daniel Stillman:

I really haven't thought about, I feel like you've talked about this before in some of our conversations, that organizations can have essence, but it's a profound shift to think, what is the essence here, and how can I evoke it?

Robert Ellis:

Yes, it is a different way of thinking about it. And again, most organizations are very path-like. And by the way, I should, just to be clear here, there's no judgment about this. We are all, both path-like and quest-like. Much of your life is path-like. There should be some parts of your life that are more quest-like, more adventurous, where you're trying new things and learning new things and taking risks. And the same is true for organizations.

Daniel Stillman:

And sometimes, you just want to make tea, and there's a very clear path to making tea.

Robert Ellis:

You just want to make tea, that's great, but then sometimes you want to try something different.

And actually for an organization, organizations, startups are very quest-like, because they don't yet know what works. They're trying experiments. I mean, Lean Startup is a very similar idea. They're trying lots of experiments in order to turn their quest into a path. As you learn, you start turning more and more of your business into a path, so that you can replicate it, and scale it.

But then if you don't continue to have something quest-like, if you're not learning and growing and innovating and disrupting yourself, then eventually, you will lose, because someone will come along, who is more quest-like, and they will improve on whatever it is you're doing, or the market will change, and so you can't rest on your laurels if you're trying to be a successful organization, unless you're doing something that's very much commoditized.

Daniel Stillman:

Who wants to live in that quadrant for very long?

Robert Ellis:

I mean that, it's fine if you do, but I don't think that's very satisfying for most people.

But what you're talking about, yes, many organizations are bureaucratic, they're rigid, there are lots of rules, and policies, and so forth, and as an organization grows, it does need to have a certain amount of that. But that's sort of like, overhead. That kind of overhead, prevents you from being as creative as you can be, so you want to, with all of that, the way I think of it is, you want to have the minimum effective dose. You know, don't want to introduce any more bureaucracy, or policy, or rules than you need to, in order to just prevent chaos.

What you want, is to encourage learning, and growing, and experimentation, and as a leader, nurturing the essence of the people who work with you, so that they're creating the most value with the least amount of effort. And your organization is creating the most value with the least amount of overhead, and distraction.

The other thing, is that we talked about the hidden curriculum, the self-interest, status seeking, scarcity, and survival. Well, what is the antidote to that? I think the anti antidote to that, is essence, abundance, service, and trust.

If you start living your life from essence, what you discover is that you actually have more to offer than you thought. You actually have something of value. You're here to create something that will be helpful.

And really, to me, a meaningful life is, you give yourself away. We're all here to give ourselves away, to express as much of our best selves as we can. And so the more you get in touch with your essence, and the more you're creating from who you are, and again, that's individual, or as an organization, the more you realize how abundant you are, and the more you want to give yourself away, which means you want to serve, you want to create things that are actually meaningful and valuable.

And the trust, is really about trusting that if you do that, the universe will support you. And when I say the universe, I just mean that things will work out, because most of us are afraid to be ourselves, because we're afraid that things won't work out if we don't trust ourselves, or our intuitions, or our natural abilities, or creativity. There's so much pressure to become something we're not. We're being told what we're supposed to do, and if you are trying to create from that, it's very difficult.

Daniel Stillman:

Yes. And I think, one thing that people who are listening to this should, another reason to read the book, trust is one of the thresholds.

Robert Ellis:

That's right.

Daniel Stillman:

Literally, just in a conversation with this morning with one of my clients, laying out the thresholds, and being clear what isn't in the way, and what is still in the way, is really powerful, because I've seen clients get caught at the silliness threshold, or the sanity threshold.

But trust and love are very easy hook points, but not always. Sometimes it is actually, I don't actually know how to do it, and that's fine.

Robert Ellis:

So you're talking about the threshold. Since we're talking about it, just briefly to explain what we mean by that.

The silliness threshold is often the first one that comes up. When I'm talking to someone, and I'm asking them, so when someone comes to me, the first thing that I try to do, is create some value around whatever presenting problem they have.

But then I ask them, "Great, so what would you like to create? So let's say, this wasn't a problem, and you could create anything you wanted. Let's stream together. What would be possible for you? What would you want to create? What are you longing for?" And they'll often tell me some version of, some smaller version of their dream. I think of it as sort of like a bonsai dream.

And nothing against bonsais. I think bonsais are beautiful, but they're beautiful miniature versions of big trees.

Daniel Stillman:

It's just not a redwood.

Robert Ellis:

What's that?

Daniel Stillman:

It's just not, they're not redwoods.

Robert Ellis:

So I want to know, what's the redwood, what's the real dream the person has? Not the dream that their spouse wants, or their parents want for them, or their friends, or their colleagues, or their bosses, or whatever, but what did they actually long for?

Daniel Stillman:

Yeah.

Robert Ellis:

And I often know when I'm getting to the real dream, because they'll tend to laugh, and discount it. That's the silliness threshold.

Daniel Stillman:

Yeah.

Robert Ellis:

It's the fear of embarrassing themselves, or they'll get laughed at, or rejected, or they have a dream that, because it's real, it's a little bit tender. It's something they actually care about, and so they feel a little vulnerable, the more they talk about it. That's the silliness threshold.

So a lot of times, we stop ourselves from doing what we need to do, because we're just afraid to be embarrassed, or what if somebody judges us, or rejects us, or whatever it is.

But then there's the trust threshold... Then there's the knowledge threshold. By the way, these can happen in any order, but often they happen in this order. Then the knowledge threshold, I don't know enough, or I know too much. I can give you all the reasons why something won't work.

Daniel Stillman:

I have to know X, in order to get started with Y.

Robert Ellis:

Everything. And you know my philosophy is, begin before you're ready.

Daniel Stillman:

Yes.

Robert Ellis:

You don't have to know. If you wait until you know everything, you'll never start, because it's impossible to know everything.

Daniel Stillman:

Well, so this is just, if we do do a parenthetical offsite, I wanted to talk about evocation and provocation, probably because I see those as universally applicable leadership skills, not just coaching skills, and that is a provocation to propose to someone, that they can begin before they're ready, is a provocative question.

Robert Ellis:

Yes.

Daniel Stillman:

Right? The questions you're asking when you say, "Well, what's your real dream?" You're trying to evoke a bigger dream from them.

Robert Ellis:

Yes.

Daniel Stillman:

Telling somebody that, that's a bonsai dream, is provocative.

Robert Ellis:

Yes.

Daniel Stillman:

It's a provocation. This is maybe where we go back to, use of self, in the coaching conversation. I'm looking at these two dials of evocation and provocation, and I think it's possible to turn them to 11, and maybe get some noise, some feedback.

Robert Ellis:

Yes.

Daniel Stillman:

That you're pushing someone a little harder, or as our friend Vanessa would say, taking them to your edge, not to their edge.

Robert Ellis:

That's right?

Daniel Stillman:

Which may be your ethos as well.

Robert Ellis:

You want to be careful about, when you're provoking somebody, you want to be careful that you're not doing it out of your need, and you're really being sensitive to where the client is.

So provocation, I'll talk about provocation in a minute, but the way I think of it is, I never push anybody. What I tell people is, "Listen, I'm going to be right with you right here. I'm right behind you. I'm supporting you, and if you stop, I'll bump into you." That's a provocation.

So there are degrees of it. If you think of it as a continuum, one end of the continuum, is what I think of as a disturbing question. I just ask a question that might be a little uncomfortable for somebody. And then a provocation is there's a continuum where it gets a little bit hotter.

And then if you were to graph how much heat you apply, and there's kind of a curve, a disturbing question is low heat, and a real provocation is higher heat, the Y axis is trust.

Daniel Stillman:

Yes.

Robert Ellis:

So if I don't know someone very Well, I won't be very provocative, usually. I might ask a disturbing question.

Daniel Stillman:

High trust, high heat, is, you're still in the safe zone.

Robert Ellis:

High trust, high heat.

Daniel Stillman:

Low trust, high trust.

Robert Ellis:

So when I have trust, that can be a recipe for disaster.

But one of my very intentional aims is to create high trust with my clients. That's critical to doing deep, powerful work as a coach. So I do everything I can to let my clients know that they can trust me, and once I've built trust, then I can be more provocative.

So let's just talk about what we mean by evocation and provocation. Much of coaching, or much of the way that many coaches think of what coaching is, is that it's evocation, right? It's asking good, open-ended questions, using your curiosity, doing active listening, and so forth, and drawing the client out.

Daniel Stillman:

Tell me more about that.

Robert Ellis:

Yeah, tell me more about that.

And based on the idea that the client already is, I forget the phrase, full, and complete, and has all the answers and everything, but I don't really subscribe to that philosophy.

But yes, we're all whole, but you know something I don't know, and I know something you don't know, and so, there's nothing wrong with me giving you some things to think about that you wouldn't, would not otherwise occur to you, and I do that as a coach. Some people call that advice. I don't really think of it as advice, because I can't tell anyone what to do, but I can offer many things, often, valuable and helpful things that someone can think about, and then they can make their own decision.

So a provocation is an invitation. It might be a challenge for someone. It might be a statement of belief, that I believe they're capable of something that they're maybe not sure they're capable of, and so I encourage them to conduct an experiment.

When someone comes to me, and they tell me their dream, my role as a coach is to believe them, and to remember. And so when they forget, I remind them, "Hey, you have this dream, and I believe you. You told me you had this dream, and I believed you. And furthermore, I believe that you're capable of creating, if not that, something better than you can imagine. And so I encourage you to go on that quest, and I encourage you, here's some experiments you could try."

So that's a provocation.

Daniel Stillman:

Yeah.

Robert Ellis:

It's a challenge. It might be a challenge to their beliefs, or their identity, their values, or their idea of what they're capable of.

Daniel Stillman:

Yeah.

Robert Ellis:

Yeah.

Daniel Stillman:

Well, that was a long parenthesis. I think we may have covered the basics of the thresholds, and people, they should just buy the book, and they should just read it.

So I don't want you to have to-

Robert Ellis:

They're all in the book.

Daniel Stillman:

I know you're in the mood to give everything away, Robert.

Robert Ellis:

I do. I never sandbag. I never hold back.

Daniel Stillman:

I think, one thing, that's... Another one of your favorite models that I want to bring into the conversation, because it's connected to the idea of navigating uncertainty, way back in the two beats ago, three beats ago in our conversation when you were talking about leadership as creating something better than we can imagine, and paths versus quests, and getting caught in productization versus trying to create something truly unique.

I feel like this goes to one of your models that I find perennially useful, which is the futurosity continuum. And I was hoping you could sketch, we can sketch it a little bit, but where I find it generally very useful for leaders, owners of businesses, is just the realization of the difference between reactive and proactive, and the difference between strategic and emergent. I feel like reactive to proactive, is maybe the basic practice of realizing like, "Oh, wow, there's more." Of course, when people see the continuum, they go, "God, I'm caught here, and I want to be here," and then realizing that there's more layers to creating what they really want to create.

I'm wondering if we can peel back some layers on why it's important to make time for strategic thinking, and emergent thinking, and how we can never get that time if we're caught up just in reactive and proactive thinking.

Robert Ellis:

Yes, I will try to sketch it out. I mean, the futurosity continuum is a visual model.

Daniel Stillman:

And I'll put an image of it in the...

Robert Ellis:

Okay. Okay.

So, again, if you think of a continuum, right? So the futurosity continuum, and the reason it's called the futurosity continuum, is that, basically, what we're trying to describe is, what is your stance toward time? Are you creating from the past, or are you creating from the future?

Okay, so the continuum goes from the past to the future, and it starts with reactive. Reactive, meaning, something happened already and now you're just reacting to it, and you're putting out fires, or you're just in problem-solving mode. You're just reacting. You're not in control. You're just reacting to things that have already happened, so that it's very much, you're trying to manage the past.

Daniel Stillman:

Which is a really hard thing to do, by the way, given that it's already happened.

Robert Ellis:

It's a hard thing to do, right? Exactly.

So now, you're trying to fix the past, okay? You're a fixer, if you're reacting, or you're proactive.

Proactive is just, so something has happened often enough that you finally catch onto it, and you say, "Okay, let me see if I can avoid that happening again." That's proactive, but if you're reactive or proactive, you're still responding to the past, so you're what I call a fixer. That's a fixer.

After proactive is opportunistic. Once you start to create from the future, in other words, once you start to move towards something you think you want, once you start creating, you will create all kinds of possibilities. Some of which, will be aligned with your quest. They'll be directionally appropriate for what it is you're pursuing, and others that are shiny objects, they're distractions. And this is one of the problems that leaders and entrepreneurs, especially, can fall right to. So, opportunistic, but at least now you're moving toward the future. You're creating possibilities, that didn't exist before, that might lead to something good.

Strategic. The way I define strategic, is you're intentionally setting about creating a future of your own choosing. So you have an idea of what you want, and now you're taking action to create what it is you think you want.

And again, if you're on a quest, you don't know it's possible, but you have an idea of the best thing that you can imagine, so being strategic, is intentionally taking steps to create something, the best thing that you can imagine. Okay.

Then beyond strategic, is emergent, which is, now, you're in conversation with the universe. In other words, you're paying attention to what results you're getting, what response you're getting, and so you have to pay attention to weak signals. You're noticing just what's showing up for you, and you're seeing whether or not some of these things, whether or not you're creating possibilities now, that are potentially better than you might have entertained before.

Daniel Stillman:

Yeah.

Robert Ellis:

So the difference between emergent and opportunistic, is that opportunistic is kind of random, and emergent is things are responding to what you're putting out. You're more intentional.

I'll give you an example of that. Coaching from Essence. For me to train coaches was entirely an emergent phenomenon. I never had any intention of training coaches.

I was very happy as an executive coach, and I was very much working on creating myself as a powerful executive coach, and what happened was, I was meeting with some success, and I had a lot of friends who were coaches, and so word got out, and people started asking to meet me for coffee, or lunch, or whatever, because they were either thinking about becoming coaches, or they were coaches, and they weren't very happy with the work they were doing, or they weren't creating the success in their practices that they wanted, and so they wanted to pick my brain.

And so after a few people did that, I thought, "Wow, this is really interesting. This just sort of happened out of nowhere. Maybe I should offer something for coaches."

And I had no idea what that offer would be, but I just posted something on Facebook, and within two days, 21 people signed up for training that didn't exist. See, I began before I was ready.

Daniel Stillman:

You did, and I think there was also some essence there, too, right? There was a hunger to connect.

Robert Ellis:

Yeah.

Daniel Stillman:

You weren't just blindly following signals. It wasn't just opportunistic.

Robert Ellis:

No, no.

Daniel Stillman:

This is-

Yeah, sorry, go ahead.

Robert Ellis:

Well, yes, I mean, I had an idea of my essence, and I had an idea of all the things that I was learning, and I had been developing some of those ideas, and teaching many of these ideas to leaders at Singularity University. I developed and led the leadership track for the Global Startup Program at Singularity University, and some of these ideas were sort of road tested there, but I never had any idea of teaching coaches.

So that was very much emergent.

Now, if you can visualize that continuum, again, that's the X axis, the Y axis is time, energy, and resources. So most people, and most organizations, if you were to plot the curve, it's very high on the reactive, end of the continuum, and very low on the emergent end of the continuum. In other words, most of us, and most organizations, are devoting a lot of their time, energy, and resources being either reactive or proactive.

Daniel Stillman:

Yeah.

Robert Ellis:

They're firefighting, putting out fires, solving problems, and relatively less and less time being opportunistic, strategic, or emergent.

The ideal curve, is probably the reverse. You will always be spending some time being reactive, because we can't always predict the future. There will be problems that we didn't anticipate, and we'll have to respond to those, but ideally, the curve would go the other way, where you're spending more of your time and energy being strategic and emergent. You're intentionally, creating possibilities for yourself.

Most startups, it looks probably more like a bell curve, because they're nothing to react to, since they're just starting. Things aren't emerging yet, because they haven't created anything, so they're being proactive and strategic. They have ideas, and they're conducting experiments, and so most of their time, energy, and resources, goes into just conducting experiments.

Daniel Stillman:

I'll put a sketch of this in the show notes for people to look at while we're talking about this.

Robert Ellis:

Sure.

Daniel Stillman:

I feel like there's never been a time when I haven't drawn the futurosity continuum for somebody, where I don't feel like anybody has the optimal distribution, generally speaking.

Robert Ellis:

Sure, and it's changing all the time. It's always changing.

One of the universal challenges as an executive coach, is that if you're working with leaders, one of the things they're always having to negotiate, is how much their time, energy, and resources being sucked toward the fixer-end of the continuum.

They have a vision for the future, and they're trying to create it, but they're often being pulled for the other end of the continuum, and they're starved for the time, and energy, and resources for creating.

Daniel Stillman:

Yeah.

Robert Ellis:

And so, that is something that we do problem solve around.

Daniel Stillman:

So this is, to go back to one thing you said, and I can't believe we're... The time goes really fast, it's crazy.

The idea that strategic intent, is speaking to the universe, and the emergent space, and the continuum, is listening to what's really going on.

Robert Ellis:

Yes.

Daniel Stillman:

And I think people, the first version of this diagram that you made, didn't have emergent, because strategic, for many executives, feels like this is the pen, this is the ultimate goal, is to be strategic.

Robert Ellis:

That's right.

Daniel Stillman:

But of course, being strategic, means also finding out whether or not the strategy is working, and what the universe really wants of us.

Robert Ellis:

That's right.

Daniel Stillman:

So this idea of speaking to the universe, and listening to the universe, is just, I would love for you to stay a little bit more about that.

Robert Ellis:

Well, yeah. I mean, think about strategy, and strategic planning, the idea of strategic planning is just an interesting one. Let's just say, right?

Daniel Stillman:

Do you want to have one more word? What's the word you really want to use, Robert?

Robert Ellis:

You have an idea of what you want to create, and you're saying what you want to create, so it's a monologue, in a way.

You're saying, "Look, here's the plan, here's what we want it, and here's the plan, here's how we're going to create it." And that's very path thinking.

Now, it can be strategic to do premortem, right? To say, "Okay, we're aiming for this." By the way, I'm not a big believer in OKRs, or things like that, because in my experience, every client I know who uses OKRs, they're so prone to, first of all, to identifying the wrong OKRs, for example, common one might be, how many customers we're going to get.

My point of view is you should just optimize for one customer, or you identify who your customers are, and optimize for each of those different kinds of customers, or those personas.

How many you get, you don't know. You don't know what's possible, so it's not very meaningful to think that, picking a number out of a hat, is going to really inform your action.

So you aim for something, you have a strategy, you have an idea of what you want to create, and you put that out, you ask for that, in a way, but then you have to listen, and learn, and see what response you get, and that's emergent.

So when you are moving toward emergent, you're entering into a conversation, which means that, yes, you have an idea of what you want to create, and you take action based on what you think is possible, but you're very much open to learning, and listening, and observing, and seeing what you get in response, so that you might discover something else that's possible.

That's how you get to something better than you can imagine. That's one of the ways.

Daniel Stillman:

Yeah.

Robert Ellis:

My favorite way is to optimize for serendipity, but-

Daniel Stillman:

That's another conversation.

Speaking of which, I've used up all of the time we have allotted to this conversation.

Robert Ellis:

Oh, no.

Daniel Stillman:

What haven't I... If you can go one more moment, because we're literally on the wire, and I want to respect your calendar, Robert.

Robert Ellis:

Sure.

Daniel Stillman:

What haven't we talked about, that we should talk about. What is the question that I have not asked you, that I ought to have asked?

Robert Ellis:

You haven't asked me, why? Well, we did touch on it. The why. Why is this important? What is this about? Is it about just being more successful, or making more money, or something like that? And we did touch on it.

Obviously, we don't have time to, say, go into the Hero's Journey, but that's such a popular model that so many people talk about, in terms of leadership, and so forth, and I think many people misunderstand what the Hero's Journey is really all about.

The Hero's Journey, is not an individual journey of overcoming obstacles in order to get some boon to elevate yourself. It's not about self aggrandizement. The whole reason for the Hero's Journey, is to get something that is of benefit to the community.

And that's really how I think about essence. Essence is not about becoming yourself, so that you can just entertain yourself and be content. The journey to getting in touch with your essence, and creating a life from your essence, is so that you're giving yourself away. You're sharing your best self with the world, and think about how different the world would be if everybody did that.

So that's really what this work is about. That's what it's about as a leader, and building the mountain, how can you elevate everyone else around you? How can you create a venture that creates value for the world, so that you're doing something meaningful that actually improves the world? That's what interests me.

Daniel Stillman:

Yeah. I think a world where everyone can express their essence, building organizations where people can express their essence, designing meetings, gatherings, spaces where that can happen, is a transformative, that's not a path, that's definitely a quest, and I think it's a worthwhile transformation.

Robert Ellis:

that's right. And as you know, connection is so important, and you're so good at creating connection, facilitating connection, and connection happens through conversations. When we can talk about things that matter, then we can connect at a different level, and we have an opportunity to express more of our best selves, and so, that's why conversations, and facilitation, and coaching, I think, are so important.

Daniel Stillman:

Well, Robert, where should people go to learn about all things, Robert Ellis, to find more about your work, and to find copies of not just this book, but-

Robert Ellis:

Yes.

Daniel Stillman:

The sequels.

Robert Ellis:

Coaching from Essence is now available on Amazon. It was written for coaches, but really, if you're a leader, or an entrepreneur, or you just want to create a life you love, there will be something in the book that will speak to you.

I am working on the Book for Leaders. That'll be next. I'm hoping to have that out by the end of this year.

If you want to know more about my work as an executive coach, you can go to futurosity.com. If you want to learn more about Coaching from Essence, if you're a coach, go to coachingfromessence.com.

And by the way, I should mention that, giving myself away, I have given the entire Coaching from Essence Program away. In fact, I've given three complete programs away that were recorded on Zoom. You can go to Coaching from Essence, and join the Coaching from Essence community, completely free, and you can watch over 100 hours of videos of the entire course, masterclass, client creations, sprints, and connect with a community of over, I think it's around, 400 extraordinary coaches now, so it's all completely free.

Daniel Stillman:

Yeah, you could spend weeks absorbing it, or you could just read the book, which is very handily dandily packaged up.

Robert Ellis:

Or you could read the book.

Daniel Stillman:

Yeah, it's like spending a really nice afternoon with you.

Robert Ellis:

Yeah, I wrote the book, so that you could have it in your hand, but the entire course is available for free. I think the world needs more coaches. I'm trying to facilitate that.

Daniel Stillman:

Well, at every level, in every organization.

Robert Ellis:

Yeah, yes.

Daniel Stillman:

I think.

Robert, you've been exceedingly generous to me with your time today. I love the book. Reading the book, was obviously like taking a warm bath, because I've been exposed to your thinking, and I've been in conversation with you for several years now, but I still loved and enjoyed the book, so I'm really grateful that you made it real. Thank you.

Robert Ellis:

Thank you. I appreciate that.

Daniel Stillman:

Well, I will call scene.

How to Think Strategically about Funding for Founders and Investors

I first met Avantika Daing, a General Partner & Managing Partner at Plum Alley Investments (and Tedx Speaker!) while she was onstage at an Entrepreneurs Roundtable Accelerator event. She was there to share a bit about Plum Alley’s Investment thesis as well as unpack six pitches live from early-stage companies.

Let’s level set a bit so you understand Avantika’s and Plum Alley’s mission, which revolves around an important number that hasn’t moved much in years, despite a lot of effort - 2%. 

According to Pitchbook, in 2022, companies founded solely by women garnered just 2% of the total capital invested in VC-backed startups in the United States. Plum Alley only funds gender-diverse companies and works to create an ecosystem to help them not just get funded, but to grow and succeed. That’s one of the reasons I wanted to bring Avantika on, to share some of her ways of thinking strategically about funding as an investor, how Plum Alley is working to create a more sustainable funding ecosystem for diverse founding teams, and how she coaches founders to be more strategic about funding, too.

Watching Avantika on stage peel back the layers of the onion (one of her favorite metaphors!) on a company’s story in conversation with a founder and work to understand the company’s potential was fascinating - it’s a tremendous act of intellectual rigor and curiosity. Her questions also reminded me that founders can make an investor’s job a lot easier through more powerful and intentional storytelling.

Another powerful metaphor that Avantika came back to in a number of pitches was the idea of a Basecamp.

In other words, Avantika, as a funder, wants to know: Is your company building a core technology or defensible market position (a basecamp) that will provide you with multiple paths to success? 

Avantika acknowledged that a “single story” about how your company will “win” or “summit the mountain” is powerful, but she was clear that she prefers companies that are creating a powerful “basecamp”...why? Because:

🏒A “many shots on goal” strategy can help create longevity and increase options for success.

I’m so grateful that she was willing to have a longer conversation with me on the record to explain her ideals about storytelling and the basecamp-summit metaphor.

She also helped peel back some layers on another idea she loves to coach founders on: “Dressing their cap table” for sustainable success from seed to IPO and well beyond - since capital needs don’t stop at IPO.

I love how Avantika’s metaphors shift, refocus and redesign the conversation about pitching, funding and sustainable success for startups.

Enjoy this conversation as much as I did!

Links, Quotes, Notes, and Resources

Plum Alley

Avantika's Tedx Talk: There is No Balance. There is Juggling

Daniel’s LI post on Avantika’s Entrepreur’s Roundtable Session, highlighting key questions and perspectives from Avantika, including the “base camp/summit” metaphor.

Summary

4:10 Data shows that less than 2% of companies that went public over the last five years were female founded

7:02 Plum Alley’s Venture platform will provide portfolio support, plug into investment world, and move the needle for diverse entrepreneurs, investors, and institutions

19:36 Avantika explains her concept of "Dressing the Captable" which involves strategically thinking through who to give equity to and who not to give it to, in order to set up a company for success

25:26 Thinking about the long-term arc of a conversation when it comes to venture capital

29:35 Avantika proposes a platform approach where the best investments stay within the platform and create the highest level of investor returns

Key Quotes

Minute 2

Avantika Daing:

So the number that's been existing in the VC world is about the percent of venture capital funding that goes to female founders. That is the 2% number that has been historically referred to. What we did at Plum Alley, and this is partly leaning on my two-and-a-half plus years of operating experience, plus having taken a company public, directly being responsible for two IPOs, indirectly being responsible for another IPO. What we're looking to do is look at the IPO landscape, and work backwards. And the why behind that is about disrupting wealth realization. It's a word we made up, and what wealth realization really means is wealth creation, and then distribution. Wealth is often created by generational wealth, so you're born into it.

Or the other alternative is to have a technology company take placement in the IPO market. So those two are usually the trajectories. Not the only, but usually the trajectories for wealth creation. What we are looking at is taking that further, into wealth realization, and really changing the face of IPOs. So the 2% number you mentioned is important, but it's a new narrative, and that 2% number to be very specific reflects the 1100 plus new IPOs over the last five years that occurred on New York Stock Exchange and Nasdaq, where only 2% of that, female founded IPOs.

So if you look at it from moving backwards in what needs to be done, we realize very quickly that the needle hasn't been moved, and there's some very ingrained systemic biases that exist that need to be changed from the perspective of wealth realization, to really move the needle on redistribution of capital on any aspect or spectrum of diversity.

Minute 18

Avantika Daing:

I'll just quickly plug in. About 70% to 80% of female founded companies, specifically, exit through an M&A route over an IPO. And I have a whole theory about that which is, look, none of it's easy. So, anyone, congratulations to anyone who can take it to an M&A stage. But the stakes and the motivations are not aligned. And so, bankers and founders are motivated to take the nearest, quickest exit, versus having the right mental capital infrastructure, platform support for taking it further for a handful more of years. Somewhere between two, five and 10. It's not easy to staying on that IPO route, and that's the needle we need to move

Minute 52

Avantika Daing:

I would probably say the two things are learn to say no to your customers, as well as investors, to be hardball on your strategy.

And there are two different types of strategy when you're ... One is focused on revenue. If you are a multi-year SaaS contract with a hardware component build in, and you've got customers saying, "Well, I'm not sure I want to pay for three years. I want to do a pilot for six months, and I don't want to pay you, and then I'll scale up, and then I'll do a contract for one year." You got to walk away from that. There are ways in which you can accommodate that, but you cannot be creating exceptions, especially early on. It's a flip of mindset, and it's nerve wrecking to think ... Most people think early on, "Oh yes, I've got a great enterprise. Logo, top 500 public company coming, why would I want to keel over?" Well, you need to set precedents, and you need to set the right precedents. You have to be a bit strategic.

I'm not saying you shouldn't accommodate for those asks, but be strategic in how you create that construct. So, for a pilot, you build a pilot in. If they like the word, "Pilot," you give them pilot, but you make it monetizable. If they want to backhand, you have to understand, again, peeling the onion back, understanding where their motivation is. And the motivation there is, large enterprises like to say, "We want to first test you, and then backend payment." How do you build that into a construct of establishing your contract, and the nuances that go into the contract that set you up for monetization.

There's a component of learning to say, "No," with a creative element of accommodation. And then the second part of, "No," is to your investors. Early investors ask for side letters. They ask for preferences. You want to set yourself up for success for later rounds, and you want to be conscious of what construct and precedents you're setting with your investors now. And having conviction and motivation on yourself in not reducing your valuation, or not wanting to give up too much ownership, whatever it might be for you as a founder or founding team, sticking with your narrative is extremely important.

Minute 56

Avantika Daing:

And then, the last thing I'll say is very important. It's not done enough, and it's completely underestimated, which is think two steps ahead. Also, a different version of peeling back the onion. But if you're raising seed, think about Series As and Bs. If you're raising As, think about Bs and Cs, and why? Look at the market today.

Some of our portfolios that we've worked very closely with when they were raising the Series A, we very quickly came in and we said, "Now is the time to bring in non-dilutive capital. Meet, they're friends of ours, X, Y, and Z that are interested in funding you. Giving you a line of credit, giving you a debt vehicle if you're a Series B," bring that in. Unfortunately, you're not thinking that, because you don't have a need for it. [inaudible 00:56:58] Founders would say, "Well, I have a runway of 18 to 24 months, why do I need to think about that? I've got to runway for 36 months. Why do I have to think about it?"

"Yeah, great. I'll take the introduction, but I'm really not going to lean in. I'm too busy now trying to close my [inaudible 00:57:14] later." Well, later becomes too late, because you cannot time a situational market. And a situational market for us is a COVID. A [inaudible 00:57:25] for us is consideration towards a down market. And so, to manage situational markets, when you are doing your equity round at the back of it is the time to come in and put creative financing vehicles in place. You may never need it. You may end up paying a bit, which could be the downside. But frankly, you're never going to lose out on using, and having that as a backup in creating financial health. And really, frankly, drawing that back to your own mental health in using it as a tapping mechanism.

More About Avantika

Avantika Daing spearheads Plum Alley’s strategy and investments towards deep tech and novel science companies with gender diverse founding teams. Plum Alley has raised over $60 million across 30 companies including Mammoth Biosciences, Einride, Air Protein, AiFi, Diligent Robotics, One Concern, Shine and Biobot Analytics. The Portfolio boasts of two unicorns and one exit. Plum Alley offers LPs and individual investors the opportunity to invest in diverse early stage private companies that are transforming the world.

Avantika brings proven leadership across business functions, operations, and executive management for both start-ups and Fortune 1000 companies. She has a unique combination of an institutional grade reputation with a grassroots approach to building enterprise software, customer focused GTM, and platform businesses.

Avantika’s experience in private and public companies covers the healthcare and technology sectors. Her professional experience spans nearly 30 years, as both an executive and a founder, with responsibility in management, product development, business development, operations, M&A and IPO. Prior to PA, she was the Chief Revenue Officer at Jopwell, Andreessen-Horowitz backed. She served as the Chief Growth Officer at Zomato/UrbanSpoon, Temasek, Sequoia, and ANT Financial funded, which grew to $1.3 Billion in valuation during her leadership. She also founded a venture-backed, international SaaS marketplace. Avantika was the first commercial employee at Eyetech Pharmaceuticals, where she helped grow the company to IPO (NASDAQ) at a $735M market capitalization in 3 years.

Avantika is a TedX speaker and speaks on Venture Growth and Entrepreneurship, Investing in Female Founders, IPO, and Intentional Investing. Avantika currently is on the Board of TiE, New York.

FUll Transcript

Daniel: Well, welcome to the Conversation Factory. I hope we can have a good talk as the title of my book goes. Listen, I was really excited to host this conversation with you. Partly because that experience at the ERA Round Table when they did that process for the final pitch, where everyone stood up who wanted to pitch a company, and you could ask a question of any of the group to sort of filter out. No crypto exchanges. And the statement you said is, "If you do not have a diverse founding team, if you do not have a female on your team, sit down."

I got goosebumps. I still get goosebumps thinking about it, because it's such a powerful statement. I want to just start there, because of the number 2%. It's a really important number, 2% of female founders of all of ... In the VC IPO exits, and regardless of all of the efforts that people have been putting in over the last years, that number hasn't moved a lot. Can we just start there, and say why is it important to move that number, what's been done and what aren't we doing that we ought to be doing to shift that number?

Avantika Daing:

Well, let me start by first saying thank you Daniel for having me here, and giving me the time and the airspace, if you will, for having this conversation with you. I will say my engagements with you are very exemplifying of your topic, of your book, of a good talk. I'm really looking forward to-

Daniel Stillman:

Thank you.

Avantika Daing:

... the hour here. I'm sure we're going to be jumping around on many different topics, but excited to at least bring to the surface some of the questions that the world at large should be asking, but more specifically certain industries, such as the venture capital industry, the entrepreneurship industry, the ecosystem at large, towards supporting entrepreneurs. Thank you for picking that up. That wasn't orchestrated. It just kind of came out, and it came out very naturally, and I didn't overthink it because of what we do. And so I'm going to start there.

I'm one of two founding partners of Plum Alley Growth Venture, where we focus on investing in frontier technology. More specifically deep tech and novel science. So far our stage focus has been Series As and some Bs, and I'll get into why we've been conscious about coming in at Series A, versus either before or after. Our investment thesis, in addition to being focused on sector and stage, is wrapped in a gender mandate. I say wrapped in a gender mandate, because we don't start there. We look for gender diverse teams after we've identified that there's a sector, an industry, a company we want to invest in, a founder we want to invest in. And after we've done our diligence for a Series A company where we can see the line of sight of initial revenues having a trajectory towards scale and growth. And so, our thesis is very specific in our thesis of investing in frontier tech, supporting gender diverse founders.

We also do ourselves a favor as pickers, as VCs, investing in early stage companies in cutting out the noise. And by [inaudible 00:04:55] I mean cutting out, seeing too many investment opportunities, trying to find that needle in a haystack. But also, cutting out the noise if you will, with complete due respect to all my friends who've participated in elevating the narrative around diversity at large. Be it driven through ethnicity or gender, is cutting out the noise of where the rubber meets the road. And if I can take another quick minute to just explain what I mean about that?

Daniel Stillman:

Yeah, totally.

Avantika Daing:

We've been, and being very analytical in my upbringing and in my career of 25 years prior as an operator, plus converting into venture for the last six years in a professional manner, we've seen a lot of support and narrative. More now in the last three, four years, than ever before on diversity at large.

And that narrative comes from a complete shift in our society, supported by COVID, BLM, MeToo, a handful of other, I would refer to them as platelet shifts in our societal thinking. The new generation, I've got two kids that sit in it. They completely challenge traditional thinking, but it's also been supported by capital. You've got large banks, you've got large institutions who are putting somewhere between half a billion to a billion at work on a diversity thesis. You've got folks like us in VC at Plum Alley. But also others that have different ranges, and sort of USPs, their uniqueness in why they support gender, or diversity, or ethnic diversity at large for investing. So, a lot of capital, a lot of support, a lot of social fabric reconstitution happening in our society. However, when you look at the data over the last 10 years, and we slice the data over a 100-year period, over a five-year period, and then over a two-year period to understand if there are any sort of blips, peaks and troughs that would also tell a separate story.

And if we look at the data over the last 10 years, it's really sad to say that we haven't been able to move the needle. And I'm saying the collective, "We," right?

Daniel Stillman:

Yeah.

Avantika Daing:

And so, it begs the question which is, well, what's been happening? Because there's been a lot of energy, a lot of support, a lot of capital. And I think on the capital front it's easier to talk to, because data is data, is very binary. We're seeing that there is a good amount of distribution. At least in the venture space, of capital in early stage. And by early stage, I mean pre-seed and seed, going to gender diverse founders. So about roughly 23% of venture over the last two years goes to gender diverse founders. We've got data over five years and 10 years, two years is the best looking data, which is why I'm sharing it here.

But unfortunately, as you look up the value chain, as they say in VC, which means Series A, Bs, and later stage getting to liquidity and IPO, where wealth realization, wealth creation really happens, we see that number being halved and further reduced, right. So, in that 2% number you mentioned, it's important to clarify that there's a narrative that's been existing in the VC world for a long time now, which they do refer to the 2% number, but it's a different 2% number.

So the number that's been existing in the VC world is about the percent of venture capital funding that goes to female founders. That is the 2% number that has been historically referred to. What we did at Plum Alley, and this is partly leaning on my two-and-a-half plus years of operating experience, plus having taken a company public, directly being responsible for two IPOs, indirectly being responsible for another IPO. What we're looking to do is look at the IPO landscape, and work backwards. And the why behind that is about disrupting wealth realization. It's a word we made up, and what wealth realization really means is wealth creation, and then distribution. Wealth is often created by generational wealth, so you're born into it.

Or the other alternative is to have a technology company take placement in the IPO market. So those two are usually the trajectories. Not the only, but usually the trajectories for wealth creation. What we are looking at is taking that further, into wealth realization, and really changing the face of IPOs. So the 2% number you mentioned is important, but it's a new narrative, and that 2% number to be very specific reflects the 1100 plus new IPOs over the last five years that occurred on New York Stock Exchange and Nasdaq, where only 2% of that, female founded IPOs.

So if you look at it from moving backwards in what needs to be done, we realize very quickly that the needle hasn't been moved, and there's some very ingrained systemic biases that exist that need to be changed from the perspective of wealth realization, to really move the needle on redistribution of capital on any aspect or spectrum of diversity. Sorry, that was more than you asked for, but I just-

Daniel Stillman:

No, that's the big picture, and I want to go into the leaky bucket. So two things that I was thinking about is, one is, is the falloff rate from seed to IPO higher for females? Or in diverse teams, are they not accessing capital later on in their cycle at a worser rate than male founders? Is that what you're also saying, is that the decay rate from seed to IPO is faster. And so, this is why when you talk about intentional investing, and thinking about a platform approach so that the bucket isn't leaky, that we're actually getting people from seed to IPO successfully across the whole lifecycle. Is that right?

Avantika Daing:

You're absolutely right, and I've heard the argument now in my current role as a VC over the six years, but also in my role of being an entrepreneur, and also in my role of being an early [inaudible 00:12:44] of a very large biotech and technology startup that IPOed each for a billion, and then double-digit billions. Where it's the wrong question to be asking, and the wrong question to be asking is, is there enough supply? Do we have enough high quality, diverse founded teams to be investing in at late stage? For private equity to be involved, for venture capital to be involved, for investors that look for a higher liquidity profile Series B and beyond to be involved?

And I think it's the wrong question, because I don't believe that, that is the stopgap, or the bottleneck. If you look at, and I don't want to spend too much time because that could be a topic by itself, but if you look at where the talent pipeline begins, the talent pipeline begins, especially in frontier tech investing, which is a sliver of all of tech.

It begins at the education level. It begins in undergrad, in masters. If you look at the percentage of students that have female students, excuse me, going into STEM. Be it medical fields, bio-engineering fields, genetic fields, pure engineering, new age, new materials, applied materials, and kind of new age degrees, if you will, that are relatively new opportunities that didn't exist about 10 years ago. We're seeing an influx of talent, and that talent [inaudible 00:14:23] ranges from 30, 35%, all the way up to 50%, right?

If the talent pool is strong, and the startup community is strong, then rethink the question you're asking. They're inherent biases. Private equity looks like a certain type. Venture capital that does late-stage venture capital looks like a certain type. They sure don't look like me. They short on sound like me, right?

Daniel Stillman:

Yes.

Avantika Daing:

And I would encourage everyone to look at my LinkedIn to see what I look like. But I'm a woman of color, that is a first generation immigrant, that had to earn my stripes, was not fortunate to go to tier one ivy-league schools, at least for undergrad. Got the opportunity to do it for postgrad. And so, my story is not very linear. And [inaudible 00:15:16] speak for the best founders out there. It doesn't have to be ... We've invested in MIT startup founders. We've invested in Nobel Laureate founders. We run the gamut, right? The point to be made is that where we come from, we're not born with the systemic biases by default, of me and my partner looking very different, coming from different continents, having different experience.

She's a Wall Street queen, having spent three decades there. I'm an operator, so we bring diverse experiences to the table, and we don't bring those systemic biases. Our thought process is different, which means that our [inaudible 00:16:11] is going to be different. Now, one can argue that we bring different sets of biases.

Daniel Stillman:

Sure.

Avantika Daing:

And yes, that's true. You need those to balance out the systemic biases that exist. When you talk about the leaky bucket syndrome, you are absolutely right. I think we're seeing a good amount of energized funding in venture, supporting diverse founders at early stage. Even at Series A, [inaudible 00:16:35] we see a very marked decline when it comes to Series B. And then, we continue to see that decline to half its rate and beyond as we look at Series C, and later stage.

We really, it's not just we need to, we have to, because if you think about it from an economic viability perspective, as an economist would, the economy is not set up at a fundamental level for sustainability. You mentioned platform, and I'm going to come to that. And what we mean by that is that there is no product out there, AKA, a platform, that can support the lifecycle needs of diversity at scale as diverse founders go through the different lifecycle needs of capital from early to late. [inaudible 00:17:34] beyond capital, finding the right partners for support pre-IPO. It doesn't matter, we kind of refer to it as a ecosystem support.

It varies. The type of services, consultation, business development, capital that you need from stage one, to stage two, to stage three [inaudible 00:17:55] vary. And so, the idea is to create a product, a platform that supports that, that eliminates and prevents the leaky bucket syndrome that happens in venture. But in that, also creates a fabric for setting up economic viability, because if you play the platform forward, and you provide the right kind of capital construct, but also ecosystem support construct, then these founders, diverse founders that actually are able to IPO and prevent the shortcut into M&A, are able to create wealth and then pump that back into the platform. Thereby, creating a cyclical cycle of wealth realization.

I'll just quickly plug in. About 70% to 80% of female founded companies, specifically, exit through an M&A route over an IPO. And I have a whole theory about that which is, look, none of it's easy. So, anyone, congratulations to anyone who can take it to an M&A stage. But the stakes and the motivations are not aligned. And so, bankers and founders are motivated to take the nearest, quickest exit, versus having the right mental capital infrastructure, platform support for taking it further for a handful more of years. Somewhere between two, five and 10. It's not easy to staying on that IPO route, and that's the needle we need to move-

Daniel Stillman:

But the payoff is huge, if they can-

Avantika Daing:

Payoff is huge.

Daniel Stillman:

If they can strap in for a little bit more of that. There's so many layers here that I want to peel back, and I want to think about what messages founders need to hear at what time. I want to put this all in the context of conversation, because that's my ax to grind. Certain VCs only want to be having certain types of conversations. "When you're at this stage, come talk to us. When you have this, come talk to us." And after that stage, or before that stage, there's no conversation to be had. What you're talking about is pulling back and saying, "We want to be able to continuously be in dialogue with you across the whole process, to the finish line." But then also beyond. That's in our last conversation we talked about. Even after IPO, how do they learn to grow their company?

That's what I'm thinking about is what a founding team needs to know to learn to be hearing what's easy or hard for them to hear at each one of those stages. That a platform would be saying in their ear, "Now you're ready for this. Now you're ready for that." Where do you feel like the dips are in that process that a platform can deliver the right messages to them? One I just heard is, "Wait a little longer. We can get you through this period to the next stage," and that sounds like a really powerful message. What else do they need to hear that they are not getting as without a coherent platform set of messages?

Avantika Daing:

Before, Daniel, I answer your question, I just want to say two things on the topic of conversations. All good VCs have conversations. They actually start having conversations with potential ... With entrepreneurs and potential investments early. All good VCs are in the business of having conversations early. The second thing I'll say, it's actually a good thing for VCs to have an investment thesis that's specific, right, because you really need to focus on portfolio construction to drive portfolio returns, to then focus on investor returns. All of that is very important, because your track record in terms of investor returns, it gives you the power and the stage to stand on to keep doing it over and over again. And more of what you need to do. Whether it's venture straight up, or to disrupt venture in some shape or form. So I think-

Daniel Stillman:

Actually, can we hold back to that one for one second? Because when you talked about the conversational skill of an investor, I was floored, and I'm continued to be floored. I went to ... The month before you went my friend Sim Blaustein from Bertelsmann-

Avantika Daing:

[inaudible 00:22:55].

Daniel Stillman:

So standing on stage ... We're sitting on stage, which I know you didn't want to do, and having a series of pitches, of varying quality. And then, asking really, really insightful questions to peel back the onion, and to get what's really going on, I think is a phenomenal conversational skill. I don't know how you ... I mean, that was an-hour-and-a-half of ... It's like watching a symphony. Really, the ability to consistently find the nugget, to ask the right question. I mean, I don't know if there's even a question. It's more of a-

Avantika Daing:

I had a ... Thank you.

Daniel Stillman:

Bravo.

Avantika Daing:

Thank you for that compliment, I appreciate it. I had, and I say this to kind of show my own naivety of not having grown up here, which is as I came off that stage, I had a wonderful gentleman present himself to me, to congratulate. He made the comment that I presented as an oracle. In my head I was thinking, "Is that a compliment, or what is an oracle?"

Daniel Stillman:

Yeah, it is.

Avantika Daing:

And so, I called Deborah, my partner, and I said, "Deborah, I just got called an Oracle. What does that mean?" And she's like, "It's a good thing, please don't be worried." And she mentioned the notion in this culture being called the Oracle of Omaha, and I was like, "Wow, if even one person could appreciate what we bring to the table in the jobs we do, in that manner ..." I was very touched, and very humbled. You mentioned peeling back the onion. I say that to my team. I say that to founders. I'm constantly throwing that cliche, and jargon, and maybe it's a cultural thing, and I need to come up with a better-

Daniel Stillman:

Onions are a very important-

Avantika Daing:

Visual, right? Being Indian, it's a core thing, and everything we eat and do along with turmeric. But peeling back the onion is very important. Now the reason, going back to your point about having [inaudible 00:25:05]-

Daniel Stillman:

What is important about peeling back the onion for you? What is it? Because it's not just jargon, it actually means something to you, right?

Avantika Daing:

It does. I think what it means for us is two things. One is that we can actually have conversations for four years before we come in and we invest. We don't have a thesis that we have to know you like some other institutions out there, for a period of 18 months or two years. We don't have a rule book, or rules towards that. But it so happens, if I can just deviate real quick.

In our portfolio, now 30 companies having deployed over 85 million with a portion of our fund of 25 million, we're coming in relatively soon to having putting a hundred million plus in the market towards our investment thesis. And a portfolio of 30 plus companies, majority of our investments it's just so happened pure serendipity, not orchestrated or planned, that we've known the founders, the co-founding team for a period of 18 months, I think, is the shortest. To about four years is the longest. And the reasons why we've held those relationships, a lot of it has been working very closely.

Some of it has been fairly superficial. Kind of waiting, knowing we needed to come in, but waiting for the right moment so that the portfolio construction ... To your point about, "Come speak to us when you're ready to fit our mandate over a certain stage," being Series A as a starter investor. Part of peeling back the onion is really giving us the ability and the platform in a different way. Not the way that we referred to earlier, to constantly have these conversations with founders, and technologies, and products that we'd like to support via capital.

And so, over time, part of peeling back the onion means you start with a very early conversation, but then as you go through time, or as you go through the depth of your investment analysis, your diligence process, you should go deeper and deeper. That's one part of the meaning of peeling back the onion. The other part of peeling back the onion really goes to something that our investment committee looks at, which is as the founder, the entrepreneur peels back the onion towards their technology, and what they're solving for, how does that go from base camp to summit, right?

Daniel Stillman:

I'm so glad getting to this. I definitely wanted to connect these two ideas. This is perfect. I think it's such an amazing analogy, because you need that when you're talking about a core technology. Because that's part of your thesis, right? Is that you want to find what is at the center of the onion.

Avantika Daing:

Right, and the center of the onion could be the base camp. Could be something very binary that may not excite venture capital at large, but still has a multi-billion dollar TAM. But as you go from the base camp to the summit, and you layer in all the additional value-adds as you expand either horizontally across multiple markets or areas, or you expand deeper, and deeper in a horizontal play, you're rising up the summit, right? You're rising up to the summit rather. And so, those are these extra layers that come in. Peeling back the onion I kind of use in different ways, but more in a very binary perspective.

It's often to encourage our IC, but also our entrepreneurs and founders to say, "Anchor me on something simple. Let me first understand where the monetization opportunity is, as you first go-to market, and then layer in the other monetization opportunities that expand your go-to market. Taking you to the craziest idea. Such as, for example, we've got the founder of Open Water coming in and presenting to our investors, and unfortunately you're not here on Friday at [inaudible 00:29:42] in New York at 12:00.

And she, Dr. Mary Lou Jepsen came from, the professor from MIT Lab. Former Oculus, Googler. Worked with Sergey, deep tech, disruptor. All power and mighty to Mary Lou for having done many firsts in her career. Her base camp at Open Water is pretty simple, which is to create a portable, affordable, accurate, highly sensitive diagnostics towards stroke detection. The reason why is the first four minutes of detecting stroke is extremely important. It's the number two cost in a healthcare system. She's really trying to address it from an economic perspective, but also from a humanity perspective.

But as we look at base camp to summit, this company and Mary Lou has the skillset to drive this technology into being a non-invasive brainwave therapy communication platform. Simply said, disrupting Neuralink at its own game.

Daniel Stillman:

Wow.

Avantika Daing:

I'm not drilling a hole in your brain. It's a ways to go, and there are many steps on the way. Neurodegeneration included. But understanding your first step in, versus how you scale and grow, and having a methodology to that madness is important for us as investors, and especially for growth investors as they come in to support.

And so, when we bring it home, and we put it on a platform, I think coming back to your earlier question about is this what the platform is, does it allow for a continuation of a conversation? Yes, of course it does. But the platform is actually much more than that. The platform is a grouping of products that exist today in the marketplace. It's not that it's so novel that it doesn't exist, but where the novelty comes, in is that it doesn't exist on a single platform. And what I mean by that is that we have direct investment products out there, multiple syndicates. Some Known, some unknown as syndicate leaders. That's a product that sits on the platform to provide direct investment opportunities. We have sidecar products that exist in the market. A sidecar co-investment vehicle will sit on the platform. We have funds, and funds of funds that sit in the market.

Some funds do operate on a platform where they manage lifecycle from early stage funds, to opportunity funds, to secondary funds. And so, we're going to have multiple funds that sit on the platform. And then, we have the ecosystem support about bringing in the right consulting partners, the banking partners to provide creative non-dilutive vehicles to support different stage growths of capital needs, but also supports in non-capital relationships and engagement. The platform is not just about taking the conversation forward, but also making sure there's a product that meets your needs as you grow and scale. And then, the last plug I'll give in terms of the why for a need of a platform that really sets up the economic future, is that the inherent element of a platform is that your performers rise.

So by investing early into a company that's continuing to perform and provide the track record needed, that investment opportunity specifically will continue to move from one product to another, albeit on the same platform. You are actually creating a multiplier effect on investor returns by continuing to support on a single platform your risers. Similarly, it's equally important to recognize that the non-performers get eliminated very quickly because they don't have the ability to rise within the platform.

And so, there in itself, you are providing capital protection for investors while alongside providing diverse products with different liquidity profiles. Tell me an investor is not going to be interested in a platform that's able to do all of that.

Daniel Stillman:

And that's diversification at its core. In our conversation earlier this week when I asked you what are some of your favorite ways to design a conversation, you talked about dressing the cap table, and it seems to me like this is a way you coach founders to build their own platform. I see this engine in you that is thinking soup to nuts, that tends to think end to end. Has that always been your lens? How did you learn to value that type of broad end to end thinking in your work?

Avantika Daing:

Mileage. On Friday, I was one of the speakers for NYU's PE VC annual summit, and Micah from Founder Collective was there as well. Him and I were having a little chat in the corner as he was closing out the conference as a closing keynote speaker, and one of the things we were talking about is the mileage that folks like him, and me, and my partner Deborah, and others have accrued.

That gives rise to a sense of what's perceived as judgment, but it's judgment that comes with decades of experience. For me in particular, while I didn't appreciate it when I was going through my various twists and turns in my career, switching industries, switching functions, switching roles from P&L to innovation, putting out a corporate, to an entrepreneurial journey, back to corporate, back to entrepreneurial journey, I appreciate it now. Because that diversity of an operator's experience, and that mileage of 25, 28 years allows individuals that have that construct ... And I want to take it away from it being a singular conversation on me, that are able to very quickly join the dots, and venture is known as joining the dots. And the quicker you're able to join the dots, and the further the dots go to the top right-hand corner, you want to jump in with a sense of eagerness from a capital investment opportunity. But the ability to understand where things are now, and then how do you dress around it. And in specific, I think you mentioned dressing the cap table.

Daniel Stillman:

Yeah, because I'd love a good recipe. We should definitely talk about that.

Avantika Daing:

Right, I think I focus more on the cap table because of our gender mandate investment approach. It's not an investment thesis, but it's a mandate we have. And we look at the cap table early on, even when we're looking at seed companies, to understand where does the founder sit now? What access do they have from a network perspective? What's driving their thinking, for example. And I'm just taking this as super high level. If a founder is bringing their friends, and family, and they've got a network of really well known family offices that can carry them through later stage of capital needs, that's wonderful. But that doesn't allow them to diversify, to truly become attractive to venture investors, especially at later stage.

You want to think through dressing the cap table at the right time. Now, not all of it's going to happen at seed or Series A and Series B. There's a right time and a right place to do this, but it's a conversation we have with our founders early on, and we like to give them the sort of direction, and at least instill some amount of conversation to your point, about putting the bugs out there, in their head. Which is think through who is your deep pocketed investor that's going to take you through early stage to mid-stage?

Who is the growth stage deep pocketed investor that you'd like to see come in? Who is your strategic investor that is your customer, and will also be interested in taking an equity stake on your cap table? Who is your venture, early seed investor that has the right reputation to potentially bring in their network and attract some of these other caliber of investors or categories of investors that I've mentioned? And then one in particular, which is my favorite is investors that haven't had an IPO experience, often think that finding the investors that take them to IPO is their last capital need, and that's not true. Companies that go public or post IPO still have need to raise capital.

And so, you need to think through based on where you are for Series A and a Series B company, who is that type of investor. And often enough it's not VC. It can be, but it's often enough not. Who is that investor that's going to take you to IPO, but will also support you post IPO for your capital raising needs post [inaudible 00:40:41]. And those [inaudible 00:40:43]. We have great relationships. So part of it is making sure that the dressing of the cap table, the thought process starts early. We come into Series A. Part of the reason we come into Series A is because dressing the cap table is extremely important. Sometimes we look at the cap table, and even if it's a technical Series A company, we'll say, "Sorry, your lead investor coming in is a family office that's highly motivated by impact, and we love that, but it is not the right lead to be taking you from Series A and B, and beyond.

We will actually request a reconstruction of the cap table into a co-lead coming in, that will have the right construction in place to take them. And a lot of setting up the cap table at Series A prevents kind of preventative maintenance management, if you will. A lot of problems that act as bottlenecks when you reach a Series B or beyond growth stage. And some of that is you need a different mindset of [inaudible 00:41:53].

If you are a water analytical company, which we have, and one of my favorite founders out there, the company's called Ketos, K-E-T-O-S. Amazing investors that have been supportive, but the cap table needs to be constructed, now moving forward in a different way to really bring in the investors that have the ability to think through growth capital and monetization for a company that gave roots in impact. [inaudible 00:42:29] talking about water, and water quality, and quantity, right. So as a company grows, and as the personality of the companies change, and as the technology rises up the value chain into enterprise monetization, how do you evolve the cap table and the investor mindset behind it?

Daniel Stillman:

I feel like I need to quote my mother in every podcast, because she listens to most of them, so I get to say, "Hi mom." She always says, "Start as you mean to-"

Avantika Daing:

[inaudible 00:42:58].

Daniel Stillman:

Hi mom, "Start as you mean to continue," and this is a really fundamental mindset. The idea that, Oh, I will get that investor to take me to IPO and beyond when I am at a later stage versus thinking about the end at the beginning, and setting yourself up for success seems like a really valuable subject to coach your companies on. I could see why that's one of your favorite ... It's a recipe to say like, "Are we dressing this cap table well?"

Avantika Daing:

[inaudible 00:43:34].

Daniel Stillman:

And just stepping back and saying, "Is it designed with that in mind?"

Avantika Daing:

Can I interject with-

Daniel Stillman:

Yeah, please.

Avantika Daing:

... one [inaudible 00:43:40] real fun example that actually-

Daniel Stillman:

Please, of course.

Avantika Daing:

... [inaudible 00:43:43] unintended on your point about a recipe. My comment earlier about knowing and working with a founder for four years is a company, the parent original company's called Kiverdi, K-I-V-E-R-D-I, I think. The company we invested in is Air Protein, Dr. Lisa Dyson, look her up, fascinating. Grabs carbon from the air, so helps with a lot of carbon climate tech, ESG oriented problems. Not problems, solutions. But takes that carbon capture, reproduces it into protein. Chicken protein, fresh protein, and others to make it edible. Taste, smell, look, feel starting with chicken.

Daniel Stillman:

That is dressed, that's crazy.

Avantika Daing:

Now the story, and I'll give you the nutshell, because I think it's interesting, so I'm stealing a little bit of interrupting your airtime here, so apologies there.

Daniel Stillman:

No it's your airtime.

Avantika Daing:

Deborah Jackson, my partner got introduced to Lisa. Lisa leaned on Deborah in the early years to help guide her. She was looking for venture capital. When I got involved, we looked at Kiverdi. Deborah continuously worked with Lisa for the years leading into her becoming what we call Venturable, which is also a version of dressing the cap table to getting there. And Kiverdi continues to exist as a separate company in a licensing structure. We knew while it had many shots to go, and it had a lovely licensing application across industries, gas and oil, fishery, like important industries that needed disruption while creating a further longevity towards limited renewable resources, so, huge. But we knew venture would not touch it, because of its go-to-market monetization towards licensing, but also towards the setup of the industry.

And so, over the years of chipping away with what would be the right strategy, Lisa, Dr. Dyson, finally landed on creating a separate company called Air Protein with a very specific go-to market. Two words, focusing on edible, consumable protein to the end consumer. We could create a monetization as they have done with enterprise partners. They've got EDM, which is the largest ingredient provider and distributor, as a strategic investor both on the equity side but also on the customer side.

They've got enterprises on the cap table, so they're able to expand into a B2B monetization, and they've got the right engagement with retailers. Think large FMCG type distributors to end customers, but also retailers as in shopping retailers-

Daniel Stillman:

That's fascinating.

Avantika Daing:

... that are lined up and ready to come in at the right time. I mentioned that because I wanted to be tongue-in-cheek on your pun about the right recipe, because here she really had to think through putting the right recipe, pun intended, but also she had to think through the right construct of the creation of a new company, and then dressing her investor cap table, which is very different in look and feel to cover her original company.

Daniel Stillman:

It's interesting. Going back to the base camp and summit metaphor, is this a summiting opportunity for her? She has the base camp technology, and she is thinking what is a real path to growth and success given the technology. Is that a fair reuse of that analogy?

Avantika Daing:

Yes. I think her base camp for Air Protein is chicken, to be specific. There's a horizontal and a vertical play as she rises and climbs the summit. The closest in sort of going deeper into our vertical play, is expanding from chicken, to fish, to meat. And there's a reason why she chose to do meat later, or last. The market already has some options out there, but for other reasons as well. I would encourage you and the listeners to take a look at some of her TED talks, but also she speaks at different VC summits, and she explains that.

I don't want to take that away from her. The other part of her rising from base camp to summit is expanding her customer stakeholder. So from being an ingredient player, to being a distributor, end product, to enterprise such as retailers like Whole Foods and others, Krogers. Also, to FMCGs distributors, but also ... Think Burger King or health foods like [inaudible 00:49:10], that meet the customer with the end product.

And then, finally, being a brand direct to the end consumer. And these could be all scale opportunities for her. And then, frankly, if you want to expand it even further as you look at all the different magic that can happen at summit, is taking a technology just Kiverdi did, and expanding it beyond food. Into beverages, into lifestyle. And then, if one needed to take it all the way into oil and gas, you could, but you've already got a company that's doing that at a licensing basis.

Daniel Stillman:

Yeah, it's so interesting to think about all of the different ways in which you can take that core idea, the core technology and the founder's desire to make something from it. And you and Deborah just sort of chipped away that old Michelangelo and David metaphor just to find that core value proposition that was investible and attractive to bring multiple stakeholders together. I mean, that's crafting the core. You peeled the onion all the way back, and you found a core value proposition that could really start a whole new conversation, which is tremendous.

We're sadly running towards the end of our time. One question we haven't asked that I want to ask is around the different types of coaching and mentorship that founders need to be hearing as they grow their companies. When we think about this platform, when they're getting past their cap table being dressed, when they're starting to go towards growing their company, what non-monetary advice, coaching, mentorship do these founders need to hear most at those critical junctures as they grow in your experience?

Avantika Daing:

That's a loaded question.

Daniel Stillman:

Fair.

Avantika Daing:

I say that because I think female founders, diverse founding teams have a different set of considerations to be transparent. That they may not have a natural place to bring up, to ask without having a sense of a label being put on them, or a taboo being put on them. There's a very open and, well, I don't know how open it is, but there seems to be a conversation happening on founders' mental health at large. It doesn't matter what type of founder you are. White male or otherwise. I just don't know how authentic it is, but I'm glad it's happening. What we deal with is addressing a lot of that at an authentic level, but I'm not sure that, that's what I want to end this conversation on. I would probably say the two things are learn to say no to your customers, as well as investors, to be hardball on your strategy.

And there are two different types of strategy when you're ... One is focused on revenue. If you are a multi-year SaaS contract with a hardware component build in, and you've got customers saying, "Well, I'm not sure I want to pay for three years. I want to do a pilot for six months, and I don't want to pay you, and then I'll scale up, and then I'll do a contract for one year." You got to walk away from that. There are ways in which you can accommodate that, but you cannot be creating exceptions, especially early on. It's a flip of mindset, and it's nerve wrecking to think ... Most people think early on, "Oh yes, I've got a great enterprise. Logo, top 500 public company coming, why would I want to keel over?" Well, you need to set precedents, and you need to set the right precedents. You have to be a bit strategic.

I'm not saying you shouldn't accommodate for those asks, but be strategic in how you create that construct. So, for a pilot, you build a pilot in. If they like the word, "Pilot," you give them pilot, but you make it monetizable. If they want to backhand, you have to understand, again, peeling the onion back, understanding where their motivation is. And the motivation there is, large enterprises like to say, "We want to first test you, and then backend payment." How do you build that into a construct of establishing your contract, and the nuances that go into the contract that set you up for monetization.

There's a component of learning to say, "No," with a creative element of accommodation. And then the second part of, "No," is to your investors. Early investors ask for side letters. They ask for preferences. You want to set yourself up for success for later rounds, and you want to be conscious of what construct and precedents you're setting with your investors now. And having conviction and motivation on yourself in not reducing your valuation, or not wanting to give up too much ownership, whatever it might be for you as a founder or founding team, sticking with your narrative is extremely important.

It's important because it's not a one-time engagement that an investor or VC has with a founder. To your own point, Daniel, about a conversation. This is a conversation that's going to go on for months and years. Good VCs like to engage with their entrepreneurs for a period of 18 months and beyond. Smart founders like to begin that engagement earlier. And so, we want to make sure that you're not flipping from right to left and accommodating just because you're desperate on a capital need. And then, the last thing I'll say is very important. It's not done enough, and it's completely underestimated, which is think two steps ahead. Also, a different version of peeling back the onion. But if you're raising seed, think about Series As and Bs. If you're raising As, think about Bs and Cs, and why? Look at the market today.

Some of our portfolios that we've worked very closely with when they were raising the Series A, we very quickly came in and we said, "Now is the time to bring in non-dilutive capital. Meet, they're friends of ours, X, Y, and Z that are interested in funding you. Giving you a line of credit, giving you a debt vehicle if you're a Series B," bring that in. Unfortunately, you're not thinking that, because you don't have a need for it. [inaudible 00:56:58] Founders would say, "Well, I have a runway of 18 to 24 months, why do I need to think about that? I've got to runway for 36 months. Why do I have to think about it?"

"Yeah, great. I'll take the introduction, but I'm really not going to lean in. I'm too busy now trying to close my [inaudible 00:57:14] later." Well, later becomes too late, because you cannot time a situational market. And a situational market for us is a COVID. A situational market for us is consideration towards a down market. And so, to manage situational markets, when you are doing your equity round at the back of it is the time to come in and put creative financing vehicles in place. You may never need it. You may end up paying a bit, which could be the downside. But frankly, you're never going to lose out on using, and having that as a backup in creating financial health. And really, frankly, drawing that back to your own mental health in using it as a tapping mechanism.

Daniel Stillman:

That is tremendously powerful advice, a month ago. So with our literally one minute left, is there one question I have not asked you that I should have asked you?

Avantika Daing:

It'll be a question, but we won't have time to answer it, which is-

Daniel Stillman:

Well, for the next conversation.

Avantika Daing:

... are motivations aligned in the VC industry?

Daniel Stillman:

Well, it sounds like the question is posing that it's maybe not.

Avantika Daing:

You're right, it's not. And that's why there is a inherent need for a platform product presentation to be existing in VC to bring those motivations together.

Daniel Stillman:

Well, I mean-

Avantika Daing:

VC industry, if you don't mind.

Daniel Stillman:

No, no, no.

Avantika Daing:

VC is an [inaudible 00:59:14], your point about the leaky bucket. We create the leaky bucket syndrome. We're in the business of creating the leaky bucket phenomenon. And what I mean by that is as VCs we come in for two touchpoints. Some of us come in for maybe more because we've got the capital power through a dry powder, and we really like how the growth of a company's happening, and we found the needle in the haystack.

But by construct of how venture invests, and because we're thematic, and because we're stage driven, or driven through various constructs of our investment pieces, we only come in to touch an investment between one to two points, sometimes three and beyond. And by default of that, we are creating a leaky bucket. Where we're letting loose, and letting go of our investments that we've made, and we're unable to support it because of lack of capital power, or because of lack of the right platform that will allow for the growth engagement to happen.

Daniel Stillman:

And that's intentional investing at the core. Changing the conversation. This is tremendous. Thank you so much. I want to make sure you have plenty of time to get to lunch. I'm really grateful we made time for this conversation today. Is there any place that people should go on the internet to learn more about all things Avantika, and all things Plum Alley, besides the power of Google? Any place you'd like to send people?

Avantika Daing:

Thank you for asking. I have a horrible social profile. So I am unfortunately not on Instagram. I am on Twitter. My Twitter handle is @AvantikaVC. I'll spell that. It's A-V-A-N-T-I-K-A-V-C. I am on LinkedIn, and I'm fairly active, so if somebody sends me a message or inboxes me, I will respond in some shape or form. And then, our website is plumalley.co. So not com, but co. Plumalley.co. We are putting a new website up, so that should be up in the next two months. And we hope that the conversation that we've had here today would be reflected in that manifestation of plumalley.co.

Daniel Stillman:

That is so exciting. Thank you so much for this time. This has been a beautiful conversation. I appreciate your generosity, and I look forward to the next conversation.

Avantika Daing:

Yes, and safe travels to you. Thank you for allowing for a very natural, authentic conversation to happen, and look forward to engaging further.

Daniel Stillman:

Awesome. End scene.

A Recipe for Team Agility: One Page, One Hour

Today my conversation partner is Matt LeMay! Matt is an internationally recognized product leader, author, and consultant. He is the author of Agile for Everybody (O’Reilly Media, 2018) and Product Management in Practice (Second Edition O'Reilly Media, 2022), and has helped build and scale product management practices at companies ranging from early-stage startups to Fortune 500 enterprises. 

Matt and I met at UX Lisbon last year where he gave a talk that included him describing his extremely actionable recipe for team agility: the One Page / One Hour Pledge, a powerful commitment to minimize busywork and maximize collaboration that has been adopted by individuals and teams at Amazon, Walmart, CNN, and more. 

I was excited to bring Matt into a conversation about this pledge, because I know how easy it is to get caught in a rabbit-hole of perfectionism before sharing my work with others. Teams can work more fluidly if we reduce the cycle time between solo work and team work.

Matt is an advocate for the power of focus, subtraction and feedback loops over perfection - I mean, would you rather ride a bike you can only aim once or one that you get to steer continuously?

I never dreamed I’d get to have a podcast conversation that includes references to Alan Watts and the power of Ego Death to accelerate your team’s success and ultimately, one’s own success…but glad that we are! 

Matt and I unpack how TIMEBOXING (ie, Tight-and-almost-thoughtless constraints ) helps shift the relationship between thought and action in teams and organizations…and can help move the conversation forward.

Links, Quotes, Notes, and Resources

Matt's website

Product Management in Practice

https://www.onepageonehour.com/

Matt’s talk at UX Brighton on “You Don’t Get anyone to do Anything”

“When we attempt to exercise power or control over someone else, we cannot avoid giving that person the very same power or control over us” Alan Watts

Alan Watts “The wisdom of Insecurity

Summary

6:22 Matt and Daniel discuss the power of constraints, focus, and subtraction in product development

18:06 Coaching teams to use the one page, 1 hour pledge and how it shifted his perspective on what is considered impressive documentation

35:21 The role of product leaders in applying constraints, bringing focus, encouraging subtraction, and managing complexity

37:45 Matt emphasizes the importance of celebrating subtraction and user-centricity in product development

40:26 The value of continuous discovery and learning from customers regularly

44:11 Matt suggests finding a half hour every week for research with executives and focusing on tactics rather than philosophy

51:45 Matt LeMay shares a story about understanding why a decision was made, even if it's not the answer you hoped for, and the importance of asking questions to get a better understanding of the decision-making criteria
57:36 Matt emphasizes the importance of ego death in good product work and cross-functional collaboration, and the need to focus on team success rather than personal rewards or recognition

Key Quotes

Minute 10

Matt LeMay:

I used to work with a company that did these really long retrospectives after workshops. They were brutal. These were three hours. Everybody would say what they felt they had done well and what they could have done better. Everybody would go around and tell them what they had done wrong or what they could have done better. Sometimes the retrospectives would last longer than the workshops themselves. And I love retrospectives, but this was just excruciating.

Daniel Stillman:

That sounds like a ratio is off there.

Matt LeMay:

Yes. So I said, "How about we timebox this to an hour?" [inaudible 00:10:15] said, "Yeah, sure, whatever." So everyone starts going around and talking. I'm sitting there quietly. I don't say anything. And everybody talks, an hour goes off. And I say, "All right, it's been great." And they say, "Wait, no, well, we haven't finished yet." I say, "Well, clock says we're finished. We time blocked this for an hour." Everybody got really uncomfortable. But in order to change the way you think, I think you need something to force you into a state of reflection. You need something which will shake up that system between thought and action in a way that compels you to look at it and say, okay, what is the relationship between thought and action? What is driving this behavior? What is the reward I'm getting? What is compelling me to spend this time talking in this way? What is the value I'm getting out of this? Which is part of why I am such a big believer in really tight and almost thoughtless constraints.

Minute 24

Matt LeMay:

So many of these things all come back to user centricity, customer centricity. I saw Matt Cutts who had been at Google for a long time, and was working for the US government, talk a couple years ago. And somebody asked him, "How do you break through the bureaucracy of an organization as complex as the US government?" And he said, "Oh, that's a really easy one. Bring decision-makers closer to customers." No hesitation about that. And I feel like when I've seen product leaders and product managers effectively navigate that complexity, part of how you do so is by demonstrating that... I talk about this a little bit in Agile for Everybody, but there are dependencies which are felt by the customer and dependencies that are not felt by the customer. And if a dependency is felt by the customer, it should probably be felt by the organization as well.

In other words, if you have siloed folks into a bunch of teams, but a user's journey is jumping around through the thing built by those teams, then those teams should feel some pain too. If they don't, they're never actually going to make things better. Because they're going to sit within their silo and they're going to say, "Look, I'm working on my future. I'm making this area better. That's my job. There's no reason for me to talk to these other people and deal with getting outside of my comfort zone, deal with situations where what's important to me might not be important to somebody else. Deal with situations where the thing I've been working so hard on might come under a different scrutiny, or might be revealed as actually not being that valuable to the sum total user experience."

But when you see a user struggling, when you feel that sense of, oh, the complexity I'm adding is bad complexity, the dependencies we've created are harmful dependencies that are felt by the user. It's a very different thing.

Minute 35

Matt LeMay:

So if you're trying to get a room full of people to make a decision, see how each person in the room is going to make the decision, and then figure out what they're basing that information on. Then you'll probably figure out what information you need to consolidate or answer or resolve in order for the room to make a decision. But I rarely ever now spend much time thinking or talking in the abstract before asking participants in a room, how would you make this decision right now? If you have these three options, which one would you choose and why? Because that will help me understand what decision-making criteria are necessary, and it'll help me understand if I'm thinking about options the right way.

More About Matt

Matt LeMay is an internationally recognized product leader, author, and consultant. He is the  author of Agile for Everybody (O’Reilly Media, 2018) and Product Management in Practice (Second Edition O'Reilly Media, 2022), and has helped build and scale product management practices at companies ranging from early-stage startups to Fortune 500 enterprises. Matt is the creator of the One Page / One Hour Pledge, a commitment to minimize busywork and maximize collaboration that has been adopted by over 100 individuals and teams at Amazon, Walmart, CNN, BBVA, and more.

Matt is co-founder and partner at Sudden Compass, a consultancy that has helped organizations like Spotify, Google, Clorox, and Procter & Gamble put customer centricity into practice. In his work as a technology communicator, Matt has developed and led digital transformation and data strategy workshops for companies like Audible, GE, American Express, Pfizer, McCann, and Johnson & Johnson.

Previously, Matt worked as Senior Product Manager at music startup Songza (acquired by Google), and Head of Consumer Product at Bitly. Matt is also amusician,recording engineer, and the author of a book about singer-songwriter Elliott Smith. He lives in London, England.

Full Transcript

Daniel Stillman:

Okay, Matt, thank you for making me time for being...

Matt LeMay:

Thank you for having me.

Daniel Stillman:

I want to start at the beginning of me knowing you. Just, actually, I think sitting down to dinner in someplace in Lisbon.

Matt LeMay:

I believe it was.

Daniel Stillman:

I really enjoyed your talk at UX Lisbon, and partly because it is about constraints, and partly because your talk is funny. And also because while I think I seem to recall... I was looking for my notes, I couldn't find my original sketch notes from your talk. Because I was feverishly sketching during your talk. Was that like, oh, my slides aren't fancy, but your talk is funny. You are a very entertaining speaker. You entertain while you educate, and I really appreciate that.

Matt LeMay:

Thank you. I do not have the skillset to make my slides fancy. So funny is about the best I can do.

Daniel Stillman:

I want to start with the one page, one hour pledge, because I think it is a blockbuster talking about constraints and the art of focus. It is so easy to let a communication or document just bloat.

Matt LeMay:

Yes.

Daniel Stillman:

I wonder when the seed first took root in you.

Matt LeMay:

Yeah. I have always been a verbose person, and I have been the nightmare friend or colleague or romantic partner who will send you the 20-page email with all of my thoughts meticulously composed. And then say, "Well, I've done my part." But there's no way anyone could misconstrue my position, I've made it abundantly clear. And then gotten bitter and resentful when it turns out not everybody wants to read my 20-page treatise on whatever it happens to be. I am as guilty of over long, overstuffed documentation as anyone, if not more so. And I found myself working as a consultant with an organization. And frankly, just that my approach wasn't working. I was both creating a lot of big heavy documents and facilitating the creation of many big heavy documents. People weren't reading them, people were busy. I had a unshakeable sense that I was wasting people's time in order to gratify my own sense of a job well done or having done something well.

I remember the conversation very clearly. I was working with a product manager who said... Another product manager just came to me and said that they want to see what my team is working on right now. "I don't have anything." "Can you help me put together a deck?" And I said, "Well look, why don't you try just spending one page and one hour on it, and we'll see how that works out." This product manager said, "Wow, it's kind of catchy. One page, one hour." One page, one hour. A week later I said, "Well, how did that go?" This product manager said, "It was really interesting, I gave product manager who asked for it this really rough one pager and I said, 'Look, don't think less of me for this. This is a really rough document. It's just a brain dump of what my team's doing.' And they wound up coming back to me and saying, 'Gosh, that one pager was so useful. It was just exactly what I needed and nothing else. So I'm going to try making one that captures what my team's working on.'"

Daniel Stillman:

Yes.

Matt LeMay:

I said, "Oh, there seems to be something here." So I started coaching more teams I've worked with, try this one page, one hour thing. And then I was in a conversation with my business partners in the States. I live in London now, which is why I qualify that we're in the States. And I told them about this work I was doing, one page, one hour, and they both smirked at me. I said, "What's so funny about this?" They said, "We love you, but when you work with us, you give us the most comprehensive documentation." I said, "Well, yeah, but you two are geniuses and I want to impress you and I want you to think I'm smart."

And they said, "Yeah, why do you think everyone else isn't doing one pagers? They feel the same way." Oh. So it started to shift. I had seen the utility of this in terms of applying a constraint to documentation, but I hadn't seen the utility of it until that moment, and shifting incentives. I told my business partner, "Okay, look, I'm going to write up a little pledge. I'm going to pledge to you that I will spend no more than one page in one hour on anything before I share it with you. And if I break this pledge, I want you to hold me accountable. I want you to say, Matt, you may be turning in something which is very intrinsically impressive, but in the context of our working agreement, you have actually done something bad. You have actually not excelled at this. You have broken a commitment you made."

And it was really interesting having that in place because I did break that commitment several times. Either because I thought, oh, we have enough shared context, I'll just finish the document. Or because I was having a rough day and wanted that dopamine hit of having turned in something impressive. But in all those cases it didn't work. Either we realized that there were enough assumptions baked into my document that it would require rework, or my business partner said, "This is a lot, and we feel excluded by the fact that you sought to finish this thing without our input."

Daniel Stillman:

It's so interesting.

Matt LeMay:

To me, the most interesting part of the one page, one hour pledge is not so much the constraint itself, but the idea that you can explicitly shift the goalposts for what is considered a successful or impressive document. Because I'm pretty convinced at this point that if you don't shift them explicitly, they won't shift.

Daniel Stillman:

Right. And so it doesn't really matter if it's one page or two page, or if it's three slides or-

Matt LeMay:

Exactly.

Daniel Stillman:

It's really about having the conversation. And I guess I'm wondering... These are the things I'm wondering. I'm going to share one. There are several things I'm wondering and I'd like you to respond to any and all of those things.

Matt LeMay:

Absolutely.

Daniel Stillman:

One, I know you wrote a book called Agile for Everybody. And I was also reading about your perspective that there is no product mindset, there are product action sets. And so the idea that doing things differently is more important than thinking differently is a really interesting one. There's a third point, I apologize for my bloviation.

Matt LeMay:

No, it's all good.

Daniel Stillman:

There's a balance always between... There's a concept called triple loop learning, where doing the right things can get us the right actions, thinking things differently can help us notice when we're not getting the right things done to get what we want. It's impossible to shift what we're doing unless we shift how we're thinking. And it's very hard to shift our thinking unless there's a shift at the level of being. Our goal, our aspirations. And so I feel like on one hand the actions are clearly the most juicy. Like oh, we can start doing things differently, but it requires a shift of I do not need to feel impressive. I will not feel ashamed of incomplete work. I will show incomplete work. I feel like we have to work at both ends in order to have a transformation.

Matt LeMay:

Absolutely. For me, a lot of this comes from my experiences in cognitive behavioral therapy, which was really helpful for me. I remember the first time I went to see a cognitive behavioral therapist in New York, I had been in a lot of talk therapy previously. And I showed up ready to, it all started with my family. And my therapist said, "Look, that's great, but what are you doing? You have anxiety issues." And I said, "Well, I'm drinking coffee all day, and I'm never exercising. And I sit around and scroll." And she said, "Okay, well, work on those things. If you can't start modifying some behavior, I don't think we're going to have a starting point where changing your thinking is going to stick. We need to basically just create an inroad before we can start reflecting and becoming more aware of the way that you think."

And I hated this. I was so mad. I was like, oh, this is my special feelings time. How dare you ask me to change my behavior and do things differently in my life? But I found that in some cases, I think behavior and what you do is the most accessible lever. And I think that sometimes when you change what people do, especially when you apply constraints, it forces some openness. It forces people out of their comfort zone. I remember the first time... I used to work with a company that did these really long retrospectives after workshops. They were brutal. These were three hours. Everybody would say what they felt they had done well and what they could have done better. Everybody would go around and tell them what they had done wrong or what they could have done better. Sometimes the retrospectives would last longer than the workshops themselves. And I love retrospectives, but this was just excruciating.

Daniel Stillman:

That sounds like a ratio is off there.

Matt LeMay:

Yes. So I said, "How about we timebox this to an hour?" [inaudible 00:10:15] said, "Yeah, sure, whatever." So everyone starts going around and talking. I'm sitting there quietly. I don't say anything. And everybody talks, an hour goes off. And I say, "All right, it's been great." And they say, "Wait, no, well, we haven't finished yet." I say, "Well, clock says we're finished. We time blocked this for an hour." Everybody got really uncomfortable. But in order to change the way you think, I think you need something to force you into a state of reflection. You need something which will shake up that system between thought and action in a way that compels you to look at it and say, okay, what is the relationship between thought and action? What is driving this behavior? What is the reward I'm getting? What is compelling me to spend this time talking in this way? What is the value I'm getting out of this? Which is part of why I am such a big believer in really tight and almost thoughtless constraints. I love [inaudible 00:11:14]-

Daniel Stillman:

Like the one page, one hour is a thoughtless constraint.

Matt LeMay:

When you talk about 5, 10, 20 sketch storming, the idea of having five minutes to draw a diagram of something on a sheet of paper. I love that. And I've used that approach in some of the roadmap mapping exercises that I do, what I call generative road mapping. Which is, rather than trying to figure out what's the right framework for roadmapping? Just sketch what you think captures visually the story you're trying to tell about the thing you're building. I worked with an organization a while ago where we did 10 minutes of prototyping a strategy document. What would a one pager of our strategy look like? Everybody took 10 minutes, then we synthesized it. And a five hour session of talking and walking through decks and asking a lot of really important sounding, but ultimately not that immediately relevant questions wound up getting wrapped up pretty definitively when we looked at these prototypes and said, "Oh, everyone's actually thinking about the same thing, more or less."

There's a clear enough through line through this that we can subtract, we can converge, we can make this happen. I think that the last example I'll share, I've worked with a lot of teams that are really interested in this notion of psychological safety. Who say, "We don't have psychological safety, we don't have trust. This is a low trust team. What should our decision rights be?" And the first question I usually ask them now is, "When somebody on your team emails you, how quickly do they expect a response?" And they often say, "I don't know, an hour a day. Not at all." In so many cases, these things that feel like big emotional issues for a team, like a lack of trust or a lack of psychological safety, come down to very simple, straightforward, tactical misalignments.

The first step I take with any team I work with now is to create a comms manual that just says, how quickly do you expect a response over these channels? What are working hours? How do you communicate urgency? How do you involve stakeholders from outside the team? These things that might seem fairly quotidian and not big product mindset, thought experiment-y. But it's been really interesting to me how often these bigger issues are ascribed things which are really just a matter of, we have not taken the time to explicitly discuss how we communicate with each other. And some of those really simple behavioral levers have had more of an immediate and meaningful effect on how teams communicate with each other than multi here transformation initiatives, et cetera.

Daniel Stillman:

I would call that conversation design. Literally designing an email is the beginning of a conversation.

Matt LeMay:

Yeah. [inaudible 00:14:21].

Daniel Stillman:

It's weird. When we're talking in person, 200 milliseconds is about what I would expect any person to respond to me before I start to feel like there's too much silence. Or they're overthinking things. And that's just in the cultural air. For whatever reason, if you wait too long when we're talking in person, it feels like dead air. And we presumably both feel some anxiety, right? I start to be like, wow, did my question not land? Does Matt hate me? He's thinking really hard about this. And so it is not surprising that an email conversation, when I'm not getting an immediate response, would create an equal amount of anxiety, A, in the sender. And B, we all know that feeling of an email sitting in our inbox [inaudible 00:15:16] glaring at us. The analogy I always use, and nobody ever gets it, but I still use it anyway, is from Pee-wee's Great Adventure. I don't know if you-

Matt LeMay:

Oh, yes.

Daniel Stillman:

There's a scene where Pee-wee is rescuing all these animals from this pet shop that's on fire. And every time he goes into the pet shop... Well, the first thing he does is he rescues the monkeys, and the monkeys help him rescue all the other animals. Leverage. This is genius. But he looks at the snakes every time and he's like, "Ugh, snakes. Not going to rescue the snakes." And finally he rescues the snakes last. And it's like, ah, the snakes, he's got handfuls of snakes. I feel like we all have those feelings about, ugh, this email. If I could just say to somebody, I haven't responded to this email because I feel anxiety about this email, or I don't know how to respond, or I feel like I have to have a perfect response. I wish there was a comms manual for that of, hey, this email is, it's been in my inbox for a month and I don't know what to do about it. Can we have a two-minute conversation?

Matt LeMay:

Well, my business partners and I had a email subject style guide that we use for internal communications, where every email had to say, in brackets in the email subject, response required by date/time, response requested by date/time or FYI. And that was really good. Because you could look at that and if it said FYI, then you could just let it sit there. And if it said response required by date/time, you'd prioritize it. And if it said response requested by date/time, then it falls to a second tier priority because you knew you weren't in a block around something. Again, I think some of these fairly routinized, structured approaches to team communication, especially asynchronous communication. Which, as you said, if you're in a person face-to-face conversation with somebody and they start to get anxious, you see them start to get anxious and you kind of, oh, [inaudible 00:17:06] this natural dance we do. Whereas if people are sitting at their desks just stressing out about an email, they never see that and they often wind up making assumptions about the other person.

Daniel Stillman:

Yes. Well, [inaudible 00:17:19] there's a whole narrative we tell.

Matt LeMay:

Exactly. I think having those agreements in place explicitly is so important.

Daniel Stillman:

This also speaks to the point that a conversation, where the conversation happens affects the conversation. Email is not designed for this.

Matt LeMay:

No.

Daniel Stillman:

Slack is not designed for this. I wouldn't want everyone to just have all of their conversations in a sauna, but that's kind of what you're saying here. It's like, this can be embedded in every communication if we're putting it in a place that has that information as part of the communication.

Matt LeMay:

Yeah. It was really interesting, when we wrote the comms manual, my business partners and I for the first time, we started with cadence and then we went into a channel. So it was like, for I want a response ASAP, let's use WhatsApp. For, I want a response by end of workday, let's use Slack. And for, hey, 24 to 48 hours, or 72 hours max, use email. And within two weeks we had stopped using Slack. Not because Slack is a bad tool by any means, I love Slack. But because there were just very few communications that fit that cadence. It was very much either like, oh, I need an answer to this right now, or take your time. It was interesting to see what happens when you actually think through the purpose of a communication channel before you retrofit the channel itself. Because I've certainly worked with a lot of teams that go from email to Slack or from email to Teams and recreate all the same communication problems, except now they have two or three or five different channels to recreate those problems, and everything just gets exponentially worse very quickly.

Daniel Stillman:

That gives me hives. I feel like I want to talk about the evolution of product at a company. Because I feel like every company is a product company, depending on how you like to look at things. My friends who are service designers may say, but everything, every product is really a service. And that may be true, but I would say a service is a product because you buy it. And almost every product or every service is digitally mediated. At some point everybody is going to say to themselves, God, we need to get better at product. And I'm wondering, in the evolution of a company... It's like, when does a bill become a law? Or how does a caterpillar become a butterfly? I imagine in your mind there are some set points where from zero to one, from not having a product to the minimum viable or the minimum lovable, or the whatever the fastest time to value product, they don't need necessarily a fractional product leader or a head of product because everyone's the head of product, or the CEO's the head of product.

At some point it sounds like there's a moment of reorganization, focus, subtraction, and constraints forming that is hard to do on your own. Because whatever reason, because behaviors or patterns have become entrained, and there is some value in bringing someone else in. And maybe that's on a temporary basis or on an ongoing basis. And then there's another set point where they're like, we need a chief product officer or a head of product.

Matt LeMay:

Yeah.

Daniel Stillman:

What do you find that people are doing? What do you wish people knew about how to manage those transitions?

Matt LeMay:

What I wish people understood is that you bring in those roles to, as you said, apply constraints, bring focus, encourage subtraction, and manage complexity. I think the challenge I see when I've interviewed for those roles, in a lot of cases they've been seen as very additive roles. We need you to hire more people, we need you to add more people. We need to expand. And honestly, nine times out of 10, that is not the biggest problem that a growing company is facing. We can't scale and grow and hire fast enough is a real problem for some organizations. But I think as you see these wild accordion shaped expansions and contractions of companies over the last year, it's not the biggest problem.

The biggest problem is, are we focused on the right thing? Are we actually connecting all of these pieces in a way that creates a compelling experience? Are we actually focusing on the right customers right now? Are we managing our bets in such a way that if we invest in something and it fails, we can acknowledge that it is a failure, learn from it, and move on? In a lot of cases, what a product leader is empowered to do is to look at that, look across the organization, and make those calls and facilitate those decisions. And establish the criteria for making those decisions in a way that individual product managers wouldn't be able to or comfortable doing.

That is such critically important work, but it's not the work that people usually ask me about when I'm applying for an interview for these roles. Which I think is really too bad, because I've worked with a lot of companies in my day. And the challenges, the great product leaders-

Daniel Stillman:

Your day isn't over, Matt. I don't know if you're allowed to use... I'm still a young [inaudible 00:23:15] man, everyone.

Matt LeMay:

But the best product leaders I've worked with are the ones who can get a complex team to make subtractive steps. Like Natalia William, who I worked with at Mailchimp, who was their chief product officer [inaudible 00:23:30] Hootsuite, really was able to get in there and say, "What if we take a step out of this thing? What if we streamline these things? What if a way to increase conversions is not to add features, but to remove steps?" That's how I think great product leaders think. And you can tell immediately how challenging that is, because somebody built those steps. Somebody's job is to maintain those features that are going to be deprecated, and those people are going to feel a certain way about it. And of course they are. Most companies celebrate the launch of new features. They celebrate, look, we did a thing, we built a thing, we shipped a thing. And celebrating subtraction and celebrating...

So many of these things all come back to user centricity, customer centricity. I saw Matt Cutts who had been at Google for a long time, and was working for the US government, talk a couple years ago. And somebody asked him, "How do you break through the bureaucracy of an organization as complex as the US government?" And he said, "Oh, that's a really easy one. Bring decision-makers closer to customers." No hesitation about that. And I feel like when I've seen product leaders and product managers effectively navigate that complexity, part of how you do so is by demonstrating that... I talk about this a little bit in Agile for Everybody, but there are dependencies which are felt by the customer and dependencies that are not felt by the customer. And if a dependency is felt by the customer, it should probably be felt by the organization as well.

In other words, if you have siloed folks into a bunch of teams, but a user's journey is jumping around through the thing built by those teams, then those teams should feel some pain too. If they don't, they're never actually going to make things better. Because they're going to sit within their silo and they're going to say, "Look, I'm working on my future. I'm making this area better. That's my job. There's no reason for me to talk to these other people and deal with getting outside of my comfort zone, deal with situations where what's important to me might not be important to somebody else. Deal with situations where the thing I've been working so hard on might come under a different scrutiny, or might be revealed as actually not being that valuable to the sum total user experience."

But when you see a user struggling, when you feel that sense of, oh, the complexity I'm adding is bad complexity, the dependencies we've created are harmful dependencies that are felt by the user. It's a very different thing. Again, I think a lot of where I've seen really great product leadership... And I love Teresa Torres's book, Continuous Discovery Habits, is always the first book I recommend to people. And of all the things she talks about, my very favorite thing Teresa Torres has added to the discourse is the idea that continuous discovery is the team learns from customers once a week. And I love it because it's so simple. It's the most straightforward thing. It's like, you don't have to use this framework or do this complicated thing. It's like, are you just connected in that way?

Daniel Stillman:

Yeah. That is the best way to get the "product mindset" in the company, is to talk to customers more regularly. How high up should that go? And what can that look like? What is the light... If there's somebody in the C-suite who's like, that's not my job, right?

Matt LeMay:

Yeah. This is an interesting one, because this is one of the conversations that I thoroughly see both sides of. Because I have been in situations where the CEO of a company overhears something, one customer reaches out, and then suddenly that's the only thing that matters. The whole team is scrambling because-

Daniel Stillman:

He's super customer-centric now, which is great.

Matt LeMay:

Exactly. Exactly. On the other hand, I've seen situations where C-suite is super removed from customer. And every time I'd work with companies, it was like, uh-oh, executive's going off to a conference in Silicon Valley and they'd come back and be like, "What's our augmented reality strategy? I saw a talk about it." And it's like, "We're a bank. We don't have an augmented reality strategy. We have a, let's be good at being a bank strategy." But I think in a lot of ways, part of why I think Teresa Torres's definition is so valuable is that it speaks to cadence, it speaks to regularity. If you're doing this on a regular basis, then the odds of any one thing being cataclysmic actually get smaller. I think one of the big challenges, and I've talked to a lot of folks I know in user research about this, is that it is very hard to get to a place where customer research is happening well, without it happening poorly along the way.

Daniel Stillman:

Yes.

Matt LeMay:

If your goal is to avoid a situation where an executive overreacts the customer feedback, if your goal is to avoid a situation where product managers ask leading questions and do the things that product managers aren't supposed to do, you're never going to get there. You have to be ready to manage those situations and navigate them, and have those conversations. And say, yeah, here's what's happening. We're on a path. Let's manage our expectations. Let's look at this. Let's let this happen and manage it, rather than trying to over-engineer a situation where no bad research ever happens. In which case, design or UX or whatever, whoever is managing research will remain a gatekeeper forever, and you will never get in that position where the entire organization is actually participating in a healthy, unproductive way. I think you need to hit some [inaudible 00:29:22] along the way if you're ever going to get anywhere meaningful that-

Daniel Stillman:

I agree. I definitely could see resistance to a weekly cadence as you "go up in an organization". What would you tell a C-suite that says we can't do it once a week? And maybe being on the other side of the glass, once a quarter is something we can do.

Matt LeMay:

Oftentimes, I've sat down and said, "Craig, mind if we look at your calendar and see if we can find a half hour every week?"

Daniel Stillman:

Yeah.

Matt LeMay:

Just a half hour. This is, again, where I find that getting down to the level of tactics can be so valuable here. Because I understand philosophically, I understand emotionally that reaction. Look, I'm so busy. I'm like, okay, let's find one half hour a week.

Daniel Stillman:

Yeah. This is great, because now we're getting towards two other things that we haven't talked about that we should talk about. And one is, we should go back to how do you facilitate large groups of people to come to a decision? But the other piece of that is, you can't get anyone to do anything.

Matt LeMay:

Yes.

Daniel Stillman:

So this comes to, I love the word... This is just, again, I'm a chef who looks at everything like food. When I think about conversations, I think about invitation. An invitation is what insights or initiates a conversation. And cadence is the pace of the conversation, the rate of return of the conversation. And these are two things that are so critical. You cannot force anyone to have a real... You can't force somebody to fall in love. You can put somebody in the context where maybe they'll be open to it. You can't get anyone to do anything. What you were just doing with the CEO is saying, we can do it for 30 minutes on a Friday, or here's another option. You're giving them options instead of saying, hey, it's really important. Because that's resisting resistance.

Matt LeMay:

Yeah. And that fails every time, especially when you're working executives. Yeah. It's interesting, because some of the you can't get anyone to do anything talk started at that conference in Lisbon. Where during the workshop I did so many of the questions I got, well, how do we get product managers to value research? How do we get them [inaudible 00:31:48] work we do? And I felt like I was a dog chasing my own tail trying to answer that, I just couldn't get to an answer. And then I spoke at a conference remotely, unfortunately, in Athens, Greece.

Daniel Stillman:

Because it would've been great to be in Athens, I presume.

Matt LeMay:

A while ago. And it was about this Agile conference, and the first question I got was, how do we get executives to be agile? And it just came to me. I just said, "You don't get anyone to do anything." And the reaction I got was just resentful silence. Just, the room went dead. No follow up questions. That was it. And I said to myself, interesting. There's something there. I've touched a nerve. I wrote a talk that I gave at UX Brighton last year called, You Don't Get Anyone To Do Anything. And I prefaced it with my whole take on Alan Watson, Zen Buddhism, and the idea of you can't capture flowing water in a paper bag. And all that great, it goes through a lot of wisdom tradition stuff across different cultures and different religious traditions. But when I came to, you can't get anyone to do anything. Again, I got this resentful silence.

I was like, no, no, no, no. Okay, we're going to walk through this together, because this is actually the path to freedom. When you convince yourself that you can control other people and get them to do something, or that your success and your "influence" hinges on somebody else doing something, you are setting yourself up for a life of disappointment and misery. You can't get anyone to do anything. That's the path to freedom. You can state your case and try to help people make the best decisions they can. But there's been this great thread running through product management discourse in the last couple months. Michelle Cutler's talked about this, my friend [inaudible 00:33:49] talked about this a lot. That really you're creating the conditions for good decision-making when you're a product lead. You're not making the decision and you're not getting anyone to make a decision.

You're trying to just really align the criteria for decision-making and give people options, and then you help them understand the trade-offs. And if there's a disagreement, then that's in that case constructive. Because you can say, all right, are the options wrong? Are the decision-making criteria wrong? I think one of the things I learned, I remember so clearly being in a workshop about product strategy, the team I was coaching. We were two hours into this and everybody was debating, well, what should be a product strategy? And people were going up whiteboarding things, and having all these very intense academic theoretical conversations. And I said, "All right, can I try something real quick? What are 10 things this team is thinking about building?" And they listed them. I said, "All right, everybody just prioritized them yourself in two minutes, one to 10." Two very different orders emerged.

There were two very clear clusters. And I said, "All right, break into your cluster, spend five minutes preparing your verbal argument. Why is this the right order?" So everyone goes, they're getting excited. The first team goes, "Look, this team is really focused on acquiring new users. So we..." Somebody on the other team goes, "Wait, wait, wait, wait, wait. I thought we were focused on retaining existing users." And there you have it. It wasn't that there was something in page 1,000 of how to write a product strategy that was missing, but was something really simple and really straightforward. We didn't know who we were building for. And in a lot of cases, again, things like product strategy, any of these things that are designed to help us make decisions I find are better to reverse engineer from the decision you are actually trying to make than to try to generate in the abstract.

So if you're trying to get a room full of people to make a decision, see how each person in the room is going to make the decision, and then figure out what they're basing that information on. Then you'll probably figure out what information you need to consolidate or answer or resolve in order for the room to make a decision. But I rarely ever now spend much time thinking or talking in the abstract before asking participants in a room, how would you make this decision right now? If you have these three options, which one would you choose and why? Because that will help me understand what decision-making criteria are necessary, and it'll help me understand if I'm thinking about options the right way.

Daniel Stillman:

It almost seems like prototyping the decision, right?

Matt LeMay:

Yeah. I think that's a great way of putting it.

Daniel Stillman:

You can over facilitate or design a "perfect" agenda for how to architect a decision. Or you can get some people in a room and say, how would we know if this was a good decision? And what are some things you're thinking about would be a good decision for this? And just to mock it up.

Matt LeMay:

Yeah.

Daniel Stillman:

And then in a way, it's iterating.

Matt LeMay:

Exactly.

Daniel Stillman:

Is this a good decision? How do we know? What would make it better? Oh, we're not aligned on it. Okay, well great. So how can we all get aligned on it? And then you can address each component of it one by one.

Matt LeMay:

And sometimes you'll ask people, and everybody just has the same answer immediately. And then whatever the free hours you would've spent on a strategy session might have been a waste of time. Like there are times-

Daniel Stillman:

Well, there's another issue there of, is everyone aligned? Is that good or...

Matt LeMay:

Right. And one of the other things I've learned also, I'll tell another story from a workshop. I was doing the workshop with a bunch of product managers, and I talk about how part of your job is to understand why a decision was made. If your team is given something to do, it's really important for you to understand why. And not to just storm off and say, well, fine, we'll do it. We're like, no, we won't do it. Understand why. And somebody made a noise. And I'm like, huh. "Oh, hello, you made a noise." She goes, "Yeah, I don't agree on it." "Great. Tell me why. Is there a particular experience?" She said, "Yeah, I was told to build something. I kept asking and I kept asking, and I kept asking. And eventually I was told, look, somebody promised this to the board, so you just have to build it. Okay? So now I don't bother asking anymore."

And I said, "Oh, congratulations/I'm sorry you did your job. You got the answer. And getting an answer doesn't mean getting an answer you like." And that's one of the hardest things to accept in life and in product management, is that there will be times where you go and you get an answer, and it's not a good answer. It's not the answer you hoped for. It's not the answer that leaves you feeling awesome, and let you understand exactly why something was done. But if that's the real answer, there are times in real world organizations where you say, okay, great. What exactly was promised? What exactly is the wiggle room in this? [inaudible 00:39:03]-

Daniel Stillman:

Well, why does the board want what it wants is not an unreasonable question. Somebody would say, oh, well... See, this goes back to cognitive behavioral therapy, and our own relationship to power, authority, and optionality. That person heard that and said, well, there's just no point in me asking anymore. And there was somebody who would say, oh, why does the board want that? Why do they think it's important for the organization to be doing this? What is their vision for this organization as opposed to the C-Suite's view for what this needs? Why is the chief of product officer and the board not aligned on this?

Matt LeMay:

Yeah. And I do think there comes a certain point where you might just need to throw your hands up and say, I've asked as much as I can.

Daniel Stillman:

Fair. No, no, totally.

Matt LeMay:

As an IC product manager, I'm probably not going to be able to get much time with the board. But if I know that this is at a certain altitude, and I have a sense... I deal with this a lot with companies that say, "We're a marketing driven organization. Marketing told us to build this thing." Well, then I go to marketing and I say, "What'd you tell them?" "No, this is the story we need to be able to tell, but I don't care what they build. I don't care where the pixels are." And I go back to product and I'm like, "Well, what do you think they meant by this?" "Well, I don't know. They told us to build this."

I'm like, "Yeah, when marketing tells you we're going to build a portal or a platform or whatever, there's so much wiggle room within that." There's so much opportunity to say, all right, not only to ask what does that mean, but to say, okay, when you work in that collaborative, iterative way, it breaks down a lot of the silos naturally. And again, I feel like simple time constraints are such a massive enabling factor.

Daniel Stillman:

Well, and we have a time constraint that sadly we're coming up against. I usually ask, is there anything I haven't asked you that I should ask you? And I do want to ask that question. This thing you're just talking about, I know someone who has this challenge where, I know you said there's no such thing as a product mindset. But if sales are the people who have the most contact with the customer in a particular venture backed startup that shall remain nameless, how might we help them frame conversations so that they are promising stories and not features?

Matt LeMay:

Yeah, here's the thing.

Daniel Stillman:

Is that a-

Matt LeMay:

I think that's a great question. And I think the first thing to acknowledge is that if you work at a sales-driven organization, show some respect to the sales team. I'm a bad salesperson. I'm terrible at sales. And I have so much respect for people who are good at sales. I often say that you can reframe a, how do I get question as a, how do I help question. If the question is, how do I get sales to stop selling things that we have to build? You're going to lose. How do I help sales sell more? How do I help them be more successful?

Daniel Stillman:

Oh, my God, did I do that? How can I get... After all that we just talked about, that you still use a how do I get?

Matt LeMay:

No, no, no, you didn't. You didn't. I'm paraphrasing. I'm conveniently paraphrasing. But I think that at the heart of most questions coming from one function about the behavior or intentions of another function or another person, is this idea that I know how they should be behaving or what they should be doing.

Daniel Stillman:

Oh, God.

Matt LeMay:

And they're not doing it the way I would want.

Daniel Stillman:

My God, you have read too much Alan Watts. This is [inaudible 00:42:32].

Matt LeMay:

I wish I had Alan Watt’s voice. [inaudible 00:42:35]-

Daniel Stillman:

This is the game of black and white. This is the game of black and white versus this is a both and, this is a curiosity mindset.

Matt LeMay:

Yeah. If I go to sales and I'm like, "Hey, I want you to sell more. I want you to make more money. I want to understand how you sell. What can product do to help you make more money for this company?" That's a very different conversation. And-

Daniel Stillman:

Then stop selling features that we have to build.

Matt LeMay:

Right. Because, I'm sure sales is frustrated too that they have to... [inaudible 00:43:08]-

Daniel Stillman:

Why haven't you built this yet already?

Matt LeMay:

Exactly. It can be a win-win when you go in trying to understand what somebody wants to achieve and help them achieve it. And the good news is, in most organizations if you zoom up to a high enough altitude, you do want the same thing. You want the company to make money. Make a lot of money. You want to be successful. Once you get out of your own silo and your own sense of... One of the things I tell product managers all the time is that the things you do to seek personal rewards and recognition will almost always be harmful to your team. The things you do that you feel that are increasing your personal status, your personal visibility, are intrinsically antithetical to how product work plays out. Which is to say, that the group efforts, the team efforts are always the most impactful things. I think once you can really accept that your team's success is your success, your company's success is your success, there's a degree of ego death that goes into good product work. And I think good cross-functional work in general.

Daniel Stillman:

Which is why everyone should be in some therapy so that they can work on preparing for that ego death, which was Socrates' whole perspective. With zero minutes left. I feel like they do always do this on NPR. So with the last 30 seconds, Senator, would you please... If you had a billboard, what would we put on it? We're going to put this, you can see this from space, everyone can read this. What's Matt LeMay's message to all people, especially the C-Suite of developing product organizations?

Matt LeMay:

Yeah. I would say for that audience, I would say focus is a bigger risk than scale. Not having focus is actually a much bigger material risk to your organization than not having scale. And to everyone else I'd say, you don't get anyone to do anything. And I'd tell them to go read The Wisdom Insecurity by Alan Watson.

Daniel Stillman:

Yes, it's a good one. Aside from reading your books, Agile For Everybody, and Product Management And Practice. And going to your website at mattlemay.com. Where else would you like people on the internet to go to learn more about all things Matt LeMay and to stay in connection with you?

Matt LeMay:

I'm more active on LinkedIn than I am on Twitter these days, so you can find me there.

Daniel Stillman:

I saw your conflict about Twitter.

Matt LeMay:

Yeah. It remains a profound conflict in speaking with... And keeping with the idea of decision-making happens, I'm creating the conditions for good decision-making. Yeah. And mattlemay.com. I'd say the second edition of Product Management And Practice came out this year. I'm very proud of it. Or last year. It's a new year, I keep forgetting that.

Daniel Stillman:

Happy New Year.

Matt LeMay:

Real proud of that one. And otherwise, yeah, I think that just about covers it.

Daniel Stillman:

Matt, thank you for making the time for this conversation. This is really great stuff.

Matt LeMay:

Thank you. Yeah, this was really fun. Appreciate it.

Daniel Stillman:

Yay. We'll call scene. 

The Surprising Power of Two Hour Mid-week Cocktail Parties

In 2019 My friend Philip invited me to a 2-hour cocktail party at his tiny apartment in the Lower East side. True to his word, the gathering, which was on a Tuesday night, started at 7 PM sharp, and at 9 PM he kicked us out onto Orchard Street to enjoy the rest of our night and/or to get to bed on time (since it was a weeknight, after all!)

I met a whole bunch of awesome people, and if I’m honest, I thought Phil was super cool for bringing such a lovely group of people together. The food and drinks were nothing to write home about, but no one cared. Phil stopped the party two or three times to get us to circle up and introduce ourselves and respond to an icebreaker prompt. It was pretty fun.

He mentioned during the party that he was following an early draft agenda, a recipe if you will, for such gatherings, that was being developed by his friend Nick Gray, who I knew of through other friends. Nick had started a company called Museum Hack that had blown up - in the good sense. They were leading creative tours in Museums around the city, so I guessed this guy Nick knew a thing or two about getting people together.

Cut to 2022 when Nick Gray’s book “The 2-Hour Cocktail Party: How to Build Big Relationships with Small Gatherings” came out. Here it was, four years later! I was fascinated to talk to Nick because I thought “How much could there be to this? Isn’t it all in the title!?” How much could the form have evolved over 4 years of prototyping and testing?! 

I’ll tell you folks…this is a polished gem of a book.

If you’ve followed my work, you know that I’m a bit of a nerd when it comes to gathering/facilitation/conversation design. I love card decks about it, books, diagrams, narrative metaphors to fuel creative innovation in gathering science for skilled facilitators to bring diverse stakeholders together to tackle wicked problems. I have coached leaders on this skill, all over the world. I hosted many, many cohorts of my 3-month Masterclass on Facilitation that people lovingly described as “drinking from a firehose” of facilitation while somehow being spacious and deeply mindful of how we gather. Managing complex gatherings is a crucial skill!

Companies that can’t come together to discuss and decide on actions for their biggest challenges will not survive! And I love these types of gatherings - they are never the same, they have to be absolutely customized, and deeply considered. 

Nick, on the other hand, has designed the “CheckList Manifesto”, the “Design Sprint” or the “Joy of Cooking”...not for any and all types of gatherings - but for one, single, Life-changing, surprisingly powerful gathering - a 2-hour, midweek cocktail party.

Nick’s book is designed with absolute beginners, or those hesitant or nervous to lead gatherings in mind…but masters of gathering will be pulled in too…I was.

Nick designed this insanely in-depth book to cover everything from snacks to drinks to how to write an invitation to…everything. Where to put name tags. How big those tags should be. You get the idea.

While I am a nerd in the sense of being an omnivorous gathering nerd, Nick is an obsessive compulsive nerd of this one form…and for good reason.

Nick believes, and I now do, too, that if more people felt more comfortable with having more gatherings we would all be more connected. The midweek 2-hour cocktail party just might save the world.

You can get the gist of the form from this conversation (I mean, even from the title!), but if you’re a gathering nerd like me, you'll absolutely enjoy Nick’s insanely thorough guide, which I found myself flipping through regularly as my wife and I prototyped our own first midweek,  2-hour cocktail party, which we titled a “Serendipity Salon”. 

I think we all need more serendipity in our lives, and that’s why I loved the opening quote I pulled from my conversation with Nick - the ability to take a short conversation with someone and turn it into a deeper one, to create a space where your old and new friends can connect with each other…only good things can happen from creating more of that type of serendipity in our lives. My wife and I have hosted two parties like this already and, as Nick has advised, we have our next one in the books! I hope you will, too.

Links, Quotes, Notes, and Resources

How to Host a Party Website

The 2-Hour Cocktail Party: Book info

The 2-Hour Cocktail Party: Amazon

Nick Gray's personal website

3 Tips on How to Plan a Networking Event

Clothing Swap: How to Plan the Party 

How to Host a Happy Hour: Tips, Tricks, and Best Practices

Minute 8

Nick Gray:

Now, one of the key elements of the Nick Party Formula, which is N-I-C-K, name tags, icebreakers, cocktails only, and K stands for kick them out at the end. The N, which is name tags, has become something so natural to me that I don't even think twice about it. But your question made me think, "Gosh, what was it like the first time I used name tags? Why did I use name tags?" And I tell you, I meet so many people, I host so many events that, maybe this has happened to you, people know your name and you... I'm very bad with names or I'm someone who is bad with names at times. And so I said, "I'm just going to start to use name tags from my own need and want, that I don't remember them." And then I saw how much it helped other people. Constant experimentation and then reflection afterwards of who were the best guests? What were the best activities? How did that go? How do I think about that? That's something I'm very, very intentional about.

Minute 15

Daniel Stillman:

So it's very interesting because sometimes new ways of doing help us think and be differently. There can be that transformation of, "Here's how to do it." And I think it will open up things for people. I want to really zoom in on this idea that... So, you mentioned serendipity and serendipity has been one of these words that has been lighting up and expanding for me. Specifically, this term about building serendipity engines in our lives. And so, because doing a party once will not be the engine you're talking about. So, a minimum viable party is not doing a party. In a way, what is the viable party habit in order for it to become an engine of serendipity in someone's life, do you think?

Nick Gray:

Well, and how you can take it to turn it into an engine of serendipity is by always having your next party scheduled on the calendar. Why is that helpful? Because today's Tuesday, as we record this, you go out tonight, you meet somebody interesting either at the line in the grocery store, on the subway, at a party, at a friend's house. What is your next step of action if you think somebody's interesting? I got to be honest, these days it's very rare that, besides me inviting them to a party, that I would say, "Hey, we should really have dinner sometime." That is a reach for me and, I think, for many other people. It requires a large level of commitment, vulnerability, scheduling is difficult.

But what I found from living in New York for 13 years and meeting thousands of people, was that I could invite them to my party and it was a very easy invitation. By the way, that's why I call these cocktail parties. It's not about the drinks. I don't drink alcohol myself. I don't know how to make a cocktail. But the phrase cocktail party encapsulates a social construct of a lightweight gathering where you'll have a lot of little conversations with minimal commitment, where you can bounce. You don't have to be there like a dinner party, you're trapped, you're stuck, that's three hours.

Minute 33

Daniel Stillman:

If you're doing this monthly, what is the cadence that you would recommend to somebody, and how do you create variety of the list from party to party?

Nick Gray:

For myself, generally the advice I tell people is every six weeks or so, you should be hosting something. And I like to invite about half regular people and half new people. And that helps mix it up. Using those words as well, there's always new people. Using that phrase when you explain it to somebody, number one, makes them feel more welcome. They're not walking into a party with established cliques. And number two, makes them not feel left out if they don't get invited again. The idea that there's always new people is something that will make these parties a success.

Minute 37

Daniel Stillman:

Why do the first icebreaker so early in the party? Because I know in your agenda, it's almost right out of the gate, right? It's pretty early in. Everyone is not necessarily even going to be at the party yet. And as an experienced facilitator, I still felt awkward breaking the frame of the traditional party. Which is, things are just kind of happening and everyone's kind of on their own. And to bring in structure early in the party, breaks the pattern and shows people a different sort of thing is happening here. I actually think it takes guts. Even as an experienced facilitator, I'm like, "Oh my God, this is not the place for me to be doing this." So, why do it? And, why do it so early?

Nick Gray:

So as an experienced facilitator, you may appreciate my reasoning on this. Many of my readers have never hosted an icebreaker before. In fact, they're terrified about the idea of leading an icebreaker. And so that first icebreaker, number one, is meant to get them out of the awkward zone. But number two, is to show them that icebreakers work and to make it easier to stop a party with fewer people, to know that when they have to stop it 20 minutes later when everybody's there, that it's going to work.

So it's for the purpose of the facilitator just as much as it is to get out of the awkward zone. The awkward zone is the zone that I describe as the first 10 or 20 minutes of a party when you haven't reached critical mass. Sometimes the people that you don't know the best have shown up early and it just is what it is. It's awkward. We do an icebreaker there to just get the conversations broken up and add a little momentum, create some excitement.

But I really do it for the hosts. I used to hear from so many people, before adding this first icebreaker, they'd say, "Oh, I did the party and then I never did the icebreaker. Everybody was having fun, I didn't want to interrupt it." And what they're really saying is, "I was too nervous. I was a little scared."

More About Nick

Nick Gray moved to New York City with very few friends and less-than-stellar social skills. But Nick craved new relationships and exciting opportunities. He started hosting non-traditional parties—a move that opened doors he never could have imagined.

Today, after hosting hundreds of 2-hour parties, he counts business owners, artists, and inspiring teachers among a circle of friends that helped him launch a multimillion-dollar company, Museum Hack. Featured in The New York Times and The Wall Street Journal, Nick has been called a host of “culturally significant parties” by New York Magazine.

Full Transcript

Daniel Stillman:

Well then I will officially welcome you to the Conversation Factory. Nick Gray, thanks for making time to talk with me about talking.

Nick Gray:

I'm excited to talk about talking, and parties and networking and all those things.

Daniel Stillman:

Well, yeah, because isn't a party just a bunch of people... I mean, I suppose talking is one of the things that's supposed to happen at a party.

Nick Gray:

Yeah, yeah. Parties are a lot of talking. Although now that I think about it, what would it be? Yeah. And so parties are a lot of talking and I've written a book that just helps add a little bit of structure to that talking. What do you think about structured talking? Do you ever show up to a friend hangout with a list of topics to talk about?

Daniel Stillman:

Are you trying to reverse interview me Nick Gray?

Nick Gray:

Yes. Yes. You're the pro. I want to know the expert. What does he do?

Daniel Stillman:

Well, clearly you value structured dialogue. Right?

Nick Gray:

Yeah, yeah.

Daniel Stillman:

Well, I really want to start way back, which is, why did you want to undergo, undertake this project? Because I don't know if you know this, I feel like we talked about this over email, but I went to an early prototype of this formula, our friend Phil Van Nostrand invited me to a two-hour cocktail party in 2019. So, you've been working on this for a really long time.

Nick Gray:

Yes. I've been working on this for a long time.

Daniel Stillman:

Yeah. When did you first start having the conversation with yourself about, this is something I would like to do?

Nick Gray:

Literally, it was over five years ago that I had built a Google doc for my friends that was the outline of this book. And I never planned to make a book, but it was just something I did for fun, for free, for my friends to use when they moved to a new town or want to make friends. And about five years ago, I started to think, "Huh, maybe I'll make this into a book." So I've been thinking about it a lot. And I suffer from the disease of perfectionism, which is to say that, I just wanted to make the book perfect and beta tested and get it into a thousand people's hands before I came out with it. So that's why you went to a test with Philip, which is really proof, I think, if you want to tell your listeners, that is a small apartment and it is proof that you can be successful even in a small apartment.

Daniel Stillman:

It's true. And he didn't have fancy snacks or fancy drinks. He did, at the time, have an outdoor space which was pretty prime, and he was on Orchard Street. So it was a very cool apartment, which I presume you've been to at some point. So I want to go further back then, because why did you write this guide for your friends about how to have parties? Because that's-

Nick Gray:

I got so much-

Daniel Stillman:

... that's not normal, Nick. I don't know if you know this, not everyone does that. Right?

Nick Gray:

Yeah, to do that, I guess. So yeah, I've been writing and sharing on the internet for over 25 years and I got so many benefits myself, from hosting parties. I saw other people get benefits from hosting parties that I think, just like you know the benefit of conversations, I know the benefit of building a network of acquaintances. And I found that I was able to launch my business, have success through those relationships I built up in hosting these parties. And after I sold my business, I was like, "All right, this is my next thing. I want to give back. I want to share that with others."

Daniel Stillman:

It's such an interesting journey to undergo. Why that? You're like, "This is going to be my windmill. I will tilt at this windmill. This is the horizon." I'm sure you could have done many things and you do other things. This is the thing that's so fascinating to me, because recently I wrote an article about what we should do when we think about taking on a new project, because this is something that we are all faced with all the time. And, what made this light up for you?

Nick Gray:

So for me, I think about how much value I can give. What will have the maximum amount of value? And I have found that hosting a party, when I can actually get somebody to host a party, I get to talk to people afterwards. And the level of satisfaction and success and how proud they are and the sense of accomplishment from leveling up in a life skill. Something fun that I like to do is I like to teach people how to juggle. And about 50% of people I can teach how to juggle in less than five minutes. The other 50% will take me hours and I'm not able to help them because I'm not that patient. But about 50%, based on how I see them throw two balls, I can know, "Oh, you can immediately learn how to juggle." And I love teaching people how to juggle because they get that sense, that feeling of accomplishment.

Similarly, with writing this book and with making this my mission, I said, "Wow, this is truly something that, number one, I'm an expert at. I've taught hundreds of people how to host a party and I personally have probably hosted a thousand parties now, and I've learned a specific formula that can make a gathering very, very successful." And I just said, "Yeah. I think if I'm going to write a book, if I'm actually going to share a detailed set of instructions and knowledge and lessons learned, that really is the only thing that I could truly write about that gives massive amount of value." That is my why of why I chose this topic and why I'm obsessed with this goal and, gosh, why I'm spending so much time on it, which is kind of ridiculous.

Daniel Stillman:

It is amazing. Well, so I want to talk about this pursuit of perfection and go back to structured dialogue because it's interesting. You've been interested in structured dialogue for a really long time. Do you have a sense of when you started to be aware of, to understand, to be interested in structuring how people get together?

Nick Gray:

In hosting my parties... So I lived in Williamsburg, Brooklyn when I first moved to New York, and I didn't have a lot of friends. When I first moved to the city, it was for the express purpose of building friendships. I worked in the majority of my 20's in a family business, helping my dad grow a company from the basement of our house into a much larger organization. And I'm so thankful for that time but also, I literally lived and worked with my parents every single day of the week. A fun Sunday for me would be to wake up early, go to Waffle House, and then go to the office where I had the whole office to myself and get work done. Right? It wasn't healthy from a social perspective.

So I moved to New York, I think maybe I was 26 or 27, and I said, "I'm really going to work on making friends." And this is what helped, was a little challenge. My roommates in college had moved to New York and they were very successful. And I sort of felt a sense of rivalry or a feeling that I didn't want to live in their coattails, that I didn't just want to ride and mooch off of their success. And I said, "I'm going to make my own friends. I'm going to learn how to meet people." And I'd go to things like networking events and I just wasn't successful at those events. So I said, instead of going to bad parties, I'm going to bring the party to me. And I learned, through a series of experiments, that by adding a little bit of structure to those parties, I could make them much better for other people, which would then help me make more friends.

Daniel Stillman:

Yeah. Well, let's talk about minimum viable structure. What kind of experiments did you start with? When you think about your early experiments in partying, what was the spark for you to say, "Oh, let me do, blank." What was an early prototype that you ran?

Nick Gray:

Now, one of the key elements of the Nick Party Formula, which is N-I-C-K, name tags, icebreakers, cocktails only, and K stands for kick them out at the end. The N, which is name tags, has become something so natural to me that I don't even think twice about it. But your question made me think, "Gosh, what was it like the first time I used name tags? Why did I use name tags?" And I tell you, I meet so many people, I host so many events that, maybe this has happened to you, people know your name and you... I'm very bad with names or I'm someone who is bad with names at times. And so I said, "I'm just going to start to use name tags from my own need and want, that I don't remember them." And then I saw how much it helped other people. Constant experimentation and then reflection afterwards of who were the best guests? What were the best activities? How did that go? How do I think about that? That's something I'm very, very intentional about.

Daniel Stillman:

So what's so interesting to me about your book, and it is a really, really interesting book, is that-

Nick Gray:

Thanks for saying that.

Daniel Stillman:

So I don't know if you're aware of her work, I've had my friend Kat Vellos on the show, she has written a book called We Should Get Together. And it's about the friendship epidemic, or the lack of friendship epidemic. And you probably know, and many of our listeners probably know some of the statistics, actually Casper ter Kuile talked about this too. He wrote a book called The Power of Ritual, and he talks about how Americans, as a whole, lost one friend on average. Most people, if you asked them, "How many people can you talk to?" And I think you read about this in your book too. Everyone just has fewer people to go to.

And there's this idea, Casper's book is more general, it's like, "Hey, ritual is important and here's the power of ritual and creating ritual. And we lack it, and religion used to provide it and it doesn't anymore." Similar, I think, Kat does have recommendations, but they paint a palette of problems and options and opportunities. And what's fascinating about yours is that it's a bullet. I think it's a really good silver bullet, but it's such a specific, well-polished, well-honed bullet to solve some of these challenges of loneliness and disconnection. And you've stripped so much complexity out of it, you've made it so streamlined. It's such a different approach.

Nick Gray:

So, I like that you said that. And I don't feel that that's an insult, that it's one bullet-

Daniel Stillman:

It's not.

Nick Gray:

Right. It's not, right?

Daniel Stillman:

No.

Nick Gray:

Because my book is very targeted. And one of the biggest things I worry about is people like yourself or people like Kat, who you said, reading my book, which may seem like very elementary-level advice. "Here are the supplies to buy. Remind people to take their shoes off. Put a candle in your bathroom." Right? These are very, very elementary pieces of advice. But what I've learned in talking to hundreds of people, is that nobody teaches the basic skill of hosting. And there's a lot of books, I'm sure you've read Priya Parker's, The Art of Gathering, an absolute classic, that in my mind is written for experienced hosts. It is a very theoretical book that talks about the theory of why we gather.

I wanted to write the book for someone who's never hosted a party before. I want to write a book to take someone from zero to one, to encourage a whole new generation of hosts. And I'm hoping that that's what I'm doing. Turbo hosts, people who host already, yes, they can absolutely learn some interesting things from this book. They'll blaze through it in half an hour. But I also love hearing from people that are like, "Dude, I read your book three times. I highlighted it. My party is in six weeks, I've made all these notes." I literally had a guy who read my book... Yes, thank you. I see on the video, Daniel's holding up a book with a bunch of notes in it. I heard from some-

Daniel Stillman:

Well, because I am a highly experienced gatherer and I still read it being like, "Huh, that is in the weeds. Those are some interesting choices. I don't agree with all them, but those are interesting specific points of view." And I think there is something useful about, as you say, Priya's book is way up in the abstraction level of the why. And yours is...

So sometimes I talk about this, there's a classic thinking tool called the abstraction ladder where you talk about why, intention, with how. And you say, "What are we here to talk about? Gathering. Why do we gather? What are all the reasons why it is important to gather?" And then it is also important to talk about the how, and why is not more important than how. And people need to be specific at some point and concrete about, well how do we gather? Let us actually talk about the nuts and bolts of it. And putting sticky notes into bowls so that you don't forget to put certain things out is a great hack. It's a great reminder. I read it, I was like, "I do do that sometimes and I'm going to do that more often." And good hosts do that, because then you don't forget to put the cheese out.

Nick Gray:

So a lot of my book is about trying to create the MVP, the minimum viable party. Because I believe that the biggest benefits come to those who can make hosting a habit. Now I could have written a book about how to throw the craziest party and a step-by-step guide and, "Do this party to blow your friend's minds." But the reality is that people would read that book and they'd host that party exactly once. Because afterwards, they'd be stressed, they'd be frazzled, their home would be a mess and they'd be hungover the next day. I have found that if you can make hosting a habit, it will truly change your life. And I tried to break it down into the process. I'm looking at that ladder of abstraction and at the very bottom, the bottom tier says process level. That is what my book is 95% process. You're exactly right.

Daniel Stillman:

So it's very interesting because sometimes new ways of doing help us think and be differently. There can be that transformation of, "Here's how to do it." And I think it will open up things for people. I want to really zoom in on this idea that... So, you mentioned serendipity and serendipity has been one of these words that has been lighting up and expanding for me. Specifically, this term about building serendipity engines in our lives. And so, because doing a party once will not be the engine you're talking about. So, a minimum viable party is not doing a party. In a way, what is the viable party habit in order for it to become an engine of serendipity in someone's life, do you think?

Nick Gray:

Well, and how you can take it to turn it into an engine of serendipity is by always having your next party scheduled on the calendar. Why is that helpful? Because today's Tuesday, as we record this, you go out tonight, you meet somebody interesting either at the line in the grocery store, on the subway, at a party, at a friend's house. What is your next step of action if you think somebody's interesting? I got to be honest, these days it's very rare that, besides me inviting them to a party, that I would say, "Hey, we should really have dinner sometime." That is a reach for me and, I think, for many other people. It requires a large level of commitment, vulnerability, scheduling is difficult.

But what I found from living in New York for 13 years and meeting thousands of people, was that I could invite them to my party and it was a very easy invitation. By the way, that's why I call these cocktail parties. It's not about the drinks. I don't drink alcohol myself. I don't know how to make a cocktail. But the phrase cocktail party encapsulates a social construct of a lightweight gathering where you'll have a lot of little conversations with minimal commitment, where you can bounce. You don't have to be there like a dinner party, you're trapped, you're stuck, that's three hours.

Daniel Stillman:

It is much harder to get the check early if it's not working or if it's awkward. It's a high commitment space. So I love this idea, and I agree with you, that having your next party in the calendar is a way to continuously invite people into your circle if you want to. Do you have other intentional engines of serendipity in your life that you could identify?

Nick Gray:

For sure. I send a friends newsletter irregularly that began as just a simple BCC email to my friends. Maybe I send it quarterly or once a year. And I got that from my parents, who grew up in the Air Force, and their friends would move and get stationed at new bases. So they'd send these annual cards with life updates to all their friends that they had met. And I started doing my own version of that to my friends, maybe quarterly, maybe yearly, just what I'm up to, some cool books I read. I tried to add value. But that friends newsletter for me is definitely a serendipity engine.

And it's different. Because now, these days people are like, "Oh, you should start a newsletter." The problem with that is you start it around a topic and ultimately you get bored with that topic. It becomes a responsibility, not an opportunity. When I keep mine to a friends newsletter... I think everybody should have a friends newsletter. When I keep it to that idea of what I am interested in, for people that I know, yes, the audience is smaller, but I maintain the consistency. So I think that's one that I'm excited about.

Daniel Stillman:

That's awesome. Any others that come to mind?

Nick Gray:

I've been experimenting with using social media more, short form video on certain platforms, tweets on Twitter. I haven't seen the benefits that some of my friends share, that once they go viral. I'm probably seeing stuff, but at the moment it feels more like a waste of time.

Daniel Stillman:

Really? Because you are really active and super intentional about creating stuff on Instagram. I look at your posts and your stories a lot.

Nick Gray:

Yeah, I'm trying. I love doing my stories. I love doing my stories. I was reflecting on this with a friend and they said, "Oh, is there any downsides to sharing as much as you do?" And I said... Well, let's take you here for an example, Daniel. I don't know if you've commented on any of my recent posts. You might look at them but if you don't comment, I don't see them. And so many of my friends, I believe, have a relationship with me as a viewer. And so that would be something that's a little different. Yes, I get recognized when I go out. I actually, oddly, get recognized on the street sometimes. It's great and it's flattering, but also it's like, I don't feel that it's a two-way street and sometimes I wish it was more two-way.

Daniel Stillman:

Yeah. Yeah. So I mean, then this becomes a question of how do you get somebody from the sidelines of your life into the center? Because the parties are just the beginning presumably, right?

Nick Gray:

Yeah. Yeah. The parties are the beginning, but they're also better than social media. I do feel really strongly on the power of gatherings. I believe that the purpose of these parties is almost like you're auditioning your friends, and you're auditioning who you want to spend more time with. A party is a chance for you to gather 15 to 20 people and to afterwards be able to say, "Oh my God, I forgot how much I love Dan. Dan is hilarious." I'm going to follow up and say, "Dan, what are you doing this weekend? I want to hang out. Let's try to do something." Right?

Daniel Stillman:

Yes.

Nick Gray:

And so I love parties for that opportunity to reconnect with acquaintances, to look at new people in our lives and to think about who we want to surround ourselves with.

Daniel Stillman:

Yeah. It is like taking that serendipity and just pushing that flywheel and getting it revved up and going again.

Nick Gray:

The serendipity flywheel. That could be a good article.

Daniel Stillman:

Totally. Well, so one thing that I really thought was so interesting in the granular level, the super how level of your book, that is connected to this idea of serendipity, was the language around growing your guest list. And being really specific around, you can bring a friend versus invite a friend.

Nick Gray:

Yes.

Daniel Stillman:

Can you talk a little bit about experimenting around that language? Because it was intentional.

Nick Gray:

Yeah. So many people who read my book want to grow their network. They want a new set of friends, they want to meet new people. Maybe they have the same friends that they do the same things with, but they wonder how their life could be different if they had more entrepreneurs, more writers, more podcast hosts in their life.

Daniel Stillman:

Let me tell you, having more podcast hosts in your life, definitely an improvement.

Nick Gray:

Game changer.

Daniel Stillman:

Game changer. Invite us to your parties.

Nick Gray:

Absolutely. They come with agendas for one, and you know there'll be show notes afterwards.

Daniel Stillman:

We may make a visual map, there may be stickies. Yeah, it's possible.

Nick Gray:

Right? There could be stickies, a visual map, which was awesome by the way. So, thinking about how you really meet new people. And one of the things that I'll hear from people is, "Look, you say in your book you need to have 15 to 20 people. I know about eight people. I know enough for a dinner party but not for a cocktail party this big. How do I get more people to come?" And one of the easiest ways is to ask all of your people, or some of your close friends, to bring a guest. Now I found through experimentation, that that is a very different ask than ask them to invite a guest. Inviting a guest is a simple act of, "Hey, yeah, I'll share the link to it." Bringing a guest expresses intent and action and results. Bring someone with you. Success is that you show up with someone. Inviting a guest, they could say yes or no.

Even in my own experience from hosting hundreds of parties and knowing thousands of people, I still only have at most a 50% success rate with inviting someone and them actually showing up, and that's like on a good week. Why is that? It's not because my parties are bad or they don't like me, well maybe it is, but people are busy. People have things going on. And so I tell people, make sure that you tell them to bring a guest. Ask them, "Who are you going to bring? I'd like to get a head count." And doing that, I think, is very helpful way to grow your guest list and start to meet more interesting people. I have one other master pro tip that I've never shared before that I can share with you because you're into this stuff.

Daniel Stillman:

Oh, I am.

Nick Gray:

So I have a Facebook group for people that have read my book and then hosted their second, third, and fourth parties. And I keep track of everyone who hosts one party, but then if someone actually builds this into a habit, I create a free group on Facebook just to share ideas. And someone was asking, "Hey, I'm really struggling with how do I get more people, more new people to come?" And I remembered the most successful thing I ever did. I said, "Look, I've experimented with a lot. Sending surveys afterwards, asking them to bring a guest. The number one thing I've ever done was the most aggressive thing." And it was the following. I stopped the party after I'd ran one or two rounds of icebreakers, so people knew that I'm a good host and I host a good event, when there was good momentum...

Actually I think I did this towards the end of the party. So everybody was having a great time, they knew that this was a good event. I stopped the party, I turned down the music, I said, "Hey everybody, I need five minutes of your time to help me. I'm trying to meet new people. The reason I host this party is to meet new people. So I'm going to ask you to write down someone's name, write down your own name and someone else's name." Then I passed out index cards and pens. I said, "Write down your name at the top and write down the name of two interesting people who I might be able to invite to one of my next parties." You don't have to write their contact info or anything. I'll follow up with you with an email that you can forward to them and if they're interested, then maybe they can reach out to me.

I passed those note cards out to everybody, they wrote down two names. I got so many referrals because the next day I sent them a nice message. I said, "Hey Daniel, thanks for coming to the party last night. Here's the group photo. You mentioned that I could maybe reach out to John Smith and invite them to the party. Would you mind forwarding them this blurb?" "Hey, my name's Nick. I live in New York. I host parties where I get together interesting people. We have name tags and icebreakers and it's two hours long near Washington Square Park. Write me back if you want to come." It was an easy message with the group photo that they could forward onto somebody. And doing that, in the moment at the end of the party to get the names, was the single most effective thing I've ever done to absolutely amplify all the invitations to my parties.

Daniel Stillman:

Yes. Now, I'm assuming that you didn't put that in the book for reasons.

Nick Gray:

Yes, yes, yes. It's advanced. It's an advanced level thing and my goal with the book is simply to get somebody from zero to one.

Daniel Stillman:

And I think that's so interesting that everything we make is our choices. There's choices inherent in everything we make. And I love that you were really clear and intentional on the zero to one, that you want everyone who feels like they want more connection in their life, that this is one clear action that they can take, which is making a party happen in their lives. And I want to just talk about something that we haven't been specific about, which is the fact that the name of your book, I'll say it in the introduction and this will seem repetitive now that I'm saying it now, and this is a weird meta moment, but it is a two-hour cocktail party. It starts at 7:00 and goes till 9:00, or starts at 6:00 and goes till 8:00. Or I suppose it could go from 8:00 till 10:00 if you're nuts and you hate your friends. And it's in the middle of the week because that's a day when people can actually, you can get people's time. Nobody has anything to do on a Tuesday or a Wednesday.

And the power of... And I think I sent you this on Instagram. Somebody had a sign, it was a cartoon where it was like, "Please leave at 9:00 PM." Knowing that there's a clear ending, where did that inspiration come from for you? Saying, "Look, it's not 90 minutes. That's too short. It's not two and a half hours, it's not three hours." You're like, "Here it is, two hours." What are you optimizing for and what are you sacrificing in that choice?

Nick Gray:

I'm optimizing, first and foremost, the number one thing that I've found that will guarantee the success of a party is simply the number of people. If I can get someone to have between 15 and 20 people to show up and they follow my rules and foundations, I almost know that their party will be a success. Why is that? Because the number one thing that will make a party a dud is if they don't meet the critical mass. A cocktail party works when you have the energy in the room that is exciting to walk around. That gives you the opportunity to meet new people and also a little bit of FOMO that you know you won't be able to talk to everybody. When you have a two-hour party, it's easier to say yes to, first and foremost.

Second, we host the parties only on Monday, Tuesday, Wednesday nights because those are non red level days that aren't socially competitive. A two-hour party also almost guarantees that you'll end it when things are going well. And what I found was that when I end it going well, people are ready to come back. They want to come back. They can't believe that it's being ended early, in their mind, and yet they thank me for it afterwards. "Oh my god, thank you so much." I'm seen as a host who brings leadership to the scheduling. So those types of things for me make it easier for people to say yes, they're happy when they leave, they thank me for it. And also frankly, I like my sleep. I don't want to go to bed at midnight when my house is a mess. I want to go on with life. I don't know, it's a very type A way of hosting parties.

Daniel Stillman:

It's very interesting. One of my favorite Shakespeare quotes... And this is from Romeo and Juliet and it goes by really fast. Most people don't remember this quote because it's not, "What light through yonder window breaks? It is the east and Juliet is the sun," which... Or "Goodnight, goodnight. Parting is such sweet sorrow," blah blah blah, all that shit. It's the scene when they're leaving the party after Romeo and Juliet have met and they've realized, "Oh shit, we're in love with someone who's from the other side." Mercutio comes up to Romeo and says, "Away. The sport is at its best."

Nick Gray:

Wait, that's a great line. Wait, that's incredible.

Daniel Stillman:

Yes. Now he's going to Google it and find out that I'm misquoting it slightly, I'm sure. But Mercutio says this to Romeo, he's like, "Look, we got to go. It's good. The party's good and we're going to leave at the peak."

Nick Gray:

Yes, that's the best.

Daniel Stillman:

Because this is peak end theory, right? Disney talks about this. People can Google peak end theory. So, ending a party at the peak is bold and it's a risky move to say, "You know what? There's more juice here, but guess what? Come back next month."

Nick Gray:

Is the peak end theory the same idea that they say that you should finish a vacation with a high note.

Daniel Stillman:

Well, so you remember the peak experience and then the last thing that happened. So this is one of the reasons why my wife and I talk about this, sometimes changing your location... Like, you stay someplace for 10 days. If you stay in two places, it's almost like you've been on two vacations because you remember, "Oh you remember we were in Athens, that was amazing, that meal in Athens." You're like, "Oh, and when we were in Heraklion in Crete, that was amazing." So you've made two peaks and you remember those two peaks and you remember both ends. And so yes, you want to end on a high note. "Away. The sport is at its best," because that's where people remember it.

Nick Gray:

I love that. In my book I talk about, briefly, how to end your party on a high note. And I talk about ending with a little bit of a cheer. And I do this often at my parties. It seems silly, it seems like summer camp, and yet it adds some finality to that moment. It adds an ending that's distinct, that's definitive and that's, frankly, so different from what most parties do. What do most parties do? Oh, people just start to trickle out, and eventually some people are the last to leave. Or the host makes some thing or some people make, "Oh, let's all go to this bar," or something like that to keep the night going. When you end it definitively, distinctly with some sort of fun activity, she talks about this in the art gathering as well, it really just sets your party apart. And I'm trying to give people a formula to host successful events. That, by adding a little bit of structure, you can set your party apart from a lot of different people.

Daniel Stillman:

You really can. And I can imagine now, your vision of the minimum viable party. We do not have so many of the institutions and organizations that allowed for gathering to be happening more regularly. I can imagine a world where everyone is just like, "Yeah, I throw cocktail parties once a month. I get everybody together." I think that's a better world.

Nick Gray:

I want that world. I want to live in that world.

Daniel Stillman:

Well, you do live in that world, Nick.

Nick Gray:

That's true. That's true. I do spend all day.

Daniel Stillman:

The rest of us are trying to get into that world with you. So one question I have for myself, personally, is do you ever find that 15 to 20 is the optimal number and if you get to more than that it's a different type of party? Do people want to always come back? How do you create variety in your list? If you're doing this monthly, what is the cadence that you would recommend to somebody, and how do you create variety of the list from party to party?

Nick Gray:

So it's a sliding scale of how often you want to host a party. I think you could host once a quarter, you could host once a year. For some people they never host and once a year may be enough for them. I talked to a guy last night at dinner who recently got out of a divorce and sold his business. He has more time and money than he knows what to do with and, for him, I said you could probably host every two weeks. You have a support staff to really do this, you know so many people.

For myself, generally the advice I tell people is every six weeks or so, you should be hosting something. And I like to invite about half regular people and half new people. And that helps mix it up. Using those words as well, there's always new people. Using that phrase when you explain it to somebody, number one, makes them feel more welcome. They're not walking into a party with established cliques. And number two, makes them not feel left out if they don't get invited again. The idea that there's always new people is something that will make these parties a success.

Daniel Stillman:

And so it's being really intentional about the fluidity and acceleration of this serendipity flywheel that you're running and communicating to people. You're not necessarily going to come back every time, but that's great for you. Right? Because I'll invite you to the one that's going to be happening in June and it'll be a different party then.

Nick Gray:

So my worst fear is that someone coming to one of my parties listens to this podcast in advance of showing up to my party, and they show up to the party and say, "Hey I know this is an audition, how do I ace it?" I'm just like, "Oh gosh."

Daniel Stillman:

Well then, I'm sure you have an answer for them. "Just have a good time."

Nick Gray:

Yeah, something like that.

Daniel Stillman:

Well, so I want to talk about icebreakers because it's so important and I feel like they're such a divisive concept. Because there are obviously people in the world who loathe the icebreakers in all forms, and there's some people who value them and crave them. And I imagine that icebreakers had a role in your first business... Maybe not your first business, in the Museum Hack. I imagine you had to gather people and move people around and connect them. How did you get into icebreakers? What was your philosophy of and how has it evolved, of icebreakers? Because I presume early parties, maybe you weren't as adept or adroit and you'd tried some that didn't work. Like before you said, "Here it is. Here's my unified field theory of icebreakers. At 7:10, 7:40, 8:20, these are what to ask. Go." Like you didn't hatch out of an egg with that complete.

Nick Gray:

About 12 years ago, I started to lead tours at the Metropolitan Museum of Art and it was a hobby project that later turned into a big business called Museum Hack. I realized in leading those tours, which again was something I did for fun for free, that I needed to get people talking. And so just like the number one metric for a house party is how many people show up, the number one metric for success for a museum tour was, are people asking me questions? Is this an interactive tour or am I just the sage on the stage who's performing? And I knew, or at least from my own experience I found, I needed people to talk and ask me questions. That massively made the tour that much better for me and everyone else involved.

To do that, I needed to get them comfortable talking in an art museum, which can be an intimidating space. And so very quickly in the first 10 minutes of a tour, I would lead a round of icebreakers that I found were very helpful simply to get people talking. The answers, I didn't care about. What I needed was for them to break the ice and start talking in the sacred space of the museum. That theory and that learnings and lessons came into all this party planning.

Daniel Stillman:

Yeah. Why do the first icebreaker so early in the party? Because I know in your agenda, it's almost right out of the gate, right? It's pretty early in. Everyone is not necessarily even going to be at the party yet. And as an experienced facilitator, I still felt awkward breaking the frame of the traditional party. Which is, things are just kind of happening and everyone's kind of on their own. And to bring in structure early in the party, breaks the pattern and shows people a different sort of thing is happening here. I actually think it takes guts. Even as an experienced facilitator, I'm like, "Oh my God, this is not the place for me to be doing this." So, why do it? And, why do it so early?

Nick Gray:

So as an experienced facilitator, you may appreciate my reasoning on this. Many of my readers have never hosted an icebreaker before. In fact, they're terrified about the idea of leading an icebreaker. And so that first icebreaker, number one, is meant to get them out of the awkward zone. But number two, is to show them that icebreakers work and to make it easier to stop a party with fewer people, to know that when they have to stop it 20 minutes later when everybody's there, that it's going to work.

So it's for the purpose of the facilitator just as much as it is to get out of the awkward zone. The awkward zone is the zone that I describe as the first 10 or 20 minutes of a party when you haven't reached critical mass. Sometimes the people that you don't know the best have shown up early and it just is what it is. It's awkward. We do an icebreaker there to just get the conversations broken up and add a little momentum, create some excitement.

But I really do it for the hosts. I used to hear from so many people, before adding this first icebreaker, they'd say, "Oh, I did the party and then I never did the icebreaker. Everybody was having fun, I didn't want to interrupt it." And what they're really saying is, "I was too nervous. I was a little scared."

Daniel Stillman:

Have you tried-?

Nick Gray:

And so, that's-

Daniel Stillman:

One of the things I struggled with was doing an icebreaker in the round, where everyone gets to hear everyone, versus a paired or small group icebreaker. And I'm wondering if you experimented with multiple rounds of small breakouts versus circling up and having everyone go round the horn. Because it's a very fundamental tension in pushing the conversation out to the edges, versus keeping it in the circle.

Nick Gray:

Yeah. I think you're exactly onto something special, which is that breaking into small groups is a little better. People are more engaged when they can talk more. Some people don't like to talk, but they probably like that more than the anxiety of going around the whole room. The short answer to your question is, you are thinking again as an advanced facilitator.

Daniel Stillman:

I know.

Nick Gray:

You have to remember that this book was written for the zero to one and for them to manage small groups and breakouts... What I find when I break people into pairs, you lose control of the room. You absolutely lose control of the room. And so I lead this activity, it's a module I've written about, I'll include it in the show notes, called Speed Ice Breakers. It's where you pair the entire room up, you split them into two lines, have them face off and you give them all one minute per question and then one line steps down and the other steps back. And you do about 10 minutes, 10 questions. And it's actually very hard. As soon as you release the group, everybody explodes in 10 different conversations. And to get their attention, to get them quiet 10 different times is really a lot of work. And for the purpose of this introductory beginner's book, it just didn't make sense.

Daniel Stillman:

No, it makes a lot of sense. It's about creating a frame that's not hard to explain. And reclaiming the attention of the group is non-trivial.

Nick Gray:

Oh my God, it's so hard. It's so hard.

Daniel Stillman:

So, also so hard, is to finish this conversation because we've just scratched the surface. It is a universe in this grain of sand, Nick. We are coming to the end of our time though. What have I not asked you that I should have asked you? What is important for us to talk about, to touch on that we have not touched on?

Nick Gray:

Well, we don't have the time for it but I would be curious, maybe we could sort of collaborate together on an article for my blog or something. But it's exciting for me to talk about the theory and the advanced facilitation strategies. So things, like you mentioned, that I was writing down, the peak end rule. No one's ever mentioned to me about the theory and the science behind these things. That, for me, I'm just in the weeds, "Put a candle in your bathroom and remove your bath towels." And you're like, "Oh, this is this. And this is this." I'm like, "Oh man, I should hang out with you more to sound smarter." Because I'm just like-

Daniel Stillman:

You're very kind. Well, so the question I want to... And I would be so happy to have a, we call it the 202 level two-hour cocktail party. What is the biggest difference between somebody who reads this book and does nothing and somebody who reads this book and takes action? Because that is your key metric and I think it is the key to transforming, to living in the world that you want to see, which is people are more connected to the people they want to be connected to. So what is the difference between somebody who doesn't throw a party and somebody who does? And what's the difference between someone who throws a party and somebody who develops a minimum viable party habit?

Nick Gray:

So, I would encourage your listeners to think about how their lives would be different if they had a full social calendar, if people invited them out to things, if you had new friends who encourage and inspire you. And know that all of that can happen. In the time it takes you to watch a Netflix movie, you could host a cocktail party for 15 or 20 of your friends. I've written a book that lists a formula of exactly how to do it for under a hundred dollars in supplies in even the smallest of apartments.

If you see on video here, I live in basically a studio apartment. I've hosted many parties in small apartments myself. That is my goal is to reach 500 people to read my book and host a party. There is a loneliness epidemic. We're in a friendship recession, so to speak. And I know that your parties will be successful because you'll help your friends meet other friends. And bringing those people together, I found that everybody wants to know someone who brings people together. All that it takes is a little party.

Daniel Stillman:

Aw. So can I actually just tell you with the one minute we have left, my wife and I ran a two-hour cocktail party in October in preparation for this and because I wanted to gather more. I also run an annual eggnog party. This year's the ninth year I've done it, although we had to skip a couple for the pandemic for reasons that'll be obvious to some people. And this year at the Eggnog party, which was a very welcome return, my friends, my longtime friends, the ones who I have been to eight of the nine or seven of the nine eggnog parties, said, "I met some new people." And that's because we invited several people from, what we called, the Serendipity Salon in October.

Nick Gray:

Nice.

Daniel Stillman:

And for one of my old friends to say, "You really helped me meet some... I love my friends and I love my friend's friends." And if it wasn't for the two-hour cocktail party, my eggnog party, my annual bash of boozy eggnog that I make from scratch in large quantities would not be as rich and interesting. So, thank you for that.

Nick Gray:

Really cool. I want to come to your eggnog party.

Daniel Stillman:

Sure. Well, I have some leftover eggnog, so if you're in New York in the next month or so, you can just drink some of the leftovers. It's good for several months longer.

Nick Gray:

It sounds like a party. Thank you so much for having me. This has been great.

Daniel Stillman:

Nick, thank you so much for making the time. It's been a really great conversation.

Launching a Remote, Asynchronous Venture Studio

Today I sit down with my friend Barry O'Reilly, who’s a co-author of the bestselling book “Lean Enterprise” and author of “Unlearn: How to Let go of past success to achieve extraordinary results”. He’s also the host of the Unlearn podcast. He’s also the co-founder of Nobody Studios, a global and asynchronous Venture Studio in the middle of raising a crowd-funding round (500K so far!) on Republic where anyone (including me!) can be part of their mission to fund 100 companies in five years.

As part of my ongoing series about co-founder relationships, I wanted to bring Barry on to unpack how he and his co-founder connected and decided to make this project happen, how they cross-pollinate insights from venture to venture and how they use a platform-centric approach to create synergies among their portfolio companies.

Along the way, we explore how Barry has learned to leverage serendipity and intentional connection to build his ideal life and lots of insights about how to run remote-first!

Links, Quote, Notes, and Resources

Back Nobody Studios on Republic

Learn about all things Barry here

Minute 10

I always think half, again, to your serendipity piece, half of the fun about people getting to know you is artifacts and finding resonance in different things that you're interested in. I always think it's fun, especially when we're on these, so much of our time is spent on these remote calls that when you have a couple of small artifacts, things that you're interested in, pictures, books or photos. I have my guitar here as well, which I sometimes play people with, which is always super fun. Some people in our team actually, we get on a jam. It's real fun.

Minute 18

What do you feel like you've had to unlearn the most in order to get to where you are now?

Barry O'Reilly:

I think just not being so hard on myself is probably the first thing. When I was in university-

Daniel Stillman:

Do you have a secret for that, for everyone listening? I don't think it's just me and Barry who are hard on ourselves.

Barry O'Reilly:

Yeah, no. It's crazy. I had some experiences where I put myself in very bad positions because I almost had unrealistic expectations for myself. First example was when I was in university, I got into my mind that I had to do well. I had to get a first or an A1 or whatever the equivalent is in the educational system. I put so much pressure on myself to say, "If I don't get that, I've wasted the last four years. I still remember our final exams had eight exams to do and we were on the fourth exam, or the first three had gone really well. But in the middle of the fourth exam, my mind just went totally blank. I mean I couldn't even remember my own name. I sat there for I'd say most of the actual exam period, just staring at a blank page and I couldn't write words. It was one of these sort of first moments where I'd actually realized I'd put so much pressure on myself that I'd sort of flipped, if you will. I had frozen.

Daniel Stillman:

Yeah, you'd basically choked out enough blood to your brain through stress that you couldn't think anymore.

Barry O'Reilly:

Nothing. It was just one of these moments where it's like, what am I doing to myself? It was really interesting and I still remember leaving the exam hall and walking home, whatever. I spent the rest of that day almost sort of totally removed from myself. That was sort of one moment where I really got a glimpse into, "I need to find ways to manage myself." That was probably one of, at the time very difficult, but also a great learning moment for me. Over time, I think all of us and a lot of people like yourself and others who we've big ambitions, we're trying to do bold things. We like to all get outside our comfort zone and do well. What I remembered is that it's not about perfection, it's about excellence and just how can you show up and give your best rather than have to be the best.

Minute 35

Barry O'Reilly:

It's been really fascinating to bring all these people into a collaborative portfolio. This is probably a little bit of a difference from a superpower if you will, that a venture studio has. It's because all the companies in our portfolio are essentially, everybody in each individual company earns equity in the company they're working in, but they also earn equity in the studio as well. So they're collaborative. In many, many respects, and that's very different from a typical venture capital portfolio because they might have three analytics platforms or two food delivery products, so there's competition, if you will.

But in a studio it's collaborative. Also we have this notion of building blocks. So there's companies that are in our portfolio that we use to build companies on top of. A simple example is Thought Format, it's a serverless, no-code platform. We build another one of our products ovations, which is a virtual events platform for speakers and emerging talent on top of that no-code platform. So these businesses sort of first customers if you will, were each other. So they can learn faster, hire trust, iterate quicker, and they have really good conversations at one another to improve both of their products.

Minute 41

Barry O'Reilly:

I always remember one of my, so two of my family are chefs and one of my friends always says, "The sign of a great dinner party is that when you arrive and the person is still cooking and they're cleaning the kitchen as they go." That's the ultimate chef.

Minute 47

Barry O'Reilly:

In the earliest stages of starting companies is a huge lift. It's all the energy to turn the flywheel is manually created by just you showing up, trying to do as much as you can. Push the boulder up the hill if you will. It will always want you to be pushing it.

You have to learn how to self-regulate. This is again, another really strong lesson I learned even going back to this, your point about when I sitting there in university thinking, "Oh, I've got to work the most," or, "I've got to show up the most." Or, "I can't miss a meeting," or. It's easy for people sometimes to fall into that trap. I see it in myself, our team and our founders, but we're also one of our other values is people first in the studio. We constantly, you see the team check in with it one another and go, how are you doing? How's your energy?

Did you have a meeting last night that finished at 10 o'clock and now you're on a call at 4:00 AM? What's going on? Are you okay to do that? There's empathy there. That is because we are irrationally global, the sun does not set on the studio. There is somebody up working at high velocity somewhere all the time pinging you on asynchronous communications if they're blocked. So one of these notions of setting boundaries and having systems is imperative. One of the things I've made an intentional investment about is exercise.

So I literally book time in my diary, just like a meeting, where I go and train. Some of that training is I enjoy mixed martial arts, so I get a trainer to come to my house and we train in the house. Or else if I play sports rugby, I love playing rugby, I play that. These things are systematically built into my schedule that forced me to do them.

More About Barry

I work with business leaders and teams that seek to invent the future—not fear it.

I've been an entrepreneur, employee, and consultant. After several startups, my focus shifted towards venture company creation, and advising entrepreneurs and executive teams where I've pioneered the intersection of business model innovation, product development, organizational design, and culture transformation.

I'm the author of two international best sellers, Unlearn: Let Go of Past Success to Achieve Extraordinary Results, and Lean Enterprise: How High Performance Organizations Innovate at Scale—included in the Eric Ries series, and a Harvard Business Review must read for CEOs and business leaders. I'm an internationally sought-after keynote speaker, frequent writer and contributor to The Economist, Strategy+Business, and MIT Sloan Management Review.

I'm faculty at Singularity University, advising and contributing to Singularity’s executive and accelerator programs based in San Francisco, and throughout the globe.

I'm a cofounder of Nobody Studios, a venture studio with the mission to create 100 compelling companies over the next 5 years.

Founder ExecCamp, the entrepreneurial experience for executives, and management consultancy Barry O'Reilly LLC.

My mission is to help purposeful, technology-led businesses innovate at scale.

Reach out via barryoreilly.com/contact

Full Transcript

Daniel Stillman:

Barry O'Reilly, welcome to the Conversation Factory. This is your first time here.

Barry O'Reilly:

Oh yeah, it is. Well-

Daniel Stillman:

It's crazy.

Barry O'Reilly:

... I wonder what's taken us so long to do this, man?

Daniel Stillman:

I don't know.

Barry O'Reilly:

Well, I'm a huge fan of your work.

Daniel Stillman:

You have a podcast, I've got a podcast.

Barry O'Reilly:

Yeah. No, it's great to catch up and get to do this show together. I have obviously, been a huge fan of your work. I was very lucky to attend one of your short workshops many years ago when, I think, Google were holding their Design Sprint Conference and kicking that off.

Daniel Stillman:

Yeah.

Barry O'Reilly:

And Kai is a mutual friend of ours and I just loved your facilitation class, one of the best classes I've done on that. It's been a pleasure getting to know you then and continuing to know you now, so thanks for having me on the show.

Daniel Stillman:

Thank you, brother. It is, if this is a nice context. How did you know Kai and come to be at the... For those listening, this was a secret conference that was very cool.

Barry O'Reilly:

Yeah, so Kai Haley...

Daniel Stillman:

And I was like how did know these, because there was internal Google people and then there were consultanty, thought-leadery folk like you and me. And it's like I felt lucky to be there with a friend of a friend. So how did you find yourself?

Barry O'Reilly:

Yes. So Kai Haley's a fascinating lady. She actually ran the Design Sprint community for Google inside of Google. So most people probably know Jake Knapp as sort of the advocate. He wrote the book, "Design Sprints," but Kai was basically the lady that trained everybody inside Google how to do them.

Daniel Stillman:

Yeah.

Barry O'Reilly:

So there was a group of people that were trying to advocate for design thinking in UX inside Google. Herself and Jake being just a few of them. But yeah, Jake obviously left Google and went on to Google Ventures, but Kai stayed within Google, ran design relations and started these conferences. I actually met her through a mutual friend, would you believe?

One of the things I used to do when we lived in San Francisco is we would have these dinners where three people would go out for dinner and every other dinner you would give up a seat and introduce another person to come along. So it was a really interesting way to network and meet new people in the city. And the guy who introduced me to Kai, his name is Bruno. He was actually looking after, sort of partnerships for Visa at the time. And yeah, he was like, "You got to meet this friend of mine, Kai." Yeah, that's how we became friends. And me and Kai speak regularly. She's at Coinbase now setting up their international design work. Fantastic lady and I'd highly recommend people check her out and follow her.

Daniel Stillman:

Yeah, I had Kai on the podcast a long time ago. I admired the work that she did inside of Google greatly. [inaudible 00:02:38] Because people do have, there's this story about sprints and like, "Oh, this is how Google works." And it's like, well, it's because Kai and a few other people built a really, really thoughtful train the trainer program, and-

Barry O'Reilly:

Yeah.

Daniel Stillman:

... that did not happen by accident.

Barry O'Reilly:

No, not at all, like you know. And I've worked in companies where it's a very strong engineering culture. My sort of last definitive real job, if you could call it that, was working at a company called ThoughtWorks, which was one of the early pioneers of the agile software movement. And a lot of people, continuous delivery, continuous integration. These types of techniques were born out of there. But it was a really strong engineering culture. I still remember when I joined, it was still a small company, maybe a couple hundred people at the time. And everyone kept asking me like, "Do you write code?" And I'm like, "No." And then the next question was, "Well, what do you do then?" "Oh, you are a manager?" And I was like, "Well, no, I'm kind of interested in building products."

I remember as we brought designers into ThoughtWorks, there was always this sort of reticence against anyone who wasn't writing code. And I know Kai felt a lot of that as well inside Google-

Daniel Stillman:

Yeah.

Barry O'Reilly:

... where it's just a strong engineering culture and trying to bring design thinking, getting people to spend time with customers, doing actual good UX, was the transition the company had to make. And herself, Jake and a bunch of other people I think, should instrumental in that happening.

Daniel Stillman:

Yeah. Yeah, the classic going slow to go fast. Making sure we're having all the right conversations, which as you know is one of my favorite-

Barry O'Reilly:

Yeah.

Daniel Stillman:

... axes to grind, rows to hoe. You mentioned something though that I think is totally worth diving into and was not on the docket at all. One of my most passionate curiosities these days is this idea of having serendipity engines in our life. And I feel like we used to have many serendipity engines. The office was a serendipity engine, coworking spaces, conferences were serendipity engines. Bars. I used to have a Sunday night gathering at a fairly well frequented neighborhood bar for many years. And that's how I made a lot of friends. Now that group of friends has migrated from bar to bar and we still meet together on Sunday nights. It's been 10 years, but it's not the same serendipity engine. It's now more an intimacy engine.

Barry O'Reilly:

Yeah, totally. Yeah.

Daniel Stillman:

The idea of a three person, who started this, or is it just lost in the mists of time? Who started this format and does it still exist?

Barry O'Reilly:

No. [inaudible 00:05:19].

Daniel Stillman:

Is the dinner still happening someplace?

Barry O'Reilly:

Yeah.

Daniel Stillman:

Well it's still happening in the Bay.

Barry O'Reilly:

Yes. Someplace. Yeah. Well, it really started because one of my colleagues at ThoughtWorks, Steve Ambosh, he's a great guy and he was sort of ran a lot of business development in sales and these types of things. But he says someone who's great, at like joining dots. I'm sure those people in your network. He's very kind and liberal with his time, his connections and his network. But he was like, "When I moved to San Francisco," he was like, "Hey man, we should catch up for dinner. Let's you and me, and why don't I just bring someone along that I think you should meet?"

He actually brought Bruno along to this first dinner and they had met at a Salesforce convention. He went up and talked to him because I don't know, he liked the jacket he was wearing or something. Anyway, those two became friends. So we had that dinner and then Dean said at the end, "Well you guys should stay in touch and why don't you invite somebody different onto the next time? That's literally how it started. I met Kai and then at the next dinner I didn't go and I suggested that David Bland, who wrote "Testing Business Ideas," he should go and meet Kai and Bruno. They all hit it off. That was just a little way that we started to network. At different times I'd go out for dinner with Kai and she would bring someone along or vice versa. It was just a great way, especially as I was new in the city when I just first moved there. It was just a fantastic way to meet some great people who've now become great friends.

Daniel Stillman:

This is wonderful. I did an interview last year with a guy Nick Gray, who wrote a book called, "The Two Hour Cocktail Party."

Barry O'Reilly:

Oh yeah?

Daniel Stillman:

So my recent experiment, I love the philosophy of gathering. As you know, you've been in a MasterClass around facilitation with me. I'm a nerd about it. And I think it's great to nerd about.

Barry O'Reilly:

Yeah, you're good at it.

Daniel Stillman:

Gathering in general, but it was, it's so interesting to talk to somebody like you or with Nick who's like, "Here's one recipe," it is the sprint. There is a power to giving somebody a recipe that says, "Here, this will help."

Honestly, I've been running, I ran one in October and I said to my wife, I was like, "Can we do this every month?" She was like, "No, but we can do it every couple of months." We gather 15 or so people, and it's just seven to 9:00 PM on a weeknight. It's like, "Oh, this is a recipe for creating serendipity. It's a recipe." I've been calling it a serendipity salon. It's a recipe for getting people together and a three person mystery swap dinner. Like fascinating. Maybe that should be your next book. The secret to a great career is a mystery, a three person rotating dinner, but we needs a better name. We don't have, what did you call it?

Barry O'Reilly:

I can't even remember what we call it. Was it, "Dinner with Stranger," or something? I can't even remember. But as you say, you can design serendipity and it's such a huge part. I definitely, I would say in retrospect, thinking about my own journey about how I've met people. You have to put yourself in situations for those things to happen, if you will.

Daniel Stillman:

Yes.

Barry O'Reilly:

Even today, I lived in San Francisco for six years and we moved to Manila 12 months ago. Actually, I'm celebrating one year living in Manila today.

Daniel Stillman:

Holy... Has it been a year?

Barry O'Reilly:

Been a whole year. Yeah. Time flies as well.

Daniel Stillman:

I just feel like so recently you were just like, "Ah, my container's not here yet. Oh, it got here, I'm sitting at my desk."

Barry O'Reilly:

Yeah, no. That was eight months. Thank you, COVID and the supply chain damages. Yeah, my container sat in the port in Oakland with oh, 75 ships sat outside the Bay of Oakland for four months.

Daniel Stillman:

Oh dude.

Barry O'Reilly:

[inaudible 00:09:29].

Daniel Stillman:

I feel that that happened to my books during my book launched during COVID and they got stuck in the container someplace as well. So you can stay, but it's not the same thing as, so we're not going to have this video up, but behind you is an Optimus Prime, a really nice one.

Barry O'Reilly:

I got that for... Yeah, my wife got me that. I'm a Lego nut. She got me it for the holidays. Yeah.

Daniel Stillman:

Is that a Lego Optimus Prime? Because I was thinking, "Wow, did he bring this all the way from San Francisco," your Stay Puft Marshmallow Man, the Optimus and the mask. Tell me about the things behind you and how they help you through your day. I'm really curious.

Barry O'Reilly:

Yeah, well, it's super fun. So yeah, I'm a Lego junkie. You might be able to see here. I also have the "Yellow Submarine" Lego.

Daniel Stillman:

Oh.

Barry O'Reilly:

Which is-

Daniel Stillman:

But it's still in its box.

Barry O'Reilly:

Still in its box. The piece de resistance is, I've actually got the original Death Star logo or a Lego down on the bar here. It has to remain covered because my kids, when they see it, will want to tear it apart. So that's one thing, but.

Yeah. I always think half, again, to your serendipity piece, half of the fun about people getting to know you is artifacts and finding resonance in different things that you're interested in. I always think it's fun, especially when we're on these, so much of our time is spent on these remote calls that when you have a couple of small artifacts, things that you're interested in, pictures, books or photos. I have my guitar here as well, which I sometimes play people with, which is always super fun. Some people in our team actually, we get on a jam. It's real fun. But the Stay Puft Marshmallow Man always gets a shout out. I think he's the childs of the eighties. It's the state, they shout it out.

Daniel Stillman:

Yeah, I'm definitely dating myself. Is he a Lego as well?

Barry O'Reilly:

No, he's not.

Daniel Stillman:

No, I was going to say.

Barry O'Reilly:

He's actually a savings. He's pretty cool.

Daniel Stillman:

Oh, nice.

Barry O'Reilly:

Yeah, people love it. Then I've obviously got a, "V for Vendetta," mask because there's something that's quite subsurface about everything I do and contrary. I think if you know anyone who's watched, "V for Vendetta," it, there's a certain type of person it speaks to and I guess I'm one of those people.

Daniel Stillman:

Okay, okay.

Barry O'Reilly:

I kind of love it.

Daniel Stillman:

This is the one of great check-ins that I've done in some of the men's work that I do is the question, "If you really know me, you would know. If you really knew me, you would know." I'm one of those people that, "V for Vendetta," resonates with.

Barry O'Reilly:

Yeah, totally. That's why I've got bee's mask and it reminds me that counterculture taking this sort of path less traveled, all those things that resonate with me in terms of going against the systems, trying to shake them up and innovate them and do something better.

Daniel Stillman:

Yes.

Barry O'Reilly:

That's sort of a lot of the inspiration that I take from the philosophy, if you will, from those types of ed books, films and so forth.

Daniel Stillman:

That's wonderful. So this is actually interesting. You started to tee this up earlier, and this is I think a great place to circle back around. One of my other favorite ways to think about things is the conversation between our past self, our present self and our future self. In the coaching work that I do. I think it's really awesome to hold that space. You started talking about in the beginning of your journey and how you started to... I'm a product person in a technology field. How do you feel like your journey in that started? I'll put this in context. What would that person who at the beginning of his journey, looking at Barry today, how would he understand where you are now? Would he understand where you are? Looking from the beginning to now, would he get it?

Barry O'Reilly:

Yeah. Well, the story is always twists and turns, right? But I think I'm a person who's generally had a clear idea of what sort of vision I wanted to move towards. In some respects, each experience along the way has helped me refine that and get more conviction about it. I started as an engineer, that's what I studied in university. I was a software engineer, I just sucked at it. I would do it for five days a week and one day I would have a flow day, if you will, where I really enjoyed it. But four days of the week, I hated it. I was just banging my head against the wall. I guess at the time, this is 20 years ago, there wasn't really this notion of product management, if you will. But there was the people who came up with what to build and then the people who figured out how to build it.

And I just naturally, because I was in a startup, we were building a mobile games development company at the time. I just started to get this exposure to figuring out actually what were we trying to build, what would the product look like? What were the features? Who would use it? I just actually started to draw towards a natural affinity in that area rather than actually coding it up. That's how it started for me, to be honest. I didn't really call myself a product manager. I was probably more project manager really in that day because somebody sort of had to get the team organized about what they were going to do. I guess that's more what it was called in those days.

From there it really just moved on to working in the startup was great fun. We built this Tamagotchi-esque type cute pet game called, "Wireless Pets." It was the first game to be where you could, phones were had just got connected to WAP, so you could play distributed mobile games and it just exploded. Then that got the business up and running. Next thing we had Sony, Sega and Disney ringing us up to build computer games for them. I built a, "Lilo & Stitch," game in sort of 2002. It was pretty crazy and it just, when we were just a couple of people outside of Edinburgh and Scotland building these things.

Then from there, it really was just a case of each experience I've had more opportunity to either boat work in early stage building companies right through the working and consulting companies to doing my own advisory around that. I always knew over time that I liked the creation process, figuring out ideas, how they can turn into businesses and how you can build teams to get those things created. So I always love travel. So I've lived now in I think maybe nine countries, and this is my first time living in Asia full-time. I've traveled a lot around Asia, but never had it as my postal address, if you will.

Daniel Stillman:

Yeah.

Barry O'Reilly:

This is such a fascinating place at the moment. The Philippines even in itself is, it's the youngest population under 25s, huge percentage to the country is that. It's got the highest percentage of Crypto wallets in any country in the planet. So there's-

Daniel Stillman:

Wow.

Barry O'Reilly:

Yeah, there's so many unique aspects to this whole region as well as the amazing innovation that's happening in places like Indonesia. 400 million people were onboarded it into the internet in the last nine months in Southeast Asia, which is just phenomenal. So there is just some very unique aspects of what's happening in this region. I'd lived in San Francisco for six years before that. It was a great experience. London for five years before that. So yeah, I guess there's parts of me that's not surprised and there's parts of me that is, but I know I like traveling the world and I know I building things. So here we are having fun trying to do it.

Daniel Stillman:

In a way it sounds, what I'm hearing you say is as we look to where we are now, from where we started, it actually sounds like, dare I say, an unlearning of things or letting go of things that you knew you didn't resonate with, that you didn't like. What do you feel like-

Barry O'Reilly:

That's pretty fair.

Daniel Stillman:

What do you feel like you've had to unlearn the most in order to get to where you are now?

Barry O'Reilly:

I think just not being so hard on myself is probably the first thing. When I was in university-

Daniel Stillman:

Do you have a secret for that, for everyone listening? I don't think it's just me and Barry who are hard on ourselves.

Barry O'Reilly:

Yeah, no. It's crazy. I had some experiences where I put myself in very bad positions because I almost had unrealistic expectations for myself. First example was when I was in university, I got into my mind that I had to do well. I had to get a first or an A1 or whatever the equivalent is in the educational system. I put so much pressure on myself to say, "If I don't get that, I've wasted the last four years. I still remember our final exams had eight exams to do and we were on the fourth exam, or the first three had gone really well. But in the middle of the fourth exam, my mind just went totally blank. I mean I couldn't even remember my own name. I sat there for I'd say most of the actual exam period, just staring at a blank page and I couldn't write words. It was one of these sort of first moments where I'd actually realized I'd put so much pressure on myself that I'd sort of flipped, if you will. I had frozen.

Daniel Stillman:

Yeah, you'd basically choked out enough blood to your brain through stress that you couldn't think anymore.

Barry O'Reilly:

Nothing. It was just one of these moments where it's like, what am I doing to myself? It was really interesting and I still remember leaving the exam hall and walking home, whatever. I spent the rest of that day almost sort of totally removed from myself. That was sort of one moment where I really got a glimpse into, "I need to find ways to manage myself." That was probably one of, at the time very difficult, but also a great learning moment for me. Over time, I think all of us and a lot of people like yourself and others who we've big ambitions, we're trying to do bold things. We like to all get outside our comfort zone and do well. What I remembered is that it's not about perfection, it's about excellence and just how can you show up and give your best rather than have to be the best.

Really the thing you're just trying to improve is with yourself. It's not anybody else.

Daniel Stillman:

No.

Barry O'Reilly:

Just how you can get better every day. That was a huge sort of, at the time I would never have called it "unlearning," but it was these things where I was like, "Right, this is a lesson I've got to really take about myself." I see that a lot even today with whether I'm helping startups, working with advisories or working in our venture studio where there's lots of entrepreneurs trying to be successful and build companies. And they're hard on themselves. There's no two ways about it. So I think that's one of the things that I suppose really stands out to me is just it's about the pursuit of excellence rather than perfection. And recognizing that and giving myself a little bit of not so hard on myself as you shouldn't be either, Daniel.

Daniel Stillman:

Thank you. Well, the phrase, giving your best versus being the best is a really interesting and subtle difference because it is the process versus the achievement. It's being rather than becoming, which people have been talking about that since Socrates and Plato. There's a huge difference. I've been actually reading an essay somebody was writing about a book actually, this idea of mimetic desire. There's a French philosopher whose theory is, I think his name is Gerard, that most of the things we want, we want because other people want them. So we see something and we say, "I want that, or I want to be that." Or the way I think of it is, we're living someone else's story. We want to get that A-level because that means-

Barry O'Reilly:

Yeah, yeah, yeah.

Daniel Stillman:

... that we are something that is good. Where do you feel like you got that from? Was that just general society? Was that your folks? Was that something, where do you think that narrative came from for you?

Barry O'Reilly:

Yeah, no. It's really fascinating. I like to get the best out of myself. Well, and that's something that I've always felt in a strange way, I feel that Judy, both to the opportunities that my parents and family created for me and that I've just been given in this world compared to other people. I was lucky to be born into a situation where I was fed, I was clothed, I was highly educated relative to most of the population of the planet. So I feel like there's a... I've always felt even at that level, there was something that I, either you're meant to do and give back. I also played sports at a really high level growing up. So rugby was my favorite sport. I played it at a really high level and I learned a lot about teams and the values that go into creating something great is as a system, it's a group of components of people working together to achieve more.

It's just such a very unique, I found, or took away from those types of experiences. So I just always felt, for me, that's what it was more about. It wasn't necessarily about trying to beat the person beside me, it's just get better myself. I remember even quite recently watching a great podcast with Kevin Hart and he was talking about this idea too as well. For as a comic and a standup, every night he goes out there and he's just trying to make that show a bit better and gauge the reaction.

And so much of comedy in a way is very like a product. You're testing features of the conversation to your point and seeing what resonates, what doesn't. What gets traction, what makes people laugh, what makes people cry is that what your intended response to your action. So there's a lot of things like that that I just enjoy the process, if you will, of improvement, but in a directed way. And so I think that's something that's always been interesting for me. I generally like things where I have to get outside my comfort zone. If the helicopter is leaving in five minutes, there's a 5% chance of survival and most people aren't going to come back. I kind of grab in the bag and jumping on the chopper. That's my jam.

Daniel Stillman:

Is that a movie? Is that a specific movie reference? Is there a specific scene?

Barry O'Reilly:

I'm in the Philippines, so I feel like it's some sort of-

Daniel Stillman:

On the chopper.

Barry O'Reilly:

... Francis Ford Coppola.

Daniel Stillman:

Get down.

Barry O'Reilly:

A platoon or whatever it might be.

Daniel Stillman:

Probably in our, I'm thinking there's got to be a Schwarzenegger movie or maybe it's, "Alien." It's possible. So now I feel circle around. One of the things that always stumps me, I think when we have something big that we've created is the, "Well, how did that get started?" I think about, "What was the first conversation between Steve Jobs and Steve Wozniak?" They had a conversation. They, this is of course my trope, it's they had a conversation and that conversation grew is it's a meet cute in a rom-com.

They had a conversation, then it became another conversation and then somehow they were making a company. You mentioned before we got started that Nobody Studios, the venture group that you're launching, creating is LaunchED. You have not met these, a lot of these people in person. It's like how does that conversation get started to, I think of it as the old movies where it's like, "Hey everybody, let's put on a show."

Barry O'Reilly:

Yeah, yeah.

Daniel Stillman:

You're putting on a big show. Somebody's doing the props, somebody's got the lights, we've got costumes, there's a script, we're selling tickets. It's a whole show.

Barry O'Reilly:

Yeah, no.

Daniel Stillman:

It's like, "The Muppets Take Manhattan." That's my eighties reference.

Barry O'Reilly:

Yeah, no. It definitely feels like, "The Muppets Take Manhattan." I think that's definitely what the startups can feel like.

Daniel Stillman:

Who's Kermit in this? Who's Kermit in this analogy?

Barry O'Reilly:

I'm trying to remember. I definitely had Kermit as a child, but actually my favorite was Fozzy Bear. So because I like the gags. So that's always there, the one that resonated for me. But yeah, as you say, at the end of I guess 2019, I was living in San Francisco, I'd been doing advising at for probably, I don't know, it felt like independently for maybe seven years. I'd just been working with a few startups and done some advisory seats and it just really reminded me how much I loved building. I was missing building. One of my friends who was with me on one of the companies I worked on, Agile Craft, which we sold to Atlassian, it's like Jira Line now. His name's Lee Degal. Lee was sort of, yeah, he sort of reached out to me and was like, "Hey, I've met this guy, Mark McNally, who I think you should have a chat with him.

He introduced me to Mark and Mark was, literally, I'd never met him before in my entire life. He lived in Orange County, he's done 14 startups and was trying to create this thing called, "Adventure Studio," which the idea being, "Could we create an entity where you raise capital, you have a bunch of ideas, and then you build teams to go after those ideas and try and build these early stage or pre-seed stage companies." Incubate them, fund them, incubate them, support them, and then try and grow them and get them acquired. One of the things that I enjoyed about my time at ThoughtWorks is that you would work on lots of different projects and lots of domains. And one of the things I liked about advising was that you'd be helping teams as they build businesses. So I just felt like this was the perfect crucible for me to bring all my skills to bear and actually create equity in something.

Beyond that though, to the, "V for Vendetta," we sort of had this idea that venture is so locked up. It's a place that most people don't really get access to. Often, you have to be a high net worth individual to even invest in early stage companies. So one of the other things that Mark had mentioned is this notion that he was going to try and crowdfund the financing of this startup in a way where anybody, whether they were retail investor, which means everyone from a bus driver to a nurse, a restaurateur would be able to own a piece of this company. So we would, if you will, give access to more people to bring their talent, their influence and their capital to an entity where they could help build startups that are going to have a massive impact on their future. So the mission was fascinating.

The constructs was perfect. I did a call with Mark's when he's sitting in his garage and he had a really sort of to your point about what's in the back of your phone calls, he had this really perspective sign that just said, "Nobody Studios," on it. I was like, "Man, I love this name first of all. He's like, "Yeah, because, "Nobody," we park your egos at the door just people might have done lots of things, but we're trying to create something together." I just had a huge amount of resonance with one another. Yeah, we spent the next three or four weeks talking to each other and really just talking about the vision for what, "Nobody," could be and the values that it would have to represent that started the conversation where Mark had been in his own journey to reflect on his career and figure out what he wanted to do in the second half of his career, if you will.

I was just looking to start putting my energy into something that would create something much longer and lasting than me, create equity for myself and for putting energy in. Then something that could have a real impact, social and economic impact for people that were involved. So it just ticked all the boxes. Here we are two years later, we're on a mission to do 100 companies in five years. We've got 11 in development, four in the market. We've just launched our crowdfunding, which very kindly you are an investor as well. So welcome to the Nobody.

Daniel Stillman:

I think of myself as a symbolic investor, but I wanted to be part of the-

Barry O'Reilly:

No man.

Daniel Stillman:

Part of the journey.

Barry O'Reilly:

No, you are. Yeah. That's what, you're a nobody, that's what it's all about.

Daniel Stillman:

I've always wanted to be a nobody. Now I am.

Barry O'Reilly:

Now you feel the counter-culture when you say that.

Daniel Stillman:

Yeah.

Barry O'Reilly:

That's why we love it. It's like people joke, they spend so much time trying to be somebody to become a nobody and here we are. It's [inaudible 00:32:28].

Daniel Stillman:

I just want to give my best versus be the best.

Barry O'Reilly:

You know it, brother. That's it. That's exactly it. Yeah, it's just been super fun. Here we are now, the campaign is live. We're ticking over raising half a million dollars. We've got a couple of hundred investors from people all over the world. It's been amazing and we're only getting started. So it's super fun times and hopefully there's like people listening here who might be interested and go and look at thinking about what they want to become a nobody too.

Daniel Stillman:

Yeah.

Barry O'Reilly:

I'm nobody. Who are you? Maybe you're a nobody too.

Daniel Stillman:

What do you feel? So we're in this moment where I'm hearing the weird Al Yankovic song, "Dare to be Stupid." You have to put all your eggs in one basket, but that is what you're taking the things you know and instead of advising seven or so companies disparately, it seems like the concept of a venture studio is trying to achieve some sort of nuclear fusion. That there is some sort of sustaining heart of innovation, that there is a way that... Because I'm new to the concept of a venture studio. You and I had a conversation offline where you're like, "Anybody can start one. You could just be two guys in a garage." But if it's a good venture studio, I presume there is some knowledge, resources and approaches shared amongst companies. What-

Barry O'Reilly:

Yeah, no.

Daniel Stillman:

... do you feel like that beating heart is of a venture studio?

Barry O'Reilly:

Yeah. So it is very much an emerging asset class. A lot of people have felt, if you will, that especially over the last few years, the valuations of startups have just gone crazy. These friends of mine, even in San Francisco were getting funded millions of dollars with just a pitch deck and not even a prototype. It was blowing my mind that a lot of the checks and balances have just disappeared from the system in some respects. And VCs have a lot of capital that they need to deploy, are paying high prices for startups that have not really sort of if you've validated or proven that they've got traction. So one of the ideas really was, "How do we get back to doing things a little bit more frugally about creating companies?" So at Nobody, we invested about a quarter of a million dollars to incubate companies over 12 months.

The idea is that we're taking it, something from a post-it note to a prototype to a working product. That when it sees sort of traction in the market, then we would go to get an external capital and funded. So it's sort of a part of the ecosystem we believe that has lost it, maybe a little bit of its natural built in checks and balances. So we think that we can create very high quality early stage startups that have to go through a sort of a quality bar, if you will, to make sure that they're performing before we either keep investing in them or we look for external folks to invest in them. So it's real fund that we have our own ideas that we work on, we've identified or met some early stage founders who might have ideas or early prototypes and have come into the studio.

It's been really fascinating to bring all these people into a collaborative portfolio. This is probably a little bit of a difference from a superpower if you will, that a venture studio has. It's because all the companies in our portfolio are essentially, everybody in each individual company earns equity in the company they're working in, but they also earn equity in the studio as well. So they're collaborative. In many, many respects, and that's very different from a typical venture capital portfolio because they might have three analytics platforms or two food delivery products, so there's competition, if you will.

Daniel Stillman:

I see, yeah.

Barry O'Reilly:

But in a studio it's collaborative. Also we have this notion of building blocks. So there's companies that are in our portfolio that we use to build companies on top of. A simple example is Thought Format, it's a serverless, no-code platform. We build another one of our products ovations, which is a virtual events platform for speakers and emerging talent on top of that no-code platform. So these businesses sort of first customers if you will, were each other. So they can learn faster, hire trust, iterate quicker, and they have really good conversations at one another to improve both of their products. So there's some natural little superpowers that we have in the studio that aren't necessarily available to typical venture capital portfolios, incubators or accelerators like Y Combinator where it's basically a competition, right?

Daniel Stillman:

Yeah.

Barry O'Reilly:

All great, all great picks, three companies to win. So it's not collaborative. So that's why we've tried to bring our mix to having raising capital that we can invest in ideas, people bringing their talent that they can help build ideas, and then us bringing our capabilities to help those founders build faster and be more successful quickly.

Daniel Stillman:

So given that everybody's remote, going back to the beginning of our conversation around three person dinners and serendipity salons. In the same way that Google Sprint, the Google Sprint style that lived inside of Google evolved and grew over time as part of many conversations, collaborations and people committed to growing that community effort. What are the mechanics for creating that collaboration? If we were to look under the hood?

Barry O'Reilly:

Yeah, it's hard.

Daniel Stillman:

How do we structure it? Yeah.

Barry O'Reilly:

One of the things I probably have learned along the way is that asynchronous communication is a skill. It's a skill that even pre-pandemic most people didn't have. Even through the pandemic, I don't think a lot of people learned good practice of it. I think everybody was waiting for it to end. So one of the things I think we learned very early when we were starting to build this business is that the discipline of writing things down, of having a clarity and almost standard operating procedures about how you run meetings, how you capture notes, how you communicate afterwards, where do you put content that you want for discussion and feedback? How do you make sure that people are engaged? How do you reach folks? Some people like to be on Slack, some people like to be on WhatsApp, some people like to read emails still. There's so much coordination about conversation design, which actually made me think a lot about the work we did in your workshop to be honest.

These simple things like readmes. I remember we did this and your workshop too, you made us draw shield to represent different parts of us. These sorts of and techniques are so powerful when new people join a company that if I've like a read me file, it's like, "Read me. I'm Barry. I live in Manila. These are the hours I like to work. This is the best way to communicate with me. Here's if you need any documents. This is the style of my meeting deed, here's my phone number."" All of these small little things have such a huge impact when you're working remotely and asynchronously because it's not like you bump into people in the hallway and go, Hey, oh, you're in my department too? Cool. We all sit together. We'll go for lunch." So you have to create the signposts and you have to create the content to help people collaborate successfully. That's been one big aha. I think that, yeah, I'd be curious for your thoughts on what you've seen through that time.

Daniel Stillman:

I mean we're talking about in a way hygiene.

Barry O'Reilly:

Man. We talk about tidying up all the time. Tidy as you go. Every so often it's like we got to clean the he. It's like, but it's really, it's like honestly.

Daniel Stillman:

That's what great chefs do. Great chefs tidy as they go.

Barry O'Reilly:

Damn right. I always remember one of my, so two of my family are chefs and one of my friends always says, "The sign of a great dinner party is that when you arrive and the person is still cooking and they're cleaning the kitchen as they go." That's the ultimate chef. I was like, "Yeah, okay. Cool." But it's so true because this stuff can get un-wielding very, very quickly. And I think that's one of the things that's certainly learned along the way is every so often we have to clean up all the Slack channels. All the orphan channels that have got the same, Nobody town hall, Nobody hall town, Nobody water cooler, Nobody, Nobody. You're like, "What are these things?" Because people come to the company, people go from the company and when they join and there's confusion about where to go, these are always good signals that you don't have good information architecture if you will. And you're not moving information around.

Daniel Stillman:

So that's like, that's platform. I guess one of the things I'm thinking about is structures or mechanics of connection versus a person or people who are those connectors?

Barry O'Reilly:

Yeah. Well, so I think the third person we hired in the company was Thacha Thacker is the Chief Culture Officer. She was actually an employment attorney who got so frustrated with having to defend people in courtrooms that she was like, "I need to go upstream if you will and see if I can address this problem further in the value stream if there is that thing." She was one of these things that we talk a lot about because one of our values is irrationally global and the team are from-

Daniel Stillman:

Irrationally global?

Barry O'Reilly:

Global. Yeah. The team is everywhere. I'm in the Philippines, we've got people in Hong Kong, Singapore, Israel, Dubai. We got people in Italy, Dublin. We got London and all the Americas. We don't have anyone in Africa and Antarctica yet. That's our goal is to get a team set up there, but already we've got a hundred plus Nobody's all over the world, which means our meetings are instantly global. So this morning we were doing our portfolio review and I had to get up at 4:30 AM or it was at 4:30 AM my time. So I had to get up at 4:00 AM and that is the way to try and get a portfolio review where you can cover Asia, Europe, the Americas and Africa. People have to flex. So it's fascinating as well just recognizing how to work both remotely, across different geographies and cultures because what works in downtown New York in your neighborhood is very different from how people respond in London and [inaudible 00:44:20].

Daniel Stillman:

You know how we do downtown as we said.

Barry O'Reilly:

Yes. Yeah, exactly. Right? It's been fascinating again to see that sort of culture emerge and find ways to communicate. Yeah, no. It's a work in progress as always. But I think that and the advent of video, we use a lot of video.

Daniel Stillman:

You mean like asynchronous video?

Barry O'Reilly:

Yeah. So we do a lot of everything from live streams to tools like Loom where you can record five minutes and send it to people.

Daniel Stillman:

Loom is amazing.

Barry O'Reilly:

So it's really fascinating that how important the gesture goes with the commentary if you will. Because especially when there's a lot of feedback on prototypes, mock-ups or the ability to put video with sound is really quite fascinating. Even in our hiring process as well, we ask people to create a video and talk a bit about their inspiration. Why they found the studio, what inspires them about it? Because it's a huge part of how we communicate with one another. Yeah, so it's fascinating just trying these little experiments as you go along.

Daniel Stillman:

So one other thing I'm curious about is I've been doing a series around co-founder relationships and similarly to you and your relationship with your co-founders at Nobody Studios, each company is got their own conversation of, "Oh, this is what we're doing, this is why we're doing it." They have their internal conflicts as you're saying, "Going up the value change to understand how do we build the company that each one of those people has their own opinion about, the type of company that they want to build."

Barry O'Reilly:

Oh yeah, for sure.

Daniel Stillman:

One message I heard that I'm wondering how you communicate to each of your founders is this balance between giving your best versus being your best, versus running on fumes and creating systems. Because it's not sustainable to.

Barry O'Reilly:

No, not at all. Right. The fascinating thing about Nobody is, so I'm a co-founder of Nobody Studios, but we're also co-founders of all the companies we create. We're not an overlord looking over these portfolio companies with judging them. We're actually co-founders of them with them. So there are kids too. We want them to be successful. So even that dynamic between, if you will, the CEOs of the NewCos and us as co-founders of those businesses is fascinating to consider. But to your point about managing expectations and just energy, because that is what I have found is so important. In the earliest stages of starting companies is a huge lift. It's all the energy to turn the flywheel is manually created by just you showing up, trying to do as much as you can. Push the boulder up the hill if you will. It will always want you to be pushing it.

You have to learn how to self-regulate. This is again, another really strong lesson I learned even going back to this, your point about when I sitting there in university thinking, "Oh, I've got to work the most," or, "I've got to show up the most." Or, "I can't miss a meeting," or. It's easy for people sometimes to fall into that trap. I see it in myself, our team and our founders, but we're also one of our other values is people first in the studio. We constantly, you see the team check in with it one another and go, how are you doing? How's your energy?

Did you have a meeting last night that finished at 10 o'clock and now you're on a call at 4:00 AM? What's going on? Are you okay to do that? There's empathy there. That is because we are irrationally global, the sun does not set on the studio. There is somebody up working at high velocity somewhere all the time pinging you on asynchronous communications if they're blocked. So one of these notions of setting boundaries and having systems is imperative. One of the things I've made an intentional investment about is exercise.

So I literally book time in my diary, just like a meeting, where I go and train. Some of that training is I enjoy mixed martial arts, so I get a trainer to come to my house and we train in the house. Or else if I play sports rugby, I love playing rugby, I play that. These things are systematically built into my schedule that forced me to do them.

Daniel Stillman:

Yes.

Barry O'Reilly:

I actually invest in paying for a trainer because it makes me do it. If I just had a meeting in there saying, "Exercise," nine out of 10 times I'll take another meeting. Because it's just the exercise time.

Daniel Stillman:

Right. The system, the accountability to another person like the change of context. This is really, really true.

Barry O'Reilly:

It's amazing. Right?

Daniel Stillman:

Yeah. What other systemic approaches would you suggest to co-founders getting started to make sure that the Boulder pushing part and the next phase, which is running after the boulder, I presume on the other side of the hill.

Barry O'Reilly:

Yeah, we're getting there.

Daniel Stillman:

Because there is that part where you're running after the boulder and you're like, "Oh, we have to hire people and we have to suddenly be more capable of in things that we never thought we had to be capable of.

Barry O'Reilly:

Yeah, no. We're there. We're there right now at the moment. Yeah, because again, it is relentless. The demand for energy never goes away. It's all there. So I have to really be intentional about managing my energy, setting those boundaries, putting systems in place like exercise and what I eat, when I eat. One of the companies we're building is actually with Dr. Gina Poe. She's one of the leading researchers on sleep and dreams in the world. She runs the sleep lab at UCLA, previously at Harvard. This is one of the fun things about working in a studio, Daniel, because health and wellness is a big part of the studio. We've loads of ex UFC fighters and all these what I would call, "High performance bio-hackers." It's just hanging out with these people. You suddenly are like, "What?" So Gina Poe has been teaching me about sleep and it's, I am now, I will not for hell or high water sacrifice not getting a minimum of seven hours sleep every day.

So just as for men, especially if you're getting six hours or less sleep of hours a day when I'm in my early forties now, I would have the equivalent testosterone rate of a man in his mid fifties. Which is, and this is huge because in order to the two leading indicators for longevity and high quality of lice, what the muscle mass is one of them, your ability to actually maintain your strength if you will. The other is the qualities of sleep that you get. So I'll just sit there going, "These are the leading researchers in the world who have been studying this for 20 years and they're telling me these things. So if I don't design them into my approach to getting better and managing myself, if you will, and I'm not listening to the lecture, if you will." And-

Daniel Stillman:

Yes.

Barry O'Reilly:

So it's all a design to me. I know you enjoy this too as well. It's a design problem.

Daniel Stillman:

It is a design problem.

Barry O'Reilly:

Then if so, I can experiment. I can, all these simple things that I have become quite focused around. Because if you want can put on biometrics like a whoop or aura ring and you can see the difference when you get less sleep, when you eat, aren't exercising when you aren't. So those have become real core tenants of me managing my energy so I can give that energy both to myself and the teams that we're working with. So we're all our best. Sure there's times where you stretch and you flex, but that cannot be sustained. I think we're good as co-founders recognizing that in one another and saying, "You should take a week off, you should not take those calls in the afternoon."

You should... You're wedded to these people because you're trying to do something totally irrational. Like a startup is totally irrational. You have an idea that to try and build something from nothing, does anybody want to join me in doing that? It's, there's a 5% success rate actually lower than that. So I think we've really become friends though you go way past colleagues because you live in people's lives together to create this. It takes that much energy and I think that's one of the things we've been really good is taking care of one another.

Daniel Stillman:

That's beautiful. I love the idea that earlier you were talking about the synergistic effects of companies within the portfolio utilizing platforms and it sounds like sleep quality is going to be a new foundational component of-

Barry O'Reilly:

Yeah, SleepCloud. Check it out. It's coming to an app store near you soon.

Daniel Stillman:

Well, and if anybody's listening, so my hack, by the way, Barry has been at many people suggested keeping my phone plugged in another room. Because reading the phone before bed does not help you go to bed.

Barry O'Reilly:

Nope.

Daniel Stillman:

I have a brown light e-Ink tablet that I read fiction on before bed and-

Barry O'Reilly:

Nice.

Daniel Stillman:

... and blackout curtains. They're the best.

Barry O'Reilly:

There you go.

Daniel Stillman:

Those are my hacks.

Barry O'Reilly:

Yeah, well that's it. But it's all part of the design and I, like that. That is, if you asked me these questions 10 years ago, I would've been like, "No, the way I relax is I have a glass of wine, I do these things. I stay out late or I unwind my friends." But as I've evolved both physically myself and as I get older, but also just being more in tune with, these are the things that help me be at my best. I get frustrated if I don't show up as I know I can.

I think that's being, again, a learning part. I wouldn't tell myself 10 years ago not to go out, have fun and have a white, red wine. That has shaped me to who I am today. Absolutely. I think it's just, I've learned that for the tasks that I'm trying to do today, there's the way they help me be my best requires changes. Those things like exercise, sleep, diet, and also this idea of, to your point about serendipitous conversations, I work from home. So every two weeks I go out and meet someone new for lunch.

So I go and experience like being with people here that I've never met before, whether it was in the Philippines or in San Francisco. I do those things because they give me a change of mode. They give me a different way to look at the world and meet new people. So I try to be as intentional as I can thinking about the things that have helped me, both systematically and serendipitously and work them in. Yeah, hopefully I keep persisting with that and it's working for me as far as I can tell. I think it is.

Daniel Stillman:

Well, this is continuous improvement. We have to notice.

Barry O'Reilly:

Right on.

Daniel Stillman:

We have to be intentional experiments and intentionally noticing. "Oh yeah, that works." I mean there was a guy who hilariously tried to do the sleep pattern that I think it was like Leonardo da Vinci did this thing where he would sleep for 90 minutes every... Or he'd spread out his sleep schedule and he did something. He totally, he was maybe the original biohacker and it worked for him and a guy tried it and he was like, "I don't actually, turns out I don't have enough creativity to fill all the time that Leonardo da Vinci did." So I'm going to go back to it.

Barry O'Reilly:

Well, here's a tip for you man, that as Gina Poe has discovered that there is a rhythm to sleep cycles and surprise, surprise, guess what the time is?

Daniel Stillman:

What? I couldn't...

Barry O'Reilly:

It's 90 minutes.

Daniel Stillman:

Is it really? Wow. Leonardo. Biohacking to the truth. Well listen, I, it's very late where you are. You've had a long day. Is there anything I have not asked you that I should ask you. What haven't we talked about that we should talk about?

Barry O'Reilly:

No, I just, I've enjoyed catching up as much as sharing some of what I've been trying to do and hearing more of what you've been up to as well. So yeah, thank you very much for having me on the show. It's always a pleasure to spend time with you and I welcome as well to the Nobody Network. I'm looking forward to again, to you come and talk to all our portfolios about designing great conversations. I think one of the great parts of building these companies is every nobody can bring their talent, their influence and their capital, and you've abundance to bring in all of those things. So I appreciate you very much and thank you very much for supporting us and being part of the Nobody journey. I think it's going to be a pretty fun adventure.

Daniel Stillman:

So where should people go to learn more about being part of, because there's just one month left. When this comes out, it'll be less than a month.

Barry O'Reilly:

Oh, great. Yeah, right.

Daniel Stillman:

To be part of the crowdfunding part of things. Yeah, well after that what can they do?

Barry O'Reilly:

We may never raise funds again, so this might be the only time we ever do it. So yeah, please go to republic.com/nobodystudios and there's lots of information. You are buying securities, so don't be surprised. We have to go through the same level of, if you will, sort of rigor as a SEC regulated IPO in some respects. So yeah, be, go have a look at what we've shared. If you've any questions we're constantly doing live streams. Ask me anything open, Q and A, so you can find that on at Nobody crowd, pretty much everywhere in all your favorite social platforms. Thanks again for having us.

Daniel Stillman:

Thanks for making this time, Barry. I know your system was like, "Daniel, none of the times on your podcast schedule match Manila time." I'm like, "Good point." That is a solid, solid point because my working hours are usually, I know that I'm not usually my best at 7:30 in the morning. That's my a [inaudible 01:00:34] experiments.

Barry O'Reilly:

Well you have been today experiment. Thank you very much for that.

Daniel Stillman:

Well, when you texted me and you're like, "Can I have 10 more minutes?" I'm like, "Yes, I will enjoy my shower now." Because I was about to run in and run out. So thank you for giving me an extra 10 minutes. I really appreciate it, Barry.

Barry O'Reilly:

Thank you. Appreciate you too. Thank you very much.

Daniel Stillman:

Well then we'll call scene. I think we can successfully do that.

Barry O'Reilly:

Nice.

Conscious Collaboration: Co-founder Conversations

In this conversation, I sat down with Beth Bayouth and Mario Fedelin, the COO and CEO (respectively) of Changeist, a non-profit organization dedicated to youth empowerment. They are building a community of young people that utilize their personal agency to create a more just society. 

Changeist’s programs help 11-26 year olds learn a common civic language, engage in dialogue, and build community to investigate local and global social justice issues. Participants also work with other local community-based organizations to implement local solutions to local problems.

Together, Mario and Beth explore how they met, built a relationship and decided to work on this project together…and how they continue to manage themselves and each other in the entrepreneurship journey.

A few insights we’ll unpack about conscious co-founder relationships:

  • The key to a great co-founder relationship is that both of you do not fall apart at the same time!

  • Fighting Well and how Cofounder Intimacy can help: With cofounder intimacy, there is an understanding that often there’s something else behind a conflict or a mood. Because when you're close, you tend to know about what’s going on or that it’s safe to ask.

  • Knowing yourself and your skills

  • The Power of working with someone with a Different Skill Set but Similar Values 

On Knowing yourself and your skills, and finding compliments on your core team: 

A great leadership team requires Comfort with yourself and your skills and Respect for the skills of others... and it takes Balance - but Balance of what?!

On a leadership team you need:

+ Architects and Visionaries

+ Multipliers - someone who brings something you do not have to the table, who is also committed to the vision and the journey

Another way to think about this is that you need:

+ A Balance of Openers and Closers on the team.

This is the essence of conscious collaboration - knowing if you are more comfortable in a generative or divergent mode, ie, opening, or are more natural in the “Synthesizer” role - organizing, closing, or planning towards action. Mario owns his limitations as a “closer” and intentionally chose Beth as a COO for her natural “shark” skills - her ability to move things forward with clarity.

Mario and Beth also talked about their balanced styles in “Speeding up”  and “Slowing Down” creative conversations - Beth will pump the brakes and ground ideas in reality when the time is right. Feeling that balance between creativity and clarity, speed and thoughtfully slowing things down, is the essence of conscious creativity and conscious collaboration…being comfortable with both opening and closing modes is critical, but collaborating with others who complement your natural approaches is powerful.

Be sure to check out my other co-founder conversations. I discussed building an Integrity Culture with the co-founders of Huddle, Michale Saloio and Stephanie Golik, and investigated prototyping partnerships with Jane Portman and Benedikt Deicke, co-founders of Userlist. (Which Mario and Beth absolutely did, as well!) 

I also sat down with Jennifer Dennard and Dan Pupius, the co-founders of Range to unpack Healthy Conflict in Cofounder relationships. Conflict and collisions will inevitably happen in relationships, so you might as well learn to lean into it!

You may also enjoy my interview with Carolyn Gregoire and Scott Barry Kaufman, the co-authors of the 2015 bestseller, Wired to Create, where we unpack how they managed their working relationship and discuss Paired creativity, which is totally a thing!

And if you really want to dive deep into the idea of being a conscious co-founder, make sure to check out my conversation with my friend Doug Erwin, the Senior Vice President of Entrepreneurial Development at EDAWN, the Economic Development Authority of Western Nevada.

Links, Quotes, Notes, and Resources

Changeist

On Healthy Conflict: https://theconversationfactory.com/podcast/managing-healthy-conflict-co-founder-conversations

Minute 19

Daniel Stillman:

And I'm wondering how, in those early days, the first week you decided to draw a boundary around this is what we're going to do, this is how we're going to work together. What was it like establishing your roles, your boundaries, your relationship in the early days? If you can remember back that far.

Beth Bayouth, COO:

I know, I am trying to remember back, it felt like it was more about... I think at that point we knew who we were as individuals and what our skills were. The boundary of who does what sort of naturally formed.

In the first month, I wrote our business plan obviously with the help of Mario who had already ideated a lot of... Understood who our competitors were, understood all of that. We applied for fiscal sponsorship through community partners. I think that stuff came easy and then it was just so much work. I don't know that we were super intentional about the relationship side of things right away because it was like, let's get the business plan, let's get fiscal sponsorship. As soon as we got fiscal sponsorship, we launched a crowdfunding campaign. That's just a lot of work. We wanted to show bigger institutional funders that we had this backing of individual supporters that really wanted this thing to happen. We raised in the first two months, then we raised 25,000 in a crowdfunding campaign just from friends and family and folks who had experienced the program that this had jumped off from.

Minute 21

Daniel Stillman:

I'm curious, what's your relationship like now? What is it? How do you work on your relationship these days?

Mario Fedelin, CEO:

I mean, I talk to her more than anyone. I talk to Beth more than any other person. If we rewind, there was this vulnerability, maybe there was... I'm going to say when we go back to that first conversation. I was very scared and I felt like I had put myself in a position to where I needed to find a way forward or else I was going to have to eat a lot of shit. I was going to have to go back on my word or I was going to have to tell people because I was just in a really tough place and I had no idea how to move forward. I think you're giving it too much time Beth that conversation, I feel like I asked you in the first 10 to 15 minutes, I was like, would you be interested? One, there was this built-in comfortability.

We've been friends prior. I have a lot of respect for Beth in the work that she had done and where she was at in her career. I knew that I was in safe hands and I trusted that and I had to be really vulnerable of saying, I don't know how to move forward and I really need help.

Minute 27

Daniel Stillman:

Tell me about that Mario. What does it mean to fight well for you?

Mario Fedelin, CEO:

I mean, we disagree on things. We'll get heated and we're both very... We have very strong opinions and...

Beth Bayouth, COO:

Passionate.

Mario Fedelin, CEO:

... We're very passionate about the things we're passionate about and so we'll fight. It's so funny too, sometimes it spills out into in front of our staff members or we'll just go back and forth and oftentimes it's one of us apologizing after we got done like, sorry, did I go too far? Look, we could figure this out. Or we apologize quickly. It's not hard to know when we're like... Also, we know each other's ticks so I know when Beth is really hurt personally or really upset about something and that trigger like I'll stop or we'll close it and then I'll be like, okay, I think I'll apologize. Then, we'll move past it pretty quickly. We're not afraid to confront that. We were arguing about something or we disagreed about something, let's sort it out. It's never personal. [inaudible 00:28:00].

Beth Bayouth, COO:

No, and it's interesting because we had mentioned all the personal side of things and I remember when I first entered the working world, you hear these things from your elders or whatever, don't share too much with your boss. Don't bring your personal life into work. It feels like that stuff isn't very effective. I think lots of times if one of us is overly affected by something that happens at work, it's largely there's something personal happening in our lives that I just can't handle this today. The fact that we're able to talk about all of that very honestly, it just makes for a better working relationship. We try to encourage our entire teams to... We try to make sure that people know that there aren't boundaries like that within our organization because I think we just know it's more effective for everybody to understand each other.

Minute 35

Beth Bayouth, COO:

I also though think to your other part of the question of what has happened to create that space for us, I think it's not just the personal side of things. I think we over the years have also just built trust, working trust in each other. I think we have both displayed that we are doing what we need to do for the other person to feel comfortable. I think along with Mario's vulnerability in the beginning of being able to say where he had shortcomings and moving this thing forward, he also had to really lay his trust in me that I was going to hold his vision dear and work as hard as he needed somebody to, to help make it happen. I know that that took some time.

I had to prove that I was there and I probably had to even take some time to really get there myself too. I think that just over the years we've been able to do that. That's why if I'm freaking out about something, I also know Mario's got it. It's time and time again, we've pulled through and it maybe was the last minute, but I think that we've built that working trust as well.

More about Beth and Mario

About Beth

In her role as Chief Operating Officer, Beth oversees the fundraising, operations, systems, and strategic planning for the organization. Prior to her work with Changeist, Beth received a MBA from Boston University with a focus on social impact. She then moved to Los Angeles to take on Local Control Funding Formula (LCFF) at Los Angeles Unified School District, helping to create new ways for teachers, staff, and stakeholders to better understand the complicated financial policies affecting LAUSD students and communities. Beth is committed to strengthening communities and empowering young people. She is a proud AmeriCorps alumna of City Year Chicago and in July 2017 was honored with City Year’s highest alumni recognition, the Comcast NBCUniversal Leadership Award.

About Mario

Mario spent over a decade in the national service movement with City Year. There developed and oversaw civic leadership programs for youth in three different markets. In 2014 he conceived of, designed, and launched Changeist.

Mario is currently a Board Member and Advisor to multiple community organizations in Los Angeles, a graduate of SCLN’s Leadership LA, recognized by the LA Empowerment Congress as a top 40 under 40 Civic Leader, and serves as a Senior Fellow for USC Marshal School of Business, Brittingham Social Enterprise Lab. In 2019, he was chosen out of thousands of applicants from over 160 countries to be an Obama Foundation Fellow. The Obama Fellowship supports outstanding civic innovators from around the world to amplify the impact of their work and inspire a wave of civic innovation.

Full Transcript

Daniel Stillman:

I am so grateful, Mario, Beth, that you are here to have this conversation about what it means to be a conscious partner in running a business together. I'm so excited you're here. Welcome aboard to the Conversation factory.

Beth Bayouth, COO:

Thanks for having us.

Mario Fedelin, CEO:

Thanks for having us.

Daniel Stillman:

Thank you very much. So Beth, I'm going to start with you. What's the origin story? How did you two come to work together in this big, crazy, topsy-turvy mixed up world? How did you two find each other and start working together?

Beth Bayouth, COO:

Sure. Mario and I met way back in 2005. We both started our careers as AmeriCorps members, happened to be working for the same organization but in different cities. I was in Chicago, he was in Philly. We both became staff members and were leading Saturday civic leadership development programs for middle school and high school youth. The organization brought us together. There was about a team of 10 of us nationwide who were all working on these programs and they wanted us to think through really what the overall learning outcomes were, how we could make sure that we were learning from each other and making each of those programs in the cities as best as they could be. We met then and that's sort of where our friendship and professional relationship started.

Daniel Stillman:

2005?

Mario Fedelin, CEO:

I also [inaudible 00:01:42] those times.

Beth Bayouth, COO:

You were young.

Mario Fedelin, CEO:

I was like this younger kid too who totally undereducated. I feel like I was a little bit in over my head in Philadelphia, how I landed there. At least that's how I felt. Beth, along with a couple other folks who had their degrees and they had been working on these programs, I was kind of trying to figure out how to navigate those dynamics of someone who's undereducated and someone who's educated and trying to do something together. It was an interesting start to the relationship.

Daniel Stillman:

So Mario, what brought you to AmeriCorps?

Mario Fedelin, CEO:

I found, again, it was a little bit of an accident. I guess the way that it starts is I grew up on the east side of San Jose. Had an opportunity for... And that's in the California suburb some people, it's called the South Bay. I had a teacher who, my brother had some challenges in high school, but everyone really liked him. As I came into that high school, people were like, oh, that's what's-his-name's little brother and so I think people kind of wrapped their arms around me a little bit. I got sent to a camp. Camp happened [inaudible 00:02:56] Santa Cruz Mountains and I had this really amazing camp counselor who was a brown kid that looked like me, but was very different than the other brown kids I ever met. Now, his name was John and we just had a blast for a week and that was a week in the Santa Cruz Mountains where we talked about, at that point they called the tolerance.

It was really diversity and racial justice and all those sorts of things. Anyways, fast forward, I graduated from high school, I had this adventure out, not going to college. When I came back to San Jose when I was 20 years old, I was transferring a expensive coffee shop chain. I was transferring from San Diego up into San Jose. Randomly as I was walking down, one of the alleyways [inaudible 00:03:42] San Antonio in downtown San Jose. I saw these random people walking that had these jackets on, these yellow jackets and it instantly, it was like, oh, my homeboy John used to work for that company. Maybe I could work with kids. That seems pretty cool because I didn't really have a plan. I walked into that recruiter's office and just so happens that they were hiring AmeriCorps members and at that moment, so it was a real quick start turnaround and I interviewed and I got placed on this diverse team working on civic leadership programs on Saturdays in my neighborhood. That's how it all kind of happened.

Daniel Stillman:

That's amazing. John's jacket was like...

Mario Fedelin, CEO:

The jacket, the symbol. It was a symbol.

Daniel Stillman:

That's amazing. The power of a symbol, the power of a properly chosen color.

Mario Fedelin, CEO:

It was less about... The color wasn't the indicator, it was a personal relationship that flagged it. I think that's the important thing to remember is we have our brands and our powerful brand narratives [inaudible 00:04:45] it would've never had the same meaning if John wasn't compassionate and the way that we exchanged ideas together and made me feel like I was a whole person in those moments. I mean, I had never spoken to him since and now it's been... We're looking at more than 27... 25 years later. I can still tell you his name. It's the person.

Daniel Stillman:

That's amazing. That connection. Beth, what brought you to AmeriCorps?

Mario Fedelin, CEO:

That's the power of youth workers.

Daniel Stillman:

Yeah.

Mario Fedelin, CEO:

That's the power of youth workers and the power of connection to people.

Daniel Stillman:

Yeah. Yeah. Sorry for cutting off there. But yeah Beth, I'm curious, what was your turning to AmeriCorps as well?

Beth Bayouth, COO:

Very different. I kind of had a very traditional path. I was supposed to go to college after high school. I did that in a pretty misguided way. I had no idea what I was doing there. What I wanted to do. Ended up majoring in business because it was practical. That was the only thing I could really think about getting out of the college experience other than I was a leader in clubs and the social aspect and living on my own and that kind of thing. When I graduated I didn't see myself doing anything business related. I didn't understand what I could really do with that degree that was going to appeal to my passions and what I had been doing thus far with volunteer work and everything. I had a friend who'd done an AmeriCorps program and was like, I think you'd really like this. I thought, well that sounds good. I've always worked with young people.

I was planning on moving to Chicago and it was a really good opportunity. It lined up with my timeline. I got in there and I was working in Chicago public schools and my whole family are public school teachers and I think I had been fighting whether that was supposed to be my reality. I was like, well this will be a good test run. I'm in the schools every day getting to see what it's like. Very quickly decided that that was... Definitely, I was right. That was not going to be my path, but I loved working with young people outside of school. I loved having that... The real relationships that you could build and thinking about how you supplement the school day and the academics with things that young people are really curious about.

Daniel Stillman:

That makes a lot of sense. I can really understand loving the content of education, but changing the context is really beautiful. 2005 to 2014, how did you get the band back together? What was the spark getting... I mean, because Changeist was 2014, but although I imagine it may have started a little bit earlier in your brain, Mario. Do you want to talk a little bit about the origin story of Changeist and then how you two wound up together and in the roles that you have in the company?

Mario Fedelin, CEO:

Yeah, so I was still working for that agency. That same organization, it's called City Year, but we had... I started in 2003, four we met in 2005. I became one of the guys who was working on the Saturday leadership programs for high school students. Beth and I worked even closer when we were working on the high school program because she actually had me come out to Chicago and work with her and a group of practitioners to thinking about starting a Chicago-based high school program. The organization had an opening in Los Angeles and so they brought me out in 2007 to launch their civic leadership programs down here and so that's how I landed in LA. It was really just as I was hitting the 10-year mark at that agency, I was tired.

I think I had a really tough year with just a little bit of burnout. I ended up having to close those civic leadership programs in 2011 because the organization wanted to focus, which ultimately was the right decision for that organization, but I had to help close down those nationwide and that all of our work that we had done together felt like it just got put on the shelf and benched when it was really the first program that agency had really put into standardization, which Beth and I were a part of. It felt like a little bit of waste, but I ended up retooling and just going straight into the education space with the organization and working on school campuses with principals. Then, I just wasn't that into it. I was organizing on school campus. That was the fun part where I was trying to raise money through school budgets and it wasn't exciting.

Looking at math scores and English scores for individuals just wasn't really what I had ever signed up for. Again, because I didn't go to college, I had these really big holes and gaps in knowledge and practice. Through those years when I was in LA I was volunteering for other agencies and boards and trying to develop my acumen. One of the organizations that I was working in was a program in South Central and mixed with this kind of itchiness to move on to something new and being with my partner watching this culminating event through one of the organizations that I volunteered for really part-time on the operational side, I just was like, you know what? I could do that. I could do that on my own and I could probably do it very differently and do something bigger. I just had that kind of itch.

It was that moment, at that culminating event on a college campus and then me and my partner went to go watch a movie and we got on one of the trains and I was seeing these kind of rec centers off the train that were beautifully kind of... Had art and graffiti on it. I was just like, I could do something bigger and different than what I'm doing now. Had some mimosas and I started Spouting off what I wanted to do because I had recently also had a bunch of young people come back. After those program closed, about three years ahead of that they started coming back in their senior years and saying, "Hey Mario, I'm running this thing for my school. Do you have any tips on how I could run this service project?" There was about three or four of them that came back that year also so now you have my own discount or my kind of burnout with these old students that were coming back for tooling up. And so they needed me for something and then me figuring out what the self-discovery looks like and seeing a gap in the youth workspace and my life partner when we're having a conversation, I was kind of throwing out this big picture idea of consulting for kids. I think it was the original version of it. She was like, "Yeah, you should do that." I was like, "I should do that."

Daniel Stillman:

That does sound like a mimosa. Talking a little bit.

Mario Fedelin, CEO:

Yeah, it was definitely mimosa. Got all very excited about it.

Daniel Stillman:

But supportive, which is really good.

Mario Fedelin, CEO:

Yeah, right. Then she told me, she was like, and we can live with my mom if you want, we could figure this out together. I was like yeah, we should do that. Then, on Monday it still sounded like a good idea. That Monday I told my boss at that point and I was like, I'm going to leave here. I'm going to give you some time. I can't leave now, but this is going to be my last round and I want to start a non-profit. To their credit, that agency City Year and the people there were just like, hell yeah, we'll help you do it however we can help.

Then, I started down the journey of figuring out, well what kind of team can I put together? And I got all of my favorite people that I'd worked with in the past in LA together and started taking one day a week off at City Year to think about big picture stuff and think about what this program would be. And I started these meetings with folks and just started to build. And Beth wasn't part of that yet, but that was the early days of 2013 I'm assuming that I started putting the stuff together.

Daniel Stillman:

That's amazing. And so Beth, what was your experience like coming into Changeist? What did things look like when you stepped in?

Beth Bayouth, COO:

Yeah, so after leaving City Year as a staff member, I took a couple years and then I went back to school and ended up getting a master's in business so business was the right choice, happenstance. That experience brought me out to... That was in Boston and I ended up doing a fellowship that brought me out to LA for a summer. Working with LA Unified and... First, it started my love for Los Angeles and I was really excited to try and come back once I finished my master's and I was able to. In summer of 2011 I moved out to LA permanently and was continuing the project that I got that fellowship with. I was working with Los Angeles Unified School District on what's now their local control funding formula and was working in the district office. I did that for a couple of years and just felt a bit disconnected.

I was really missing the vibrancy of that feeling that you would get with organizations like City Year and working on something. I definitely am a behind the scenes type of worker, but also I like being able to be close to the young people that we engage with. I was looking for something new. Mario got sort of stuck where he was at, I would say, is that fair?

Mario Fedelin, CEO:

Very Fair.

Beth Bayouth, COO:

And a lot of folks... We had people in common, we had friends in common and it got into Mario's ear that I was looking for something new. He was like, can we go get some coffee? I think it was like 45 minutes into reconnecting and he was like, you want to help me start this small nonprofit? And I was like, yeah, let's do this, let's do this again. I took a few weeks and talked to my husband about it and thankfully he's in tech startups, so was kind of like, yeah, this is your turn to do a startup. Let's see how it goes. Talked to a couple of our mutual friends and was just like, yeah, Mario's been working on this. I've been working on it with him. This is legit.

Mario Fedelin, CEO:

I mean, also she really was more like, "Sure, that sounds cool." I don't know if it was as optimistic conversation because that was like, "Oh shit, is she really going to do this?" And then she goes back to all of our friends. I also hear, and so she's talking to everyone to make sure I wasn't full of crap and make sure that we actually had some foundation of thought put into it. Then she committed and she's like, I'll do it. I'm in until October. It's like, I could do this until October. This was a meeting in what? Was it in April? We had this conversation?

Beth Bayouth, COO:

Yeah, March or April.

Mario Fedelin, CEO:

Maybe March.

Beth Bayouth, COO:

I think I said, I'll give you six months and see if we can raise some money.

Mario Fedelin, CEO:

I was like, all right. Technically, Beth was the first person to work on Changeist full-time.

Daniel Stillman:

Wow.

Mario Fedelin, CEO:

Free. I mean, also what we got... Where we had gotten was we had worked with this group. I had called them our architects and they had really helped put shape to this thing. At the point when I was in probably February, I thought that we had some pretty cool stuff lined up. This seems like we could do this. I could actually right now go get some young people, we could launch this. But my job was ending at City Year. I had no personal money, I was crap at saving money personally. We weren't able to get that together and I had no way to raise money because we had no 501 C3 and no financial back, no kind of infrastructure. That was the stump point. This is where we like to say that... People were in my ear about Beth being on a job hunt, but also her LinkedIn spammed me. I was like, oh Beth. I got this random email from LinkedIn and I was like, oh yeah. I was like, of course. It's a sign because someone just said Beth's name and now her LinkedIn is... Said add me to your network. That's kind of how we reconnected.

Daniel Stillman:

This is the moment inside the moment and I want to zoom in because this is the first conversation. There's coffee and there's an agreement to a limited experiment to see where things could go. And I'm wondering how, in those early days, the first week you decided to draw a boundary around this is what we're going to do, this is how we're going to work together. What was it like establishing your roles, your boundaries, your relationship in the early days? If you can remember back that far.

Beth Bayouth, COO:

I know, I am trying to remember back, it felt like it was more about... I think at that point we knew who we were as individuals and what our skills were. The boundary of who does what sort of naturally formed.

In the first month, I wrote our business plan obviously with the help of Mario who had already ideated a lot of... Understood who our competitors were, understood all of that. We applied for fiscal sponsorship through community partners. I think that stuff came easy and then it was just so much work. I don't know that we were super intentional about the relationship side of things right away because it was like, let's get the business plan, let's get fiscal sponsorship. As soon as we got fiscal sponsorship, we launched a crowdfunding campaign. That's just a lot of work. We wanted to show bigger institutional funders that we had this backing of individual supporters that really wanted this thing to happen. We raised in the first two months, then we raised 25,000 in a crowdfunding campaign just from friends and family and folks who had experienced the program that this had jumped off from.

Daniel Stillman:

I'm curious, what's your relationship like now? What is it? How do you work on your relationship these days?

Mario Fedelin, CEO:

I mean, I talk to her more than anyone. I talk to Beth more than any other person. If we rewind, there was this vulnerability, maybe there was... I'm going to say when we go back to that first conversation. I was very scared and I felt like I had put myself in a position to where I needed to find a way forward or else I was going to have to eat a lot of shit. I was going to have to go back on my word or I was going to have to tell people because I was just in a really tough place and I had no idea how to move forward. I think you're giving it too much time Beth that conversation, I feel like I asked you in the first 10 to 15 minutes, I was like, would you be interested? One, there was this built in comfortability.

We've been friends prior. I have a lot of respect for Beth in the work that she had done and where she was at in her career. I knew that I was in safe hand and I trusted that and I had to be really vulnerable of saying, I don't know how to move forward and I really need help. I think when Beth says that we knew who we were, it was like I knew what I was really good at and I knew that Beth was in a much different place and there was overlap in some of that stuff. In a lot of ways I didn't hire some... I didn't hire or we didn't sign onto something where we were both going to be having the same type of skill sets. It was like Beth is... Beth is a little shark and I needed someone to help push the ideas forward because I was the one who was throwing everything out on the wall and Beth was able to ground it and plant it. That is still the case in our relationships is I'm the one that comes with the ridiculous idea and Beth's like, that's dumb. And I'm like, you're right. That is dumb.

Or I give the idea and she's like, yeah, that's a good one. Then [inaudible 00:23:11] gives it life and brings it to life. We talk all the time. I mean, we've been through a lot together in the last nine years. It's like family deaths, a pandemic, to emotional [inaudible 00:23:27] relationships, childbirths. We have two kids that were born including one that was the very first four months. Let me tell you this story. I think we're in office [inaudible 00:23:38] in the first three months of this happening. I think we just got our money, maybe. So we're going to a presentation or something [inaudible 00:23:47] and she was like, I have something to tell you. I'm pregnant. I'm like, okay. And I'm like, oh man, is she going to walk away? Then, it was fine because we were like, yes, we're building this to be a family thing, so of course we'll figure this all out.

Then, the real pain came in is when six months hit. It was October, November and we still had no other money except for that 25,000. I'm like, how did I walk this friend into a shit storm who is about to have a baby and we have no financial security and this is going to fall apart. I was really scared. I remember sitting on my bed crying to my... Actually, physically sitting there crying on the bed after having a conversation with Beth where Beth was not upset about anything at all, but I was just so scared that I wouldn't be able to get us on payroll. She wouldn't be able to have things she needs to support her family as she gets started on that journey. There was no prospects, but Beth was steady. She was like, it's fine, we're going to get through this. Then, a month later we had $200,000 show up and a bunch of things that we had talked about with friends out and then just all just showed up and came together.

Daniel Stillman:

I'm sitting here and I'm pulling these threads together in my mind from an appreciative inquiry lens. What I'm hearing that is alive and powerfully functional in the way you two relate. One is just a human foundation, having known each other, having worked together there is the ability to be vulnerable with each other, which doesn't come... Is nontrivial. That doesn't come for free. That's something that's earned. The other thing that I'm hearing, the fourth thing is that you both have a sense of who you are, you know what you are good at, and you also know and respect what the other person is good at. There's that space to have the other person step in and the two things that I'm hearing, this is something in the design world, we talk about opening and closing or divergent and convergent. Sometimes people are divergers and convergers. Mario, you're a really good diverger, and Beth, you're a really great converger. The fact that you have, if both of you were divergers, it would be really, really hard. You need a closer, everybody needs a closer. Then, underneath all of that seems to be a very strong undercurrent of respect, which is all really powerful. Is there anything else that you feel like is alive in your relationship that I missed or that we haven't talked about yet?

Mario Fedelin, CEO:

We fight really well.

Daniel Stillman:

Tell me about that Mario. What does it mean to fight well for you?

Mario Fedelin, CEO:

I mean, we disagree on things. We'll get heated and we're both very... We have very strong opinions and...

Beth Bayouth, COO:

Passionate.

Mario Fedelin, CEO:

... We're very passionate about the things we're passionate about and so we'll fight. It's so funny too, sometimes it spills out into in front of our staff members or we'll just go back and forth and oftentimes it's one of us apologizing after we got done like, sorry, did I go too far? Look, we could figure this out. Or we apologize quickly. It's not hard to know when we're like... Also, we know each other's ticks so I know when Beth is really hurt personally or really upset about something and that trigger like I'll stop or we'll close it and then I'll be like, okay, I think I'll apologize. Then, we'll move past it pretty quickly. We're not afraid to confront that. We were arguing about something or we disagreed about something, let's sort it out. It's never personal. [inaudible 00:28:00].

Beth Bayouth, COO:

No, and it's interesting because we had mentioned all the personal side of things and I remember when I first entered the working world, you hear these things from your elders or whatever, don't share too much with your boss. Don't bring your personal life into work. It feels like that stuff isn't very effective. I think lots of times if one of us is overly affected by something that happens at work, it's largely there's something personal happening in our lives that I just can't handle this today. The fact that we're able to talk about all of that very honestly, it just makes for a better working relationship. We try to encourage our entire teams to... We try to make sure that people know that there aren't boundaries like that within our organization because I think we just know it's more effective for everybody to understand each other.

Daniel Stillman:

That's really interesting. In a way, so there's two things I'm hearing. Mario fighting well means recognizing when you've crossed a line, knowing how you're affecting the other person, apologizing quickly if need be. I think there's another piece of this, Beth, which is knowing that if you are getting under each other's skin, it's because there might be... There's often something else outside of the work sphere that is affecting things. Because you're close, you tend to know about that or that you can ask about that. We're not going to be watching this so they're both nodding right now in sync even though they're in two different places, which is amazing.

Beth Bayouth, COO:

Yeah. I can recognize, oh I am feeling really strongly about this, but you know what, it's because my daughter's sick or it's been stressful at home or something and I can take a step back and be like, Mario, let's... Can we just table this conversation? And it's welcomed. It's understood.

Daniel Stillman:

Yeah.

Mario Fedelin, CEO:

I also point out too, I think it's... We've rarely both been in a place of instability at the same time or we both handle things... Whenever I'm like, we're not going to finish in the black and I'm freaking out over something, there's always this sense of calm. Whether it's intentional, or unintentional from Beth to be like, look, there's an out here. And vice versa. Beth is on the verge of freaking out about something that's happening. I'm like, I'm not that worried about it. Look, we're going to be fine. We've been in lock sync. I think that's been kind of one of the things where it's been... Whenever it all feels like it's falling apart, Beth never believes it is. That has helped us get through this. That's really hard to find, I think in a collaborator.

Beth Bayouth, COO:

Yeah, we're definitely able to balance each other.

Daniel Stillman:

I've heard...

Mario Fedelin, CEO:

How many times has this organization fall... How many times has this organization felt like it was about to fall apart completely? And one of us is just like, look, we'll get through this.

Daniel Stillman:

So the key is both of you not fall apart at the same time and somehow it just doesn't happen?

Beth Bayouth, COO:

It has not happened yet.

Mario Fedelin, CEO:

And we've gone through a global pandemic, so who knows what the threshold's going to be. If it wasn't for Beth, this would never have happened. There's no way.

Beth Bayouth, COO:

I mean, you had the idea.

Mario Fedelin, CEO:

Yeah, but it was nothing without having some grounding and some [inaudible 00:32:17] and that came through what you brought to the table. And I don't know that... I don't know that I would've had a different collaborator. I don't know that a different collaborator would've helped me weather all this stuff.

Daniel Stillman:

Beth, good job on taking a compliment. I know for myself it's a skill that I under-utilize. I'm much better at batting them away.

Beth Bayouth, COO:

Yeah, it's hard, but I'm working on it.

Daniel Stillman:

It's a thing. Well, speaking of working on things, what do you feel are some of the challenging parts of your relationship that you've had to work through? What comes to your mind when you say Hmm Beth?

Beth Bayouth, COO:

It doesn't ever feel challenging.

Daniel Stillman:

Yeah.

Beth Bayouth, COO:

I'm sure there are. I'm sure I'm just missing something here, but nothing ever feels like we can't talk about or we really overstepped.

Daniel Stillman:

Yeah. What do you feel... So there's this phrase that I've heard some folks use, which is that everything is workable. There's this container here in your relationship where things can be discussed. I guess what I'm curious about is what has enabled you two to create a space where you feel safe to work through what you need to work through?

Mario Fedelin, CEO:

History. I don't know, context.

Daniel Stillman:

History and Context.

Mario Fedelin, CEO:

Friendship.

Our partners know each other. Our kids play together. How I live down the street from her for a year in that same complex. I think maybe if I'm picking at what's hard, at least... There hasn't been a problem yet, but I do wonder what does our future look like, and how long can we do this for? And what happens when one of us is ready to walk away? Being able to allow the other person grace to do that. I think that's something I'm thinking about in terms of our relationship is like, it's going to be tough because life is changing, it's almost going to be a decade. We got to be able to allow ourselves to grow. Although, I keep trying to pull Beth into other collaborations. I want to start another business with her. I'm like, how about we do this? How about we do that?

Daniel Stillman:

That's interesting.

Beth Bayouth, COO:

Again, I slow it down.

Mario Fedelin, CEO:

That's something to think about. How does it end? Beth is not my life partner, so we're not married. That means that this is... At one point, this relationship is going to come to an end because I can't imagine us running Changeist forever together. That has to be a concern or a thoughtful because we have so much mutual respect for one another and a deep friendship. I can imagine how it would be much harder to say goodbye or to say I got to go. I mean we, I don't know. Beth's probably like, "Nah, it's cool." She'll tell me. When do we say now it's time and not have resentment for the other person walking away?

Beth Bayouth, COO:

Yeah, I agree with that. I also though think to your other part of the question of what has happened to create that space for us, I think it's not just the personal side of things. I think we over the years have also just built trust, working trust in each other. I think we have both displayed that we are doing what we need to do for the other person to feel comfortable. I think along with Mario's vulnerability in the beginning of being able to say where he had shortcomings and moving this thing forward, he also had to really lay his trust in me that I was going to hold his vision dear and work as hard as he needed somebody to, to help make it happen. I know that that took some time.

I had to prove that I was there and I probably had to even take some time to really get there myself too. I think that just over the years we've been able to do that. That's why if I'm freaking out about something, I also know Mario's got it. It's time and time again, we've pulled through and it maybe was the last minute, but I think that we've built that working trust as well.

Daniel Stillman:

If you were talking to young entrepreneurs at the beginning of their journey now, what kind of advice would you be offering them to build the kind of relationship, the kind of longevity that you two have had?

Mario Fedelin, CEO:

I think with entrepreneurs, at least the stuff I've heard or read is always [inaudible 00:37:59] the only ship that sinks the partnership. I don't know if you've heard that, is don't do things together with another person.

Daniel Stillman:

I have never heard that.

Mario Fedelin, CEO:

I don't know if maybe I'm being the wrong things... There is a school of thought that's like, you go alone and then bring people in. I would take the advice of someone... The founder that City Year told me it was just find a partner. Someone that could vouch for you and someone you trust and someone that will always say that you're doing well to another person when they ask about you. So that you could weather some of the tough storms through the entrepreneurial journey. Because it's tough. Again, all the hard stuff is always about personal fear. I feel like all the things that we've ever had... Weather that have been seemingly dire or real consequential were personal ego or self insecurity and of being at the table or knowing what to say. Everything else is learnable and manageable. Being able to have another person help you, whether that stuff personally, I think that's made this thing float. Finding that other person, and it can't just be anyone, it's got to be someone that has a different skill set, similar values that's willing to go through it with you.

Beth Bayouth, COO:

And you have to be able to admit that you have to have enough trust in them that you can admit when you don't know what you're doing or you're wrong or you're scared because otherwise it's not a relationship worth having.

Daniel Stillman:

Well and it's also to what you were just saying, Mario, if these things are learnable, if we aren't willing to say that we don't know them, it's hard to learn them.

Mario Fedelin, CEO:

Yeah, [inaudible 00:40:01].

Daniel Stillman:

Uh oh, did I freeze or did Mario freeze?

Beth Bayouth, COO:

Mario froze.

Mario Fedelin, CEO:

Oh no, I froze.

Daniel Stillman:

Oh, you're back.

Mario Fedelin, CEO:

Oh no, I froze.

Daniel Stillman:

Just say whatever... Just say whatever you said exactly the same way.

Mario Fedelin, CEO:

I was just saying the myth... I think the myth around the entrepreneur side of stuff is like, it's not the technical stuff that's hard. That's the easy part. You could always figure out the technical stuff. There's always someone you could bring in. There's always someone to talk to, to help you through this thing, this finance report or raising money or building this. That stuff is easy. You find anyone could do that. The hard part I think is having the strength to endure and that's where a friend comes in.

Daniel Stillman:

So we're amazingly getting very close to the end of our time. Beth, what haven't I asked you about having a powerful relationship as two folks running the core of a business? What haven't we talked about that we should have talked about?

Beth Bayouth, COO:

Sometimes, I wonder how does our partnership come across to the rest of our team?

Do they think we have each other's backs, even if we're totally wrong? That kind of thing. I'm curious, and I don't think we've ever really talked to anybody on our team about it, but I wonder how it affects everybody as a whole. We've never explored it. I don't know how... We'd probably have to do some sort of external consulting to find out, but I would like to think that it's helpful. I would like to think we're modeling how we want everybody to operate or how they support their own teammates, but we don't know.

Daniel Stillman:

That's a really interesting question. And hearing the two of you talk about the quality of fighting well and I was like, oh, I wonder if that trickles down. I'm curious about that too. And that would be really interesting to learn about for sure.

Mario Fedelin, CEO:

Especially, because we're the bosses, so you're the boss in those spaces. Then, when we both start going at it, I imagine people are like, oh, this is awkward.

Beth Bayouth, COO:

I mean, let's be fair, we're not fighting, we're just disagreeing.

Daniel Stillman:

Yeah, yeah.

Beth Bayouth, COO:

But we're both very blunt. When we're delivering a disagreement to each other, we know we don't have to sugarcoat it. If other people are present, maybe that feels uncomfortable. I've never received that feedback, but I can imagine that that could be.

Mario Fedelin, CEO:

I could imagine.

Daniel Stillman:

Well, for the two of you, with the folks that you manage, do you feel like you conduct yourself in a similar way that the quality of your conversations are similar?

Beth Bayouth, COO:

I think we both are very clear that we are open for feedback and discussion and really want to understand how people are feeling, but there's still the dynamic of supervisor and employee, especially with folks who might be newly entering a career and really figuring out what can they really do and say, I think, you see different levels of what that looks like with other relationships.

Daniel Stillman:

Yeah. And it seems like the two of you really relate to each other as equals, which is really powerful.

Mario Fedelin, CEO:

Yeah.

Daniel Stillman:

Well, I really appreciate you two taking the time to be so reflective and vulnerable and real. These are such wonderful qualities to notice in a high quality partnership. I'm glad that you two have been able to create that for each other and especially in service of the mission that you two are serving. That's awesome.

Mario Fedelin, CEO:

I couldn't ask for a better partner.

Beth Bayouth, COO:

Same.

Daniel Stillman:

Well, that seems like a great place to call scene.

Managing Healthy Conflict: Co-founder Conversations

In this conversation I talk with Jennifer Dennard and Dan Pupius, the co-founders of Range, software that helps teams be more connected, focused, and productive no matter where they’re working. Global teams at Twitter, New Relic, CircleCI, and more keep their teams in sync and connected with Range.

Jen is the co-founder and COO. Prior to founding Range, Jen led Medium’s organizational development team. Jen has partnered and consulted with startups and multinational corporations on empowering autonomous and distributed teamwork. She lives in Colorado with her two cats and husband.

Dan is co-founder and CEO of Range. Prior to Range, Dan was Head of Engineering at the publishing platform Medium. And before that he was a Staff Software engineer at Google, where he worked on Gmail, Google+, and a variety of frontend infrastructure.

He has an MA in Industrial Design from Sheffield Hallam University and a BSc in Artificial Intelligence from the University of Manchester. In past lives he raced snowboards, jumped out of planes, and lived in the jungle.

This is a fairly meta conversation (in the old sense of the word!) since we talked about how Dan and Jen structure their relationship and how they built their company…which is a company that builds software that structures relationships - specifically, effective teams.

As Dan outlines, “Human behavior requires structure to facilitate it…in an organization, software provides a lot of architecture, which shapes our behavior, but we're (often) not intentional about that software. The whole theory of Range was… how can we build software that acts as architecture that shapes the behaviors that we believe to be present in effective teams?”

My book Good Talk is built around the idea of a Conversation OS, or Operating System. 

One element of the Conversation Operating System is error and repair. As Jen says in the opening quote, conflict and collisions will inevitably happen in relationships.

Dan suggests that “if you have productive conflict or if you encourage productive conflict, there will be times when you step over the boundary and it's what you do then that is the important thing, in how you recover.” In other words, how you repair the error or breach in the relationship is often more important than the error itself.

Many folks shy away from conflict, or hope it never happens. Planning for it and knowing it will happen is a fundamentally different stance, a more effective Error and Repair Operating System.

I also love the “reasonable person principle” that Jen and Dan use in their relationship, as long as it never slides into gaslighting.

We unpack a lot more great stuff, from uninstalling Holacracy at Medium to the importance of being journey-focused in entrepreneurship relationships, and the power of crafting explicit processes ahead of needing to use them.

Dan and Jen are also big believers, like me, in the power of the “check-in''. For example, in my men’s group we share in 30 seconds how we're doing emotionally and physically at the start of every group. At Range, it can be as simple as a “green, yellow, red” check-in or as deep as going straight to the question “how are you…really?” 

They suggest that baking human connection into each and every meeting is much much more effective than trying to isolate connection into one “vibes” meeting.

As with many of my co-founder conversations, there is a common thread of clear roles along with an awareness of and respect for the Venn diagram of skills between the co-founders.

Another common thread, as Dan says at the end of our conversation: looking after yourself and attending to yourself is key, because “if you're not in a good state, you can't be a good teammate and you definitely can't be a good leader.”

Be sure to check out my other co-founder conversations. I discussed building an Integrity Culture with the co-founders of Huddle, Michale Saloio and Stephanie Golik, and investigated prototyping partnerships with Jane Portman and Benedikt Deicke, co-founders of Userlist. 

You may also enjoy my interview with Carolyn Gregoire and Scott Barry Kaufman, the co-authors of the 2015 bestseller, Wired to Create, where we unpack how they managed their working relationship. Paired creativity is a thing!

And if you really want to dive deep into the idea of being a conscious co-founder, make sure to check out my conversation with my friend Doug Erwin, the Senior Vice President of Entrepreneurial Development at EDAWN, the Economic Development Authority of Western Nevada.

Links, Quotes, Notes, and Resources

Range

Lawrence Lessig’s Pathetic Dot theory

Daniel Coyle’s Belonging Cues: Belonging cues are non-verbal signals that humans use to create safe connections in groups. The three basic qualities of belonging cues are 1) the energy invested in the exchange, 2) valuing individuals, and 3) signaling that the relationship will sustain in the future.

Kegan’s Levels, specifically, Stage 4 — Self-Authoring mind

Lead Time Chats

Minute 8

Jennifer Dennard:

Part of why we chose to do a company was thinking about the journey and not the outcome, so startups are very unlikely to succeed, statistically. And so I think it can be similar when thinking about a conversation. Instead of going into it saying like, "This is what I want this person to say or do at the end of it," it's more like, "How do I want to feel during it?" And like, "How do I want the experience to be for both people?" And I think that's kind of how we think about conversations, but also more broadly, as a company, like, "What's the experience? Cool. Are we still having fun? Are we enjoying the adventure?" Certainly there are downs amongst that, but I think part of what has made us successful as a founding duo is that we are in it for the journey versus any specific moment or specific outcome, which I think can be really hard to then deal with the journey, which is quite long.

Minute 9

Daniel Stillman:

Well, so now we get into the point of the story where the beginning can seem organic and emergent, and then at some point, you do start to have that question of, as you said, Jen, values versus tactics alignment, right? And how are we going to do things around here, right? Building the culture and the process of how we're going to do things. How do you feel like you have managed that conversation of aligning on how to align?

Dan Pupius:

Yeah, to some extent, this aligns with the whole purpose of Range in the first place, which is that I think human behavior requires structure to facilitate it. Part of the inspiration for Range is from Lawrence Lessig's pathetic dot theory, that human behavior is manipulated by the forces of laws, markets, norms, and architecture. And in an organization, software provides a lot of architecture, which shapes our behavior, but we're not intentional about that software. So the whole theory of Range was about, how can we build software that acts as architecture that shapes the behaviors that we believe to be present in effective teams? So we kind of like thought about the processes ahead of the problems, so what's our cadence of work? How do we communicate? How do we run meetings? How do we talk about things? And just really thinking about the architecture of which we set things up.

And I think we're not super dogmatic and we're flexible, but I think it's something to fall back on.

Minute 17

Daniel Stillman:

I've heard this before, that some clarity around roles and division of labor is really helpful. Otherwise, there can be unclarity, for lack of a better word, but it seems like the other side to the coin is also true, which is flexibility to pass things back and forth and to shift and alter who's doing what is also really powerful. I'm curious how you navigate that conversation.

Dan Pupius:

Well, I think, we have a Venn diagram, so there's the stuff that's clearly mine and clearly Jen's, and then the middle bit is the messy bit. And luckily, there's not too much there, though that's probably the most critical part of the business for the last 18 months or so, so lots of back and forth on marketing and sales, for example, but it means that we still have these areas, where's it's just very clearly our areas of expertise, where we get to have mastery and complete autonomy. And then it's really the messy middle where we go back and forth. I think if it was all messy, that would be really difficult, or if only one of us had areas of specialization, that would be really difficult as well and probably really disempowering.

Jennifer Dennard:

Yeah. A lot of the decision of who takes something usually relates to bandwidth, and that's both time available but also energy. Sometimes Dan or I will take something just because other person's like, "Oh, I cannot keep doing that," or I don't quite have capacity. And I think that's maybe another thing that we haven't talked about yet in this conversation, is we have invested in through process and tried to cultivate a sense of, I think, safety and belonging on our calls, on how we work together. And that allows me, for instance, to say something like, "I just had hip surgery two weeks ago," and to be like, "Hey, my pain level before or after that is really high. I'm just not able to be what you might consider a normal capacity for me." And Dan [inaudible 00:19:21] hear that and, at least my experience of it, to not feel blamed at all, just to be like, "This is a fact about the bandwidth that we have as a collective system." And I think that allows that kind of handing off of responsibilities in a way that doesn't feel contentious.

Minute 27

Dan Pupius:

But, yeah, if I'm sleep deprived, I will be a bit sharp and I will step over the boundary of what is safe conflict, right? And that could be a catastrophic event if we didn't have that foundation. So I think that's kind of what's interesting, is that if you have productive conflict or if you encourage productive conflict, there will be times when you step over the boundary and it's what you do then that is the important thing in how you recover.

Daniel Stillman:

Jen, what do you do when Dan gets a little sharp?

Jennifer Dennard:

Usually, I pause. Like Dan kind of knows as well, I'll be like... I look away and I'll be like, "Okay, let me..." And then I usually try to pull out what it is underneath, like what is he trying to say or what's the best interpretation? I think something Dan maybe came up with at Medium or we started using there was the reasonable person principle and the idea that whatever the person's sharing, there's a reasonable explanation. And so I think I probably... Took me some time, probably... So Dan at Medium was more my mentor, I would say, and so to come into a co-founding, peer relationship, as a woman who's also younger, I think it took me probably the first few years to really step more into like, "We are peers." And I distinctly remember Dan going out on a very abbreviated paternity leave, unfortunately, at the start of the pandemic. And I was like, "Oh, Dan doesn't know what he is doing either. He just comes up with an answer when I ask, and I can do that."

And I think feeling like a peer in those conversations, to the point we were talking about earlier with power dynamics and stuff, really changes how sharpness lands. It doesn't feel personal. It feels like Dan didn't get enough sleep last night. I think, if it ever starts to feel personal, I also feel comfortable being like, "I'm going to step away from this call. I don't think we're being productive." And we've done that here and there and instead come back together. And I think knowing that, just like any relationship that when you have conflict, even if it does go into a space you're not comfortable, that you have the ability to repair, in my mind, matters because you're never... Whether it's your founding partner or a friend or a spouse, you're never going to not have conflict, unfortunately. And so [inaudible 00:29:24] that you can, typically make it productive, and then when it's not, that you can repair and talk through whatever underlying issue, that feels important to me. And I think we have that really shared understanding

More about Jennifer and Dan

About Jennifer

Jennifer Dennard is the Founder and COO of workplace collaboration software company, Range. Global teams at Twitter, New Relic, CircleCI, and more keep their teams in sync and connected with Range. Prior to founding Range, Jen led Medium’s organizational development team. Jen has partnered and consulted with startups and multinational corporations on empowering autonomous and distributed teamwork. She lives in Colorado with her two cats and husband.

About Dan

I'm Dan, an English software engineer and entrepreneur who lives and works in San Francisco.

I am co-founder and CEO of Range, where we believe that healthy companies aren’t simply better places to work, but do better work. We build software that helps teams be more connected, focused, and productive no matter where they’re working.

Prior to Range, I was Head of Engineering at the publishing platform Medium. And before that a Staff Software engineer at Google, where I worked on Gmail, Google+, and a variety of frontend infrastructure.

I have MA in Industrial Design from Sheffield Hallam University and a BSc in Artificial Intelligence from the University of Manchester. In past lives I raced snowboards, jumped out of planes, and lived in the jungle.

Full Transcript

Daniel Stillman:

Jennifer, Dan, I'm so excited you're here to join me on The Conversation Factory. Thanks for making the time in your day.

Dan Pupius:

Yeah, thanks for having us. Excited to be here.

Jennifer Dennard:

Yeah, thank you.

Daniel Stillman:

So, all right, Jennifer, you made a very, very reasonable request. When I think about conversations, turn taking is one of the most fundamental and easily identifiable ways to manipulate a conversation for good. And it actually turns out that if women speak first, it's actually best for groups in general, according to my experience, for whatever reason. I'm not sure why that is, but it is, in fact, the case. So-

Jennifer Dennard:

We've heard-

Daniel Stillman:

What's that? I'm sorry.

Jennifer Dennard:

We've heard similar things, that encouraging certain people to speak first helps create a more equal and inclusive conversation.

Daniel Stillman:

Yeah. So Jennifer, I'm wondering if you can kick us off with the question of how you and Dan met and decided to start working together on this company. I'm curious what your version of the story is.

Jennifer Dennard:

And do they match?

Daniel Stillman:

And do they match, right? We should have had this as a double blind interview, really. That would be...

Jennifer Dennard:

So Dan and I met when we were both working at Medium, the blogging company. Dan was leading engineering and his team had actually set up a regular set of meetups or talks, a way of engaging with the community, and I ended up being a guest speaker at one of the events. And so a bit later, I actually ended up joining Medium full-time on the people operations team. And Dan and I ended up partnering a lot on organizational design. So Medium had been using something called Holacracy, which is a specific way of operating that I'd say Dan and I are pretty values aligned with, maybe less tactically aligned with the implementation of. And so Dan and I were partnered with designing a new system as it had been... Medium was moving off of Holacracy. And so we worked a lot together on a tool, internally, to really help the company operate, to showcase what people were working on, and it's, in many ways, a precursor to what we do today, but like company, Medium had ups and downs. And Dan and I were often supporting one another during those ups and downs.

Jennifer Dennard:

And so during one of those downs, I would say we were talking and Dan came in and he was excited. And I was like, "It's a hard week. It's not really an exciting time." And he was like, "Okay, but do you think, generally, we could build better tools to support companies beyond just Medium," and taking what we were learning with the tool that we were building there, and the things we were seeing about how companies operate, and where things broke down to really help other companies? And from there, we just went back to work, but a little bit after that, Dan and I had both left Medium at that point. And Dan was starting to think about starting a company and ended up chatting with me about whether there'd be interest in starting something, like Range, around building tools to support teams and companies and being more effective in their operations. And yeah, it really stemmed from our experience working together at Medium and seeing some of the problems that different companies faced.

Daniel Stillman:

Dan, what would you add to that story? What's missing, from your perspective?

Dan Pupius:

Yeah, I think that's accurate. Yeah, I think, basically, as I was looking around things to do next, leading other teams, bigger challenges, I just couldn't imagine working in a traditional company again and using the traditional tool sets, so I was like, "Well, if I'm going to staff a team to build tools to help us actually work better together, maybe I should actually evaluate whether that's a real opportunity." So I met with investors and then met with Jen and it kind of just... I don't know. It wasn't a decision point. It almost felt like it just gradually happened, and before we knew it, we had a company we'd incorporated and then raised some money and built a team, and it just kind of... I don't know. It felt natural and there wasn't a discreet moment where we were like, "Okay, let's do it." Maybe Jen remembers differently, but I don't really remember the specific decision point.

Jennifer Dennard:

Well, I remember you were actually very specific and intentional on like, "This doesn't have to be a specific decision moment. You can take time and think about whether you'd be interested in starting a company. It's a big decision," which I think was a precursor to some of the ways that we work together now, but it felt very egoless and felt very, like, "I'm not going to be offended if you don't want to do this crazy thing called a startup." I think that level made the conversation much easier and much more of a natural progression, where we got to keep talking more deeply, and then eventually do the official parts around it.

Daniel Stillman:

What was that word that you said, equalist? I couldn't-

Jennifer Dennard:

I don't know if it's an actual word, egoless, like [inaudible 00:05:09].

Daniel Stillman:

Oh, egoless. Yeah.

Jennifer Dennard:

I haven't been subject to too many of these conversations, but I think sometimes when people pitch you their company idea and wanting to work together, if you say no, it can feel very like an attack on them personally, which I get it. It's their company. And Dan approached that very differently of like, "Say yes. Say no. Do what you think is right. Here's some fun stuff to think about." I think he either knows me well or approached it kindly, but the giving me an [inaudible 00:05:37] to think about is certainly a way to get me intrigued about a space.

Daniel Stillman:

It's so interesting because, Dan, I saw you nodding your head. Is there anything else that what Jen said evokes for you?

Dan Pupius:

Yeah. It wasn't intentional. I wasn't scheming of, like, "Okay, how do I get Jen to sign onto this?"

Daniel Stillman:

Well, if you were, you wouldn't admit to it at this point, but fair enough.

Dan Pupius:

Yeah. Yeah, I do have Machiavellian tendencies sometimes, but, no, I think it was just that it is a big decision and I didn't know if there was a there there. And I figured that I needed a team to help me explore that, so started putting the team together. It's like getting the band back together almost because we'd been doing a bunch of this exploration work at Medium. And then we started doing customer conversations, product development, and exploration, and talking to investors and, yeah, it just kind of snowballed.

Daniel Stillman:

It's very interesting because the idea of an invitation begins a new conversation, and there was this in invitational... There was conversations that sort of emerged while you were at Medium, but then there was this moment where you reached out and said, "I'm thinking about this. What do you think?" And it incited another arc of conversations for you all. And it sounds like... It's really funny to think about. This is stuff when I first started thinking about, "What does it mean to design a conversation?" This idea of it can feel like manipulation if you're doing things too intentionally, but you did bring a certain essence, a certain approach to the invitation, which said, "I'd like you to be involved and let's think about it." So I think that's a very interesting moment to look at in the story arc of, "This is a liminal space and it's a generous question." And it sounds like it created a very spacious opportunity for you, Jen, to really step into it intentionally.

Jennifer Dennard:

Yeah, and I think like when Dan says he didn't know if there was a there there... I at least speak for myself and I think this is probably true for Dan as well. Part of why we chose to do a company was thinking about the journey and not the outcome, so startups are very unlikely to succeed, statistically. And so I think it can be similar when thinking about a conversation. Instead of going into it saying like, "This is what I want this person to say or do at the end of it," it's more like, "How do I want to feel during it?" And like, "How do I want the experience to be for both people?" And I think that's kind of how we think about conversations, but also more broadly, as a company, like, "What's the experience? Cool. Are we still having fun? Are we enjoying the adventure?" Certainly there are downs amongst that, but I think part of what has made us successful as a founding duo is that we are in it for the journey versus any specific moment or specific outcome, which I think can be really hard to then deal with the journey, which is quite long.

Dan Pupius:

Yeah, I think we've seen a lot of the power of intention at Medium. So when things worked well and how we laid intentional, explicit processes down ahead of needing to use them, we saw the value in that, and then also we saw when it broke down. So from very early on there, we talked about, how do we prioritize decision making, prioritize ourselves, our families, the founders, et cetera? And then we were very clear about how we want to communicate, our values. And I think some people would probably say that's a waste of time, but I think that sets the foundation and just makes everything easy down the line.

Daniel Stillman:

Well, so now we get into the point of the story where the beginning can seem organic and emergent, and then at some point, you do start to have that question of, as you said, Jen, values versus tactics alignment, right? And how are we going to do things around here, right? Building the culture and the process of how we're going to do things. How do you feel like you have managed that conversation of aligning on how to align?

Dan Pupius:

Yeah, to some extent, this aligns with the whole purpose of Range in the first place, which is that I think human behavior requires structure to facilitate it. Part of the inspiration for Range is from Lawrence Lessig's pathetic dot theory, that human behavior is manipulated by the forces of laws, markets, norms, and architecture. And in an organization, software provides a lot of architecture, which shapes our behavior, but we're not intentional about that software. So the whole theory of Range was about, how can we build software that acts as architecture that shapes the behaviors that we believe to be present in effective teams? So we kind of like thought about the processes ahead of the problems, so what's our cadence of work? How do we communicate? How do we run meetings? How do we talk about things? And just really thinking about the architecture of which we set things up.

Dan Pupius:

And I think we're not super dogmatic and we're flexible, but I think it's something to fall back on. In [inaudible 00:11:09] and everyone culture, they talk about it being the groove. So high performing teams need a home where you feel supported and safe, a groove where these processes you fall back on, and then if you have those two, then you can push people to the edge of their ability. And having a startup and trying all these new... We're doing things we've never done before. We need that to fall back on so we can be at our edge without getting burnt out, and touching against burnout, I guess, instead of going over the edge.

Daniel Stillman:

So Jen, is there more you wanted to "yes, and" on that?

Jennifer Dennard:

Oh, I was just going to say a very simple example of that is, very early on, we set a cadence of meetings of a time for us to kind of connect, a time for the whole team to connect, which at that point was two or three more people, not a huge group, but even just having that simple amount of process or structure of like, "This is when we are going to talk," is really helpful, because then it didn't feel like... It wasn't as hard to raise a conversation or to figure out when we were going to speak about something that we were disagreeing on and you get to resolve. I think those two... "Process" can sound really heavyweight, but for us it started as just like, "When are we going to meet?"

Daniel Stillman:

Yeah, just [inaudible 00:12:26].

Dan Pupius:

[inaudible 00:12:26]. And then names are important as well, so what we're going to meet about. So when Jen and I have our one-on-one, we have a tactical one on one, and then we have a strategic one-on-one and many times we'll talk about tactical things at the so-called strategy meeting, but it keeps us on track, more often than not, to just like, "What are we talking about here?" And then our team meetings, we have an operations meeting with our VP [inaudible 00:12:51], so we're only talking about operations. We're not talking about product strategy or things like that. And then we have an alignment meeting with the leads of all the teams. So the names of these meetings actually set the context and help us keep it on topic and it does deviate, but it is easier to bring back to the core topic.

Daniel Stillman:

Yeah, those names are invitations, right? They set the tone for the-

Dan Pupius:

And the purpose.

Daniel Stillman:

Yeah, the tone and the purpose for those conversations. So you're meeting, the two of you, twice a week?

Jennifer Dennard:

Mm-hmm.

Dan Pupius:

Most times, yeah. We sometimes take a [inaudible 00:13:27], like we'll... If we're exhausted on Friday or one of us is out, we'll, of course, skip, but I think we have, yeah, these two one-on-one touch points.

Daniel Stillman:

Yeah. One thing I'm kind of curious about is I was looking over your website before I came on the call with you all and one-on-ones are one of these things that people sometimes step into these conversations with no plan or with the inkling of a plan, but I think a lot of one-on-ones, there's a clear power differential, right? It's a manager having a one-on-one with somebody who they manage, and you two are co-founders. So I'm curious, in your one-on-ones, how do you... What's that like, right? It's a one-on-one of equals,

Dan Pupius:

I think, before I even talk about our one-on-ones, I think, in general, it's the person with the implicit authority or explicit authority, in some cases... It's incumbent on them to make the space safe, and I will always start the... When I have one-on-ones with people who report to me, it's like, "This is your time. This is where I support you. I am here in service of you, so this is your meeting. It's not my meeting. I get my needs satisfied elsewhere, ideally in a team environment." So that's never going to negate all of the power dynamic, but it does help set the context for that conversation. And I think that's pretty important because if managers use those one-on-ones in a way to have the person report to them, like, "I report to this person," that sets up the tone of the conversation and the purpose of the meeting, whereas if it's actually oriented much more, "This is where I support you," that's how you help people achieve... That's where they're honest with you and when they're open and vulnerable and where you're most likely to learn more things, so I think that's some framing, but I don't know about our one-on-one, Jen, how you feel about that.

Jennifer Dennard:

I think one of the things that we do is we typically have pretty clear areas of ownership, so I don't know. Just like a, I guess, regular one-on-one, we usually have an agenda. We have the topics we want to talk through. It's usually like either of us sharing updates on whichever area we're owning for the time being, and sometimes that ownership gets passed and handed off, sometimes week by week, depending on what's happening, but that is something that I have found upon reflection but upon talking to other founders about sometimes the harder areas when they work with one another. That's been really powerful for us because it lets us have, I think, one, some mind space, because each of us aren't owning everything and, two, the autonomy to go figure things out and then come back together. So I find that often the best analogy, I would say, is someone that you've worked closely with, who you're doing a one-on-one collab with, where you're just working through a problem. I feel like that's often how our one-on-ones feel to me and we just have more problems to work through than the average one-on-one collab.

Dan Pupius:

Yeah, it sometimes feels like a relay race to me, where we're handing off the baton, and sometimes we're like... I guess the analogy doesn't fit perfectly because we have a quick discussion of whether we should hand off the baton, but we do have explicit owners and I do think one of the cool things about the way Jen and I work is we pass ownership back and forth more dynamically than I've seen other people and other people I've worked with.

Daniel Stillman:

Yeah, because that's one of the things that I was wondering, is the... I've heard this before, that some clarity around roles and division of labor is really helpful. Otherwise, there can be unclarity, for lack of a better word, but it seems like the other side to the coin is also true, which is flexibility to pass things back and forth and to shift and alter who's doing what is also really powerful. I'm curious how you navigate that conversation.

Dan Pupius:

Well, I think, we have a Venn diagram, so there's the stuff that's clearly mine and clearly Jen's, and then the middle bit is the messy bit. And luckily, there's not too much there, though that's probably the most critical part of the business for the last 18 months or so, so lots of back and forth on marketing and sales, for example, but it means that we still have these areas, where's it's just very clearly our areas of expertise, where we get to have mastery and complete autonomy. And then it's really the messy middle where we go back and forth. I think if it was all messy, that would be really difficult, or if only one of us had areas of specialization, that would be really difficult as well and probably really disempowering.

Jennifer Dennard:

Yeah. A lot of the decision of who takes something usually relates to bandwidth, and that's both time available but also energy. Sometimes Dan or I will take something just because other person's like, "Oh, I cannot keep doing that," or I don't quite have capacity. And I think that's maybe another thing that we haven't talked about yet in this conversation, is we have invested in through process and tried to cultivate a sense of, I think, safety and belonging on our calls, on how we work together. And that allows me, for instance, to say something like, "I just had hip surgery two weeks ago," and to be like, "Hey, my pain level before or after that is really high. I'm just not able to be what you might consider a normal capacity for me." And Dan [inaudible 00:19:21] hear that and, at least my experience of it, to not feel blamed at all, just to be like, "This is a fact about the bandwidth that we have as a collective system." And I think that allows that kind of handing off of responsibilities in a way that doesn't feel contentious.

Daniel Stillman:

Dan, what more would you say about that?

Dan Pupius:

Yeah, I think Jen has to have a lot of bravery to bring those things up, so I think a lot of the credit goes to her in having boundaries and sharing what she needs in this situation. I do think our history really helps and we've been working together for so long now, and then some of the structure as well, but I think it also takes bravery.

Daniel Stillman:

Yeah. What's some of the structure that you feel makes that possible? You mentioned the architecture is one of the components that guides human behavior. What kind of intentional architecture do you feel like makes that safety possible?

Dan Pupius:

Yeah, so I think one of the key things is... One of the foundational things, and again, this relates to what we're doing as a company, is visibility. Daniel Coyle talks about this in terms of belonging cues, and belonging cues being these micro-interactions that remind you that you're on the same team, but I also think that if there's a lack of visibility into what you're working on and what you're doing, trust just naturally degrades over time. So making sure that we are in sync and seeing what each other are doing and just having a general pulse is super valuable as setting the foundation. And then as a company, we've just been really careful about building these moments for connection, which might, to some people, seem like a waste of time, but I think is really valuable as a way of building that trust and vulnerability, which is the only way that you can have those conversations. So giving gratitude is hard. I find it difficult, but creating structure where people are nudged to give gratitude is really powerful or receive gratitude to reflect and celebrate all these little things of what build up and create the foundation.

Daniel Stillman:

Yeah, I noticed that you mentioned a tactical and a strategic meeting, but I didn't hear a catch up or a vibes meeting.

Dan Pupius:

A vibes meeting.

Jennifer Dennard:

That's how we start all... So all of our meetings internally start with a check-in round, which is where you kind of... How you're doing, green, yellow, red, and I feel like Dan and I... Our meetings in particular often start with, "How are you really?"

Daniel Stillman:

Yeah, just go straight to the second question. "How are you really?"

Jennifer Dennard:

Yeah. I think we try to both be vulnerable with our team to the extent that we can, but there's also a level of we are the leaders and sharing how difficult things might be at a certain time is not so good for the company. And so I think that it is helpful to be able to share authentically in those meetings, even if sometimes I feel like I have to hold some of that back for the whole company.

Dan Pupius:

Yeah. Yeah. And I think even though we have the tactical and the strategy meetings, I think sometimes we're okay putting the agenda aside and just losing the time, and then we'll just... If we need it, we'll schedule a followup, but I don't know about you, Jen, but I find that also the last two years have just been so crazy that it's sometimes just nice to escape into abstract problems relating to the business instead of having to worry about the world that's collapsing around us, so there is some escapism there.

Jennifer Dennard:

Oh, totally. I think we both have that in our personalities, which is probably why [inaudible 00:23:15] helpful.

Daniel Stillman:

I don't think you two are unique in your desire for escapism, but I'll just say, and this is a really interesting thing to highlight, is there are some people who say like, "Oh, let's have a meeting that's just about human connection." And then there's baking it into all meetings.

Jennifer Dennard:

I don't know. You could kind of put that as a motto of Range, that we think that putting human connection directly next to the work is what makes it effective. And there's research to support that related to off sites that are just about happy hours and things aren't as effective as ones that incorporate aspects of work, but we found that, certainly, culture only meetings... We have game times or [inaudible 00:24:03] audio only. We certainly incorporate that as an aspect of our work, but it really does, I think, a disservice to people to have that always be a separate thing, because it makes it... To the extent that architecture and these structures influence us as humans, it makes it feel like there's work and then there's being a human. That's just not what's true. We are all humans at work, and I think that's something that we incorporate a lot into the software of our meeting tool, of our check-ins, all the different aspects, but also into how we operate as a founding team.

Dan Pupius:

I'm sure most people can resonate with this. You have a happy hour where everyone's chummy and being really friendly with each other, and then the following day, people are being passive aggressive over work email or tickets. And it's like you segment the two personalities. There's like, "We're all a team playing ping pong, and then we're arguing with each other over the work stuff." So bringing that sense of belonging into the work stream is... It's just really valuable at actually building the team aspect.

Daniel Stillman:

Yeah, very much so. One thing I think you mentioned, Dan, was this idea that in a one-on-one where there's a management relationship, it's about inverting and saying, "This is your meeting and I'm here to serve you," and underlining it was this idea of, "I'm getting my needs met elsewhere in self care." And I'm curious, you two can't manage each other without you two learning how to manage yourselves. And I'm curious what you do, Dan, and Jen, I'll ask you next, what'd you do to take care of yourself? Before we started recording, we were talking about how we get more protein into our diets, of course, but really, I'm wondering about how you fill your own cup so that you can come to the meetings with Jen in a place that's helpful.

Dan Pupius:

Well, I think the reality is that most times I probably come to the meeting with my cup three quarters full. And if we didn't have that sense of... If we didn't have that history and the foundation, it would easily overflow, especially in today's world, but because of all the stuff we do, it doesn't overflow. And in terms of self care, I have two small kids, live in the city. I don't have that much time. I just have hot baths and go for a run as my self care. And it is minimally viable, but I do think a lot of the work we've done over the last five years and then some of the coaching we've done outside has been really valuable at helping me have more capacity and helping me rejuvenate more quickly. But, yeah, if I'm sleep deprived, I will be a bit sharp and I will step over the boundary of what is safe conflict, right? And that could be a catastrophic event if we didn't have that foundation. So I think that's kind of what's interesting, is that if you have productive conflict or if you encourage productive conflict, there will be times when you step over the boundary and it's what you do then that is the important thing in how you recover.

Daniel Stillman:

Jen, what do you do when Dan gets a little sharp?

Jennifer Dennard:

Usually, I pause. Like Dan kind of knows as well, I'll be like... I look away and I'll be like, "Okay, let me..." And then I usually try to pull out what it is underneath, like what is he trying to say or what's the best interpretation? I think something Dan maybe came up with at Medium or we started using there was the reasonable person principle and the idea that whatever the person's sharing, there's a reasonable explanation. And so I think I probably... Took me some time, probably... So Dan at Medium was more my mentor, I would say, and so to come into a co-founding, peer relationship, as a woman who's also younger, I think it took me probably the first few years to really step more into like, "We are peers." And I distinctly remember Dan going out on a very abbreviated paternity leave, unfortunately, at the start of the pandemic. And I was like, "Oh, Dan doesn't know what he is doing either. He just comes up with an answer when I ask, and I can do that."

Jennifer Dennard:

And I think feeling like a peer in those conversations, to the point we were talking about earlier with power dynamics and stuff, really changes how sharpness lands. It doesn't feel personal. It feels like Dan didn't get enough sleep last night. I think, if it ever starts to feel personal, I also feel comfortable being like, "I'm going to step away from this call. I don't think we're being productive." And we've done that here and there and instead come back together. And I think knowing that, just like any relationship that when you have conflict, even if it does go into a space you're not comfortable, that you have the ability to repair, in my mind, matters because you're never... Whether it's your founding partner or a friend or a spouse, you're never going to not have conflict, unfortunately. And so [inaudible 00:29:24] that you can, typically make it productive, and then when it's not, that you can repair and talk through whatever underlying issue, that feels important to me. And I think we have that really shared understanding,

Daniel Stillman:

Jen, this is such a powerful point. And I think this is something I learned from the world of couples therapy. The ability to actually pause a difficult conversation can seem like a threat if it's not done correctly, to say, "Hey, look, I'm not comfortable with where this is right now," or, "I don't feel well resourced," or, "Maybe we should just pause this and come back to this." What verbiage do you use in those moments to slow it down, to cool down the conversation and to separate and come back? I know you said it only happens occasionally, so you may have to stretch your memory to go back.

Jennifer Dennard:

I'm trying to give a best case. If we're candid, right, sometimes I'm like, "I'm getting upset." And so I'm like, "I need to take a break." And it's not like fairly said in a nice, calm way that we want to when we're in therapy, where it's like, "Oh, say, I think I should take a moment." Probably doesn't happen exactly that way, but just usually something like, "I don't think this is constructive," like we're kind of talking back and forth or, "Let's take a break. Let's revisit this later," because if we've gotten to that point, we've probably also gone over on time, so there's a clear, like, "Hey, we're not being constructive here."

Daniel Stillman:

Yeah. I call this noticing and naming. You're like, "I am noticing my own situation, naming it, and taking it." And I'm talking over Dan, which is...

Dan Pupius:

No, that's okay. No, I think having a language for it is really important and, yeah, some of the models that we've learned about around psychology. I think it depersonalizes it a little bit. So this is from Kegan, but we might say, like, "We're not in level four anymore," or, "We've got hooked," like we've got hooked by the conversation and it kind of just pulls you out of being hooked. It's almost like if you're angry, just saying, "I feel angry," is enough to calm the amygdala. So there's these really interesting language hacks that can reset things and then stepping away. And I do think the repairing and recovering is really important. You can't just push it under the rug. And then if other people were in the meeting as well, making sure that they see the recovery, which is the same as with parents. You can't have parents argue and then make up in private. They have to make up in front of the kids. Otherwise, they don't learn about conflict resolution, so it's a similar principle.

Daniel Stillman:

You mentioned, "We're not in level four anymore." I'm not sure if I know the framework that you're referring to.

Dan Pupius:

So Robert Kegan's book, Evolving Self, provides this model for adult cognitive development and it's essentially... You have the egocentric self, you have the socialized self, the institutional self, and it's ways that your mind makes meaning given the situation. And we are constantly fluctuating between those levels as adults. And it's [inaudible 00:32:39] useful because if someone attacks you on the street, you want to drop down into a level one egocentric self to save yourself, but in the work context, it's not very... We have similar reactions and our brain drops into a different mode of operation and meaning making, and it's just not helpful because we're not being attacked or anything. It's our brain being tricked. So it just gives us some language. And the egocentric self is very black and white. It's very like, "Me, them." The socialized self is all about the relationship and the connections, and then the institutional stuff is a higher level systems thinking space. And even if the model isn't correct and potentially reductive, models might be wrong, but they're still useful.

Daniel Stillman:

Yes.

Jennifer Dennard:

And I think something we do well at this point in our co-founder relationship is identifying when the other person is dropping down. For example, I think, the counter today in maybe Dan being sharp is I will start to speak... If I'm the one who's less resourced and not doing well, I'll start to speak in shorter sentences. I will just seem more flustered. I will actually sometimes turn slightly red. And I think both of us sometimes will say to each other, like, "What are you worried about?" And/or say like, "Well, here's what this is triggering for me," or, "This is what this is making me think about," and the thread I'm pulling on. And so sometimes that really helps us get out of the conversation where we're talking about a very specific thing. And it's really like, "Oh, this other problem that's triggering for us." And less in the therapeutic sense of triggering childhood trauma and more like triggering like, "Oh, I'm actually really worried about this other thing on the sales team or the marketing team, and that's pulling on this concern, even though it seems to be a [inaudible 00:34:35] question."

Daniel Stillman:

Yeah. Although I get the sense that, just from my own experience and relationships, it's hard to say to someone, "It sounds like you're kind of in level one right now, so let's start this again when you're ready and in level four."

Dan Pupius:

It's definitely an ouch. It can be a bit of an ouch, but it can also be a bit of a shock to system because, again, the label and... I don't know. Yeah, there's definitely like, "Oh, man," like a little bit of embarrassment, but then you know that we're in a safe space. There's a lot of regard and you can come back and there's no judgment, and then we get back into the space. And I think having the ability to actually jump up and down through these mental spaces is actually really valuable, instead of getting stuck in them.

Daniel Stillman:

Yeah. Well, so shockingly, our time is running nigh. I'm wondering what I haven't asked you about managing your relationship, designing your conversation, that I ought to have asked you. And Jen, I'll start with you, to see if anything comes to mind.

Jennifer Dennard:

I think there's often a power dynamic in founder relationships. I think just having been a part of a number of COO and collect-all groups, there's often a power tension with the CEO. There's certainly power dynamics associated with gender and with age, particularly in the tech industry. And so I think it's something that I often encourage people to think about and focus on early on. When we first were designing Range and we started talking about equity division amongst the founders, we were pretty particular in terms of what we decided would impact equity. And I would say I got a much more equitable portion than I would with most male CCO co-founders, and I think that speaks to Dan's values but also helped really set the framework and groundwork for me to feel like a peer.

Jennifer Dennard:

And Dan has put in work for that to feel that way. And I think sometimes there's stuff early on, that the co-founder relationship gets off on the wrong foot, even if it's people who work together for a long time, because that perception and that difficult conflict early on of, "Are we equals in this? How are we approaching this?" doesn't quite happen. And then so that encouraging of conflict in that discussion, I think, is really important in thinking about the different power dynamics that can emerge, even if you consider yourself to be peers. And I'm very grateful that Dan is our CEO. He deals with stuff that I don't, and I appreciate that a lot.

Daniel Stillman:

How about you, Dan? What haven't I asked you that I should ask you?

Dan Pupius:

I don't know. I think you kind of hinted this earlier, but we went a different direction, which is that looking after yourself and attending to yourself is so key, because if you're not in a good state, you can't be a good teammate and you definitely can't be a good leader. And I think many leaders aren't vulnerable about that and they don't focus on their strengths and weaknesses and addressing them and thinking about them, and what are their personality dynamics that may be suboptimal or rub people the wrong way? I'm very aware of how sharp I can be and how scary I can be, and I've worked for 20 years to try and correct that, so I think the personal leadership is so important as a foundation.

Jennifer Dennard:

[inaudible 00:38:20]-

Daniel Stillman:

Again, you mentioned you... Oh, sorry. Go ahead, Jen.

Jennifer Dennard:

Oh, I was going to say, and being aware of one's own mental health. Certainly, in the last five years we've had ups and downs and at a pandemic and all the things that have happened. I think being able to own that versus put it on the other person or the company is really important.

Daniel Stillman:

Yeah. Dan, you mentioned coaching has been part of that for you. Is there anything else, besides running and hot baths, that is part of you sustaining yourself and coming with your cup three quarters full?

Dan Pupius:

Yeah, me and my wife... We talk about this a lot and getting out, and especially when we had a young child, it was really hard to get out of the house, but we'd force ourselves to go out into the wilderness and go hiking, and that can be really valuable. So coaching. We do couples therapy as well, which is really, really helpful, just as a way of building our relationship, making us stronger parents and showing up better for each other. I don't know. Probably too much alcohol, not sleeping enough... All these things are problems. I'm probably not super healthy right now, to be honest, but at least we're surviving.

Daniel Stillman:

At least you're getting enough protein.

Dan Pupius:

Yeah. Well, as of last week.

Daniel Stillman:

As of last week. Well, next week's going to be better. Jen, what do you do to fill your cup?

Jennifer Dennard:

Similar tactics of coaching and therapy, I think. Normally, I run. As I mentioned, I got hip surgery, so I've been... I really like reading. It's my form of escapism, to really go deep into a moderately well written to badly written or poorly written fantasy or sci-fi novel, just to be very separate in a different world. My sister's a fantasy author, so it definitely runs in the family, but... And then, yeah, being out in nature. Right now, I can't go very far, so just sitting in our backyard. We have a garden and taking that space. I think a recent thing I've been trying more is expressive writing, where you just write for 15 minutes, and it doesn't have to be... Not really a journal, per se, of what happened, but more just like, "Here's how I'm feeling." That, I've historically found useful, particularly in moments where I'm keyed up or need to process and don't want to necessarily just ignore how I'm feeling, but want to just help the emotion kind of work through.

Daniel Stillman:

Yes. I went to a workshop years ago with Julia Cameron. It was a writing workshop. I went with my mom. It was super fun. And basically, whenever anybody stood up and said, "I'm having some trouble with this, this, and this," she would say, "Are you doing your morning pages?" That was her... Just the three pages of just long hand, first thing in the morning. And whenever I get below zero, I bring morning pages back in.

Dan Pupius:

I think maybe the lesson there is it's less about the tactics, but the important thing is the ritual, so having these rituals. So rituals for connecting with your partner, connecting with your kid, getting physical health, getting good food, whatever it is, disconnecting, escaping, making sure you have those rituals laid down so that when things get hard, you have something to fall back on.

Daniel Stillman:

Yeah. Well, this has been really lovely. I want to thank you both for your time. If people want to learn about all things Dan and Jen, are there other places they should go, besides Range.co, that you'd like them to go to?

Dan Pupius:

I don't-

Jennifer Dennard:

That's the main thing. Check out our... We have a series of podcasts and interviews with other teams and how they manage some of this, called How Teams Work or Lead Time Chats. Both of those are really great resources, I think. We care a lot about educating the community. It's not just like there's some scholarly paper that has the best practice. It's also like, how do people actually do this? So we try to share a lot of that information on our blog, which we also share out on LinkedIn and things like that. Feel free to connect directly on LinkedIn too.

Daniel Stillman:

Well, sweet. I think I'll call "scene" and just make sure that you two... Well, let's do a checkout and make sure that everything felt awesome.

Building an Integrity Culture: Co-Founder Conversations

In this conversation, I sit down with Huddle Co-Founders Stephanie Golik and Michael Saloio.

Huddle is a platform for designers and builders to invest in startups with their time. 

Stephanie has spent her career building alongside founders at studios and leading design and product at fast-growing tech companies. She was an early design leader at Cruise, building user experiences for self-driving cars. Before that, Steph was Head of Product at Mapfit (acq. by Foursquare). She's a proud Cuban-American born, raised and currently residing in Miami.

Michael is a product and team-focused entrepreneur and investor. He’s spent his career working with technology executives and investors. As an investment analyst at Oppenheimer & Co., he followed some of the biggest names in technology including Cisco, EMC, and Apple. Prior to Oppenheimer, Mike covered special situations at Sidoti & Co.

Over the past five years, Michael reimagined his career to focus on early-stage businesses. He was the first employee at SuperPhone, a messaging application backed by Ben Horowitz, Betaworks, Bessemer, and more. Since 2014 he has consulted with, invested in, or advised more than 35 startups that have raised more than $200M in venture financing.

I met Michael years ago and have tracked his rise…when I saw that his latest venture raised 3.3M and was a co-founded company, I reconnected to include him in my co-founder conversations series.

My question throughout this series has been simple - what does it take to build and sustain a powerful co-founder relationship? 

Michael and Stephanie shared some of the insights and principles that helped them do exactly that.

The biggest aha was the umbrella concept of an Integrity Culture, and how many powerful values fall into place with a focus on Integrity.

As Michael points out, it’s not just “I do what I say I will” it's also about a culture of Coaching and Feedback to help everyone right-size their commitments and to give themselves (and others) feedback along the way when they find themselves falling short.

Stephanie and Michael share a conversation format that they use over the course of each week to keep their team on track and in integrity!

Integrity Culture also implicates one of my favorite words: Interoception, a concept I learned from Food Coach Alissa Rumsey.

Michael and Stephanie’s vision of an integrity culture is one where you commit to a thing because you are intrinsically motivated to do it, not through force or pressure…you self-select the thing you are going to do. And that means you know what you want! Interoception is the ability to feel and know your inner state. 

Some additional keys to a powerful co-founder relationship that line up with the other conversations in this series are the ability to have Healthy Conflict (rather than an unhealthy “peace”) and the regular asking and giving of generous and generative deep feedback.

One other insight that was fresh for me in this conversation was Michael’s idea of a good co-founder relationship as one that is “Energy Producing” vs. energy sucking. A powerful co-founder relationship is like a flywheel - the more energy you invest into it, the more energy it throws off.

Be sure to check out my other co-founder conversations, like this episode with Jane Portman and Benedikt Deicke, co-founders of Userlist, on how they connected through shared communities and learned how each other really worked through real-world, previous projects.

You may also enjoy my interview with Carolyn Gregoire and Scott Barry Kaufman, the co-authors of the 2015 bestseller, Wired to Create, where we unpack how they managed their working relationship.

And if you really want to dive deep into the idea of being a conscious co-founder, make sure to check out my conversation with my friend Doug Erwin, the Senior Vice President of Entrepreneurial Development at EDAWN, the Economic Development Authority of Western Nevada.

Links, Quotes, Notes, and Resources

Huddle website

Minute 16

Michael Saloio:

A lot of my challenges in the early days were, I had to define my own schedule. Sounds like really basic stuff, but going from an investment bank where there's pretty clear structure and a way of doing things, highly professional, and then having to wake up every day and figure it out, was that I had to really plan my week, like really relentlessly. And it came down to just doing what I said I was going to do. I have a much broader definition of what integrity is now. I became really obsessed with the... I still am very obsessed with the idea of integrity, but I wanted to build a culture where instead of it being based on hours and management, it was based on setting really clear values and goals and letting people self... I don't want to say self-identify, but letting them say what's possible for them.

And then kind of challenging whether or not that was possible. And then holding them accountable to doing what they said they were going to do. But more than that, calling themselves out when they weren't going to do it. That seemed like a much better model to me than being scared or making them wrong for not doing something, you know?

Minute 17

Michael Saloio:

The way that we do things is on Monday, we have a meeting. It's a standup where we all say what we're going to do for the week. And then on Thursday we have a check-in where we're really honest about whether or not it's going to get done. And we give ourselves the opportunity to ask for help. And that's it, you know? And so instead of feeling like you have to hide or you have to be wrong for not having done something, it's like, "Hey, look, I said, I was going to do this thing and it's just not going to happen this week because these three things happened." So at least it opens up a conversation to, "Well, what do we have to do to actually get it done?"

Stephanie Golik:

What I really loved about it, within our culture that I've started to see is like, it really is... culture is, you get what you recognize or what you praise, I think is the phrase. And it feels like we just really praise when people step up and say like, "Yeah, I said I was going to do that. And I didn't, and I'm not sure if it's still important." Just that level of honesty. Besides that, it's just like, I think a real bonding and humanizing thing to do for a team. It also just gets us back to performing. We move past the... there's a lot of effort in hiding and feeling crappy about not doing something, right? That's just effort that doesn't... we're just kind of trying to say, like, "It doesn't need to be there. We're all humans and we're all trying to do our best and build this thing together."

Minute 22

Stephanie Golik:

And in that moment of deciding to continue to work together and move to this other venture together and take this risk, I felt like I could give him some feedback and we went for a walk in Soho and I gave him really direct feedback and we had a really great conversation that also was a prompt for Mike to also get into coaching and a couple other things, which was like... being really good at taking feedback is an incredible quality. And I think having that kind of experience early on in a working relationship where it goes okay.

You get feedback. It not just goes okay, but it actually really furthers your ability to work together. I think it set the stage for lots of versions of that conversation that have happened over the years, both ways. But you know, there's lots of working relationships where it's just not as easy to have an honest conversation about something that's, again, not working for you or making you feel a certain way and you end up holding it in, and/or doing other things to skirt around it that just don't get to the core problem because you don't have that level of kind of open dialogue. It feels like we established that open dialogue pretty early on, like long before becoming co-founders. So by the time that we got into this more deeper relationship and engagement, we had a lot of that foundation, which I think has been really helpful.

Minute 42

Michael Saloio:

I wrote a blog post on this, it's called You Don't Need a Co-founder, which is so funny because we're sitting here saying that co-founders are amazing. But what I meant by that, I meant a couple things by that. One is, what you really need is people around you. The relationships can take a lot of different shapes or forms. I had some kind of shotgun co-founder wedding type vibes as well. I would just say go slow. It takes a lot of time to understand whether or not you're going to be able to build a company for... Just think about how much time you spend working.

You're going to go into something with someone that might take seven years or 10 years or longer, if you keep going with it. Right? So it takes a long time to understand whether or not you're going to have healthy conflict resolution or whether your skill sets are matched. Right? Another thing we haven't talked about is like, Stephanie is a designer and builder, I'm an ex finance guy who's kind of good at sales and business development and vision. And we're both actually really, really visionary people. But we have the ability to actually make things together. There's a skill match as well. And also our company works with founders, right? So we see a ton of partnerships. So, I guess two things. If you're going to go into work together on something, you got to make sure that you have complimentary skill sets, which is very basic. But two is like, go slow. Get to know somebody. Go into battle with people that you know how to work with.

More about Stephanie and Michael

About Stephanie:

Stephanie Golik is a founder at Huddle, where designers and builders invest in startups with their time. She's spent her career building alongside founders at studios and leading design and product at fast-growing tech companies. She was an early design leader at Cruise, building user experiences for self-driving cars. Before that, Steph was Head of Product at Mapfit (acq. by Foursquare). She's a proud Cuban-American born, raised and currently residing in Miami.

About Michael:

Michael Saloio is a product and team focused entrepreneur and investor. He’s spent his career working with technology executives and investors. As an investment analyst at Oppenheimer & Co., he followed some of the biggest names in technology including Cisco, EMC, and Apple. Prior to Oppenheimer, Mike covered special situations at Sidoti & Co.

Over the past five years, Michael reimagined his career to focus on early-stage businesses. He was the first employee at SuperPhone, a messaging application backed by Ben Horowitz, Betaworks, Bessemer, and more. Since 2014 he has consulted with, invested in, or advised more than 35 startups that have raised more than $200M in venture financing. Mike is now a founder at Huddle, a platform that lets early-stage startups connect with and hire top fractional talent for cash and sweat equity.

Full Transcript

Daniel Stillman:

We're live. Welcome to the Conversation Factory. Michael, Stephanie, thanks for making the time for this conversation and finding a room where Stephanie, maybe somebody won't bump through, which is all good.

Michael Saloio:

Yeah. Thanks for having us.

Stephanie Golik:

Nice to be here.

Daniel Stillman:

Thank you. So, all right. We need to give some context to the people. Can you explain a little bit just about your company and what it's all about? And then maybe we can talk about the origin story of the two of you behind that.

Michael Saloio:

Sure. Steph, you want to tell Daniel here what Huddle is?

Stephanie Golik:

Sure.

Michael Saloio:

What's a huddle?

Stephanie Golik:

What's a huddle? Well, Huddle is a builder community. We are a community made up of over 250 now independent builders from around the world. And the Huddle platform connects all of those independent builders with startups who need help in the early stages of company building. So, we form teams for them of these builders, make up of product development and marketing talent. Anything to add, Michael?

Michael Saloio:

We are a seed stage company based in Miami, Florida, where we both are currently. Stephanie recruited me down here during the heat of the pandemic to start our company together. And we've been building Huddle officially since October 2020. That's when we launched. I guess we started in the summer of 2020. And Stephanie and I have been working together in different ways since 2015.

Daniel Stillman:

Whoa. How did you two meet all the way back in 2015? What's the meet cute?

Michael Saloio:

The meet cute?

Daniel Stillman:

Yeah. Yeah. That's the phrase, Stephanie, I think you maybe know it. I mean, it's like in a rom com, it's like how the two people stumble upon each other. It's the-

Stephanie Golik:

The moment.

Daniel Stillman:

The moment. The moment of serendipity that brought the two of you in this big, crazy topsy turvy world. How did you two actually meet?

Stephanie Golik:

When our storylines converge?

Daniel Stillman:

Yeah. When did your storylines converge?

Stephanie Golik:

It is a good story. So, I was just starting out in my career in 2015. I had previously been in architecture. I had just moved to New York. I was starting to get into product design, user experience design, working on side projects. And Mike actually hired me at my first full-time job. He was helping to run a product studio at the time. Mike interviewed me and it was like the best interview I've had to date. We just like, had a great convo over some hot mint tea and just immediately had a great rapport. And the two of us just ended up really enjoying working together and ended up leaving that studio, jumping to another studio together. And just over the years, have continually found ways to kind of come back and work together on things.

Daniel Stillman:

Hmm. Michael, do you remember that? You had a laugh.

Michael Saloio:

Yeah.

Daniel Stillman:

You were like, "Mint tea. I remember the mint tea."

Michael Saloio:

Well, I'm laughing because the best interview I've ever... It probably was my best interview too, all things considered, now that we're here building this company together. But the reason I laughed was because I had no idea how to interview a UX designer at all. And I think I just really liked Stephanie and I liked that she was building and designing things just in her spare time and was sort of a self made, self-taught product designer. And we were like a really scrappy bunch at this studio. So, she kind of fit right in. But yeah, it was a really casual conversation at the Crosby Hotel in Soho, which was around the corner from the office we worked at 73 Spring Street.

Daniel Stillman:

Wow.

Stephanie Golik:

Shout out.

Michael Saloio:

Shout out to 73 Spring Street.

Daniel Stillman:

So you were like the spark of... I mean, for the lack of a better word, attraction of the scrappiness, that you admired this quality in her. And the other thing I'm hearing is that the conversation was just really casual, but also engaging and fluid.

Michael Saloio:

It was casual. Well, you said it really well. It was casual, engaging, and fluid. It was also very centered on making things and building things. So, that's actually a cool part of the story too, is upon first meeting, we dove right into our passion for startups and building things.

Stephanie Golik:

Yeah. And I also remembered, besides it just being easy to talk and start riffing and collaborating and all that stuff was that Mike sort of jumped past the job we were even talking about and was asking me bigger questions about the next 10 years and got us into much more interesting conversations than many interviews I've been on. So, that was impressive to me as well.

Daniel Stillman:

That's really interesting. What was the question that zoomed out and started to create that bigger image? That's so interesting.

Stephanie Golik:

I think it was something along the lines of like, "For a second, let's just like, screw this job that we're talking about. Really. Let's keep it real. We're having this conversation about like building stuff, like what do you want to build? What do you want to do?"

Daniel Stillman:

Yeah.

Stephanie Golik:

And so to have that kind of branch in the conversation in our first chat, I think was pretty telling.

Daniel Stillman:

That is interesting.

Michael Saloio:

Wow.

Daniel Stillman:

Yeah. Do you remember this, Michael? And I'm curious if you remember-

Michael Saloio:

I did do that.

Daniel Stillman:

...Stephanie's answer.

Michael Saloio:

I don't remember asking that. Let me rephrase that. I do remember asking that, but I didn't remember until now, like re-remember that I actually asked that question. Do I remember what her answer was? I don't think I do. Do you remember what your answer was?

Stephanie Golik:

I think it was that I want to start my own company. Not a huge surprise.

Daniel Stillman:

She said, "I want to make Huddle, this sort of like, you know, agency that's..." No, sorry. That's a bad joke. You predicted Huddle in 2015. Obviously.

Michael Saloio:

We kind of did. We actually talked about that today in one of our internal meetings, that although we started Huddle really officially in the summer of 2020, we've kind of been working on this since 2015 in some way, shape, or form.

Daniel Stillman:

Say more about that.

Michael Saloio:

I do remember that you said you wanted to start your own company, for sure. I also remember in a later conversation that you wanted to be an empathetic leader. Do you remember that conversation?

Stephanie Golik:

Yeah, I do. I do. I don't remember what the context was, but I remember we had a good chat about what I wanted to be. And somewhere it landed with, like, "I really, really look up to strong leaders that have a really warm, empathetic quality." And that's what I would strive to be.

Daniel Stillman:

That's a really nice tension, like strong and warm at the same time. That's beautiful. It's really interesting, Michael. Because I know that, I guess we were just talking recently. I can't remember now if it was 2018 or 2019, where you were thinking about this, a community based approach, like where did the community element come into the conversation for the two of you?

Michael Saloio:

I can tell you where it came in for me in 2018, 2019. Without going too deep down the rabbit hole, I had worked at a prior startup called Super Phone, which was about owning your audience as an artist or creator. And the founder of that company, Ryan Leslie and I, had many a late night chat on just the power of relationships in general. And we talked about the concept of a thousand true fans and how changing the 20 to 30 people in your text feed every day is life changing. Like if you scroll through your text feed, that's your life. Your life is the communication and conversations and relationships that you build with people. And that led me to start a dinner series about wanting to connect people who might not ordinarily meet. Primarily because Ryan was an artist and had all of these people that I had not really bumped elbows with working in finance in New York, for the first part of my career.

Michael Saloio:

And later on, as it relates to Huddle, I was building what looked like a more traditional product and startup studio and basically realized that the most important thing I could do is put the best people in the room. That was it. I kind of had the epiphany as a first time entrepreneur that I wouldn't be better at company building than anybody else. And it was really the entrepreneur and the people that the entrepreneur surrounded themselves with, that was the most important part. I didn't think that I was going to develop a better sprint process or stage gate process or I didn't have any of that stuff. I just knew that I liked founders and I liked creativity and I liked startups. And people just started organically coming to me and Stephanie, because Stephanie and I were always helping our friends launch companies on the side by helping them with their pitch deck and building their app.

Michael Saloio:

Or building whatever they were building. And people just started organically coming to us and saying like, "Who's the best designer you know? Who's the best developer you know?" And I had organically built this list of people because of the dinner series. And so fast forward to 2020, all that stuff. Talked a little bit more about the community and how we launched. But for me it was like, the epiphany that I kind of needed to get out of the way more than I need to get in the way. So instead of like, coaching and strategizing with the founder, it was better for me to just create a container or a space where I could put people who were really good at what they did in the room. And the magic would happen from there.

Daniel Stillman:

Yes. Yeah. What does that spark for you, Stephanie?

Stephanie Golik:

Yeah. That's super interesting. Yeah. I feel like the way that I kind of arrived at some of these things is like, more through the lens of some of the things I learned in architecture and kind of that just made me think of it, Mike, with creating the container. It's like creating a space for facilitation of a thing to happen is just very interesting and exciting to me. I love designing and building things that become interfaces or tools for people to connect and do things together. And that's really what community building is. It's like, just creating that space and that interface for people to meet and do things, in its simplest form.

Michael Saloio:

And I think we both just wanted to make it easier for people to make things together. Stephanie and I worked inside of a lot of different startup studios and accelerators. And it also always seemed like they did a really good job with mentorship and advisory, but they were always looking for a designer and always looking for an engineer. And so fast forward to the pandemic, everybody's working from home. A lot of our friends and collaborators are starting new things, maybe because they were worried about their income or maybe just because they had more time in their day to work on things that they wanted to work on now because they didn't have to go into an office.

Michael Saloio:

And so at the same time, you had all these people who also had spare time to start freelance, like a lot of the way that people start as entrepreneurs, including us, is just by becoming a freelancer. Becoming a freelancer is a great way to become an entrepreneur because you do things on your own for the first time. You start an LLC. You have to figure out your accounting. You have to meet collaborators. And so the two worlds were just kind of colliding. It felt very much like at the same time, that we were like, "Oh wow, there's going to be a lot more people starting things. And they all need to connect with design and development talent. So maybe instead of a studio, we should be a platform that facilitates that."

Daniel Stillman:

Yeah. And that goes to your point, Stephanie, of like, being the architect of a system of conversation, a space where people can gather. In the last conversation Michael and I had, one of the things that really impressed me was the culture of the company you two are trying to build. I'm wondering if you can say something about what an integrity-based culture means to you? How do you feel like you're doing that on purpose intentionally with the space that you're building for yourselves? Not to put you completely on the spot-

Michael Saloio:

Do you want me to take that first? I hired a leadership coach in 2016 for the first time after a conversation with Stephanie actually, which is a different story. And-

Daniel Stillman:

Did Stephanie give you some feedback?

Michael Saloio:

And one of the things that I realized about myself in trying to become an entrepreneur that I needed to improve upon was just having a plan and sticking to it. A lot of my challenges in the early days were, I had to define my own schedule. Sounds like really basic stuff, but going from an investment bank where there's pretty clear structure and a way of doing things, highly professional, and then having to wake up every day and figure it out, was that I had to really plan my week, like really relentlessly. And it came down to just doing what I said I was going to do. I have a much broader definition of what integrity is now. I became really obsessed with the... I still am very obsessed with the idea of integrity, but I wanted to build a culture where instead of it being based on hours and management, it was based on setting really clear values and goals and letting people self... I don't want to say self-identify, but letting them say what's possible for them.

Michael Saloio:

And then kind of challenging whether or not that was possible. And then holding them accountable to doing what they said they were going to do. But more than that, calling themselves out when they weren't going to do it. That seemed like a much better model to me than being scared or making them wrong for not doing something, you know?

Daniel Stillman:

Yeah.

Michael Saloio:

The way that we do things is on Monday, we have a meeting. It's a standup where we all say what we're going to do for the week. And then on Thursday we have a check-in where we're really honest about whether or not it's going to get done. And we give ourselves the opportunity to ask for help. And that's it, you know? And so instead of feeling like you have to hide or you have to be wrong for not having done something, it's like, "Hey, look, I said, I was going to do this thing and it's just not going to happen this week because these three things happened." So at least it opens up a conversation to, "Well, what do we have to do to actually get it done?"

Daniel Stillman:

Yeah. I'm watching you nod Stephanie. Say more.

Stephanie Golik:

Yeah. What I really loved about it, within our culture that I've started to see is like, it really is... culture is, you get what you recognize or what you praise, I think is the phrase. And it feels like we just really praise when people step up and say like, "Yeah, I said I was going to do that. And I didn't, and I'm not sure if it's still important." Just that level of honesty. Besides that, it's just like, I think a real bonding and humanizing thing to do for a team. It also just gets us back to performing. We move past the... there's a lot of effort in hiding and feeling crappy about not doing something, right? That's just effort that doesn't... we're just kind of trying to say, like, "It doesn't need to be there. We're all humans and we're all trying to do our best and build this thing together."

Michael Saloio:

Yeah. I love how you said it's a bonding experience too. It's a really bonding experience to just be honest about what's happening.

Daniel Stillman:

Mm.

Michael Saloio:

I also love what you said about the, it's like a tire with a slow leak. It's literally not working. I really think about integrity as something working, like a system working. It can be your human working, like being in alignment with which is actually authentic to you or what is actually authentic to you. But at the company level, it's the same thing. Where are the leaks? You know? And if you're always just focusing your attention on plugging the leaks, then the wheel's not turning, it's literally not working.

Daniel Stillman:

Yeah. It's interesting, like that Thursday meeting could feel like being ashamed. So I'm curious how-

Michael Saloio:

It could be.

Daniel Stillman:

Yeah. So like, how do you facilitate that to make sure that as you're saying, Stephanie, people feel... This maybe goes to Michael, your point of like, an energy producing partnership. There's that feeling of like, "Oh, I'm blocked," or, "I don't know if it's important anymore," or, "I need some help." What makes that conversation, that Thursday conversation, possible?

Michael Saloio:

Nothing is wrong. Something's not working.

Daniel Stillman:

Hmm.

Michael Saloio:

Hey, something's not working here. Okay, great. What's not working? Let's problem solve around what's not working and get it working.

Daniel Stillman:

Yeah.

Michael Saloio:

It's the elimination of something being right or wrong. To me, at least.

Daniel Stillman:

Yeah. Stephanie, do you want to say more about your nods?

Stephanie Golik:

I'm actually just agreeing. I was thinking if I had anything to add. I think that really is the core thing, is that it really is that removal of right and wrong in it. And we're all sort of working towards the same thing together, so it's acknowledgement of something that might not be working. I was also thinking of some of the... We actually frame our check-ins through a series of questions that we all sort of answer. And so I was thinking about some of those questions that we ask and whether they kind of also open up more of an opportunity for that.

Stephanie Golik:

We ask at the end of the week, things like, "What did you learn?" And sometimes that becomes an opening for people to also kind of open up about like, "Well, I learned that this wasn't working," or that this thing has changed. It's also that lens of like, we're constantly trying things. We're committing to trying things. And then figuring out what's working and kind of just being as transparent as possible about what we're learning along the way.

Daniel Stillman:

Yeah. Yeah. That's something I'm always curious about because in any good story, there's peaks and valleys, like as you say, like sometimes you hit a wall and something doesn't work. I'm curious how the two of you manage your relationship as co-founders, if you've dealt with friction between the two of you.

Stephanie Golik:

Yeah. I mean, well, I'll tell the story that Mike alluded to. Because I think it's [inaudible 00:21:25] story.

Michael Saloio:

It is.

Stephanie Golik:

So, this is before Mike and I were our co-founders. This is back when we were actually working at the first studio, our first working experience together. And we were considering hopping over to this other studio to continue working together. And I think this all comes back to the rawness, realness of that first conversation. Mike and I, I've already, at that point, I think gotten to the point where we were really honest with each other and I think that's really Mike's doing. Mike is very, very raw, very honest. Very direct. I'm less so, but I think he's taught me a little bit of that. And I felt like I could give him critical feedback.

Stephanie Golik:

And in that moment of deciding to continue to work together and move to this other venture together and take this risk, I felt like I could give him some feedback and we went for a walk in Soho and I gave him really direct feedback and we had a really great conversation that also was a prompt for Mike to also get into coaching and a couple other things, which was like... being really good at taking feedback is an incredible quality. And I think having that kind of experience early on in a working relationship where it goes okay.

Stephanie Golik:

You get feedback. It not just goes okay, but it actually really furthers your ability to work together. I think it set the stage for lots of versions of that conversation that have happened over the years, both ways. But you know, there's lots of working relationships where it's just not as easy to have an honest conversation about something that's, again, not working for you or making you feel a certain way and you end up holding it in, and/or doing other things to skirt around it that just don't get to the core problem because you don't have that level of kind of open dialogue. It feels like we established that open dialogue pretty early on, like long before becoming co-founders. So by the time that we got into this more deeper relationship and engagement, we had a lot of that foundation, which I think has been really helpful.

Daniel Stillman:

Yeah.

Michael Saloio:

Yeah. And yeah, I remember the feedback and it prompted me to enroll in leadership coaching. I wanted to improve. The feedback was very directly... It was basically, "Hey, I like these three things, but here's the one thing that I'm not okay with, and this is what I'm going to need to leave and go with you to this other shop." And I was just like, "Cool. I really appreciated it." And then I went and worked on it. I'm skating around it a little bit maybe, but it was around... I think a prior version of me, and still a little bit today, because it's hard to work past these things. I basically struggled to make choices. And so I wouldn't say my thing confidently or I wouldn't make a decision confidently and then something wouldn't be getting done and I would get angry and resentful that it wasn't getting done.

Michael Saloio:

And I realized that I was really struggling to make powerful choices and have confidence to just make decisions. And I was like, "Man, I really want to be able to make really powerful choices and stick to them even if they're wrong." Because I knew if I wasn't making that choice or if... let's say I wanted someone in the office to do something by a certain time and I wasn't asking for that and then I'd be resentful that it wasn't getting done. And so there wasn't just clear expectation setting. And I totally agree with everything that Steph said, or maybe not agree, but it certainly resonates that by the time we became co-founders, we had a way to have healthy conflict, basically.

Daniel Stillman:

Yeah.

Michael Saloio:

So yeah, there still is friction. I tell Steph this all the time, when we do have friction, I leave the room feeling better than having gone in it, which does lead to this concept of like, energy producing partnerships. You can have a partnership that has friction in it where the friction produces results and performance.

Daniel Stillman:

Yes.

Michael Saloio:

Or you can have a partnership where the friction produces something that I would call energy draining, where you leave the room a little bit confused or not feeling so good. And those are just more challenging. It's like a car that kind of constantly breaks down that you have to take to the shop. You want to be able to leave the shop cruising really fast, windows open, in Miami, wind blowing through your hair. You don't want to be taking the car to the shop all the time. And you know, then you get on the freeway and a tire blows out or something. I don't even have a car yet. I'm recently in the process of moving from New York to Miami, so my car analogies aren't that good. Yeah. You don't want to be in breakdown in the breakdown lane couple times a week. It's just too draining.

Daniel Stillman:

You know, I want to unpack a few layers because Stephanie, the feedback you gave to Michael, there's an implication here. One of my theses about conversations and relationships is, there's a conversation that we're all having with ourselves. And for you to be able to give him that very, very clear feedback of like, and to design the conversation, to say, "These are these things I like. This is what I don't like. And this is a blocker for me." To be able to express yourself clearly in that way does is non trivial, right? And that is the work. So we say it's energy producing, but you did put that energy in so that he could hear you.

Daniel Stillman:

Then he has to put the work in to say, "I'm willing to do something about that." And then what we have here is, there is an energy producing partnership because it becomes a flywheel, as you said, Michael. We're all putting energy in, but the energy creates forward motion, forward momentum. It creates feedback loops, right? It creates results. But not for nothing, doing that work on your own to say, "Here's what I want and what I need," and doing that work on your own, Michael like, "Okay, well I'm going to do something about this feedback." Those are conversations that you each had with yourselves that the other person can't help you with, necessarily. That's time you put in.

Stephanie Golik:

Yeah. I love that. It really is true. It is putting the energy on both sides that can produce that results. Because if it's missing on either end, there's effort that's needed. And I do think, to Mike's point around like, you keep having to take your car back to the shop or you keep going the shop. It can get draining. That's why it gets drained. Right? Because there is effort. And if it keeps happening or if it doesn't feel like you're coming out of it with a well working, like a significantly better working relationship, it is a draining thing. But yeah, it's work. It's work on yourself to receive feedback. It's work on yourself to learn how to give good feedback or to have those, be able to articulate those kinds of things.

Stephanie Golik:

I don't even remember how I originally articulated the feedback, but it was because we were thinking about this larger decision about changing jobs. It was something I was thinking about quite a bit. And felt this little nagging thing and felt like I was willing to put in the energy to figure it out. It felt there was something at the sort of heart level. That you want to make it work. And you're willing to put in that little bit effort to kind of dig in and figure out like, what is that feeling? How could I express it in a way that it might be constructive? And then, Mike of course did a lot of the effort on his end to take it and listen fully in the conversation, which is also hard.

Daniel Stillman:

But you also did that step of listening to yourself first.

Stephanie Golik:

Yeah, absolutely.

Daniel Stillman:

Which is nontrivial work of like, you know-

Stephanie Golik:

An interesting way to put it.

Daniel Stillman:

What am I feeling? You sensed something and you're like, "Wait, this is bothering me. What is it that's bothering me? Can I express it clearly?" I think it's sort of an ongoing joke that we want someone who can read our minds. And it's just obviously not a thing. That work of listening to ourselves and then the work to be able to express ourselves in a way that someone else can hear. And as you said, Michael, any hard conversation, we always feel better afterwards if we put the work in. And I think people, this happens all the time. We're like, "Oh my God, there's this hard conversation. I don't know what to do." It's like, well, if you face it and you sense into yourself and you do the work before the conversation, it's always going to be better after that conversation.

Michael Saloio:

Yeah. And if you express yourself authentically inside of the conversation. I like what you said about the flywheel and about putting energy in that actually creates more momentum on the other side of it. That's a really cool way to look at it.

Daniel Stillman:

Thank you. Yeah. I've been thinking about the... somebody talked about it in a recent interview.I did. I'm not remembering who now. They talked about Jim Collins' flywheel effect in Good to Great. And every company needs to have a flywheel, but I think people need to have flywheels. And clearly partnerships have to have flywheels too.

Stephanie Golik:

Yeah. It reminds me too of something that Mike and I talk a lot about, which is just the understated importance of like, just commitment, which is like, in some places, a dirty word. But truly just committing to the thing together. I think it does. It allows you to kind of push through some of those more energy draining moments or put in the extra energy to figure it out. It's sort of like marriage.

Daniel Stillman:

Yes, totally. Michael, what's coming up for you?

Michael Saloio:

Yeah. Oh, so what's coming up. So, what actually came up for me is, I was listening to different podcast earlier this year called Invest Like the Best, Patrick O'Shaughnessy. And he has an investor's field guide and the founder's field guide. And he has an episode with Mike Maples from Floodgate, who has just epic quotes on startup building. And one of the things he says is, "The future isn't something that happens to us like the weather. The future is what we decide to create." And I just couldn't agree more with that. And that really is a big way that I look at commitment too. There's so much emphasis in the startup ecosystem about testing and ideating and seeing what works and what doesn't work, which is clearly very important.

Michael Saloio:

And also you have to choose to do the thing and really choose it. I think there's too much emphasis on ideating. The way that I look at entrepreneurship is like, I just know what I want to make. And I'm pretty ruthless about making it. In my head, it's already done. Because why not take that lens? Does that mean it's necessarily going to work? No. I don't know it's going to work. Maybe that's where the testing and ideating comes in. But in my head, Huddle is built. It's already done, you know? And like, I don't think that's arrogant. I think it's, I have to choose that lens. I have to choose to be that confident about it. Because I don't know if it's going to work, anyway. Right? Like when you commit to something, you don't know that it's going to work, but you have to commit to it, because then once you commit, we have no idea what's on the other side of our choices and our commitments. We think we do.

Daniel Stillman:

Well, I mean, it obviously works on the team to team, like, project to project basis. Right? It's the question of like, what does it look like at scale? Which is always an interesting question.

Michael Saloio:

Yeah. But my choice to get up every day and just choose that this is what I'm doing, and I see what it looks like in the future and I'm going to take steps today to build it. And I'm really committed to it. The question as to like, what should I do or how should I do it, it kind of melts away. It's just consistent action towards the goal. I hope that lands.

Daniel Stillman:

Yeah, it does. Well, I mean, it also sounds like that's something that you've worked on you. From what Stephanie, you were saying earlier. I think, Michael, you've struggled with what I think a lot of us struggle with, which is optionality. Right? Making a decision and choosing to build one thing and not another is always hard.

Michael Saloio:

Yeah. I've spent a lot of time not committing to things staying on the outside of things.

Daniel Stillman:

Did I read that right?

Michael Saloio:

Yeah. Completely. I spent a lot of time trying to find the "right thing."

Daniel Stillman:

Yeah.

Michael Saloio:

Which is a cop out for taking responsibility for the thing that you really want to do.

Daniel Stillman:

Yeah.

Michael Saloio:

At least for me-

Daniel Stillman:

And that goes back to integrity, basically like, what do I really-

Michael Saloio:

Yeah. Yeah, exactly. I should have said that like from I. I shouldn't have said you.

Daniel Stillman:

But no, it's all good.

Michael Saloio:

I ultimately have to do the thing that I really want to do.

Daniel Stillman:

Yeah. Well, and that's the point of the thing. So, we're coming close to the end of our time together. There was one other topic I did want to make sure that we hit upon, which is failures. Because we're talking about what I like to call a bucket of puppies. Everyone loves a bucket of puppies. If you've ever seen a bucket of puppies, it's adorable. And you two have a positive flywheel and an energy producing partnership and open communication. And I suppose we could just like, everyone could just take this podcast and just listen to it backwards slash inverted and say like, "These are the lessons. If you notice these things, leave the partnership right away, or don't start a company with them." But you know, Michael, you did talk about lessons from failures and you know, when it comes to being a conscious co-founder and intentional, co-founder, I'm wondering if the two of you have any anti patterns from your own experience. Things I did in the past that didn't work include blank.

Michael Saloio:

Oh yeah, I do. So, I-

Daniel Stillman:

Wait, hold a second before that. Because Stephanie, I want to check in with Stephanie first because I think she had something.

Stephanie Golik:

Honestly, the only thing that comes to mind, I mean, there are definitely many, but the one that comes to mind for me, that's definitely very partnership oriented is really that this is a true for me statement that may not be true for everyone. But that going it alone doesn't work for me. Going out and trying... I'm a very... I don't know. I am a builder. I feel like I can go off and kind of build what I want to build or do this idea that I want to do. And in the past, that's led me to just kind of take on a project or an idea solo and try to just be the person that makes it happen on my own.

Stephanie Golik:

There's been a number of little heartbreaks along the way with that, with things that didn't fully, really, really get off the ground, really get a chance. And I think that having a real co-founder partnership has been a real learning for me in why the co-founder route is the route most taken. Because really, that level of partnership, and that level of commitment on both ends, I think it's really, really important to actually getting hard stuff done.

Daniel Stillman:

That's really good advice. I think going it alone is tempting.

Stephanie Golik:

It is tempting for some more than others. For me, it was very tempting and I did it multiple times. And here I am. I probably wouldn't do it again, honestly.

Daniel Stillman:

Yeah. Thank you. Michael, what was on your mind?

Michael Saloio:

Did you say anti patterns?

Daniel Stillman:

Yeah. When we talk about lessons from failures or partnership, Stephanie's giving us a like, "Don't even try to not do a partnership," which is an anti, anti, anti pattern, I think.

Michael Saloio:

Got it. Well, my anti patterns. I think I relate to them more as failures, but positive failures.

Daniel Stillman:

Positive failures.

Michael Saloio:

I had many a partner. They were all super high performing, quality human beings. And many of those partnerships had either mediocre results or were just failures. They didn't work out. And everyone went off to do amazing things afterwards. But what I learned from me is that I would often enter the relationship being really inauthentic about what I wanted. I joined two different businesses as like a minority partner. And what I really wanted was to be the CEO or be the co-founder. And I wasn't super real about that at the time.

Michael Saloio:

I had to go through those things to learn that about me as well. But those are my learning lessons, is that enter the partnership and be like really raw about what you really want out of it. And that's something I think Stephanie and I did really, really well too. Because I was going to go it alone for a hot minute. Because I was like, "Yo, I don't know if I can do this again. I just keep trying out these things and they're just not working out." And so yeah, I was tempted to go it alone too. But we have the ability, based probably stemming from that initial conversation and many conversations like it, where we can just be really super truthful about what what we wanted.

Daniel Stillman:

Yes.

Michael Saloio:

Yeah. Honestly creates a lot of trust. Right? It's pretty simple. It's harder to do in practice, but.

Daniel Stillman:

Yeah.

Michael Saloio:

Yeah. I wouldn't say the fatal flaws of any of these failures was any one particular thing other than just an inauthenticity about... I'll just speak for myself, what I wanted out of that relationship. But I think if you talk to some of my ex partners, they'd say similar things.

Daniel Stillman:

Yeah.

Michael Saloio:

Yeah.

Daniel Stillman:

That's really beautiful. And I forget what it comes down to-

Michael Saloio:

Or who knows what they'd say?

Daniel Stillman:

Well, I mean, it comes down to... in a way, Michael, what you and Stephanie are saying is very similar. It's like, if you want to be in a partnership, you have to know why. You have to know what you want and what you want from the other person. And to be really clear and direct about that, which is pretty much what we've been saying this whole time. We should call scene very soon. What haven't I asked you about partnerships that I should be asking you? What haven't I asked that I ought to have asked?

Michael Saloio:

I don't know if this is something you should ask, and I hate to give advice, but I think generally speaking, and I wrote a blog post on this, it's called You Don't Need a Co-founder, which is so funny because we're sitting here saying that co-founders are amazing. But what I meant by that, I meant a couple things by that. One is, what you really need is people around you. The relationships can take a lot of different shapes or forms. I had some kind of shotgun co-founder wedding type vibes as well. I would just say go slow. It takes a lot of time to understand whether or not you're going to be able to build a company for... Just think about how much time you spend working.

Michael Saloio:

You're going to go into something with someone that might take seven years or 10 years or longer, if you keep going with it. Right? So it takes a long time to understand whether or not you're going to have healthy conflict resolution or whether your skill sets are matched. Right? Another thing we haven't talked about is like, Stephanie is a designer and builder, I'm an ex finance guy who's kind of good at sales and business development and vision. And we're both actually really, really visionary people. But we have the ability to actually make things together. There's a skill match as well. And also our company works with founders, right? So we see a ton of partnerships. So, I guess two things. If you're going to go into work together on something, you got to make sure that you have complimentary skill sets, which is very basic. But two is like, go slow. Get to know somebody. Go into battle with people that you know how to work with.

Daniel Stillman:

Yeah. Totally. Any closing thoughts from you, Stephanie?

Stephanie Golik:

Yeah. I think I agree with all of that. Yeah. My recommendation or thought would be that like, if you can, work with, partner with someone that you've known and you have some of that kind of just normal relationship stuff in place with. Because it's still two human beings that are in a relationship, it just happens to be around co-founding a business together. But there's a lot that's just relationships stuff. So having that, I think you have a little bit of a head start. But at the very least, starting out with those open, as open, raw, and authentic of conversations as possible about things that are sticky and uncomfortable, like commitment. Even if it is that today, the commitment isn't fully this or that, I think is really, really important. A lot of people skirt around that stuff and then someone's committing more and it just starts to become more complicated than it's worth. So, I think the authenticity just happening as early on as possible is really important.

Daniel Stillman:

I love it. Well, you two. Thank you so much for being in a huddle with me today. If people want to know more about Huddle or the two of you, where in the internets should they go to learn more about the things that you all are...

Stephanie Golik:

You should head to huddle.works.

Daniel Stillman:

Especially if you are a early stage founder who needs something really, really powerful built. If I understand correctly.

Stephanie Golik:

Absolutely.

Daniel Stillman:

And Michael, you and I have talked about this, you need more people in the Huddle too, right? Lead designers and creative strategy people and those types of folks as well.

Michael Saloio:

Yeah. Ultimately, we're building a really high end, high quality builder community. So, we have a lot of people who are ex high growth tech company, ex founders, ex product leader at a FANG, or-

Daniel Stillman:

A MANG, I think we call it now.

Michael Saloio:

Ex agency executives, and we're making it really easy for them to build independent careers inside of Huddle by connecting them with really amazing startups that just desperately need their help.

Daniel Stillman:

All right, y'all. Well, I will call scene. Thank you so much, you two. You two are awesome.

Michael Saloio:

Yes. Yeah.

Stephanie Golik:

You're awesome.

Michael Saloio:

Thank you for having us. And thank you. I've told you this many times but you are the best asker of questions I've ever met.

Stephanie Golik:

[inaudible 00:47:11].

Michael Saloio:

It was really a pleasure. It was just a really flowing conversation. I'm like, "Whoa, what just happened? How long have we been doing this?" But that was really fun. So, thanks for having us.

Daniel Stillman:

Oh, it's my pleasure. All right. Now I'm really going to stop recording.