Season One

Professor Paul Pangaro on the Cybernetics of Steering Conversations and a Theory of Everything



So...Cybernetics. I was describing the ideas behind this episode to a friend and he was like "cybernetics is about steering?" And yep, it is. Check out the show notes for some essential links on cybernetics, *and* an essential diagram to help follow along with this episode.



The idea is this: You have goals and I have goals. If we're in conversation, the way we find a shared goal is through probing, experimentation, alignment on means, revision of the goals, mistakes...and recursion. The recursive process of seeing a goal, aiming for it, seeing the "error" or gap and then moving to close the gap...that's cybernetics. And the principles of cybernetics really are a way to think about everything. Or, rather...anything that has a purpose, goals, intention. So, orgs that need to shift business models, teams that need to tighten timelines...getting your friends to pick a restaurant for next week...So, everything that really matters!

If need people to agree on things before they can happen, you need cybernetics. And if you're good at getting people to agree, you're a solid cyberneticist. Or, in my language, an ace conversation designer.

In my journey through conversation design during this first year of the podcast, Dr. Paul Pangaro has been a rich guide and mentor, one of the people who sees the diverse ways that conversations shape the world, how systems can have purposes and goals....and in true conversational style, I've certainly been altered by his ideas. When I recorded this interview in 2017, Paul was the chair of the interaction design MFA at Detroit's College of Creative Studies. Currently (in 2019) he’s Professor of the Practice in the Human-Computer Interaction Institute at Carnegie Mellon University.

Paul got his BS from MIT, where he wound up getting hired by Nicholas Negroponte into a program that evolved into the MIT Media Lab. He then went on to get a PhD in Cybernetics in the UK and came into contact with Gordon Pask, a cybernetics and conversation design visionary, whose work Paul is still evolving and processing.

The application of cybernetics to conversation has been a mind blower for me. It's helped me think about how to structure longer projects, to design teams, to form powerful framing questions. That ability to frame a question in an invitational or motivating way, making it seem solvable without giving the's an amazing superpower to be able to kickstart an amazing conversation.

But asking that question designs the conversation,  sets the stage for what comes next...and so I'm always cautious in my conversation designs to control for writing solo before group conversation flows...because whoever speaks first sets the stage for whatever comes next...they speak in response to what's been spoken already.

We talk about three big conversations design concepts that are worth paying attention to: how to think about group composition and cadence, the conversation with yourself, in the past (time travel!) and the relationship between goals and play.

1. The group conversation. Do we have the right people in the room? Do we have enough diversity to answer the question at hand? Can we design a cadence of interaction that allows us to shift the question and the composition of the team in a responsive way? In Cybernetics, a system that wants to influence another system has to be at least as complex.

Is your team more complicated that the problem you're solving? Good!

But...who gets to frame the group and the cadence? How do we invite people into the group conversation? Who has the power to give permission?

2. The conversation between myself now and myself in the past through writing. I'm a fan of pen and ink...because as we write, we watch the ink flow and see our thoughts as they were moments ago as we move into the future. The act of sketching or writing allows us to witness our thoughts as they were and converse with them. Crazy right?

3. How established, shared goals allow us to play together, even become one. If we're dancing, a "form" helps us know our roles and goals. Are we dancing the Tango or a Waltz? Knowing this makes it possible to better respond to stimulus from our partners. I think that's why Agile/Design Thinking/Lean are so popular. With Parkinson's Law of ever expanding work, there seem to be no rules anymore. We've broken partner dancing (starting with the twist) and now we never know what to do on the dance floor. Some of us crave for a throwback time, the swing era, the mystery of the tango...where we knew what to do, where there was more clarity. Agile, Scrum, Design Thinking...they are a dance form that makes it clearer what the roles and goals are. They're a game we can play if we know the rules and have a shared vocabulary.

When we share goals, the line between us blurs, or dissolves. We live in "amity"...or you can draw a box around us and call us a system with a shared purpose: to dance!

So...this is the last episode of season one. It's been a year, 22 episodes, hours and hours of conversations in real time and many times that in listening and editing and writing about them. I've learned a ton and had a blast. I'm taking the holidays off and am working on season two! Stay tuned and enjoy the show.



Show notes and links:

Paul on the web

More on Pask

Martin Buber (I and thou)

Requisite Variety: On Paul's Site and Elsewhere

Alex Bavelas

Ambiguity experiments - people start to break down when there's too much of it, blaming each's exceeding our bandwidth (or requisite variety)

The Self Talk NYTimes article: When people repeated their tasks to themselves, they did it better, if it was a clear task. Also check out the Conversation Within Your Head.

Heinz von Foerster: If you desire to see, learn how to act

The Dhatupata: There's a lot less online about this than I thought there would be! The author is here, but deeper info is not. hmmm...

Jesse Israel gives People Permission to Connect


Have you ever had that feeling right before a party you were throwing starts? That creeping dread that no one will show up? Today I talk to Jesse Israel, who doesn't seem to have that fear. Jesse flips that feeling on its head. For Jesse, it's very simple: People *want* to connect. And the invitations we, as organizers and conveners, send out...they're just permission slips. The invitation gives people permission to connect.

Jesse Israel is the founder of Medi Club and the Big Quiet, which hosts huge public meditations in places like Madison Square Garden and the World Trade Center's Oculus for literally thousands of people. I met Jesse Israel at a dinner party way back in early 2015 at a Rabbi's house. We had a great conversation and discovered a few shared interests. Somehow we discovered we both loved biking the city and he invited me to check out his cycle club, the Cyclones. And then he mentioned that he had a meditation club, too. As a life-long meditator (before it was cool!) I was intrigued. When I went to my first Medi Club, I was struck by the energy and the intimacy of it. How easy it was to connect with the crowd, which got larger and larger each time I came. The Medi Club meets monthly and regularly attracts a few hundred people ready to sit in silence with their peers. The Cyclones is similarly huge, and a blast, every time I make it out.

So, to be clear: In Jesse's view, we connect *through* things: the bike, the meditation, is permission to connect. It's the connection we crave. He just opens the door.

There are few key conversation design principles I want to pull out of this conversation, to look for as you listen, all around how to frame profoundly motivating invitations: What permission will you give for people to connect? What's the deep and clear purpose of it? What are the boundaries of the invitation? And something else I saw that Jesse does: he pre-invites. He builds a coalition of the willing early, before he opens up the larger invitation. 

Deeper into the conversation, we talk about how to sustain yourself as a community builder: Jesse talks about how he's learned to develop compassionate boundaries, to maintain his internal integrity. If you don't say no to some requests, you can't continue to give. We also talk about how to trust and develop your team. When that trust is in place, that's where the growth really happens.

For more in-depth consideration of this conversation, head over to the conversation and take a look at the show notes! I'd also suggest you take a listen to the episode with Daniel Mezick, founder of open space agility, who's thoughts on invitation match up with Jesse's profoundly!

What Permission will you grant?

At Medi Club it's okay to open up. When you step into the door, you know you're among friends. How is that permission granted? Jesse shares first. He leads the way and opens the floor. He makes the example clear: He's going to be real and so you can be, too. Over time, the community attracts more and more of this energy. Others take up the charge and spread the norm.

What's the Clarity of your Purpose?

Early on, Jesse wrote a medium post to declare the intentions of the community he was forming.

The article lays out why Medi Club exists in extremely clear language and outlines the purpose of the club in a way that passes the T-shirt test (a rule of thumb that seems to be from Peter Drucker)

Also: Is there a larger purpose? The Cyclones is a fun Saturday around NYC, but became something more when they started an Indigogo campaign to get bikes in the hands of 1,000 children in Tanzania.


Is there an authentic way to enlarge the purpose of your invitation over time?


Boundaries show up in two ways: Boundaries for the invitation and boundaries for the inviter. The Cyclones invites you to give up expectations and planning...for one afternoon. You don't know where you're going, and that's okay. Medi Club stretches that boundary with their circles: Anyone can host a Medi Club circle and create the same energy with a smaller group, anytime they want. Medi Club holds the larger circle and gives each smaller circle an "authorization" to share the same invitation.

At min 26: Jesse talks about another form of boundary: A boundary for the convener.

"If I don't have compassionate boundaries, I can't show up as a friend or a community builder."

When he's at medi club, he's a public person, and everyone there feels some sort of connection with him. But after the club night is over, Jesse has to find a way to restore his strength and be with himself. And if he said yes to every interview, every request to "pick his brain" from the community...there'd be no time for anything else!  This compassionate boundary is a huge challenge, because saying no doesn't feel generous. Finding a way to create a generous no is a critical skill for leading communities.

I'm terribly grateful that Jesse was willing to sit down with me for this conversation. I learned a ton from it and I hope you do, too.


The Big Quiet

Jesse's Former Record Label

Cyclones Bike Club

Medi Club Medium Article

Cyclones Indigogo


Claire Wasserman knows how to design powerful experiences, communities and organizations


Women make 79 cents on the dollar compared to men and that's wrong. (depending on how you cut the data it's either slightly worse or slightly better - but it's still bad). It's a systemic problem and most of us would throw up our hands and say "There's nothing I can do about it!"

Instead of doing nothing, Claire Wasserman has built a powerful community called Ladies Get Paid around a powerful and critical idea: Fixing the wage gap. And while she says that "this conversation needs an overhaul" it's not just talk. Claire's organization brings women together in town halls all over the country where they focus on what woman can do with their own hands, like learn better negotiation skills and apply for jobs they might not feel ready for, but probably are. Men have been trained, somehow, to be more (slash-over) confident, while the imposter syndrome seems to effect women more strongly.

Claire is an experience designer, designing in-person, transformational events in the same way that a UX designer crafts an app or an HR manager crafts a personnel policy: Thinking about the goal, the intended effect it will have on a person, and working backwards. It is, in the end, Human Centered Design. The materials change, but the goal is the same!

That, after all, is the nature of, and best definition for, Design: Making something to shift the way things are to the way you want them to be. Ladies Get Paid is designed *by* Claire to make the change she wants to see in the world, to change the conversation about gender and money. Beyond her amazing story and her journey to creating this company, I dove into how Claire architects her business, her events and her community.

One issue that Claire and I get into is how to include men in the conversation. What are the levers available to us to design an intimate, safe and productive conversation for women (her primary audience) while allowing men to participate, to help, to learn? How do you design a conversation about gender issues without letting gender become an issue?

Claire has been tinkering with a design that allows men to ONLY ask questions...this format would draw a hard line on mansplaining. Like Jeopardy for conversations, it's a rigid restriction, but would keep men honest: Am I talking to be heard, or to be curious and to learn? It's giving men who want to come to the town halls a hard line: Ask or be silent. Don't declare or explain. When I heard that idea, I offered another option: The fishbowl, where men can *only* listen, from the outside. It's a harder line (but easier to follow for the men!)...and there's a lot of intimacy created for the inner circle of the fishbowl, with no cross-talk possible.

Which is "better"? No men? Men listening in, with no input? Or men inside the circle, but only asking? Each conversation design has implications, repercussions, challenges...there's no best! Claire, like any great designer, will tinker, test and try and see which feels right for her and her community.

Two conversations we didn't talk about enough: How Claire manages her own *internal* conversation. Claire is bootstrapping LGP financially and emotionally! Right now, she doesn't have the mentorship and support she is offering so energetically to others. Taking a step back and getting you core needs cared for is 100% essential for founders!

The other conversation we didn't dig into is negotiation tips and perspectives. For that, you might want to listen to my interview with Harvard Negotiation Professor Bob Bordone, and download my negotiation prep sheet on the downloads page!

You might also check out episode 13 with Rei Wang , Director of the Dorm Room Fund, where we talk about community building and episode 4 with Sara Mitchell of Faraday Futures, where we talk about listening to users: but not all of them!


Enjoy the conversation!


Show notes and links:

Claire on the Web

Ladies Get Paid

Claire's Hyperakt talk

Robert Bordone can Transform Negotiations into Conversations


When I look back at the way, way too many Instagram photos I posted during my week at Harvard's Program on Negotiation, I'm left with a sense of awe and gratitude. If you take a listen to episode two, you can hear me getting a solid tip to take the workshop from Leland Maschmeyer, a very smart dude and chief creative officer at Chobani. When someone like that tells you that this class is the best, most worthwhile he's ever taken, you listen. It was *still* hard to take time and money to go. I'm seeing this now with my upcoming Facilitation Masterclass that I'm co-hosting with Think Clearly's Mathias Jakobsen. Someone just canceled their attendance due to a client workshop coming up! I get it. I told my biggest client that I was taking the workshop at Harvard and to not even *tell* me about anything that might pop up that week. I didn't want to get FOMO.

I couldn't know, wouldn't have guessed that my experience as a design thinker and facilitation coach could have prepared me well for my experience at Harvard, or that there would be so much overlap in the Program on Negotiation's approach and the design thinking approach to empathy, active listening, co-creation and ideation. I didn't even think that negotiators cared about that stuff. Robert Bordone, my professor, turned out to be a kindred spirit. And while some of my negotiation counterparts during the training felt that my drawing, colorful post-its and whiteboard use was weird, Bob got it and loved it. We've been talking for months now about how to combine our offerings into something fun and exciting!

Robert Bordone is the Thaddeus R. Beal Clinical Professor of Law at Harvard Law School and the Founding Director of the Harvard Negotiation & Mediation Clinical Program. He teaches several courses at Harvard Law School including the school’s flagship Negotiation Workshop. Bob also teaches in the Harvard Negotiation Institute and the Harvard Program on Negotiation’s Senior Executive Education seminars.

As a professional facilitator and conflict resolution consultant, Bob works with individual and corporate clients across a spectrum of industries. He specializes in dispute systems design and in assisting individuals and groups seeking to manage conflicts in highly sensitive, emotional, or difficult situations.

Negotiation in our culture is a bad or fraught word: it makes people anxious. We see negotiations as win/lose, contentious. That's a misunderstanding. It doesn't have to be win lose. Bob sees negotiation as a creative act that generates possibilities and that can create new value.

I took away three big Insights from our conversation.

1. Perspective Taking: FROM THE "OTHER SIDE" and The BALCONY

You *must* take the perspective of the "other side". The "untrained" negotiator only asks their counterpart questions about their interests and preferences 7% of the time. Finding more about *why* people want what they want is the key to great negotiations. Before you even get into the room, you need to spend half of your prep time thinking, not about what you want and think you can or should get, but what the other person thinks *they* can and should get and why. That's why I made my 1-pager negotiation prep sheet, which synthesizes and summarizes the key elements I learned. It's divided down the middle to remind me to take that time and think one-to-one on all aspects of a solid negotiation preparation. You can download that in the show notes.

Bob also talks about going "to the balcony" to look at the whole situation from an outside perspective, which can be very powerful.



2. Move from Negotiation to Conversation

When you find the points of difference in criteria, interests and positions, the negotiation doesn't have to devolve into conflict. You differ. Congratulations! You've identified a dilemma, a core issue. You can call that difference out, and ask "How might we close the gap in our positions?". Then, you can negotiate about the negotiation. You can discuss the differing positions, and lay them all out. The fresh air and sunlight will only help make the process more enjoyable and productive. Don't be afraid of the conflict. Name the game, and find a new way to play it.




If you can frame the core conflict with an opening, welcoming question, you and your counterpart can generate multiple potential solutions using many of the tools available in the Design Thinking canon. Negotiating about the process can be a lot easier than deciding the issue. A fair process is easy to choose. A fair outcome is then a lot easier to see, even if we don't get everything we want.

So... Enjoy the episode. Bob is a wonderful thinker! You should check out the show notes and watch some of his other lectures online, especially his talk about increasing conflict capacity!

Below are nearly all of the images I scribed during the week. There's a lot!

Kate Quarfordt On the Seasons of Creative Conversations


Today I talk with Kate Quarfordt,  the Founding Director of Arts Integration & Culture at City School of the Arts. My conversation with Kate was a rich and wonderful surprise! I found her 4-seasons framework someplace in the corners of the internet and was immediately enchanted with it. Spring, Summer, Fall and Winter as metaphors for the flow of work... The Framework is so powerful in the types of conversations it allows into the larger conversation about work, especially winter, a time to reflect and consider, to heal and incubate. It's rare to make space for that type of work! (see a link to the model and our first meeting on twitter here)…her original image is really lovely, a watercolor work of art! I’ve made a “cleaned up” black and white version here.

the four seasons-01.jpg

The opening and closing circles Kate hosts in her school to bookend the touched my heart! It's such a beautiful way to work. And so similar to how Daniel Mezick gets organizations to shift how they work through Open Space Agility! Check that episode out here!

This conversation has started to open up the idea of threads and threading in conversation design for me. I first got the sense of threading from my conversation with Nandini Stocker, Google's Head of Conversation Design Advocacy. As I see it now,  the arc of a conversation  is made of stories. And the way Kate describes our stories coming together to make a new one, using the word "Braiding", makes so much sense.  Conversations are the exchange of stories, and placing ourselves and others into the hero role, shifting perspective as empathy and generosity demands is the flow of real dialogue.

Finally, we talked about how creative work requires an audience! An Audience provides a "pull" and "push" for work. At least, that's the way I experience it. Even when I don't feel like it, I push myself to finish work on an episode because I know people are waiting (pulling) for it. And there's a loop of feedback on the work: People write me to tell me what was great and where I missed the mark. That's one of the reasons that I feel the conversation between an organization and its customers is one of the most critical, missing pieces in companies that struggle with a sluggish work cadence. There's not enough urgency.  If you want to dig into that conversation more, check out the episodes from Rei Wang, Director of the Dorm Room Fund and Sarah Mitchell, Lead designer at Faraday Futures. Both helped me see principles at work in sustaining great conversations with customers and community.

 Thank you so much for listening and I hope you enjoy the episode as much as I did making it !


Notes and Links


Meeting Kate on Twitter

New York City Charter School for the Arts (CSA)

Specials On C


Threading in Conversation Design: In Podcast Show notes

What we need is a Montage (montage!)

The X that we were solving for: Feeling out of synch, loss of clear cadence

The Seasons Wheel applied to a Week or a Cultural Transformation:

Open and Closing Circles: Open Space Agility with Daniel Mezick


Mary Oliver: making yourself visible to yourself in a way you never imagined!

From Blue Pastures:

I don’t mean it’s easy or assured; there are the stubborn stumps of shame, grief that remains unsolvable after all the years, a bag of stones that goes with one wherever one goes and however the hour may call for dancing and for light feet. But there is, also, the summoning world, the admirable energies of the world, better than anger, better than bitterness and, because more interesting, more alleviating. And there is the thing that one does, the needle one piles, the work, and within that work a chance to take thoughts that are hot and formless and to place them slowly and with meticulous effort into some shapely heat-retaining form, even as the gods, or nature, or the soundless wheels of time have made forms all across the soft, curved universe – that is to say, having chosen to claim my life, I have made for myself, out of work and love, a handsome life.



The Inner Winter Process: Leaving yourself voicemails! (creates a third point for reflection, just as a drawing or journal does)

Dave Gray on Drawing creating a clearer interface for conversations

Morning Pages

The Inner Conversation

Spring Cleaning Script from Mama Gena:


Holding Space is incredible power: Who initiates the request? Who Has permission? The Paradox of Flow vs Framework: Absence of Structure vs. Structure vs. balancing who introduces the structure.


What's the Deal with Agile?


How is a school like a conversation? Moving from the School-As-Script model to the School-As-Dialogue model.

Waterfall vs Agile


Kate's Post-call reflections on Winter and Work as a Relay Race:

"As I was transitioning into the rest of my day I realized that there was one last thing that I wanted to share apropos of the winter phase and the importance of rest and rejuvenation--not just in the creative learning space, but also in the context of activism and resistance. As I mentioned, we are doing a lot of work with young folks around using the arts as a vehicle for activism, especially given how passionate they are about making their voices heard in this current political moment. On Monday night I had the chance to perform with the Resistance Revival Chorus, a women/femme-led singing group created by the leaders of the Women's March to keep the momentum of the march moving forward and also--crucially--to frame joy and rejuvenation as acts of resistance in and necessary elements of a sustainable movement. Paola Mendoza, co-artistic director of the March, and one of the producers of Monday night's event, said something that evening that resonated super powerfully with me.


She said, "The resistance is not a sprint, but it's not a marathon either. It's a relay race." I love that image because it evokes the sustainability that becomes possible when hard work and leadership are shouldered by a full community instead of by a single individual. There's a sense of permission implicit in this approach, the understanding that it's ok for each member of the community to pause and refill the tanks every so often, because there's always someone else right there who's ready to take up the baton and run the next leg. In the context of the season wheel, this is the idea that different community members can be in different phases at different times...  it's OK for you to be in winter, because you know I'm in summer and I've got you covered, and then we can switch so I get a chance to rest and reflect while you keep the work moving forward. I'm excited to bring that relay race image back to the kiddos when we gather to kick off year two.

Coaching Conversation with Mark N On inviting people into your conversation mode


My coaching conversation with Mark covers some really deep topics, and I am really grateful to Mark for his presence and willingness to be open, to go deep, and to let me share this recording of our coaching session.

We hit on three key ideas that are worth looking at in your own work!

1. Your Meetings=Your Conversations=Your Organization

The meetings you have, the conversations you can and can't have IS the organization you are in. If you can change the way you meet, the way you converse, you can change how you organize.

As Martin Buber, the 20th Century Jewish Philosopher said: 'All real living is meeting'

If your meetings don't feel like they're alive, it's up to you to bring the energy they need to come back to life. Mark's organization is so focused on delivering on their core promises in a big way that they micromanage and try to eliminate failure. Without any tolerance for failure or conjecture, without an idea of constant experimentation and learning, new ideas can be deeply frightening. Every meeting is about delivery. They are an organization of closers. That brings us to idea number two:

2. Openers, Explorers and Closers need each other

3 Modes of Conversations.png

Mark identified how frustrating it is when teammates have mismatched models of creativity and different abilities and tolerances in and with the other modes. Mark identified the three modes of creative conversations as Opening, Exploring and Closing (which I try to teach to every group I come in to consult's so core to productive collaborative conversations!)

Opening is the creative divergence that loves to bring new ideas to the table. Exploring is the creative emergence,  which allows ideas to breathe and grow. And Closing is the creative convergence, the comfort with eliminating choices, aligning and delivering on ideas.

Mark is an Explorer. He likes to talk things out, to let things emerge from the soup of his creative process. Closers, particularly , find that mode frustrating, wasteful and confusing. Closers like to land the plane, to figure things out, to end dialogue.

Openers, Explorers and Closers need each other. And they each need to learn how to tolerate the other modes and ask for their own needs in creative conversations. Which brings us to our third key idea:

3. Invite people to a Finite Game

We all need to design invitations with the creative tendencies of other people in mind. Mark wants others to understand his creative energies and help him support and shape them. But he needs to frame the process as an invitation into a  finite game. In my work, I find that people are willing to try something if they know that they can end the game anytime they want! Mark also wants others to support *his* mode of thinking, but isn't thinking about how the other people on his team might be thinking the *exact* same thing! So, the rules of his game, the game he wants to invite people into, we could call the "give me your energy, attention,  benefit of the doubt and tolerance for my creative modes" game. That's a big ask, and totally unilateral.  His job is to find a way to include other people in the process, and to make the rules of his game apply to everyone.  That's an invitation that people can get behind. That's the art of conversation design!

As Mark says, he needs to learn how to be with others in a way that isn't" just launching into my mode without preparing people for the rules of the game" and he needs to do it in a way that feels natural, not in a way that requires him to invert his approach, to turn himself upside down and inside out in order to work with others, which is what he's doing now. And it's killing him. Treating every conversation like an experience, he has to *design* the invitation into the experience in a way that resonates with his partners.



The question we start with, can a public purpose organization be more agile, becomes "can a purpose driven person bring the energies needed for creative transformation?" And that question, I believe, requires individuals in the organization to be agile, to be comfortable picking up the creative energies required for the moment, for themselves and for those they work and play with. Organizational agility totally and completely counts on people who can be agile in their movement between the creative modes and who can frame shifts in those modes as invitations.

So...that's a lot to chew on. Thanks again to Mark for letting me record and share this and for giving me the opportunity to listen and speak with him! Enjoy...

Stephen Sokoler on Designing Meditation and Coming to your Center


In episode I talk with Stephen Sokoler, the founder and CEO of Journey Meditation, a company dedicated to a world where more people meditate! I wanted to talk to Stephen because the inner conversation we need to foster is often forgotten completely. Instead, we focus on our teams, our organizations, our communities...all of the other critical conversations we've discussed in past episodes. But without going inward, the whole thing falls apart.

Meditation is like when an actor goes backstage to freshen their makeup, change costumes, look over the script... In life, we go from role to role without pause...and meditation is a way to step back and let it all chill.

I screwed this episode up! I'll be honest. I've done it before. When you're doing your own field recordings, it's easy to press the record button once, watch it blink, check your levels and then get into the interview. Oops! You actually need to press the button twice! The blinking stops and the seconds counter goes up. I messed up and lost about 30 minutes of sweet, sweet conversation with Stephen. Noticing it during our interview sent a cold chill through my whole body. I  just wasted this man's time, terribly. I had two options. Say nothing and try to "fix it in post" or cop to it and try again. I went for honesty...and since we're friends, Stephen humored me and we started over.

I mention this, not because I love honesty or vulnerability (although I do!) but because you might hear how the conversation with Stephen starts off a little stiff, a little mechanical. We are both *pushing* energy into the system to try to get the energy of the conversation back to where it was!  It's not tremendously noticeable...but you'll hear, once we get to the halfway point, things relax, we find a new thread for the conversation instead of trying to pull back towards the old one, and the conversation finds a more natural tone.

Meditation is like this, too. Being present has a gravity, but we can lose it, drift off to wherever. And we have to "bring ourselves back" in a way that isn't forced or artificial.  In the episode, Stephen and I discover another really interesting point, a connection between meditation and conversation that I hadn't noticed before.  Meditation is about coming back to your center. Recently, I was talking to a facilitator friend of mine who described his role as "holding the center" ...facilitating a great team conversation is about holding that space for real dialogue, open, at the center, and keeping people who drift off from getting too far. We just bring things back, as gently as we can, to the thread and keep things going.

Enjoy the episode! Stephen is a gentle and passionate soul, building an amazing company based on something he truly loves...I learned a lot from this episode, and I hope you do too!

Journey Meditation

Buddhism for Busy People

The Four Core Conversations: Medium Article coming soon!

The Costs of Burnout

Light Watkins

Sharon Salzberg

Why have a Coach

The benefits of Group Meditation

Open, Explore and Close: The Three Creative Conversations Medium Article coming soon

No Good or bad ideas: Episode two with Abby Covert

Stephen's Five MCs (in order mentioned, not ranked)

Biggie Smalls





Honorable mention:

Chance the Rapper

Elliot Felix of Brightspot Strategy on changing conversations through changing spaces

On this episode of the conversation factory, I talk with Elliot Felix, founder of Brightspot Strategy, a boutique consultancy. Elliot founded Brightspot almost seven years ago, and as a former founder of an even smaller design consultancy, I'm totally impressed by what he's built and grown. Elliot has a background in Architecture, which I tease him about (only an architect uses "sightline" in a sentence)...different types of designers talk about and see the world differently: we manage different materials. I studied Industrial Design, and so I often look at an idea and think "can this be made at scale?"...even if it's a service, I break it down and ask if it can be manufactured, reproduced. This tendency can annoy people! It's been recently suggested to me that when people tell me about their ideas I should just say "that sounds fun!" and leave it at that...



Elliot was kind enough to do our episode on site at Brightspot's offices in the Financial District here in NYC and as we walked around chatting about various artifacts in the office, Elliot's love of space as a primary material of design was clear. As he says in the opening quote: the right space can facilitate work, help express ideas, support and reinforce or make culture manifest.

I've seen this in my own facilitation work: I can't tell you how many times I've seen a group get stuck in rut, literally because they'd run out of wall space to work with. Just giving them a new wall to work on gave them a new space to have a conversation, got them unstuck. Walls help make work visible, and when work is visible we can have more productive conversations. Without it, we slow down. Designing the space work takes place in *is* conversation design. Change the space, change the conversation.

At Brightspot they frame challenges as a three conversation checklist: Examining the Spaces people are in, the services offered in those spaces, and how people are organized in that space. This checklist is, itself, a design for a productive client-consultant conversation. Trying to shift a system by approaching one of those conversations and not all of them is going to be harder. On the other hand, changing all three at once might be tough. But having the conversation about space, content and people is clearly crucial, that's why Brightspot designs their client conversations to include each of these three aspects of work.

When I teach facilitation I always tell people that they have to make the space they are facilitating in their own...and my favorite story of this is one of my first days working with Applegate Farms,  an organic food company, back in 2013. The room we were working in was large, cavernous, and had three big tables arranged in a "U" shape, with a screen projecting at the mouth of the U...the room had been designed for presentation, for the "sage on the stage"...but I wanted the group I was coaching on design thinking to collaborate, not focus on me! The U made everyone sit on the outside, facing me, not each other.

So during the break, I took the foot of the U and rotated it, so all three tables were parallel. The team walked in and was a little disoriented...the room was the same, but the energy was different. They sat in the chairs, facing each other, and we could get down to work in the style I was trying to cultivate.

Thinking about your own work: Is your space working for you or against you? Do you have the right variety of spaces, large, small, intimate, public, to do your work? In conversation design, we talk about the Q: the requisite variety of talent on your team, the right balance of familiar faces and fresh seems like, in talking to Elliot, that there's a similar quality of balance to be found in the spaces a truly functional company inhabits. If your space isn't working for you, shake it up!

Links and Notes

BrightSpot Strategy

Making a War Room for projects (but can we find a better name?!)

Expertise Audit: What do our people know? What knowledge aren't we tapping?

Vertical years and Horizontal years: Alternate Keeping the work the same and adding people with new skills and Evolving the offering.

Sightline - the most architectural word Elliott uses

Osmotic Communication

Leaders send signals whether they think are sending them or not: Semiotics

Idiosyncrasies of Leaders can be scaled unintentionally: Elliott over-analyzes, so his org tends to as well! Be intentional about communicating what's optional and what example you're setting, what aspects (quirks) of your personality you're transferring to the culture.

Focus and Time: Choosing our battles and having the time to fight them: Is there a better word: Where to learn and how to grow?

2X2: Size and Structure of conversations

Q of teams: New Yorker Article and Source, ie Requisite Variety in a System

Is your space working for you?

Larry Greiner:  The Greiner Curve


Alistair Cockburn on the Heart of Agile, Jazz Dialog and Guest Leadership


My conversation with Alistair Cockburn was Agile to the core! We revised our timeline and deliverable with a quick standup and got right into it: After all, Agile principle #2 is to welcome changing requirements, even late in development. To wit, I thought we had an hour, early on the call he asked for 20, tops! (Somehow I kept him on the line for 45, since I'm deft at conversational manipulation. And he was keen to keep it going, too.)

Alistair quite the nomad, teaching Advanced Agile workshops all over the world. When he's not teaching, he might be dancing Tango in Argentina or brushing up on his French in Nice. But sometimes the location is too distracting, so he was holed up in Florida where he found a town that was *just* boring enough to allow him some time to get some work done. He was moving house unexpectedly the day we were slated to chat. I saw on Facebook that his AirBnB had a shag carpet and the humidity and mustiness mixed with a thick carpet was making him sick! I tried to give him an out, but he was adamant we do our conversation, even for only 20 minutes. His motto: Now is better than the future.

One of the pleasures and inspirations of talking with Alistair is that he's a man who really lives his principles: Agile principle #10 is that "Simplicity--the art of maximizing the amount of work not done--is essential". You'll hear how Alistair tries to design his life to make this principle a reality!

As I mentioned two episodes back with Daniel Mezick, around Open Space Agile Transformations, Agile is kicked around a lot in the consulting world, but my sense is that all of those people haven't actually read the Agile Manifesto! Alistair was one of the originators and signatories back in 2001, and it was a response to a broken way of working. But just like any ideology, it's come to be interpreted in alot of ways by a lot of people. It was fun to go back to the source!

Alistair’s Heart of Agile Framework

Alistair’s Heart of Agile Framework

I really enjoyed Alistair disagreeing with my characterization of Agile as a Design for Conversations. But I see it that way: Agile designs for some conversations and  not for others. And in fact, Alistair has a lot in common with Dave Gray, who I interviewed a few months back: Dave wondered about who has the right to design a conversation and if it can be overdesigned! Alistair is a proponent of Guest Leadership...that making space for momentary, voluntary leadership can powerfully transform work and teams.

An early version of Alistair’s “Agile Software Development: The Cooperative Game”

An early version of Alistair’s “Agile Software Development: The Cooperative Game”

Alistair and I had what he would call a Jazz Dialogue: a conversation with a meta-conversation layered on top! I have listened to this episode a few times and it's a tough one to summarize or encapsulate. One thing that I'm left with is the idea that even the desire for agility or the hunger for no ideology is an ideology. Which leaves me reflecting on the ways that my own internal tendencies leads to my own ways of seeing things as "right". After all, designing a conversation is power and power should be exercised carefully...because I could be wrong!

Show Bullets and Links

Alistair Cockburn on the Web

Agile Manifesto

Crystal Clear

Improvisation in Dance: What's Fixed and What's Flexible?

"I expect people to decline my advice"

The Oath of Non-Allegiance

Precision vs. Looseness

Crystal Clear: The Sloppiest methodology that could possibly work (Martin Fowler)

"Arranging my life for the maximum amount of freedom"

Anchoring Sloppiness in Essential details. (the opposite of an Overdetermined System)

Cultural Invasion: Design as Cultural Imperialism

Assuming that people bring their whole adult self to work:

Agile Practitioners mentioned:

Daniel Mezick

Ken Schwaber

Nic Sementa

Kay Johansen

Guest Leadership

RE: When do people step forward and help: The Good Samaritan Experiment (hint: when they're not in a hurry)

Be the Change you want to See can backfire

Host Leadership

The Art of Hosting

Open Space Technology

Going Meta: Talking about how we talk

Jazz Dialogue

The Heart of Agile

Self Storytelling

Kokoro: The heart

Alistair's Poets: ee cummings and Emily Dickinson and a poem Alistair wrote in honor of ee:

Rei Wang of First Round Capital's Dorm Room Fund on Community *as* Product


One of the great pleasures of hosting this show is that I have an excuse to reach out to old friends and spend some quality time with them. And I get to double the quality time! I really love gettingto listen to the whole episode again. It's a time to dig in and figure out what the episode was really about, and write these essays. Originally I was going to have the episodes transcribed and then read them, but in episode 2, I heard a different perspective. Information Architect  Abby Covert  talked about how processing her own research transcriptswas essential to her work....I tried it, and she was right.

It can be hard to give oneself the time for reflection and learning, even though our internal conversation is  the most critical of all the conversations I've been researching (See David Whyte's The Three marriages for more on that!) In a few weeks I'll be sharing an episode I did on Meditation, one of the key tools to maintain (and silence, occasionally) a healthyinner conversation. Redesigning your inner conversation! Who wouldn't sign up for that from time to time?

In this episode I talk with Rei Wang, Director of the Dorm Room Fund. Rei and I connected way back in my Design Gym days: I think we were running an innovation day for GOOD magazine  where she was manager of GOOD Local. The workshop might have been  around connecting with your neighbors? We stayed connected as she moved to General Assembly (where I taught UX part time) as she rose up the ranks and managed their rapidly growing community efforts.

She now directs the Dorm Room fund for First Round Capital, and it's an amazing and unique organization. First Round does early investing in companies like Blue Apron, Birchbox and Warby Parker. And while the Dorm Room Fund is funded by First Round, it's run completely by college student volunteers, not professional VCs! This tight community of volunteers IS the Dorm Room Fund.

I think there is a lot talk about community: about building it and trying to monetize it...but few people treat their community as an living conversation to be designed.  In the opening quote I pulled, I was struck by Rei's perspective that companies develop better products in deep dialog with their communities. To some, this is obvious, but only those who cultivate their community consistently and with intentionality get to harvest insights and profit!

Community can be just for celebrating and marketing a product, it can be to have customers contribute to the product...but Rei sees her community *as* the product, which means she's very careful to orchestrate it's development and evolution. The volunteer students in the Dorm Room fund must have a high level of autonomy and drive, which means she has to pull the work out of them, not push it on them!

And her community is rapidly refreshing, by design: Each year they lose people as they graduate and gain students who come in: Capability leaks out of her community constantly! Rei's solution doesn't seem to have a name, so I'll call it Cohort Mixing. In her annual event, she makes sure incoming, current and outgoing groups all connect in significant ways, in large and small groups and over time. This helps keep traditions and institutional knowledge alive and constant, even as the community renews.

Thinking about your own company or can community transform how you develop and test ideas? And how can you empower people in the community of your company to share and pull their own work forward, without you pushing every day?

Enjoy the episode! Rei's insights are solid gold. No bonus tracks this time...Rei and I somehow got it all in under the bell!

Show notes:

Community as Product workshop at CMX East 2015

First Round Capital

Dorm Room Fund

Defining Community

GA Hub: Community Engagement through curation

CMX Community Professionals Organization

Good Magazine

Foursquare's Superuser Group

The Famous Designer who said internships should be paid!

Rei's totally venture backable card company based on her mother's tiger mom texts

Radical Candor

Level Mixing In Communities

CMX's excellent article on community Engagement

Mutualism in Pair Relationships

Tony Robbins - I am Not your Guru

Slow Goodbyes : The Post-Wedding brunch

Automation in Group Decision Making: Not what they use at DRF, but an interesting example of using automation to simplify group conversations at the close

Balancing Privacy and Openness in Community: An office perspective

Mashup Teams: The optimal density of connections in teams

Motivation in Volunteer Communities: Open Source Sustainability and community building

Rewarding your community Volunteers: The Creative Mornings Summit



Daniel Mezick on Agile as an Invitation to a Game


On today's episode I talk to Daniel Mezick, author of the Culture Game and the founder of Open Space Agility. He’s is also the co-author of Inviting Leadership.

Daniel has a really unique perspective on culture, self management and how to make agile really work. At the core, agile believes that a team doing work is the authority on what needs to be done for that work, since they're closest to the work. This is self management at the team level.

In trying to make a switch to agile ways of working, organizations often dictate new frameworks, patterns and procedures. To dictate a new way for how work is to be done is basically the opposite of self management...and a clear limit on how an externally generated conversation design can really work: Change from the outside is going to get push back.

That Agile is implemented in a non-agile way is an irony not lost on him!

In Daniel's view, culture is a game, how work is done is a game, meetings are games, with rules, ways progress is measured...some of the rules are implicit, some are explicit, but it's kind of annoying to play a game with no rules, or with rules unevenly applied, or with rules that change without notice. If you're a reader of "Calvin and Hobbes" you've heard of CalvinBall, and you know how frustrating it is!

Whoever *must* play, can't really play... (that's from james carse's excellent book on Finite and Infinite games)

Daniel suggests that agile be *invite only*, pull, not push, and that that "pull" invitation be in the form of an Open Space meeting. People that opt in, step into the circle, decide what to talk about, and leave with proceedings, outputs. That starts a new game, with new rules, written by those who want to play.

His Open Space Agility process is an answer to the question of how to change the rules of a work culture in a clear and fair way, without hemorrhaging people in the process. Open Space dictates that whoever responds to the invitation are the right people, what conclusions they come to are the right conclusions, worthy of an experimental test, at the very least.

Open space meeting philosophy has infected my own conversation design practice. I feel particularly uneasy when a facilitator I'm working with tries to massage or shift the decisions a group is coming's one of the reasons I say a facilitator should ask better questions instead of giving answers. A great question is an invitation. An invitation is the start of a new conversation. This episode has me rethinking all the invitations I send out, for all my meetings, and all my conversations, moment by moment. Are my invitations inviting? Are people hearing an invitation to the game I want them to play?

Check out the a bonus track where Daniel and I talk about Holocracy and his work with Zappos....enjoy the episode!

The Agile Manifesto: 12 values and 4 principles

Jeff Sutherland

Scrum: rules, roles, artifacts

Planning Poker

User Stories

The Alpha Geek and the pecking order

meetings as games

Open Space Agility

Open Space four principles and the law of two feet

Butterfly and the Bumblebee

Waterfall vs Agile Culture

Pull vs Push Culture

Triggering Self management

four variables in software development: cost, delivery date, features, quality

client's changing their mind is a feature, not a bug

Pareto's Principle is the opposite of what you think

90% syndrome

Code gets brittle

The Big Picture Diagram of Open Space Agility

Signal Events in Culture

Buying into a process vs. Authoring a process

Proceedings of an Open Space Meeting

Organizational Cadence

The Agile Imposition

Beware the man of one book

SaFE Framework



The Mandate of Holocracy at Zappos

Holocracy or Quit

Nandini Stocker on Google's Map for how to make conversations work


In this episode of the conversation factory I had the distinct pleasure of talking with Nandini Stocker, the head of conversation design advocacy and partnerships at Google. She's the rare individual who is more of a conversation design geek than me, to the point that she interrupted me just to make a point about how awkward interruptions are!

We cover a sprawling number of topics in conversation design, and you might enjoy downloading Google's PDF on "How Conversations Work" and read along! I think just knowing that threading, repair and turn taking are *things* means you can look for them in your own work and find ways to transform conversation experiences that you design.

David Bohm, the storied physicist, wrote a book called "on dialogue" and said "Conversation is a principled, mutual process of collaboration and negotiation." So I shouldn't be surprised when Google's map of how conversations work matches exactly to the process of opening, exploring and closing I teach groups to follow when designing a creative, collaborative process for design thinking and innovation. Opening a channel for conversation is like the invitation into a cooperative game, a world to explore and engage with, and every leader needs to think empathically to design these invitations to be...inviting! Finding places along a conversation journey where there is breakage leads us to think about how to repair the thread of conversation and keep things moving along towards closure: a desired action or agreement!

We've be conversing for thousands of years, and we've gotten pretty good at it. But being good at something doesn't mean you know how to teach someone else how. Nandini's work is specifically on how to help us talk to digital agents with more natural ease.  We spoke a few weeks ahead of Google's I/O conference, and she's since sent me a wealth of talks that happened there that you might enjoy digging into. One of my favorites is from James Giangola, who *literally* wrote the book on Voice Interfaces. He talks about Conversational Hacks and digs into the cooperative principle, a way of helping us think about how relevant, clear and helpful information is exchanged at a steady pace in a good conversation.

Compare two exchanges:

"How much did your shirt cost?"

"Don't you love it? I got it at Vinnie's Vintage Warehouse!"



"Don't you love it? Shirt has five letters and five is my favorite number!"

To a computer, both responses contain about the same "amount" of information, but only a human conversationalist can tell that the information is irrelevant and least for now!

If you want to hear Nandini tell one of the worst/best Harry Potter puns ever (She calls puns the earworms of the English language, check out this short outtake.


Show Notes and Links:

Grice's Maxims in brief and extended

Threading and building threads

Seven of Nine

Turn Taking and Yielding

Conversation Repair

conversation overlap

Personality in digital agents:

discourse markers

Google: How Conversations Work

Google's quick reference design principles for conversation design

Amplifying Women's Voices in Obama's oval office

Barge In capability

The Uncanny Valley

On Inner Dialogue

Clifford Nass on Multitasking and his Obit


Bonus: Core talks from the Google Team from IO17:

This one is my favorite: Applying Built-in Hacks of Conversation to Your Voice UI 

Building Apps for the Google Assistant 

Finding the Right Voice Interactions for Your App 

Defining Multimodal Interactions: One Size Does Not Fit All

In Conversation, There Are No Errors

Getting Your Assistant App Discovered

How Words Can Make Your Product Stand Out

PullString: Storytelling in the Age of Conversational Interfaces 

Google's VUI design codelab:

Crafting a Character: Design an engaging Assistant app

Some solid talks from IXD17 on chatbots and conversational UIs:

and the pun game

Sally McCutchion on Holacracy and Self Management at all levels of organization


Holacracy asks a big question: How can organizations be designed  in a way that really works, for everyone in the organization? Right now, orgs are often structured according to power from the top to the bottom, rather than self management distributed throughout the organization. This slows orgs down and demotivates some people.

In this episode, I talk to Sally McCutchion, a certified Holacracy coach based in the UK. Sally teaches public workshops on Holocracy and coaches orgs  in making the shift to working with Holacracy.  Sally and I had a seriously wide ranging conversation about Holacracy. We hit on some big topics towards the end that I've placed in the extras, which you can find here. Check those out, as they're really juicy, just scroll all the way down!

One conversation design principle of Holacracy is to allow information and knowledge to flow through the org. Too often, people at the "edges" of an org, the people closest to the users, know a lot about what's wrong and how to make it right...but those same people don't feel empowered or safe to speak up, or even to just do something to shift issues. One CEO who's organization I coached years back desperately wanted people to feel a sense of ownership: How, if you own your house, and the toilet is running, you fix it, if you know how, or talk to someone who can. You don't just let it run. Holacracy attempts to open regular channels of communication between areas of the organization and to allow sections of the organization to feel that they can solve problems that they see without asking permission, waiting for permission, identifying if permission is even possible.

Holacracy designs several meetings within orgs very rigidly, in order to break down power structures and allow all voices to be heard: People are expected to bring updates framed as needs, not just complaints. Other structures  are a lot more open and can be adapted to the unique company requirements. It is without a doubt a very interesting design for organizational conversations. I get into the weeds with Sally a bit, and if you follow the links in the show notes you might find some of the terminology and structures dizzying...but the forest and the trees of Holacracy are worth absorbing: That self managementand purpose are essential all scales: at the scale of the person, the team, and all throughout an organization.

Show Notes:



Apollonian Gasket

Glass Frog


Holacracy Tactical (triage) meeting

Rep Link

Lead Link


"If you want to go fast, go alone, if you want to go far, go together."


Another Interview with Sally: Punks in Suits





Donna Lichaw on Storymapping and Seeing With New Eyes


Today I talk with Donna Lichaw, a UX strategist, coach, teacher and author of The User's Journey: Storymapping Products That People Love.

What's awesome about Donn'a approach to storytelling is that it's practical. There are a lot of frameworks for storytelling: The Hero's journey, Aristotle's 2 or 3-ish act structure, the rising and falling action of "Freytag's pyramid". It really doesn't matter which framework you the end, when you see things as story, story becomes a doorway into a new way of working. Story becomes a material you can shape by design. For me, I've started to see conversation in the same way: a material that can be shaped to create better experiences for people.

Donna and I talk about story*telling* vs story*making* and story*doing*. Storymaking is not the act of enrapturing a group of people around a campfire or at a podium, in a's knowing how you want people to feel about an experience after it's over, what you want them to remember, to walk away with, to talk about. Storymaking isn't about manipulation, it's about intent, in this mindset. When you see experiences as a rising and falling arc, you want to make that arc smooth and incredible. You want to shape it well, with no jerks, gaps or least not unintentionally!

Designing with Story in mind and designing with Conversation in mind seem to me to be two sides of the same coin. You want the person experiencing your story to respond in some way. And the next story you guide them through continues that dialogue until...? I don't know. The next chapter?

Every Story has a hero, and we want to root for that hero, to see her win the day. In a great conversation you try to make the other person the hero, not's the empathy with the other person and their needs and goals that makes story a powerful tool in great conversation design.



Donna's Site

Donna's Book: The User's Journey: Storymapping Products That People Love

3 act structure: What did Aristotle Say about that?

rising and falling action

4 act structure

5 act structure

the hero with a thousand faces: Book

The Hero's Journey

Dave grey mapping workshops with the Hero's journey

Star wars and the Hero'sjourney TED Radio hour NPR episode

dan harmon's story circle

the writer's journey book

The Writer's Journey on the web

Nancy Duarte's Book Resonate

Nancy's Ted Talk

Presentation Zen

Dan Roam Back of napkin

The storytelling of Steve Jobs and the iphone release

User Scenarios

Burying the Lede

How I built this podcast: Lyft and story

Marshal McLuhan: Hot and cool media

General Background on McLuhan: Video


Coaching Conversation with Phil N on Shifting the Entry Point of Challenging Converstions


For this episode, I did a 30 minute coaching call with a friend of a friend that turned into a wonderful and transformational hour! Phil is a talented photographer and entrepreneur, and we spent a good section of our time looking at what conversations in this life are functional and which are missing something. He's part of solid men's group, so we could use design principles from that experience to reframe how his less functional patterns are working.

As he says in the opening, part of the change was using the tools of conversation design to map friction points in his conversations with women over relationships and work to shift that conversational pattern in three ways:

One, to have the conversation he's avoiding sooner. (time)

Two, to generate multiple ways to open up that conversation.  We talk about how to "Open up" a dialogue in the most conscious, empathetic and energizing way (not to force it) and to generate multiple openings for challenging conversations to find a space that feels authentic, empathetic and effective. (ideation)

Three, to find a way to continue to converse with as much comfort and regularity with women as he does with men. (pattern)

In essence, we're talking about Rhythm. Or the technical term is Prosody:

"the systematic study of metrical structure, the rhythmic and intonational aspect of language"

The one physical aspect of your central nervous system you can control is breath...the depth and frequency of your breathing. When you're in stress, regulating your breathing can transform that state. Just like the pace of breathing, pace and depth is an important part of a conversation that you can control: both the frequency of responses IN communication and speed OF communication.

One clear outcome of our conversation was that just like he'll go to his men's group every Monday, whether he feels like it or not, he has to make a *date* with himself to consider if he's being honest with himself and open with others. Can you make a date with yourself to consider whatever topics are critical to your own personal conversation?

At about the halfway point we shift to his ambitions in photography and his resistance to owning his ambition. We talk about incremental conversations versus a paradigm shifting conversation: Playing chess vs Sweeping the pieces of the board and creating your own type of greatness. Making the conversation on your own terms, rather than playing by the rules. (see episode 006 with Sara Holoubek where we talk about accepting/rejecting trends and I talk about non-complimentarity)

Enjoy the session! And it you'd like to have a conversation with me, just reach out on the coaching page. Show links are below.

Dave Bohm on Dialogue: Shared Pool of Meaning

" Participants [in a dialogue] find that they are involved in an ever changing and developing pool of common meaning."

Morning pages and journaling


Cave Day/Deep Work

Episode 006: Sara Holoubek on Human Companies and Solving Problems that Matter

Invisibilia: Flip the Script (non-complimentarity)


Natural Cycles Model of Creativity

Dave Gray on Drawing Conversations and Liminal Thinking


Today I talk with Dave Gray Author of Gamestorming and his new book,     Liminal Thinking. We kick things off with a Zen story and dig into why Dave wrote this new book. We hit on a wide range of topics from the nitty gritty of facilitating group conversations to organizational change being fueled more by emotion than reason. Dave's books have always opened new pathways in my brain, so I hope you enjoy unpacking some of the lessons inside with me.

One of the reasons I pulled the opening quote about drawing is that it's without a doubt the most powerful way to transform ANY conversation. Most conversations have one interface: the air. Once it's past your eardrums, I have *no* idea what's really going on inside someone's head! Drawing makes sure there's a tangible record...hell, a paper trail, of our conversation, what we've agreed to, what is in or out of the conversation. A few months ago now I helped my mom and dad work out some scenarios around selling their house and moving someplace else. Me and my brother, together with my folks, generated as many options as we could: They move, and rent out their big house, they sell it all and rent something else, they sell and buy and so on...we made a big poster for each option and then stuck up comments on each, using a format called "Rose, Thorn Bud"...which not to be too meta, is also a conversation design: We could have just done plusses and minuses, we could have done a SWOT analysis on each...but Rose Thorn Bud (which is from the boy scouts of america) is a kind of "friendly" design for conversational analysis.

We used different colors for Rose Thorn Bud, a trick I learned from teaching design thinking with the LUMA Institute...and after our meeting we had a visual heatmap of how the whole family felt about all the options on the table. It really helped my folks step back from the confusion of choice and get some clarity about the steps ahead. And it helped my mom realize that she and my dad haven't tried living in enough other places to make a choice about living somewhere else...and that they ought to figure that out before they sell.

That, in essence, is Dave's point about drawing making a series of triangulations for a conversation. Rather than one person trying to hold all those points in mind, we used color and space to do it for us...a board for each future for my parents, and a map of each future.

Another point Dave makes towards the end that I want to highlight about conversation design...when I'm designing a group workshop, the question of size and time comes up. He talks about watching people at parties, and how 3-5 people can "hold" together pretty naturally...but at 6-8 it splits, unless there's someone holding it together, someone famous, magnetic or especially entertaining. There's some math there, just like how paper increases the points of triangulation to give clarity. If 4 people generate 3-5 post-its that's about 20 stickies, and lot's of possible combinations as they try to discuss and organize them all...if you add just one more person, that's 25% increase in raw information...and increases the combination possibilities exponentially. To expect that group to process the increased information in the same period of time is just unfair! That's where a facilitator can help, by making a first action clearer (and taking some options off the table) or by giving more time, a clearer organizational framework, making the stickies all contain the same types or categories of content, or by making sure the group sizes are all consistent. On the face, conversation design for group work can seem so fuzzy, but I feel like there's a lot of quantitative thinking and actual MATH that goes on beneath it.

Show Links:



Liminal Thinking

LUMA Institute

zen flesh zen bones


Power in organizations


Finite and infinite games


Morning pages and journaling


Monkeys watching monkeys


Candid Camera Video of elevator conformity

Sara Holoubek on Human Companies and Solving Problems that Matter


Today I talk with Luminary Labs CEO and founder Sara Holoubek. Luminary Labs is a really unique company that both consults with companies on strategy and also helps run massive open innovation programs for organizations. We talk about working on problems that matter, on how humans have always been more nuanced than marketers and how companies need to be creating Intelligence Engines.

One of the things that Sara helped me think about is an idea i've been noodling with about Complimentarity vs. Non-Complimentarity. How in situations, you have really only these two choices: to go with or against the current tide. Sara helped me see that the conversation between a company and the culture it's in is very similar to the conversation two people might have! Companies face that choice, too. Only, too many companies choose to go along with trends or not...not intentionally, but mostly unintentionally.  And that's the thing about design: everything is designed,  either well, or poorly, intentionally or unintentionally. Sara clearly helps companies and the people in them be more intentional about their work.

 In trying to re-design a conversation you're in,  you can shift patterns by consciously pushing with or against them. David Bohm tells a great story  about this in "On Dialogue"...a psychologist was treating a young girl who wouldn't talk to anybody. After an hour of fruitless attempts, he was exasperated and said "why won't you talk to me?"

"because I hate you" she countered: She was pushing *back* on his energy, you see?

So he asked "how long will you hate me?"

she said "I'll hate you forever"

Then he kept with it, taking the logic further "how long will you hate me forever?"

Somehow, this broke the spell and the little girl laughed. He kept questioning her refusal... somehow, taking it seriously helped shift it.

What is that behavior? He somehow accepted what was happening with the little girl, but questioning it in the right way, shifted the conversation.

I learned about non-complimentarity from Invisibilia, an *awesome* podcast from NPR. I'll link the episode in the notes: in the show opening they talk about a group of people drinking wine in their back yard who get help up at gunpoint. They tell the robber they have nothing, so they offer him a glass of wine instead...which flips the whole script of getting robbed. Spoiler alert: it ends in a group hug. Enjoy that episode from Invisibilia and enjoy this episode, too! I hope you learn something about redesigning conversations for your own context...



Luminary labs


David Bohm on Dialoue:


Invisibilia: Flip the Script


Toothpaste Medium Article


Gartner Hype Cycle


The Human Company Playbook


Makers and Takers


Danny Meyer


EdSim Challenge


Avoiding the 20 Million Dollar Mistake:


Gabe Gloge on Reflection, Learning and Language as a Tool for Thought


Today's Episode is a bit...unusual. My friend Gabe Gloge is interviewing me, so I'll be yapping a lot more than normal! His company,, helps organizations become learning organizations by breaking jobs into skills...and we try to do this for some conversation design skills!  We talk about how to break down engagements into discrete steps, tools and triggers, how a reflective practice accumulates benefits over time and how mathematical reasoning figures in all this. Enjoy!


Show Links





Dave Grey


Liminal Thinking


Persona Profiles


Excel Timeline example


The Tick: On Counting Syllables Vs Writing a Haiku in action


Agile Story Estimation

Johari Window


The Learning Organization


David Whyte's 3 Marriages


Active Listening Script


LUMA Workplace


Inductive/Deductive/Abductive reasoning

Sarah Gallivan Mitchell on Not Listening to all your users at Once.


Today I talk with Sarah Gallivan Mitchell, Product Owner of in-car interfaces at Faraday Future, a company focused on the development of intelligent electric vehicles.

Sarah is an Ace product designer and it was a lot of fun to talk with her about her work through the lens of conversation design. We touch on some big questions, like “How can software be sincere?” and “What’s the difference between manipulation and Modulation?” And “Why you shouldn’t listen to all of your users all of the time”

Show Notes

Sarah’s IxD17 Talk:

Talk  slides are here:

And content is here:

Ixd17 link (video to come)

Faraday Futures

Discussing Design

Crossing the Chasm

Death Talk from IxD17

Agile Introduction

Active Listening


The Easy Hard Problems:

Paul Pangaro’s IxD17 Talk

Leland Maschmeyer on Negotiations and Hallucinations


I first met Leland when he was giving a talk at SVA’s Design Criticism Program back in 2010 and he referenced “Finite and Infinite Games” by James Carse...I knew, right then and there, that we had to be friends!


Lee is the Chief Creative officer at a food company which will not be named (for reasons...but linked here), which Fast Company rated in the top 10 most innovative companies in the world. When I met him, he was one of the Founders of Collins, an agency that Forbes tapped in 2016 as an agency defining the future of brand building.

We had a wide ranging conversation where we tried to find a theory of change: can you only harness trends and follow patterns, or can you create the future? We also discuss how companies need to digest chaos and turn it into Creativity and Action through balancing volume of ideas captured, velocity of ideas turned into opportunities and maintaining a Variety of ideas in the mix. I hope you enjoy listening to Lee as much as i enjoy talking with him!

Links and Notes:

Eight Flavors, by Sarah Lohman

Innovation through features vs The Jobs to be Done Framework

Finite and Infinite Games

IxD17 Users versus Owners (video not posted yet!)

Sketch notes at

Reinventing Instagram:

Harvard Negotiation Project and classes

Other book mentioned:

On Improv:

Rejection vs Acceptance vs. Creation


On cherry blossoms and cradle-to-cradle-design

My whole life is waiting for the questions to which I have prepared answers.