Designing the Organizational Conversation

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Today we are talking to my friend and client Jason Cyr, Director of Design Transformation at Cisco. We have a wild and rambling conversation about designing conversations on at least three scales: as a facilitator of workshop experiences, a designer of design processes and as a leader of a transformation effort in a larger organization.

Like anything else, conversations can be designed with a goal in mind: speed, effectiveness, clarity, joy. How do you intend to proceed towards your goal?

The very first story that Jason tells us shows how knowing your conversational goal is key: Jason tells us about his Uncle Rowley and how Jason’s mother pointed out the ways in which Uncle Rowley was as talented conversation designer. It seemed like he designed his conversations with an overarching purpose, regardless of the objective of any individual conversation. His purpose, his higher goal was to make people feel good. Did he do it in order to be successful, or was that an outcome of his purpose? Sadly, we can’t ask him...but there was clearly an aspect of his way of being that enraptured Jason as a boy - he wanted to be like him. 

As an aside: One of my favorite topics in conversation dynamics is about how power shows up...the type of power Uncle Rowley exerted over young Jason is called Referent Power - the power of charisma.

Jason is now responsible for designing a much bigger conversation at Cisco - how teams work together and how teams of teams communicate and collaborate. One key way he’s doing that is through enabling his organization to apply the tools of Design Thinking to their internal and external challenges.

What my conversation with Jason highlights, is that this conversation takes a long time....the cadence of transformation is not the quick rat-a-tat-tat of a stand-up meeting. It’s a steady drumbeat of regular workshops and consistent follow-through. It’s a healthy reminder that change takes consistency, clarity...and time.

Jason has a simple three step transformation process that he shares:

  1. Start with the Coalition of the Willing

  2. Make more evangelists

  3. Craft stories that share themselves

How does Jason pull people into that conversation? It seems like he uses the same skills he learned from his Uncle - making them feel good, like they are part of a bigger narrative arc - a growing capability and practice inside the organization, one that can and does deliver value to the organization...even if it takes 6-9 months into the effort. This is charismatic power on an organizational scale. People want to be part of a positive story.

How does Cisco design the design thinking conversation? Jason shares four principles of Design Thinking at Cisco and they are so delightfully on point that I wanted to repeat them here:

  1. Empathy. We are always designing for someone else’s benefit. Somebody else is going to consume the thing or the thinking or the product that you're making. Do your best to understand that person so that you can build something desirable for them. 

  2. Go wide before going narrow, whether you're trying to choose a problem to solve or whether you're trying to find a solution to that problem, explore a little bit before making a decision. Try and reframe that problem and dig into that problem before tackling it. Try to generate multiple solutions before picking one. And it doesn't have to be a lot of work.

  3. Experimentation. As soon as you think you have a good idea, how quickly can you figure out what's wrong with that idea? We do that by experimenting, putting it in front of people, having them react to it.

  4. Diversity. Be thoughtful about who you bring into the conversation around the problems that you're solving. Make sure you have the appropriate definition of diversity and make people of all genders and colors feel welcome. Jason also asks: are we including the right people from across the organization, ie, engineering and product or design? Maybe we should be including sales. Maybe we should be including other parts of the business.

I’m so grateful Jason took some time to sit down with me and share some insights on how to lead a design transformation in an organization and keep the conversation on track, moving towards it’s ongoing goal...I hope you enjoy the conversation as much as I did! Also, be sure to check out the episode Jason referenced, where I interviewed Jocelyn Ling from Unicef’s Innovation team on Disciplined Imagination.

Show Notes and Links

Referent Power: https://en.wikipedia.org/wiki/Referent_power

(one of my favorite types of power!)

The six types of power: https://www.linkedin.com/pulse/six-types-power-leaders-john-prescott

Jocelyn Ling’s episode on Disciplined Imagination https://theconversationfactory.com/podcast/2019/8/27/disciplined-imagination-with-jocelyn-ling

10 types of innovation: https://doblin.com/ten-types 

The book: https://www.amazon.com/Ten-Types-Innovation-Discipline-Breakthroughs/dp/1118504240

All process is the same

https://www.interaction-design.org/literature/article/5-stages-in-the-design-thinking-process

https://www.ibm.com/design/thinking/page/framework/loop

POST method: Purpose, Objective, Structure, Timing. Adjust your ST based on your evolving understanding of PO.

Facilitation Means design experiences and conversations: https://medium.com/@dastillman/facilitation-means-designing-conversations-24bac966076e

Creating Change in three steps:

  1. Start with the Coalition of the Willing. 

  2. Make more evangelists

  3. Craft stories that share themselves

Full Transcription

Daniel:            All right, Jason, I'm going to officially welcome you to the conversation factory. Thank you so much for making the time to have this conversation with me.

Jason:              Thank you for having me. I'm excited to be here.

Daniel:            Awesome. So, what would you say your conversation superpower would be?

Jason:              I think that one of the things I'm good at is making people feel good about themselves in a conversation. Like I really do try and draw out, the positive in people. And I'm genuinely, I think one of the reasons why I've, had a successful career in design is because I have a lot of empathy for people. I am truly very interested in them and interested in learning about them.

Jason:              And so I tend to really, try and have positive conversations with people and really try and understand what their superpowers are, which in turn makes them, I think feel pretty good. And interestingly enough, it's something I learned from one of my uncles who's very successful in business. And it was something my mother pointed out to me when I was very young.

Jason:              I remember it clear as day. We were in a grocery store and we happened to be with my uncle who met a former colleague or something, and he had this wonderful animated conversation that clearly left this person feeling really good. And my mother pointed out, watch how Uncle Rowley interacts with people. That's one of the reasons why he's so successful is because people come away from his conversations feeling really good. And interestingly enough that stuck with me and I don't know if that has an influence on why I do what I do, but I think that I do try and always draw out the good in people.

Daniel:            That's so interesting. And you anticipated my second question, which is like, what's the origin story of that superpower? And it seems like that little moment where it was like, this is how you get ahead, which is by connecting with people, which is really beautiful.

Jason:              In fact, I've realized that I've never, acknowledged my uncle for that moment. And so hopefully he can hear this later.

Daniel:            Thanks uncle. And this goes to this idea of like we learn patterns, like both good and bad in our histories. And like you said, I assume that this ability to empathize, to take the perspective of other people and to connect, how could that not help you in your work?

Jason:              I think it helps in anything and it's something I'm trying to pass on to my children as well, and helping them understand when they're, whatever, dealing with tough personalities or tough issues, at school or with friends or whatever, trying to help them see that there's another person in this equation. And what is it that you can learn about how they're experiencing it and feeling that'll help you navigate the situation.

Daniel:            So I'm wondering if we can then take like another step back and talk about like the work you do and your origin story. Like how did you get into the work you do and what is it you do now?

Jason:              So my origin story I think is kind of, crazy because I didn't take a typical path of, I'm going to be a designer or an engineer or whatever and go to school and strictly pursue that. I've always been creative in the work that I do. I had the advantage of the fact that my father was a firefighter, a career firefighter growing up, and he had these side jobs, like most firefighters have these side jobs.

Jason:              And, he sold art supplies for a long time, and we had a basement full of samples, art supplies samples. And so growing up I had this unlimited resource of like, paints and pens and crayons and markers and airbrushes and oil paints. And I took advantage of it. And so I was always very creative. Through high school I started doing a lot of graphic design work and started to commercialize it and sell it.

Jason:              And it just happened that it was, in the sort of mid '80s, early '90s when the migration of design was really moving onto the computer. And I was doing a lot of commercial sign, like hand painted signs and kind of old school stuff. And I had to start laying out these signs on the computer because of the digital transformation and because signs were going to vinyl, cut vinyl. And that's when I got introduced to things like Photoshop and CorelDRAW and-

Daniel:            CorelDRAW.

Jason:              ... these tools.

Daniel:            That's taking us back!

Jason:              Right.

Daniel:            Yeah. That was the shit.

Jason:              And so that sort of led into this transformation towards web design. And, I started, my first sort of real corporate job as a web master, which is why I was in Connecticut. I was working for Thomson Newspapers, designing and building an intranet application for them. And that sort of morphed into a career as a front end developer, in the early '90s in the security industry for RSA Security.

Jason:              And that's when I got my first glimpse at like user experience and that there was this whole sort of practice around, being thoughtful about how we create these UIs and these experiences for people. And I just really, really geeked out on that idea of building this deep sense of empathy for who it is that we're trying to solve problems for and really understanding what they're trying to do and be thoughtful about creating an experience that helps them.

Jason:              And so I spent a lot of time in this security world. I realized that I needed different experiences, went into like entertainment brands and had my own agency for a while with a partner. We worked for everything from, work for Disney and Ronald McDonald House and the Canadian military and like all sorts of projects. And then ultimately went back to working for a more established startup that got bought eventually into, Cisco. And that sort of leads me to where I am now.

Jason:              And I'm currently a part of the security business group at Cisco, which is, a small part of Cisco, but on its own, a massive business. It's about 5,000 employees, upwards of $3 billion in revenue. So it's a huge business on its own. And I came in with this startup where I was leading the design organization for the startup. I led a design organization for a little while within Cisco.

Jason:              And then I realized that the skill that we use as designers, design thinking, this ability that we have of trying to understand people and design for them, can be applied much more broadly within the business. And so I set out to really change the way that the rest of the security business was working by trying to teach them these tools and encourage them to start thinking the way that, that many designers think in the work that we do.

Daniel:            And so we're going to, I want to get into the capability and capacity building conversation in a minute, but I kind of want to go back because you just have this really unique perspective on, when did in your timeline as a designer, did user experience design and like design thinking become part of the conversation for you? When did you feel like you were in that dialogue with that larger idea?

Jason:              I think it was the early 2000s, when I started working within an established design team, for RSA Security, which is a pretty big security organization. That's the first time that it became part of my language. And I recognize that user experience was a thing. User centered design was a thing. Human computer interaction was like a degree that you could go and take that was specific to this stuff.

Jason:              We had the benefit of a usability lab where we could go in and watch people use news products. And so I think as soon as I recognize that this thing that I was deeply interested in, it's like that moment where, I don't know, you find your tribe or you find your people and it's like, whoa, there's other people who are like really excited about this stuff. This is great.

Jason:              And, I had the benefit of working with some great leaders in this space who really nurtured my learning and brought me along, and matured my thinking around all this stuff. And I suppose that's what led to me starting an agency with a friend of mine and a colleague of mine, because it was just something we were so passionate about bringing to the world and talking about.

Daniel:            That's so cool. Because I mean, in my own evolution in design, I feel like design thinking wasn't taught in design school, neither was, I went to industrial design school and it was only when I came out that I became aware of all of these other types of design and all this larger, more expansive language. And it really was the UX community that was speaking about understanding the customer or designing for the customer and being really structured like watching Jon Kolko and Dan Saffer talk about like really being intentional about your process. It was inspirational for me. What were some of your, I don't know, influences who's part of your internal dialogue, when you think about design thinking and designing for the customer? Like, what are the voices that are echoing around in your brain?

Jason:              That's an interesting question. I don't know if I could put my finger on anybody in particular. Like, I mean, there's so many industry personalities that, I was always reading or looking up to, and a lot of companies that I was really interested in and following, whether it's, Cooper or IDEO or, so many great, design organizations. I don't know. I can't really put my finger on anyone in particular. I can't really put my finger on anyone.

Daniel:            In a way, that's what sort of being in the conversation means. It's like there's this meilleux there's a marketplace of ideas and it sounds like you've just really absorbed a lot of it.

Jason:              Yeah. I love learning. I love new information. I really enjoy a great example. So, I was telling you about the story of listening to your podcast last week, of like really trying to be mindful about taking breaks when I can to get away from work, especially when I'm trying to solve hard problems. And I was deep in trying to plan a for a workshop that I'm helping some people with at Cisco, and I took this break for an hour, listen to your most recent podcasts and in it, your guests was talking about the 10 types of innovation and referred to this book.

Jason:              Well, that's the sort of stuff that really triggers me. So the minute I got home, I look up this book, I ordered it, I have devoured it since over the weekend and realized that, Oh my God, there's all this great material in here that I can apply to this problem that I was wrestling with and try to design this workshop.

Jason:              So I think as it relates to design thinking, I'm really quick to identify something and trying to experiment with whatever it is that I've identified, whether it's a good idea or a new resource. And I get excited about it and I like run with it and it'll be the thing that I talk about. Like I've already recommended the book to everybody on my team. I've like, it's been the thing that I've been talking about in most of my conversations this week, and that'll run its course and then I'll do the next shiny thing that inspires me and interests me and I'll go down that path and see what I can use or learn or leverage from it.

Daniel:            Learning from other people. It's interesting. I had really, that conversation is with, just for everyone who's listening, that was with Jocelyn Ling who's, an old friend of mine who works in innovation at UNICEF. And my fiance listened to that and she was like, "I've never thought about having the conversation with somebody about how they work and what their working styles is." And she's getting her MBA in sustainability while working full time. And she's like, "I'm going to have the working styles conversation with my next round of teammates." And it's like, and I just love that Jocelyn learned that from someone else and it just sort of spreads... it just spreads like a wave out into the world, which is a great way to learn through conversation.

Jason:              It is. It is indeed.

Daniel:            So let's talk a little bit about like, I want to talk about day one when you were acquired, because I love that you talked about that, your awareness of your emotional state. I'm really curious how you managed it, and a little bit about what you're doing now at Cisco.

Jason:              Sure. So, to back up to that story that we were talking about a little earlier. I was working for a startup called OpenDNS, which was a pretty big, three to 400 person, startup in the network security space. As a startup, your sort of end goal is you're going to either IPO or get acquired. That's what everybody's working towards. And in our case, we got acquired. We got acquired by Cisco.

Daniel:            Congratulations.

Jason:              I clearly remember-

Daniel:            That's not many people get the-

Jason:              Thank you. And that was a while ago now. That was like four, almost five years ago already, incredibly. But I remember waking up that morning and like, I'm sure many of us do. We get out of bed. We ended up looking at her phone right away, and there was this message from my CEO saying, "You're going to see this in the news today that we'd been acquired." And it was like, wow.

Jason:              Driving to work, it was all excitement. Like, this is it, we've got acquired. This is what we're all working so hard for. And then day two, waking up going, but we got acquired by Cisco and I'm a designer and I don't really see a lot of great design work externally from this big company. And I was really bummed about it. Like I was really torn about, should I be staying here? What does this mean for my career?

Jason:              I was wrestling with the idea of would I apply for a job at Cisco if I saw a design job posted? Like all these things we're going through my mind and having these discussions with my team and my colleagues. And fortunately for me, I had this amazing, amazing boss at the time, who talked me off the ledge by really going, "Hey, if you're not seeing the things that you want to see at Cisco, this is your opportunity to go in and change it, and try and be part of that change and be that catalyst."

Jason:              And I've really tried to embody that as I come in to this, what was pretty a nerving uncomfortable situation. And suddenly you open yourself up to these possibilities of actually... and it seems silly at the time. I'm going to have any influence on, a 75,000 person company. But you get in, I ended up finding my tribe internally within Cisco.

Jason:              There's group of like-minded design leaders who were really passionate about design thinking and really passionate about elevating the practice within this big company. And, next thing we're writing a book internally on design thinking and how it can be applied. We're developing this program that has training aspects to it and all sorts of materials that people can leverage.

Jason:              And now that's what I'm fortunate to do as my full time job. I'm responsible for what we call design transformation within the security business group. And this is a group of 5,000 people, that I am trying to equipped with these tools of, great conversation, great design and great facilitation. And it's all centered around, creativity and experimentation and really trying to help people understand that when you hear this thing design thinking, it really has nothing to do with design as most people think of it.

Jason:              It has nothing to do with how things look. It's not about pushing pixels around on a screen. And it's really at its core just about how do we find the most important problems to solve for the people that we're trying to serve? And once we find those problems, how do we generate solutions that are hopefully creative and novel, but also actually solves the problem? And how do we figure out whether our ideas or our solutions are any good as quickly as possible by running these experiments, using prototypes and the like? And so I'm like, I wake up every day feeling fortunate that I'm right now I'm doing my dream job. And I get to-

Daniel:            Hashtag Blessed!

Jason:              I get to focus on really cool work. Like I get brought into facilitating some really cool projects and workshops within this security business. And I also get this great pleasure from teaching these capabilities to others. So we've got an in house training program that we deliver. We travel all over the world, training people within our security business group on how to apply design thinking and how to think this way.

Jason:              And it's really interesting to approach it from the perspective of, not wanting to build an internal service agency. Like I'm not trying to build this empire of design thinkers who are working for me within the business. I'm truly trying to develop these capabilities in other people to the point where if I work myself out of a job in three, four years because everybody's proficient at it, that's great. I'll go find something else really cool to work on at Cisco or wherever else. And so that's where I am today and I'm really, really enjoying it.

Daniel:            That's really lovely. And it's interesting because with design thinking, there's so much criticism of it. On one hand there's people who feel like it's the sun, moon and the stars and there's other people who push back and say, design is for designers. And design thinking is... there's at least one talk that says design thinking is bullshit. And I imagine that you see that entire conversation. What is your feelings about that particular conversation?

Jason:              I believe that it's unfortunate that design thinking has picked up the brand and the title that it has because I think that, that brings a lot of baggage with it. So, yes, I get a lot of, pushback or friction from designers in some cases where they are nervous that I'm trying to teach other people how to think like a designer.

Jason:              But I think they get nervous about it because they make an assumption that these people are going to take these skills that I'm teaching them and go off and try and design their own products, or try and design their own user interface. And that's not at all what I'm trying to do. I'm trying to teach people that these skills that designers have and that they apply to designing products in UIs can be applicable to designing your PowerPoint deck that you're building for your boss, or this sales program that we're trying to roll out or, an offer structure that we're trying to build.

Jason:              And so as soon as I frame it to the design community and that way they get it. They're like, "Okay, you're not trying to get everybody to start talking to customers and start building their own, features into the product. You're trying to get people to just simply start thinking this way as it applies to their own jobs. And that helps diffuse it.

Jason:              And, I think the other sort of friction point, or negative reaction that people have to design thinking is that they say that it's like, well, it's obvious. Of course, you should talk to the people that you're trying to build for and understand they need, and prioritize those pain points and solve them really effectively and creatively. But if it's obvious, why isn't everybody doing it? Right?

Daniel:            Yeah.

Jason:              Like it truly is obvious and it's really easy when you start working this way, but not everybody's doing it. So we're just trying to nudge people in the right direction.

Daniel:            There's two things that, that brings up in me. One is that at the end of the day, design thinking can just look like mindfulness, right?

Jason:              Yes.

Daniel:            It can just look like intentionality and being, explicit about what you intend to do and what you're doing. And one of my realizations is that, that begins to create, safety for people to know that there is a container and a process for what we're doing. It's not just random chaos.

Jason:              It's not just random chaos, and it's being mindful about, oftentimes recognizing what we don't know or recognizing an assumption that we've made or recognizing a problem that we found, and being mindful about how we can take action on this. In my mind, it's about being mindful on how we can take action on it as quickly as possible to learn something. It's all about learning for me.

Jason:              So recognizing, okay, we have a big gap in our understanding on something, how can we fill that gap? How can we learn what we need to learn? Or, wow, we're making a big assumption about whether a user even wants the same or we'll use this thing. Okay, how can we as quickly as possible figure out whether it is valuable to a customer?

Jason:              And it starts, certainly the story that I've started to tell within Cisco is that it starts bleeding into all these other areas that people are familiar with, like, lean. Sort of lean startup approach to building products and agile development. And they're all sort of related. They're all very much related in many ways.

Jason:              And, so what I've realized even just very recently in my journey at Cisco is, there's a benefit to not talking about what I'm doing as design thinking. And sometimes it's just going in and having a conversation with an engineering team and saying, "Hey, I can show you how to kick off a project more effectively by doing these things." And not even mentioning design thinking. Or, "Hey, I have a framework that'll allow you to retro your team projects or your team activities more effectively by doing these things." And-

Daniel:            Talking about the benefit-

Jason:              ... once they-

Daniel:            ... instead of the... right?

Jason:              Exactly. Once they do it and they, hey, this was really great, then I can go, guess what, you were just doing design thinking there, and this whole thing around what you've done, and you can learn more about it. So the benefit before this abstract sort of notion of design thinking is a good tool that we use.

Daniel:            Well, so can contrast that with me or for me. Like I've seen the Cisco design thinking book, and I've worked with organizations where they'll say like, we want to have our own internal branded process versus we want to be agnostic about process or, to you use a weird word, ecumenical, or to browse many processes. What do you think the advantage for Cisco was of creating, putting that stake in the ground and saying, here, this is our book. This is our design thinking book?

Jason:              I think that we wanted to, first and foremost show people within Cisco that this is a thing, like that it's being funded. There's a lot of people thinking about it and trying to do the right thing. And so rather than just pointing at, hey, we're going to use the ideal process, or hey, we're going to use the, Stanford d.school process. Like, I mean, they're all virtually the same. They're just packaged differently.

Jason:              Or the IBM infinity loop and there's all these different versions of it. We chose to try and package it up so that employees would perhaps embrace it a little more. And now that, I have about two and a half years experience in trying to bring design thinking capabilities to Cisco. And in looking back on that, was it the right thing to do? Maybe in some ways that helped us be successful, in some ways that also hurt us.

Jason:              Like having a very rigid representation of a process can also be overwhelming for people. They see this process of discover, define and explore and these activities that occur within each of the phases, and they think, oh my God, if I'm going to apply design thinking, I've got to completely change the way that we're working, and that can scare people.

Jason:              And for that reason, we actually just over the past, even six or eight months have started changing the conversation towards the principles of design thinking that we're trying to get people to adopt. So rather than worrying about going through this sort of seemingly linear process of design thinking, we're like, hey, there's four principles we really care about, empathy.

Jason:              No matter what you're doing in your job, you're doing it for somebody else. Somebody else who's going to consume the thing or the thinking or the product that you're making. Do your best to understand that person so that you can build something desirable for them.

Jason:              Number two, going wide before going narrow, whether you're trying to choose a problem to solve or whether you're trying to find a solution to that problem, explore a little bit before making a decision. Try and reframe that problem and dig into that problem before tackling it. Try to generate multiple solutions before picking one. And it doesn't have to be a lot of work. You can get a lot of benefit from brainstorming solutions for 15 minutes before picking one and going in a direction.

Jason:              Number three is experimentation. As soon as you think you have a good idea, how quickly can you figure out what's wrong with that idea? And you do that by experimenting, putting it in front of people, having them react to it. And then the last one is this notion of diversity. Being really clear about and being really thoughtful about who you bring into this conversation around the problems that you're solving.

Jason:              Is it making sure that we have the appropriate sort of standard definition of diversity, that we've got enough men and women solving this problem or different ethnic backgrounds. But also, hey, are we including engineering and product and design? Maybe we should be including sales. Maybe we should be including other parts of the business.

Jason:              And by focusing on these principles, we're finding that people are like, I can make some pretty small changes to the way that I work. And it's showing some impact by just applying empathy or just applying experimentation or just applying brainstorming or going wide.

Daniel:            So I love having a compass instead of a map, and that's an interesting reframe. So there's a lot of things to unpack there. One is impact. Like, so if we're doing this process, you're training a lot of people. How do you measure the impact? Do you measure the impact of the process?

Jason:              Yeah. We're trying very hard to measure it in a number of ways. And so, in the sort of simplest form, we're using tools like MPS style surveys. So every time, we engage with a group to run a workshop with them. We're trying to measure whether they perceived it to have a positive impact on that project and a positive impact on the outcome of the project.

Daniel:            Got you.

Jason:              Same with when we do training. Do they feel as though it had a positive impact? Over time we're trying to measure things like the number of people who are engaging with aspects of our program. So how many people are we training? How many people are, moving through what I see as sort of a funnel associated with our training? So how many people, come in to an intro course and how many of those people convert to signing up for a two day, immersive hands on, training?

Jason:              How of those people convert to become catalysts that are out there kind of evangelizing for us? And how many of those people convert to becoming facilitators and developing a bigger practice? So we're trying to measure that sort of in the form of a conversion funnel. We're also trying to measure sustained sort of changes in behavior.

Jason:              So when we're working with, for example, when we put a group of people through a two day practitioner training, for 30, 60, 90 days after that training we're very hard to measure who's changing their behavior and applying these principles in the work that they do. So, like anything design-related it's always really hard to measure the impact of it. But we're trying to do as many of the things as we can to measure it.

Daniel:            Because sometimes there's a sense of like design thinking and good process can improve the quality of the experience of doing the work. And that's a completely different metric from velocity of ideas turned into opportunities and opportunities that improve our bottom line. And both have value to a company or can have value to a company.

Jason:              I think, in the earlier days of my program, the only thing we could measure was sort of the NPS style stuff. Because it was just, we're running workshops or we're doing training. And right now the only thing I can measure is how much these people are liking it. But now we've got six, nine months under our belt of running this program within the security business.

Jason:              And like this morning for example, I was in a meeting where a team was showing this new dashboard that shows, sort of health of our customers within one segment of the business. And this dashboard came out of a design thinking workshop that was done six months ago where they realized the way they were approaching a problem was completely off. And they actually took time to understand the needs of our customer success and renewals teams and understood that there was this big gap in what they knew about customers.

Jason:              And we went off and built this really simple version of a dashboard that's now showing them the information they need. And that feels really good because now I can see that, because of this program, because of this training, because of those workshop, these people found a problem that they didn't know existed or they understood the problem well enough to design something that they could deliver to a customer, which is an internal customer. And now that internal customer is actually doing their job much better than they were before.

Jason:              And so we're starting to see more of those examples pop up. And I'm starting, probably the most exciting thing to me is I'm starting to see workshops happen that are not driven by my team, or that my team is not contributing to in any way. You're just all of a sudden hearing about, this group they did a workshop or they're applying design thinking or you're seeing empathy maps pop up as artifacts. And so I'm seeing it take on a life of its own, which is really exciting.

Daniel:            So I want to go back to the funnel because, and I want to connect it to another question, because we talked about this offline, this idea of taking people who are keen on the process to people who have capacity to become catalysts or drivers of the process to go from being, I don't know, consumers of design thinking to being cooks or preparers of design thinking for other people.

Daniel:            And I guess one of the questions I have is like, for some organizations, the answer to this process is to have a standardized process. Like doing sprints, versus it's modular and we need chefs because we're running workshops of all shapes and size and we need people who are really, really masterful to shape those and design those experiences. Where are you on that spectrum of like, we have standardized workshop engagements to it's gotta be uniquely designed for this particular context challenge, et cetera?

Jason:              We're all over the map I think. We've definitely identified a number of opportunities to create what we're calling playbooks, or specific plays where it's like, hey, we know that we bought this sort of tried and true one day workshop format that is great for a team kicking off a new project. Or, we've got this two day format that's really great for a team to, review their strategy and understand what they need to be focused on for the next six months. And we've got a bunch of examples with that.

Jason:              And so we're trying to use those playbooks as much as we can. But they don't apply to everything. So we get like a great example is I had, two VPs come to me recently going, "Hey, there's this really exciting new opportunity we're exploring between sort of two new business units or two business units within Cisco. We think they would benefit from, a facilitated session on design thinking."

Jason:              And at first glance I looked at it and maybe I get a little bit too complacent sometimes and going, "Grab the play X and we're going to play this one." And I sort of tried a couple of my standard playbooks with them and it didn't quite fit and it wasn't right. And there was a lot of back and forth. And one of the things I realized that was really cool was that, in trying to plan a session, we were actually playing out the design thinking process.

Jason:              I was developing what I thought was the right agenda. I would give it to them as a prototype. They would react to it, it would help me learn, just a little bit more about what they're trying to do. And because when I asked them the first time, they didn't tell me everything. And it was only once I gave them this agenda to react to that they were like, "No, but we're really trying to discover this value proposition or something." And I said, "Okay. Do back to the drawing board, create something new."

Jason:              And so, probably the majority of the things that we can do would benefit from a playbook or a standard recipe that someone can execute. But there's like this probably 10 or 15% right now of engagements that really do result in, needing a chef to figure out how to deliver this experience that's going to satisfy, the needs of this customer.

Daniel:            And it seems like the only way you can really do it is in conversation with people who are, you can't just say like, I'm going to run this playbook no matter what. You need to know that dialogue of what's the need, what's the goal, where are you now, what are your capabilities, expanding that circle of understanding the context.

Jason:              And I think that's one of the ways that I've grown the most as a facilitator over the past couple of years because, there's no question. The past two years for me has been the most intensive, facilitation learning that I've had a chance of experiencing, because that's been primarily what I've been doing. Like I probably facilitate a session every one or two weeks.

Jason:              And so it's just a lot of practice and a lot of repetition. And the biggest learning for me has been to be able to have that conversation, to not come in taking that you need to be the guy with all the answers, or girl with all the answers, that you're trying to understand this customer that your stakeholder, you're trying to understand what their objectives are and you're trying to bring them a plan for how to achieve that.

Jason:              But whether it's in preparation for the workshop, you need to be able to have that conversation and adjusting, or even more importantly when you actually get in the room with these people, and two hours in you've realized, my whole plan for these two days has gone out the window because things have taken a turn. But it's an important turn to be able to call an audible, to be able to like pull your stakeholders aside and have that really quick conversation going, okay, here's what I'm seeing.

Jason:              Our plan is out the window. I'm seeing that, Bob needs to talk to Joe about whatever. Do I have your permission to let this play out because I think it's really important? Yes or no. You plan things really quickly. You go back in for the next two hours, and fight for your life and see how things go.

Daniel:            But you also invited the, you don't just make that choice. It seems like you create that opportunity to open up the conversation. And what I love about all of that is, I don't think either of us got into this even knowing what facilitation was, and it seems like there's this, I love that there's this growing wellspring of facilitation is an important mindset and skillset.

Daniel:            For me, I really just started with, I'm designing an experience and I use the exact same tools I was using of experience design to say, okay, well, this workshop is an experience and I'm going to design that arc. The way I would design any other arc of any other experience, and doing it iteratively with your customers. It makes perfect sense to me.

Jason:              Like I think that honestly, it wasn't until you and I have started talking over the past few months that this idea of, we're designing conversations in these sessions, because I was wrestling with this idea that a lot of the workshops that I was going into to do were not necessarily designed thinking workshops. Like, the people would come to me asking for a design thinking workshop, but at the end of the day, in many cases they were just, well, hopefully well facilitated workshops and conversations that led to the outcome that they were hoping to achieve.

Jason:              And so now, unless I'm truly focused on design thinking activities, I've started to use language that I picked up from you, which is, hey, I've spent my career designing products and now I help design conversations. And I've tried to be really thoughtful about how do I bring you this group of people in this workshop, through this conversation that's going to lead us to the outcome? And that conversation may change. It's going to evolve as we go through it. But that's really helped me wrap my head around really what I'm doing now, which is just having conversations.

Daniel:            That's awesome to hear. So unfortunately, like this time has gone by really fast, and is there anything else that we should talk about when it comes to building capacity for this stuff inside of the organization? Anything that any tips or tricks that you can share with the audience about how to really design that conversation on the organizational level, which is, you know-

Jason:              Yeah. I think that, and this is something that I picked up from, Matt Cutler. Matt Cutler was the guy who essentially started the current version of design thinking within Cisco. And I was fortunate to meet Matt when he was just starting out on his journey and bringing all this stuff together. And I sort of jumped on as one of his first followers and first advocates.

Jason:              And right from the beginning, he would drive it home. Two things. One was, we need to approach the coalition of the willing, or we need to build a coalition of the willing. So let's not waste any energy on trying to convince people they should be doing this. Let's find, even if it's just one or two people who want to do this, let's shower them with our love. And so that's one thing that we've really done.

Jason:              The other thing that really stuck with me from him was, a big part of my job as being an evangelist for what we do and design thinking and facilitation. And he used to tell me, "The first job of an evangelist is to make more evangelists." And so I try and give people the words that they can use to have their own conversations around this.

Jason:              So again, I think something that I picked up on from your most recent podcast was, crafting stories that are recalibrate. Crafting stories that people can pick up as their own and tell in their own way has been something that, I don't think we did it on purpose necessarily, but in hindsight, I think that we've done a decent job of it, and so people have been able to do that.

Daniel:            That's such an important thing because that's spreading the story of success. Like who doesn't want to be involved in that journey, once they hear that story.

Jason:              Right.

Daniel:            That's a really cool. So Jason, I want to respect your time and I really appreciate you coming out and sharing these insights. I mean, it's actually a really lovely conversation.

Jason:              Thank you very much. I've really enjoyed it as well.

Daniel:            Thanks man.

Jason:              It's just been a pleasure to be here.

Daniel:            Thanks man. Any parting? There's one of my favorite Tim Ferriss questions is, if there was a billboard on the side of the biggest highway nearby where you live, what would you want to put on that billboard?

Jason:              Oh man. The one thing that has stuck with me a lot, and this is kind of one of the things that I've been geeking out on a lot recently, is this Einstein quote that talks about, if he has to solve a problem, he would rather spend 55... If he has an hour to solve a problem, he would spend 55 minutes exploring the problem and five minutes on the solution. And I think that that's one of the things that I'm really, really, really trying to influence people to think about these days. So I would end with that.

Daniel:            That's awesome. That's a great place to stop. We'll call it scene. Thank you very much.