004 : Designing Conversations that Lead to Innovation with Daniel Stillman


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Where do you begin your conversations on innovation? How do you design a conversation that allows vulnerability, growth, and humility, while remaining open for those who wish to join? This week Daniel Stillman, Conversation Designer and President at The Conversation Factory, joins the podcast as he expands on the elements of good conversations.

Daniel is a Conversation Designer, taking complex ideas, and creating a space where those ideas can be communicated in a constructive light. This week he talks with Steve Chaparro on how he was a physics major but had always wanted to create things. Stillman reminisces on his childhood how it shaped his desire to use his mind but also his hands with claymation Stillman breaks down the elements on what it takes to have a better conversation; he states that whether we mean to or not, we are all designing our conversations, thus impacting the culture around us. 

For Daniel, culture is an integral part of why he chose to become a facilitator and improve the way we have discussions in and outside of business places. He emphasizes that design thinking is empathy, especially regarding when a change in procedures has an effect on a company’s employees. Compassion in the conversations we have allows us to become better facilitators and leaders. Conversations have sizes, structure, and often need to start with yourself before you desire to speak with anyone else.

Here’s a glimpse of what you’ll learn: 

  • Daniel Stillman shares what fueled his hunger for design thinking and conversations 
  • What thread weaves through your entire life, becoming the undertone of what you desire to pursue and study. 
  • The ability to connect the different threads in a discussion and create a compelling picture is the job of a facilitator. 
  • If your company is customer focus, then what experiences are you designing for your customers?
  • Good conversations thread a sense of coherence.
  • Daniel makes a compelling argument, “Culture is a conglomeration of conversations.”
  • Steve chips in a saying from his days as an architecture, “Your physical environment can either embody your culture or it could serve as a reshaping tool.”
  • In 2015, Daniel left Design Gym and learned how to become a better facilitator in Australia.
  • You can diagram conversations, brainstorm conversations, but you revert to your gut instincts when conversations take place. 
  • Conversation leadership is more of a question than an answer. 
  • Design Thinking is empathy. 
  • Stillman places emphasis on the size of a conversation and its structure.
  • Culture is a game, and anyone can play it if they want to, you just have to make the rules clear and invite them in. 
  • Daniel closes with the significance of having a symbiotic relationship with ourselves first and branching out from there. 

Resources Mentioned in this episode:

About the Guest:

Daniel Stillman is a conversation designer and host of The Conversation Factory podcast. He also authored the book “Good Talk” where he describes how to design conversations that matter. He has been helping leaders develop and facilitate meaningful discussions on innovation for the past decade and he believes that how we communicate is an intricate part of culture, and that it all starts from within ourselves.

Sponsor for this episode:

This episode is brought to you by the Culture Design Studio, a consulting firm that helps people and cultural leaders who feel constrained in their ability to engage their employees to become champions for their people through a series of facilitated workshops. They provide a practical and collaborative process to transform the culture within your creative organization.

Culture Design Studio has worked with organizations like Duarte Design, Design Thinkers Group, Red Bull, USAID, Bacardi, and the Office of Civic Innovation

If you’re looking for more than just a consultant and want someone who can facilitate your organization through a structured conversation to transform your culture, Culture Design Studio is the one for you.

Contact them today to learn more about what they can do for you and your company.

Full Transcript: Powered by Otter.ai

Announcer Welcome to The Culture Design Show where we feature conversations with leaders and thinkers. We’re passionate about culture and design. Now, let’s get started with the show.

Steve Chaparro Steve Chaparro, here I am the host of The Culture Design Show, a podcast where I feature leaders and thinkers at some of the top creative firms in the world, including architecture, design, technology and marketing. But what’s the one thing they have in common? They all believe in the power of culture and design.

This podcast is brought to you by Culture Design Studio, we help people and culture leaders who feel constrained in their ability to engage their employees to become champions for their people. Through a series of facilitated workshops, we provide a practical and collaborative process to transform the culture within their creative organization. We’ve worked with organizations like Duarte Design, DesignThinkers Group, Red Bull, US AID, Bacardi and the Office of Civic Innovation. So, if you’re looking for more than just a consultant, but someone who can facilitate your organization through a structured conversation, to transform your culture reached out to us to learn more go to culturedesignstudio.com.

Daniel Stillman is a conversation designer and podcast host at The Conversation Factory, drawing on more than a decade in the product design and innovation world. He helps leaders design and facilitate important conversations large and small in order to improve organizational collaboration and ultimately, innovation. Daniel is also the author, author of “Good Talk” a book describes how to design conversations that matter. Daniel, welcome to The Culture Design Show.

Daniel Stillman Thanks for having me.

Steve Chaparro It’s nice to be here. Good to have you on. I’ve heard you so many times on your own podcast. So it’s great to be across the table virtually from you. So, it’s been a pleasure.

Daniel Stillman I’ve heard people say it’s that like they’ve, who the people who’ve met me first, through the podcast, are like, I can’t believe you’re in stereo, and your voices coming out of your mouth. Yeah, fascinating.

Steve Chaparro Yeah.

Daniel Stillman It’s because I’m just a disembodied voice to so many.

Steve Chaparro Yes, to some people. It’s just a voice match of face to a voice now. So, I want to go away back, Daniel. So, I want to go back to your childhood. Where are you from? And what was growing up…what did that look like?

Daniel Stillman Wow, that is way back. Because I’m getting older all the time. I was born in a small island off the coast of North America. It’s only 13 miles by six miles. You may have heard of it. It’s called Manhattan.

 Steve Chaparro 

Ah, yes.

 Daniel Stillman Tiny little slip of land. It’s tiny. I it’s funny. So I’ve been to lots of cities. I grew up in New York, as I said, and when you get to a place like Tokyo, they’re like, Oh my god, you’re from New York. I’m like, Are you kidding me? Tokyo is insane. And it just keeps going and going. You’re on a rooftop and you see little dots of light going in infinity. New York is obviously a huge place. But I grew up in a really small town party that I grew up in the Upper West Side, which when I was a little kid was kind of a black, white brown neighborhood. I grew up with really loud, Hispanic music blaring from the street, even though you’re on the 17th floor, it’s still pretty loud. And I remember during the crack epidemic in in the 80s, I thought crack was called crack because it filled the cracks of the sidewalks. And, you know, around the corner for me was, you know, a single room occupancy hotel and on the other corner around the street from anywhere million-dollar brownstones and high rises. So it’s definitely in New York is a strange place.

But my mom is from Queens, but dad’s from Brooklyn and I like to joke that they emigrated to Manhattan to give me a better life. It’s funny like I’m a third generation immigrant but I think I still feel like an immigrant you talk about culture and being like a third culture kid in New York is really a soup of cultures when people say like, what do you love about New York? i? I love that New York’s like the world falafel and dim sum and just eat the world in New York. And we’re just all pushed up together. That’s what New York is to me. That’s what that’s what it was like growing up.

Steve Chaparro I mean, yeah, I mean, I when I’ve ever gone to New York, it’s just amazing. I’ve taken my family I’ve got two kids and and the languages that we hear being spoken on the streets are just amazing that like, that’s just such a cosmopolitan experience. Yes, that I have not necessarily experienced say where I’m from in LA. I grew up in Michigan. But I’m I’m fifth generation Hispanic from you know, you know, family coming from Mexico.

Daniel Stillman You’re more American than I am. Like, lots of layers.

Steve Chaparro Yeah.

Daniel Stillman Like that thing make make America Mexico again.

Steve Chaparro But even even for some of my, you know, Hispanic friends who are literally like first generation, they assume certain things about my own experience when I’m fifth generation, like, Oh, that’s the reason why you’re not 100% fluent in Spanish. But yeah, to that experience of New York, you know, such a really, you know, this mosaic of experiences. What did you want to do when you were growing up?

Daniel Stillman Oh, man.

Steve Chaparro Like, what was the career that you thought you would have?

Daniel Stillman I think…I don’t I don’t know. Honestly. Oh, wait, no, that I think the first thing I ever wanted to be was a claymation director. I don’t know if you remember the California Raisans You might be a similar age to me maybe you’re a little younger. But I remember when the California Raisins came out, and I was like, I loved clay. I loved sculpting in clay. I made little characters for myself to play with because clay was I think cheaper than all the figures I wanted. My parents got me a lot of he-man but like, Voltron was way too expensive for for my middle-class families like I need my own Voltron. with clay it didn’t work as well because you know, the parts stick to each other. But I my parents did buy me a super eight camera. And I did stop motion animation films when I was like, in like fourth and fifth grade. And I was like, I really loved. I really loved this idea of making figurines move and talk and and engage. That was the first thing I ever wanted to do.

Steve Chaparro When you’re in high school, what were you prepping yourself for? You know, as you’re thinking about

Daniel Stillman My my parents are very, very high-minded people. So, I think I wound up doing physics. I knew I sort of thought I would go study science because that’s what Jewish kids do when you’re when you’re smart. It’s like doctor, lawyer, scientists. And to me physics was the, my parents were really into philosophy and Eastern philosophy and seeking the truth and realizing themselves, they’re into that sort of stuff. And for me, physics was a way of understanding the world and as deep away as possible. When I went to college for, I got a master’s in physics. And there’s this classic snarky physicist quote, from blanking out on who said it. I can visualize the experiment that he performed, which is the gold foil experiment that showed that atoms had very, very small, massive dense nuclei when you shoot, basically heal alpha particles that some of them bounce off, which was like an Rutherford, thank you for sparking my memory. Rutherford said in science, there’s only physics All the rest is stamp collecting. And so this idea that underneath biology, underneath chemistry underneath Earth Science, all of which I loved, I love the sciences. underneath all of it was physics, understanding why something really happened is happening. And that perspective, I think, really has infected still, to this day, what I do with with in the design work, because it’s like wanting to know why something is happening, not just doing it, and not just fixing something, and it’s great that the fix works. It’s like, Well, why did the fix work? What’s going on underneath it? So that’s that that real hunger for why is what the physics was all about?

Steve Chaparro Yeah, no, I think that’s really interesting, because I mean, obviously that was probably one of the questions I even had listed is like, How does a physics major, end up designing conversations? But I think that gives…

Daniel Stillman I can i can also draw the arc for you is that when I got out of school, it’s like, it’s basically a useless degree. You might as well have a degree in poetry because you need to you can’t just get a job. There’s others, you kind of have to visit

Steve Chaparro Is it a pathway through academia?

Daniel Stillman Yeah, it’s academia. You get a PhD, I did research and I was like, ah, but I loved education. I love teaching. I always tutored kids. I tutored people who are going through the courses that I was going through at the same time, which was like eye opening to like, learn and teach at the same time. And I think that’s really how I learned was through teaching. And so for when I got out of school, I thought to myself, well, maybe I can do science exhibit design. You think about like the figurine and then making things making dioramas is how I always got extra credit in grade school. Good. Like, whatever. Book your reading, just make a diorama. And you get extra credit. It was super fun. So I did that tons tons of diorama making. So I never really thought about the connection between my, my claymation addiction and okay science exhibit design. What if we could design a space where people enter into it and they can automatically learn about whatever it is they need to learn about, right? I loved the Museum of Natural History as a kid, I actually managed to work there. I’ve managed a research lab for several years. There’s a secret research lab on the roof of the Museum of Natural History. The elevator to my office was big enough to put a Stegosaurus and it was a wonderful, wonderful job paid me literally almost nothing. There was no career path, but I got closer to seeing what exhibit designers did.

And then I wound up going to design school at Pratt because somebody said Oh, well if you want to exhibit design, Pratt has a program in industry. design, but you can you’ll learn how to be a designer because you’re not. And yeah, you’re not a designer. And you’ll also there’s a studio and in an exhibit design, and I did that. And I was like, Boy, that’s a tough industry, political slow moving. There’s an exhibit designer out there, I’m sorry, prove me wrong, but it’s hard. And nobody taught me about stakeholder management and Human Centered Design is what I learned about in school. unintentionally, they didn’t call it that this was design thinking was really just on the fringes in ’05, ’06 in the world, but design was shifting from just making things to making experiences, but we didn’t call it that yet. And so, when I got out of design school, I got a job as a user researcher and strategist because that’s what I knew how to do. I knew how to talk. I knew how to talk to people and talk to clients and it’s great question of how do we design the future of blank for our client? Right? And what’s ultimately frustrating about that process is you can talk to them until they’re blue in the face, about what you’re learning in the streets and in the world. But, and even if you take them along with you on the ride, and try to tell them the stories that come on the interviews with you, whatever you wind up, making kind of tends to dissolve into the bowels of the organization, kind of like Han Solo would have in the pit of the sarlacc. Where not for a certain young Jedi, rescuing him.

Steve Chaparro Yes, I think I know his name. I love I love hearing people’s journeys of how you know they it’s almost like you just pull a thread, and you just see what comes from that pulling of the thread and there is a thread through everything you’ve described. And I’ve even seen a thread between people that I’ve talked to that are essentially for lack of a better term master facilitators, and that comes from there is this unique, the shared experience of having the heart of a teacher of wanting to not just be satisfied with just conveying information, but that there is some sort of transformation in that person into the your point of physics, getting to the heart of the matter, like to the why of it. What are some of your thoughts about that?

Daniel Stillman About which part of it?

Steve ChaparroAnything that stood out to you?

Daniel Stillman Well, so it’s interesting that use the word thread. I’m not sure wondering, like, what made you use that word, thread?

Steve Chaparro I think because when I think of my own journey, I think of the what is I have had people like question, certain career changes or changes that I’ve made. So my undergrad is in architecture. I started in the industry of architecture, but then I went to real estate development, and then I became a financial advisor. And then I went back to real estate, then back to architecture now into the world of innovation. So, so but people have asked me like, How in the world did you make those changes? And there is a thread through everything. And I’m even at the age of 45. I’m learning to discover what that thread is. And it’s it’s been a path of discovery for myself, of understanding what is similar and all those things that I pursued.

Daniel Stillman Yes. So, the word threading is so fascinating to me for like so many reasons. So the first reason is highly recommend if anybody’s listening to this, maybe the best book about experience design was not written by a quote unquote experienced designer was written by a restaurant on tour, and it’s called setting the table and it’s by Danny Meyer, who was 11 Madison Park, Union Square cafe, and the Shake Shack, which we all know and love. And Danny Meyer’s book, and if he’s listening, I’d love to have you on my show for you too. He talks about his process of creating a new experience IE a restaurant. And, and his the first stages collecting dots. And the second stage is connecting dots.

And you just look at what design thinking is. And I know you consult on design thinking as do I. And that’s pretty much what we advise our clients is go out go broad go wide, collect dots. And this idea of being able to connect dots is the art of creating a thread. We build the thread. We tell stories, we tell narratives. And what I’ve learned for myself is my mother, who will also listen to this podcast. She listens to all of my episodes. It’s amazing.

Well, it’s not just that the fact is, people are like, oh my mother, like I have to explain what I do to my mother Mike. My mother is smart, and she gets it because she gets me and she loves me. My mother has a difference in what I would call her conversation operating system for that is very high when it comes to things narrative threading, everything is a story. Right? But a very coherent story. Whereas my friend Darcy, who I also talked about in my book, has a high coat has a high propensity for like, multi narrative threading. When you have a conversation with him, it goes everywhere, and he always brings it back. And that bothers some people. Some people want to stay on one thread, and mono threading. And some people are multi threading is really good friends, when they have a conversation, go like 610 threads. They’re like talking about their feelings. And the movies they’re going to see next week and what they had for dinner yesterday, back and forth, back and forth. All the conversations are happening at all all at the same time.

What’s really interesting about the word threading to me is that you’re absolutely right. It’s 100% when the most important skills a facilitator can have is the the ability to paint a picture for people about what we’re going to do and why it matters, to tell that story and to collect to make all the data fit together. It’s one of the reasons why. In the book that I wrote, I made a live stream before I wrote the book. I, I was studying in my podcast, this idea of what it means to design a conversation. And you know, as well as I do with design, you’re designing a thing. Whatever it is a service or an experience, eventually comes down to there’s a touch point. Maybe I’m just saying this because I’m an industrial designer, I’m holding my water bottle right now, which makes that sound. When you design a thing in industrial design, when you design a thing. If you want to make it better, I can tell you, okay, fix that curve or make it lighter. It doesn’t fit my hand. Well. You know, this, this catches here. I’d like to loosen that up. And so there’s physicality to the materials of design are very clear.

With UX design and service design and experience design, becomes so much more ephemeral. And so the question is, if customer experience is the core of everything that most companies do, what are you designing when you’re designing experiences. And that’s why Danny Meyer’s book is so interesting because the the idea of setting the table is so core, you can’t force somebody to have a good meal. You can only set the table, somebody can come to 11, Madison Park, one of the best restaurants in the world, and have a bad date because of who they’re with. Or they could be worried about their job, or their parents could have just passed away. They could be having the best meal in the world. And it doesn’t matter. They’ll have a bad night. Danny Meyer cannot control that. And banks and legal firms and insurance companies can design experiences, they can shape them, but you can’t guarantee all the time.

And so for me, the question is, if we are designing these experiences, what are the elements of these experiences, and I had a woman from Google on my podcast several years ago, who was from the conversation Design Group at Google. And what they were doing was trying to model human conversation so that obviously they could shape it better. Google actually a really interesting perspective on conversation design. And they’re turned out there’s this whole world of theory of conversation theory, which I do nothing about. And they talk about threading the thread of a conversation, a single conversation. And and but yet no one can really define it very well for me, but you and I both know, this, that good conversational threading is a sense of coherence. And when the comfort you’re like, Hey, what are we talking about here? What I’m sorry, we’re jumping all over the place. Like, what’s this? What are we even talking about here? And we’ve all had that experience inside of a meeting. We’ve all had that experience that update. Right? If you can remember back that far. I can remember back that far. And you’re like, what are we here talking about? Like, what is going on? I’d like to write a book called What the fuck are we talking about? If I can curse on this podcast, I apologize. But so that’s why threading is interesting to me. And you can see it I have a multi threaded, I there was like three stories there. But threading is this really interesting thing. And it’s at the core of not just what we do as facilitators, but it’s, it’s a human thing. Right? It’s important to remember that it’s a human thing when somebody’s like on a good facilitator, I don’t know, blah, blah, blah. I’m like, you do it every day.

Steve Chaparro Yeah. And I do think it’s a muscle and I do think that there are certain skills like you know, in certain design industries or you know, that I’ve worked at or designers, I believe that to facilitate the skill of facilitation is so necessary because I’ve been in, say, a discovery session where a designer is just talking and talking and they’re, they’re connecting things in their head and they’re verbalizing things, but they have no clue about how the room Yeah, is empathy. Yeah, that empathy that social starts at home. Oh, my goodness, there’s it just some people absolutely lack that ability to read the room and then To be able to respond to but I think to your point of being able to articulate some of those things that the room is saying they may not be saying it in a very coherent or in a very in a shared manner. But they’ve been able to pick out okay, that person is saying this that this person is saying that all these people are saying certain things, the thread that is starting to emerge. And I think that’s what I love about sort of design thinking is this idea is that things can bubble up. It’s it’s an emergent process as opposed to a very directed process.

Daniel Stillman Yeah, well, so my counterpoint to that is I think facilitation. There’s like facilitation is a really broad word. And I think for like maybe the last year and a half, I’ve been involved in men’s work. Yeah, I should be in my men’s group tonight. It’s Tuesday. I’m here at the control room in Austin instead. And that is a very a different type of facilitation. Right for years my facilitation operating system was based on design thinking, which was hyper time boxed. Moving forward, energizes thinking based, very visual, right, and going from small groups to large groups, really large groups.

My men’s group is about slowing down, way, way down. There’s no writing. I mean, not that there can’t be it’s it’s verbal, and it’s somatic. Its body based. It’s facilitation. But we’re not. It would look pretty alien. And so, when I teach my facilitation masterclass, what I want people to have is range because facilitating a group dialogue with like, 20 people and trying to like, get 20 people to like get to a shared perspective can be done with it. Very, very strong facilitator with strong presence with strong active listening skills with strong threading and connecting skills. But it is a lot of work. And dividing and conquering is another way of facilitating, which we do all the time and design thinking workshops where you push things out to the edges, where you do a lot of paired and solo thinking and small group thinking, and only let certain things bubble up to the top level. And that’s, they’re both facilitation, but for one person, they look at this other type and be like, that’s not like that’s harder that’s not effective, or that’s not connecting people to their humanity, or you’re like all that takes too long. People could look at tastes great, less filling of facilitation, but there’s all so many different ways to be a facilitator and I don’t want to tell people that there’s a way to be a facilitator. I want people to discover their own their own way to be efficient. elevator?

Steve Chaparro Yeah, I think it’s many times, you know, like, I went to school at Parsons for a degree in strategic design and management. And one of the things that we went through was, there are nine different schools of thought around strategy. And that many of these firms will say, Okay, this is the BCG way of doing strategy. And this is the only way we’re going to do it. And I just came to realize that it’s good to understand all of those schools of thought, it’s good to understand different ways of employing design thinking and consider them as part of your toolbox and to find different ways that you’re able to, to work those tools and those methodologies in your own way. And so that you’re free to exercise, you know, sometimes even your personality and the way you conduct some of those conversations.

Daniel Stillman Yes, and I think the fundamental truth is everyone has to discover their own way. And the end, you do get to your own way. from discovering everyone else’s or do you get your own way from thinking fundamentally, again, as a physicist person to, like, think deeply look deeply. One of the things I was actually looking around the office for a car deck I just designed but I could just give a deck of them to Douglas. I’ve been doing this exercise in my facilitation master class for the last couple of years what I where I get people to generate their, what I would call their facilitation hats. What roles Do you take on as a facilitator? What roles Do you have to take on and off? What roles are hard for you to put on? What roles are hard for you to take off, and we get people to generate those and just do some mapping with them.

And in some of my individual coaching clients, what I’ve found is that it gets them to be able to be introspective about what’s easy for them and what’s hard for them. And if you couldn’t name and notice something you can evoke it. Because you can say like, I want to become more of a, I want to be a better emcee. You can, you can study emceeing right. If you say like, I want to become a better, more fun, or I want to be a better explainer, or a better teacher, or a better nourisher, a better detective, a wizard, more artistic. These are all literal hats of facilitation. I’ve collected like, hundreds of these hats. And I just made a deck of 52 because I thought it’d be fun to do. And it was it’s actually like, it’s very similar to have you ever done any inner inner family systems or inner voice work. So, this is like us. This is a thread of therapy that I’ve actually I do some of with my therapists where you think about like, when you’re having inner conflict, you’re like, Oh, god, I’m so upset with myself for like, I wish I could do blank better, or I can’t believe I blanked. The question is, well, who let’s let’s What does that voice say? To you, and what’s the other side of you saying, and let’s identify those two voices.

And let’s take that conversation that they’re having, and make it explicit rather than implicit, instead of it being fast and abusive. And I don’t think I’m the only person who has inner voices that beat the crap out of me all the time. Slowing that conversation down, taking it outside of your head, and putting it in the room or on the wall, allows you to have a conversation with yourself. And I, the other day, I asked somebody how they were using the cards and then we’re going to use it to hand out roles to people like you’re up this part of facilitation, you’d be this. Everybody’s a facilitator in the room. I used it for Okay, how do I want to show up today? I picked out three cards. It was fun. nourisher and detective and I was like, That’s fascinating. That is totally what I’m going to be in this meeting that I’m going to go into right now. It sparked it sparked Join me to like, be like, okay, that’s, I can pull that out of myself. Right. That’s why I want to show up today. Why not?

Steve Chaparro I think that’s fascinating. I think there’s so much so much. I’d be interested to take a look at that as well, because I think there’s different scales that that exercise could be done, right. There’s within oneself between two people within a team within an organization. How, how can a leader take the approach of designing conversations as a way to change, you know, change the way they work? Or even just looking at culture in general of a team or organization?

Daniel Stillman Yeah, well, I mean, the first thing is just taking a step back and saying, I’d like to design it already. puts you in the perspective of thinking about the ends and the means. And then who’s involved. And when you talk about strategy and design, that is just the fundamental thing. Where are we now Where, where do I want it to go? Where might it go? And what’s the gap? who’s involved? You map that out. And you can have a very interesting conversation with yourself. Ask the other person the exact same questions, ask yourself and ask them. And you’re on even footing and saying, Well, I’d like it to go this way. And I can see you’d like it to go that way. People are afraid, I’m afraid sometimes to ask a question that I don’t want to hear the answer to. But it takes it takes a certain type of courage to be able to say like, it’s better to know than to not know. And so that’s having the conversation that like, I think the first line of the book, which I should know is, our lives are defined by the conversations we can and can’t have. And if you literally can’t have the conversation, then it won’t. It won’t happen, right? If you can have the conversation, it might happen. And so I think for leaders, it’s the same thing with like with the facilitators, that’s I’ve used the exact same exercise in the innovation leadership accelerator that I Host where we just say like, Okay, what are your leadership paths? Get clear, as clear as possible about what you want to invoke what your brand of leadership is, although I don’t like using the word brand with leadership.

Steve Chaparro Yeah, it’s understandable.

Daniel Stillman But with culture, it’s the same thing. You’re absolutely right. Culture is a conversation. It’s just like, a conglomeration of conversations. And with culture, culture is a conversation where it’s not necessarily clear who’s quote, unquote, leading the conversation. But conversations have components, like I’ve come to the conclusion that you can design a conversation and there are components of a conversation that are desirable. Some are easy to see. Some are hard to see some are slippery, some are very sticky. The conversation operating system that’s on that’s on my website, I can send you a link to it. I tried to figure out and threading is one of them. But every conversation has a place. Our conversations happening in the air right now. Right and the interface between us is all the technology between us when you’re having an interview. Conversation versus conversation. If we were doing this at a whiteboard together, we’d be having a very, very different conversation. That’s why the folks from mural are so interesting to me, because they create a conversation that creates a broadband connection between people. And so, always ask is where the conversation is happening, supporting or not supporting the conversation you want to have. When we talk about culture. Just look at your space. What is the space say about your culture?

Steve Chaparro Your speaking my love language. I mean, that was from my world in architecture, where we considered ourselves spatial storytellers that your physical environment can either one embody your culture or it could serve as a reshaping device.

Daniel Stillman  Absolutely. 100% true. Space is space in place. The interface for the conversation either supports it or degrades it. Now here’s the thing like I watch that famous like MIT building that was just like a shooting ramshackle building were like, all the coolest inventions of like the 60s is like building 31, or whatever it was. I can’t remember.

Steve Chaparro I don’t remember I should know as an architecture guy.

Daniel Stillman But the whole point of this is the classic thing of like affordances in an architecture are either it’s over it’s can be over designed or under designed. In this case, it was designed in a very positive way. Because people were like knocking out walls and moving furniture around and connecting things. It allowed them to sort of feel like anything goes as opposed to like, a hyper designed we work space, which is supports a certain type of interaction and feels a certain way, but certainly doesn’t make you feel like you can be Tony Stark and go into hardware mode and synthesize new elements. And just like Alright, let’s shoot some lasers around the place. See that my references are mostly actionmovies.

Steve Chaparro Which are I’m glad that you’re referencing Marvel and not the other the other crew.

Daniel Stillman Have I did you see the Joker on the plane? And it was the Joker. Interesting.

Steve Chaparro Very good.

Daniel Stillman Pretty intense.

Steve Chaparro Yeah, it was very good. What led you to start the design or the conversation design factory?

Daniel Stillman Well, so the conversation factory is a pun for me. When I started in 2015, I left the Design Gym, which is a company I co-founded in New York. And I went and traveled a bit and I was consulting with a group called second road in Australia. through a friend of mine, Justin Connor was wonderful, wonderful man and an amazing facilitator. And he had this amazing conversation and he was like; your approach is way too mechanical. You should come out here. We’ll bring you on some projects and we’ll, we’ll break you. That wasn’t his turn. He didn’t say that. But he was like, I think you’d I think you’d enjoy what we’re our approach. And what they called their facilitation practice conversation design. And when I first heard that term, I was repelled, not attracted. Because as a designer designers are very petulant, and possessive lots, any designers listening prove me wrong. I think we work against it in ourselves sometimes. But we design because we like to control, we like to make. And even though I’ve been teaching design thinking to non-designers, since 2010, I, because I thought teaching design thinking to non-designers was a good idea. Because if we could all speak the language of design thinking, Oh, we could all collaborate together. What a great idea. And I still think it’s a great idea. But at the end of the day design and design thinking are different.

And so, when these non-designers are saying, well, we’re conversation designers, and I was like, what does that even mean? But it was really an interesting perspective and it really cracked up in my head and in my progress, from industrial design to user experience design, to when experienced design and service design became Ascendant, I was like, well, and this was even before voice was even really a thing. I mean, 2015 I guess voice design was on the rise, but it wasn’t in my consciousness. And so, when I heard conversation design, I wasn’t thinking of conversational design, or human computer conversation design. I was thinking I was thinking it in the terms that they were talking about it is human systems conversation design, we design the conversation that an organization is having about a problem they’re having, we designed the conversation a team is having so that they can change the direction of their, their business. And I was like, that’s so weird. And I remember I just was it just, it just was a bug in my brain. And I did four interviews. I thought maybe I would start a podcast. This was January of 2016. And I entered Dave gray who wrote game storming with Suni Brown, sorry, Sonny brown and James maca nouveau and Abby covert who wrote how to make sense of any mess. Two really good friends and amazing friend mentors to me. And Philip McKenzie, who now has his own podcast, who’s He’s like, a culture consultant. And my friend Leland Nash Meyer, who at the time was with the Collins group, and is now the chief creative officer at chobani. He’s a badass, and I just like, I don’t know, I picked those four people who I was like, Okay, I wanted to do a conversation with you. And I was like, when I say the word conversation design, you say, Go, and they were like, they just sort of riff on it. And they were like, it’s interesting. It’s weird. It’s confronting. It’s strange. All the things well, let’s talk about manipulation and control. Let’s talk about negotiation versus communication. system’s thinking, blah, blah, blah. And I was just like it just interesting. But I didn’t do anything about it until 2017. I think I just sat on it.

But the conversation design was the conversation factory was, was first just a little holding company for my budding facilitation business because in 2016, I left the design gym and I was traveling and I needed I needed a container for the conversation. And I thought like, well, conversation is interesting, but I wasn’t it was really, it was a slow burn for me. And so 2017 I started the podcast, and really with the proposition of trying to understand what a conversation was made of, if we could design it, and if we could design it, what were we designing, just like straight up investigation. I suspected I hoped that maybe I’d be able to write a book at the at towards the middle of it. Not that I’m Tim Ferriss, but like tools of Titans was like, Oh, come on. That’s just a bunch of podcasts. You never use a really good book form. Tim, you’re listening. I love you Please come on my show. I’d love to have a conversation with Tim. Tim is a very interesting conversation to say.

Steve Chaparro Yeah, absolutely. I mean, his podcasts a, you know, the the the free flow, the ebb and flow, the the vulnerability of those conversations. I love listening to that podcast.

Daniel Stillman Yeah, and he goes between fixed questions and fluid questions. And anyway, it’s fascinating to and he’s evolved as an interviewer because he’s gotten better at it. And I’ll tell you, you’ll see this in your podcast, the worst thing in the world is to be able to look at a graph of your conversations, because that’s what when you look at the audio file, I was like, Oh, god, I’m not good enough listener. I can see what I was trying to break in on them and ask a follow up question. And you can see, you can see the conversation and it changed. Once you can see it, it’s different. And that’s what we’re going to go back to Culture, if you can’t, how do you even perceive the culture? How do you even diagram it? And that’s why people make canvases. Like, okay, let’s talk about the purpose and the goals and the vision, the bubble, blah and whatever. I in my book, I have a section where I talk about the culture of a community. And I use the conversation operating system. The Nine elements of the conversation, operating system, canvas to diagram a community, because if you can diagram, a one on one conversation, they’re all community and organization team. They’re, they’re made of conversations, you can diagram. Any conversation, I did it with ladies get paid, which is a community.

I’m a huge fan of Claire Wasserman came on my show, two, three years ago now. And her community ladies get paid exists to how to say this eliminate, I guess, eliminate the pay gap between men and women. It’s amazing invitation and basically anybody can be part of the community if they want to because they got sued by men’s rights activists for like not letting women into their events, which is terrible. I’m in our podcasts, we actually brainstormed ways that she could integrate men into the community in a in a safe and interesting and valuable way. And so you can diagram that conversation, you can brainstorm conversation approaches, but in the present, you just have to sort of you go with your gut, and your gut is based on what you were taught. And your gut is and then your the questions like what do you do with your gut reactions?

Steve Chaparro Well, we’ve referenced a lot of aspects, bits and pieces of your book. So let’s talk specifically about your book. Your book is good talk, how to design conversations that matter. True story, what led you to write the book outside of being a compilation of a podcast, which I know it’s not,

Daniel Stillman It’s not. Ah, you know, I mean, so there’s a cynical Answer. And then there’s the real answer. The cynical answer is like, you will write a book one day. Because if you want to play the thought leadership game, like, it’s, you know, the book is the new business card, whatever. But I think my dad’s library was full of books, not surprisingly. And what else is a library full of magazines? I think a book was something that I aspired to; I don’t think I knew that. But creating new knowledge from science was interesting to me. And so yeah, that’s one of the reasons why I wrote a book. The other is because like as a as a businessperson, like having a book is the is a way to put your to put a sound out there. One of the other components of a conversation is the invitation. Right? What starts a conversation off? Is it a push or is it a pole? Is it a poker? Is it a shove, or is it an outstretched hand? Right? These are all ways of and a facilitator has to be great at framing invitations. How might we versus how must we How should we How will we? Right? Those are? Problem framing is fundamentally invitation design. Right? You’re not just for weddings anymore.

Steve Chaparro And I think I’ve heard you say that before. But I think the invitation aspect of it is tremendously important, especially when we’ve had historically, the design of organizations has been hierarchical, this top down command and control. And whenever any initiative is being launched, it is basically people are being pushed, or being directed to do something. And so even if a company is going to adopt design thinking, it could be this top down approach and they won’t, and we’ll think it’ll, it’ll gain traction, but if they are invited to, to experiment and be part of it. And that’s one of the things that I’ve been thinking about too is, is how a leader needs to transition from being an architect of culture. To a facilitator of culture, which always includes an invitation.

Daniel Stillman Yes. But is it a real invitation? Or is it a bullshit invitation? Because these things do not exist in a vacuum, right? People remember past abuses and the scars exist. And so when you say, hey, let’s come to this new initiative people like, God, I remember that other initiative and nothing happened with it. Fool me once. Fool me twice. Right? That’s so that’s something that leaders also have to come into contact with. You should really listen to I interviewed Bree Groff. on my show, she spoke at the sprint conference that Google hosted last year. And she talks about the six stages of grief and organizational change. And she has a wonderful, wonderful framework. And she talks about how if you think about the arc of change leaders want to Start at the, hey, we’ve got a new change and now we manage the change. But we don’t start at the very beginning where everyone else’s which is grieving at the loss of what was and also acknowledging what was.

Steve Chaparro I think even in some cases there is a grieving at the leadership level, the leadership level in that many times any change requires probably just as much change for the leader because they’re having to, to lead in a different way. And I think you know, I think of it and sometimes in generational aspects where if we’re going to lead our companies into a new era, that means we need to change the way we lead to become more vulnerable, a little bit more courageous and be more of a facilitator which invites the possibility that they may not be the one to lead. You know, the company to the next chapter.

Daniel Stillman Conversational leadership is is a different type of leadership. You could call it facilitative leadership, potentially. Conversational leadership for me is more of a question than an answer. Like I don’t know exactly what it is. We can probably it’s like pornography or art. We know what it isn’t when we know when we see it. I don’t know if you know that old joke. Like I heard that one before. It’s a it’s like a judge trying to like to adjudicate whether or not something was profane, profane or not. He’s like, it’s hard to define. But you know, when you see it, here, here’s the thing, I think, leaders and this is Brees point. Number he says that leaders who gather together and make a decision, or a leader who makes a decision themselves has already processed a lot of that grief. They’ve worked through it with their coach or with their board or whatever. And then there’s this desire to share something perfect with other people. And today, here Okay, let’s launch day cut the ribbon, we’ll get it started. But everyone else needs to go through the exact same process that they did. And so, this this, you know, this is what we teach in design thinking over and over again, which is empathy. Right? You know, empathy. It’s not just for customers, right? What does it mean to actually try, and perspective take and think about what somebody else is experiencing? Can you go to the balcony, a term that my friend Bob Bordeaux uses? Like I’m quoting people, this is like where I learned, I learned things on my podcast is where I learned things. Bob, who taught the Harvard negotiation Institute workshop that I went to week long, intellectual vacation in negotiation, highly recommend taking a break from everything you normally do and hanging out with a bunch of lawyers and mediators and learning how to like negotiate better, his term was just going to the balcony. Can you go to the balcony and say what does this look like from the outside? Would somebody looking at this deal being done? See it as legitimate? Would somebody else looking at this from the outside, look at these criteria that you’re using? And say, yeah, this looks this looks good. And often we try to like, slide something through or get something done and you’re like, am I acting in such a way as I would want to ever the whole world to see this? am I acting in a way that I would want someone else to do? Right, the golden rule once so it’s like empathy applied really consistently and broadly. Cuz I’m not gonna say can solve problems, but it’s certainly a useful tool. And so that that, how do we get here? Oh, my God.

Steve Chaparro No. Yeah, this is deeply philosophical, but I think it is a deal, it goes to the inner journey of leaders that are embarking on this, this journey of change and I think these are important things to talk about. Especially the grieving You know, when we say that, you know, when a leader presents a new way of doing things, they in some ways have already processed their own grieving to this new way of doing things. I think that’s important because I think…

Daniel Stillman You’ve already had that they’ve already had an inner conversation. And now they need to design the outer conversation. So that was one of the things that I realized in the book, as I was writing the book was that if this is a conversation, and I can have a conversation with myself, when a team is having a conversation, that’s when I started to say like, oh, wow, organizations are conversations. Not just that they’re like a sum of conversations in itself is like it ebbs and flows. You can go into a into a company and you’re like, this place is humming. You can feel the energy just the way you can feel the energy in the room in a workshop. And so I think an organization or a culture is a conversation. Culture is a conversation that anybody can participate in. Right or real culture.

Have you heard I remember going into a small town in Sweden. On when I was in grad school we did a summer. There was a summer program in Copenhagen. I blue glass for summers, awesome summer. And we went to Sweden and Finland to like, study other, you know, Scandinavian glassblowing style. So we went to this little small town. And there was like a bunch of guys with like, super slicked back and slicked up hair wearing like leather jackets, and they had hot rods. And I was like, why am I walking into the 50s? What is happening here? This was like 2005 and the apparently there’s like, real like 50s muscle car Americana enthusiasts in Sweden. And it’s like, that never died. Or it came back that culture is something you can always participate in.

Have you ever seen the movie ghost dog? Dude, I mean, it’s about like, Forest Whitaker who is amazing, playing a man who is living by the samurai Bushido code, even though he’s like an assassin for like a local mob. How did he decide to enter into authentically? Like you could call it culture theft or whatever. He’s just like, totally legit and himself with the samurai sword. And like living the culture. He’s like, this is the way I live my life, a real culture. I think cultures have a very broad invitation. Like you can be a punk rocker with just a safety pin and a leather jacket. Right and enough hair gel. Nobody can tell you you’re not punk. I mean, punks can tell you you’re not punk. But then you’d be like, screw you. You’re a poser. And so, I think culture like that is the invitation to a culture can be so broad. Anybody can enter into that conversation if they want to. If you want to like live your life. Like Leonardo da Vinci. If you want to relive the Renaissance and be a renaissance man, you can be a renaissance man. I first got this, anybody who’s listened to this, James Carson’s book, finite and infinite games was the first clue I had about this, that cultures a game. And anybody can play it if they want to. Right? You just have to make the rules clear and invite people into it. And often you go into a company, the rules aren’t clear.

Steve Chaparro Yeah. And I think, you know, like, I can think of an example of a design firm that reached out to me, they asked me to help facilitate some conversations around, you know, co creating the culture for their firm. But I really pushed back and said, Well, before I do that at sort of a macro scale within the company, I need to have that conversation with your leadership team. Because what I don’t want to do is open up an opportunity to have a conversation at a macroscale that hasn’t been had at the leadership level, because that you’re right there, there needs to be courage. There’s vulnerability, humility, to have that conversation at an executive level. So that they could in a sense, embody the type of conversation that they are wanting their, their teams to have. And I think that idea of, of facilitation, or these workshops being whether they’re structured or unstructured conversations, it’s still a conversation.

Daniel Stillman And, you know, you could say we’re having a conversation all the time. is the leader showing up? How are they showing up? Right, there’s, we get these signs and signals all the time is FaceTime required is somebody staying late all the time? Like is somebody coming early all the time. We figure out what’s kind of expected of us that it looks bad. If we, if we don’t, if we leave early, it’s frowned upon. We figure these things out and One of the best examples I can think of this is I try to demonstrate this in my own facilitation is leading by example. leaders like to read articles about how to give people feedback. What’s the best way to give somebody feedback, somebody’s really screwing up, and I want to tell them how badly they’re screwing up. But I want to do it in a way that they hear it and fix it. But I don’t have to fire them, because that’s really expensive. Is there an article in HBr that I can read about that? And the answer is, Yes, there is. But they’re not asking for feedback. Right.

So, it’s not a two way conversation. And they want to they wait until things are really bad to do the feedback. Right, and the one on ones that they’re having. I remember somebody who, who I was coaching and they’re like, my leader keeps pushing off our one on ones. We’re supposed to be having these one on ones, and they get rescheduled all the time. Like what does that signal to you? right that’s that’s sending a message. If we’re sending a message, we’re having a conversation. And so if they’re not having that one on one, they’re like, so what do you need? Right? Tell me what’s going on with you. And they’re not saying like, hey, so what do you need from me? What am I not getting from you? How am I? What do you like? What are you seeing in me? If it’s not a 50-50 conversation? What they’re saying is this is a one-way street.

Steve Chaparro Yeah, I think that’s so important conversations definitely are, you know, two way to two way dialogues. And I think, as opposed to just one person saying something, I think that’s so important. What are some other things we’ve covered a lot about conversations? What are some other things that we haven’t discussed that are in your book that people can learn?

Daniel Stillman Oh, wow. I mean. I think one, we talked a little bit about the idea that conversations have size, right? So whether it’s with me or with us, or big us, or between us and them, like conversations have have sides and I think we’ve also talks about this idea that conversations have structure. Right? I think that’s like section three and Section four, just like covered everything. I think the thing that is hardest for me is making time for the conversation with myself. And if I had a gift to give to the world and to myself, it would be the gift of time. Right? The ability to be reflective and to review and reexamine all the best philosophers’ thinkers, strategists will tell you. Bill Gates takes his week. His reading retreats, right.

Ben Franklin had his morning and evening reflections. What good will I do today? What good Have I done today? Allison coward who I had on my podcast was a wonderful facilitator and a wonderful person. Does he has a weekly Sunday date with herself, where she just does an hour of reflection. And she does a Friday morning reading, because she’s like, I my work is my brain. And so I need to give my brain food. And I gotta be honest with you. I starve myself. Right? And so the the last chapter of the book is you are a conversation and my brother, who is a very, very hard to please customer said that that was his favorite chapter. He said that was the best chapter of the book. I was like, does that mean the rest of them sucked? I don’t know. But this idea that you’re a conversation and that we can learn from ourself that we can examine the different parts of our lives.

And I’m sure you’ve done this in an innovation workshop. Where I do teach this I use to teach this to Design Gym. Let’s go out into the world and see how other people are solving this problem. And Jake Knapp’s book design sprint sprint, they talk about lightning talks like how else is this problem being solved? Like, what does this look like in other industries and Let’s steal ideas from other places that’s horizontal. It’s called horizontal evolution happens all the time, where we steal bits and pieces of DNA from other organisms. Our mitochondria inside of us is an entirely other organism with its own DNA that we ate, millions of years ago. True story where aliens were made of like, we’re symbiotes ourselves today. And so this idea that we can have a symbiotic relationship with our own life.

And I started to ask this to myself. intimacy with my fiance, and feeling welcomed and loved is really easy. doing that with my clients is a lot harder. And so I’ve in the last couple of years, I’ve asked myself, How can I be more relational instead of transactional? with my clients? This is a really hard question because It’s the funding I have to what trust that money is just going to rain from the sky or just love the hell out of them. And trust that something will evolve out of it because caring about them as humans and relating to them as humans is important. It’s not an easy thing to do. Because it’s it’s exhausting the amount of presence that we do as part of this job. And so that’s, that’s something that’s in the book, as well as that the conversation with yourself isn’t just having better inner dialogue. It’s, it’s absorbing and listening and having your letting your inner conversations have conversations, letting the conversations in your life talk to each other and say, How can my the love that I have with my, my significant other? How can I take that lesson and bring it outward into my life?

Similarly, one of the guys I coached in design thinking, I’m sure you’ve seen this happen. He’s like, I used the active listening Thing skills you taught us in the research thing with my wife, and it works just like you said, Daniel. And I’m like, yeah, and he’s like, and I use that prioritization matrix. And boy oh boy, is she so happy that like we had the prioritization conversation about our the to do list. That was really great. I haven’t been able to use it at work yet. And I’m like, I’m sure your client, your boss that’s paying for this coaching is really happy that you have a happier home life. I would love for you to also use it with your with your with on your sales calls, pretty pleased. But that’s what I mean about your conversations, having conversations where we use the tools from one place to another work, the skills we have at work, people are doing konban at home now. Right people are using Kanban for their kids for your their chores to do doing and done. Right. You’re having weekly stand ups people have weekly stand ups with their wives now. Right? Some people were like, That’s ridiculous. That’s like, over designing the conversation. Right? And my mother will say, I don’t want to design the conversation all the time, Daniel. I’m like, Mom, that’s a design decision. Under designing it is a choice. And so that’s that’s That to me is like, p thing. Things that people should realize is that you are already designing your conversations.

Steve Chaparro Yeah. My dad used to say not making a decision is the decision to not make a decision.

Daniel Stillman Yep. Your dad’s wise. It’s true. It is a decision. Absolutely fantastic stuff. Dad’s always smart.

Steve Chaparro We’ve been talking to Daniel Stillman, a conversation designer and podcaster at the conversation factory and author of the book, Good Talk – How to Design Conversations That Matter. Daniel, if people want to learn more about you, where can they go?

Daniel Stillman Pretty straightforward. They can go to theconversationfactory.com. It’s a long URL, but it’s all English words. So, it’s easy to spell. Just all no consonants missing no weird vowels missing. Just theconversationfactory.com. And if they want to go to the book, they can, it’s on Amazon, they can pre order it. It might be on sale by the time this comes out. And if they want to download some free chapters, and some worksheets, they can go to the conversation factory comm slash good talk, or they can follow the link on the website.

Steve Chaparro All right, Daniel, thank you very much. Thanks for the conversation.

Daniel Stillman Real pleasure. Thank you.

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