EP 67: Designing Conversation, with Daniel Stillman

Mar 12, 2020

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EP 67: Designing Conversation, with Daniel Stillman

On this episode of THRIVE—sponsored by Workamajig—Kelly and Daniel Stillman, author of Good Talk, discuss the intentional design of conversation. Products and teams are conversations. Even organizations are defined by the conversations they can and can’t have. If “we live our lives one conversation at a time”, what would happen if we designed those from a holistic perspective in order to maximizing human connection?

Episode 67 Links

Daniel Stillman:
Good Talk Book:
iTunes / Apple Podcasts:
YouTube Channel:
Vimeo Channel:


 EP 67:  Designing Conversation

Duration: 26:50


Kelly: So welcome to this week’s episode of Thrive. Today’s conversation is about designing conversation. And I’m here with Daniel Stillman, who is a coach, a consultant, a keynote speaker, and author of the new book, Good Talk: How to Design Conversations that Matter. We were actually introduced by a friend of ours and mutual colleague, Jay Malone of New Haircut, and I’m super excited that he felt compelled enough to connect the two of us. So Daniel, thank you so much for joining me on the show today.

Daniel: Thanks for having me. I expect an excellent conversation since we’ve already had a good conversation before we even hit record.

Kelly: Well, maybe we can start with sort of the backstory of how did good talk come to be, how did it come to fruition? And just would love to hear a little bit more about what either the pain points or the gaps in the market or whatever that story was for you.

Daniel: Yeah. Well, I mean, there’s layers with everything but for me I used to work in industrial design and UX design. And I worked with my clients to try and discover what they needed, what they wanted, what their customers needed and wanted. And we did that thing where you go out, you do the research, you do the insights, and you design workshops to bring them together, you design presentations. And no one really taught me how to do that in design school.

And it wasn’t until many, many years later that I was working as a facilitator teaching facilitation and design thinking with a group in Australia. They call their facilitation practice, conversation design, and I initially thought that that was a super douchey way to describe what I did. I was like, you’re not designers. What does that even mean? But it really put a little bug in my brain because as a designer moving from industrial design to UX design, then I became aware of experience design and service design.

And when you have those new words, you start seeing the world in different way. When you start to see the world as services, you’re like, well, this product is just connected to this big intangible surface service. And so, I was just like, what does it mean to design a conversation? I knew how to design an experience. I knew how to design a service. And so I actually sat down, I did four interviews with four people I knew and respected; Dave Gray, who wrote a book called Gamestorming my friend; Abby Covert, who wrote a book called How to Make Sense of Any Mess, a wonderful book about information architecture. My friend, Leland Maschmeyer, who is now the Chief Creative Officer at Chobani. And my friend, Philip McKenzie, who has a podcast now as well.

And I said to them, I was like, “What does conversation design actually mean to you? Like, what those two words mean?” And they were like, “It’s weird. It’s interesting. It’s intriguing. It means this. It  doesn’t mean that.” It was a provocation. And honestly, I thought, this is weird. And, it took me a year to finally get around to starting a podcast about it. And in a way, like, that’s the origin story for me. And so I started this podcast in 2017 to say like, okay, well, if we can, in fact, design conversations, and it seems that you are like, what are we designing? Like, literally, what’s the material of design? And I don’t know, like two years in, I got tricked into writing a book.

Kelly: That’s a good way to put it.

Daniel: Right, exactly. And so that to me, is the origin stories like one is, the pain point of working in a creative agency and being like, how do I guide this conversation? Like, when you learn about design thinking, like, wow, there’s a structured approach to having this dialogue with my clients. And then when I saw someone else run a workshop, where they physicalized what we thought our ideal experience for this product was using collage, I was like, I can do this. I’m going to tell my boss like for this workshop we have coming up with our clients, like, I’m going to do this word and photo collage thing. And he’s like, what is this? Is it? Is this gonna? That sounds weird? Is it gonna be? And I’m like, it’s gonna be okay. I saw someone else do this. And I could totally get away with this. And it was amazing.

Kelly: Yeah. Sometimes you just have to trust.

Daniel: Yeah. Well, I mean, that’s what he had to do.

Kelly: Right.

Daniel: I had seen it for myself. And we had this conversation where one client was like, “No, I don’t want this product to be magical.” And the other guy, the client, he was like, “This thing should be magical. And so we could have this conversation about, well, what does magical mean?” And that’s to understand what your client means by magical and why one half of the team doesn’t want it and the other half of the team does, like that was a gift — to be able to facilitate that conversation. And so, to me, I don’t think in my bio now I say like Daniel Stillman designs conversations for a living and insists that you do too. And, I think we are all designing conversations as well as we can with whatever tools we’ve been given or stolen or absorbed. It’s like, we remember maybe being taught how to play chess, but very few of us remember being taught how to talk. Right? And so, I think it’s really important.

Kelly: Yeah, that’s a good point.

Daniel: That’s a long origin story. But that’s how I feel about it.

Kelly: No, it’s great. I mean, it gives a lot of context. And I love your mantra, which is like we live our lives one conversation at a time. And what you talk about a lot in the book is the fact that we need this range, right? Like conversations have structures, you just mentioned, and give a good example. But we’re not great at sort of the dichotomy of the structure of those conversations, right? So we can be, as you say, in the book, like forward-thinking or forward and fast or we can be slow and methodical and thoughtful. Why is that so challenging for people?

Daniel: It’s interesting. Maybe it’s a false dichotomy. There’s definitely attention. You know the Rudyard Kipling poem If—? There’s one phrase where he says, if you can talk to crowds and not lose your virtue and talk to Kings and not lose the common touch. There’s this idea of like, can you, in fact, wow a crowd? Can you talk to some to power? Clearly, like, that’s range. I think a lot of people are scraped like you do, you’re a keynote speaker. It’s scary to go up on stage. And it’s a different type of conversation because you can’t see the audience. You don’t get the same…

Kelly: Sometimes those lights are a little blinding.

Daniel: Yeah, those lights are a little blinding. If you’ve ever done a webinar, right? Like you’re talking to the air. And so you don’t get that feedback that you get in a normal dialogue. And I think team dialogues they need to be designed and are usually poorly designed like half of what I think or designers do, that I’ve seen as they just give people better team patterns, team dialogue patterns, making sure that everyone speaks the same amount.

But this thing that you and I were talking about, which is how hard it is to introspect, and to have time with ourselves. I don’t think that’s a modern malady. I think it’s very easy to say, oh, it’s because of phones. But it’s slowing down is hard. And doing inner work is hard. Because we are human doings, not human beings. What we do is we output and there’s this classic Zen concept of the ball being, being but the space in the bowl is nonbeing. And what you actually need is the space in the ball. And so we see what we do, but the nonbeing emptiness silence looks like nothingness. And isn’t valued in the same way because you buy the ball, coz there’s no way to buy space.

Kelly: Right. You buy the container.

Daniel: You buy the container.

Kelly: But by buying it, you’re buying it to fill it up or to do something with it.

Daniel: Yeah. And so like, this is something I talked about with, I think clients are actually buying their time from me. Right?

Kelly: That’s interesting.

Daniel: Like when I am on site, or when they are on a call with us, they are required to set aside their regular everyday lives and to be present, and to put away their phones. They’re like, oh, Kelly’s gonna be here tomorrow. We have to actually get our s*** together, and focus and do real work. And so, I think time is obviously the most precious thing we have and time with yourself is the hardest thing to get.

Kelly: Yeah, yeah. There’s this concept that you also talk about, like the fact that we are constantly designing conversations whether we know it or not.

Daniel: Yeah, yeah.

Kelly: We are clearly not conscious of it. I mean, hopefully this episode will bring consciousness to it. But we’re not conscious of it. But we do it all the time. So you’re asking the question, what would happen if we design these conversations from a holistic perspective, to maximize meaning and connection? So what do you actually mean by that? 

Daniel: Well, so the first thing is, you have a good step back. I’ll break it down for you like a math problem. Maybe, it’s just because I come from a combination of like, I have a degree in physics, and I studied industrial design. And so there’s this idea that if we’re designing, we’re designing something. Like if I want to make a curve more interesting, we spent an entire semester thinking about fast versus slow curves. I’m looking at the painting behind you. And I’m like, looking at those curves and like, oh, I see it, how it speeds up and slows down. And if I wanted to change or critique the physicality of something, I know what to critique. But with conversations, we don’t even know what we’re looking at, because we don’t see the structure. And it’s like trying to play chess without understanding moves. Right? And, modularity of moves.

And so, for me, one of the things I started to realize was that, I wanted to try and give people the smallest number of things to look at when they’re designing a conversation. And one of the most interesting ones is space, and interface, the fact that our conversation happens in a place. Like right now, Zoom is the interface between our conversation, but our conversation is also happening. You’ve got a piece of paper nearby you with a series of questions that you want to try and address. And so, you’re having a constant conversation between your plan and what’s happening. Right? There’s a narrative structure that you have. That’s another thing that conversations are made out of stories. And it’s being held in the space.

And so, one of the stories that I thought was interesting enough to put in the book was the story of this woman who, on NPR, she talked about leaving voice messages to herself. She’d walk her dog, and she would call herself and talk through her problems. And so just literally taking that time is one thing, but then you can listen to them afterwards. And we all know how much it is. We are so much better at solving other people’s problems than our own. Right? And so, what she did was she put her problems on an interface outside of herself, and she could listen to her problems as if it was someone else’s problem.

So she literally like peeled the conversation, her inner conversation out from inside her head, where we think at 4000 words a minute, right? Speech is, I wish I could remember the statistic right now. We can talk much, much more slowly than we can think. Our thoughts are so fast, and so peeling it out, bringing it outside, changing the interface of the conversation immediately makes it easier to address and to process. It slows things down immediately. And so, I think one of the challenges that people don’t even know what they’re designing. And so you can steal patterns, you’re like, okay, let me start leaving voice messages to myself. But to me, I think, understanding the why is more interesting, because there’s another story of like Amanda Palmer, deciding… Do you know Amanda Palmer? She’s super famous TED Talk on the art of asking?

Kelly: I don’t. I’m gonna put that in the show notes though and listen to it afterwards.

Daniel: She’s married to Neil Gaiman, who’s also a badass, and there’s a story of them having a dinner conversation and she’s like, hey, what if we didn’t talk but we just passed notes to each other? And they asked the waiter for a pen and paper, and it was basically texting. But with time to think because writing as an interface for a conversation, it slows things down, and so they would doodle something, she’d write something and slide it across the table. And while he was writing, she got to like enjoy her dinner and just be in her thoughts. And maybe think about what she was saying while he was writing something back. And so this is what I mean by designing conversations. There are ways to slow it down, to speed it up, to physicalize it, to internalize it, to switch it up, and to be playful with the way that we interact. And that will radically change the way that we’re communicating.

Kelly: Yeah, it’s really interesting. As soon as you were telling that story, it made me think of a story. Just recently, I went up to a Buddhist monastery in Pine Bush, New York. And I went with a friend of mine, and in the middle of the day, there was a lunch with the monks that live on, the residents of the campus there. And so the entire time it was a silent lunch, right? So we’re all eating the only thing that you could hear were like the clanking of the utensils and chopsticks and whatnot. And it made me have a conversation with myself while I was eating and I was so purposeful and so intentional. And also really excited that once that silence was broken, I was so clear about some of the questions that I wanted to ask my friend about her experience or ask one of the monks sitting next to me. And it was the slowing down on the silence that allowed me to do that. Really, really interesting. I hadn’t thought about it that way until you just told that story.

Daniel: So good. Great music is not just constant noise at like one volume. There’s musicality to great conversations. And that is what I would call cadence. When does a groove become a rut? You listen to a baseline where it’s like, oh, you know when it’s like it. It pulls you forward and there’s interest. There’s a variety and I think that’s something that we’re missing too. And so just having a pattern of silence and not silence, is essential and loudness and softness and high and low. People don’t know how to vary their voices and speak with a musicality. But we don’t do that for ourselves at all.

Kelly: Well, that was going to be sort of along the lines like my next question was about like, the inner voice work that you do. I think, for me, that’s super fascinating and love to hear a little bit more about that.

Daniel: Well, step 1, if you’ve never listened to Julia Cameron. She wrote The Artists Way and The Artists’ Way at Work. I did a writing workshop with her. I took my mom. It was super fun and when anybody would step up to the microphone with a problem, the first thing Julia Cameron would say is, are you doing your morning pages? And the morning pages are these three pages of free hand, free thinking, just like scraping off the first layer of your brain first thing in the morning? And that is like her base level of like, you must be doing your morning pages. Like that is the fundamental first conversation that happen.

Kelly: Is that like the same thing as journaling or just calling it something different?

Daniel: It might just be fancy journaling. But Julia believes…

Kelly: Fancy journaling.

Daniel: It’s just fancy journaling. The morning pages is not like, oh, this happened. And this happened. It’s literally like, you write it as quickly as possible. It’s free association. It might be a list of song lyrics. It’s sometimes I’ve written a half a page of, I don’t want to be doing this. I don’t want to be doing this. I don’t want to be doing this. I don’t want to be doing this. Whatever it is. So I think journaling is like, oh, so last night, last week, Tom did this and I don’t feel good about that versus like morning pages. It’s just like, I don’t care what’s in it. It doesn’t matter at all.

Kelly: And it doesn’t have to be a narrative. It doesn’t have to be sentences. It’s yeah, okay. Got it. It’s like a brain dump.

Daniel: Brain dump. Exactly. Don’t like barely pick up your pen. Don’t think, just get it out.

Kelly: But handwritten, not typed.

Daniel: Handwritten. It’s absolutely essential. I just got back to my morning pages like a week ago. Because I like to have space. I don’t want to just be, I want to have a flow between doing it, not doing it, but the inner voice stuff, it’s fascinating. There’s a whole school of therapy called Inner Family Systems. There are some Inner Family Systems cards where you look at a grumpy, sullen teen being yelled at by like a mother and there’s a mess everywhere. And there’s a beautiful happy family picture in the back. And it’s like, okay, well, what is the family dynamic in here? And then where’s that dynamic exist in me? But the way that I’ve done inner voice work with my therapist is, whenever I have an internal conflict, it’s actually naming the parts and sometimes physicalizing the parts so that if I have an inner critic, maybe you have an inner critic, too.

Kelly: We all do.

Daniel: Really? It’s not just me? I’m normal? So when I struggle with my inner critic, we name it, we give it a name. And we actually localize it in a room. We put it in a space.

Kelly: Like give it a name, like calling it what it is, or giving it a name like David?

Daniel: Like, yeah, whatever. It could be David or it could be like the taskmaster.

Kelly: So like an archetype. 

Daniel: Well, yeah, well, I mean, I name it for myself and I drew it. I have drawing somewhere where I drew all of the different parts where it’s like, he’s like at a millstone. Like you put an ox around like a millstone, just like push around and grind out that. That’s what I feel sometimes. I find out more stuff. And so you’re like, okay, well, let’s put the taskmaster over there. And what do you want to say to him? What does he want to say to you? What do you need from him? What does he need from you? And that is actually having a conversation with yourself.

And it is much easier when you have somebody coaching you through it. You can also do it for yourself. So when I teach my facilitation masterclass, I do an exercise called the facilitators hats. And people draw the roles that they think they take on as a facilitator, ones that are hard for them to take on, which ones are easier and joyful for them, which ones are sort of like outside of their reach. And then we do some physical sorting where they start to think about like, what’s in the core? What’s in the shadows? What do they want to bring into the center? What’s the pyramid of facilitation for them, and getting introspective about what is the role that I really need to be focusing on right now.

And it’s been really interesting because I made this deck of cards and it was internally very struggling for me because I enjoy people drawing their own. But I decided to just take. I’ve been doing this for like 5 years now. So I went through 5 years of people’s facilitators’ hats, drawings, and just made a deck of like 40 some odd ones that I liked. And the other day, I had them in my pocket because I was going to show somebody a prototype and I was going to this event. And like many people suffer from mild social anxiety.

And I thought to myself, how do I need to show up at this thing? Like, what do I want to be? What’s my goal? Like, what am I going to do here? And I literally pulled out 3 facilitators hats at random, and one was the nourisher. It’s this big top hat where like, the brim of the top hat is filled with food. So that’s something we have to do. When we gather people we have to nourish them. And the other one was the fun hat. Like it’s got a big propeller on it, because sometimes we just need to have fun.

And the other one was a detective hat. And I was like, whoa, I’m going to be the fun nourishing detective tonight. Like I don’t even know what that means. But it was just wonderful provocation for me to think about how to show up playfully and be like, yeah, I know how to pull those parts out of myself. If I’m thinking to myself, Daniel, let’s be nourishing today, I know how to pull out the nourisher in me. And I know how to be a detective, to ask really deep questions.

Kelly: And that’s really interesting because we all have all of these different parts, archetypes, aspects, whatever you want to call them. We can pull from all of these different things. And I like the fact that you pause and you had that moment of reflection of like, what is my intention? Who do I want to show up as in this particular event? And let somebody else decide that, which in this case was the card? Right? Or the set of cards?

Daniel: Right.

Kelly: That’s pretty cool. I think that’s a really, really cool thing that the cards themselves remind me a little bit of… are you familiar with Q&E cards, questions and empathy cards from Michael Ventura that go along with his book Applied Empathy?

Daniel: No, I don’t, but I do know, Michael. 

Kelly: Okay. So he’s been on the podcast, and yeah, so I have actually right behind me a set of those cards. And funny enough, I was having a conversation with a friend of mine over text message this morning. And she was talking about convening and I like pulled the cards out and I was like, oh my God, these questions are great. That’s exactly so applicable. So yeah, it’s really interesting how you can use different cards like that to either ask questions or to sort of, not dictate, but give you some inspiration as to how you want to show up or who you want to be in each given day. Right? And that goes back to your whole thing about like, we are really living our lives and designing these conversations one at a time.

Daniel: They have a choice. It’s to illustrate that we even have choices, is huge. Because most of the time I think we just… respond reflexively, right? So if I’m thinking about how I’m going to show up at this party, I’ll just be like, I’ll just pull it for myself or I’ll make a choice or I’ll be anxious about it. And so giving ourselves the recognition that I’ve got a whole deck of cards of how to be empathetic to somebody. Right? I have an infinity of choices. I don’t think it is scary. I think of it as liberating. Oh, I could show up. And I could be a dick. Like, that’s choice. Right?

Kelly: That is a choice.

Daniel: But some people make that choice without even realizing there are other choices, right?

Kelly: True. It’s just lack of awareness.

Daniel: It’s lack of hard-nosed on purpose. It’s a lack of introspection and time and being like, what do I want? What do I need? Just taking a moment saying like, well, what are my ways? What are my options on the table of showing up and which is the best to actually get me what I want? My fiancée and I talk about this all the time, because we don’t really fight much. Because there’s this idea of like, well, why would I yell at you about the ironing board being out for 3 days? Like that’s not actually going to get me what I want. And honestly, I don’t really care. But the other day, I was like, hey honey, I noticed you took out the ironing board, which we never, it’s not ever really used. I was like, what’s the ironing board doing? And she’s like, oh, like, there’s this thing I pulled out of the back of my closet. I want to iron it. So I thought if I took out the ironing board, it would have encourage me to do it. And I was like, cool. And then like another 3 days later, I was like, hey, so what’s going on with the ironing projects? And she’s like…

Kelly: How’s the ironing project going, honey?

Daniel: Yeah. I know. And she’s like, well, I’m beginning to get started on thinking about doing it. I was like, oh, let’s dig into the process of beginning to get started on doing this. Tell me more about this. And we just laughed hysterically about it.

Kelly: Oh my God.

Daniel: And so then she’s like, the next day she irons the thing and put it away. Because like, that is just such a different way. Now I was able to do that because I love her tremendously. And I find her hilarious and amusing in everything she does. So to me, like I could be like, what’s the goddamn ironing board doing out? And in fact, we sometimes pull up voice out, the old Jewish married couple for fun, and just like we pretend. And I was like, you take out the ironing board and what is it furniture now? It’s gonna be there for how many years? Should I put some flowers on it? What do you think? Right? Because that’s even more ridiculous like yes, let’s just play that role.

Kelly: Oh my God. That is designing a conversation. That’s just designing an amusing fun, amazing conversation.

Daniel: I’m letting out my aggression in a hilarious way, potentially at least to, Janet. And so, that to me is like being thoughtful and playful with how we express ourselves.

Kelly: Oh I love that.

Daniel: Try that on. It’s always fun to be a crotchety old couple. 

Kelly: Okay, I got to practice my Jewish accent though.

Daniel: Yeah, yeah. Just watch The Princess Bride. It always helps. Miracle Max and, and his wife whose name… “I’m not a witch. I’m your wife.”

Kelly: All right. Well, I am going to put links to the book and some of your social channels in the show notes. Daniel, thank you so much for joining me on the show. This has been such a great conversation. I don’t know if I’ve laughed so much on the show before, so I appreciate that.

Daniel: Thank you very much. I appreciate it. It’s been really fun.

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