Daniel Stillman is a conversation designer and coach. He’s the host of The Conversation Factory podcast and author of Good Talk: How to Design Conversations That Matter.

This is a special episode of The Informed Life: it’s the first recorded in person, while Daniel and I attended and taught at UX Lisbon in May of 2022. Fittingly, it’s an experiment: a freeform, less produced conversation about how we converse. In some cases, this results in less context than you may expect. In particular, you’ll hear references to the names of other speakers at the conference. I’ve included links to their profiles in the show notes.

Show notes

Show notes include Amazon affiliate links. We get a small commission for purchases made through these links.

If you're enjoying the show, please rate or review us in Apple's podcast directory:

This episode's transcript was produced by an AI. If you notice any errors, please get in touch.


Jorge: Daniel, welcome to the show.

Daniel: Thanks, Jorge! It changes the vibe when we’re suddenly on.

Jorge: It does! And not only are we on, but this is very special for me because this is the first time I’ve ever done one of these seated across from the person I’m interviewing. We are meeting in person.

Daniel: And this is information.

Jorge: It is information! So welcome.

Daniel: Thanks, Jorge. It’s a real honor to be here. I mean, your talk today was awesome. And you take this topic very seriously. You’re a serious thinker. And so I really respect the opportunity to have a conversation with you.

Jorge: Well, I appreciate that. But we are not here to talk so much about me.

Daniel: Fair.

Jorge: So I have a question for you.

Daniel: Okay.

Jorge: What’s lighting you up these days?

What’s lighting up Daniel

Daniel: Oh yeah. What is lighting me up these days? Honestly, the beach! I discovered last year, with the pandemic, that my wife was able to work remotely, and I convinced her to rent a beach house on the Jersey Shore for a month. We still worked, but we were at the beach, and we could ride our bikes and go for a walk on the beach in the morning, bike along the beach in the evening, and just have a really nice… I kind of want to live on the beach all the time because it’s pretty grim in the wintertime, but it’s… I know that in July we’re doing it again, and that’s something I’m really looking forward to. So honestly, like life stuff… life design lights me up. Actually, being able to make those choices and to have someone in my life to do those things with really lights me up.

Jorge: Well, that’s fantastic…

Daniel: And professionally I’ll say this conference is really great food. Like Scott’s talk about how to win friends and influence people from a UX perspective. Matt’s talk about incompleteness by design. My work is around conversations and designing conversations, and it’s really interesting to see the way it’s looped in the way that it’s manifested in other people’s work, right? So Scott looking at an interface as a conversation and saying, “well, let’s be friendlier.” And so, let’s study friendliness. And Matt talking about incompleteness and cadence, really. Like more rapid turn-taking with shorter turns in the conversation. That’s collaboration. I was like, “oh my God, the one-page, one-hour pledge!” Like, that lit me up! Honestly, I was like, that is designing the conversation around work. And I think they get it. It’s not…. when I wrote my book, I was like, “I don’t know what this is. I don’t think anybody’s going to get it.” And so it’s interesting to see people start to get it. So that is also lighting me up these days on a professional basis.

Jorge: For context, Daniel and I are both attending UX Lisbon. It’s my first in-person conference since the pandemic started. And I don’t know if it’s…

Daniel: Ditto! Ditto. And it’s also the first time… I wrote my book in like 2018-2019. I did similar to you. Like, my podcast was a prototype for what I can learn and understand about what it means to design a conversation. And I started writing it in 2018, 2019. It was published in 2020, [at] some point during the pandemic. Because literally the book was published in Europe, and in April, shipping costs went so high, they decided to put it on a boat. And I don’t know if you remember any of the supply-chain issues that snarled the ports in America. And I said to my publisher, I’m like, “so where’s my book? Like, is it available or is it not?” Like, “when are we publishing?” And they were like, “we don’t know!” And so, this is my first time doing it in person. And it’s my first time doing it with my book. And it’s really interesting because the book is an interface for a conversation! Having it in front of people and then saying, “Hey, turn to page 223 and just like, look at that diagram.” It’s really fun. It’s very different.

Jorge: Well, this feels a little meta, but it’s mostly what I wanted to focus our conversation on is the subject of your book, which is about conversations.

Daniel: It’s very meta.

Jorge: That’s why it is meta, right?

Daniel: Yeah. Conversating about conversations.

Jorge: So the book is called Good talk, right?

Daniel: Yes — which was developed as a result of a conversation. I didn’t know, I… You know, what is the title going to be? I was having a conversation with a woman in a social club that I used to belong to. And, she’s actually pretty… I’m blanking on her name, but she’s fairly famous. Barbara Ehrenreich wrote a book called Nickeled and Dimed. Like, nonfiction journalism in the public interest. And this woman said, “you know, I don’t get paid for this, but I’m really good at naming things. Your book is called Good Talk.” And I was like, “okay!” So that’s a good title! Like, “thank you!”

About conversation

Jorge: So, what is a conversation?

Daniel: Yeah! I mean, what isn’t information, right?

Jorge: Right.

Daniel: We’re chefs, and we see the world as food. So I’ve started to see any iterative communication as a conversation. And I don’t even say that a conversation with a shared goal. Like people would say, “oh, a conversation implies a shared goal and shared interest.” And I’m like, “well, me shoving you out of my way on my way to get on the subway is a conversation between my elbow and your chest.” Because I’m sending information, right? Me yelling at you is a pretty shitty one-way conversation. Designing for maximizing conversation means there are multiple parties, and both parties - or all parties - deserve to be heard.

The thing that surprised me in the research for my book was that we contain multitudes. And we have conversations with ourselves. It’s actually really hard to study sub-lingual speech. It’s very fast. We can talk to ourselves; some people say 400 to 4,000 words per minute. So we’re talking to ourselves a lot and, I don’t know about you, but I’ve got multiple inner stakeholders. Sometimes people call it inner-family systems. Some of my inner stakeholders are really, really lousy to me. And one of the things that people say with dealing with inner speech is, “well, how would you talk to yourself in a friendly way,” right? But I say you sometimes need to really listen to the negative stakeholder. Not just push them away. Like, call them in instead of pushing them away.

Similarly, I started with conversation design as a term that a group of consultants in Australia used to describe their facilitative practice. And I was a little confounded by that idea. I had come out of industrial design school and realized that there was this other thing that was on the ascendancy while industrial design had had its heyday in the 1950s. Nobody told me that in design school! And there was this thing called UX Design. Everything that we’re designing that’s physical has a screen. Hooray! Oh, we should learn about that! And then it was like, “oh, actually, we’re designing services, products, experiences.” So I’d been buffeted around by these emerging trends that helped me think in new ways.

And so, when I met this group in 2015, and they used the term “conversation design,” I actually was like, “what does that mean, to design a conversation?” What are we designing when we design a conversation? And I think I was very much taking it from an industrial design physicist — which is my first degree — perspective of like, “what are we designing when we say we design it?” We are designing information, right? And we’re architecting information. Like, what are the mutually exclusive and collectively exhaustive things that we could say we are shifting?

And I actually did four interviews. I did four test interviews in January of 2016. Like right after I’d done this work with this group because it lit me up. I interviewed Abby, Abby Covert, Dave Gray, and my friend Philip McKenzie, who is a cultural strategist. And my friend Leland Maschmeyer who used to be head of The Collins Group and for a time was the chief creative officer at Chobani. So, Dave Gray doesn’t need an introduction, but he co-wrote Gamestorming for people who don’t know. And I just said to them, like, “what does conversation design mean to you?” Like that was the question. Like, I think this is interesting. I wanted to have a thing. I wanted to have a thing that was mine. And I was like, “is this a thing?” And Abby was one of the people who said, “well, yeah! But be careful of manipulation, right?

So, what is a conversation? Like, if you and I are talking and I’m using all these Dale Carnegie techniques to make you like me - and that’s what Scott was saying - it’s like, well, is it really an authentic conversation if I’m trying to smile and remember your name and be sincere? Like, I’m using techniques on you. Is it still a conversation? Like sure! I’m just trying a little harder, right? Anyway! That’s a very, very long answer to your simple question of what is the conversation. But I see a spectrum of like, one to one, me to me, many to many, one to many, many to one… those are all conversations.

Jorge: An insight I got from your book was that… I guess I had come into it assuming that conversation is something that happens between two or more individuals.

Daniel: Yeah.

Jorge: But there is such a thing as an internal dialogue that’s happening.

Daniel: Yes! And I think nine times out of nine when I’m coaching someone, it’s the inner conversation. Like, in negotiation theory — and I highly recommend, I went to the Harvard… I love that I can put Harvard on my LinkedIn profile — I went to the Harvard Negotiation Institute. Leland recommended it to me in my podcast interview with him. He was like, “it’s easily the most bang for your buck. It’s like you will definitely make that money back in whatever negotiation you do in the future. And it’s called Aspiration Value And Getting To Yes, in Negotiation Theory at Harvard. Your aspiration value is, what do you aspire to? Your aspiration value is a negotiation you’ve had with yourself.

Some of the gap between men and women in remuneration can be attributed to: for some reason, men are more willing to ask than women. And so just the willingness to ask. If you run the game simulation over and over again, if more men are asking more often within their careers than women are, the gap just gets larger and larger and larger, which is kind of shocking. So I interviewed… oh my God, I’m blanking on her name. That’s terrible! She has a company called Ladies Get Paid, which is about just teaching women negotiation. She’s like, “let’s just make it really accessible and low cost so that every woman knows it’s okay to ask, regardless of whatever cultural training we have.”

And that’s a conversation that we’re having with ourselves! Asking is bossy or bitchy or brash. And that’s a conversation. And I think there are fears of conversation because the conversation I’m having with myself is part of this larger cultural conversation of like, what do we do around here? And these are maybe in inner voices that we have, but yesterday in my workshop, there was a woman from Norway who was like, “I don’t know if we can really… you know, we’re not so straightforward! Like I can’t ask these high-intensity questions you’re asking me to do.” I’m like, “really? What will happen if you do?” And she’s like, “I don’t know!”

Jorge: Cultural differences.

Daniel: Yeah. Do they exist? We believe they exist, and that’s a bigger conversation. Like, well, “what do I believe I’m allowed to do?”

Jorge: But I get the sense that just the awareness, right? Because we… And again, I’m going to expose a lot of the assumptions that I brought into the experience of reading your book…

Daniel: I love it.

Jorge: … that conversations are something that we have — and we’ve been having since we were little children. So we’re not as thoughtful about how we interact with each other through language, right? We kind of do it. We just kind of go into it.

Daniel: Yeah!

Jorge: And this is the big insight that I got from your book, which is that we can design for conversation, right? In the sense that…

Daniel: Yeah.

Jorge: … like you can’t really design an experience, but you can design to enable certain experiences to happen, right?

Daniel: Yes.

Jorge: And I got the sense from your book that there is kind of an architecture to enable good conversations.

Daniel: Yes.

Jorge: And you talk about an operating system for conversations. And I was hoping that you would tell us a bit about that?

The conversation operating system

Daniel: Happily! So, the conversation operating system came out of two things. One, Aaron Dignan wrote a book called, Brave New Work. And I met Aaron when he was at another company several years earlier. Actually, at my first and only time at South by Southwest. You know, in the interest of extolling the virtues of my amazing biography, my first business was a 3D-printed men’s accessories line that… I think you might know my friend Carl Collins and Peter Nakey.

Jorge: I do know Carl.

Daniel: Yeah! So we started this 3D-printed men’s accessories company. And at the time 2012, 2013, 3D printing was like on the ascendancy. We kind of went a little viral because of Swissmiss, who we were talking about earlier. She posted these bicycle cufflinks we made. And I wound up speaking on a panel about 3D printing. Super random. But anyway, so Aaron’s work I followed for years. And they had this OS. It was about like, what’s your company’s operating system?

And I think that started my thinking of like, “well, yeah! Like, it is nice to be able to show someone the one pager, the canvas.” And you know, I’ve been teaching facilitation and group dynamic stuff for years. And I think doing it through a pretty mechanical lens, successfully — like, helping people to write stuff down before they get in groups; pair up before you get into groups. Like, really basic things. They’re mechanical moves. But when I started doing my research on conversation design, I realized that turn-taking is part of conversation theory. So when I started looking at all the conversation theory material, I was like, “there’s a lot here, and it’s not digestible or clear!” Like, what does it mean?

And so, in my facilitation workshops, I was trying to show people like… just a grid. I was like, “okay, well, Aaron’s got a grid of nine things like time, space, you know, pace. What are the things that I think I can actually shift?” I was just trying to get people to see them the way I saw them and trying to make it as simple and clear to myself so that I could make it as simple and clear to others.

I have pictures from workshops I did in 2018 where my version of the OS was probably like six things or four things that I thought were the easiest to grasp. Like, the clearest. And so, slowly, more things were added. And I interviewed Daniel Mezick, who talks about using open space technology meetings to try and get organizations to be more agile. And he was the one who put “invitation” into my operating system. For a while, it was in the center of my OS canvas because I was like, the invitation is what drives a whole conversation. “Hey, can we talk? Or, “get outta my way.” Right? Is it an inviting invitation? And then, over time, I knew that space as the interface for the conversation was very important.

And just from a, like, a physics perspective? I put that in the center of the OS because I was like, really, the space, the place, the interface for the conversation is where all of the other elements come into play. And so obviously, without people, there is no conversation, right? It can be one person. It can be many people. We just got to know who.

Jorge: It’s like the list of participants.

Daniel: The list of participants — and I think sometimes when I teach about it, it’s also who isn’t included. Who are the ghosts in the room, right? When we say the user, we’re trying to bring the user into the room, even if they’re not in the room, right? Are we doing co-creation? Are we doing participatory design, or are we doing a telephone tag design, right? And so, I mean, I suppose I could have made a… like, Aaron did go from nine elements to 12 elements when he finally wrote his book. I just think it’s an ugly rectangle, you know? I was like, “I’m going to keep it at nine!”

Jorge: Yeah, and there comes a point where it becomes too many to keep in mind, right?

Daniel: Yes. Nine’s still a lot! When I was shopping my book around to friends and getting them to give feedback, they’re like, “nine things. It’s a lot of things. It’s too much information!” Right? It’s five plus or minus two, right?

The nine elements of conversation design

Jorge: Well, and for folks who might not have seen it, it is a three-by-three matrix, right?

Daniel: Yeah.

Jorge: And each one contains one of these elements.

Daniel: Yeah, each of them is like to me a brainstorming prompt for: am I thinking about the total design of this conversation? The people involved, what are the power dynamics? What’s the invitation that initiates it? Turn-taking and cadence. My publisher fought against turn-taking and cadence being two things. And I just decided not to convince him and said, “I’m not changing it.” Turn-taking is “you speak-I speak.” And how we rule… what rules the turn-taking in group mechanics — group mechanics turn-taking is easily the most powerful shift you can make. Cadence to me is like, nobody has a conversation thermometer, but we all know if a conversation is getting hot or cold. And I think there’s also the sense of like the musicality of a conversation. So, it’s like the patterns between conversations. Like, you call your mother every Friday. We have a weekly standup. We’re going to do a full-day workshop every other Wednesday for three months. That’s a tempo.

Jorge: I also got the sense that cadence has to do with how frequently we do this, right?

Daniel: Yes.

Jorge: And I get the sense that it’s… not all of them are relevant to all conversations, right? Like, for example, this conversation… I’m going to go meta here. But this conversation that we’re having is not part of a regular series, right? It’s…

Daniel: But it is for you.

It is. But you and I have talked a few times over the last few days — but not in this setting. And I’m just thinking of… as you’re listing them, I’m thinking about how, this being the first of these conversations that I do in person, and I’m doing it away from my studio, away from where I regularly do this, right? So, there’s the place thing. We’ve had to look for a quiet place in the bustle of the conference, right? And this notion of the turn-taking is something that’s very interesting because when you’re doing this over Zoom… we’ve learned over the last two years — we’ve been conditioned to learn — to pay attention to facial expressions if the person has the camera on, but also to audio cues in a way that is less rich than what we’re doing now. Like, I’m looking at your whole body language here. Yes.

Jorge: It’s a very apt subject to be talking about in having an in-person conversation like this in a setting that is not your, or my, usual environs, right?

Daniel: Yeah, totally.

Jorge: So, I think that over the last couple of days that we arranged this, we’ve kind of collaboratively designed this conversation, right?

The story of a conversation

Daniel: Yeah. Had some pre-conversations. And that goes to… yeah! That’s the cadence. I think the third element of the conversation operating system that my publisher wanted to collapse into one was narrative. So the… I was trying to digest again conversation theory, threading; I felt very poorly defined in the research that I had read. But we know what the thread of the conversation is. And there’s some wonderful poems about like… I’m forgetting the name of the poet. But he’s like, there’s a thread that you hold onto. As long as you hold it, you don’t get lost. And we all know that we’ve talked about the red thread of a presentation or the golden thread of a presentation. Losing the thread, picking up the thread.

I remember a couple of years ago, visiting an old friend who I hadn’t seen since Junior High School. And somehow, we reconnected. I was in Philadelphia. And you just pick up exactly where… The thread is a rope. You know? You’re just right back there versus a very tenuous thread that breaks very easily. And so I think… I’m a little messy. I could probably use more information architecture in the book and also a better understanding of conversations. Some of the chapters were very hard for me to write, Jorge.

I don’t know what it’s like for you, but writing about power. I was like, I know very little about what it means to, you know… as a white man. Like what does it truly mean to be powerless? I also, as a Jewish man, I don’t… sometimes I don’t feel like I know what it means to be truly powerful. When I was writing about narrative and threading… Like, I just love narrative. I think narrative is what holds everything together. It’s easily… the binding force of the universe is what’s happening. The story of a conversation is what we both remember. That’s the thread. But the thread is also like, is what is happening in the conversation coherent?

In the book, I talk about my friend Darcy, who’s an extremely discursive conversationalist. And you know that there’s some people who are like this. So, this is what I mean when I say a conversation operating system. We have preferences. We have habits. We have levels of comfort. I love going on the wild ride with Darcy. And there’s some people who… it gives them palpitations. And I just like the idea of being an all-rounder, having more flexibility. And also, the question: is the way that I am designing my conversations getting me what I want out of life? Is it working for me? If so, great. Don’t read any books about it, right? If it isn’t, then the question is, “what do I think I am capable of shifting to make them better?” And I think that’s the problem if you’re going to be a reflective practitioner. And I loved that Abby left a very nice blurb for my book. She said, “if you think that you just know, as we all know, how to be great conversationalists, then you are under a very false assumption, and you should read Daniel’s book.” I was very grateful for that.

If you want to be a reflective practitioner of information architecture, you read your books; you read Abby’s books. You read Saul Wurman. If you want to be a reflective practitioner of UX, you should go to UX conferences. And if you actually believe that communication is iterative and not just like, “I’m a good communicator, but I know how to adapt and listen and absorb what you’re saying and then recommunicate with you and then accomplish something with you.” if you think that that’s actually a core skill in life, then you should study it! If you’re serious about getting what you want out of life and not everyone is, which is totally cool. I would love to just, you know, crack open a beer at the end of the day and not think about half the things that I think about.

Jorge: Well, that’s a Dunning-Kruger thing, where people think that they’re… how does it go? It’s… if you don’t have enough competence to know that you don’t have the competence, right?

Daniel: And negotiation is a perfect example of like, people just have… there’s default haggling… we’ve watched our dad do it, or our mom, and that’s how we learned how to talk. And it’s actually inefficient. It doesn’t lead to good outcomes. And so there are better ways to do it. Certainly, most meetings suck. At least if you look at the data.

Jorge: And when you were talking about Abby’s blurb for your book and all that, I was thinking back to the beginning of our conversation when we were talking about this idea that conversation is something that we’ve been doing since a very early age, and therefore we are not reflective about it. We just kind of barge into it, and not all conversations are the same. Some conversations can have a very serious repercussion in your life, right?

Daniel: Yes! Will you marry me? You’re fired. Right? Like these are…

Jorge: They represent inflection points of some sort in your life. Others are more mundane. My sense from reading your book is that we could all do better to at least develop the awareness that there are factors that are conducive to better outcomes for conversations than others.

Factors for better conversational outcomes

Daniel: Yes. So, there’s something that comes up to mind: if you watch movies or like any kind of TV drama, the music tells you if it’s an important moment. The music tightens, and you tighten up; you’re like, “this is an important moment! Something’s going to happen.” And that is not present in life. It’s up to us to decide whether or not a moment is important and if we’re going to take advantage of that moment or let it, as they say, slip through our fingers. Something I often do in my workshops — and I do in person and online — is, when I send a group of people out into a breakout room, I just say, when they come back, just drop in the chat, three words that describe what that conversation was like. They’re like, “just words?” Like, yeah! I just want to know what it was like. I don’t want to know what you talked about. I want to know what it was like and like…

Jorge: The experience of having the conversation. So, not the content, but meta, again.

Daniel: Exactly. Like stepping back. How did you feel? How do you feel now? How would you describe your experience with the conversation? Maybe that’s a better prompt. Thank you! And they say, “oh, it was fun. It was engaging.” Or, “oh, it was hard. It was confusing. I felt we ran out of time.” Like, “ I’m feeling like my brain is bursting!” And I’m like, that’s four words. And then everyone laughs, you know? Humor is part of my conversation operating system, right? It’s the Woody Allen effect, right? Self-deprecating humor. I learned it from my dad. He would do this thing where he would yell at my brother and I, if we’d done something wrong but make a joke about himself or something else and make us laugh while we were being berated and punished. It was really confusing.

That was his conversation operating system. So, to be able to describe the quality of the conversation, I learned this from a coach of mine. He describes leadership as the ability to describe with specificity a quality in another. This is an important skill because as a leader, to be able to say, “Jorge, you did a great job. Thanks. I really, really loved those three slides. You really set it up, and then you landed it. And I saw the room. They got it.” And you feel that differently.

Jorge: Specific feedback.

Daniel: The specificity. And to be able to say so in the workshops I ran over the last couple of days on powerful questions, I shared four words that aren’t in my book because maybe over the last two years, as I have thought about what it means to ask more powerful questions in my coaching practice, I learned the word “spaciousness” from my friend Ellen. She… the idea of not open versus closed, but spacious. How spacious is my question?

Jorge: Spacious, as in it gives me leeway to answer.

Daniel: Yeah. You know, in design thinking, we used to talk about like a good… how might we? And like, is it in the weeds? Is it in space?

Jorge: How is a spacious question different from an open-ended question?

Daniel: I think open-ended… well, so it might not be! But I think the word is evocative, right? And so this is what I mean: everyone gets to choose their heuristic for what they decide they want to judge a good conversation on. So, if they say, “that was a very efficient, effective, taut meeting. High-fives all around, everyone! Good job. That was a 15-minute standup. Pow! We did it!” Versus like, “that was a very, very deep, slowed-down, grounded and impactful gathering everyone. I’m really glad we carved out time in our schedule for that.”

Spaciousness, to me, is a polemical word. You say like, oh, that is a very spacious question. That’s a big question! I don’t know if I can answer that question. It’s really spinning me for a loop. What’s lighting you up these days? It’s a pretty spacious question, right? How do you fill your days? What did you do on Monday morning at 9:00 AM, right? If you really want to know what my life is like, right? That’s a closed-ended question. And so I think there’s this tyranny of like open versus closed versus like the spectrum of spaciousness. Very, very spacious to a pinhole through which we look at the world, but it’s a lens.

So I’m into spaciousness. I got that where I’m like, “oh, spacious is great!” And I want people to break open versus closed. Because they think open is good and closed is bad. It’s not! Closed questions can be great! Do you like eggs? Are you allergic to eggs, Jorge? Like I’m making you breakfast, and I want to know! Are you allergic to eggs?

Jorge: For the record, no.

Daniel: Yeah, this is important. I don’t want to kill you.

Jorge: Well, but to your point, it seems like the type of questions you ask are completely dependent on the context and objectives of the conversation, right? Like, I wouldn’t expect that the question about the eggs is relevant if you’re making breakfast. You don’t want to engage in a heartfelt, coming together of two minds or whatever over my egg allergies.

Daniel: Maybe if we’re doing menu planning, I’d be like, “Jorge, what kind of breakfast did your mom cook for you as a child?”

Jorge: Right.

Daniel: I want to know what kind of breakfast are going to be most evocative of…

Jorge: To evoke some kind of childhood memory.

Daniel: Yeah. Because I’m having you over to my house for Sunday brunch, and I want you to weep, I want you to have a Proustian madeleine moment and be like, “I haven’t…” Like at the end of Ratatouille, when he eats the ratatouille, he’s like, “Oh Mother of Ratatouille! I’ve not had this since I was a child.” That’s what I mean. It’s like raising the stakes. So, I also talked about intensity in the workshop. Like, I don’t know. I could have had intensity as an element of the conversation operating system. I didn’t. It wasn’t on my radar for some reason. Is it a fundamental? I think what I was trying to find was like the hunkiest, chunkiest, like Katie’s talk. The red buttons of like… my understanding of conversations has maybe become more nuanced and you know, another one of the workshop was orientation. Am I asking about myself, do I push the conversation towards…? We all know people who push the conversation back towards them all the time. Or am I asking about the future or the past or the present? That’s another way to orient the conversation. It’s very powerful to ask questions about how did this happen? How? How did this happen? Okay, well then, how are we going to fix it? Those are very conventional ways of thinking about things.

Pre-mortems are very different. Speaking from the future to say, “we did a great job. How did we do it?” The magic wand question, which I got from Andy Polaine, “okay, you want it? Magic wand! It’s yours! Now, what do we do? What would you want next?” Like, let’s take that leap. Let’s take two leaps into the future. Those are manipulating our orientation and what we’re looking at with time. So, I think in conversation, it’s our… you know, we’re co-designing it, but like, maybe I want to talk about what’s present. And this happens in couples all the time, right? There’s a moment in time where something is broken, and somebody wants to say, “well, I won’t do it again.” Or, “you always do this.” Right? And we’re speaking at cross purposes. Like, somebody’s looking toward the past, somebody’s looking towards the future, and somebody’s just saying, “can we just clean up the milk?” Driving our attention. We are all paying attention to different components of conversations because we all have our own goals.

Jorge: So, with regard to goals, I wanted to ask you about that because I think that in the realm of conversations, it’s one of these things where there might be… Well, I’ll talk about myself. I often find myself in situations where we are having a conversation that has some kind of explicit purpose, right?

It might be a kickoff. This week, I was part of a meeting that was a kickoff meeting for a new project. And we’re meeting because we are undertaking a new project and there’s a list of people who have been invited to be part of this. We’ve chosen the place, the medium through which it’s happening. All of the components of the OS. And we have this explicit goal to get the ball rolling on this project, right? That is the explicit objective of this conversation.

In conversations, I find that there’s often implicit objectives, right? So in a case like this one, part of the implicit objective would be something like… we’ve never worked together, at least some of the people in the call. And, if this is to be successful, we have to start gelling as a team, somehow. And there’s all this interpersonal human dynamic stuff that is happening.

I’m wondering to what degree or if there are components of the operating system that operate more at that level or that we can more explicitly point in the direction of this unspoken stuff, right? Like, “someone has to pick up the milk” is a very pragmatic conversation that needs to happen. If it’s happening in the context of a marriage, that’s a much broader conversation that spans a lifetime.

Daniel: Yes, if we’re lucky.

Jorge: And you don’t want to have the “pick up the milk conversation” in a way that would set that relationship back in some ways, you know?

The human dynamic of conversation

Daniel: Yes! It’s interesting. So it’s making me realize, and I’m… I always get frustrated when I interview somebody for my podcast and we cover like they’re like, “so there’s six elements of what it means to be blank!” And we cover like the first three, and then somehow we never get to the last three. So, I’ll just say we’re touching on the last two elements of the conversation operating system. If I can visualize my own OS properly, we talked about people and power, right? Invitation. The interface. Turn-taking and cadence. Narrative/threading. And now we’re talking about error and repair and goals.

So, error and repair I put is one thing, because it’s like… I see them as like a loop. And goals. Like, what are we here to do? Are we goal-oriented? Can we… as Natalie said, “are we okay with wondering and wandering?” Can we be low goal-oriented? So, I think there’s probably a two-by-two for each one of these elements. It’s like high-goal orientation versus low-goal orientation. My goals, your goals, or our goals, if we were to orient that way.

And with error and repair… if we’re talking about a team and teaming, getting a sense of like, if you and I talk at the same time, it’s the easiest error to see in a conversation, right? We talk at the same time; we literally collide. And then one of us — both of us — will try to be polite. “No! Oh no, no, you go!” And one of us will yield a turn, and the conversation will continue. That’s an easy repair for an easy error. It’s very obvious. Most errors in conversations are assumptions. Like, “why didn’t you fill out that form?” “I thought you were going to pick up the milk,” right? And that’s because goals and what constitutes an error is not made explicit.

And so, this is what team charters are all about. Or making a user manual, which is a great thing for any leader to do with their teams. To say like, “here’s how I like to work.” One hour, one page, right? Don’t call me on weekends. I prefer texts over emails. I love Google calendar and Excel. Don’t give me a Word document. Keep it at a PowerPoint. And if you send me a PowerPoint, I will flip over the table. Versus my wife and I, we like to keep the conversation at this level. Some people have… they see an error, and they don’t want to repair it. Or they see an error, and they say, “Hey, that’s not working for me” or, “it sounds like you did this.” Like, “I felt that when you did that. Is that what you meant?” “Oh, no, I’m sorry!” “Oh, great. Cool.”

So, repair. And I think teams have to have that conversation about what constitutes an error because otherwise, we’re using a jump. I jumped to conclusions-mat as the, you know, the “Office Space” reference. One of my favorite “Office Space” references. But goals are like, “what was your real question?” — it’s like, what do we want? What’s explicit versus what’s implicit. These are… man! This is the negotiation dilemma, right? If I tell you everything I want, will you use it against me? Will I get everything I want? And that is about building trust, which is a thing, right?

Jorge: Right. And it’s different in the context of a marriage where ostensibly your goals are aligned, right?

Daniel: Yes.

Jorge: As opposed to, I don’t know, you’re trying to buy a house or something where that’s a more explicit negotiation, where the two parties are maybe in tension; the goals are kind of in tension, right?

Daniel: Yes.

Jorge: So, I think that that’s a pretty good overview…

Daniel: We covered everything!

Jorge: Most of the points. I’m wondering if we might leave folks with one suggestion on how they might be more mindful about conversations. I’m not going to ask how they can have better conversations, but how can you become more aware of the conversations you’re having and the impact they’re having.

Conversational awareness

Daniel: I am a deep, deep lover of visual thinking, right? And I think you talked about this. We use tools; we shape our tools, and our tools shape us. And drawing is the best way, I think, to visualize — concretize — what it is we expect to happen. And the arc of a conversation is something that we talk about, but I don’t think we ever draw. And this is an experience map, right? It’s just literally just like using the tools of experience design. Well, we design services, and we have service maps. We design user experiences, and we have a user experience arc. Let’s design the arc of a conversation! I mean, like, I probably have one here! Like, this is what I draw when I make a workshop, right? I, I draw the big arc and then the little arcs, and I try to nest them all together and get a sense of, like, where do I want things to be at the end? The beginning is the invitation; the end is hopefully a shared goal. What connects them is the thread. The story of what’s going to happen.

Jorge: Well, the listeners can’t see it, but It’s a sketch. It’s a hand-drawn sketch that…. and I obviously haven’t read it because it’s the first time I’ve seen it, but I’m seeing curves that hint at there being some kind of arc between certain milestones. And then there’s a long series of very short ones. And then there’s a few that span across three of them at a time. And then there’s one big arc that spans across six of them. What that sketch communicates to me is awareness of nested cadences of different beats, maybe?

Daniel: Yeah!

Jorge: As a way to talk about it…

Daniel: And so, the simplest way I draw it in some of my talks… oh man! My brain. There’s a Jewish philosopher who said, “all real living is meeting.” And so the I-N-G of meeting… like a real meeting, is invitation, narrative, and goals. What is the invitation that is going to bring someone to the table deeply? Like, to deeply participate. I think the way Scott brought it in from Dale Carnegie is genuinely arousing them in eager want. I love that phrase. Invitation is about arousing in someone else an eager want. Like what is going to get someone to come to the table with their whole self? That’s the dream, right? As opposed to emotional blackmail or economic force, right? Which are all extrinsic motivators versus intrinsic motivators. The narrative is like, “ I’d like you to come to this meeting so that we can blank in order to blank.” And the goal is like, hopefully like Viktor Frankel Frankel says, “a man with a why will endure any how.” Right? If we really have a shared why… as many “why’s” as we have to. Five to nine, depending on what school of philosophy you come from. Liberating structures as nine why’s because five why’s is not enough! Why do we really want what we want? Like, what is our real shared goal? This is what I sketch out to say, like, “what’s the plan? What’s my plan?”

Jorge: So, I’ll tell you what I’m taking away from this is: whenever I am either invited to or inviting people into a conversation, I’ll be more aware of the invitation. How the invitation happens, the narrative that underlies it, and the goal which might be unstated, right? Like, maybe making it explicit is part of…

Daniel: Yeah. There could also be the overt versus the covert goals, right? And there’s also the heuristics. Like Bern, who’s one of the other speakers here, she went through my workshop and is a great workshopper. She was like, “you had us up! You used all the walls! We were talking to each other a lot!” And my assumption is people get more joy, energy, and value through conversation and connection then they do for me kicking through a bunch of slides, right? That’s my conversation operating system. And so, I design for maximum conversational density. I don’t think everyone spoke to everyone in that room, but I had individual thinking, a breakout of about four or five. They did two paired exercises and then a third paired exercise. And that’s on in the first half! So, they would’ve talked to 4, 5, 6 other people in the room. And in the afternoon, we did another three-person breakout and two paired instances. So, they didn’t talk to everybody in the room, but I want them to meet people and to learn through dialogue. Because that’s what I like!

I’m designing for what I think people want and like and enjoy. And that’s being an intentional designer of, “what would you think they would say it was like?” Was it deep? Was it cool? Was it fun? Was it fast? Was it impressive? Was it stultifying?” Nobody says that! Nobody says like, “you know what I want? I want people to be bored out of their minds, so I’m going to ram a hundred slides down their throat and have no exercises.” I’m like, how’s that a workshop? Right? So I design for a conversation. But I think Matt’s thing is like, my invitation is purposefully incomplete. My goal is to get as much information from you as possible. And the story is: your feedback will help me move forward, right? He’s not using these words, but in mine? That’s how I would look at being super intentional about the invitation. Your story and their story and what you both really want out of the thing.

Jorge: Well, I hate to wind down this conversation because I’m enjoying it so much!

Daniel: Me too! Time goes fast.

Jorge: Yes. But, alas, we have to…

Daniel: Nobody wants to listen to a two-hour conversation.

Jorge: Well, it depends, right? It depends! Maybe they don’t want to listen to us talk for two hours!

Daniel: No, no! I’m not that famous. If you were Joe Rogan and I was, you know, some other terrible person, they would totally listen to it. But not your audience. Your listeners want something different than his listeners, I think.

Jorge: Where can folks follow up to learn more about your conversations?


Daniel: Well, you know, the name of the website was a tongue-in-cheek joke that has stuck with me for years. It’s called The Conversation Factory. They can also find me at danielstillman.com. Those are the two things. I do a facilitation masterclass, and I host a community of practice for people who want to become better facilitative leaders. And they can learn about that at theconversationfactory.com. And they can also get free chapters of the book, Good Talk! Available wherever fine books are sold.

Jorge: Is there a diagram of the OS, the matrix?

Daniel: Yeah, there’s a whole series of diagrams. I don’t expect everyone to buy both the audiobook and the Kindle. And so, there’s a lot of drawings in the book. Some of them more helpful than others. All of them, I think cute because I drew them! So, you can download all the diagrams from the book, including the Conversation Operating System. But you have all nine elements in your head now.

Jorge: Great. Well, I’m going to include links to your site, but I’m especially going to include a link to the diagram because we’ve been talking about it, and people might be wondering. Thank you so much for joining me on the show.

Daniel: Thank you for having me. I think this is really important stuff.

Jorge: Absolutely.

Daniel: And what I say in my workshops is, good design is invisible, right?

Jorge: Yep.

Daniel: In some ways! And this is especially invisible because we think it’s so reflexive and there’s so many habitual choices that we’re working with. So, the work that people do to improve the world through being more intentional about their conversations is very important work. And so, all of you listening in podcast-land, I honor you for the work you do to improve the world by improving the way we talk. Because it’s really important.

Jorge: Absolutely. Well, check out Daniel’s work. Thank you, Daniel!

Daniel: Thank you, Jorge. It’s a real pleasure.