in: People, Podcast, Social Skills

• Last updated: October 1, 2021

Podcast #634: How to Design Conversations That Matter

We typically don’t think much about how we structure a conversation. We just sort of wing it and hope for the best. But my guest today argues that all conversations — even the small and mundane — can impact our ability to lead, influence, and connect, and ought to be approached with thoughtfulness and intention. 

His name is Daniel Stillman, he’s a consultant, author, and podcaster, and in his book Good Talk: How to Design Conversations That Matter, he draws on his background in design to show how we can use the principles of design thinking to improve the quality of our exchanges. Daniel and I kick off our discussion by unpacking the defaults of conversation people often fall back on. Daniel compares the structure of conversation to an operating system, and we turn to how we can improve this conversational OS, beginning with the way we invite people into a conversation with us, and why we shouldn’t just ask, “Can we talk?” We then get into how we can improve the “interface” of our conversations, by recognizing the influence that space and place have on them, and choosing the right environment for a particular dialogue. We end our conversation with the options you have for responding when it’s your turn to talk and how to deal with the gaffes we all make during conversations, and the feelings of regret that frequently follow.

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Show Highlights

  • The conversational defaults that may not be working for people
  • What to do if you’re the “fixer” type of conversationalist 
  • How to approach a hard conversation 
  • Making an honest invite to a conversation 
  • The ways we teach people to treat us 
  • How the space and the place affects our conversations 
  • The need to sometimes re-invite someone into a conversation 
  • How to elicit more from the people we’re conversing with 
  • Why you don’t need to have a hot take on everything 

Resources/People/Articles Mentioned in Podcast

Hand book for planing a conversation.

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Daniel on Twitter

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Read the Transcript

Brett McKay: Brett McKay here, and welcome to another edition of The Art of Manliness Podcast. We typically don’t think much about how we structure a conversation, we just sorta wing it and hope for the best. My guest today argues that all conversations, even the small and mundane, can impact our ability to lead, influence, and connect, and ought to be approached with thoughtfulness and intention. His name is Daniel Stillman, he’s a consultant, author, and podcaster, and in his book “Good Talk: How to Design Conversations That Matter,” he draws on his background of design to show how we can use the principles of design thinking to improve the quality of our exchanges.

Daniel and I kick off our discussion by unpacking the defaults of conversation people often fall back on, and then Daniel compares the structure of conversation to an operating system, and we turn to how we can improve this conversational OS, beginning with the way we invite people into a conversation with us and why we shouldn’t just ask, “Hey, can we talk?” We then get into how we can improve the interface of our conversations by recognizing the influence that space and place have on them and choosing the right environment for a particular dialogue, and we end our conversation with the options you have for responding when it’s your turn to talk and how to deal with the gaffes we all make during conversations and the feelings of regret that frequently follow. After the show is over, check out our show notes at

right, Daniel Stillman, welcome to the show.

Daniel Stillman: Thanks for having me, Brett. I’m stoked, really.

Brett McKay: So you’re a designer who went to industrial school, and now you help people and companies apply the principles of design thinking that can be used to design products, to even designing better conversations. And one of the first thing that design thinkers do is figure out the default ways humans use a product, a service, a system. Let’s apply this to conversations. What are some of the defaults of conversation that may not be working for people?

Daniel Stillman: Yeah, so first of all, I struggled with this in writing my book, ’cause I really want people to be reflective practitioners of their conversations, ’cause most of us can’t remember learning how to talk. You might remember learning how to play chess, and maybe you got better at it, you learned some strategies. I think most of us are working with a patched-together system, like we’re magpies, we just… We saw something that we thought worked, and so we copied that and maybe it worked for us. And so, I think we’re just… We’re flying blind with a bunch of duct tape over the thing. So I think it’s really up to everyone else to ask themselves, what do I want? Is what I’m doing working? And if it is, don’t change anything. Go read another book, man. Live your best life. It’s not to say that there is a right and a wrong way to do it. But I think generally speaking in group dialogues, which I spend a lot of time on, and also, I think, with self-talk, we jump to conclusions. We tend to go from a question to an answer as quickly as possible, and that’s because I think one of the defaults, at least in the Western way of thinking, is we don’t like to sit with silence, we don’t like to sit with uncertainty. We’d like to have certainty. We talked…

Before we started recording, we talked about what’s my response to stress? Get ‘er done, let’s put our nose down, let’s get back to work. And so, sitting in silence with the question of “what should I be doing” is not comfortable for us. So I think if there’s one default I would change is, just amp up our comfort with silence or sitting with a question a little bit longer. Another is, a lot of conversations are ping-pong matches. We have that question of, “Well, what should we do about X?” And somebody says, “We should do this.” And that is usually the same person in a group. There is usually somebody who has just got this default speaker. They’re a mover, they just wanna initiate conversations. They are the least comfortable with silence, they are the most comfortable with thinking out loud. And so, everyone else in the group is then gonna have their conversational response anchored to that first response, and they maybe even haven’t had a chance to really think their thoughts.

So I think with the silence is how do we make sure we actually welcome in everybody else’s perspective? And then the third part is, well, how do we actually make a good decision of all the things that we’ve heard about to the thing that we can do? What’s a good set of heuristics to apply to making a good decision about it? And this is using design thinking. We talk about diverging and converging in creative problem solving, between the flaring and focusing, opening and closing, is exploring. And so, I just would love for everyone to open, explore, and close instead of just like, open, close, and sort of like, have as little debate in the middle as possible. That’s one big set of defaults that I would love for people to pump the brakes on and have a whole arc of opening, exploring, and a clear close that everyone can get behind.

Brett McKay: And you’re talking about this… You see these things in group dynamic, group conversation, but you also have them one-on-one, with a loved one, right?

Daniel Stillman: Oh, yeah, totally.

Brett McKay: The same kinda thing, right? You’re just like, oh, someone says something, okay, boom, here’s what I say. And they’re like, “Well… ”

Daniel Stillman: Yeah.

Brett McKay: Or the ping-pong match that goes on.

Daniel Stillman: Yeah. Well, so the example I love to give, my fiancee, when she comes to me with a challenge, and not to gender our speech, but I think a male pattern that is somewhat prevalent is the fixer, right? Somebody comes to you with a problem, and your default might be like, “Oh, well, here’s something you can do, honey.” Everybody raise your hand if that’s ever annoyed somebody that you are dating or in a marriage with, right? And just… I take a moment when she comes to me with a challenge, and I say, “Well, okay, so let’s pause for a second. Do you want me to coach you? Do you want me to just empathize with you? Do you want me to tell you what I think? Do you want solutions?”

“What’s the best way for me to show up here for you?” And that’s not inauthentic. I’m not changing who I am to do that, she knows that’s the way I show up. It’s like, “What conversation are we in here?” And sometimes she’ll say like, “I just need you to listen,” and I’m like, “Cool.” And when she tells me what’s going on, I say, “That sounds hard. I’m really sorry that you’re going through that.” But if she’s like, “Look, I really need a thinking partner here, I wanna tell you the problem and I wanna brainstorm with you,” I’m like, “Great, I’m gonna go get the sticky notes. What wall should we use that still [chuckle] is not covered by sticky notes in our house?” And that means taking control of our own responses, which is not trivial. Not easy to do.

Brett McKay: Alright. So let’s talk about… So one of the things that the design thinking does to figure out, you know, to start solving problems with the system or structure is finding out what the structure or system looks like in the first place. And in your book…

Daniel Stillman: Right.

Brett McKay: You sort of lay out, you kind of… You give your idea of what a conversational structure looks like and you call it an operating system, which I think is a useful analogy. And the first part of this operating system that I… You never think about with the conversation, but the first part, every conversation begins with an invite.

Daniel Stillman: Yeah.

Brett McKay: And I think people typically forget that there’s an invite to a conversation, because most conversations don’t start with, “I invite you to this conversation.”

Daniel Stillman: Right.

Brett McKay: But there is an invite. There is like a… When you start a conversation with someone, you’re throwing something out to somebody, say, “Hey, do you wanna take part in this conversation with me?”

Daniel Stillman: Yeah, and we’re talking about when somebody throws an angry or violent invite at you, you can respond in kind, which is kind of habitual or you can say, “Hey, wow, sounds like you’re angry,” or you cannot respond at all. Sometimes that’s the best way to just ignore the comments, let the haters hate. And so, it’s being really… When we start to look at the invitation as something we can open up the envelope or not, and when we open up the envelope we don’t have to RSVP to that party, those are… There’s a lot of choices. Once we slow down the interaction, I think there’s a lot of decision points along the pathway. And it also makes us a lot more… It makes me a lot more intentional about how I invite other people into things. And to maybe try and anchor this, I like to joke. It’s like, some people just like to hear themselves talk, but if you actually said to somebody, “Hey, I’d like to invite you over for a coffee, and I’m just gonna talk your ear off for an hour, how does that sound?”

Brett McKay: Right.

Daniel Stillman: If we invited them to the real… If we actually wrote the real invitation, would they come? Right? And most people in a one-on-one conversation, halfway through, if they’re just sort of like, “Blahhh,” their brain is just dumping. They’ll say halfway through like, “Oh God, I’m so sorry. I’ve just… How are you, man? I’m sorry, I’ve just been taking up the whole… All of the air here. What’s up with you?” They’ll notice that. And some people never notice that, and so you can just ask yourself, “Do I wanna keep coming to that party, if that’s what this party is about? What kinda parties am I inviting people to?” Just being really, really thoughtful and intentional about, “Are my invitations working? And am I really explaining what I really want?” ‘Cause I think one of the challenges people sometimes have is, there’s this classic, “Can we talk?” Which just sends a chill through everybody’s body, I think.

Brett McKay: Right, yeah.

Daniel Stillman: And so… And one of your questions was like, “How can we make better invitations?” And I think that’s just embedding other things into our invitation, like being really clear about what our goals are, or where it’s gonna happen or who’s invited and why? Like the story behind it. So just a pure invitation like, “Hey, can we talk?” It’s like… Maybe it works if there’s a lot of trust, if there’s a lot of connection and there’s… You’re actually touching them on their shoulder and you say, “Hey, can we talk?” And they look up and they say, “Sure, what’s up?” And then you tell them what’s up, and you can give them the big picture. But I think the more clarity, the bigger, the more zoom back you can give to people, the more helpful it is. But then you can over-explain. Who’s gonna read a four-page manual for the meeting, like, “Here’s our roles. Here’s our goals. Here’s our agreements. Here’s the agenda. Here’s our outcomes.” Those are all things that are really important to know, and that might even be easier for people to say yes to coming to the conversation, but that’s the power of editing. How can you say it, but how can you say it simply?

Brett McKay: Well, so thinking about being more thoughtful about your conversational invitations, and we typically… People say, “We need to talk” when you need to have that really hard conversation, right?

Daniel Stillman: Yeah.

Brett McKay: So what would be a better way to have… To invite someone to a hard conversation, whether you’re talking to an employee about their performance, there’s some sort of issue in your relationship, what would be a better invite? Is it just saying right up from the front like, “Hey, can we talk about X issue?”

Daniel Stillman: Yeah. So this is… Look, I wish there was a one-size-fits-all for this, but I tend to take inspiration from my own understanding of the physical world, and Amy Edmondson literally wrote the book on psychological safety, and there’s plenty of other people who talk about the importance of safety. And you have to have a sense of safety for a real challenging conversation to land well. I also just like to think about what makes physical safety possible, right? Like, when you walk into a space, what makes you feel safe versus what makes you feel unsafe? And I often use the analogy in some of my talks of… You turn down… New York doesn’t really have many alleyways anymore, but if you go to Chicago, Chicago has got a lot of alleys, and they are super murder-y alleys. You just sort of walk by this alley and it’s dark and you can’t even see the end of it, but you know there’s no escape on the other side. If you just walked down that… You just took a right-hand turn down that alleyway by accident and you’re in the dark space and then you can’t see the end of it, somebody steps behind you and now your exit’s blocked. Your whole body will freeze up, “I’m trapped.” Right?

The walls are closed in on us, there’s no sense of safety there. And if you’ve been to Asia and you walk down… There’s all these little alleyways in Bangkok and Tokyo, those little alleyways are filled with lights, they’re filled with like, tiny little restaurants. The alleyway might be the same size, but it’s just filled with life and with people, and we can also see the exits. We can see the exits and entrances on either sides. And so, I think about just this physical way of thinking about safety, seeing the exits, seeing other people, knowing there’s an out, knowing why we’re there, not coming in by accident. So it’s just like… It’s not sand-bagging somebody. You don’t just pull somebody into that difficult conversation without giving them time to prep. And I get it, look, people work in organizations. I think it’s terrible, people get fired on a Friday so that they can’t… They just like… You get pulled into this conversation and they’re like, “Hey, you’re fired. Go get your stuff. Get out of here.”

And they do that because there’s very low trust in a lot of organizations, where they think like, “Oh, if we actually let somebody know we’re concerned about their performance at work, and we give them tons of time to prepare for it, they’ll start downloading all the files from the central server and preparing their exit.” And I think that’s really terrible, we need to… I think it’s ideal to give people a heads up of like, “Look, I’m really concerned about… It just seems like you’re not engaged with the project,” and, “Can we talk about that? What do you need from me?” And I think often, people wait way, way, way too long to have these difficult conversations. The best time to bring up a difficult conversation is, as quickly as possible, right? So if you’re waiting until it’s desperately terrible and you have to do something about it, the stakes are gonna be really, really high and the person’s gonna be totally unaware that it’s going on. So, the sooner you have that conversation, the better. And just being as clear about what your needs are, and being clear about what the other person’s needs are as early on in the conversation as possible.

Brett McKay: So, okay, some of the takeaways I got as I was listening to you is, one, okay, if you’re making an invite for a conversation, so if it’s just like you’re calling up a friend because you wanna carp, say that. [laughter] Say, “Hey, can I call… Can I just… Can I kvetch with you for a little bit?”

Daniel Stillman: Yeah. Yes.

Brett McKay: Instead of being like caught off guard, and trapping your buddy with a 45 minute carp.

Daniel Stillman: Yes. [chuckle] Yeah.

Brett McKay: And your buddy might be like, “Hey, you know what? I don’t have time right now, let’s do it later.”

Daniel Stillman: Yeah. Right. But then they know what they’re walking into…

Brett McKay: Right.

Daniel Stillman: And they can step in with a full heart.

Brett McKay: And then the other issue too is like, if you are receiving the invite, if someone’s saying, “Hey, can we talk?” One thing you can do is be like, “Well, what’s this about?” Instead of just…

Daniel Stillman: Yeah.

Brett McKay: You can like… Even as the recipient, you can have a bit of… You can pull that lever of the invite so you can figure out what exactly you’re being invited to.

Daniel Stillman: Yeah. You can take back some power. It’s awkward, and I know that it can feel like a weird power play of like, “Oh, is there an agenda for the meeting?”

Brett McKay: Right.

Daniel Stillman: And, “Why isn’t there an agenda for the meeting? It seems like there ought to be one.” It’s like, “Hey, we’re… There’s an hour… We’re gonna ask for an hour of your time.” Well, what’s the plan? Who else is gonna be there? I should… Doesn’t that seem reasonable to ask that? But we have to find ways of asking that that don’t seem challenging or pushing back too hard.

Brett McKay: Yeah.

Daniel Stillman: And this is because we are collaborative creatures, we’ve evolved to be successful on this planet because we are collaborative. And so, conversations are collaborative, when somebody waves goodbye at you and you don’t wave back, you’re like, “Wow, that guy was a jerk, he didn’t wave goodbye.” And that’s just a tiny, tiny non-responsiveness of turn taking right there. And so, when somebody waits a day to not send an email, you’re like, “Wow, that guy thinks he’s better than responding to my emails.” Whereas we have no idea what’s going on in their world, and that’s why it’s always a good idea. We haven’t talked about the error and repair aspect of the OS, it’s just always good to assume that malice is the last option of all the things we think could be going on. They probably just have something else going on in their lives.

Brett McKay: Yeah, that’s a good point. So the boss who just calls meetings without giving you an agenda, you might assume, “Oh, this guy is just a power trip. He’s just getting people in this meeting and putting them on the spot.” And it might be the boss just doesn’t even… He’s not even thinking that. He’s just thinking, “Hey, we’re gonna have a meeting, so I can talk to you guys ’cause I like talking to you guys.”

Daniel Stillman: Right. And so, we have to train people, we have to start training [chuckle] people. Oprah once said… And I love… We could just collect all the amazing things that Oprah has said that we should live our lives by. But like, “We teach people how to treat us.” And people learn, people learn. So if we just respond to these meetings over and over again and we never say, “Oh, what’s the agenda? What’s the big goal? Who else is gonna be there?” Some of those clarifying elements, people will start to learn like, “Oh, Daniel needs this.” And they’re not unreasonable requests, I think that they can be couched, they can be phrased, you can invite somebody to give you that information in a way that is invitational rather than demanding.

Brett McKay: Yeah, that’s another thing. ‘Cause you think about, this is an invitation, this isn’t… As long as you let people know they still have autonomy…

Daniel Stillman: Yeah.

Brett McKay: It can go a long way of being like, “Yeah, I’ll do that.” It’s amazing what people… Whenever people feel like they’re being cornered and they don’t have a choice, they just dig in their heels…

Daniel Stillman: Yes.

Brett McKay: And they just won’t even do it. But if you’re just like, “Hey, I’d like to do this, I think we need to have you here, it’d be really important,” understand if you can’t make it, but let me know if you can’t.” And then, nine times out of 10, the person’s gonna show up, ’cause they’re like, “Oh, I have a choice here, and they respect my autonomy, so I will go there ’cause that person respects me.”

Daniel Stillman: Yeah. Well, this is the… Elon Musk famously makes all of the meetings of his organization optional, and that’s a real privilege to be able to say like, “Cool, I’d like you to come to this meeting.” But his perspective is, it’s more rude to make somebody stay in a room that they don’t feel like they are getting or giving value. And so, we call this… It used to be called the Law of Two Feet in open space technology, and now we call it the Law of Mobility. It’s about optionality. And you say, “Look, if you’re not getting value or giving value, I want you to go someplace where you think you are.” And a lot of people respond to that, and this goes back to the culture piece. A lot of people are like, “But if I make my meetings optional, no one will come.” And I’m like, “Well, that’s a problem with your meetings, dude. People should want to be there, because the problem you’re solving is interesting. People should wanna be there because you run them well, and because you respect people’s time. And so, those are all things that are completely within your control. So if you think people won’t come if you make them optional, there’s a deeper issue there.”

Brett McKay: We’re gonna take a quick break for a word from our sponsors. And now back to the show. So we talked about the invite. Another part of this conversation OS is the interface. What do you mean by interface?

Daniel Stillman: Yeah. Conversations just have a place and a space, and the space and the place affects it. So right now you and I are on and it’s just voice. And there’s actually something really interesting about just having a voice conversation. A lot of people are talking now about Zoom fatigue and digital meetings. And half of my clients were like, “How I get people to turn video on?” “Well, why do you want people to have video on?” “Well, then I know they’re engaged.” I’m like, “People can be disengaged with their video on.” So when you have video, the interface for the conversation is suddenly body language and eye contact. All of that stuff becomes available. When the interface is real life, we’ve got a broadband connection, we’ve got smell-o-vision, I can point, we can look, we can draw very easily. Reality is terabytes of data. It’s a super broadband connection, but the truth is our working attention is very narrow, and so there can be value to having a limited bandwidth connection. The classic example that I love to give is the value of texting somebody when you’re party hopping. Remember that? Going bar to bar, that was fun.

And I remember… This has happened to me. I don’t know if it’s happened to you, where you actually get annoyed with somebody who calls you when you text them. You say, “Well, we’re going to Bar X.” And they go, “Hey, are you going to Bar X?” I’m like, “Are you there yet?” I’m like, “We told you we’re going there, we’re going there now. I’m at a bar, it’s too loud. I can’t hear you.” So phone call is the inappropriate interface for dialogue when we’re in a noisy environment. Texting is the best, most efficient way. It’s a bad way to break up with somebody, it’s the wrong interface to break up with somebody after you’ve been dating them for any length of time. And so I think the interface says something about the conversation. So when you go into a board room and you go into one of those board rooms where the table is super duper long, that space says something. There’s a TV at one end, and whoever sits at the end by the TV, they’re in charge. We don’t take that seat, that seat is saved for somebody who’s important. So we might sit the second seat over or in the middle for when we really wanna play it safe.

And so the interface, the space and the place the conversation happens in, affects the conversation 100%. And it’s up to us to shape our spaces to give us the results we want. And this is like in our home life as well as in our work life, like there’s some people who make the recommendation that it’s better for couples to sleep in separate beds and then have a third bed to be intimate in. Some people say like, “You’ve got a cluttered space, you’ll have a cluttered mind.” So the space affects the conversation, 100%. Where do you have your meetings? Some people do these fake backgrounds, and I find them interesting. Some of them are really professional and some of them are way too professional, it tells me something like, “Wow, this person is trying kinda hard.” Some people are like… Have a messy background. They don’t care, and that’s fine, but it says something, it’s information. We’re getting information from where we are. That’s telling us something about what’s happening. So it’s up to us to shape the space. And I’ll anchor it in an example, Brett, ’cause in the book I… I remember walking into a client where they’d set up the room in a big U. And this is a really classic way to like, “Okay, we’re gonna have this meeting” and they put a projector in the middle, and that space says sage on the stage.

And the truth was I don’t use slides when I do workshops, 99% of the time, because I feel like that way of giving people information kinda puts them to sleep. And so during the first break I took the middle table of the U and I rotated it, and I put the chairs on either side of the table. What I find interesting was when people came back into the room they felt the difference in the room before they saw it. They were like, “What’s different?” ‘Cause when you first walk in you still kinda see the tables and chairs, you don’t notice the way they’ve shifted. They felt the difference in the quality of the room. And I think that’s something that we can tap into, whether it’s a one-on-one conversation or a group conversation. If people walk into your office, do they feel intimidated? Is that what you want? Or do they feel comfortable and at home? These are choices we can make in the spaces that we host dialogue in.

Brett McKay: Yeah, I really like that idea of being thoughtful about your interface. You sort of… The way I’ve applied it in my own life is…

Daniel Stillman: Yeah.

Brett McKay: For certain things, like if it’s like agenda, calendaring, just to-do’s, I can do that via a digital interface, where it’s like, “Here’s what we’re gonna do.” But if the conversation is nuanced and we need to really flesh something out, to me, you get on the phone for that or you do it in person, because if you try to handle that via text message or instant message, email or Slack, everything gets disjointed and you don’t get that gigabyte and terabyte of information that you get when you have a in-person conversation.

Daniel Stillman: Yeah. 100%. And so I think one of the things that’s so important for people to do is just to say, “Where would you like to have this conversation?” I’m a calendar person too, and I’ve worked with people where they are list people. They work in… They wanna work in like Asana or Trello, and teams and individuals like… They can have friction over where the information is going and what holds their dialogue together. Really, really early on in my relationship with my fiancee, we were doing long distance, she made a shared calendar for us. It was a big move, right? ‘Cause she was like, “I just wanna know when I’m seeing you next and I wanna block out some… I wanna put some blocks in there of things that I have going on.” And it moved things forward. It was a bold gesture to say that this is kind of where we’re gonna start having our conversation about when and how often we’re gonna be seeing each other, and we started a Slack channel together. I love having a Slack channel with her. Instead of buzzing her text or her email constantly with articles or links or ideas for the roof deck, I just throw them into these various channels. And so our conversation is organized and contained. And so these are just choices we can make about how we design the dialogue…

That we are having in ways that actually work for us and the people that we’re having them with. If she was like, “God, I hate Slack… ” I did it ’cause I know that she’s into Slack. She’s on a couple of other Slack networks, and so I was like, “Let’s have a Slack channel,” and she was like, boom, she made a half a dozen channels within the first hour. And that to me, we talk about the push and pull of conversation… I was like, oh, she’s into it. If it was empty and silent for the first month, I would have known, this is not working, I’m not getting the feedback I need in this dialogue. And we would have tried something else.

Brett McKay: So another element of the conversational OS are goals. We talked about that with the invitation. The invitation to a conversation, you can state your goals, but the goals can shift as you’re having the conversation, ’cause the conversation is dynamic. So I think that causes a lot of conflict in the conversation, ’cause one person thinks they’re talking about one thing and they thought everyone was on the same page, and then as the conversation progressed, the goals have shifted unknowingly, and so people are talking past each other and being frustrated.

Daniel Stillman: Yeah, and so I think one of the challenges is that people are afraid to share their goals and to find out other people’s goals explicitly, because we’re worried that if they’re far apart, we won’t know how to navigate it. But to me, I think that’s having clarity. Knowing the distance means we can start talking closely about how far apart we are, and one way to do that is actually, again, with physical interfaces. I’m a big… And maybe this is just my design thinking heritage, making visuals of where we are is helpful to close the gap. And there’s lots of frameworks for this. I’m a big fan of abstraction laddering, where we just… Let’s talk about all the reasons why, and let’s keep going, let’s go as many whys up as we can. Why do you want that? Why do you want that? Well, this is why [28:12] ____. Why, why, why, why, why. Ask a lot of whys. You may find out that some of their ultimate whys are not misaligned from your ultimate whys. Our initial whys might seem somewhat far apart, but if we go higher up, there may be a shared goal overarching all of it. And then we can say, “Well, so that’s what you want. What are some ways that we can get you to that?” And this is exploring all of our options, this is being experimental and collaborative. And if we look at all of the ways that we can get it before we start to commit to some…

Look, this is just what’s taught in negotiation school. I highly recommend… Wonderful, intellectual vacation. I went to the Harvard Negotiation Institute for a week, I learned so much, it was so fun to do negotiation simulations for a whole week with a bunch of lawyers and executives. And this is what they teach in getting to yes. Make sure you understand why somebody wants what they want, and then explore all the ways that seem valid to them to provide what it is that they want. And make sure that they’re also interested in exploring your whys and your hows, and then you can start to find some commitments together. It’s exploring without committing, which is not easy, but important.

Brett McKay: And you might even discover in that exploration of what the whys are that you have incompatible whys, and there’s no deal. And that’s okay, and I think a lot of people are afraid of that, like that’s a problem, but that’s an option, that’s always an option, to be like, “Well, looks like it’s not gonna work out. Great guy, I’m gonna move on and do something else.”

Daniel Stillman: Yeah, save some time, get to know as fast as possible, like, wow, there’s no there there. Cool, great. That was a quick meeting, thank you. But if you want to figure out where the yes is, you’ve gotta do all this work.

Brett McKay: And I guess as you’re having the conversation, make sure you’re… Somebody needs to check in, like, “Are we still talking about the same thing here?” ‘Cause that can…

Daniel Stillman: Re-inviting.

Brett McKay: Re-inviting, yeah, right. And this can happen in a business context or even in a personal context. It’s like if you’re having a conversation about money, sometimes, or oftentimes, you realize, no, this isn’t about money, we’re having a conversation about something else, and you have to make sure that you bring that out as you’re having that conversation.

Daniel Stillman: Yeah, and this is like… So I was looking at some of your past episodes, and I was looking at this weekly marriage meeting episode, and this is really about having a cadence of dialogue, like having a regular conversation in place to talk about important things. And the check-in, I think a lot of people talk about with big important relationships we have like marriages or business partnerships, we make a big agreement at the end, and then we just get to work. But checking in regularly and making sure, “Are you getting what you need out of this?” That’s a scary conversation to say, but if you’re doing it weekly, just like with the conversation we were talking about earlier about firing somebody, it’s like, “Hey, is this job still working for you? Are you getting what you need out of this job? Are you getting what you need out of me as a manager? Does this company work for you?”

I feel like people are scared to ask those questions because the answer might be no, but I think the most high-performing professionals know that eventually you wanna be hiring people who have ambition, and that means that hopefully they’re gonna be smarter than you as quickly as possible, and that means they might wanna move on eventually, and so you’ve gotta find ways to keep them engaged. And I think the same thing goes true for the people in our lives. We have to grow to meet them where they are, and if we’re not giving them what they need, gotta figure it out. And so I think checking in and saying, “Is this the conversation you still wanna be in?” And then having that conversation about what to do about it, it’s worthwhile, it’s not easy, none of this is. If it was, everybody would be doing it.

Brett McKay: So another element in the conversational OS is turn-taking, and this is I think something I think a lot of people… It’s like when they think about conversations, they often key in, they hone in on this. Who’s turn is it and when do I, how do I interject, and why is this guy talking so much and why isn’t he giving me a turn?

And I think that’s related to tempo too, which we’ll talk about. But you make the case, whenever… There’s sort of, a conversation, is that there’s a call and response, typically, in a good conversation. So someone makes the invite, throws something at you, and then you have a choice on how you’re going to respond. And you say… You’ve broken down, there’s five conversational responses or choices we have when it’s our turn to speak. So what are those? Walk us through those.

Daniel Stillman: Yeah, and I’ll also just say, it’s interesting, you see tempo or cadence as the flip side to this. My publisher actually was trying to make the case that I should collapse the OS down to fewer elements. He was like, “But isn’t turn-taking and cadence and threading, aren’t they all the same thing at different levels of zoom?” And I’m like, “Yeah… ”

Brett McKay: Yeah, but I think it’s useful to make them discrete, ’cause then you can tweak them.

Daniel Stillman: Yeah, ’cause to me cadence is about temperature. Temperature is one way I think of it, is like, is this conversation growing hot or cold, is one way to think about it, is like… This conversation’s getting a little bit hot, like I wanna figure out a way to cool it down, or wow, this conversation is getting way cold and I need to find a way to warm it up. Fast and slow is one way to think about cadence, and hot and cold is another. And yeah, that is an emergent phenomenon, I guess, of turn-taking. To me, turn-taking is without a doubt, certainly for facilitators… When I teach, and coach people on facilitation, which is one of the main things that I do in my business life, turn-taking is so clear because it’s so obvious.

We see speaking, the speaking is what happens, and I actually just interviewed a conversation analyst on my podcast, really, really brilliant woman who wrote a book called “Talk.” She literally just does scientific analysis of dialogue, a totally different aspect of this work. She points out that turn-taking really, it’s pairs. It’s a call and response. There’s an invitation and a response. And so the first thing… And we talked about this earlier, the first thing you can do with an invitation is nothing. You can just hold in silence, and that’s the, I think that’s in the middle of this diamond-shaped diagram that I drew out. Not many people will take that response of just waiting and seeing what happens, but it can be really powerful, ’cause people will say more, they might even change their initial invitation if you wait long enough. So you definitely do not have to respond to somebody.

Brett McKay: Can I interject? So there’s… I know a guy, there’s a guy that I worked [chuckle] with… I’m sorry I’m taking… I wanna get my turn now.

Daniel Stillman: Yeah, get it in there, well, ’cause, yeah, and you felt that move, you’re like, “There’s something here.”

Brett McKay: So there’s a guy that I’ve worked with at church, and as a profession, he’s an organizational guy, he just helps hospitals figure stuff out, I don’t know. But one of his… Really, I finally caught on to this thing that he did. You would talk to him, and then he would just be silent and just look at you, silent, and smile. And then you felt like, oh, man, I need to talk more, and you started talking more. [chuckle] And I was like, that’s actually pretty… That’s kinda slick. I don’t know if he’s doing it on purpose. I don’t think he did it on purpose, but I… I think he figured it out that if he just was quiet, people would tell him more things ’cause they felt uncomfortable.

Daniel Stillman: Right, so this is an amazing… And I’m really glad you noticed that and brought it up, ’cause it’s like… Some people are just reactive. So that’s one of the… There’s initiating, holding, and reacting, and a lot of us are reactive. As soon as someone… The average gap between turns is like 200 milliseconds, which is really fast. That’s like, the gun goes off and the sprinter barely starts sprinting. It’s really, really fast. And it actually takes something like 400 milliseconds to form a thought, which means that we are literally talking without thinking most of the time, or we’re preparing what we’re gonna say before somebody’s finished. And so when you talk about defaults and what’s in our operating system, this guy has got different software installed on his setup.

His hold operating system is just set to 11, and his react is turned way down. And if we start to see this in someone else, if we can notice it and name it, I think we can start to emulate it and invoke it. We can see and sense our own initiate and react modality, which is like, I like to talk and I like to respond, boom, boom, boom, boom, rapid fire. But we can, with intention, be like, “Look, I wanna be more hold-y. I wanna up my hold today.” And that’s where I think naming these things is helpful, to say, “Look, I wanna hold more,” or, “I wanna reflect more.” Holding is just silence. Reflecting is being like, “Hey, it sounds like you’re saying this. Is that right?” So it’s not adding more information, it’s affirming what somebody’s saying and getting more from them.

And reflecting, being reflective for someone else, that’s what a coach does, that’s what I do as a coach is I try to listen to what somebody’s saying and hold space for them… Not just in silence, I don’t just sit there for an hour and just say nothing and let them talk the whole time. I also say, “Well, it sounds like you’re saying this.” And then I go, do the fifth move, which is, sometimes, in very sparse amounts, reframing. Reframing is super dangerous, and I think we all have friends and coworkers who do this, where you come to them with a problem, they say… Well, they fix it. They’re like, “Well, there’s… Your pet had to die sometime.” Whoa, okay, thanks for reframing my problem for me. That’s not so helpful.

Brett McKay: Right.

Daniel Stillman: So reframing is a delicate thing. People have to be ready for it, it has to be welcome, and it has to be appropriate for the time. And so reframing people’s perspectives, my dad used to say, you don’t wake a sleeping man. You really wanna be careful who you shake awake. Giving people advice when they’re not ready for it is not so… It rarely works. And so I think reframing, you get the right to reframe after a lot of holding and reflecting. But I think initiating and reacting is like…

Seems like 90% of normal day-to-day dialogue is just talking and quick response, and the reason for that is, is that that’s the default. We actually… If somebody hesitates, we think they’re either rude or calculating. So it’s really interesting that this guy who is silent, that you see it as spacious and connecting with you instead of, “Wait, what’s he really thinking?”

Brett McKay: Well, that’s how it was at first. This was… I feel like this is uncomfortable, I’m just gonna blurt out my entire life to him, but then after while I was like, “Oh, that’s just what he does.” And so I got used to it. I’m like, “Okay, he’s just thinking about this stuff and it was fine.” It took a while to figure out though, and once I did it’s like, “Okay, that’s great.”

Daniel Stillman: Right. So saying to people… It’s so hard to do this in our culture. To say like, “You know, let me think about that for a second. I wanna give you a really good response, not just the first one that comes off the top of my head. So I’m thinking a couple of things now. It could be these three things.” That’s a really amazing way to re-design our conversations instead of feeling like we have to react, ’cause often I think we feel like somebody asks us a question and especially when it’s coming with force and with power behind it, there’s this feeling that we have to respond immediately.

Brett McKay: Right, you have to have a hot take. “What’s your opinion on this thing? This complex issue?” I’m like man, “I gotta think about that.” Like, “No, you can’t think! You’re gonna have one now!” and I’m like, “Oh jeez, I haven’t even thought about it.”

Daniel Stillman: Right, and if you say, “I need to think about it,” that makes you seem like you’re, I don’t know, an egg head or you’re calculating all the things we just talked about. It’s like what’s wrong with our larger cultural conversation operating system that saying, “No, let me think about that for a second,” and literally like having like two seconds of silence, that’s awkward! Of course, that’s awkward. So we have to find ways to create that space for ourselves. That’s why we um.

Brett McKay: Do more umming maybe. So another element. So when you’re having conversations, you’re never really gonna step on toes, mis-speak, misunderstand, assume bad faith, etcetera. So what do you do? How do you repair those errors so you keep the conversation going in a positive direction?

Daniel Stillman: Yeah, so there’s a couple of things. One, I have another sticky note here ’cause I was listening to your interview with Neil Rose, I think that’s… I’m pronouncing his last name correctly.

Brett McKay: The karma-factual guy, yeah.

Daniel Stillman: Yeah, and he talks about regrets, and I just wanna be really clear that the stuff that we’re talking about can be applied to one-on-one dialogues and group dialogues, but also with inner dialogue, ’cause I assume it’s not just me, there’s… I’ve got a couple of voices in there banging around and inner speech, the inner conversation is really, really fast, and I myself… And I know it’s just me, I’m really hard on myself sometimes. Some of the voices in my head, kind of just jump to conclusions at weak signals and use those weak signals to question my entire validity as a human being in the professional world, that inner self talk. So I think we’re actually nicer to other people than we are to ourselves, we talk about error and repair with the loved ones in our lives, we wanna to assume the best. I had an old business partner who described it as putting a 10 over their head, like the judges at an Olympics would hold up a 10 to rate your dive. And so one way to think about the error and repair operating systems we’re working with is, are we putting a 10 over people’s heads, or are we walking around with a 1 ready to rock, and so there are a lot of people who assume the worst of everybody. And so here’s the thing, if it’s a choice, which would you choose? Brett, would you rather think the best of everybody or the worst of everybody?

Brett McKay: I think the best of everybody, because if you think the worst it’s like you can’t… There’s no trust. There’s no possibility of trust.

Daniel Stillman: Right, but on the other hand, and I agree with you, if you’re gonna choose, it’s… Being angry takes a lot of effort, I think… And so I think it’s great to walk around thinking the best of everybody, but I’m also certain you know people who just don’t even notice when people are walking all over them.

Brett McKay: Right yeah, that’s true.

Daniel Stillman: Yeah, so it’s like being at one, being at zero or 10 or 11 is not great, and so we wanna be some place in the middle where we wanna see slights, but then inquire about them, like, “Hey, I noticed that. That didn’t feel so great. What did you mean by that?” But really actually ask, I’ll be like, “What did you mean by that?”. Have your fists already in a cartoon pugilistic stance. And I think we can do the same thing for ourselves. If we have regrets, that’s an inner part of ourself saying like, “I’m not happy about that.” And so it’s actually good to listen to that voice that’s feeling regret. That voice is saying, “Something’s not right here. I’m unhappy.” And I think we often say like, “Okay, I wanna live my life without regrets.” That was one of your opening points, in that episode. It’s like, “I wanna live my life without regrets,” and that seems like a great goal, but it’s actually… We’re gonna feel regrets, ’cause there’s gonna be a part of us that’s like, “I wanted something and I got something different.”

This is information. How do I listen to that voice? How do I have a conversation with that voice rather than just either dismiss it or accept it. And so I think that’s usually what happens with our external operating system on error and repairs. We either dismiss it 100% or accept it 100%. Instead inquire, negotiate, converse. The same way that we would do if somebody says like, “How much do you want for the bike?” And you’re like, “I want a 1,000 bucks.” And they’re like, “$5.” And you’re like, “No, it’s 1000.” We’re just gonna dig in. We’re not gonna have a negotiation. I’m like, “Look, I’ll accept 950.” So we’re negotiating. We’re going back and forth. So if that voice that it’s in me, it’s like, that’s unhappy, that is feeling regret, I wanna listen to it and say, “Look, I see what you’re saying. Thank you for the information.

There’s this other information. And now we’re gonna move on with the rest of our lives.” And so that’s, I think the same thing has to happen with our external error and repairs, like deciding what good looks like and what a mistake is means that we can hold people to the rules more easily. If we don’t have agreements, we can’t break them, nor can we hold people to them. So I think error, like many things, are better done up front than at the end. Article 48 of the European Union’s Declaration for Human Rights, I’m so proud of myself for remembering this says that, “Everyone shall be presumed innocent until proven guilty.” Amazingly, that’s actually not in the US Constitution. It’s somewhere deeper in our, some by-law or something, but I like this idea of innocent until proven guilty in our lives. Like why not?

Brett McKay: Yeah, why not? Well Daniel we talked about a lot of great things here. And what I love about, we didn’t hit everything, but I think, so the big take-away is thinking about conversations as having these different levers you can pull, and sort of, I hate using the word manipulate, ’cause it sounds like you’re manipulating some sort of [46:25] ____, but you can tweak them so that you can make a conversation more productive. And then like I said we haven’t talked about everything, and later on in the book you go into some practical applications of this stuff, but I think people what we talked about, they can start putting the stuff into practice. Where can people go to learn more about the book and your work?

Daniel Stillman: Yeah. Well, so first I think I agree with you about the manipulate thing, ’cause it means like, but it just means shape.

Brett McKay: Shape, yeah that’s what I’ve… Shape.

Daniel Stillman: And that’s why I say design. We’re designing, we’re shaping. I’m shaping it, and you’re, so we’ve co-designed, we’ve co-shaped this conversation, but I’ve trusted you as the interviewer to take us where you want us to go, and we’re all doing that in our conversations every day. We’re all trying to shape them for the better. This is just about people having some knowledge and perspective on the material. And so yeah, people can go to They can download a couple of free chapters of the book. That’s the easiest thing. Learn about the conversation OS and some of the basic principles. You don’t have to give me a penny, but the book’s available on Amazon. Obviously I’d love for people to check it out, and I have a podcast too. You can come look at some episodes. I interview people to just try and understand how do they design their conversations in work and in life. And so that’s the other place people can check out

Brett McKay: Fantastic. Well Daniel Stillman, thanks for your time. It’s been a pleasure.

Daniel Stillman: Oh man, it’s just such a joy. It’s an honor. You’re an amazing interviewer. So it’s been really fun for me.

Brett McKay: Well thank you so much, I appreciate that. My guest today was Daniel Stillman. He’s the author of the book Good Talk. It’s available on You can find out more information about his work at his website Also check out our show notes at where you find links to resources, reading delve deeper in this topic.

Well, that wraps up another edition of The AOM Podcast. Check at our website at where you can find our podcast archives plus thousands of articles we’ve written over the years, and if you’d like to enjoy ad free episodes of The AOM Podcast you can do so on Stitcher Premium. Head over to Sign up, use code manliness at check out for a free month trial. Once you’re signed up download the Stitcher app on Android or IOS. You start enjoying ad free episodes of the AOM Podcast. If you haven’t done so already, I’d appreciate it if you take one minute to give us a review on Apple Podcast or Stitcher. It helps out a lot and if you’ve done that already, thank you. Please consider sharing this show with a friend or family member who you think would get something out of it. As always, thank you for the continued support. Until next time this is Brett McKay reminding you all listening to AOM Podcast to put what you’ve heard into action.

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