In this episode, Brad and Brad talk with Daniel Stillman, a designer who helps companies and organizations apply the principles of design thinking to design better conversations. They discuss how design thinking can be applied in order to improve the interface of our conversations and how to make them more conversational.
00:00:30.000He draws on his background of design to show how he can use the principles of design thinking to improve the quality of our exchanges.
00:00:35.820Daniel and I kick off our discussion by unpacking the defaults of conversation people often fall back on.
00:00:40.180And then Daniel compares the structure of conversation to an operating system.
00:00:43.640And 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?
00:00:50.680We 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 particular dialogue.
00:00:58.600And 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.
00:01:07.360After the show's over, check out our show notes at awim.is slash conversation design.
00:01:11.060All right, Daniel Stillman, welcome to the show.
00:01:24.340So 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.
00:01:32.640It's even designing better conversations.
00:01:35.300And one of the first things that design thinkers do is figure out the default ways humans use a product, a service, a system.
00:01:45.060What are some of the defaults of conversation that may not be working for people?
00:01:50.040Yeah, so first of all, I struggled with this in writing my book because I really want people to be reflective practitioners of their conversations.
00:02:00.200Because most of us can't remember learning how to talk.
00:02:02.700You might remember learning how to play chess and maybe you got better at it and you learned some strategies.
00:02:07.380I think most of us are working with a patched together system like we're magpies.
00:02:13.800We saw something that we thought worked, and so we copied that and maybe it worked for us.
00:02:20.020So I think we're flying blind with a bunch of duct tape over the thing.
00:02:24.400So I think it's really up to everyone else to ask themselves, what do I want?
00:02:35.320It's not to say that there is a right and a wrong way to do it.
00:02:38.240But 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.
00:02:47.420We tend to go from a question to an answer as quickly as possible.
00:02:53.560And 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.
00:03:02.680We don't like to sit with uncertainty.
00:03:14.940And so sitting in silence with the question of, what should I be doing, is not comfortable for us.
00:03:20.620So I think if there's one default I would change, it's just amp up our comfort with silence or sitting with a question a little bit longer.
00:03:30.720Another is, a lot of conversations are ping-pong matches.
00:03:34.420We have that question of like, well, what should we do about X?
00:03:46.280They just want to initiate conversations.
00:03:48.240They are the least comfortable with silence.
00:03:49.980They are the most comfortable with thinking out loud.
00:03:52.520And so everyone else in the group is then going to have their conversational response anchored to that first response.
00:04:01.060And they maybe haven't had a chance to really think their thoughts.
00:04:04.840So I think with the silence is, how do we make sure we actually welcome in everybody else's perspective?
00:04:12.200And then the third part is like, well, how do we actually make a good decision?
00:04:17.180Of 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?
00:04:25.980And this is using design thinking, right?
00:04:28.360So we talk about diverging and converging in creative problem solving between the flaring and focusing, opening and closing is exploring.
00:04:38.960And so I just would love for everyone to open, explore, and close instead of just like open, close, right?
00:04:48.940And sort of like have as little debate in the middle as possible.
00:04:53.060That'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 like a clear close that everyone can get behind.
00:05:07.960And you're talking about this, you see these things in group dynamic, group conversation.
00:05:11.620But it also happened like one-on-one with like a loved one.
00:06:47.980So let's talk about, so one of the things that design thinking does to figure out, to start solving problems with the system or structure is finding out what the structure or system looks like in the first place.
00:06:59.360And in your book, you sort of lay out, 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.
00:07:09.720And the first part of this operating system that you never think about with a conversation, but the first part, every conversation begins with an invite.
00:07:18.000And 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.
00:07:54.520Sometimes that's the best way to just ignore the comments, let the haters hate.
00:07:58.800And so it's being really, when we start to look at the invitation as something we can open up the envelope or not.
00:08:05.440And when we open up the envelope, we don't have to RSVP to that party.
00:08:10.140There's a lot of choices once we slow down the interaction.
00:08:13.700I think there's a lot of decision points along the pathway.
00:08:18.080And it also makes us a lot more, it makes me a lot more intentional about how I invite other people into things.
00:08:25.540And to maybe try and anchor this, I like to joke, it's like some people just like to hear themselves talk.
00:08:36.880But if you actually said to somebody, hey, I'd like you to invite you over for a coffee, and I'm just going to talk your ear off for an hour.
00:08:51.460And most people in a one-on-one conversation, like halfway through, if they're just sort of like, their brain is just dumping, they'll say halfway through, like, oh, God, I'm so sorry.
00:09:37.580And so one of your questions was like, how can we make better invitations?
00:09:40.560And I think that's just embedding other things into our invitation, like being really clear about what our goals are, or where it's going to happen, or who's invited and why, like the story behind it.
00:09:55.840So just like, just a pure invitation of like, hey, can we talk?
00:09:58.540It's like, you know, maybe it works if there's a lot of trust, if there's a lot of connection, and you're actually touching them on their shoulder.
00:10:29.300Those are all things that are really important to know, and that might make it easier for people to say yes to coming to the conversation.
00:10:36.020But, you know, that's the power of editing.
00:10:38.640Like, how can you say it, but how can you say it simply?
00:10:42.080Well, so thinking about being more thoughtful about your conversational invitations, you know, we typically, people say we need to talk when you need to have that really hard conversation, right?
00:10:51.520So 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?
00:11:01.840Is it just saying, like, right up from the front, like, hey, can we talk about X issue?
00:11:06.940I mean, 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.
00:11:15.580And Amy Edmondson literally wrote the book on psychological safety, and there's plenty of other people who talk about the importance of safety.
00:11:24.940And you have to have a sense of safety for a real challenging conversation to land well.
00:11:32.000I also just like to think about what makes physical safety possible, right?
00:11:37.580Like, when you walk into a space, what makes you feel safe versus what makes you feel unsafe?
00:11:43.700And I often use the analogy in some of my talks of, you know, you turn down, New York doesn't really have many alleyways anymore, but if you go to Chicago, Chicago's got a lot of alleys, and they are super murdery alleys.
00:12:00.900You just sort of, like, 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.
00:12:08.480If you just walked down that, you just took a right-hand turn down that alleyway by accident, and you're in this dark space, and then you can't see the end of it, somebody steps behind you, and now your exit's blocked.
00:12:29.840And 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.
00:12:43.520The alleyway might be the same size, but it's just filled with life and with people, and we can also see the exits.
00:12:49.460We can see the exits and entrances on either sides.
00:12:52.540And so I think it's 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.
00:13:05.840So it's just like, it's not sandbagging somebody.
00:13:08.320You don't just, like, pull somebody into that difficult conversation without giving them time to prep.
00:13:26.200And 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.
00:13:44.600We 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 we talk about that.
00:13:57.280I think often people wait way, way, way, way too long to have these difficult conversations.
00:14:03.380The best time to bring up a difficult conversation is as quickly as possible, right?
00:14:09.540So if you're waiting until it's, like, desperately terrible, and you have to do something about it, the stakes are going to be really, really high, and the person's going to be totally unaware that it's going on.
00:14:20.040So the sooner you have that conversation, the better.
00:14:24.400And 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.
00:14:33.620Some of the takeaways I got as I was listening to you was, 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 want to carp, like, say that.
00:14:43.940Say, hey, can I call, can I just, can I, can I kvetch with you for a little bit instead of, instead of being, like, caught off guard, you know, and, like, sort of entrapping your buddy with, like, a 45-minute carp.
00:14:56.480And your buddy might be like, hey, you know what?
00:15:03.940And they can step in with a full heart.
00:15:05.780And then the other issue, too, is, like, if you, if you are receiving the invite, right, if someone's saying, hey, can we talk?
00:15:11.040Like, one thing you can do is be like, well, what's this about?
00:15:14.180Like, you know, instead of just, you can, like, even as the recipient, you can have a bit of, you can kind of pull that lever of the invite so you can figure out what exactly you're being invited to.
00:16:07.220And that's just a tiny, tiny non-responsiveness of turn-taking right there.
00:16:12.180And so when somebody waits, like, a day to not send an email, you're like, wow, that, that guy thinks he's better than responding to my emails.
00:16:20.580Whereas we have no idea what's going on in their world.
00:20:48.340And 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.
00:21:46.400That seat is saved for somebody who's important.
00:21:50.000So, we might sit the second seat over or in the middle if we really want to play it safe.
00:21:54.900And so, the interface, the space and the place the conversation happens in affects the conversation 100%.
00:22:02.960And it's up to us to shape our spaces to give us the results we want.
00:22:11.600And this is like in our home life as well as in our work life.
00:22:14.520Like, 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.
00:22:23.680Some people say, like, you've got a cluttered space.
00:24:06.680Or do they feel comfortable and at home?
00:24:08.860Like, these are choices we can make in the spaces that we host dialogue in.
00:24:14.300Yeah, I really like that idea of being thoughtful about your interface.
00:24:16.420I mean, the way I've applied it in my own life is for certain things, like if it's like agenda, like calendaring, like just like to-dos, like I can do that via digital interface, right?
00:24:28.380It's like, here's what we're going to do.
00:24:29.960But if like the conversation is nuanced and we need to like really flesh something out, like to me, you get on the phone for that or you do it in person.
00:24:38.400Because if you try to handle that via like text message or instant message, email or Slack, like everything is disjointed and you don't get that, like, you know, like that gigabyte and terabyte of information that you get when you have an in-person conversation.
00:25:28.000Because she was like, I just want to know when I'm seeing you next and I want to block out some, I want to put some blocks in there of things that I have going on.
00:25:37.120It was a bold gesture to say, this is kind of where we're going to start having our conversation about when and how often we're going to be seeing each other.
00:25:48.140And we started a Slack channel together.
00:25:51.400I love having a Slack channel with her.
00:25:53.060It's instead of like buzzing her text or her email constantly with articles or links or ideas for the roof deck.
00:26:02.000I just throw them into these various channels.
00:26:05.100And so our conversation is organized and contained.
00:26:08.300And 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.
00:26:39.560If there was empty and silent for the first month, I would have known this is not working.
00:26:46.240I'm not getting the feedback I need in this dialogue.
00:26:49.560And we would have tried something else.
00:26:51.260So another element of the conversational OS are goals.
00:26:54.840We kind of talked about that with the invitation.
00:26:56.700Like the invitation to a conversation, you can state your goals.
00:26:59.500But the goals can shift as you're having the conversation because the conversation is dynamic.
00:27:05.340So I think that causes a lot of conflict in the conversation because one person thinks they're talking about one thing and they thought everyone was on the same page.
00:27:13.720And then as the conversation progressed, the goals have shifted unknowingly.
00:27:18.400And so people are talking past each other and being frustrated.
00:27:21.280Yeah, 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.
00:27:34.880But to me, I think that's having clarity.
00:27:38.300Knowing the distance means we can start talking closely about how far apart we are.
00:27:43.620And one way to do that is actually, again, with physical interfaces.
00:27:47.120I'm a big, and maybe this is just my design thinking heritage, making visuals of where we are is helpful to close the gap.
00:27:58.740And there's lots of frameworks for this.
00:28:02.240I'm a big fan of abstraction laddering where we're just like, let's talk about all the reasons why and let's keep going.
00:28:16.480You may find out that some of their ultimate whys are not misaligned from your ultimate whys.
00:28:23.840We may be, we may, our whys, our initial whys might seem somewhat far apart.
00:28:28.960But if we go higher up, there may be a shared goal overarching all of it.
00:28:33.660And then we can say, well, so that's what you want.
00:28:36.200What are some ways that we can get you to that?
00:28:38.040And this is exploring all of our options.
00:28:39.820This is being experimental and collaborative.
00:28:41.980And if we look at all of the ways that we can get it before we start to commit to some, I mean, look, this is just what's taught in negotiation school.
00:28:50.320I went, I highly recommend wonderful intellectual vacation.
00:28:54.560I went to the Harvard Negotiation Institute for a week.
00:30:12.280And this can happen in a business context or even in a personal context, right?
00:30:16.640It's like, you know, if you're having a conversation about money, you know, sometimes or oftentimes you realize, no, this isn't about money.
00:31:05.060But 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?
00:31:12.700Are you getting what you need out of this job?
00:31:14.980Like, are you getting what you need out of me as a manager?
00:32:48.720Yeah, and I'll also just say, it's sort of interesting that you see tempo or cadence as the flip side to this.
00:32:54.700My publisher actually was trying to make the case that I should collapse the OS down to, like, fewer elements.
00:33:00.600He's like, but isn't turn-taking and cadence and threading, like, are they kind of all the same thing at different, like, levels of zoom?
00:33:06.820And I'm like, yeah, but I think it's useful to make them discreet because then you can tweak them, right?
00:33:12.580Yeah, because to me, cadence is about temperature.
00:33:15.240And temperature is one way I think of it.
00:33:17.120It's like, is this conversation growing hot or cold is one way to think about it.
00:33:22.100It's like, this conversation is getting a little bit hot.
00:33:24.660Like, I want to figure out a way to cool it down.
00:33:26.420Or like, wow, this conversation is getting way cold and I need to find a way to warm it up.
00:33:31.180You know, fast and slow is one way to think about cadence and hot and cool is another.
00:33:34.580And yeah, it is an emergent phenomenon, I guess, of turn-taking.
00:33:39.220To me, turn-taking is, without a doubt, certainly for facilitators.
00:33:42.700When I teach and coach people on facilitation, which is, like, one of the main things that I do in my business life, turn-taking is so clear because it's so obvious.
00:35:31.340And I was like, that's actually pretty, it's kind of slick.
00:35:34.340I don't know if he's doing it on purpose.
00:35:35.300I don't think he did it on purpose, but I think he figured it out that if he just was quiet, people would tell him more things because they felt uncomfortable.
00:36:12.120And 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 going to say before somebody's finished.
00:36:27.420And so, when you talk about defaults and what's in our operating system, this guy has got different software installed on his setup.
00:36:36.640His hold operating system is just set to 11, right?
00:38:29.060It has to be welcome, and it has to be appropriate for the time.
00:38:34.180And so, reframing people's perspectives, my dad used to say, you know, you don't wake a sleeping man.
00:38:41.340You really want to be careful who you shake awake.
00:38:46.020You know, giving people advice when they're not ready for it is not so, it rarely works.
00:38:51.380And so, I think reframing, you get the right to reframe after a lot of holding and reflecting.
00:38:56.840But I think initiating and reacting is like, seems like 90% of normal day-to-day dialogue is just talking and quick response.
00:39:07.920And the reason for that is, is that that's the default.
00:39:10.080Like, we actually, if somebody hesitates, we think they're either rude or calculating.
00:39:15.240So, it's really interesting that this guy who's silent, that you see it as spacious and connecting with you instead of, well, wait, why is he?
00:39:25.300And, you know, what's he really thinking?
00:40:27.220And you're like, oh, geez, I haven't even thought about it.
00:40:30.300Right. And if you say, I need to think about it, that makes you seem like you're, I don't know, an egghead or you're calculating all the things we just talked about.
00:40:37.300It's like, what's wrong with our larger cultural conversation operating system that saying, let me think about that for a second.
00:40:45.680And literally, like, having, like, two seconds of silence.
00:41:30.440And I just want to be really clear that the stuff that we're talking about can be applied to, like, one-on-one dialogues and group dialogues, but also with inner dialogue.
00:41:43.480There's, I've got a couple of voices in there banging around.
00:41:47.740And inner speech, the inner conversation is really, really fast.
00:41:51.640And I, myself, and I know it's just me, I'm really hard on myself sometimes.
00:41:56.720Some 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.
00:43:12.360But on the other hand, and I agree with you, like, if you're going to choose, like, it's, being angry takes a lot of effort, I think.
00:43:19.180And 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.