Conversation Design with Daniel Stillman

"Human beings are conversational animals and we live our lives one conversation at a time."

Conversations matter. Whether you’re pressed to make an important business decision, feel the need to educate someone on a topic, or even just want to commiserate, the way you approach and frame your words—spoken or written—will impact the outcome of the conversation.

On this episode of Time Limit, our guest Daniel Stillman digs in on how to design conversations to achieve the best outcomes possible. As a conversation designer and consultant, Daniel works with clients and organizations of all shapes and sizes to help them frame and sustain productive and collaborative conversations to deepen their facilitation skills. The basis for the interview is Daniel’s new book, Good Talk: How to Design Conversations that Matter. The conversation covers a wide range of topics, including:

  • What is conversation design?
  • How do you architect a conversation?
  • Finding the language to frame a conversation
  • How to make someone feel heard
  • Working with a team to improve conversations
  • Tips to improve conversations
  • Practicing active listening
  • How to design a meeting to get what you need out of it
  • Designing conversations for the diversity of neurological and sociological abilities that people have in order to get the best contributions. 
  • How to address difficult conversations
  • Facilitation tips and tactics

Resources mentioned in this episode::

About our guest


Daniel Stillman
Independent Design Facilitator

Daniel Stillman designs conversations for a living, and insists that you actually do that too.

As an independent design facilitator, he works with clients and organizations of all shapes and sizes (From Google to Visa, to name a few) to help them frame and sustain productive and collaborative conversations, deepen their facilitation skills, and coach them through the innovation process.

He’s the author of Good Talk: How to Design Conversations that Matter, a handbook for leaders looking to create change. His first book, The Paper Airplane Experiment and the 30 Second Elephant is about origami and teams and yes, it’s as strange as it sounds.

Daniel also hosts The Conversation Factory podcast where he interviews leaders, changemakers and innovators on how they design the conversations in their work and lives.

Episode Transcript


Brett Harned:                                          Hey welcome back to Time Limit. I'm really excited to jump right into my interview with Daniel Stillman. Daniel's an independent design facilitator. So he works with clients and organizations of all shapes and sizes basically to help them frame and sustain productive and collaborative conversations to deepen their facilitation skills and then he does some coaching around the innovation process. I'm so happy to have connected with Daniel and to talk to him about his new book, Good Talk: How to Design Conversations that Matter. We'll jump right into the conversation and talk about conversation. It was a really fun one for me, because like Daniel says, "Human beings are conversational animals and we live our lives one conversation at a time." I think you'll enjoy the conversation and find a few helpful tips to keep all of your conversations productive and helpful. So check it out.
                                                      Daniel Stillman, welcome to the show. Thanks so much for making the time to chat with me today. Appreciate you being here.

Daniel Stillman:                                       Brett thanks for making this happen.

Brett Harned:                                          Yeah.

Daniel Stillman:                                       It wasn't easy.

Brett Harned:                                          It wasn't easy.

Daniel Stillman:                                       You had to be committed to making time. It's hard to make time in life sometimes.

Brett Harned:                                          It's really weird that we're trapped in our homes, but we still are having a hard time to find time. [crosstalk]

Daniel Stillman:                                       All these people who are like... got extra time to take on a new hobby.

Brett Harned:                                          Yeah. I'm with you on that.

Daniel Stillman:                                       I know that that's reality for a lot of people, but it's... somebody actually dropped in on a Zoom call with me today. I don't know if this has ever happened to you. I know I'm veering the conversation already, but literally, he invited... I was suddenly saw a pop up with Skype, where somebody was inviting me to a Zoom call. He dropped in on me. Nobody does that anymore.

Brett Harned:                                          No.

Daniel Stillman:                                       I had to drop it.

Brett Harned:                                          Everything is so tightly planned.

Daniel Stillman:                                       Yeah, so I think this is actually something interesting to unpack at some point. We can still have that in this digital place. That-

Brett Harned:                                          We can.

Daniel Stillman:                                       Impromptu gathering.

Brett Harned:                                          Yeah, I guess I typically just do that via Slack, not with a drop in call. I would never-

Daniel Stillman:                                       Yeah.

Brett Harned:                                          Assume that someone's just ready to see me, or to be seen really.

Daniel Stillman:                                       Right. Right. Right. So texting is polite in my world and calling is rude.

Brett Harned:                                          Yeah. Yeah, it's like the drop in, right? You don't want somebody to just drop by your house with no notice. That's funny.

Daniel Stillman:                                       But some people also still feel like a Slack message in the middle of the night doesn't... don't they know that I'm-

Brett Harned:                                          Yeah.

Daniel Stillman:                                       Because they... I have to respond, but do we?

Brett Harned:                                          It's very true. I say no you don't.

Daniel Stillman:                                       Right.

Brett Harned:                                          Especially in the middle of the night, or anytime during the day. It's up to you. Do what you want with your [crosstalk]

Daniel Stillman:                                       This is already conversation design, right? We're already talking about-

Brett Harned:                                          It is.

Daniel Stillman:                                       How do we prefer our conversations to be architected? Where and when would we like them to happen and when are they appropriate? When do we feel like they're appropriate or inappropriate and people come to blows over these things. I can't believe he Slacked me in the middle of the night. This guy.

Brett Harned:                                          Did we architect this whole intro to the podcast interview?

Daniel Stillman:                                       No. Just everything's about conversations for me, so that's a natural segue no matter what.

Brett Harned:                                          It's so funny. All right. So just to give our listeners a little context before we just go on this 30 talk of rambling. We're here to talk about your new book, which is coming out really soon and it's called Good Talk.

Daniel Stillman:                                       Yeah.

Brett Harned:                                          And it's all about conversation design. I think that term, conversation design is definitely a little bit new to me. I also feel like in the digital industry that I come from that you're in, it feels like a lot of things are turned into design including meeting design and-

Daniel Stillman:                                       Yep.

Brett Harned:                                          I'm curious, where did that term come from and what drew you to it?

Daniel Stillman:                                       Yeah. Well so let's talk about design first, because it means so many things to so many people. I went to school for industrial design at Pratt and Pratt has this bow house heritage, and so we spent an entire semester literally studying negative space and another class, we talked about whether curves were fast or slow, right? So we're really thinking about design from this granular level, and I feel like we've all been in this era growing up with design rapidly changing what it is. This is the classic Steve Jobs quote... I don't like quoting Steve Jobs because I think it's generally agreed upon that he was a jerk, but that said, he talks... there's that quote about "Design isn't how it looks, it's how it works."
                                                      I feel like we've grown up from design being... especially in the 80s and 90s where it was just about form to where it was about functionality and it's about brand, and it's about experience. So for me particularly, when I got into industrial design, as soon as I got in to working at a consultancy on the research and strategy side, it's like, "Oh well actually industrial design is dead. Nobody told me." It had its heyday in the 50s and everything we were designing had a screen.

Brett Harned:                                          Interesting.

Daniel Stillman:                                       And somebody else was designing what happened on that screen, and all of the action was happening on the screen. So I was touring the country interviewing people about the future of home theater and we were talking about speaker location, and how they installed it and what height they put the TV, and how could we design the bezel so beautifully, and how could we make it so that it was easier for people to setup their home theater and try to understand that, and guess what? Somebody else was designing the... what was called internet protocol television systems on the television. We're like, "Oh my god, we're going through all this trouble to design this television and nobody's looking at the television." Right?
                                                      So my boss was like, "What is this thing? We're losing this other half of the business. We're not designing the total experience for this product." So we started trying to win what were then called interaction design projects.

Brett Harned:                                          Interesting. Yeah.

Daniel Stillman:                                       So I... as soon as I got out of industrial design school, everyone was like, "Have you heard about interaction design kid?" I'm like, "Ooh, tell me about that." They're like, "Well..." I was like, "Wait a minute, this is really just a lot like industrial design." Because industrial designers think about interaction like any good industrial designer things about the unboxing of the product, right?

Brett Harned:                                          Right.

Daniel Stillman:                                       Think about all the videos you watch of people unboxing their favorite products, right? So to me, experience design was this next type of design that popped up along the pathway. So I'm going from 2007 to 2008 and 2009 and people are like, "Well, it's actually experience design. No, no it's customer experience design. No, it's all services." Everything is services. We're selling the products just... are just disintermediating services and so without the brain and without the service, what is your phone? Your phone's not a product. You buy the phone, but it's connected to a universe of services.

Brett Harned:                                          Right.

Daniel Stillman:                                       So there's all these people who are like, "No, no, no it's service design and if you really want to understand what you're doing, you have to unpack services." There's people, places, props, partners... I forget what the last P is, and so there's all this language that we have around what it is that we're doing. You can just say, "Oh well, it's just somebody selling their consultancy services deeper into an organization." If I was cynical Brett, I would agree with you, but I think new language helps you describe things better. Service design definitely gave us designers new eyes and it allowed industrial designers to take their fundamental skills of thinking about people and customers, all stakeholders process and impact and saying, "How do I stretch this out and really make something that matters?"
                                                      So for me, one of the things I realized when I got into... and this is a long tirade, so stop me anytime but-

Brett Harned:                                          No, it's great.

Daniel Stillman:                                       When I got into the consultancy world, when I started working at a design agency, I think what I thought was... as many designers do, I just have to make something good. What I really had to do is I had to design this whole process to bring my clients along with me. I don't think I had the language for it, but what I was doing was designing conversations. I was designing these workshop experiences to extract information from them, or to incept information into their heads. So this is like designing for and then designing with. It wasn't until much, much later I started teaching design thinking to non-designers because I thought... I had this idea of "Well design thinking is the stuff I learned after design school, so anybody can do it. If we all know the language of design thinking, we can all play better together." I don't have to explain everything to my clients every time we're doing it and we can play this game called innovation and they'll be along the ride with me.
                                                      A group I worked in 2015 called their facilitative practice conversation design, and it really insulted me when I first heard it because I was like, "You're not designers and what is that? That's gross." Honestly, I was like, "That's kind of douchey." But it really tickled my brain and I was like, "Well what does it mean to design a conversation? What is the material of conversation?" I literally, I sat down and I did four interviews with some people I know and respect. I was like, "Is this the next type of design?" Going through all of those phases I'd gone through in my career, I was like, "Is this what we need to be aware of as designers? Is this the language we need to be able to describe what we're actually doing?" Because I'd been thinking about workshop design and facilitation as experience design.
                                                      You get a bunch of people in a room and you design an experience for them. So I was using the language of experience design to teach people about designing better workshops.

Brett Harned:                                          Okay.

Daniel Stillman:                                       So this idea of "What are we doing when we design a workshop or a meeting well?" I think what's really problematic for me is that people look at... they want blog posts of tips as if tips will tell you how to do it. It's as if reading an essay about playing a guitar can help you shred, right? So I think there's stuff about designing conversations that there's tips and tricks and then there's this other thing of just can you feel conversation as a material, in the same way that we've started to think about products and services and experiences as materials that we have to shape. We mold them and we try to make them work. So if we want to critique a product, service or an experience, we have a language for it.
                                                      If we want to critique a meeting or a workshop, or a conversation, or a dialogue, or a process, we have almost no language for it. So a lot of the book is just me scraping around the universe for language. I will now pause. That was the whole-

Brett Harned:                                          No.

Daniel Stillman:                                       That's everything.

Brett Harned:                                          It's really interesting. I mean, so I read the preview of the book on Amazon and in that preview, you tell a story about an experience that you had that got you into this topic when you... I guess when you were in that research job.

Daniel Stillman:                                       Yeah.

Brett Harned:                                          I think it's really interesting because what you're doing from what I can see, is you're kind of... conversation is something that we all do.

Daniel Stillman:                                       Right.

Brett Harned:                                          Every person, right?

Daniel Stillman:                                       Yes.

Brett Harned:                                          So what I think you're doing really well is bringing your two worlds together, right? Your work world and your home world, and you're relating the topic around both and making it relevant to anyone. One of the questions that you posed earlier was what does it mean to design a conversation?

Daniel Stillman:                                       Yeah.

Brett Harned:                                          I'm just curious, you talked about framing conversations for workshops or around feedback, or around really specific scenarios that you can plan for.

Daniel Stillman:                                       Yeah.

Brett Harned:                                          It... does conversation... does design relate to the day to day?

Daniel Stillman:                                       Oh yeah. I mean totally, 100%.

Brett Harned:                                          Okay.

Daniel Stillman:                                       I think part of it has to do with your feel for the thing. I'll give you an example. So I try to describe what I thought the levers of conversation design were. What were the fundamental pieces? Although it's pretty much impossible to agree on this is what it is. When I submitted a fourth draft to my publisher, he was like, "Wait, these three things feel like they're one thing." I'm like, "Well they're different." So one of the things is cadence. What's the pace or the musicality of the conversation? That's just something I've become more aware of and in that... I think in the example you're talking about is me interviewing somebody and we all know this experience when you ask somebody a question and they give you an answer. There's a moment where they pause and then... I started thinking I had to ask my next question because I was aware of time. I had other stuff I wanted to learn and the person I was interviewing and I started speaking at the same time.
                                                      What that is, is a conversational collision. That's an error. Error is something that happens in every conversation. We collide and what happens is you're like, "Hey, what were you... oh no, wait, what were you going to say?" And then you're like, "Oh, I can't remember now." I was like, "Oh geez, I destroyed her half of the conversation because I... my cadence, my pace was too fast." Right? We've definitely... I feel like this is a Seinfeld episode like there's a slow talker up. It's like, "He's a slow talker." [crosstalk] he would talk slow and they're okay with bigger pauses, but generally, we only allow a 200 millisecond gap between when one person speaks and another speaks. This is... actually from what I've read, fairly consistent across many cultures and even with sign language conversations.
                                                      We want somebody to feel heard and we want to be responsive, so we respond. But here's what weird, and this is why we talk about the material of conversation. It takes approximately 600 milliseconds to form a thought of that you're going to say. So if you do the math, if when Brett stops talking and in 200 milliseconds I respond, and it takes me 600 milliseconds to formulate a response, then one of two things is happening. Either I'm speaking total garbage, right? Because I'm speaking with half a brain. If I open my mouth in 200 milliseconds after you stop talking, that means that my... what I'm... and this is why people say um or ah, wow that's interesting. So I'm either saying something that's total garbage, or I've starting thinking about what I was going to say 400 milliseconds before you stopped. Right?

Brett Harned:                                          It's really interesting. Yeah. I mean, so I am that guy. I feel like every day when I'm in a Zoom call or a Google Hangout or whatever service we're using, there is an issue with people jumping on what someone else said.

Daniel Stillman:                                       Yes.

Brett Harned:                                          And I feel... and you feel so terrible when you cut someone off because you want their-

Daniel Stillman:                                       Yes.

Brett Harned:                                          Their thought to be completed and give them the space and time to do that, but if there's a long pause, it feels awkward.

Daniel Stillman:                                       Yes.

Brett Harned:                                          If you have a thought, you're just naturally going to jump in.

Daniel Stillman:                                       Yeah.

Brett Harned:                                          So are there... do you have any tips around how you can handle that situation?

Daniel Stillman:                                       Yeah, well I mean this is... and again, this is the thing I was talking about where there's ways of doing, so I can give you... there's ways I could say, "Oh, just wait more." But the willingness to wait more, the doing requires different ways of being, which is not to say you have to be different, or we all need to be different than we are, but in order to actually leverage the tools, we have to change our approach.

Brett Harned:                                          Right.

Daniel Stillman:                                       That [crosstalk] the problematic and this is behavior change and culture change in general. If I just stated a company that's having... or a team that's having issues, well just be nice to each other guys. Right? And they're like-

Brett Harned:                                          That works.

Daniel Stillman:                                       "Well how?" I'm like, "Just be nice." This is like your mother like, "Why can't you two just get along? I don't get it." Right? So if I just say, "Well Brett, just get everyone to agree that it's agree that silence is all right." Now you can actually do that. So this is the thing that's funny, I read an article... if you Google the types of meetings, there's lots of classification systems for this and [inaudible] had this amazing article where they were like, "Here are the six types of meetings that your team should always have and the one they never should." Total awesome click bait title, and the one that they never should was the meeting about meetings. I was like, "Oh my god, that's the meeting everybody needs to have."

Brett Harned:                                          Interesting.

Daniel Stillman:                                       You need to have at least one meeting about your meetings, I don't know, not every week. That's too much and so now we're talking about cadence again. How often Brett do you think a team or an organization should have a meeting about meetings?

Brett Harned:                                          Wow. It's a tough question, because I think it depends on what that team is doing. What they're willing to do. It has a lot to do with the culture of the team and the preference of the team.

Daniel Stillman:                                       Yeah. So I think even getting the team to decide that cadence would be fine. But then again, this is also my way of... because I come at it from a coach's perspective. I don't want to give people best practices because I actually think that inhibits their free will and their learning, and that's based on my own belief that people are most motivated when they feel they have the most power and agency, and that's based on my understanding from the conversation [inaudible] powers and element of the conversation operating system. When people feel they have power, they take it. Alice Walker said that the... and I always misquote her. I really should learn how to quote Alice Walker better, but "The way that most people give up their power is believing that they have none."
                                                      It's a real challenge. Everyone on the team if we're saying, "Wow, Brett's team, we want to have more deep interesting, useful, effective conversations, how might we do that?" Right? What are some things... what are some challenges we're seeing and what are some things that we would like to do? What are some things that we could try? What are some things that we're willing to try? Then we could start having a conversation about what experiments could we do? Week on week to say, "Oh, that was interesting." But there's some basics. I will indulge your desire for tips Brett. One of the things that... and a lot of us in this game talk about is really, really basic stuff and it's kind of embarrassingly basic. If you do a check in, a 30 second check in where everyone shares one thing, it sets the stage that everyone will share.
                                                      It's also just establishing that silence is okay. Third, active listening and maybe this is just on my mind because the email I sent out to my newsletter today was about active listening. To me, the 400, 600, 200 millisecond problem, this essential gap we have, I feel like everybody's got a different approach that when somebody speaks, we can either react, "I love that. I don't love that." Right? Or we can reflect. "Oh, what I heard was this, is that right?" Active listening is a really generous way of being like, "Wait so Brett, it sounds like you're saying this, is that right?" And you go, "Yes. Is there anything else?" "Oh yeah, this." It's deeply listening to somebody and really giving them space to share what they're going to share, but we get impatient.

Brett Harned:                                          Right.

Daniel Stillman:                                       So that's... I can tell you to do more active listening, but that's a way of doing. That's great, but our way of being is like we only got 30 minutes for this call. I worked with a global PR firm where they were talking about having better brainstorms, and I was like, "Well let's talk about what your average brainstorm is like." And they're like, "It's 30 minutes and there's 15 people." I'm like, "Oh my god." These are tough design constraints.

Brett Harned:                                          Yeah.

Daniel Stillman:                                       These are hard design constraints and I'm like, "Well we can do the classic everybody think alone or think together, and I recommend that people come with ideas and do prework." But that's a fantasy, right? The culture won't allow people to take 15 minutes to do some silent reflective brainstorming before they get into that 30 minutes, because they were in another 30 minute meeting before that 30 minute meeting.

Brett Harned:                                          Right, right.

Daniel Stillman:                                       So then we start thinking about design, right? Where it's like, "Well I'd like to design this meeting better," but there's all these other layers of design around it that have already been established for me by the culture, right? So-

Brett Harned:                                          Yeah.

Daniel Stillman:                                       I'm hemmed in. I have to design a 30 minute meeting that works as a self contained effective unit when people will be five minutes late to it.

Brett Harned:                                          And then... right, they're going to be five minutes late and then it feels like a lot of times, especially when the culture is not great. You get into that 30 minute meeting and it's derailed within the first five minutes by that person not showing up, or that person coming in and just completely doing different business than what was intended in the first place.

Daniel Stillman:                                       Right.

Brett Harned:                                          [crosstalk] met with challenges, right?

Daniel Stillman:                                       Right.

Brett Harned:                                          I mean it's-

Daniel Stillman:                                       Right, and this has to do with inviting the right people and doing the prework, and so I talk about conversation design. The conversation starts much earlier than we think and in the experience design framework that I know and love, the five E's of experience design; entice, enter, engage, exit and extend. I often like to teach people at least two layers of... there's many layers of designing a conversation, but if you think about the experience of the conversation, they are being enticed to enter and engage way, way upstream in the experience. It's not... the meeting doesn't start at 9:05 when everyone finally shows up. It started when you sent the invitation.

Brett Harned:                                          Right.

Daniel Stillman:                                       I think it started even before that, it started when you incepted the idea of the thing and decided what you thought was possible.

Brett Harned:                                          Interesting, and then I guess it precedes if there's an agenda, right? If there's a meeting agenda, then there's a little bit of an expectation around what the conversation is and how it will flow.

Daniel Stillman:                                       Yeah, and agendas are just even the... what I would call level zero of designing a meeting, right? Because most agendas are not realistic. They don't have bought for time and they don't have a process associated with them. How will you get those people to talk about that item? Will we... we'll just talk about it. "Well everybody, what do we think?" Then what happens? Somebody speaks first. Usually often, it's a guy. Whoever feels empowered to kick off the conversation is going to be somebody who thinks out loud, is extroverted and is habitually accustomed to feeling comfortable to sharing their thoughts. It's not going to be somebody who's introverted. It's not going to be somebody who's introverted. It's not going to be somebody who's further down the totem pole. It's not necessarily going to be the person who knows the most about the problem necessarily.
                                                      Whoever speaks first, we say, "So, we've got to solve this scheduling issues. What are some ideas?" Right? This is just brainstorm design, I mean there's tons of rules for brainstorms. The first one is just think quietly before... let everyone think their own thoughts before we think together. Amazing news flash, remote meetings are actually better for this stuff. Clarence Thomas, supreme court justice has asked more questions in the remote hearings of the Supreme Court in the last month than he has asked in the last five years.

Brett Harned:                                          Fascinating.

Daniel Stillman:                                       It is fascinating. So remote meetings because there's no table, this is so space to something that defines the conversation, right? It's like that classic image, I think maybe it's the first Batman movie where he's got a super duper long table and Michael Keaton as Bruce Wayne is all the way on one side of the table, and I think Kim Basinger? Kim Basinger is all the way on the other side of the table and they have to shout down to each other from... I don't know if you remember the movie, but-

Brett Harned:                                          I'm vaguely remembering this, yeah.

Daniel Stillman:                                       But you get the scene.

Brett Harned:                                          Yes, absolutely.

Daniel Stillman:                                       Dinner 20 feet apart on either end of the table. This is silly. When I go out with my fiance back when we could go out to restaurants, I actually loved sitting on the same side or caddy corner, I hate sitting opposite from them and she'd be like, "Wait, I want to look at you." I'm like, "Yeah, I want to be closer to you and I want to be looking at the same thing with you." You step into the room, the room says something about what's going to happen. So when we step into a digital space, there's no person at the head of the table who's going to kick things off. There's no order implied, which is hard but also allows Clarence Thomas to feel like he can contribute. So amazing.

Brett Harned:                                          It's interesting.

Daniel Stillman:                                       [crosstalk] good questions, yeah.

Brett Harned:                                          It allows space for people with different personality types. It's almost like a level set in some ways. [crosstalk]

Daniel Stillman:                                       Yeah, that's designing for different people.

Brett Harned:                                          Yeah.

Daniel Stillman:                                       Which we have to do all the time. We can't just design a product or a service or an experience, even though we say, "Oh, here's our ideal persona." The reality is we have three or four or five, or a broad swath of people and we have to just design these conversations that we're designing for the people who have to use them.

Brett Harned:                                          Right.

Daniel Stillman:                                       For the diversity of neurological and sociological abilities that people have so that we can get the best contributions.

Brett Harned:                                          Absolutely. I talk a little bit about that in some the classes at TeamGantt around communication tactics and just being aware of the people that you're working with and the communicator types you're working with and making adjustments for those people so that your communication lands well, and you and the team get what you need out of those people and your interactions to make sure that everything is running successfully. Because at the end of the day, if you're communicating well with someone, they're not going to deliver for you, right? Or they're not going to deliver what was expected if they don't really understand what that should be.

Daniel Stillman:                                       Right.

Brett Harned:                                          Along those lines, project managers specifically are always faced with difficult conversations.

Daniel Stillman:                                       Yes.

Brett Harned:                                          They could be surrounding things like a missed deadline, scope overages, or other interpersonal conflicts. I'm thinking that these are maybe topics that in the book, you refer to as the conversations we won't have.

Daniel Stillman:                                       Yeah.

Brett Harned:                                          You'll come to a tough situation, you have to address it and addressing it with that person is sometimes... it feels like it's the end of the world, right?

Daniel Stillman:                                       Yeah.

Brett Harned:                                          It's the last thing you want to do with your day, you don't want to further ruin your day, ruin that person's day. I'm wondering, what's your overall thinking or guidance around how to address those difficult conversations?

Daniel Stillman:                                       Yeah, it's really challenging and I'm coaching a design leader right now about some of the stuff, and one of the things I'm noticing in my conversation with him is that there's upstream versus downstream conversations. So he's up against somebody who's... when you're working on a complex project, it's harder to find what done is. If it's hard to know what done is, it's hard to know what halfway done is because this is a really complex challenge that they're solving for their organization, but he really wants to be able to trust this person to self manage because they're an intelligent person. He wants them to really be able to activate themselves.
                                                      So if he comes to them, he's starting to feel itchy and he's like, "Where are they with this?" Right? When you have that itchy feeling of where are they with this, this is his cadence coming in. This is like, "Brett, will you get to the point? Where are you going with this?" Question, right? Or I can say, "Oh, that's an interesting question Brett, tell me more." That's no patience versus anxiety. So he's got to manage himself, because if he comes to this person and says, "Hey, so we're halfway. Where are you with this?" It can actually make her recede in the conversation.

Brett Harned:                                          Right.

Daniel Stillman:                                       It's a very delicate thing to say, "Hey, where do you think we should be on this? Where would you like to be with this right now?" Now, we're in a conversation where we may not have established where we should be when we should be. So if you're a grade project manager or a product manager and you can define really good touch points and goal posts that everyone's actually aligned on. Then it's not so much of a hard conversation, because we've made agreements-

Brett Harned:                                          Right.

Daniel Stillman:                                       And everyone's bought into the agreements. So if you have [crosstalk]

Brett Harned:                                          Feeling of the personal attack out of it in some way, right?

Daniel Stillman:                                       Yeah. It's-

Brett Harned:                                          Because that's what... why people have a negative reaction to that kind of thing, because it is a personal question "Where are you on this?" There's an expectation on you about something and I need to know in this moment. That's how it feels when you get asked a simple question like that.

Daniel Stillman:                                       Yes, so this is where there's this polarity between asking and telling. That is really amazing and this polarity came to me, there's a book called Humble Inquiry by Edgar Shine and I'm going through it very slowly, but just think about that spectrum. Am I asking or am I telling? You're late on this deliverable versus where should we be with this deliverable? Where did you think we would be with this deliverable? What can we do to move this deliverable forward? How can we make sure this doesn't happen the next time? Right? This idea of humble inquiry I think is so important. This... I think we think like, "Oh, I have to have this difficult conversation because I need to let this person know that they're letting me down and they're screwing up."
                                                      But that's way, way down the stream question. We may not be there. You may feel like you're there-

Brett Harned:                                          Right.

Daniel Stillman:                                       But we may not be there yet and the idea is to really get to what's happening. What the real problems are. So there's another access. This is not Ed Shine's book. I think it's David Rock and Quiet Leadership talks about this. I use this now, it's asking versus telling and problem versus solution. This is another way to design your conversations, what quadrant am I playing in and why? It's totally fine to tell somebody what the problem is. If it's a real emergency, you're like, "Brett, your late with the deliverable. I need to know what's going on." Right? That's telling somebody what the problem is and then asking them, "What's going on?"
                                                      That's very different than saying, "Brett, we're late on the deliverable. You always do this." That's telling and... that's double telling and that's going to make somebody feel bad. Like, "Brett, you're late with the deliverable. You have too much on your plate right now, don't you?" Right? That's double telling again.

Brett Harned:                                          Right.

Daniel Stillman:                                       So I think the best... I mean, this is just me personally, and also, I'm an idealist and I don't have a real job, so don't take any advice from me, these are principles that people should live by, but I believe that we should be gentle with people and with each other. So asking people about the problems that they're facing is much more gentle than telling them about the problems that they're facing.

Brett Harned:                                          Right. It's also a little bit leading too, right? I mean, if you-

Daniel Stillman:                                       Yeah.

Brett Harned:                                          Say, "You're late with this thing. You've got too much work on your plate." That'-

Daniel Stillman:                                       Yeah.

Brett Harned:                                          Right away giving that person the excuse that they think you expect them to give, whether that's-

Daniel Stillman:                                       Yes.

Brett Harned:                                          The case or not.

Daniel Stillman:                                       Yeah, and it's leading in on the good way of leading, because really-

Brett Harned:                                          Right.

Daniel Stillman:                                       Asking somebody... really asking, double asking or playing gently in that quadrant is really leading somebody to be able to deliver more. "Hey, where did you... I thought we were going to be further along with this? What was your understanding?"

Brett Harned:                                          Right.

Daniel Stillman:                                       If you actually come humbly, "Hey look, we may not have established this clearly, but I'm feeling a little nervous." So this is where we have to... what's difficult about these conversations is that we don't want to make someone feel bad because we feel bad.

Brett Harned:                                          Right.

Daniel Stillman:                                       We need to be okay with, "I don't feel comfortable about this. Brett, I'm a little confused. I'm feeling conflicted. I honestly thought we'd be further along. I could be wrong." "No dude, you're right. I'm really sorry. Totally blew the pooch on that one."

Brett Harned:                                          Yeah.

Daniel Stillman:                                       "Okay cool." That's coming in not hot, right? That's coming in smooth and not for nothing, I think it's a more relational way of working.

Brett Harned:                                          Absolutely, and that's so important in project management too, right? When you show someone that you care about them as an individual, not just about their work product and checking up on where those things are, and not putting them on the spot in a negative-

Daniel Stillman:                                       Yeah.

Brett Harned:                                          Way, but showing them that you could have misunderstood something.

Daniel Stillman:                                       Yes.

Brett Harned:                                          Or you understand that they're behind and you just need to figure out why and how you can fix it. That builds trust and that long term-

Daniel Stillman:                                       Yeah.

Brett Harned:                                          Makes teamwork a lot easier.

Daniel Stillman:                                       Now, here's the thing, if you don't write things down that didn't happen, conversations have a place. Conversations have... our conversations happening in Skype right now. That's the interface for our conversation, and it's different than in Zoom, right?

Brett Harned:                                          Right.

Daniel Stillman:                                       I can send you emojis. I can send you a slow clap emoji, which is just hilarious.

Brett Harned:                                          Which you just did.

Daniel Stillman:                                       Which I just did, and that's a different... the affordances in design we talk about this, the affordances of this interface allow a different type of conversation to happen. Giving the conversation a good place to happen is so transformative. This is... I've had conversations about this. One of my first companies, I feel like we had constant battles of I wanted to be on Asana and somebody else wanted to be on Trello or Pipedrive, and somebody else just didn't want to use anything. We're three partners and we all wanted to use different tools to manage our process.

Brett Harned:                                          Right.

Daniel Stillman:                                       I'm not saying that this... Monday.com just go there, it'll solve all your problems. That's not true either, but if you... this is where in interaction design, we're like, "Oh, well here's the customer journey map. Here's where we started. Here's where we want to get to. Here's where we are now. Where should we be?" If you don't have a record of your agreements, it's really hard to hold them, hold people to them.

Brett Harned:                                          Yeah. Yeah, that's a really good point and I was actually going to ask you, how much of this, what we're talking about, to me, it applies still to that written conversation, of course I love the idea of having some kind of record of what's discussed in person, but the way that you would handle that written conversation be it over email, through your project management app, over Slack or chat.

Daniel Stillman:                                       Yeah, this is-

Brett Harned:                                          Gosh, it's like that's a whole other can of worms it feels like.

Daniel Stillman:                                       Yeah. Written conversations are conversations. My friend just sent a picture... and sorry for talking over where you were going to go with this.

Brett Harned:                                          No, you're good.

Daniel Stillman:                                       There was a picture of a bomb coming out of an air fighter, and on the bomb it said, "As per my previous email." I'll just let that joke soak in there. But that phrase is incendiary.

Brett Harned:                                          Yeah.

Daniel Stillman:                                       It's like, "As per my previous email, which you clearly didn't read-"

Brett Harned:                                          Right.

Daniel Stillman:                                       "You idiot."

Brett Harned:                                          Yeah, it's like you're reading between the lines. Yeah.

Daniel Stillman:                                       Yeah, we can all read between the lines and I had that with somebody last night, where they were like, "Oh, I can't come to the... I'm going to be 30 minutes late to the workshop tomorrow." It's like, "Oh, thanks for letting me know." That thanks for letting me know was a double entendre. She picked up both meetings. I was like-

Brett Harned:                                          Yeah.

Daniel Stillman:                                       "Thank you for letting me know." And thanks for letting me know. She's like, "Well I would have let you know in the morning." I'm like, "Yeah, I'm not even going to respond to that second email."

Brett Harned:                                          Yeah.

Daniel Stillman:                                       Because there's nothing to respond to.

Brett Harned:                                          Yeah, it's this thing too and I don't know if you've experienced this, but some people-

Daniel Stillman:                                       By the way, she's a wonderful person.

Brett Harned:                                          Yeah.

Daniel Stillman:                                       [crosstalk] listens to this.

Brett Harned:                                          [crosstalk]

Daniel Stillman:                                       But it's like I have my own operating system when it comes to when somebody shows up late to a workshop, I still have to manage myself.

Brett Harned:                                          Right.

Daniel Stillman:                                       So I'm like, "This trifling so and so has the nerve. Here I am pouring my guts out on the stage."

Brett Harned:                                          Right.

Daniel Stillman:                                       "And they are five minutes late?"

Brett Harned:                                          It also has to do with when that message hit you, and what you were doing and the context around that, right? I mean, it's very different from how you would have that conversation in person. You'd be like, "Oh, I'm sorry to hear that." You know?

Daniel Stillman:                                       Right.

Brett Harned:                                          Then she might tell you why and then it would be no big deal at all.

Daniel Stillman:                                       Right.

Brett Harned:                                          But I think the thing about written communication too is that some people just feel like when they're at work, they have to use formal language that feels like business language, and this is the way that I should communicate to you. It often feels terse or dry, and maybe just a little unfriendly.

Daniel Stillman:                                       Yeah, yeah.

Brett Harned:                                          So to me, I feel like that's where you can definitely... people make some adjustments and read back through an email or a message and say, "Is this how I would-"

Daniel Stillman:                                       Yes.

Brett Harned:                                          "actually say this thing in person?" If it's not-

Daniel Stillman:                                       Yeah.

Brett Harned:                                          Then rewrite it or edit it.

Daniel Stillman:                                       Yeah and take a paragraph out. I just read a series of posts. They were images of whiteboard captures from inside Amazon of how they speak, and so they were like, "Here the three Amazon answers to a question. Yes. No. Yes. I don't... yes. No. I don't know a number, or I'll find out." I forget what it... there was extremely limited... it doesn't... will this work? Yes. No. I don't know. Here's when I'll find out, or percent clarity. It was just like, "Wow, they're really clarifying their culture."

Brett Harned:                                          Right.

Daniel Stillman:                                       It's not like, "Well it might." No, it's either yes or no, or you don't know. You'll find out when, or here's a probability. That's it.

Brett Harned:                                          A bit robotic.

Daniel Stillman:                                       Well I mean yes, but it kind of... to me, it's funny, my thing was like, "Oh, isn't that simplifying? Isn't that useful?" They don't want somebody to have weasel words or hedge language like, "Well, we think this. We might that." It's not about convincing me. It's like, "Do you have evidence or not?" Let's just be clean about it.

Brett Harned:                                          Right. Yeah, I guess it sets an expectation around how you would operate or communicate about your work or decisions around your work, and that's certainly helpful.

Daniel Stillman:                                       Yeah, yeah.

Brett Harned:                                          So we're coming up on time and I appreciate you-

Daniel Stillman:                                       Yeah.

Brett Harned:                                          So much. This has been a fun conversation for me.

Daniel Stillman:                                       Thank you, me too.

Brett Harned:                                          So as you know, the show is called Time Limit. At the end of every episode, I just ask my interviewees if they might be able to offer a couple of tips, or even just a scenario where you related to something. So in keeping with the theme of having limits on time and resources, I'm wondering if you have any conversation, or facilitation tips or tactics that our listeners can utilize when they're stretched for time and they just... project managers a lot of times just need to get decisions made. They need to help push a team to get progress and get work done. Sometimes really quickly with not-

Daniel Stillman:                                       Yes.

Brett Harned:                                          Enough resources.

Daniel Stillman:                                       Yeah.

Brett Harned:                                          With less debate and less conversation.

Daniel Stillman:                                       Yes.

Brett Harned:                                          Are there any things that you might recommend that conversationally help to push those things along?

Daniel Stillman:                                       Yes. So one of my favorite tools as a facilitator is lying about time. Certainly in a workshop setting, I love telling people that they have five minutes for a task, when it's an absurd amount of time for the task. It's like, "Let's put together this thing in five minutes." And then letting people sweat it out, and then when there's a minute left, ask them if they need an extra minute. Everyone will need an extra minute because if five minutes isn't enough time, four minutes is definitely not enough time. So this is one of the reasons why I actually don't like time timers, because they force you to be honest about time. So if I am the time keeper, and I'm the time friend, I can say, "All right everybody, so let's write down five solutions that we think are really going to blah, blah, blah this blah, blah, blah by blah, blah, blah." They go, "Okay cool."
                                                      So we're already giving the time limit, right? Time limits and time boxing, time constraints, we'll get people to generate five ideas in five minutes is a lot. So then I lie. Four minutes, I give them that extra minute and they're like, "Oh, that's great. Thank you. I feel so much more relaxed with that extra minute." So I'm just giving them back a minute that was theirs anyway. Then I tell them at the end, towards the end maybe with the last 30 seconds I'm like, "If you only have two or three, that's fine." Then I say, "Actually, just share your top two ideas." And they're like, "Oh, okay cool." So they look at their five ideas and they're like, "Well these are the two that are really the best."
                                                      Then we just see everybody's ideas. I mean, again, this is not revolutionary facilitation mechanics but lying about time, stretching time, reducing what people... getting people to already edit what they're sharing with the group. So getting people to generate more and then giving only the best. When there's a big decision to be made, I like getting everyone to write down what they think. Especially if we think that there's a big gap between where we are and where we need to be. Put those ideas up there on the wall, it can be a virtual wall, or a digital light board wall, or a white board wall. But put it up there and for me, I think that gives us a sense of where we are. What's the distance between where we are now and where we need to be? I think a lot-

Brett Harned:                                          I like that.

Daniel Stillman:                                       I think people are often afraid to do that because "Well what if we are further apart than I want us to be?" Right? But what I found is seeing the distance is always better than not seeing the distance, right? Knowing the gap is better than guessing at the gap, and once we know the distance between everybody, we start to move our opinions around on the wall and we say, "Oh, we've got these three opinions." We can say to the person in the minority, "How do you feel? Can you agree?" This is designing how we decide, right? Deciding about how we decide. What does it mean for one person to disagree? Can you disagree and commit? That's the classic phrase. Can you disagree and commit?
                                                      Or do we need to get evidence about these two or three different pathways, but now we can actually have the conversation about what's next, and before, we were just nervous.

Brett Harned:                                          Yeah, those are really great tips. I think a lot of times, folks get into a meeting where they might be the de facto facilitator and just think, "Oh, we're just going to have this conversation." But I think with what you just outlined, if that person remembers what the goal is for that meeting, and they're driving at meeting those goals and whether it's getting people to write things out and discussing them as a group, or if it's doing an exercise and getting the top couple ideas out of someone, that's going to basically drive a more productive conversation.

Daniel Stillman:                                       Absolutely.

Brett Harned:                                          And it'll save you time from spinning wheels and having a conversation where you go round and round and round in the room. You just-

Daniel Stillman:                                       Yes.

Brett Harned:                                          Go directly into getting the ideas out and having a more productive conversation right away.

Daniel Stillman:                                       Yeah, because otherwise it can be a ping pong match, and now all we have is let's all sit around the fire.

Brett Harned:                                          Right.

Daniel Stillman:                                       Of the ideas that [crosstalk]

Brett Harned:                                          Or where are we really far apart? Yeah, that's awesome. Well cool.

Daniel Stillman:                                       If everybody's opinion matters, which it may not.

Brett Harned:                                          Right. Depending on your meeting and the attendees.

Daniel Stillman:                                       Yeah.

Brett Harned:                                          Well Daniel, thank you so much for joining me on Time Limit. Again, I hope everyone checks out Good Talk. Congratulations on that. I can't wait to dig in further, but thanks for being here. Really appreciate it.

Daniel Stillman:                                       Brett, thank you so much for making it happen. I really appreciate it. I think conversations are how we build our lives, and if we can do it better, the world can be a better place. True story. So I hope people can take some stuff from this and make a difference in their work.

Brett Harned:                                          Absolutely. I think they will. Thanks again.

Daniel Stillman:                                       Thank you brother.

Brett Harned:                                          All right folks. That's all for that conversation with Daniel Stillman. I hope you took away as much as I did from that talk, especially that last quote. Really good stuff. So I think you should check out Daniel's book, Good Talk on Amazon and check out his site, theconversationfactory,com for more resources and even Daniel's podcast. If you have a moment to rate our show, or leave a review where you listen to your podcasts, we'd really greatly appreciate it. Thanks so much for joining me, and I'll see you back here for our next episode.

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