Oct. 29, 2024

352 Agile Conversations: Transform Your Conversations, Transform Your Culture with Douglas Squirrel | Partnering Leadership Global Thought Leader

352 Agile Conversations: Transform Your Conversations, Transform Your Culture with Douglas Squirrel | Partnering Leadership Global Thought Leader

In this episode of Partnering Leadership, Mahan Tavakoli is joined by Douglas Squirrel, co-author of *Agile Conversations*, a transformative book that dives deep into the art of having productive conversations in organizations. Douglas Squirrel, a seasoned technology leader and coach, shares his journey from struggling to communicate effectively with non-technical leaders to discovering frameworks that have radically changed how teams collaborate and make decisions. His passion for helping organizations unlock their potential through better conversations is palpable, and the strategies he presents are both practical and actionable.


At the core of the conversation is the idea that many leadership and business challenges stem from poor communication, especially when stakes are high. Douglas introduces the concept of "model two" reasoning, a method of shifting from defensive, closed-off thinking to open, curiosity-driven conversations. Throughout the episode, Squirrel outlines how leaders can build trust, foster collaboration, and make better decisions by focusing on the quality of their interactions, not just the content of their discussions.


Leaders in fast-paced industries, especially those leading technology or innovation-driven teams, will find Squirrel’s insights particularly relevant. His approach to improving communication is likened to practicing a sport—it requires effort and repetition, but the benefits are immense. From navigating difficult conversations to breaking down silos between departments, Douglas illustrates how leaders can transform the culture of their teams by mastering the art of meaningful conversations.


Whether you're a CEO striving to foster better communication within your leadership team or a senior executive looking for ways to enhance cross-functional collaboration, this episode is packed with practical wisdom. Douglas Squirrel's methods have been honed through years of experience in leading technology teams, but his insights apply to anyone seeking to elevate their leadership effectiveness through the power of dialogue. Don’t miss this episode—it could very well change the way you approach conversations in your organization.


Actionable Takeaways:

  • Hear how to overcome communication barriers in cross-functional teams by focusing less on technical jargon and more on relationship-building.
  • You'll learn why defensive reasoning is holding your team back and how to shift toward curiosity-driven conversations that foster collaboration.
  • Discover how the right kind of questioning can unlock hidden insights that may be missing from your leadership discussions.
  • Explore why ‘disagree and commit’ can sometimes be dangerous and how true alignment comes from genuine dialogue.
  • Hear how to use 'back-briefing' to ensure accountability while giving your teams the freedom to innovate and solve problems their way.
  • Find out why learning to have better conversations is like practicing a sport and why it’s essential for long-term leadership success.
  • Get practical tips for identifying when a trust conversation is necessary to build stronger, more collaborative teams.
  • Uncover the biggest mistake leaders make when trying to include everyone in decision-making and how to avoid it.


Connect with the Douglas Squirrel

Douglas Squirrel Website    

Douglas Squirrel LinkedIn

Connect with Mahan Tavakoli:

Mahan Tavakoli Website

Mahan Tavakoli on LinkedIn

Partnering Leadership Website


***DISCLAIMER: Please note that the following AI-generated transcript may not be 100% accurate and could contain misspellings or errors.***

[00:00:00] Mahan Tavakoli: Douglas squirrel. Welcome to partnering leadership. I am thrilled to have you in this conversation with me. Likewise, Mahan, wonderful to be here. I can't wait to talk about some of your thoughts on agile conversations,, because having better conversations is essential.

[00:00:16] And I find is one of the barriers that gets in the way of people collaborating effectively and doing great things in organizations. But before we get to that. We'd love to know a little bit more about you, Douglas. Whereabouts did you grow up and how did your upbringing impact the kind of person you've become?

[00:00:34] Douglas Squirrel: As you can tell from my accent I'm English. No, you can't tell that from my accent. There's a long history behind why that happened, but as I was telling you before, Mahan, I'm English, but with this funny way of talking, and it doesn't help me on the cricket pitch. I can tell you that when umpire's whites, I have respect until I open my mouth, and then I have to get the respect back again.

[00:00:55] But I live in Frogholt, which is a tiny village that nobody's ever heard of. And the thing that's close to Frogholt that you wouldn't know about is the Channel Tunnel, which is 500 meters that way. So that's where I live. I get to hang out here and go around the world on my screen. So I get to talk to people all around the world in Australia and Africa, in Asia, you name it.

[00:01:14] And I help them with their technology and their communication with technology people. And that's a load of fun. 

[00:01:20] Technology people, Douglas have not necessarily been known as the most effective at communication. So how did those two.

[00:01:29] Mahan Tavakoli: Come 

[00:01:29] Douglas Squirrel: together for you. What happened to me was that I was trying to lead technology teams and I kept running up against barriers and the barriers would be things like the CFO not wanting to fund something because she didn't understand it. Or the head of marketing saying why can't you just send a million emails every morning?

[00:01:48] And I'd say, it just doesn't work that way. There's this technical challenge. And she didn't care. She knew she had a list of a million people. She wanted to send the emails to all of them. There was emails they wanted, but why couldn't I actually deliver? And explaining that was more and more difficult for me.

[00:02:03] I found that the techno babble got in the way, but also my relationships got in the way. So then I discovered with the help of some very bright folks. Old dusty papers from the 1970s by a guy called Chris Argyris, and he had discovered techniques that you can use, that anyone can use, to improve their conversations.

[00:02:24] It's a skill like playing tennis, and like playing tennis, you won't be good at it to start, You'll knock the ball down, you'll hit it out of the ground, you'll do other things, but as you practice more and more, you will actually get good at doing things like asking an engineer a tough question about why they can't meet a deadline, or explaining to someone in the marketing department or in finance why a technical request is impossible or difficult or too expensive.

[00:02:49] And having those kinds of conversations more effectively, you can imagine makes the whole organization more profitable. So there were these techniques buried in these books. And I said, my God, this is stuff you can just practice. We engineers, we love this stuff. We like stuff that has steps and are very clearly defined and we can figure out how to do it.

[00:03:07] And we can do step one and step two. So then I wrote Agile Conversations with my friend Jeffrey Frederick. That's this book here, which I'm happy to send to your listeners and your viewers, by the way. Agile Conversations. And that book is all about how to have conversations with a team that's following Agile principles.

[00:03:25] It's trying to build software better. And to learn what customers actually want and to satisfy what they need, rather than doing what the engineers think is cool. And the fact that we can accomplish that by following some steps, by practicing, like practicing a game of tennis. It's a really tremendous discovery that I'm sharing with the world.

[00:03:45] Mahan Tavakoli: I couldn't agree with you more, Douglas, in that a lot of times there are some things that are most critical in leadership, relationships, collaboration, and organizations that we spend the least amount of time and effort on learning what are the best approaches to it and then systemically implementing those.

[00:04:05] Which is why, even though you gave examples. Specifically related to some techies and or software organizations. I find your insights applicable to teams collaborating with each other and communicating effectively. Now, you mentioned Chris Argyris  very good, not many people managed 

[00:04:27] Douglas Squirrel: to pronounce it right.

[00:04:28] Yes. He had a hard to pronounce surname. 

[00:04:30] Mahan Tavakoli: He had model one and model two theories. Would love for you to help the audience understand how we can not engage in model one defensive reasoning, but shift more toward model two productive reasoning. I find so often we get pretty.

[00:04:50] Defensive, especially when it's high stakes conversations. 

[00:04:55] Douglas Squirrel: That's exactly when the defensiveness kicks in because it matters. And if you ask people. Hey, how should we decide where to go to lunch? You'd ask for people's input, and you might share your own view. You might say, Hey, wait, I'm a vegetarian or I don't like fish or something like that. And that might cause the group to make a slightly different decision. We all know that's a good way to make a decision to get all the information inputted so that we can consider it and figure out what to do.

[00:05:21] The problem is when it really matters, that's when we don't do it. So if you think back to the last really tough decision, maybe you had to decide to change your podcast or you wanted to change your marketing strategy or something like that. You were probably pretty sure about what you wanted to do, and you probably didn't do as much consultation.

[00:05:40] If you did good for you, that means you've been practicing, but most people tend to say normally we make our decisions with this collaborative way, like for lunch. But, strategy for the company, deciding to enter a new country, we look to somebody to decide that for us. And we don't include all the information, but the problem is there's information that's out there that could change your decision in a positive way.

[00:06:03] And that's what model two reasoning is to help you discover, something that I do sometimes with groups is I'll say, Hey, everybody just as a part of our group today what I've done is I've planned for all of us to have ice cream. If we manage to discover the secret word that I've told one person in the group, I won't tell you who it is or what the secret word is, but if somebody says the secret word, everybody gets ice cream.

[00:06:26] And then after a few seconds, I say, now, actually, I just lied to you. There's no ice cream. Nobody's getting any. But do consider what you were thinking when you were trying to discover, how are we going to guess the secret word? How are we going to guess the secret information that somebody has? And what I want you to do is all that stuff that would have got you ice cream.

[00:06:44] Because. There's secret information hidden in your meetings, in your junior people, in your team, people who are from another country, people who have different backgrounds. And what happens so often is we get so certain that we say, I know how to do this. We're following my lead. This is how we're going to do it.

[00:07:01] And we never get the additional information. That's the model one thinking. That's the defensive reason. I got to get it right. It really matters now. So I'm going to think about how to win, how to get my way, how to make sure we do the right thing. Instead of thinking, how could I be surprised?

[00:07:18] How can I learn something I'm not aware of? And how could I change my mind? And if you can get into that second model two non defensive reasoning, and there are tricks for doing that. They're in the book and I'm happy to talk more about them here. Then you get much more information and you might make the same decision, but really well informed.

[00:07:36] You'd say, Oh man, this isn't going to work in Germany. We'd better change it this way because I've listened to somebody from Germany. I haven't done what they wanted to do, but I've incorporated their ideas. That's the sort of thing that you need to do. I 

[00:07:49] Mahan Tavakoli: love the example that you use there, Douglas, because when I see leaders interacting with their teams, they do engage in the questioning.

[00:07:59] They do feel like they're involving people, but the higher the stakes go, the less likely they are to engage in that. So part of what you're saying is model two reasoning becomes even more important as the stakes go up 

[00:08:16]  You got it? How can we do that, Douglas? When it's high stakes, I feel like, okay, I know what we need to do. I'm less likely to ask questions from deep curiosity. 

[00:08:29] Douglas Squirrel: Exactly. And that's a key point. I just want to pull that one up on, because a lot of folks may be thinking.

[00:08:34] I ask questions. I say, all right, everybody tell me what you think. I'm really interested. Please let me know your thoughts. If you have any, just write to me here and they hear nothing. And then they go ahead. That's very dangerous because what they've done there is a kind of mild form of a leading question.

[00:08:50] And this is what lawyers do. Now, if you're in a court of law, and we were all watching a trial a few months ago, right? Where some guys were really pushing on each other. They were really making, trying to get a victory there. And when you do that, what you tend to do is stuff like this. Mahan, you were outside the bank.

[00:09:05] You were revving the motor of your car you were watching the bank door carefully, and you were waiting for the robbers to come out so you could drive the getaway car, weren't you? I'm trying to box you in. I'm trying to force you to give a certain kind of answer. It's very difficult for you to say, yeah, actually, I was waiting for my mother, who was in the next building, and, I really wanted to get her to her medical appointment.

[00:09:26] It's hard for me to give that answer, if you're asking me that kind of vigorous, leading, directing question. Now, the example you gave is fantastic because the leader there, the executive has said, here's where we're going now. Now I'd like some example. I'd like some other ideas, please let me know, but it doesn't sound very genuine.

[00:09:44] The leader needs to do much more to give everybody in the organization. The idea that the leader would like to change his or her mind. I would like to be surprised. I'd like to find out I'm wrong. And there's an extra award. It's like the ice cream. I love to find out there's something that I have got wrong and I'd like to change what I'm doing.

[00:10:02] And you have to really overemphasize that because your position makes it sound like you're asking the leading question, are you, weren't you driving the car, aren't you aren't you the getaway driver? And when those leading questions shut down the conversation so quickly. Now, your question was, how do we do that?

[00:10:18] How do we get better at that? The thing is that you can practice, and it's the same thing as tennis. Argyris said, it takes you about the same amount of time to become pretty good at this as it takes to learn to be a mediocre tennis player. And that's a few months. It's not a trivial exercise, but the book is full of specific exercises that you can do in real situations.

[00:10:40] And they start with writing down your conversation and you write it down in a specific form. You look for certain characteristics, you score yourself, and then you revise. You asked about the four Rs. That's my technique. For learning quickly and revising what you're doing so that you can practice it again.

[00:10:59] And you're going to be bad at it. Just like in tennis, right? You're going to knock the ball out of the court. You're going to do things wrong, but that's okay because you have many more conversations to come and you can keep practicing when you get good at it. What you wind up with is a situation where you go into a sit a strand of strategy, planning session, or a decision of some kind.

[00:11:18] And you often walk out with a completely different decision than you thought you were going to make, and you're much happier with it, because you have managed to ask those genuine questions, not the leading questions, and you've learned something that's surprising. Plus, the people in the group say, She really listened to me.

[00:11:35] She really got it. And even though we didn't do the thing I wanted to, I understand why and we're going to see how that works out. So you get much more commitment and much more information. So , doing that level of practice really pays off. 

[00:11:49] Mahan Tavakoli: It really does.

[00:11:50] And you emphasize quite a bit, the importance of the relationship and that trust building in the organization. If nothing else, it also does that well. When genuinely approached. Now, I wonder Douglas, I'm sure you've also experimented with these. I have with some of my clients with using generative AI would love to get your thoughts on how that can be used as a neutral observer that can give us feedback. 

[00:12:18] Douglas Squirrel: So the thing I always warn people about AI is you never want to let the robot on stage because the robot is incredibly boring. So I would not want you've got a little recorder here that's recording us, I'm sure it's going to help you, but if it started piping up and saying, Hey squirrel, I've got a question for you, I'd be very worried.

[00:12:35] Not because it'll make stuff up. But because it's so darn boring. And it'll say things that just don't make any, aren't relevant and aren't helpful. That we just haven't gotten to the advanced stage where a machine can ask interesting questions like you are Mahan. So your job is safe. Don't worry.

[00:12:52] But where it's tremendous, don't worry, everything's safe. But here's the key thing. One thing we've all learned about these AI tools is they love to make stuff up. That's a good thing. used correctly. Because what no one seems to have noticed, except for a few folks, there's character. ai and a few others, who have tools for actually using it as a troop of actors.

[00:13:14] Not just one actor, but multiple actors. And you can say, I'd like you to be, you generative AI, you cat GPT, to be my tough boss who really doesn't like me and who wants to kill my project because it costs too much. And I want you to object as much as you can. And I'd also like you to be my kind of useless and timid subordinate.

[00:13:36] Who never backs me up and who doesn't answer questions very directly. And I want to have a conversation with those two people and it'll do that. And it'll make up details and it'll do things, but that's what you want. You want it to surprise you as you are practicing. You can think of it like a tennis partner not just a tennis machine that's spitting balls to you, that is always coming the same way, but a tennis pro who's in there, trying different stuff and runs to the baseline, runs to the net.

[00:14:00] Does things you don't expect, and that's what you need to practice. So I have seen good results from people using it as an actor or a group of actors to simulate situations where you want to improve your conversations. That's where I think it really shines. That's a 

[00:14:15] Mahan Tavakoli: great use case. And I appreciate that.

[00:14:15] Now you were talking about the leader. Engaging and asking the questions getting people to come up with their thoughts, share their thoughts, that openness. One of the questions that I often get, Douglas, whether it's from clients and I've gotten this from podcast listeners as well, is the concept of disagree and commit does consensus and everyone being on board matter?

[00:14:41] Douglas Squirrel: . So there's a whole technique in I think it's chapter five of the book. Which is all about joint design.

[00:14:46] And that's a process in which you ask these genuine questions in a structured way, you make sure the right people are in the room and you make sure that you're getting all the information. So nobody, your goal in the meeting is to make, or the session or whatever you're doing is to make sure that nobody leaves the room saying I wasn't heard.

[00:15:03] Nobody says they just didn't listen to me. My ideas weren't on the table. And once you achieve that and you set a time box, you say, we're going to have an hour in which we're going to get this done. At the end of that, you have a decision process. It doesn't have to be you deciding. It could be you kick it upstairs to somebody else.

[00:15:19] It could be you have two people in the room who come to a decision together, but you have some agreed beforehand before everybody gets started. We say, this is how we're going to make the decision after listening very carefully after getting all the input. And you have to be genuine about that.

[00:15:33] And in general, when I do that I stand up in front of people without a whiteboard and I have a rubber and eraser in one hand and a pen in the other, and I'm like rubbing things out and putting other things in and I'm making sure that I'm changing what's happening, not when I don't agree and I say, hang on, all right, I recognize that would be good, but we're not ready to go into China yet.

[00:15:51] So that's off the table, but I might say, but that means we should pay more attention to Asia. We should be doing more research there. Let me add that. And then I'm bringing in their ideas. After I'm done doing that, when the timer goes off, then it's time to exercise the decision making rule, and when you get that clarity, you get that input that comes in, plus the clarity of the decision, you don't have to have disagree and commit, which I find is dangerous.

[00:16:19] It leads to that kind of leading question, closing down model one thinking. Because what you say to people is look, you just got to salute at some point. All right. We've gone through the motions of listening and paying attention and so on, but we didn't really. And so now you need to just go along with whatever the group says.

[00:16:36] That's not a very good idea. That doesn't get real commitment. What you get is grudging commitment and people undermining and trying to do something else and so on. You don't have real alignment. And so what I'd much prefer is to have this kind of analysis upfront with the group and joint design that allows them to be included.

[00:16:54] And then saying look, can we all try this for a bit? When I did did this recently, what I said to the whole group was, look, we're going to try this for two weeks. And if it doesn't work, I will buy everybody a beer. Is everybody willing to try it on that basis? Cause at least you'll get a beer.

[00:17:10] Guess what? I didn't have to buy anybody a beer. It worked, but if it had, I would have been happy to buy a beer and say, okay, great. I was wrong. The decision we made didn't work. Let's try something else. And I'm showing there that I'm willing to be wrong. And when you do that, you give a slightly different message to disagree and commit, which is, look, I'm right anyway.

[00:17:28] Just do what I say. And that, as we know, doesn't actually work out very well as a leader. 

[00:17:35] I hear that there is a clarity that is communicated ahead of time about how the decision making process works.

[00:17:43] Douglas Squirrel: Yes, absolutely. You have to clarify the decision making rule before you start. If you just come along at the end and say, Oh, by the way, I'm going to make the decision, people feel betrayed. They say, wait, you were listening to me. And then you made the decision. If you say at the beginning, I'm going to listen real carefully.

[00:17:55] And then Mahan and I are going to decide they know what's coming. 

[00:18:00] Mahan Tavakoli: And then there is the value in people feeling like they have been heard in the process within the context that you have preset for them. Sometimes what I find, Douglas, is that is not clearly communicated ahead of time, which then causes frustration afterwards, where people feel like even though they listened to me, they didn't do what I wanted them to do.

[00:18:23] Douglas Squirrel: Exactly. And that's where the genuine listening, the genuine questions is really super important and you have to really mean it. So this is a real mindset shift for you as a leader, but it's not that huge because if you think of it, it's not, it's huge psychologically, but in business terms, it's actually really smart.

[00:18:41] Because typically, just like that secret word example with the ice cream, there is secret information. There's somebody here who knows this isn't going to work on the on the mobile app. We're going to be able to take the new type of payments on web, but on apps, there's going to be a big problem.

[00:18:57] And somebody from that department knows that information. I assume you've brought them into the discussion, but if you're asking those leading questions, if you're promoting your point of view, if you're really pushing for alignment before you've heard everyone, then you're missing the opportunity to learn something surprising that could really change your strategy.

[00:19:16] Hey, hang on a second. We have to roll this out differently. We aren't going to be able to shift to the new model and reduce our transaction costs in this way. Or at least not on mobile, and mobile is 60 percent of our income. Wait a minute, I've learned something that's going to change my strategy.

[00:19:32] Not change it completely, I'm not going to abandon my goal, but I might shift how I do it, how I roll it out, where I start. And that kind of input, People tell me always that they want it, and they say, I just don't know how to get it, right? I tell people, I align with them, I do a lot of work, I do everything one on one, and then I don't get the commitment, and I don't get the information.

[00:19:53] I'm surprised, six months later, when the software isn't ready, when the operational tools aren't there, when the rollout doesn't work in the new country. And the reason is they missed the joint design at the beginning. They didn't ask the genuine questions. Guess what? They didn't get genuine answers.

[00:20:08] Mahan Tavakoli:  If you don't set up the process ahead of time, you are not going to get that engagement, those conversations that are necessary for that end.

[00:20:17] Douglas Squirrel: You know what I was just telling my community today, I send weekly emails and so on, so I was sending one out today and I was telling them that one of the things you should be looking for as a metric for yourself is to is what was I surprised by this week? What happened in the last week? Your listeners can ask themselves this question.

[00:20:33] What happened in the last week that was really surprising? It was new information. I thought X and I found out why I believe that we were on track for this, but it turns out we weren't. What was surprising to you? If you aren't learning surprising things every single week, you're not asking enough genuine questions.

[00:20:50] And that is a huge risk to your business. 

[00:20:53] Mahan Tavakoli: It really is. And another thing, as you were talking about this, Douglas, I was reflecting on is the fact that in addition to helping people feel heard the business climate, all of organizations that I see have become a lot more complex. So while 20, 30, 40 years ago, one or two or a couple of individuals could have had an understanding of the full scope of a business that no longer exists.

[00:21:24] So it's not just listening to people. So they feel heard that is critical for the success of the team and organization moving into the future. 

[00:21:34] Douglas Squirrel: Exactly. Let's take a real example. So I don't know if you know what's happening in space right now. So our old friends at Boeing, they've had a few problems with their airplanes. They also make spaceships. And they've made a spaceship and they launched it with some astronauts and they sent them to the space station.

[00:21:47] Now, I don't think they're back yet. But they were having enormous trouble and by the time people listen to this, I suspect they'll be back. But the problem is that they've launched it, but they didn't notice that it was going to be hard to return. There are problems with it. So it might blow up when it comes back.

[00:22:02] And so they're stuck on the space station. They went for a week. It's like Gilligan's Island. They went for a weekend there for years. So we don't know how long they're going to be there. But there were engineers at Boeing. Just like in the door falling off the airplane and so on. In those cases, there were engineers who knew this might be a problem and somebody didn't listen to them.

[00:22:21] And so you get burnt by this kind of stuff. You launch the new product or you launch the spaceship and you think everything's on track. It's great. All my indicators here are green across the board. You get it to where it's supposed to go and you say, Oh, wait a minute. This isn't working out so good.

[00:22:38] And the fault there is that you didn't have the right conversation at the beginning. And there are hundreds of examples like this of every kind of crash in the world, every kind of disaster. You can trace it back in part, at least to somebody who didn't have enough of a genuine conversation, didn't ask enough genuine questions to find out, hey, hang on, there's a risk here we haven't mitigated.

[00:22:59] Mahan Tavakoli: That is incredible, Douglas, because from the space shuttle Challenger, which has been used as an example there have consistently been these examples. But what I challenge my audience to think about is the fact that the vast majority of leaders. I interact with nod and would agree that this is a problem in other organizations.

[00:23:23] And they read about Boeing and they're like, Oh, wow. Can't believe they didn't ask. And they didn't listen. Good job. We do it. Oh, I'm so relieved. That's what we do. Yep. I'm not part of that crew. The challenge is. Assume that in all of our organizations, we can do a much better job having these conversations in order to help people feel safe enough to contribute and engage and share their thoughts.

[00:23:53] Douglas Squirrel: Exactly. Let me give your listeners a little exercise that they can do. Now, if somebody's driving or something, I don't want you to do this, pull over or do it when you get where you're going. But take out a piece of paper. It's really important. There's some psychological reasons for this.

[00:24:04] Take out an actual physical piece of paper and write on it a difficult conversation you had. You were pushing the tech team to try something new. You wanted the marketing team to reduce their costs, whatever it was you were asking people to do. And write down on one side of the paper what you actually said and what the other person said, as best you can remember.

[00:24:22] Doesn't matter if you don't have it perfect. And on the left hand side, write down what you were thinking. By the way, Mahan, are you telepathic? 

[00:24:29] Mahan Tavakoli: Not yet. Not yet. Okay, if you develop telepathy, 

[00:24:32] Douglas Squirrel: please let me know first. I have some great business ideas for you. I'm working on it. So I bet our listeners are not telepathic either.

[00:24:38] So you're not allowed to write down what the other person was thinking. So you only can write down what you were thinking. And if you write this down in this nice format with the stuff on the right that you said and what you were thinking on the left, it gives you a huge insight into how that conversation went.

[00:24:51] You just need a few sentences. You don't need the whole You know, hour long chat, but just get a few of the sentences that give you a sense of what happened, the most difficult part. And the thing I want listeners to do is the most simple exercise. We do a lot of this in the book, but the most simple exercise you can do is just to circle all the question marks.

[00:25:08] And what you often find is either there are no question marks at all. It's all, Mahan's an idiot, I don't know why he's doing this. Mahan, you're an idiot, why aren't you doing this? That's all the way down, and nobody ever asks a question. Or, all the questions are on the left hand side. You're thinking, why is Mahan doing this?

[00:25:23] Who's told him? Where has this come from? You say, Mahan, this is a terrible idea, you gotta stop this. You never ask the question. And when you do that exercise, you discover how you're a little bit more like Boeing than you think you are. And a little bit more like the people who unfortunately blew up the spatial challenger.

[00:25:40] Because those folks didn't ask enough genuine questions of their engineers to find out the secret information that they had. And nobody got any ice cream, I can tell you that for sure. The same thing is happening in your listeners organizations. And I predict that if they do this exercise, they'll be as shocked as everyone is that I take through it, which is, I'm not asking enough questions.

[00:25:59] And that simple change to increase the number of question marks in your record can immediately make a huge difference. There's lots more you can do, but it's that kind of exercise that can hugely change how your conversations work, how those of your team work, how those in your extended organization and your partners and so on.

[00:26:16] How could those people align better? They could start by asking questions. 

[00:26:21] Mahan Tavakoli: That's an outstanding exercise. And I will definitely do it myself as well. Douglas, I appreciate you sharing that. Now in your book, you also go through the five conversations. I love the way you break down the different types of conversations that we have trust conversation, fear, conversation, why conversation.

[00:26:42] Commitment conversation and accountability conversation. Congratulations. Excellent. You got them all five. I'm not sure I could do that. . I would love to touch on a couple of them.

[00:26:52] What are some key signs that tell you that a trust conversation is necessary in a team, from 

[00:26:59] Douglas Squirrel: your perspective? One of the key ones is that the people are talking at cross purposes. I'm for people who aren't viewing me I'm making my hands go past each other. It's two ships passing in the night, and they're not using the same language.

[00:27:11] I had a great example of this. I'm going to do an event on it in a couple weeks, where two people in an organization I was coaching kept saying, we got to expand. We have to do our expansion. We have to expand in this area. And they kept saying, we have to expand here and we have to expand there. They kept saying, we just have to do it this way.

[00:27:28] And they were different. And then I got them together and I said, you guys have to have a conversation about this expansion question. Guess what happened? They figured out they were talking about the same thing. They violently agreed that they should expand in the same way, but they weren't, they hadn't built enough trust to have a common language.

[00:27:45] Now, people say things like trust is being predictable or trust is having a faith in the other person and believing they have good intentions. That stuff's easy to describe. But if you are using the same language, if you have what Jeffrey and I call a shared story, And you're able to talk in the language of the other person, then you won't have this kind of misunderstanding.

[00:28:05] You won't have the ships passing in the night, and you'll be able to predict the other person's behavior. You'll be able to say, I understand why Mahan does this. I don't necessarily agree. I think Mahan's wrong about this part. But man, it is really unsightful that he takes it this way. For example, you might have engineers.

[00:28:21] This is a classic battle that I see all the time. You have software people saying, Oh, those salespeople, they just go off and play golf with the customer, sell them whatever they asked for. And then us guys, we got to pick up the pieces and the salespeople say, those lazy engineers, they never build anything that we need.

[00:28:35] They're never interested. They don't even play golf. And I have to explain everything in words of one syllable to them and they still don't build it right. And that ship's passing in the night. That's people who don't understand each other. But imagine you had a conversation like this, when we both visited the customer and we went on the floor and we walked around the factory and we saw what people were doing.

[00:28:54] We both observed that their biggest problem was too much cost. And so what we're going to do is cooperate on reducing costs so you can sell at a better rate and you can give better benefits and lists of benefits in terms of reducing cost. And you're going to, as you're out on the factory floor, you're going to help us discover new things that are increasing cost so we can attack them with our new features.

[00:29:16] Imagine if your tech team was talking that way with your sales team. What a different conversation. And that's as a result of trust. I understand that behind the salesperson is out there trying to reduce costs. I'm trying to reduce costs too. And here's how I'm going to bring those two things together.

[00:29:32] When I do that with clients, it's magic. It just really unlocks huge amounts of productivity. 

[00:29:37] Mahan Tavakoli: What an outstanding example of shared stories and shared experiences, looking at the problem or the issue from the same perspective, which often doesn't happen in organizations. We're looking at it from different perspectives, so this can help build that trust.

[00:29:56] , let me just 

[00:29:56] Douglas Squirrel: put in one more thing before I forget it. Which is, I won't go into it here, but there's a whole technique called the ladder of inference, which is a method for getting to that, because I've just said what the outcome is. But I want listeners to know that there's techniques for actually doing this.

[00:30:09] They're like the question circling they're a little more involved but not much And they're the sorts of things you can practice and teach your team So people can learn to do this and have this better conversation and create the trust and then they get the good results It's not just I say, oh great have the good results.

[00:30:24] Okay. Have fun I'm going to help you to actually figure out how to do it.

[00:30:27] Mahan Tavakoli: That's outstanding. And I appreciate you bringing it up, Douglas,

[00:30:30] the other one I would love to get your thoughts on, which I find has been really hard for many of the executives I work with is the accountability conversation.

[00:30:42] How can that be approached? Douglas, 

[00:30:45] Douglas Squirrel: So I stole a technique and then customized it, and I stole it from a guy named Bungay and he stole it, so I don't feel too bad about stealing it, he stole it from the Prussian military of the 1800s. Oh wow! The technique is one that they used to beat the French all through the 1800s.

[00:31:02] First they got beat by the French, then they learned from their enemy, this is good to learn from your competition, and then they used it to trounce them for a very long time, that's why Germany was such a dominant power. And the technique is called something like a mission command or something like that by the military.

[00:31:18] But I call it and Bungay calls it briefing and back briefing. And very simply what you do is you make sure that you align with the person you're working with. By the way, you need lots of trust and you'd mitigate fear. You need to do all the other good things. But once you're at that point where you're using common language and you have the trust of the person, you can come to them with three elements.

[00:31:38] You can say, here's the goal that we're working toward. Here are the constraints and here are your freedoms. And once you give them those things and they tell you, they understand it. You don't believe them. You ask for them to come back to you quickly, like a day later, not enough time to execute anything with their plan.

[00:31:57] That's the back briefing. And often that back briefing reveals some misunderstandings and things that aren't quite right. And then you have an opportunity to correct and you can say, wait a minute. Now you've got a good plan there. You're using your freedoms. You forgot about the cost constraint. This is going to be over budget.

[00:32:12] So don't go off and hire all those people. Wait a minute. You need to bring the cost down and come back again tomorrow with a different plan. Now that level of accountability and that level of structure is something people don't often give when they're delegating. But the benefit of it is that it aligns you on the same language.

[00:32:29] It makes sure that everybody's clear on how you're going to progress. And it allows an awful lot of freedom to the other person. The military example is one where one army was trying to catch up to emperor Napoleon at some point. And the German army had people who were out in the forest and that it was late at night.

[00:32:49] You didn't have any radar, GPS, radio, anything like that. So they had to send a guy on a horse. And we actually have this letter, and the letter says I want you to go north any way you can, infantry cavalry, build a bridge, whatever you have to, go north, and write back to the person on this horse, send me back a letter saying how you're gonna go north.

[00:33:07] So then I can make sure that all the rest of the army goes north with you and supports you, but you can decide how to go north, south, west, those aren't options. Figure out how to go north and tell me how. And when you give that kind of direction and you have the back briefings so you can correct any misunderstanding and align with it, you get an awful lot of productivity very quickly because people are using their local knowledge.

[00:33:29] They know that they're opposite a river so they need to build a bridge or that the infantry is stuck in the mud but the cavalry can really get moving. If you're in that kind of situation where you would like to give freedom to people you're delegating to, but you want to keep them on a short enough lead to stay in touch, this kind of accountability can really work well.

[00:33:47] Mahan Tavakoli: Now, one of the challenges I find, Douglas, is that many leaders and executives feel overwhelmed so what are some of your thoughts and what are you seeing? 

[00:34:00] Douglas Squirrel: It shouldn't take more than a few minutes.

[00:34:02] So this kind of delegation, this kind of accountability is something you can do very efficiently. And free up a lot of time for strategic thinking. So you can come up with new directions and new missions and goals. So what you don't do here is try to get involved in the details. So you don't try to go to the marketing department and say, okay, fine.

[00:34:20] Use this provider. This is the tool as you do. So let's look at the the copy. Let's change the landing page. You're not involved in the details. They come back to you. What I like to say is it's good for them to be accountable to you, but it's inefficient and not very motivating for you to hold them accountable.

[00:34:36] I'm pointing my finger at you, man. It's man, you're doing it wrong here. I'm holding you accountable. We can do that when people do stuff that's actively unethical, but in cases where we'd like them to have a certain amount of autonomy. But still be aligned with us. The best thing is for them to be the ones responsible coming back to us.

[00:34:54] So in the case where I was saying, let's do, give the briefing about say the new marketing direction. Then what we're going to do is forget about it until the back briefing tomorrow at two o'clock. We put it in the diary. You and I know that we're going to talk about it. Then we don't have to interact until then I can go think about something else.

[00:35:12] And so I actually, this is super efficient. But still gives you a level of control that is really reassuring. So you have brain space to go off and think about the much more difficult challenge. And that's, what's the greatest risk here. The thing people are lacking the most is the ability to just sit back and think a little bit.

[00:35:30] I know your folks, your coaching encounter this problem. It would be great if they were able to be this efficient, if they were able to structure their delegation and their accountability in this way, so they can actually have some strategic thinking time. 

[00:35:44] Mahan Tavakoli: It would be very helpful. And part of the challenge that I find Douglas, , is that.

[00:35:49] Some of the conversations around accountability aren't as outcome oriented as they should be part of what you mentioned, whether it was the letters sent in the forest to go north, not specifically outlining how to go north to the marketing department that you were talking about, they are. Outcome oriented accountability and communication, not process oriented.

[00:36:18] Douglas Squirrel: Precisely. And what you really care about is the outcome, after all. So at the marketing department, you want them to produce more qualified leads so you can go off and chase them down and collect money. It doesn't really matter how they got them. Did they get them by outbound phone calls? Did they get them by a web advertisement?

[00:36:33] Did they get them by putting signs on buses? It really doesn't matter to you. It shouldn't matter to you. So long as they're doing it ethically, they're doing it in line with the constraints that you give them. They're not, buying expensive TV ads for a 5 product. There are constraints you can put in place, but often what we do is we focus on what are the steps you're going to follow, how is this going to look?

[00:36:55] What are the actions you're going to take? And the actions don't matter. It would be great if all of them could get finished and they only work four hours a day. We don't care how much time they spend on it. We're not paying by the time unit, but we're paying their salaries to get a result. And if you start thinking that way, it really shifts your attitude and it lets you manage people in areas that you know nothing about like artificial intelligence or deep operational expertise that you as a leader might not have and don't need to have.

[00:37:24] Cause you can focus on the outcome. Hey engineers, I want to make sure that more people come to our website. Marketing people. I want to make sure that we have more qualified leads. It goes from two a day to five a day, whatever the outcome is, you can give that direction and then have them be accountable to you for what resources they need, what challenges they're having and how they're progressing on that outcome.

[00:37:47] Mahan Tavakoli: It's this type of thinking and these types of conversations, Douglas, that I feel are lacking in some organizations that are still struggling with hybrid work and leaders that are having lots of problems with it. So there's a lot to learn from that. Now you also have a conversation scoring tool. Would love to get your thoughts on how leaders can use the conversation scoring tool in.

[00:38:13] Understanding where they can focus their efforts for the greatest impact in the conversations for their teams and organizations. 

[00:38:21] Douglas Squirrel: Fantastic question. And the good news is there are multiple tools, and you can use them in all kinds of different cases. So I'll just give one example we've already talked about, and another one that's slightly different.

[00:38:31] But there are lots of them. And they all come down to that basic step I was saying to follow, not if you're driving. But, write down your conversation, say what you said, the other person what you were thinking. And then you take that record and you analyze it. And I showed you an example of that.

[00:38:46] I asked you Mahan to think of a conversation and think if I were to go through and circle all the question marks, what score would I get? Would I have 10 question marks? Would I have five question marks? The typical scores are like one or zero. And if you look back at that one question mark, it's one of those leading questions.

[00:39:00] Don't you agree that we should go this direction? Wouldn't a Chinese rollout be really helpful? And it's not a genuine question. So it really doesn't count. So when you look at that kind of thing, you're doing a scorecard, you're doing a scoring exercise for yourself. On this conversation that you actually had and you can revise it.

[00:39:18] So you can go back through with a red pen and put in more questions. You can say, Oh, I was thinking of this question, but I never actually asked Mahan. I'm going to put it here in the right hand side and then practice, try it with chat GPT or with a friend or the actual person, and you can say, all right, did that work better?

[00:39:33] Was I able to get more of the information I wanted? So that's one example we already talked about. Another one on trust for this tool called the ladder of inference. Is to look to make sure that you're following all the steps. One of the things about building trust is you have to go a little bit more slowly.

[00:39:49] So it feels when you might run down the street to catch a bus or something, you might be moving fast. Imagine the street is icy. You might go a little more slowly. You might even get, some sticks that are pointy and, you're making your way along carefully or wear snowshoes or something.

[00:40:02] So you don't slip. And you feel like that in the conversation, and there are rungs on the ladder. I won't go into them here. They're in the book, but there are steps that you can follow. First, you ask, what did you see? What was important about that to you? What did it mean to you? What were your conclusions from that?

[00:40:18] What beliefs did you create? What actions did you, were the results? And you can score yourself on whether you actually went slow enough, because the temptation is just to say, okay, fine. Mahan, you're all wet about that. That's completely wrong. Don't do that. Instead do this. You're jumping to the top of the ladder.

[00:40:34] Whereas if I ask more questions and I keep myself to the structure, then I'm building trust with you because we're building a shared story. And I'm saying, ah, Mahan, I understand now why you're doing that. It's because this means to you that I'm not giving you enough resources. That's the meaning you're assigning to it.

[00:40:52] And we could take some steps at that rung of the ladder that would change our interaction. Now that I know you're concerned about getting enough resources. If I just jump to the top and say, Mahan, why aren't you sending more emails? Why aren't you marketing more? Why aren't you getting more for me? I'm never going to learn that I won't be able to take action on it, and I can see that in my conversation.

[00:41:11] I can score it and say, did I follow all the steps? Nobody does it perfectly. Nobody gets 100 percent score. We're not looking to get an A, most of us get a zero. So if we can move from 0 to 50%, we'd be doing real well. And that kind of scoring and that kind of exercise is tremendous for you to do as a leader.

[00:41:29] It's tremendous for your team to do. There are lots of practices and tools. For people to learn those methods to give themselves scores and to improve in their level of trust building conversations, 

[00:41:40] Mahan Tavakoli: you do have a lot of these tools, now, in addition to your book, Douglas, are there any resources or practices you typically find yourself recommending when people want to become better at Holding the types of conversations that can impact their teams and organizations in a positive way.

[00:41:59] Douglas Squirrel: I'll tell you how I did it because I was terrible at having conversations. I'm now just mediocre. I teach people how to do it, but it's because I got from really bad where most of us live all the time to okay. And the way I got there is relentless practice. In what I now call a conversational dojo, and a dojo, you might know is a term from karate martial arts, and it's a place where you get together, not to have real fights, you're not actually trying to knock the other guy out, but you do practice all the moves, all the things that you would do in a tournament or an actual street fight, and you learn how to do the practices better, and then you can apply it in whatever place you want to.

[00:42:39] So in the same way, You or the people in your team or people that are coaching you, however you want to do it, can gather together, look at the conversations you're having, give them these scores, analyze how they're working for you, And improve them and improve just the kinds of conversations that you're having and that immediately has a huge productivity impact and impact on trust and impact on accountability.

[00:43:04] If listeners are interested, I'm very happy to send them. A little worksheet on how to do a conversational dojo, what to score, how to improve these things are not difficult. They require energy, they require discipline and paying attention, but there are tools that you can learn to use.

[00:43:20] And so my favorite way is to do what I did for quite a while, which was to practice relentlessly and a conversational dojo is one way to do that. And I'm happy to send listeners material on that. It's very simple to get started. If you'd like to. 

[00:43:33] Mahan Tavakoli: Outstanding. We'd love to know about that as well as how the audience can find out more about you, Douglas, your book and follow your work newsletter, 

[00:43:42] I have a podcast. I'm just launching a new podcast. That'll be out by the time this comes out. I have tons of stuff. The place to start is at Douglas squirrel. com. So you just have to remember my name and that's got my email. It's got my home address. You can come visit me in my 600 year old house here in England, if you want to.

[00:43:59] Douglas Squirrel: And it's got lots of material videos. I do events. I run the book agile conversations which I'm happy to put listeners in touch with if if they'd like to get a copy of the book with all the techniques and so on. Or simpler material like the conversational dojo that can get you started as a bit of a taster.

[00:44:15] So all that stuff is at douglassquirrel. com, along with my community, where I run my newsletter, where I have weekly events, and so on and that's a community of thousands of tech and non tech people cooperating and learning together. 

[00:44:29] Mahan Tavakoli:  I appreciate the outstanding conversation on conversations. Thank you so much, Douglas squirrel. Likewise, Mahan have a wonderful day.