Podcast Episode 18

with our guest Jeff Eggers

Jeff Eggers: Leaders, Myth and Reality

BRYAN: 00:00:00 Today my guest is Jeff Eggers. Jeff, I don’t even know where to start introducing Jeff. He retired from the navy in 2013 after a 20 year career as a US navy seal. He served in the White House for six years, most recently as President Obama’s special assistant for national security affairs, he also served under President Bush. He earned an award, the Samuel Nelson Drew Award for Distinguished Contribution in Pursuit of Global Peace. That award was given to him by President Obama for his role in mediating the political crisis following the 2014 Afghan presidential elections, which I’m sure you were following closely. We talk about leadership and the book that he’s just written with four star general Stanley McChrystal and with Jason Mangone. The book is Leaders, Myth and Reality. In this book, he profiles 13 leaders from all walks of life. We talk about some very practical things that you can do to increase the quality of your leadership. I think it’s fascinating. I think if you want to take your ideas and to translate them into reality, put them, especially in a written form, that you will find something here that is extraordinarily useful to you. Jeff, welcome to the School for Good Living podcast.

JEFF: 00:02:12 Thanks Brian, great to be with you.

JEFF: 00:02:14 I was looking on your facebook page the other day-

JEFF: 00:02:16 Oh jeez.

JEFF: 00:02:16 -in preparation for our conversation and I saw something that really intrigued me. Just before we started recording here, you were telling me a little bit about paragliding and I saw something on your facebook page about the X, the Red Bull X Challenge. Am I getting that right?

JEFF: 00:02:31 That’s right. You got it.

JEFF: 00:02:32 Tell me about that. What, what’s, uh, I’d never heard of that event, but it looks awesome.

JEFF: 00:02:37 So first of all, if all good research starts on facebook, I’ve got something to learn from you, because I’m not, I’m not an avid facebook user, but as you picked up on, it’s something of where I put more personal interests in. Generally the more professional or author based interests go on twitter, linkedin, and so forth. Um, yet to break into instagram. Um, but facebook is where my personal self resides and that’s why you see paragliding there because that’s a big hobby of mine. And the red bull x Alps is this crazy, insane race they do every other year. It’s so crazy, they don’t even do it every year, but as of now they’re doing it every other year and they pull about 30 of the world’s best pilots and they essentially have to race from one end of the Alps in Austria to the other end where the alps hit the Mediterranean and France and they have to do it all either flying in the air or on foot. So it’s a long, brutal race and it’s pretty insane as far as paragliding goes.

JEFF: 00:03:47 Wow, that sounds incredible. Is it something that you’ve participated in? Have you been a spectator? Just follow it online?

JEFF: 00:03:53 Oh no, it’s, it’s pretty high end competitive paragliding. I can aspire to do it and I might be aspiring to do it for the rest of my life. It’s one of those things that most of us competitive paragliders look upon with awe and reverence and hope that we could someday be at that level, but that’s, it’s pretty aspirational at this point.

JEFF: 00:04:19 Yeah, it looks amazing, you know, because there’s, you know, what paragliding needs is more fatigued athletes. Right? So doing all of that climbing and the racing aspect is like, wow, only red bull would do something so extreme, I think.

JEFF: 00:04:35 Yeah, and to be honest with you, that’s one of the real dilemmas is that you want to be on your mental game when you’re flying a paraglider in dicy conditions, and the very nature of the race means that the athletes are going to be operating at their physiological limits while also flying in some, um, some pretty extreme conditions. And that’s obviously something that from a safety point of view, you’ve got to look out for.

JEFF: 00:05:05 Well, thanks for sharing that with me. I realized we haven’t done, you know, background on you and I’m going to ask you in just a moment to tell me a little bit about yourself. Before we go there though, I want to go with a question I love to ask all my guests just right out of the gates. What is life about?

JEFF: 00:05:25 Mmm. I’ve actually got a pretty simple answer for that, very top of mind, and it’s something I learned from a book by Viktor Frankl and in fact it’s the title of the book and the thesis of the book and that’s Man’s Search For Meaning. So, you know, my answer is that we’re all essentially driven by this quest for finding meaning in our future lives, right? That we’re all more or less driven by some sort of anticipation of what could be and how we find meaning in the road ahead or on the road ahead. And that, you know, that ties into what I ended up writing a book about, but it also ties into just kind of some early philosophical slash psychological readings I was doing when I was younger and mostly in Viktor Frankl’s work.

JEFF: 00:06:27 Yeah. That book is amazing.

JEFF: 00:06:30 It is, yeah.

JEFF: 00:06:31 Totally. Probably the single most referenced book in the 18 interviews I’ve done now, to be honest-

JEFF: 00:06:38 Oh that’s interesting.

JEFF: 00:06:39 Yeah. And maybe not surprising giving that question right that I asked what’s life about. But yeah, definitely comes up a lot in, in the conversation that I have. So when you introduce yourself, and I realize this will change context to context or person that you’re talking to, but how do you typically respond when somebody asks you who you are and what you do? What do you say?

JEFF: 00:07:02 Great question. And I love the way you frame it because how you answer probably says a lot in and of itself and you know, I try to start with a little bit of my family, and either come at that from, depending on the context, I was the son of an air force officer and a history teacher and grew up in New Hampshire and that’s a big formative part of who I am or that I’m the father of two kids and the husband of a then fellow government employee, civil servant. She’s still in the government. So there’s kind of the local proximate family answer and then there’s the broader extended family answer. But I typically start with one of those two places rather than a professional answer. You know, I used to live in Hawaii, I spent four years in Oahu with the navy and one of the things you realize living in Hawaii is that there’s a different way to answer the question, tell me a bit about yourself or who are you, particularly when you move from Hawaii and you resettle in Washington DC. In Hawaii, people only ever answered the question in terms of either their family or their hobbies. Whereas in Washington DC, people only ever answered the question in terms of their professional identity and it’s- it couldn’t be more starkly different and I keep a little bit of that Hawaiian self that always answers the question either in terms of family or hobbies rather than, you know, I do x, y, and z Monday to Friday, nine to five.

JEFF: 00:08:45 I love that, by the way, and I know when we connected just a couple weeks ago, I made a comment about your eight oh eight area code, the Hawaiian area code, and I love that that’s not just a matter of convenience perhaps keeping that, but it sounds like there’s some symbolism or some deeper meaning for you in preserving that area code and what it means for your life.

JEFF: 00:09:03 There is, like I told you, it’s convenience. Once you have a phone number, you never want to get rid of it because that just makes your life difficult. But there was a deeper sense of identity rooted in that eight oh eight identity and I’m glad to keep that and have that kind of as a reminder.

JEFF: 00:09:21 Yeah. That’s cool. So there’s a few things that I want to ask you about leading up to the writing that you do. One of the things I see is that you spent 20 years as a navy seal and lots of military and civil service. In addition to that, including being presented by President Obama in 2014, the Samuel Nelson Drew Award for Distinguished Contribution to the Pursuit of Global Peace. Right. Which is pretty amazing. I just wonder if you would be willing to share a little bit about- I know that’s a really broad question, in two decades of experience. I’m looking for one kind of insight. Just tell me a little bit about what that was like. I mean, why you went in. I mean, I understand you were the son of an air force pilot, but why you followed in the footsteps of becoming a warrior and a servant?

JEFF: 00:10:18 Yeah. Yeah. I, you know, it’s funny when you, when you play it back like that, it sounds different than it felt along the way to be honest with you. You don’t set out on a path like that with those types of thoughts or ambitions or motivations. At least I didn’t. And for me it, you know, in, in all candor, it was a, it was being the son of an air force officer and growing up in literally the cockpit of an airplane that shaped someone who wanted to go into the military and I went to the Naval Academy. That was my road into the navy and I went there very much wanting to fly and the only difference from my father is I wanted a more extreme form of aviation and air force aviation where they land on mile long runways look relatively pedestrian compared to lending on the pitching deck of an aircraft carrier at night at sea. And so I went to the Naval Academy for that reason, I wanted a more extreme, interesting form of aviation. But then quickly after I got there, I realized that being in the military wasn’t about being the operator of a technical piece of machinery, that really what it was about and what it had always been about was this thing we call leadership. And so very early on I became consumed with this, this idea of leadership. And I made a pretty hard turn away from aviation towards, in this case, special operations because I wanted to go into this study and this practice of leadership. And that was a big decision for me because for as long as I could remember, I wanted to be a pilot, and then- sometimes I still do, hence the paragliding, but you know, I decided to make the naval career all about leadership and special operations was the best place to pursue that and then it just kind of built on itself and whether it was the navy and special operations or later the civil service in national security and foreign policy. It was built on that thread that started with my father, but then kind of got shaped by the pursuit of leadership and in many ways that’s still with me today.

BRYAN: 00:12:50 Why is leadership something that was so interesting to you?

JEFF: 00:12:54 Great question. You know what, that’s something I’m still figuring out is why I’m so interested in this, to be honest with you I think my interest in this lies in the psychology and the behavioral science of what motivates us and what binds us together into these groups that assemble and try to achieve something and then whether or not they achieve it or not, all of that is very interested in me. And I think that is mostly a question of psychology and behavioral science. And that’s the angle that I take on leadership and it’s always fascinated me, in this point, I’m interested in it because I think there’s still a tremendous amount to learn. In other words, I don’t think it’s a very, if it’s a science and I think there is a science to it, but if it’s a science, it’s not a very mature science. And so it’s a great place to be because there’s so much still to learn about this thing we call leadership.

BRYAN: 00:13:59 Yeah, for sure. I did a leadership program a few years ago in which, you know, I came across an idea that, I believe you just released a piece about, I think it was in Forbes, but it talked about this- kind of the myths of leadership, and how even the very definition of leadership is disputed among those who teach leadership. And if we can’t even agree on something as simple as a definition, how much less likely we are to be able to understand or effectively teach leadership. And in the program I did that was also called out early. And what I took away from that was this idea that, you know, leadership is taught in so many forms, whether it’s military or whether it’s in business or you know, in the worlds of NGOs and philanthropy and this kind of thing. Yet it’s one thing to talk about, you know, the great men and women of history and hold them up as examples where there’s so much that is situational that is contextual and to look at their lives, yeah they can be inspirational and it can be instructional, but merely doing that or teaching theory does not leave one being a leader. Right, otherwise, if that were the case, probably you know, these, these last few decades of some of the financial industries collapsed, probably wouldn’t have happened. You know, these things that were like ethical lapses. What’s your view on why despite probably knowing more now than we ever have about behavior and leadership and other social sciences and stuff like that. Why is it that leadership is not something that is like I would say, consistently taught successfully in whatever form?

JEFF: 00:15:45 And I’ve experienced a little bit of both sides of that. You know, the, the book ended up being called Leaders, Myth and Reality and when we set out to write it, and I say we because I wrote it with two amazing coauthors, Stan McChrystal and Jay Mangone, so when the three of us set out to do this, we didn’t have a working title to be honest with you, and Leaders, Myth and Reality emerged through the process of writing the book because we really came to see most of what we had been taught formally about leadership either in the military or in the private side of life where we are now was disconnected or far removed from our experience with leadership, and that was true both early in the military and more recently in the private sector. And we came to talk about this disconnect between how we talk about leadership and how it’s experienced or how it comes through in reality. So we saw that in our personal lives and then we saw that in these 13 historical profiles we studied. That became the base. You know, the basic core of the book is the stories of these 13 leaders. And most of what we saw there and what we saw in our personal lives was this disconnect between myth and reality so that became the title of the book Leaders, Myth and Reality. And it does go all the way back to my earliest memories of my first leadership courses at the Naval Academy. I mean, leadership is such a big deal at the Naval Academy, they have a whole building and academic department essentially devoted to it, like you don’t find that at most colleges, but at the Naval Academy they invest a lot of this- so students at the Naval Academy go through a pretty standardized leadership curriculum. And you know, I went- so I went through that in starting late eighties, early nineties. The curriculum, as you alluded to, was based very much on this idea of honing one’s ethical leadership or having leaders of a particularly robust and thick moral fiber. And a lot of that was born out of, you know, the lessons the military had learned in its last war, which at the time was the Vietnam War. Uh, but as well, lessons that were coming out of business in that era and probably the most notable one of that era was the breakdown at Enron, right. And so there was this kind of very ethics heavy version of thinking about leadership and that really being a leader meant being of this particularly strong kind of moral fiber, and what you see today and then historically is that that’s actually not the case, like we do look up to and follow people who like all of us are fallible in their moral discretion and whether that’s well known or not, it’s generally true. And so that’s the earliest example of this disconnect I can remember. And then we’ve only encountered more and more since then and that’s why it became such a heavy theme in the book.

BRYAN: 00:19:16 Yeah, how did you choose these 13 profiles? I love the question in the book, who would Plutarch write about today? Right, and so these 13 that you chose, why did you choose these people?

JEFF: 00:19:29 Yeah, and we have to give credit where credit’s due here. That original question was inspired and borrowed from David Brooks, the New York Times columnist, and the speech he gave, and there were some other influences that pushed us towards Plutarch, but we really did want to write a book in the model of Plutarch’s Lives, and if your listeners aren’t familiar with that, they should be forgiven because neither were we when we started out on this and we actually had to look it up ourselves. We, you know, we all went out and got a copy of this thing, of Plutarch’s Lives. Yeah, this is a special one. This is kind of the one that was a gift. But, um, you know, the thing that Plutarch did was he established this, this, form of biography- biography that in his way was all about looking at pairs of famous Greeks and Romans. And he always, he always created as pairs with one Greek alongside one Roman. But moreover, not only did he try to walk through the actual stories of their lives as leaders, not in a highly romanticized way, but in a nuts and bolts, this is how their stories actually unfolded with the best accounts he could get access to, but then he also compared the two side by side. And that methodology of writing a biography of two people as a pairing and then comparing them was appealing to us and that became the structure of our book where we, for the most part, we had Robert E. Lee as a standalone, but otherwise we had six pairs of leaders organized into these six genres and of course they’re not one Greek and one Roman. They’re organized by genres that are very kind of general, but tried to give some angle on the idea of leadership. So for example, one of them was a pair of founders or entrepreneurs in today’s language, but we called it The Founders and they were Walt Disney and Coco Chanel. And the question there was, how did you have these two people who by today’s business school standards had quote unquote the wrong leadership style, right, yet succeed in establishing and holding on to these now iconic legacy brands that everyone would acknowledge were hugely successful. How did they do that with the quote wrong leadership style? And to really dig into that- but then it, you know, at the other end of the spectrum, we looked at the genre we ended up calling Geniuses. And that became Albert Einstein and Leonard Bernstein. And there the question was with these two people who had really not a serious form of formal leadership, you know, Einstein never really led a real organization, he turned down the presidency of Israel when it was offered to him and Leonard Bernstein, you know, led his orchestra. And that’s interesting. But more broadly, he reshaped how Americans think of orchestral and also Broadway music. And so whether it was redefining how we think of physics or how we think of music, how is it that you can have this massive amount of influence over how people think without having real formal authority to change how they think? And so across these six different genres of leadership, we wanted to dive into these questions of why do we have this gap between how we talk about leadership and how it’s experienced and what does that suggest about ways we should think about leadership more clearly.

JEFF: 00:23:42 How did you come up with this formulation? I mean, I understand, what you’re saying is pretty straightforward. How can we close the gap between how we think about it and how we experience it? But how was it- and I get the Plutarch thing. There were the Romans and the Greeks. But why did you come up with, you know, these 13. And why is, why is Lee a standalone, by the way, why doesn’t he have a kind of a companion?

JEFF: 00:24:06 To be honest with you, it’s because one, he has a special place in the book because he had a special place for our coauthor Stan. Stan grew up literally in the neighborhood of Lee’s childhood home. Stan went to Washington Lee High School named after him and then he attended West Point where the legacy of Lee dominates everywhere. There’s buildings named after him, there’s streets named after him, and then had this moment more recently in the wake of the issues surrounding Charlottesville and so forth where Lee’s reputation and legacy really took a turn, in more modern times and in the book you can read about this kind of moment where he has this painting of Lee on the wall that’s been there for decades because his wife gave it to him when they were younger and he decides to take it down and put it in the trash because he decides that the legacy of Lee has been misrepresented in his mind in some ways. And so Lee was always going to be in the book because Stan had such a fascination with this question of how is it that somebody who got it so wrong in many ways could be held up as such a lionized and revered leader for so long. Now that’s why Lee’s in the book. Now, Lee didn’t get paired with anybody simply because we knew we needed to give him a special treatment and it was too controversial to try and pair him with somebody, for somewhat obvious reasons. Like what would it say about the other person if you paired them with Lee. The third reason I give you, which is a little bit geeky or wonky, but Plutarch actually had profiles that didn’t end up getting paired and it’s not entirely clear why those profiles ended up that way. A lot of that record is lost to history just because it’s, you know, thousands of years old, but Plutarch actually in his- what is now the surviving version of his Lives, there are profiles that that didn’t get paired and so in some ways we could say, well, if we really want to follow up Plutarch’s model, we should have some unpaired people and that’s where Lee checks that box, if nothing else.

BRYAN: 00:26:46 Yeah, that’s totally legit. Jeff, who did you write this book for and what did you want it to do for them?

JEFF: 00:26:54 So we wrote it for a very general audience. We wanted this book to have broad appeal, whether, you know, it was our spouses, our moms, our friends or people who think in more focused ways about leadership, i.e. fellow scholars or students or practitioners of leadership, we wanted it to apply to people who really were more drawn to the biographical historical treatment of these intriguing stories of these 13 people, but as well people who are interested in these same questions we are about how do we get leadership wrong and how would we redefine leadership to get it better? And that’s a pretty broad spectrum. Um, you know, biographical books that do well, like Chernow’s Hamilton for example, or Grant, are appreciated by students of history and students of biography and so forth, and they make for very good reads. Most business books on leadership have a different audience, right? They tend to be very kind of management speak or business speak. We tried to write a book that would actually appeal to that entire spectrum and would offer something to both type of reader. And that’s why in some ways we felt like we were writing a very different kind of book because it didn’t, it didn’t fall easily into either genre.

BRYAN: 00:28:35 Yeah, it’s got, as you mentioned, you know, with these 13 profiles, a pretty diverse set of leaders, right? And I think that’s part of what works so well about it is that it, first of all, it’s very readable and as told in these profiles, in these stories, you know, looking at all these different examples, it’s really interesting. You know, it’s really an interesting thing. What did you discover? What interested you or maybe what was the biggest surprise for you either during your research or during your writing of this? What stood out like a big “aha” or big insight for you?

JEFF: 00:29:13 One of the biggest discoveries I had personally was within the Lee chapter itself and you know, we spent a lot of time on the Lee chapter just because we knew it was going to be heavily scrutinized because it’s such a, it’s such a controversial topic and it’s been the subject of public debate recently. And so we really spent a lot of time on that. And for me it was a steep learning curve because I wasn’t like Stan, I wasn’t someone who grew up with the legacy of Lee. I didn’t grow up in the south. I didn’t grow up in the army. And so he was less known to me, but I did grow up thinking that leadership was largely about having the courage to make difficult decisions when they need to be made. And that’s, that comes from a military background, but that’s fairly typical for people who think about leadership. And one of the really interesting discoveries I had was not that Lee decided to go with the army of northern Virginia and fight for the south, of course, or not even that he turned down the opportunity to lead the union, that Lincoln first offered him the job of leading the union army. But more that he made that decision by deferring it to something else. In other words, he didn’t make the decision. He actually said to himself, I will go whichever way Virginia goes, in other words, you- you hinge your trajectory to some other outcome. You really abdicate the decision, and that’s really striking because Lee is held up as a historically great leader. We have, they didn’t all make it in the book, but some of them did, you know, these quotes from people like Churchill and FDR in the 20th century talking about Lee. I mean, Lee was revered in pretty strong ways by a wide variety of people for being this great historical leader. And yet we tend to think of leaders as making great decisions when they need to. And the most important decision of his life, Lee didn’t actually make, I mean, you can criticize him for making the wrong decision or going the wrong way, but even before you get to that, you have to look at the fact that he actually didn’t even make the decision. He just kind of said, I’ll do whatever Virginia ends up doing, and that was a pretty striking and powerful point of analysis for me in the process. I mean, there were lots like that, but that one comes to mind.

BRYAN: 00:32:00 I’m sure that’s true because the very last paragraph of the book, nearing the epilogue it reads, we choose to lead or decide not to. Right? That- when I read that was like, that’s profound. Right? And we’ve all heard, you know, failure to make a choice is making a choice. But I don’t think we always see that in relation to leadership, you know, and for a long time in my career, having watched my parents go into business for themselves, you know, four decades ago, and I’ve had the opportunity to hold a number of different leadership positions in our family business. I used to wonder, you know, why don’t more people aspire to leadership? Why don’t more people want to be entrepreneurs or don’t- want to be managers? You know, it seemed to me like there were very clearly those who wanted to and those who didn’t and I couldn’t understand why anyone would not want to. And then later, you know, when I saw the responsibility and the potential for failure and you know, the, the other obligations that come along with it, it started to make more sense to me. But what’s your understanding of why don’t more people make that choice to be a leader?

JEFF: 00:33:09 Well, in some ways they shouldn’t. And it’s good that they don’t. Because while the trend in leadership has to make- has been to make it more accessible, really ever since the mid part of the 20th century, we, we went and swung fully in the direction of leaders can be taught, leaders can be made, a whole cottage industry was formed for the quote development of leaders, and ever since books about how to become a better leader have proliferated, which gives one the idea that anybody can read a book, take a course and become a leader. There are those who say that’s not true. I agree with them, but most people who say it’s not true do so because they believe that there’s something innate about leadership. And I think there’s a, there’s some truth to that, you know, whether it’s charisma or whatever label we put on it, that really effective leaders have this thing we can’t put our finger on, but is powerful and real nonetheless, and not everybody has it. Right? And I think that there’s some truth to that. And frankly, I think that’s a pretty interesting question of discovery. But the other reason why I think not everybody can or should be a leader is much more simply that it’s really, really hard and if done right, it’s not a lot of fun and it’s tough stuff and frankly, you know, it’s the kind of work that should be arduous and difficult and unglamorous enough that not a lot of people should want to do it because I think where we get it wrong is in thinking that it’s all about the power and the glory and the wealth and the fame or whatever. And in fact, I actually think really effective leaders are, you know, today they happen into more wealth and affluence. But really if they’re doing it right, it’s really just long, hard days of difficult decisions. You tend to be oftentimes less well-liked or certainly scrutinized and criticized by a larger number of people. And that generally doesn’t feel good for most of us. We don’t enjoy that. So in some ways, I don’t think it’s for everybody, not because I think that leaders are born, even though there is some truth to that. I think it’s not for everybody just because it’s so darn difficult.

BRYAN: 00:35:46 Yeah, I can see that. And by the way, as you were articulating that perspective, mentally, I was kind of substituting the word leader for parent and I think many of the things that you said probably hold true for parenting as well, right?

JEFF: 00:36:02 Yeah. Yeah.

JEFF: 00:36:04 Okay. Awesome. So let me, let me ask you a question about your career. I wonder if you’ll tell me a story from your two decades as a navy seal, either where the subject of the story is you or maybe somebody that was in your orbit, somebody that you observed firsthand of a time where you witnessed powerful leadership.

JEFF: 00:36:31 Yeah, sure. I’ll give you a couple. The one where I was the subject was powerfully bad leadership. In other words, a mistake, and this is one I’ve gotten better at talking about publicly, but I do think that like with many things in life, we learn very well when we fail and we can talk about our failures. And so this is- for me, was a great example of that where I single handedly made a big mistake, bad decision, and two of the people in our tasking- and this, this occurred in western Iraq in 2005, almost died as a result, and the fact that the incident happened, um, was 100 percent the result of my bad decision making. And specifically it was an incident where we hit an improvised explosive device, and this frankly happened all the time. I mean this was relatively common, but because it was such a common threat and because it was a pretty dangerous one, we went to pretty great lengths to try and mitigate it. And you know, there was a hundred different ways in which we tried to do that. And you, you couldn’t avoid it entirely. I mean, otherwise you wouldn’t be able to do your job. You had to kind of get out and about. And anytime you did so you were exposing yourself to these improvised explosive or IED threats. But in this one particular case, we had gone through a careful risk analysis of how to mitigate the threat and I deviated from that plan and introduced more risk to the equation and that risk resulted in, sure enough hitting this IED, and it almost killing these two gentlemen and I made deviation because I thought I was quote unquote taking care of the men. I thought I was doing the right thing by helping them get home earlier and getting them out of the field earlier and getting more rest. And in fact, what I was doing was deviating from the plan and introducing more risk and putting them at risk. And so it was this classic case of you thought you were doing the right thing as a leader because you were taking care of your people, but in fact you neglected your greater responsibility, which is to not just complete the mission, but to try to do so keeping them safe. And that was a powerful lesson and in some ways about how to stand up for what is really right and not just what feels superficially good as right. And so that, that was, that was a powerful example in the negative sense where I was the subject of the story. In a more positive example of powerful leadership, you know, I had the opportunity to work for both presidents Bush and Obama, at the White House when I was a national security staffer there, and was very fortunate to have that opportunity. And I would see examples from both of them in this way. You know, one of the, um, one of the stories that I like to tell about President Obama, which is relatively simple, but it’s good for anybody that’s at the top of some leadership structure to borrow from, is the idea of creating a place where people can descend and introduce new and novel ideas so that you try to beat back the tendency to either agree with the boss or to go along with the conventional wisdom where you just end up with group think. And he had a number of ways. Both of them actually had a number of ways of dealing with that because it’s a known risk for anybody at the top of an organization, it’s particularly a risk for the president of the United States, whether you’re sitting in the situation room or sitting in the Oval Office because there’s just this powerful psychological tendency to tell the boss what he wants to hear or what what is going to make them feel better and to not deliver either the bad news or to introduce the idea that everybody might think is crazy and that’s just everybody can say, oh, I don’t do that or, or that doesn’t happen here, but it does. It happens everywhere all the time and it happens I think even with more likelihood in those really extreme cases like the oval office, and so both presidents had their own ways of counteracting those tendencies. For President Bush it was, it was a habit of asking questions and you know, leaders who ask questions are on to something really great because just the act of asking the question if it’s sincere, like not a rhetorical question, but a real question is to demonstrate humility because you don’t know the answer and you’re saying, hey, I don’t know something and you probably do. And so, you know, help make me smarter, or I’m really interested in your views and your thoughts on this. For President Obama, it would be to seek the opinions of the people in the room who were more junior or to do things like to inject a contrarian idea into the discussion so that people would know that it was safe to do so and that this was a place where any idea was welcome and so forth. I think any leader at the top of a system needs to have habits like that because you know, we’re all living with this illusion that people will deliver bad news or junior people can deliver out of the box insights without fear of looking silly or retribution. And that’s just not the case and you can’t rely on their strength or courage to counteract that. The leader has to set the stage in order to do so.

JEFF: 00:42:51 That’s awesome. And what I love about what you’re sharing is that that’s very practicable, right? Like any of us can ask questions, right? And by the way, as you say that, and you acknowledged this, that not all questions are questions, right? Like, are you really going out in that? You know, that’s not really a question.

JEFF: 00:43:12 Again, to go back to your parenting analogy, any parent knows that there’s a difference between a genuine and like a rhetorical question, you know.

JEFF: 00:43:19 Yeah, for sure. And I love what you said with, with the way Bush would ask questions and learn more and you know what I saw that in my dad and my dad as well where, you know, one of, I think his kind of key terms was like educate me, like helped me, you know, even asking what questions should I be asking? And then Obama, um, you know, I didn’t realize that that was something he would do, is kind of introduced the, you know, maybe a contrarian perspective himself and kind of demonstrate that that was safe to do. That’s, that’s pretty cool, and any of us can do that. If you hadn’t have gone into the military, what do you think you would have done instead?

JEFF: 00:43:56 Well, at one time it was going to be lobster fishing.

JEFF: 00:44:00 Was it really now?

JEFF: 00:44:00 I grew up, well, I grew up in New Hampshire and, and before that, a short time in Newport, Rhode Island and so forth, and I don’t know where it came from, aside from living there and eating lobsters and being exposed to it, but at some point it was, um, it was to be a lobster fisherman, but that was pretty early and it didn’t waver much from the path of aviation and becoming a pilot from pretty much my earliest memories until that point I told you about where I was at the Naval Academy. Um, and now that, you know, we’re here in life, you know, you realize that even, you know, pushing 50, you have the opportunity for second and third careers, whether it’s in being more of an academic or more of an author. Um, you know, and so it’s a question that stays with me today and I think most of us still think about this question, what do we want to be when we grow up?

BRYAN: 00:45:05 Yeah, for sure. So, you know, I see in that award I mentioned earlier about this distinguished contribution in pursuit of global peace. That’s pretty cool. To me, that’s pretty unexpected. And when I was in Washington DC just a couple of years ago, I attended an event at the US Institute of Peace and I was really pleased to learn that such an institution exists, right? I mean, we all see the defense budget is so incredibly large and I was like, I’m so glad that somebody’s built a structure and there’s a team here and they’re working on things, but that sounds, that sounds like a pretty cool thing. Tell me about what you did to receive this distinguished contribution in pursuit of global peace. What’s that about?

JEFF: 00:45:51 Well, the specifics of it trace back to Afghanistan and the outcome of the 2014 presidential election which did not go well, as you can imagine. You know, one of the, one of the lessons I think we in foreign policy have learned, um, in some difficult ways since 9/11, at least this is the way I’ve thought about it, is that the solution to these quote unquote fragile states is not the rapid introduction of democratic elections because one of the things we take for granted is that those kinds of elections are built on very important, uh, institutions and those institutions have to be pretty mature before those forms of governance will work. And we take that for granted and we still have trouble with our electoral process. And our institutions are very, very mature. In Iraq and in Afghanistan both, we haven’t had that luxury. And therefore these electoral processes, while they’ve been improving and they’ve, they’ve demonstrated some success, they’ve also been extremely challenged. And in many ways the aftermath of the 2014 presidential elections in Afghanistan were predictably contested and headed towards kind of a political impasse. Maybe even a civil war in that country. And given all that we’d invested in terms of the military fight both in treasure and in lives, the thing deteriorating into a civil war was just in many ways a very bad and worst case outcome and would have really put at jeopardy everything that people had tried to do there. It really came down to trying to mediate the dispute between the two main contenders and those that got the most votes in the end and to try and resolve what the election couldn’t resolve through the votes in the ballot box through a mediated process. And Secretary Kerry, who was then the secretary of state, as well as the leadership at the White House and so forth, put some confidence in a few of us. And it was, it was a team effort. It was by no means something that I did. The ambassador on the ground there, Jim Cunningham, the senior State Department official working for secretary Kerry Dan Feldman, and others worked to mediate this crisis. But I think that the lesson beyond democratic processes in fragile states and Iraq and Afghanistan, so forth, is that mediating peace is much more difficult than pursuing conflict. And, you know, I’ve had the chance now to work both sides of this issue across the course of my career. You know, it’s very easy to fall into an us versus them dynamic and to demonize the opponent and to take up arms with sometimes lethal force against one’s opponent. That’s easy. It’s, it’s really easy. What’s really hard is coming together, finding common ground and finding things to agree about and to fight less about.

BRYAN: 00:49:27 Why do you think it’s so difficult?

JEFF: 00:49:29 That’s a great question. That’s a great question. I think, I think part of the way we’re wired is to fall into an us versus them dynamic. We can very easily form a social identity in opposition to something more than we can just in universal agreement to something. I mean in the simple ways, there’s, there’s always lots to fight about, right? Whether it’s land or um, you know, riches or resources or principles, values, um, there is a lot to fight about. But it gets, I think, particularly slippery and easy because just mentally in a very kind of real cognitive sense, we’re wired to come together in opposition to things and it’s something that leaders over time have exploited, this human tendency to say, yes, I will join this cause because I am for x and I am against y. And I think- so the thing that’s harder and therefore worth spending time on is how do you bridge the two sides, how do you bring opposing sides together, how do you mediate conflict? And to be honest with you, if there’s one thing that I think is worth pursuing and spending the rest of, you know, at least my life on if not the study of leadership, it’s how do you do that? And in both conceptual terms, but then in real terms, whether it’s in Afghanistan or somewhere else.

BRYAN: 00:51:11 What’s the short version of how you, how do you do that? I mean, how did you do that in Afghanistan and how can we do that? Like whether it’s with my spouse, you know, if we can’t decide on, you know, where to go on vacation or some of these things that, you know, might seem pretty minor, but over the course of a few decades of marriage, you know, it can become quite significant, some of these things or whether it’s with a business partner or somebody that we’re, it’s in our family. Like what’s your experience with what makes mediating conflict? What makes that successful?

JEFF: 00:51:43 A couple things, one is to take it literally inch by inch, even if it feels like you’re climbing Mount Everest, which often it does, there is no way to climb Mount Everest other than step by step. You have to do it incrementally inch by inch and therefore you have to pay attention to small little details, small little wins. And they actually matter. Like people will really get emotional and animated by very small details. And so in the course of conflict mediation, there really isn’t any such thing as a detail too small to be overlooked. Um, you know, when I was at the White House the second time with President Obama, we made several efforts at a political dialogue and a political process to reduce the intensity of the conflict in Afghanistan. In one of the things we did was we pursued an office, quote unquote office in Qatar in Doha where talks could be pursued between the warring parties, i.e. that the Afghans, the Afghan government, United States, the Taliban, and so forth. And those types of efforts continue to this day. And you know, they’ve been a part of every arm conflict pretty much that hasn’t resulted in a decisive military victory. So it’s a normal part of the process. But in this case, the opening of that office in Doha, it fumbled, and it fumbled on the smallest of details, the most, the most- things that would normally seem petty become a big deal. And in this case it was as simple as a flag that was hanging in the background when they did the press conference. And there were a couple of other small details. But little things matter and small details matter in small steps. And small winds, if sustained with persistence can add up to quite, you know, a strategic gain. And that’s the lesson of conflict mediation among others is that there really is no- you don’t swing for the fences so to speak. You know, it’s a bunch of base hits type mentality rather than a swinging for the fences.

BRYAN: 00:54:12 In just a moment. I want to transition to asking you about your writing process, before we do though, and I know your book was only released, was it the 18th? October 18th?

JEFF: 00:54:27 23rd, 23rd.

BRYAN: 00:54:27 23rd. So just last week, by the time people hear this, it’ll be at least probably a month or maybe two. But, um, what’s the reception been like? I know you’ve been doing some media and interviews and things like that and General McChrystal has been kind of on tour a little bit, I understand. What’s the initial response been like in the reception of this?

JEFF: 00:54:53 Yeah. So we are really pleased that the book has done quite well in a little over a week. In fact, we just found out that it is already a national bestseller. We just got the Wall Street Journal’s best seller list, which is really our first cut at it because it’s only been out a little over a week, so this first week-

BRYAN: 00:55:16 Yeah, congratulations. That’s- that’s awesome.

JEFF: 00:55:19 Oh, thanks. It just, I just saw it in fact this morning we’re number four on the Wall Street Journal’s list after one week. So the book is doing well. It’s selling well. We, I think we hit not deliberately, but just by virtue of timing an important topic at an important time. And I don’t mean just that we’re talking about leadership in the run up to, you know, midterm US elections, but that many people are having powerful and thoughtful questions about this thing we call leadership at the time that we launched a book that dives into that exact question and whether it’s in work or personal lives or in politics. Many of us I think are frustrated with leadership. We do have questions about it, and the book, again, happens to address in pretty fundamental and direct ways those questions. So we’ve been pleased that it’s gotten a good response and you know, it’s fun to talk about, it’s fun to talk about because one, the 13 people that we wrote about are very interesting people and they’re fun to talk about all by themselves, whether it’s Coco Chanel or Abu Musab al-Zarqawi or Boss Tweed or Margaret Thatcher. These people had pretty interesting lives and they’re pretty fun to talk about, but equally the broader question of what are the myths of leadership that we mistakenly believe in or subscribe to and how can we get it better and how can we get it more right in our lives. That’s also fun to talk about. So I’m excited the book is doing well because I’m happy, you know, I’m happy as a clam to keep talking. So hopefully it just keeps getting better and better.

BRYAN: 00:57:13 Yeah. One of the things I’m really struck by is how with your experience and your training, to see that where it led you, you know, basically my understanding of a navy seal is that you’re basically the most sophisticated, effective killing machine on the planet. And it led you to these really profound insights about, you know, peace, actually. I think there’s something really, really profound about that actually.

JEFF: 00:57:40 You know, I think we in the military all have some version of that experience, not just in special operations. We actually touched upon this in an Op Ed we wrote in the Wall Street Journal recently talking about whether or not Americans should vote for veterans and reasons why you should or you shouldn’t, and you know, we generally come down, there’s lots of great reasons you should, you should just do it thoughtfully and not instinctively, like don’t automatically vote for a veteran. But one of the reasons we think veterans bring a potential unique experience to politics is that while soldiers are almost by definition going to learn to dehumanize their enemy because that makes it easier to kill them, that soldiers also, through their experiences, can have this almost unexpected counter-intuitive reaction where they learn to humanize their enemy and they can understand that the people fighting on the other side are humans like them. They’re parents, they’re sons, they’re fathers. And they have different values, they have a different uniform, they fight for a different cause or different beliefs, but that we’re all human. And in one of the things we came across, we didn’t end up writing about this in the book, although we dedicated the book to him, was an experience John McCain had where, you know, he served as a prisoner of war for five years. And in the course of his time in the Vietnamese- the northern Vietnamese prison, he was visited by some American activists who actually kind of condemned McCain’s and the other, the other military member’s actions, you know, essentially calling them baby killers and so forth and gave McCain every reason to hate him really. And over the course of his life, McCain actually came to forgive those activists, and one in particular, David Ifshin, who was the most notorious of those that took those actions to the point where McCain actually spoke at Ifshin’s funeral, in powerful ways that demonstrated that he had actually learned to forgive this person who had really been one of his enemies and one of his opponents, and in those types of counter-intuitive or unexpected ways of thinking about the enemy in more common terms, that’s a unique thing, right? Particularly in politics. And so, and I’m not saying every veteran has that experience, but now all three of us who wrote the book, we’re all veterans and we all related to that in various ways. And I think, you know, in many ways people join the military, they look forward to war because they’ve been trained to war. I know that’s a difficult thing to hear or say, but it’s true. Like when you spend your whole life preparing for war, many people before they ever go the first time are actually somewhat eager to go, right? Even though we know we should never look forward to war, because it’s your job and because your job actually lionizes the people in the past who have been to war. It is this thing people do tend to want to go do. But then after they’ve done it once or certainly twice or multiple times, it starts to feel very different and you start to see it for what it is in all its horror and ugliness and so forth. Even when it’s got the best of causes or principles or needs behind it. Right? There’s still an ugliness to it that’s unavoidable because by definition it is the pursuit of defeating, usually through some lethal means, one’s enemy. And once you see that other side of it up close, you have a very different perspective about armed conflict and when a country should go to war, why it should go to war and how it should make those kinds of decisions. And that I feel like I have seen across many of my veteran friends is that you do have a, just a richer appreciation for conflict and therefore ways to avoid conflict or mediate conflict as well.

BRYAN: 01:02:32 Yeah. You know, I think about something I once heard that Gandhi said about there is no, there is no way to peace. Peace is the way. Right? Like as I hear you talking about what it takes for many people to have this perspective of maybe our universal connection or whatever it is to actually go have the experience of engaging in conflict and then seeing it firsthand and then kind of being disabused perhaps of this perspective that it’s this thing to be celebrated or, you know, desired after in some way. And what I wonder is, you know, why does it take that? Is it possible for people to have some kind of a perspective shift without having to experience, you know, the atrocity firsthand? What’s your view?

JEFF: 01:03:23 Well, I do think that there is a way to do what you’re getting at. We’ve done it before, which is that when a democracy is going to make a decision to go to war, the entirety of the democracy should have some skin in the game. Not just those who are literally going to put on the uniform and go. Right? One of the problems we have today is you have one, you have a volunteer army, right? We no longer have a draft or conscription. So there’s no fear of being drafted, so to speak and getting called up if the country goes to war because you know, you know who’s going to go and you know who’s not going to go, right? And moreover, the way the wars are fought in modern times is they’re fought abroad, right? All these interventions are pretty far away and pretty far removed both physically and financially, which is very interesting. Like if you think about it, people’s taxes haven’t been going up as a result of our ongoing wars. And that’s because we’ve gotten these kind of new financial models that fund the wars through kind of, you know, without getting into the technical details of how it works, kind of off budget ways of accounting for these things.

BRYAN: 01:04:52 Sorry to jump in, but yeah, and nobody, I mean things I read about when I studied in Japan, and I know this happened in the United States as well about rationing, right? Whether it’s fuel, whether it’s food, whether it’s metal. People literally giving up their cookware, you know, stuff like this.

JEFF: 01:05:08 In the US, people used to plant victory gardens, right? And so through all these various means there was a little bit more skin in the game from the constituency behind the decision to go to war and we’ve really ratcheted that way back where now you have one percent of the American population that’s served and maybe two percent that’s been exposed to the service if you include, you know, families and loved ones and so forth. And that’s, and then the rest of the 98 percent has more or less been going about life business as usual, and haven’t even had to pay an increased tax as a result of this. And I just don’t- I think that’s a fundamental part of where it gets unhealthy about these kinds of decisions. It isn’t to say that military force is unnecessary. Of course there are times where it is necessary otherwise, why have a military? Right? And you know, that’s a different debate. But I would take the position that of course having a military force and using a military force is at times necessary. The real rub is how and when you make that decision to employ it and use it and how you make sure you make good decisions goes right back to making sure people have some skin in that outcome and you will make better decisions if you do.

BRYAN: 01:06:40 Yeah. That makes sense. What’s that Thomas Paine, “That which is obtained too easily is esteemed too lightly,” right?

JEFF: 01:06:46 Yeah. Great.

BRYAN: 01:06:47 Yeah, I think what we’re experiencing there. Okay. So I want to shift before the writing questions, just a few questions that I call the lightning round. So these are unrelated to what we’ve been talking about, a little bit more about you. I’ve written them in a way that they- I think they can be answered concisely, but you can answer as long as you want. So are you ready?

JEFF: 01:07:08 I am. Fire away.

BRYAN: 01:07:10 Question number one, please complete the following sentence with words other than a box of chocolates. Life is like a blank.

JEFF: 01:07:26 Oh, it’s a hell of a journey with ups and downs and twists and turns. Sometimes you’re looking backwards, but most of the time you just got to keep- you know, either stay in the present or looking forward.

BRYAN: 01:07:43 All right. Number two, what do you wish you were better at?

JEFF: 01:07:50 Patience. Patience, mostly because I’m a parent.

BRYAN: 01:07:52 Okay. Number three. If you were required every day for the rest of your life to wear a T-shirt with a slogan on it or a phrase or saying, or quote or quip, what would the shirt say?

JEFF: 01:08:04 Keep calm and carry on.

BRYAN: 01:08:07 All right. Number four. What book other than your own have you gifted or recommended most often?

JEFF: 01:08:15 We already talked about it, actually. Man’s Search for Meaning. Viktor Frankl.

BRYAN: 01:08:19 Okay. Yes. All right, number five. So you travel a ton. What’s one travel hack, something you’d do or maybe something you take with you that makes your travel less painful or more enjoyable?

JEFF: 01:08:36 Oh, that’s easy. Noise canceling headphones, ridiculous quantities of vitamin C and always, always, always your workout gear.

BRYAN: 01:08:48 Alright, number six, what’s one thing you’ve started or stopped doing in order to live or age well?

JEFF: 01:08:55 Intermittent fasting, or as it’s increasingly becoming known, time restricted dieting for eating.

BRYAN: 01:09:04 Okay. So I just want to dig on that one for a moment. Where are you learning about this? You’re the second person out of my recent interviews who said that and I’m curious, who are you learning from? I mean I’m sure some of it’s your own experience, but are there any books or podcasts or other websites or resources that are inspiring you in this?

JEFF: 01:09:22 I actually didn’t learn about it through popular literature, which is an indictment of myself. It just is. That’s hard to imagine given how popular it’s become, but I had a friend who was a wellness doctor and really spend a lot of time researching just wealth or wellness, health nutrition, fitness, techniques, habits, whether it’s sleep hygiene and so forth. And he was the one who gave me a kind of a starter’s kit to thinking about the time restriction style of eating and so forth and, and I just stuck with it and frankly that’s all I’ve ever needed because it just started working for me.

BRYAN: 01:10:05 How long have you been doing it?

JEFF: 01:10:06 So I’m coming up on only 10 months now.

BRYAN: 01:10:09 And what are you experiencing?

JEFF: 01:10:10 Well, aside from the obvious, which is, you know, weight loss and some level of just kind of, you know, fitness overall, it’s- for me it’s more about how you feel mentally. I think that there’s-

BRYAN: 01:10:26 Yeah, like sharper?

JEFF: 01:10:28 I don’t want to- it just, I feel crisp and not angry. You don’t get the hangries doing this. I definitely noticed the blood sugar points where you feel physiologically different. I don’t notice it and maybe you know, my wife would be a better gauge of this, but I don’t notice it coming in through in irritability so much as sometimes you just don’t feel like you’re ready to run a marathon, if you know what I mean.

BRYAN: 01:10:57 Yeah. Yeah. And I like to always feel ready to run a marathon, you know? But really that’s a good- that’s a pretty good gauge. Well, I think you were- did you tell me that you ran the New York City marathon a little back?

JEFF: 01:11:13 No, that was our friend Ben. Right?

BRYAN: 01:11:16 Yeah. I wondered if you ran it with him or ran in the same year.

JEFF: 01:11:19 No, he and I go running together, but not at that distance. I was actually in town as they were setting up for it, whether it was last week or two weeks ago. And I was thinking to myself, I am so far from running a marathon right now, in any respectable time anyway.

BRYAN: 01:11:35 So number seven, and I’m almost forgetting these were intended to be lightning round. I just jumped in there on that one, but this is another one that might not lend itself to a concise answer, but whatever. Number seven, what’s one thing you wish every American knew?

JEFF: 01:11:51 Civility.

BRYAN: 01:11:56 Why is that important to you?

JEFF: 01:11:59 I just think we’re, we’re, I think the diversity among us is enriching, but I think it’s gotten to the point where we focus too much on our differences rather than being part of something together. And I think that’s where civility comes in, is in thinking of ourselves as part of a, you know, a one America mindset, and in this together, solving things together and so forth.

BRYAN: 01:12:28 Yeah, you know, just going back to something you said earlier, your statement, we’re wired to come together in opposition to things. It’s pretty interesting the nuance in that, that we come together against something, right, but how can we come together about the biggest things, life itself or all of humanity? You know, it’s interesting. Okay. What advice did your parents give you that has made an impact on you or has stayed with you?

JEFF: 01:12:58 Never be late and always return things better than you got them.

BRYAN: 01:13:03 Yeah, that’s true, isn’t it? I mean you were here before me and I was here seven minutes before our scheduled start time, so that really did stay with you. Okay. You know, one thing I didn’t mention on this yet by the way, is about, it’s about your role with the McChrystal Group. Right? And will you just talk a little bit about that? Because my next question is actually what’s your next big project? But I realized that in all the conversations we’ve had so far, we haven’t told listeners about your current role within the McChrystal Group.

JEFF: 01:13:37 Yeah. So the McChrystal Group’s an organizational performance advisory firm, we’re small, about 100 people boutique, so we generally work with very kind of customized solutions and so forth. Within the firm we have this thing called the Leadership Institute, which is what I run and we both do research on these questions of organizational performance and leadership, mostly around what are the most important and cutting edge ideas to improve leadership and organizational performance given all the challenges we’re facing in the 21st century. So that’s broadly what we do is kind of research that question and stay at the front leading edge of those issues and then we try to translate them into training opportunities for the organizations that we work with in terms of either workshopping how we’re gonna change organizational behavior and process to do better or how we’re going to modify our leadership approach at the individual level for the same reason, you know, to try and up our game as an organization.

BRYAN: 01:14:48 Okay. Sounds like a big- sounds like a big responsibility.

JEFF: 01:14:53 Yeah, it’s a lot of fun. It’s what I’m passionate about. It’s what, you know, got me in this career path I’ve been on at the beginning and it’s something that just continues to drive me, this question of, you know, how can we do better together? Whether that’s a system level thing or whether that’s an individual thing, usually it’s got to be some, some combination of both, but I think it’s a critically important question because it pertains not just to, how are you going to make the company more profitable or how are you going to keep the company competitive going forward, but it spills over immediately into how are we as a nation or as a state or as a community going to solve the problems that matter most to us. And so its breadth in some ways in universal relevance is incredibly important. I think.

BRYAN: 01:15:50 Yeah, it’s critical. Critical, especially at this time on earth. If people want to learn more from you or connect with you, what should they do?

JEFF: 01:15:59 So if it’s on this question of how can I improve my organization’s performance as an organization, how can I learn more about those types of things? McChrystal Group does- that simple, our website at mcchrystalgroup.com will be a good source of information in terms of getting started looking at what we do and what we believe and some of our publications and so forth. If you want to connect with me personally, that’s easy as well. Whether it’s on- you can find me on our website, of course, or on twitter at Jeff_Eggers, which is a great way to kind of reach out and connect with me if it’s more about the book and my research and so forth. But yeah, no, I appreciate that, and it’s always great to hear from people, particularly people who take a different view. That’s one of my favorites is people who help our thinking by saying, you know, I heard you talking about, you know, this part of it or that, and you know, I have some experience in this or I have a story that shed some light on this or maybe it gives me a different perspective. That’s great to hear from because I think challenging one another’s thinking in a productive way is one of the most important things we can do. So I’m always eager to hear from people along those lines.

BRYAN: 01:17:27 Awesome. As a way of expressing gratitude to you for sharing your time and your experience and your knowledge with me and with our listeners, one of the things I’ve done is I’ve made a $100 micro loan through Kiva.org to a woman named Gori who lives in south Dinajpur, India, and she’ll use this money to help expand her hand loom business by purchasing thread. So I just wanted to not only tell you that I’m grateful for your time, but also to make some gesture that also demonstrated that. So thank you.

JEFF: 01:18:04 Oh, that’s great. That’s wonderful.

BRYAN: 01:18:06 Okay so the last few questions- you survived the lightning round. Congratulations. Very few people do. So. But what we’ve- so what I’ve got now is I’ve got just a few questions about the act of writing itself. So as it relates to this book, other- maybe something you’re working on now, other writing you’ve done in the past. Just generally. I’m again, I’m interested to ask a few questions that might help our listeners to both have some inspiration and then some practical tips or tools that they can use to get their own projects done. I just want to start by asking what’s your writing kryptonite?

JEFF: 01:18:44 You know, I feel like I don’t really have a Kryptonite, I think that for me, writing is almost always enjoyable. If there is a Kryptonite, it’s the editorial process, which, you know, I think a lot of us who write struggle with because we don’t want to see- we get in love with what we wrote and we have, we lose objectivity over how it could be said better, and so when somebody else picks up a pen and starts changing what we write, I think it feels very threatening, but it’s probably the most important thing to have because none of us does have objectivity about how our writing reads right? Because it came out of our head. It feels good to us. It sounds good to us. And in fact it could be crap. Right? And that’s what the editor does. And that’s why I think editors are almost important as authors and they’re- I don’t know that there’s really such thing as a great author. I think what you have is a great author-editing pairing or system, and that great writing is often the result of great editing as much as it’s the result of great writing or drafting. And I think that’s the tough thing to get used to is just to let an editor tell you, you got to rewrite this whole thing, or this whole paragraph is totally unnecessary. You’re just in love with hearing yourself right here and you need to get rid of it and you really have to learn to listen to that stuff and just live with it.

BRYAN: 01:20:44 Yeah, there’s, um- good thing you don’t have an ego, right? You’re able to hear that then.

JEFF: 01:20:52 I don’t know. I think a lot of authors do, you know, that’s, I think it’s a pretty universal thing and I think that’s why it’s hard for everybody get used to. But it’s critical.

BRYAN: 01:21:04 Yeah. And on this book, and it’s a little uncommon, you’re the first author I’ve interviewed who has written a book with two other co-authors. So there’s three names on this book as you mentioned, Stanley McChrystal, Jeff Eggers, you and Jason Mangone.

JEFF: 01:21:19 Right.

BRYAN: 01:21:19 Tell me a little bit about the division of labor. I mean, how did you- first of all, how did the three of you become attached to this project and how did you approach the responsibilities that each of you would have in the completion of it?

JEFF: 01:21:34 Yeah, it’s- that’s a really interesting story because writing a book with multiple co-authors is not easy, right? Particularly a book like this that is trying to say something new and different and paradigm shifting because it’s unlikely that the three of you are going to agree on precisely what that is and how to say it and-

BRYAN: 01:22:00 Then you have that conflict mediation.

JEFF: 01:22:01 Right! But you know, it’s amazing that we got through that process and remained friends, it’s, you know, a outcome because there were, there were a lot of points where we frankly had some pretty clear disagreements that we had to work through. And so in some ways, the writing of the book is almost as interesting as the stories that were within the book in terms of how we came together and why we came together and so forth. You know, I- the firm that I work at is, is named after Stan, the McChrystal Group, and I run its leadership institute. So in some ways I was the natural person to coauthor a book on the subject of leadership. We as a firm are known for one of our prior books called Team of Teams, which is really about how do you rethink the idea of organizational process and behavior given all the novelty and challenges of the 21st century. So after that, Stan wanted to do something more focused on individual behavior, i.e. leadership, and this book was the outcome of that desire. So I came into the picture because I was in some ways the natural person to do it. Jay was somebody that Stan worked with at the Aspen Institute. They work together on a project of national service. You know, one of the things that their project was focused on was how could the United States get back to this idea of everybody at some point in life does something along the lines of national service- doesn’t have to be in uniform, it doesn’t have to be military. So they knew each other from that experience and at some point Stan and I looked at each other when we got started and we said, you know, we both have day jobs, like we’re running parts of this company and we’re also trying to write this book and we gotta get this book done eventually. So we need some help-

BRYAN: 01:24:05 In this lifetime, right?

JEFF: 01:24:06 Yeah. So Stan reached out to Jay, who we had known from that earlier experience just because we knew we needed a smart good writer to help us get through this. And then in terms of how we divided up the labor, to be honest with you, it was a fascinating process of, in some ways, of course somebody’s got to hold the pen on certain parts. And there was, of course, you know, sections of the book that were written across the three coauthors, but then we’d have this weekly routine of getting together and talking about what we had written or what we wanted to write and what we wanted to change, one so that we could start to establish a similar voice. And I think luckily we had just, almost by coincidence, the good fortune where we didn’t have radically different styles and voices, so that it wasn’t too hard to meld the three pens into a single voice, but more importantly, so that we could hear each other talk out loud about what we were thinking and what we thought the book should say and where it should go. And it was really an evolving process like we, you know, we did not end up where we thought we would. We did not have a clear sense of where we would end up when we started. And so it very much was a living kind of organic, emerging journey that we went on just by getting together and talking about it in this kind of weekly routine and we had daily calls and then a big call every Sunday morning and so forth that were part of our rhythm over the course of the 18 months that we wrote it. But it’s definitely a unique challenge writing with three co-authors, particularly when you set out. And we really did try and view the three of us as equal coauthors. Of course Stan was kind of the headline co-author, and that was obvious from the outset that, you know, his name was going to be bigger, but we really did have kind of an attempt to make it three equal voices and opinions that needed to be heard.

BRYAN: 01:26:16 Yeah, I think you did a great job with that. You know, because the book, as I said earlier, it’s very readable. You know, and if you didn’t know that, you know, there were three authors on the thing, I mean, you’d get the sense this one voice very clearly here.

JEFF: 01:26:34 That’s good to hear.

BRYAN: 01:26:34 Yeah. Good job with that. Tell me, what- would you be willing to share any of those points where maybe you did have a disagreement, you had a different perspective, you know, among you. What was that like and how did you resolve it? I mean, was this like a, was it a vote? Was it something that just kind of you let gestate for a few weeks and it became clear to all of you or like maybe something structural or whether it was content that should be in, or anything. Can you just share a little bit about how that was?

JEFF: 01:27:02 Sure. The first obvious one was who should we profile? I told you that Robert E. Lee was going to be in the book pretty much no matter what from the outset because Stan had such a personal interest in that. But beyond Lee, the other characters or profiles were pretty much, you know, up in the air for decision. We went through hundreds of candidates and our only real criteria were they had to be deceased- that way they couldn’t argue with us, right? And two, they had to be people that had some name recognition. At one stage, very early on, we thought about pairing household names with completely anonymous people, but what we ended up doing was to pick all household names, and the reason we did that is because we wanted to shed a little bit of light on somebody who everybody thinks they know or thinks that they are familiar with in a unique and novel way so that you actually come away going, wow, I didn’t know that about Margaret Thatcher or I didn’t know that about Coco Chanel. Even though I kind of know who these people are and what they did, I learned something and I think that’s really interesting for us is to realize there’s always something new to learn and to try and present something in each case. So picking the 13 people was a point of disagreement and tension, of course everybody had a different preference, not just at the individual level but at the genre level or the broad categories. For instance, for a long time we felt that an athlete or some leader in professional sports should be part of the collection because sports is such an important thing to so many people and you do find leadership in sports and so whether or not to include someone from sports in the 13 was something that we really struggled with. How diverse should the 13 be? Should we go out of our way to make the list more diverse or deliberately diverse or should we let it reflect the people we choose and let the chips land where they will kind of approach. So just picking the 13, there was a lot of interesting discussion and debate and then more broadly there was this- always this tension between should the book be more biographical and narrative based, i.e. we make a point through story or should we dive into the research and the literature about leadership? Should we get a little bit more theoretical and academic and really kind of do a meta level synthesis of what all the literature about leadership tells us. And that was always a tug of war because we wanted to say something important about this thing we call leadership, but we also wanted to do it through a narrative form, right? And to get those two in the right balance was always a little bit of a tug of war.

BRYAN: 01:30:23 I imagine, as you discussed the weekly calls, daily calls and the Sunday call and stuff. Did you say daily calls? Did I hear that right?

JEFF: 01:30:30 So we had, yeah, we had actually- so we had the three co-authors and then we also had three research assistants who were helping. And so some collection of that group, usually led by Jay, would do a call every day, but at a minimum, all six of us would get on the phone for a big chunk of time. Usually 6:00 every Sunday morning because that was the only time you could really carve out as your own to go through everything that we had done that week and we would do in the coming week.

BRYAN: 01:31:07 And that was the whole- basically the schedule for 18 months. Like 76 weeks of Sunday morning calls at 6:00 AM. Wow.

JEFF: 01:31:17 It was pretty funny. We had a going-away dinner, one of our RAs, two of them actually, kind of as we were finishing up the final version of the manuscript, you know, got good job offers and went off to take those jobs, and so we had a dinner all six of us and one of them made- everybody kind of made gifts, or presented things to each other. One of them was a picture of a screenshot from our, you know, our video conference system of the six of us all on the screen together because usually people were dialing in 6:00 on Sunday morning, you don’t always get together physically. And so usually we’d be in on these, these video calls. And so it was a two by three tile of the six faces at their 6:00 AM, Sunday worst. I mean, it’s like, you know-

BRYAN: 01:32:11 That’s great.

JEFF: 01:32:11 Everybody’s basically in whatever they had been sleeping in, you know, and, not at your prime. Right. And just a classic representation of the journey. Yeah.

BRYAN: 01:32:24 Many people listening might say, well, you know, I’m just, I’m one person. I don’t have a research assistant. I don’t have co authors, you know, yeah, it’s easy when somebody’s got those kinds of resources and things like that. But what do you say to somebody that maybe doesn’t have, you know, that kind of team around them, but they still want to do what you’ve done, which is create a book that matters.

JEFF: 01:32:45 Yeah. And I, you know, in some ways, the more resources, the easier it sounds, but in some ways, if you’re your own author, you can make pretty good speed and headway because it’s just you. And one of the best things someone told me very early on in the process, actually two things was one, if you write a little bit every day, you’ll have a manuscript after a year. So just find some time when you’re at your peak during the day when you can write. Figure out what your daily, you know, rhythms are, find that time, make the time and just work a little bit every day. And it goes back to the power of kind of incremental thinking we talked about earlier. If you take that approach, if you don’t set out to write a manuscript but you just set out to write 500 words and you do that every day, you will have a manuscript over the course of a year. And so that was the first thing somebody told me. And the second thing that was really powerful is the power of a crappy first draft, which is a pretty well known kind of truth among authors. You can’t expect that the first version of anything is going to be worth anything. In fact, the only time you end up with great writing is if you start with really bad writing and then you just keep editing, you keep after it, and that gets pretty tedious and it’s difficult, but that’s how- that’s really how most great books are done is they start as a really crappy draft of something and it just gets crunched through an editor and so forth. And you can be your own editor to some extent. But those were the two most important pieces of information is to find that time everyday where you can devote your attention to this in a pretty kind of peak optimal way, and two, don’t be afraid to just let the first draft be really ugly. And that’s a great start.

BRYAN: 01:34:56 Yeah. You know, and I love that. I love those insights. And as I hear that, especially that second one, like basically to be willing to write a crappy first draft, what comes up for me is kind of this dance between the, first of all, the allure of perfectionism, right? So, okay, I wrote a crappy first draft. I redrafted, it’s a crappy second draft. I redrafted it’s a crappy third draft, like, how do you know when it’s done? That’s on the one end is how do you escape the trap of perfectionism, and on the other end is how do you persevere through the inner critic that we all have, like, oh, this is crap and it will never be good. So how do you walk- how do you successfully dance that dance?

JEFF: 01:35:38 Yeah.You know, you’re never done. So you’ve- at some point you’re going to let go of the draft and it’s going to get printed and bound and you’re still going to read it six months later and go, oh, I could have done that so much better. Or oh, I forgot to include this vignette, or there, you know, I would write that so much better if I- well, guess what, that’s not how the game’s played. At some point it’s the 80 percent solution or whatever percent it is, but it’s not 100. And that’s when the editor gets it and they’re gonna crank it two or three more percentage points and it’s still not going to be 100 percent solution and then it’s going to get printed and bound and that’s it. And you’re done. You know, and you’ve just got to get over the fact that at some point you let go of it. In terms of being your own worst critic, you know, that cuts both ways. You can be in love with something that most people are going to think, wow, that’s not that great, or you could really be agonizing over something that people are going to find beauty in that you were agonizing with. And so, in many ways you’ve gotta- the only way to really know is to put it out there, is you’ve got to take the risk of believing in yourself, writing what you believe and putting it out there, and then you find out and I don’t think there’s any way to get around that requirement.

BRYAN: 01:37:12 Yeah. This is one of those things, if you’re going to be a writer, that comes with the territory. I guess, right?

JEFF: 01:37:18 Yeah. And you’ve got to have a little bit of a thick skin because you know, no matter what, as soon as you put it out there, somebody is going to take issue with it. Not everybody’s going to think it’s great even if some people do.

BRYAN: 01:37:31 Yeah. In fact, one of the ways that that’s clear, I make this mistake sometimes, like- I say it’s a mistake, it’s not really a mistake, it’s just something I do- where I read the comments.

JEFF: 01:37:41 Oh yeah.

BRYAN: 01:37:42 About- right? Or the reviews. Do you do that, do you read your own reviews?

JEFF: 01:37:49 It’s a bad habit, it’s a bad habit.

BRYAN: 01:37:49 I think it’s totally natural.

JEFF: 01:37:51 It is, it is. I’ve talked-

BRYAN: 01:37:53 The reviews are pretty good.

JEFF: 01:37:55 Yeah, I know, I’ve talked to people who don’t, and you know, I’ve heard Hollywood actors who say they never watch a minute of themselves of anything that they’ve been filmed in because they just can’t stand to watch it, because it looks horrible to them and yet they can’t understand why everybody thinks it’s so great. And everybody I think suffers from a little bit of that. There’s something to be learned from paying attention to your critics for sure. But you gotta have thick skin because it’s not comfortable or easy. And if it’s going to be a productive exercise, you got to be able to read it, learn from it without getting dissuaded by it.

BRYAN: 01:38:35 Yeah, no doubt. So do you have any rituals that you follow when it comes to writing? Do you have certain slippers you wear, or a cup of tea you brew, or a candle you light or anything like that you do before you sit down to write or during your active writing?

JEFF: 01:38:53 Well, one is the time of day for sure. I have learned that time of day matters and you know, it’s, I can’t explain it, but for me, it’s the morning, some people it’s the evening or whatever. That’s the first thing, the second thing is that I don’t usually get ideas on what to write for when I sit down to write, and the ideas about what to write most often come during my jogs. So if I had a ritual, it would be to go for jogs, thinking about what I want to write, make sure I record in some note form at the end of the jog so I don’t lose it, whatever it was I came up with because I tend to get my best ideas during exercise, but then to then sit down and actually do the writing on those ideas the next morning or whatever, just as a basic ritual that’s worked well for me. And in other words the generation of the insight and then the actual drafting of the words on the page happen at separate times because you can’t sit down and write when I’m running, you know, not even dictation works well for me, although I’ve experimented with it. So it’s almost a two part ritual for me.

BRYAN: 01:40:12 Yeah. And on that topic, when it comes to capturing those ideas that come in, you know, like on the jogs, what software or tools, you know, maybe you’re an analog guy with a notebook and a pen, or have you found any specific apps or software or voice recorders or whatever, what tools and technology have been very useful to you?

JEFF: 01:40:34 So in this- there is one, you know, dictation software and Dragon in particular is something that became my friend because whether it was driving or jogging, you just can’t take notes. But if I have the idea and I don’t capture it, it’s gone. And sometimes it’s like gone, gone, like it doesn’t take long.

BRYAN: 01:40:56 Like a dream.

JEFF: 01:40:56 Yeah!

BRYAN: 01:40:57 It’s crazy.

JEFF: 01:40:58 And- it is and I’m the same way with dreams, that they’re there for about two milliseconds and then they’re gone, but if I dictate the idea, even if it’s almost indecipherable to the average reader, it will be meaningful to me. It’ll be enough to regenerate whatever it was that I had. So I try to use dictation software and at least just capture it in an email to myself and you know, with the subject line that then I can just consolidate them all and that becomes kind of my notebook for drafting.

BRYAN: 01:41:36 Yeah. And then in terms of other technology and process, what did you find worked as you collaborated? You know, as you researched, you collected stories, you made drafts, did you use Dropbox, Google Drive, you know, Sharepoints, something else, did you do like emails and- well, how did you coordinate all this different content?

JEFF: 01:41:57 We experimented with just about every solution there is, and because we had a multiple author, many person team and we had three coauthors and a six person team, we really relied on collaboration tools. We originally set out wanting to write in Scrivener, the software Scrivener because it’s a great, you know, it’s a great application for writers. It’s not yet optimized for multiple author situations. So in some ways we had to back away from Scrivener and we ended up using a combination of Google Docs, Microsoft Word, and so forth. One Drive, and it, you know, the software and the tools have not yet, I think, gotten to the point where we felt like there was a single golden solution for us. There were drawbacks to each one and we kept, you know, looking for the perfect way to collaborate on the writing and frankly it felt like we kept going back to old fashioned, get on the VTC and discuss it, throw it up on a Google Doc, throw it up on the screen. But man, there isn’t yet a perfect collaborative tool for that kind of situation.

BRYAN: 01:43:21 Okay. So my final question for the interview is, what are the qualities of a great sentence and how can we as writers craft more of them?

JEFF: 01:43:32 Well, you know, there’s a certain beauty in something that’s short and concise, you know, that old phrase, I would have written less if I had had more time stuck with us all the time, and I think having mercy on the reader who doesn’t need big words, doesn’t need words they have to look up and doesn’t need six words when two will do is something that I think that’s really, really hard. So I think short and simple, it- you know, kind of in that classic style, I enjoy that and I wish more authors felt comfortable writing in that way.

BRYAN: 01:44:19 And editors for the times the authors don’t.

JEFF: 01:44:23 Yeah, but it’s got to start with- it’s got to start with the author.

BRYAN: 01:44:27 Yeah, agreed. Agreed. Okay. Well, I know I said that was the last question, but I feel like what might be appropriate to sign off here with is if you have any final thoughts or encouragement for those listening. Maybe people who are in the middle of a project or they’re just at the- they’ve been on the threshold of one for a long time. Like what do you leave people with as inspiration or encouragement to get their own projects done and to make the difference that they want to make?

JEFF: 01:44:53 Yeah, you know, I think that you never know when you are going to have things come together or take a radical twist or turn or you’re going to be hit with an insight or a flash. It could be tomorrow. It could be next month. You could be sitting there for weeks thinking this is going nowhere or there’s nothing here and you could be totally wrong. And that moment of being proven totally wrong could be tomorrow. So all you can do is keep at it because my experience is eventually it’s going to come. It’s going to gel, it’s gonna come alive, the flash, the thing is gonna happen and the only way you’re going to get there is by persevering and it’s gonna feel like a lot of days of just beating your head against the keyboard or feeling like it’s just not there. And you’ve got to have faith in yourself and in the process that it’s going to come and to just stick with it because the only way you know for sure it isn’t is if you stop. Right?

BRYAN: 01:46:01 I love that. I’m- seriously, that’s really moving and I realized that’s just what I needed to hear today, from personally. So thank you. Thank you for that.

JEFF: 01:46:12 Maybe both of us.

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