I recently interviewed General Martin Dempsey on my podcast, Thirty Minute Mentors. Here is a transcript of our interview:

Adam: Our guest today served as Chairman of the Joint Chiefs of Staff, the highest ranking military officer of the United States Armed Forces and principal military adviser to the President, National Security Council, Homeland Security Council and Secretary of Defense over the course of a military career that spanned more than four decades. General Martin Dempsey commanded units at every level, including 42 months in combat, as part of Operation Desert Storm, and Operation Iraqi Freedom. Today, General Dempsey is the chairman of USA Basketball, and the author of the new book, No Time for Spectators: The Lessons that Matter Most from West Point to the West Wing. General Dempsey, thank you for joining us.

General Dempsey: Well, it's good to be here with you, Adam. Thank you.

Adam: What are the best lessons from your days at West Point? And what are the skills that you developed early on in your career that proved to be most valuable to your success?

General Dempsey: Wow. You're only going to get one question if I really... but I do think there are several things or at least a couple of I would mention right at the onset here. One of them is that looking backwards at it- I wouldn't claim to have known this looking forward as your West Point cadet- but looking back at it now. I do see that you accumulate experiences that inform each other if you let that, and what I mean by that is, in this Helter Skelter world, which seems to speed up every time a new device is invented, I think that you can kind of wish away what you're doing in order to get to the next thing, you know, whether it's the next job or the next promotion. And I think that one of the important lessons I hope comes out of the book is that, you know, you've got to be in the moment, you know, when you're given a job to do that job and in industry, if given another job, do that job. That would be one thing. And then the second, I would say is that you can't let either your successes or your failures, especially not your failures define you. Everyone fails, you know, some fail epically, and some fail modestly, but everyone experiences failures, and so on. You know, the ability to not get too enamored of yourself when you succeed or too down on yourself when you fail, I think is an important quality.

Adam: What do you consider the biggest failure of your career? And how do you bounce back from it? And what do you learn from that experience?

General Dempsey: If you're leading men in combat, and you lose and you take casualties, you suffer, killed in action, at some level that has to be seen as a failure, even though, believe me, I concede that the enemy, whatever enemy you're confronting, they get a vote. They're going to be trying as hard as they can to overcome you as you are to overcome them. And so you know it, but you do feel a sense of guilt and finding a way to, you know, to keep going in that circumstance. First of all, I think, allowing yourself to feel those emotions of loss and grief. Even though there's a Hollywood persona of the military leader that’s kind of stoic and oblivious to everything around them except succeeding at the mission. And I've never met anybody like that. And so I think I would have to put the ferry to bring everybody home from Iraq with me as kind of the top of the list, even though I have done things and said things and tried to continue to live, even in retirement, working hard for the families of the fallen. But that lingers, and so I think that as a military officer, that seems to me to be number one. And then secondly, you know, as you go through life, and, if you're especially if you are a trusted adviser to someone. And by the way, one of the themes of the book is that, you know, we're all followers and, and some cases, some of us become leaders, but you need to understand the attributes that define both ends of that relationship. The best or the most productive relationships are those where leaders and followers share common expectations of each other, and so on. Narrowing it down to your question about failures. You know, I've said often and in previous speeches and reflections of my time as Chairman, I never felt like we came up with any good options for stabilizing the situation in Syria. It's not that we didn't try, but it was a extraordinarily complex, fast changing environment with just horrible human suffering and great power involvement. You know, Russia was involved, Turkey was involved, Iran was involved. And of course, we were trying to find a way to be positively involved. I don't think we ever were able to give the kind of advice that would allow the President to find a credible, reliable, successful option. And you know, so, you know, to be honest with myself, I consider that to have been a failure but fortunately or unfortunately, Syria, at the time, and since is one of 12 just horrifically complicated and complex and unpredictable national security challenges. And so you know, I had to set that aside and try to resolve the others and be the best advisor I could be on the others. Says Chairman of the Joint Chiefs of Staff, “You're involved in the most important decisions facing the country, you're just sharing a few of those with listeners.” Life and death decisions with countless lives at stake. 

Adam: A couple of questions. What were the toughest decisions you had to make or advise President Obama to make? And can you describe your decision making process and any advice you have for listeners on the topic of decision making?

General Dempsey: Yeah, let me go to the last one. The end of your question, before I give examples of it, as you suggested at the beginning of your question is how do you make decisions? I'll tell you one of the things I learned in working for President Obama is how senior leaders- well, I mean, the most senior leader, in this case, makes decisions. And fundamentally, if you've, I can't see you, but if you're, you know, a lot of us wear glasses, and almost everybody I know has been to the eye doctor, and they put that kidney shaped device in front of your face and, and then they start flipping the filters or the lenses, you know, and they'll say, “Is this clear? Or is that clear? Number one, or number two, number three, or number four,?” And especially if you're like me, you say, “Oh, the heck with it, just give me the darn glasses,” because I can't at some point, you can't tell you know, which is the better vision. But to use that as a metaphor for how senior leaders make decisions, in the case of the President, you know, when he's facing complex decisions. By the way, all of the easy issues are peeled off before they get to a president. So when you're faced with that, that's when you need trusted advisors who come in and in their particular areas of expertise, they give advice. And so you know, back to the device in front of your face. One lens is foreign policy implications, another one is budget implications, and other is national security implications. Another is intelligence implications. And the lenses keep flipping. And then when the President believes- any senior leader, really- it seems to me that they've got the information they need, then they go back into the quiet of their office generally. And they make a decision based both on what they've learned, because learning is an important part of decision making. And then also what their experience tells them because most issues, they may not, you know, that thing about history, does it rhyme or does it repeat itself, but it does rhyme. And so they use their experiences. And then the last thing is they look in their heart and then try to align the decision with their character. I call it in the book, more accomplishment. More accomplishment gives you a general direction of travel. Well, that's kind of what your character does as well. So it's a combination of knowledge, experience, and character that allows leaders at every level to make the really hard decisions. So, now back to your two examples, you know, early in your career, you have the ability to learn, you don't have much experience, but you have a lot of character, you know? I mean, you're true, we all start our lives, less cynical than we end up and, and so you've got this kind of pent up belief system that you use. And, you know, I mean, all through my younger years as a military officer, I was using all three of those things, you know, what did I just learn? Have I ever experienced that before? Probably not early on. And then, okay, well, what is, you know, how does this decision I'm about to make align with what I believe and so that was that. And then when you get more senior, if you think of these S3 buckets, you start to, hopefully you keep filling the knowledge bucket. Although, frankly, Adam, I've found a lot of people as they matriculate in age, they become hardened in their beliefs. They become too confident in what they think they know. And they stop trying to learn. So they stopped filling that bucket. But you keep filling the experience bucket, obviously. And hopefully the character bucket is still a reliable compass for you. So I guess I would say, to summarize, we all make decisions using three things; knowledge, experience, and character. And you've got to keep filling each of those buckets if you want to make good decisions.

Adam: You were a key advisor to President Obama, but you didn't have a relationship with him until you were on the job. How did you build that relationship? And you touched on this a little bit, but what were the best lessons you learned from your time around President Obama?

General Dempsey: I teach a course here at Duke University to MBA students, second year MBA students. And the course is about how to be a trusted adviser. And, you know, initially the students are all kind of, well, why, why are you making me sit through a class on being a trusted advisor? Because you know, I'm going to be a CEO here shortly. No, I mean, really, I'm in and God loves Suzy and then the optimism, but I say, look, yeah, you probably aren't going to be a CEO, most of you, but you're not going to walk off campus. And, you know, people are going to fall over themselves to try to give you a company. So show you're probably going to be, you know, even if you're a financial advisor, you're a trusted adviser to the clients who count on you to shape their retirement savings, you know, that. And by the way, that's why I called the course Trusted Advisor and that’s how I get to your question, the thing you've got to do, if you hope to be a reliable, credible follower and advisor is you've got to build trust and it takes time.

You've heard this. I didn't make this phrase up, but it takes time to build trust, but you can lose it in seconds, really. And so it is I actually said about a campaign, to use a military term on how I would build, gain the trust of President Obama. And by the way, I didn't, I had to earn it. And by the way, it's a two way street, these relationships between leaders and followers. And, you know, I think that a good leader understands that he's got to earn that trust too. So in other words, it wasn't just me working to build trust with the President. I could tell that the President was also trying to build a positive, productive relationship with me as his military advisor. So he knew I could give him advice, even if I sensed it wasn't the advice he wanted to hear. You know what I mean? And so, one of the things you have to do is you've got to be truthful. I mean, you can't, you know, there's the old saying about, say it in the boardroom. This is a civilian phrase, but say it in the board boardroom, don't wait until you're out by the water cooler, and then start, you know, expounding on what you would have said if you'd had the courage to say in the room. And that's, you know, that's true, especially in someplace like the Situation Room. I mean, it's intimidating. And so you know, you have to, you have to learn to be concise. Back to my thing about learning, you got, first of all, you better be, you know, you better try to go to a meeting more prepared than anyone else, that should be the goal. And then secondly, you have to be concise, because presidents, you know, they just, they’re going from meeting to meeting and trip to trip and visit to visit. And so they’ve got a lot on their plate. And so you can't, you know, you can't say “Well, Mr. President, you've asked me a question about Afghanistan. Please settle back and I'll entertain you now with 50 PowerPoint slides for the next hour and a half.” I mean, that's just that's, that's just not gonna happen. And so you have to be knowledgeable. You have to be concise and I would add, articulate. And President Obama used to describe it as I want somebody in the room to surprise me. He'd say, “I've read all of the briefing materials that we distributed before this meeting, I actually read them. And so please don't just regurgitate those. What I want is somebody in the room to make some connections among the things you've read, and then surprise me with an idea,” and I thought that that was a great way to set the table for discussion. So I know that's how you build trust. You allow people to to express themselves and you don't shut them down. You know, even if it's not really what you need, you know, you have to be, especially if you're a president, it seems to me you have to demonstrate a certain degree of empathy with the person who's trying to help you do the right thing.

Adam: You rose to the top, literally, of the United States military. What are your best tips on how to rise within a large organization?

General Dempsey: Well, one of them I mentioned already, and that is don't, you know, to use another metaphor, don't get too far out over your skis. You know, I don't know if you're a skier. I used to be.

Adam: General Dempsey, I'm from LA born and raised in the San Fernando Valley, anything below 75 degrees and I'm sheltering in place. I can't handle it. So I'm not definitely not a skier. 

General Dempsey: Yeah, well, a skier would know if you get out over your skis, you're going back and you're, you're also, for you in LA, you know, you don't want to get out in front of your headlights. Okay. That's our follow up. You got that? 

Adam: Yeah.

General Dempsey: But anyway, you just have to do the job you're given, you know? You should, because you've been given it because apparently the organization needs you to do it. And so, you know, if you do that, and, by the way, that's not to say I don't think people should be ambitious. I mean, obviously, I didn't become the Chairman of the Joint Chiefs without a little ambition but, but ambition has to be ambition channeled to what's best for the organization, not necessarily what's best for you. And so, being in the moment, if you're in the meeting, be in the meeting, be there, because there's so many distractions in life today that can drag you elsewhere. You know, if you got your iPhone in your pocket in a meeting, and you probably have it on mute, but it'll buzz and you know, you're thinking to yourself, wow, I wonder who that was. That could really be an important message, you know, or it could be as a score of a baseball game, you know, you just don't know but, but it does distract you. So I think you have to make sure that you are clearly in the moment in whatever job you've been given to do. And then two other things: I actually think that humulity is a really critical attribute that allows a relationship between leaders and followers to be productive. Because if you're a leader and you're humble, then you're approachable. If you're a leader, and you're not, and you don't have any humility, you're just not going to be approachable. I mean, it seems to me anyway. And so I think you know- and by the way, if you're a follower, and you have a little humility, it means that you understand the gravity of the task you're given, and you're going to apply yourself to it. So I think humility, again, not not to the exclusion of ambition, but to compliment ambition is an important trait. And then the last thing I'll say is that the best leaders and followers that I've ever been around, just turned out to be good listeners as well. And I give you an example of that. I carried, while I was chairman and before actually when I became a general in 2001, I carried a card in my pocket because somebody suggested I do so and on the card was written, “When is the last time you let someone junior to you change your mind about something?” And the man suggested that I carry that card. He said every once in a while, just pull that card out and read it. And then think about literally, when is the last time you let somebody junior to you change your mind about something? If you can't answer that question, you're not a good listener. And unfortunately, listening is not a natural instinct for emotion. And so you have to work at it.

Adam: One of your core leadership principles is that the best leaders are also the best followers, which is really interesting. Can you expand on that and explain how all of us including those of us in leadership roles, maybe some of those MBAs who you were talking about, can become better followers?

General Dempsey: Well, first of all, you're probably not gonna be a great leader without passing through the hard work that it takes as a follower to get there, I mean, so pragmatically, I think we ought to think about how to be a good reliable, responsible teammate. Think about it as being a teammate. And so, you know, in the book I try to lay out, as you know, because you read a bit of it, but the, you know, I think, for example, character matters in the leader follower relationship, you both have to know that, that you can trust each other and character is the is the, you know, the signposts on the highway of life that leads to trust. And so I think character matters a lot. I talk about loyalty and understanding what it is, but also what it's not, you know? It's not a one way street. It's not appropriate for a leader to expect everyone around him or her to be loyal but not give loyalty in return. It's, as I describe it, it's kind of a two way street. And leaders and followers really have to, you know, they have to work at it so they don't collide with each other. You've seen the phrase in the book, it can't be on the issue of loyalty, it can't be that disagreement is considered disloyalty, I shouldn't say it can't be in the kind of relationships we ought to want to have among leaders and followers. Disagreements shouldn't be considered disloyalty until the decision is made. By the way, I can see that once a decision is made the leader, whoever it is, at whatever level has a reasonable expectation that the decision will be implemented and followed and executed. But prior to that disagreement it’s considered this loyalty. You're not going to have the opportunity to fill one of those buckets I talked about earlier, which is knowledge. And so, you know, those are the kind of things where I think, and there's others in the book, but there's a chapter called, you know, Be or Allow Responsible Rebelliousness. You know, if you think about it, most innovation in this world occurs with a little bit of rebelliousness, somebody pushing on the box or pushing on the edges. And the question is whether an organization can establish a climate where that little bit of responsible rebelliousness is encouraged. You're not going to see it listed on an organizational chart, you know. I doubt that even the most enlightened leaders- they are probably not going to say I want my employees to be rebellious. You know, that's hard for me to conceive. But it can be part of the culture. And it all kind of emanates from this idea that leaders and followers need to learn experience and have character.

Adam: You do a really, really phenomenal job laying it out in the book, but I wanted to know if you can maybe spend a couple of minutes with listeners sharing your defining principles of what makes a great leader and what can anyone do to become a better leader?

General Dempsey: Yeah, well, you know, you've heard that tried and true phrase; Bloom where you're planted. That's one part of becoming a great leader. By the way, a great leader is more likely to be one who history just happens to find and what I mean by that is I used to go to the service academies when I was the chief of the army and then subsequently with the Chairman of the Joint Chiefs of Staff, so I'd go to every year I'd go and talk to the senior classes of West Point, Annapolis, Air Force Academy, Merchant Marine Academy, and Coast Guard Academy. And when I would inevitably get a question from some, normally it was a freshman cadet, or midshipmen, and they would say, “Hey, how do you get to be the Chairman of the Joint Chiefs of Staff?” And I would, I'd always answer the question the same way I'd say “Well, first of all, if you're worried about that right now as a freshman cadets and midshipmen at West Point or Annapolis, you're never going to be the Chairman. I’ll just tell you right now that the way this works, the way this works is that history finds you, you know? I can't predict what national security challenges you'll have. Who could have predicted the depth of this pandemic, and its effect on military leaders? And so the best military leaders are the ones that kind of adapt from what they've learned about being members of the military, to what they now have to do in support of civil agencies and the American people. And so, history is gonna find a handful of those and later down the road history will, you know, we'll find a handful more. But here's the thing; if you're sitting in that audience of 1000 cadets or midshipmen, you don't know which one history is going to find. You just don't. And so it seems to me that it's incumbent on all of them. And this is what I tell them because you don't know which side of history you will be on. You have an obligation that you have accepted freely by volunteering to join our military, that you'll be ready if history finds. So you got you got to work, you know, you just gotta work it and you got to, you know, you got to keep learning and keep developing your character and keep accumulating experiences. So, you know, I think that in terms of summarizing how to your audience, you know, how do you become a better leader? I think that the best leaders that I've been around are, in fact, the ones that continue to learn that not only continue to learn, but insist that others help them continue to learn which then implies listening and humility, a certain empathy meaning, I think that leaders who call meetings and and simply jump right into the middle of the meeting without any human interaction beforehand or even something as simple as asking how someone's children are doing, and especially now when we're in the middle of all of this, all of this isolation, I just think, look, let me put it this way.; there is a book called Once an Eagle by Anton Myrer. And it's a book of fiction. It's about World War Two and it portrays two different kinds of leaders. One is extraordinary and is a West Pointer. He's unimaginably ambitious. He's dismissive of anyone else's intellect other than his own. I mean, he's just a despicable character. And it's unfortunate that they picked the West Pointer to be the despicable character, but the other, the other leader that's portrayed comes up through the ranks. His name is Sam Damon, and he's an unbelievably good leader. He's empathetic, he's humble. He's an active listener. He is a learner. He's all the things I've been describing. At the end of the book you've got a protege who says to him, a young captain and he's now a general, a young Captain in the system, you know, “General, one of the things I've learned as I've been around you is that I actually want to be like you,” which by the way is probably the highest compliment, you can pay a leader, you know? I would like to be the kind of leader you are. And he says, “So how do I do that? How do I become a general?” He said, “How do I become a leader like you?” And Sam Damon says, “Look, if it ever comes to a choice between being a good officer, or a good person, be a good person, and then let the rest of it take care of itself.” Maybe that's the best thing I could say, you know, in summary of all the different attributes that you've asked me about up till now, I think if everyone just had in mind that, you know, every day they would try to make a positive difference not only in their own life, but in the lives of others, and be just a good person, I think we'd have better leaders and followers. 

Adam: I love that and that's actually very much in line with my personal definition of success, which is this net positive impact you have in the lives of others. And I used to be one of those MBAs that you were describing, not from Duke, I have an MBA from UCLA. I wasn't very good at, and still, I'm not very good at Excel or PowerPoints. But I do believe that very strongly, at the end of the day, it is all about what kind of impact you can make in the lives of other people. Are the decisions you're making grounded in a place of goodness and a place of kindness? And if you can act with that level of intent? I'm with you, General. That's the best form of leadership. 

General Dempsey:Yeah.

Adam: How can leaders build a winning organizational culture?

General Dempsey: Well, I mean, you know, coming out of the military, certainly since 1989. With the fall of the Soviet Union, we've, you know, we've fundamentally been unrivaled, but what I tell military leaders still- I still speak at some of our continuing education programs for he military, but I'm also, you know, working a little bit with the NBA on leader development. And I'm the chairman of USA Basketball where we take elite players, men and women from age 16 up to the Olympics, and we send them off to international competition. And one of the things I always speak to them about is that we have two goals going into international competition, and they're equal. And that's the part that I think, initially, they don't really believe me, but I make sure they believe me by the time they're done. And what I tell them is, we want to win the gold medal, you know, I mean, if we're going into a competition, we want to win it. I think it was Bill Parcells, who, when asked that question said, “Look, if somebody's keeping score, I don't care what the game is, I want to win.” But the second thing and equal thing is, it's how you win, right? I mean, we want to we want to win in USA Basketball, and be the one that hears their national anthem played in the medal ceremony, but we also want the, whatever it is, 32 other countries, that have sent a team to represent their citizens to respect the fact that, you know, the way we carry ourselves on and off the court. And so the equal responsibilities for USA Basketball is winning, and also how we win. And I like to believe that's true of, you know, of most, most endeavors. And the other thing I tell them is, you know, it's hard to get to the top. So, you know, think about how long it took the United States military to be recognized as the preeminent military organization, potentially in history. But what I tell my military audiences is that it's hard to get there. It's harder to stay there. It's just harder to stay there. Because now you're the gold standard, if you will, and everybody is going to try to emulate you and then find places where you know you have vulnerabilities and exploit them and so, you know, that's a military example. But think about it in any walk of life, you know, whether it's academia or corporate America, you know, you're, you're always working hard to get to the top, then you often get to the top or near the top and you you become a little complacent and maybe satisfied and it doesn't take long before that creates problems. So I would say that the answer to your question Is that how you win is just as important as winning. Winning is important. How you win is important. And recognizing that you can't ever take success for granted is probably the third ingredient in the recipe.

Adam: Sounds like you might be a candidate to be the next Chairman or president of the Houston Astros.

General Dempsey: You know, I can't jump into baseball and you know, I'm just now mastering my jump shot. So, I got to stick with basketball but I tell you I've gained a lot of respect for professional sports. Both for their, you know, their ownership for their, their community, their kind of their social responsibility, you know, they genuinely feel connected to their communities and the athletes, you know, at least to the NBA, but I think also for others, you know, when they come into the NBA, the NBA makes you clear to them that you know that yes, they're going to make a great living doing something they love to do since they were kids. But they've got responsibilities that come with that. And I love that about it.

Adam: I should have rephrased my comment, which is, you should be the chairman of the Houston Astros. My last question is a little bit different. I wanted to ask you, given the gravity of your work throughout your military career, not only as Chairman of the Joint Chiefs of Staff, not only your time in combat, but your 41 years in the Army. How did you maintain your mental health and how do you maintain a work life balance? You talk a lot about your family, your life with your wife and your kids, how can we live happier and healthier lives?

General Dempsey: When I talk to people now about this period of Coronavirus, and when I'm talking, for example, to general managers of the NBA or something, I'll say, you know, look, this is obviously a period of uncertainty and unpredictability. But really don't forget that what your people are going through is actually confronting fear, you know, and it's fear about becoming ill, it's fear about whether they can, whether their lives will ever be the same, again. In terms of professional sports, it's fear about whether they'll be furloughed at some point, because, you know, we haven't been able to get back to play. And so what you're really having to do is help them deal with fear. I would say in answer to your question about maintaining your mental health is that's really what it's about. You have to find ways and people to help you confront the fear that you might fail, you know? You might fail to give the right advice to the president. You know, I testified before Congress 45 times, and in my four years, and I was really anxious about that, not because I was afraid of the senators or congressmen. Some of them were scary. But mostly, mostly what I was afraid of is that I would not be up to the task of giving them the kind of insights that they needed on, you know, how the military was doing, where are we ready? What's the human cost of prolonging conflict? And so, I had to surround myself with personal advisors, most actually, all of whom were much junior than me. And in a really interesting way, they became my mentors on the issue of maintaining my balance because they would often ask about things like work life balance, and in their asking, I had to actually deliver when otherwise I might have just blown right by it. And they're also great. They gave me great feedback if they thought that a particular piece that I had written or speech that I’d given or testimony that I'd given if they thought it was, maybe it wasn't pitch perfect, they wouldn't hesitate to say me, they were very respectful, but they wouldn't hesitate to tell me. And so I think the answer to your question of work life balance and maintaining kind of, let's call it emotional stability, and some really trying circumstances. You have to have in the army we call it a battle buddy, you know, you gotta have you got to have a battle buddy. Or in the Air Force we call it a wingman or in the Navy we call it a swim,buddy. Hopefully, that's your spouse. And then you add to that by surrounding yourself with people who you can count on to be truthful with you. You know, you've heard the phrase speaking truth to power, which is kind of a cliche, but it happens also to have some validity so that I don't know if that helps Adam, that's about as good as I can come up with on the moment here.

Adam: That's tremendous. And thank you so much for all the great insight and advice and thanks again for joining us. This was a pleasure.

General Dempsey: My pleasure. Good luck to you and your listeners as we work our way through this really an unimaginably challenging time.

Adam: Thanks again. It was a pleasure.