The Learning Leader Show With Ryan Hawk - 633: General Stanley McChrystal - In Pursuit of Greatness, High Standards, The Ranger Effect, Self-Discipline, White-Water Rafting, Obsession, & Making Choices That Define Your Life (On Character)

Episode Date: May 4, 2025

The Learning Leader Show with Ryan Hawk Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Go to www.InsightGlobal.com/LearningLeader Stanley McChrystal is a retired four-star general. Stan is the former commander of the nation's premier military counter-terrorism force, Joint Special Operations Command (also known as JSOC). His command included more than 150,000 troops from 45 allied countries. Since he retired from the Army, Stan has written multiple best-selling books including, Team of Teams, and most recently, On Character. The most crucial discipline is to think for yourself. To a sad degree, we're lazy. People comment on things they haven't watched or read, but have seen comments by others who align with their political party. They aren't thinking for themselves (this is why it's almost impossible to align completely with one political party for me). If you find yourself saying "I just do" or  "that's what I heard," that's not thinking. Being Obsessed – "I am convinced that few truly great achievements are reached by individuals with an impressive work-life balance, and the price of greatness, in a word, is great. In the end, I'm an advocate for obsession." The Ranger Effect – The value of unwavering standards.Created near the end of Vietnam when the Army had lowered its standards. They created 2 units of Rangers to raise the standard. It permeated the entire Army. How does a leader do this in Corporate America? Clearly establish expectations. You cannot have a "say-do" gap. The leader must demonstrate the values on a constant basis. BE what you want. Discipline to hold people accountable. "My major takeaway at almost 70 years old is conclusive. I wish I'd thought more, been more contemplative about my convictions, and been more deliberate about the person I sought to be." Stan's mom — she died on New Year's Day 1971 at age 45. Stan was 16. Had 6 kids. Mary Bright McChrystal. Writes about her in the civil rights chapter. "I accept no belief or claim to truth automatically or unconditionally." White Water Rafting – When the subject of America's involvement in Afghanistan arises, Stan is frequently asked, what he might do differently if given the chance to do it all over again. Answer: "Go white water rafting." In Patient Pursuit of Greatness – In the spring of 2012, Stan was teaching a leadership class at Yale. That's when he met their football coach, Tony Reno: "Not many things materially affect my trajectory. But this time was different. What was different? Coach Reno." Choosing to Lead – Leadership is not a title or position. It's a choice. "Embrace the suck" – "Why suck a little, when you can suck a lot?" Eat one meal a day. It's built on being undisciplined with food. If you only eat dinner, you can eat a lot for that one meal. Self-Discipline - Most important attribute for a leader. Wife Annie - Dependent on her. Kind, thoughtful, caring. Life/Career Advice: Have the discipline to decide want you want to be. Be intentional. LISTEN: Don't just talk. Be respectful. Don't be afraid to fail. Try it, get back up. Try again.  

This episode is brought to you by Insight Global. I love the leadership team and the people at Insight Global. Insight Global is a staffing and professional services company dedicated to being the light to the world around them. If you need to hire one person, hire a team of people, or transform your business through talent or technical services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. hiring can be tough, but hiring the right person can be magic.

Visit Insightglobal.com slash learning leader today to learn more. That's Insightglobal.com slash learning leader. Welcome to the Learning Leader Show. I am your host, Ryan Hawk. Thank you so much for being here. Go to learningleader.com for full show notes to all podcast. episodes. Now on to tonight's featured leader, the legendary Stanley McChrystal, as a retired four-star general. Stan is the former commander of the nation's premier military counterterrorism

force Joint Special Operations Command, also known as J-Soc. His command included more than 150,000 troops from 45 allied countries. since his retirement from the Army, Stan has written multiple bestselling books, including Team of Teams and most recently on character. During our conversation, we discuss the most critical attribute for a leader to possess. Why we should choose to do hard things. Why he only eats one meal a day, having high standards, why obsession is good, white water rafting,

and being in pursuit of greatness. We talk about that and so much more. Ladies and gentlemen, please enjoy my conversation with General Stanley McChrystal. I want to start by actually talking about your mom. I love that you wrote about her a few times in this later's book about character. And if you would, I don't want to share anything that I think about her yet, but I'd love to hear the impact her life and her. she had on you, especially because of the fact that unfortunately her time was cut short.

But what was it about your mom that impacted you so much in just about 16 years? Everybody's mother's special, but to me, mine was extraordinarily special. She had been raised in a southern family, and it was a good family, but her part of it didn't have any money. And her parents divorced. So she essentially, she and her sister were raised by her mother. And I'm not going to say it was a tough life, but it wasn't easy. And so my mother was strong-willed and in her own way ambitious.

She went to college, you know, when it was tough to do that, became a reporter. And then she met my father right at the end of World War II. And she was never going to marry a soldier, but she meets this lieutenant who's just graduated from West Point. In fact, she's asked if she wants to go on a doctor. double date with a West Pointer. And she was living down in Opelike, Alabama, and West Point, Georgia was not far away. And she says, I don't want to go out with a Georgia boy. And they go, no, no, no, he's this guy. And so she meets him, and my father falls in love, and then my father is assigned to Germany. And after about a year, as the story goes, he comes home to marry his southern

girl. Well, she didn't see it that way. She'd been dating other guys. In fact, she was pretty serious with another guy. And this lieutenant comes back and he goes, here I am to pick up my bride. They hadn't been formally engaged. But to pick up my bride and they have this two or three kind of awkward days. And finally, he asked her to drive over to Fort Benning with him because he needed to get some uniform items. And during the ride, he could. convinces her to marry him. Whoa. They get married like three days later, you know, in the, in the living room of her aunt's house. And then she, for the rest of her life, is married to this army officer, has six children. He goes to Korea. He goes to Vietnam twice. I mean,

she has all of the challenges, but she was always her own person. She loved to read. She got involved in politics. She was very involved in the civil rights movement. That's what inspired me about that. And she had me handing out political brochures for the Democratic Party in Arlington, Virginia, when I was a kid. I didn't even know the differences, really. But she was always doing something. And so, particularly with my father gone several times, she had this outsized influence on me. And of all the six children in the family. I'm probably kidding myself. But I thought I may have had the most special relationship with her. And we would talk about books and things. It was, it was really good. How did that impact you then at losing her at such a young age? Yeah. Significate. I was a junior in

high school and she got sick one day, actually New Year's Day. And they had not been out partying or anything. my parents were just home. She got sick mid-morning, and by like two in the morning, she was dead. Her kidneys had essentially failed. And so I remember it was just shock because you couldn't conceive it. She'd never been sick. We'd never talked about it. My father was not long back from his second tour in Vietnam,

and we always thought there was that opportunity. We never thought my mother could suddenly be gone. And I remember my father came back from, he was at Walter Reed Hospital when they were trying to save her. And he comes back to the house and here is this combat veteran, brand new brigadier general. And it's clear he's been crying. It was just hard to process. I had two younger brothers who were 10 and 6 at the time, so it was probably harder for them. but it was just hard for me to get my mind around it.

Maybe it was years later when I realized how much I missed having that relationship with her as I had gotten into college age and later, because I would have treasured the relationship I know I would have had with her. I appreciate you sharing that, General. I mean, I know how close I still am to my mom. I try to talk to her all the time still. I'm grateful for the opportunity. My parents moved to Florida during the winter months.

And in a way, like it kind of bums this out because we don't see them for like five to six months. But we're still so grateful to be so close to both my mom and my dad. So when I was reading about that, it kind of, I knew about it from previously talking to you, but it still crushed me, you know, and I felt for you in that moment. But I also thought of just how compassionate and generous and kind your wife, Annie is. And I know this from firsthand experience, and it's cool to read so much more about her in this latest book because you so graciously invited me to go to Gettysburg with the group, the students that you teach or you have taught the leadership class at Yale. And I know you regularly run to the battle site the morning of the official tour right at pre-dawn, right before sunrise. And I just so happened as you were in the front leading everybody to be kind of like in the middle and the back, right? next to Annie for a good portion of that run to Gettysburg. And I just thought, what a remarkably

kind and curious and thoughtful wife you have, man. So it just, it just neat to see that you go from your mom, this like impressive, independent woman. And then you find somebody like Annie to marry and spend your life with, man. It just seems like she's had such a massive impact on your life. You know, it's, you're kind to say that about her, but the other thing is we had our 48th wedding anniversary this week. Wow. And it's still special, but one of the things I've realized from watching my father and mother is how dependent I am on Annie. Not in a material way, because she's not a very good cook or anything like that. Oh, no.

But she's my buddy. And in many ways, I feel sort of vulnerable. You know, I always think that if I passed, okay, that's fine. She'd be fine. I'm not sure the same is true. There's an emotional dependence I have on her that I'm not even sure she appreciates. But it's a gift to have so many years together. But it's a, it's always a worry,

you realize how important they are to you. In the acknowledgement section of your most recent book, you write that this was kind of Annie's thing. It was her idea, right, to push you to write this. And I told you, prior to recording, I just spent a week in the Bahamas with my family on spring break, and I spent every morning with you. And it was an awesome way that my family's asleep.

I'm working out. I finished the workout on the elliptical. I'll just spend 20 minutes with General McChrystal reading his book to prepare for this conversation. I end up going for an hour, sometimes 90 minutes, just continuously reading because it's so good. You could tell it's your genuine real stories. What was it about these stories and Annie pushing you to get them out of your head onto the page and then publish them so that others could learn from them too? Yeah, as you get to a certain point in life, certain things become sort of central to the way you think. And for me,

character has become that. It is the idea that we have all of the politics in our world and policy arguments. We have personalities that dominate the airwaves and seemingly our lives. But the thing that really matters is our character and our personal character and our national character as a people. And as we talked about as I thought about each of these different issues, they all intersect in the idea that what I think matters and determines sort of our quality of life, and what we contribute is character. And so as I started to amass these ideas, I became convinced that I don't have the right answers to any questions,

but I think I have some of the right questions. And so what I'm trying to get people to do is ask themselves the same questions. And if we could have a national conversation on character, if we could all just step back from all the stupid stuff we talk about right now, if we could stop shouting and stop listening, but talk about character to think about it, talk about it, and demand character from ourselves and from each other. We could make a difference. 100% agree.

How realistic is it? I honestly don't watch TV anymore, Stan, when it comes to any of the networks. it's almost unbearable. And I feel like at times, am I putting my head in the sand? Like, should I not do that? Like, but then you watch it. And it's like, oh, I want to hear General Stanley McChrystal on those shows. I want to talk about character.

I don't want to hear with the shouting. I don't hear the arguing. I don't hear the, you got to go far to one end of the spectrum. It gets exhausting to the point where I just don't want to do it. What's the, what's the answer? Like, how do we get better at this? You know, Ryan, I don't know how many people have described almost the same thing that you have. It's almost like we've gone off the grid. We've gone out to live in the

wilderness and we want to be cut off from society because we're unhappy with what we're seeing. But we do it by changing how we interact with people, changing how we interact with news and whatnot. And that's dangerous, I think. One, because if we get in our own little echo chamber, we may not have the right ideas in that thing. I think that what we need to do is almost get a national coffee shop kind of dynamic going, where you've got places you can go and you are comfortable. It's not all the people who agree with you. It's not a chat room where everybody has a strong view that you have.

Instead, it's a place where you can talk and be heard, but also listen. But hear things you don't know. Be challenged in those things that you believe. Somebody's saying, well, you know, have you thought about this? And if at a national level we could do that, well, I mean, could start at the individual level. It could start inside organizations. But if it could become at the national level where we simply respect the idea, you know, the other person might not be wrong.

One of the things I learned in Iraq and Afghanistan was you go to war and you think, well, my side's good and their side's bad, and therefore that's why we're fighting them. And then you realize that had you had their life journey, you'd be on their side because that's your frame of reference. And so then you step back and say, well, if they're not necessarily wrong, am I necessarily right? And the question is, there's a question mark. And we need to question that. We're not right simply because we are this or that. It's like the idea that America is exceptional.

I really take exception to that because I think America is only exceptional if we are. We're only as good as we are right now. It's got nothing to do with our founding fathers and the people before us did good for them. But if we're not living up to a standard that makes us special, then we're not special. Yeah. Are you okay if I just like go through some of my highlights from the book and then we can kind of riff on them? Yeah. Okay.

At the beginning, you talk. about my major takeaway at almost 70 years old is conclusive. I wish I had thought more, been more contemplative about my convictions, and been more deliberate about the person I sought to be. I find you to be an incredibly thoughtful person. I have for many years of having the good fortune to know you. And it feels like, though, you're a harsh critic on yourself, that you are as thoughtful and a contemplative. Now, maybe you are more now than you used to be, and maybe that's what you regret, but I'm curious to hear about that major takeaway at almost 70 years old and being so conclusive about it. Yeah, and I think I probably am more now. You got more time as you get older.

But if you think about our lives, you go to school, you're taught certain things and you're tested on those things. You go through a church or whatever religion that you have and you are taught them things and you're asked to believe those things. And then in my case, I went to West Point and into the Army, and you're given a set of values, duty, honor, country, and other things that are framing your life. And then you're in an environment where you want to be confident, you want to be viewed as loyal and a team player. All of those things push you into accepting a set of beliefs and values, and it doesn't make them wrong, but you accept them. And then you get, But if you spend a lot of time reading philosophy and wondering about, you know, the great questions, people think you're frivolous.

Instead, you should be studying this and that and becoming an expert, or at least there's a certain trend that pushes you in that way. And it's only as you get further on that I started going, now, wait a minute, maybe the philosophers weren't all stupid. But, you know, I used to think that philosophers were smart people, but they weren't practical for me. They weren't helping me solve my problem right now. And in reality, in many cases, they make you think about the things that really do matter. And so when you do that, one of the things that comes to me is you suddenly realize it's not a set of things to learn because there are not a set of immutable facts. There are a set of questions that you have to decide what you think,

and we're all going to get slightly different answers to those questions. So I wish I'd been forced earlier. I think of, you know, a really classical education that might have forced me to read and think more broadly and answer those questions. have been helpful. I don't criticize what I got, but I certainly could have done better. You're right. I accept no belief or claim to truth automatically or unconditionally. It feels like you are really willing to think things through or do additional work. Come up with your own

thoughts and beliefs based on the work that you do. And it feels like not a lot of people do that. And you've written about this. Like people, people just say, well, they believe things or they say something because their side says it. Or will they say or they, they already claim this thing. So they just go along with it without doing their own work. And that's that's lazy.

Like we don't think for ourselves in a lot of places. People want to act like their original thinkers, but they're not actually thinking for themselves. And I feel like that's what you're challenging us to do in on character is do the work to actually think for yourself and come up with your own beliefs as opposed to just saying, well, my side says this, so I'm just going to go along with it. Yeah. As you remember, I write in the book just about a year ago when there was a state of the union addressed by the president, a friend of of mine asks his friends, so what'd you think about it? And they said, well, I think this, this, this. And he goes, well, you actually watched it? And they go, oh, no. And they had watched

pundits on TV the next day, or they read an account or social media. And all they're doing is regurgitating how somebody else interpreted it. And if we think about the danger, there's also the case in Afghanistan where young Afghan men would be taken into Pakistan into a series of madrasas and they'd be educated and they would be required to memorize the Quran. The Quran is written in Arabic. They don't speak Arabic. So they were memorizing the Quran in a language they didn't understand and then they were being schooled in what the Quran meant by the people, the talibs or the teachers who were teaching in the bedrasas. So essentially it's like somebody, telling you, okay, this is truth, accept this and go forward. Now, you sort of say, how could they be,

you know, willing to do that? That's stupid. And then we think of our own lives. How many things do we accept because somebody says it? And we've never really questioned that. And that's what I think that the danger is. This is the hard thing with me, like some of my friends, when we have spirited disagreements from time to time, because I think it's almost impossible to completely align with one of our two political parties. And I know you've written about this too, where you don't either, right? You have certain beliefs on certain things and they don't align on one side or the other. So that's whenever it doesn't matter what side to me, whenever I have one that's like,

this, this, this, this, this, I believe all this. And this is the thing. It's like how I don't see how you're being an independent thinker if you literally align with every single thing on one, regardless again, of what side you're on, I feel like if you're an independent thinker, you're probably going to have a mix of both. I think invariably. And that's the danger because on the one hand, we sort of know we should be independent thinkers. On the other hand, we want to be on a team. We want to put on a jersey. We want to feel like we've got people in our herd or our tribe or our team that respect us for being loyal members of the

team and those are in tension. It's tough. It's tough. I just like you write about the most crucial discipline is to think for ourselves and to a sad degree we're lazy and that's the story that people comment on things that don't actually read. I like that challenge. Like do that necessary work. Don't be lazy. Okay. I like this exercise. I've done it before myself and it really makes me think and that's that at times with your students at Yale, you would have them write their obituary. And as I said, this makes me really think about things. And actually, as I've written it, I've made it aspirational. I want to live up to make these things true so that if it's being read, let's say, by one

of my children, that those things that she's reading are accurate, right? And so I write it in a way to live up to these things. What have you learned from doing that exercise, both for yourself as well as with your students at Yale? I think it's a really valuable exercise because it forces you to think. first about those concrete accomplishments that most obituaries at least list you know did this did this did this but then you think it's not always captured an obituary it's often in the testimonial at a memorial service somebody describes

Ryan and they go this is the kind of man that he was and I think how would I want to be described and if my granddaughters one of my granddaughters one of my grand daughters was doing it. How would I want them to tell people about their relationship with me and what they had concluded? And you'd want them not just to be, you know, adoring that they loved you, but you'd want them to pick out some things that, as I described my parents, in my entire upbringing, I never saw my father and mother do anything wrong. And what I mean by that, they never robbed a bank or anything. Of course, I never saw them take a parking place that they shouldn't have. I never saw them keep excess change back. They may have fought between each other.

I never saw it. I never saw them do anything that I wouldn't be proud to emulate today. That's pretty amazing. They were human beings. They weren't 10 feet tall. But the reality is they lived a standard that I still admire. I would love to have somebody be able to say even half of that about me. Self-discipline. I know you to be a very disciplined person. You're a four-star general. You don't get to a position like that, probably without quite a bit of discipline.

What does it mean to have self-discipline to you? Yeah, I think it is the single most important quality for a leader and in some ways for a person because assuming you can figure what kind of person you want to be. and what your responsibilities are, you then have to pair that with the self-discipline to actually do it. Most of us know how to be a good leader, for example. We know how to treat people, we know how to interact, we know how to reach decisions, but we don't always do it.

We find ourselves treating people poorly or any number of things when we're tired or we're impatient or we're emotional. And the self-discipline part doesn't mean you don't have baser instincts. You might be greedy, you might be all of those things, but you don't act on it because you know what you should do. George Washington was famous. He had this towering temper. But the reality is they only really could tell because they would almost see him holding it in check.

And so the ability to be able to tell. ability to force yourself to do things in alignment with what you've decided your values are, I think is just critical. One of the, I think, interesting quirks about you. I don't know if it's a quirk. It's more of it. I think it's a discipline thing is you don't. I got a lot of them.

Well, you only eat dinner. You don't eat breakfast and lunch, right? And you've been doing this intermittent fasting long before it was cool, right? Can you talk about this element of the fact that you only eat dinner? You know, it's funny, I could do some heinous crime. But if somebody interviewed me, the first thing that asked me about, they go, you only one meal a day? So it's turned out to be, you know, pretty valuable.

Yeah. Particularly if I ever commit a big crime. But when I was a lieutenant, I thought I was getting fat. And so I started running a lot. And then I started eating just one meal a day. And it's really, I hate to admit this, particularly on here. it's a reflection of a lack of self-discipline because some people can go and they can eat

half a grapefruit for breakfast and they can eat some very disciplined little thing at lunch and the same at dinner, I can't do that. When I go to a meal, I've gotta reach my arms out and eat everything that I can reach. And so what I've learned is, I can only do that once a day. And I've also learned that I have to defer gratification

to late in the day. So I always work out first thing in the morning, because that's going to be the hardest thing I do all day. And then if I have hard work, I try to do that. And I try to make my day. So dinner is sort of my reward. And then when I get to dinner, even at my age now, I can kind of eat whatever I want because I haven't eaten anything else.

Now, contrast this with my wife Annie, who you know, she eats like seven times a day. She's tiny. I mean, she's like 120 pounds, you know, so I can't say what her weight is. She's tiny and soaking wet, as you know. but she eats all the time and it just kills me. Are you hungry? Like, I mean, it's 126 in the afternoon.

Are you hungry right now? I've been chewing on my forearm between, no. No, I kind of don't get hungry because I psychologically decide I'm not. It's funny. Seriously? Is that a thing? I think so. I'm not sure.

I know that if I eat lunch, my body assumes it was dinner and it then decides it's time to go to bed. So if I eat lunch, days over. But like you honestly, you're not hungry right now. Some days I will get very, very hungry in the middle of the day. Usually if I didn't eat enough the night before or something, and my body will scream, eat. And I'll eat something, just pretzels or something because, but normally, no, I'm fine.

Gotcha. You have a, I think it was a poster hanging or picture hanging up in your garage that says, embrace the suck, followed by a quote that says, why suck a little when you can suck a lot? What is that in reference to? Yeah. I spent my career in the military, but I spent much of it in the Rangers. And in the Rangers, there was this, it wasn't stoicism. It was something beyond that.

It was you sort of celebrate that your life is hard and you feel sorry for yourself. and you use it as a moral superiority over other people. You know, look how much I suck. Now, you think that that puts you on the moral high ground. Most people are laughing at you, but the reality is what we did is we made our lives hard. Now, that was for that business, it was good, because what you did is you learned to put up with privation

and difficult things and to do more. And so we would do these training exercises, and we would make them literally as hard as we could. We'd do some things where you didn't sleep for 72 hours. You ate almost nothing. You're out in ridiculous weather. And it was all designed to push you to this point that says, no human can go beyond this,

and then you go beyond this and you convince yourself as a unit how good you are. And so it's got great value. But it also becomes something that's pretty funny. And when you saw it in my garage, it's got a photograph of me standing in this, you know, blinding snowstorm. And we parachuted into Yakima, Washington. And then we'd done this road march to get to this position. And it started snowing. And it was, you know, just kind of crazy negative.

But at that time, everybody starts joking with each other. It's funny. Instead of getting grim face, everybody tries to outdo themselves on how pleasant and funny. and funny it can be. And so that's when that's saying, that's the first time I heard it. Somebody came up to me and says, hey, sir, why suck a little?

When you could suck a lot. And it sort of captured the moment. What do you think, though, let's say people outside the military, someone like me, something as little as like, take the stairs, right? I was just in an airport yesterday.

I take the stairs instead of the escalator. In all these little moments in life, certainly waking up fasted workouts, lifting, running, all that stuff, is choosing, I think, voluntary hardship. Because in my mind, and I'd be curious, I know this is a big part of training in the military, but I want to relate it to outside of the military.

In my mind, I want to be choosing the harder path on a regular basis to prepare me for the inevitable adversity that will strike. I don't know what it's going to be, but I know it will be something and it will keep coming, whatever that adversity will be. I want to be as prepared as possible to deal with it by doing the things that are hard, right? So how have you applied that to your life

by choosing the tough path as a form of preparation for the adversity that will inevitably strike? Yeah, I completely agree with you. West Point's cadet prayer has a saying says, Lord, help me choose the harder right instead of the easier wrong. Now, they were talking in moral sense, but the reality is I think, you know, you don't have to hit yourself in the head with the hammer every day. So it's not to the point

of ridiculous. But I do think that doing those things that are harder that have value for you, like taking the stairs, like getting up early, like foregoing some of the guilty pleasures that you could do completely, I think it's a discipline that's of great value in everything you do. Okay. Being obsessed. I love that you wrote about this. I've been kind of obsessed with obsession over the last few months. Been reading about it, studying others, speaking with a few CEOs who are really big on this idea of obsession, hiring for obsession. And there are some potential downside.

But you said, I'm convinced that few truly great achievements are reached by individuals with an impressive work life balance. And the price of greatness in a word is great. and you said you're an advocate for obsession. Can you talk more about this idea of obsession and the price of greatness being great? Yeah, Ryan, I think you and I are very aligned on this one. There are just things that take a huge amount of effort. If you think if you want to be really good at something,

if you want to be an Olympic level competitor as an athlete, if you want to be a great artist, if you want to be almost anything, it takes a tremendous amount of, of time and practice and focus, and that reaches a level of obsession. I think that almost anyone who is world class at business or anything is obsessed.

Now the downside of that is there's a cost, as we say, it's a cost to the individual, and there's a cost to the people around you. There's a cost to your family, there's a cost to work-life balance. And so I don't think everybody ever can or will be completely obsessed. But the reality is, I know I am. I actually want to work with people who are. I want to be around people who are obsessed, maybe about just the good things, you know,

accomplishing certain things, not about, you know, just obtaining wealth or something like that. But I think that that outsized commitment is a value to us. And I actually think that the outlier in our society, the very successful people are, and we'd be better if more people were. What are you obsessed about? Yeah, I'm 70. I'm still working full-time, still leading my company, just wrote my fifth book. I don't know what it is, but it's maybe it's this obsession that I have to stay relevant, not on a national level in the news relevant, but I have to. to stay relevant in life. I've got to be an important part of the company I'm in. I have to be

an important part of my family. I have to not be sitting on the sidelines. And so to me, now that changes over life because what I do now is very different for what I did in the military or later. But the reality is I don't want to be a spectator. I don't want to be someone that doesn't really matter anymore. Do you think you'll ever retire from the McChrystal group. Yeah, I think they're plotting right now while I'm in here recording this to have it and retire me. Yeah, that's a great question. Not in the very near term. As long as I think that I can contribute to this organization to make it stronger, move better, and I'm physically able, I don't intend to because I like it. It's fun. I love to hear that. It's funny because I just recently

got a question from my financial advisor. He's like, well, what age do you want to retire? I was like, retire, I'm doing the exact thing that I'm obsessed about, that I love more than anything. Why would I ever want to stop? I mean, the only way I would stop is if like people just don't allow me, which it's my own thing. So I get to make that choice. I'm like never, never. Why would I ever?

I mean, my life, my mind could change. But I feel like you're kind of doing the thing you're meant to do at this stage, which has help people become more effective leaders. Why stop? You know? Yeah, I agree. I think there's a lot of people who today who retire because they want to and love it, and that's great for them.

There's a lot of people who retire simply because you hit a certain age and all your peers think you should retire. And I wish that our society would be just a little more open about that and say, as long as you can contribute in some ways, you ought to be welcomed to do that. Yeah. Gettysburg. I already mentioned it once because I was so fortunate to be able to be with you on one of those many trips that you've taken. And you wrote about Gettysburg multiple times in and on character, your most recent book.

What is it about Gettysburg that is so special to you and the learnings that you take each time you go? Yeah. A lot of people think about Gettysburg just as, of course, a big battle. And it was. But there are several things that important to me. First, it is a battlefield that is very similar to the ground as it was in 1863. So for a soldier or for anyone, you can go to the ground and the ground. and the ground will speak to you.

The things that happen there become pretty evident because as you look at Cemetery Ridge and Cemetery Ridge and Culp's Hill and the different things, you can immediately picture, okay, I get why things happen that way. The next is it was fought by two armies who had both been at war for about two years.

They had started as small groups of trained soldiers surrounded by a bunch of completely untrained volunteers, but by the summer of 1863, they were now hardened veterans on both sides. They knew the horror of war, they knew the danger, and for the case of the Battle of Gettysburg, they knew that this could be the deciding battle of the war. They had hit a point where it was pretty evident that if the North had been badly defeated, it might have caused the North to give up to decide it wasn't worth it. And if they could have destroyed Robert Lee's army,

could have been decisive at the time. So both sides went to that battle knowing it could be the decisive moment and point in the war. And then finally, there were a series of leadership decisions that were made on the field, not just big strategic decisions, but relationship-based decisions. There's the moment when General John Buford sends back and asks the Corps commander, coming up, John Reynolds, to hurry, bring his corps up. And a 37-year-old cavalry officer, Buford, had committed the Army of the Potomac to a place and battle that he hadn't been ordered to do.

He'd used his judgment. He'd sent back, he says, I think I found the right place. Please come up and support me. Those are pivotal moments in American history. And here's a guy who dies six months later, essentially of exhaustion. And we don't forget them in American history, but I'm not sure we always understand that kind of contribution as completely as we could.

What about Joshua Lawrence Chamberlain and his story? I can't get enough of it. I just read it and reread it. And you've touched on it. We talked about it when we were there. I just love to hear you tell that again. Yeah. Here's Joshua Lawrence Chamberlain.

And he's been a soldier for about a year. He'd been a professor at Bowden College. He's got the 20th Maine that's less than 300 soldiers. But they are brought up to the battlefield. The Union Army's like it long slinky and it's moving up and they're not at the back of it, but they're partway through. And so they get to Gettysburg, not on the first day, but on the second day of the battle. And they can hear the cannon.

They know a battle is going on and they're directed to go onto this hill, a little roundtop. They can't see the rest of the battlefield. They're in the woods. They're at the left flank of the Union line. And they're given this order that says, you're the left flank, you cannot leave this position. You have to hold, or the whole Union Army will cave in. He can't really see anything else except he knows the Confederates are about to attack. And so he puts his people in position, maybe the most famous defense in American Army history.

It gets attacked by the 15th Alabama several times. and then when his men are just running out of ammunition, he launches a bayonet charge downhill to push him away and holds. You know, here's a guy who wasn't a trained soldier, although he was a smart guy and a student of it, becomes three times governor of Maine, Medal of Honor winner, just sort of an extraordinary personality, but it's the person in the moment,

or I should say the people in the moment, because he wasn't alone. So good. I want to talk about having high standards or the value of unwavering standards. This is called the Ranger effect. Again, a non-military guy talking to one of the ultimate military leaders of our generation. But I think where we are aligned is if we're going to do it, I want to give maximum effort and expect excellence of myself, first and foremost, and then of everyone else. Or we're not going to do it. Right. And this is, idea of having high standards for whatever it is you choose to do, the Ranger effect. Can you go deeper in this value of unwavering high standards? Sure. The Rangers go back in American history and they were in World War II and Korea and Vietnam, but then they have been disbanded. And in 1973, General Creighton Abrams, Chief of Staff of the Army, decides to form two Ranger battains. And one belief was that he was forming these special units for raids and missions.

He was really forming two units because near the end of the Vietnam War, the standards of the U.S. Army had deteriorated badly. There were integrity problems. There were discipline problems. There were training problems. The Army was a shell of itself. And so he decided to create two units and have them do everything they did to the highest possible. standard. And that's what happened. They wrote an Abrams charter which basically charged the units to be the best units of their kind. And so the Rangers did that. They had more severe uniform standards, meaning higher standards expected. They had some more haircuts, discipline. Everything was done just to the penultimate standard. And it had this extraordinary effect. The people in the organization raised their own expectations of themselves. The unit held each other accountable

because you're in this and it was a difficult place to serve because if you put your hands in your pockets, some person, even junior, do you, would go, hey, sir, we don't do that. And it was just amazing. And those standards became emulated across the army. I was able to join the Rangers as a captain. And when I got there, I'd expect that everybody was going to be 10 feet tall, you know, square jawed, brilliant. And they weren't. They were just normal people who lived to a higher standard by choice. And the difference between the Rangers and every other unit was simply that expectation in those standards. And so over time, the rest of the Army, in places they didn't even know they were doing it, were emulating the Rangers. And so one

organization that became a regiment later really had this effect across an entire organization, and I would argue some armies of other nations as well. When you're working with leaders, let's say in corporate America, a Fortune 500 company, for example, and you want to bring some of that ranger mentality of having very high expectations and setting the standard and holding the line, right, all of those things, how do you do it? How do you utilize what you learned as a ranger and leading rangers and leading everyone, really, to then doing that in a corporate environment. It's harder than it seems.

The first thing is in a corporate environment, what's meant by higher standards is different than in the military, not on things like integrity and character and level of work, but on uniforms and things like that, obviously. But you can set, you start by clearly, establishing what those expectations are. And sometimes we write down lists of the values of, you know, the company. And the great danger is you put these values down and then what you have said is different from what people see you do. And you get what we call a say-do gap. And once you get a

say-do gap, then that just becomes a poster on the wall that people don't respect. So it starts with the leader demonstrating those values on a constant basis. And I emphasize constant because we sometimes think I'm going to be a leader when I'm leading by example. So I'm going to comb my hair and brush my teeth, put my best clothes on, and go out and lead. But the reality is you lead every moment of every day because your people are watching everything. How you act, how you interact with people. And so your first opportunity is is to be what you want. And then they will, if you are a good leader,

they will want to be as much like you as they are capable of being. The second is the discipline to hold people to account. And that's probably the hardest part, particularly in a corporate environment, because if you come in and you say, I want this, this, this, and we're going to do it this way, you can seem like an unrealistic jerk.

And people get shy about demanding standards. They get shy about telling people to do it over if it's not done well enough, that sort of thing. And the problem is that sets a new lower standard. As soon as you accept lower standards, that's it. So it really takes a little courage to get out in front of people both to demonstrate the behaviors, but then to demand other people to do it. You're getting there when people demand each other meet the standard. It's amazing how that works. Probably in the military, certainly on a football team.

I know this from first and experience. People say like, what's the biggest? I've been on winning teams and losing teams, unfortunately. But fortunately, I learned from those situations, which were, what's the biggest difference between the winning teams and losing teams? I will tell you, I think, number one, is that the winning teams, the players raise the standards and held each other accountable. the losing teams, the coaches tried to hold the players accountable and the players did not hold each other accountable.

And that was the difference. That was the biggest difference. And that's as a leader, that's what we're trying to create, right? It's an environment where you set the standard, you lead from the front when it comes to living up to those very high standards. There is no say-do gap, right? You live out those values. And then you would hope that then the team would first. follow, right? The team would want to live up to those standards and then hold others accountable

when they're not living up to them. You know, I love that rhyme because just two weeks ago, we took the Yale football team, the rising seniors to Gettysburg. And we do that every year. And what we do is we take them to Gettysburg for it's really just two days. And the first night there, we have a dinner and I give a pitch on the battle and talk about different things. And then we spend the rest of the evening, myself and there's some former military and CIA guys who go help. The team talks to each other, these future seniors, talk to each other about what they want from each other for the next year. What they're going to do as leaders of the team, what standards they want to hold each other to, things that may have been bothering them for the last three years, we urge them to sort of get out.

And after about an hour of that, Coach Reno, who's an extraordinary coach of Yale football, we leave and the team stays in there. And they typically stay three or four more hours. And they literally just have this session between themselves of raw honesty. And they leave sort of locking arms saying, this is what we're going to be as leaders for the team the following year. And I would tell you, of course, Yale's been doing. really well over the last decade. I can't claim it's us, but I am proud that we've been a part

of helping shape that culture. In your chapter titled Inpatient Pursuit of Greatness, I think it was 2012 when you first met coach Tony Reno. And I think you wrote, not many things, I like this line, not many things materially affect my trajectory, but this time was different. And I was like, whoa, what was different? And you said it was coach Tony Reno. What is it about him that makes him so special and such a great leader for the Yale football team. Well, you want to think of an iconic football coach is this big personality who just pushes. Coach Reno is a humble guy, but obviously very competent. But when he first took that job, he said, I want to have a leadership development culture.

And I'd ask, he asked me and another guy to help him. And the beauty is most people who do that, they come in and they do it for, for a couple of months, and then they go on to a new shiny thing or a new initiative. He's done it now for more than a decade, and it's consistent. And he is calm, he is demanding, he is sort of the steady force that moves Yale football along. And so now when he goes to recruit young men to come play football at Yale, he can look at their parents and he can say, the thing your son is going to get most of the way, you're

from this experience is leadership. They're going to get a Yale degree. They're going to get to play football. Those are both good, but they are going to be built into leaders. And boy, that's quite a value proposition. I met a few of those football players when I was at Gettysburg, and I was blown away. I kept in touch with a number of them afterwards because I had a kinship with the football guys,

of course. And it was just, I'm like, these guys are on another level. Like, I don't know if they fully realize how lucky. I mean, some of them did. They had really good perspective. but someone like, I don't realize, know if you realize how lucky you are that you have great coach, you're being led here by General Stanley McChrystal in a leadership class.

Like, man, the trajectory of those people are set up right. Okay, I think this other part was fascinating, and it actually makes me want to do this adventure. You said when the subject of America's involvement in Afghanistan arises, you are frequently asked what you might do differently if given a chance to do it all over again. And you said your answer is, go white water rafting. What's that all about? Yeah. You know, when you do anything that's hard,

whether it's start a business or wage a war, it's going to get difficult. And all of the bonds between the key people doing it are going to be strained. So with the wisdom of hindsight, I realized that, and I'm serious about this, if we could do it all over again, and they asked my recommendation. I had the president, secretary of defense, chairman of the joint chiefs, the general on the ground, director of the CIA, the key people go whitewater rafting and not talk about the war, drink a lot of beer, talk about whitewater rafting, and develop relationships so that when it is tested later, when you're several thousand miles away and something comes out in the newspaper that said, General Crystal did this, they can go, now wait a minute, I know.

know him. And that doesn't align with the guy that I knew. I think that those relationships, you know, if we had a war impending and they went off whitewater rafting, a lot of media would say it's a waste of time. This is a boondoggle. Important leaders ought to be studying maps. I would argue the most important thing will be the sinew of those relationships. And so, it's key. Well, I'm curious about that, General, because I work with leadership teams out. It's part of the thing that's branched off from this podcast.

And sometimes we'll talk about those things. We'll do improv. We'll do these things that people think of like, why are you doing that? Like, why are you wasting this time? You should be teaching us leadership. And I've been criticized because I'll bring in others to help me with these areas that they're specialists at. And that would be going on challenging hikes. Like I mentioned improv, these things that are uncomfortable.

And at times they even have been said, hey, can you stop doing those things that are time-wasters and just get in the classroom and teach us leadership. And I get in these kind of disagreement arguments. And sometimes they don't even want to work with us anymore. And I'm blown away by that. Because like if here are a four star general saying we should have gotten the president of the United States, the most powerful person in the world, CIA, the four star general, we should have went whitewater rafting.

If you're saying it, I don't feel like there's any way that that could not be accurate when it comes to like building a group of cohesiveness of doing something challenging together. We just learn it from experience in life, Ryan. You know it's sports teams, anything, any group that's going to have to be committed each other building those bonds pays dividends. It really does. Leadership is a choice, right?

It's not a title. It's not a position. And I feel like this is so good, especially coming from a guy like you, right, who had the position of leading thousands and thousands of people, of having immense power. And yet you, of all people still say, no, no, no, that didn't make. a leader, right? Like, leadership's a choice, and anybody can choose to do that. Can you go deeper on the fact that it's not a positional thing? It's not a rank, right? It's not a title, but leadership is a choice. Yeah, you have sometimes management authority or direction authority because of your position,

and so you can give orders, you can set up schedules, whatever is involved in that. But leadership's a bit different. Leadership is getting people to want to do something. that they wouldn't otherwise do. In the case of the military, you're asking them to go into harm's way, and that's not a natural thing. In a football team, you're asking them to work harder than they would like to work, to beat their body up at key moments and be committed, and you do that through leadership. We sometimes get it confused with monetary incentives or other things. Leadership, I think, is more primal than that. It is you reach in and you inspire, you build in somebody a willingness and a desire to do something. And that takes commitment on the leader's part. It's harder. It's less

convenient. It's more emotional because sometimes you'll really throw yourself into trying to lead a person or a group and it just doesn't work. And it can be really difficult on the leader because you do invest so much, but ultimately it's still the most rewarding thing that I've ever found. And all the things you do with your business, Stan, not talking family stuff now, let's talk work stuff. What is your favorite thing to do work-wise, writing, speaking, podcast? What is your favorite element of your work now? Inside my company, I like helping. I've got some leaders right below my level. I'm the CEO, but I've got people who kind of really run the place. I love sort of helping and coaching them do that, not to make the decisions, but helping them. We're consultants,

and so I spend a lot of my time with clients who are trying to wrestle with really difficult problems about reshaping their country or company. We're not the kind of consultants that come in and do big reorganization plans for you. We help people lead differently. We help them make decisions better. We help them communicate better. And if you can help people do that, You suddenly see these terrific outcomes. And that's, yeah, that's rewarding. Love it. One more before we run.

Your meeting was, let's say, a Yale graduate, right? Or anybody who's a recent college grad and they're like, General McChrystal, man, I want to leave a dent in the world in a positive way. I want to do good. I want to make these good choices. I want to have high character. What are some general pieces of life slash career advice you give to that person? Yeah, and I think a lot about this.

The first is self-discipline. Decide what kind of person you want to be and then try to hold yourself to that. Now, you'll have ups and downs. All of us do. But the reality is if you think, if you're intentional about that, and it's not what position you want to hold, it's what you want your obituary to say. You know, it's the more qualitative part. The second part is listen.

You know, we get an awful in a hurry and we want to, we're put in a position where we're in charge of a few people and we want to talk. And the reality is, in most cases, those people know more than you do because they've been around longer. So listen, and it's not just you learn a lot, but it's also respectful. If you respect somebody's expertise and experience, it's amazing the loyalty that that will build up. And then the last is, don't. Don't be timid about what you try to do. We sometimes worry about failing. You know, I was always scared to ask girls out on dates and I think most of us are because

we're introverted and whatnot. But the worst that can happen is you can fail. And if you think about most, if you're free climbing El Capitan and you fail, that's a problem. If you start a business and you fail, as long as you didn't lie, cheat or steal, so what? start another business. If you start a diet and you can't keep it, that's okay. Start another one. And so I guess that's what I tell you.

Don't be afraid to try to do more than you think you can because you'll surprise yourself. Love it. Love it. The new book is called On Character Choices That Define a Life. You have been speaking to me for the past week by me getting to read this book every morning while on vacation, it was the best. I absolutely love it. I highly, highly, highly recommend

get on character and read choices that define life. It's so good. General McChrystal, thanks again for coming back and being here, and I know we will continue our dialogue as we both progress. We'll do it again, Ryan. I look forward to it. Thank you so much.

It is the end of the podcast club. Thank you for being a member of the end of the podcast club. If you are, send me a note, Ryan at learningleader.com. Let me know you learned from this great conversation with four-star General Stanley McChrystal. A few takeaways from my notes. The most crucial discipline is to think for yourself. To a sad degree, we are lazy.

People comment on things they haven't watched or read, but have seen comments by others who align with their political party. They aren't thinking for themselves. This is why it's almost impossible for me to align completely. with one party or the other because I believe certain elements from both. And then if you find yourself saying, I just do or that's what I heard, you are not thinking for yourself. Next, being obsessed.

Stan says, I am convinced that few truly great achievements are reached by individuals with an impressive work-life balance. And the price of greatness in a word is great. Great. Stan says, I am an advocate for obsession. Me too. I want to be surrounded by people who are obsessed, who are deeply passionate about the thing they are doing. Then the Ranger effect, the value of unwavering standards. This was created near the end of the Vietnam War when the army, their standards did not rise or stay at the level they needed to be. So they created two units of Rangers to raise the standard.

And the cool thing about it is it permeated the entire army. How does a leader do this in corporate America? You have to clearly establish expectations. You cannot have a, quote, say, do gap. The leader must demonstrate the values on a consistent basis. Be what you want. And you've got to have the discipline to hold people accountable. Once again, I want to say thank you so much for continuing to spread the message or

telling a friend or two, hey, you should listen to this episode of The Learning Leader Show with General Stanley McChrystal. I think he'll help you become a more effective leader because you continue to do that, and you also go to Spotify and Apple Podcasts and you subscribe to the show and you're rated hopefully five stars and you write a thoughtful review by doing all of that. You give me the opportunity to do what I love on a daily basis, and for that I will forever be grateful. Thank you so, so much.

Talk to you soon. Can't wait.