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Retired 4-Star General Stanley McChrystal: From Military to Business Leadership

General Stanley McChrystal, CEO and Chairman of McChrystal Group
General Stanley McChrystal, CEO and Chairman of McChrystal Group



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Gen. Stanley McChrystal (00:00:00 to 00:00:36)

What I have found is it's communication. You have got to start with explaining to people. Here's what we're trying to do. This is the value proposition that I am offering you as a potential employee. This is what I'm asking from you as an employee. These are the realities of the market and how we operate in that market. Therefore, if we can find a better way and do it, we will do that. But if you explain all of that, if you tell somebody, shut up and color, because that's what the job is, that doesn't work.


Announcer (0:00:36 to 0:00:54)

Welcome to Paychex THRIVE, a Business Podcast where you'll hear timely insights to help you navigate marketplace dynamics and propel your business forward. Here's your host, Gene Marks.


Gene Marks (0:00:54 to 0:02:16)

Hey, everybody, it's Gene Marks. And welcome back to another episode of the Paychex THRIVE podcast. Thank you so much for joining me. My guest today is General Stanley McChrystal. For those of you who watch this on YouTube, I have to read this because there's so much of it, and I want to make sure this bio gets out to you.


Stanley is a retired four-star general. He is the former commander of U.S. and International Security Assistance Forces in Afghanistan and the former commander of the nation's premier military counterterrorism force, Joint Special Operations Command. In 2013, Stan published his memoir, "My Share of the Task, which was The New York Times bestseller. And as an author of "Team of Teams, New Rules of Engagement for a Complex World", which was also a New York Times bestseller in 2015.


Stan also co-authored "Leaders, Myth and Reality", a Wall Street Journal bestseller based on the epochal parallel lives by Plutarch. He previously served as a senior fellow at Yale University's Jackson Institute for Global affairs, where he also taught a course on leadership. He currently sits on the board of Navistar International Corporation, Siemens Government Technology, and JetBlue Airways. And Stanley, I'm an American Airlines flyer. I just want to let you know that, but I'm sure JetBlue is just fine. And anyway, I'm very, very proud to have you on the podcast. Thank you so much for joining me.


General Stanley McChrystal (00:02:16 to 00:02:17)

Gene, it's my honor. Thanks for having me.


Gene Marks (00:02:17 to 00:03:01)

Yeah, it's good to speak with you. You and I spoke about a year ago on my Biz Books platform after your book came out, and we talked in detail about the book. But this conversation, like I kind of mentioned to you before we started recording, is really about leadership. I mean, our audience are business owners, small- and mid-sized businesses, and managers. They're leading teams, they're leading organizations, and I think you have a lot of really great advice to share, and I know you write and speak on this topic a lot. So, let's talk about leadership. My first question to you is about your core philosophy on leadership. What is it, Stan? And how did it evolve over the years?


General Stanley McChrystal (00:03:02 to 00:04:15)

I think my core beliefs on leadership is that it emanates from the individual, and it starts with the ability to show self-discipline. Most of us know what good leadership looks like. We've been exposed to it. We've also seen bad leadership. We can read books with lists of traits of good or bad leaders.


We don't need to be told how to be a good leader. We need to learn how actually to get ourselves to do that. And to me, that comes down to self-discipline. You're in an instance where you should treat somebody a certain way and you don't, and you walk away going, wow, that's really not me. So, there's a question there. Or the things you know you ought to do to be better prepared to lead your team, to be better, more knowledgeable about something, to be better physically ready, whatever it is, to be more effective for your team.


Why is it you sometimes do it and maybe too often don't do it? And that's so it comes down first and foremost to leadership resides inside the individual. And if you don't have solid values, if you don't know who you are, you're always a bit adrift.


Gene Marks (00:04:15 to 00:04:16)



General Stanley McChrystal (00:04:16 to 00:05:06)

I step one step away from that idea that it is all inside the individual. It's also contextual. I could make an argument that Gene Marks could be the perfect leader for the perfect moment in Organization X, and you could be parachuted in and you could turn it around and save the day. And then we could pick you up and we could put you in another organization and you might get a very different outcome. And you did not change. The context of the moment; the followers, the situation that's involved a little bit about you personally, but really, we need to understand that the person who is appropriate and perfect for one moment may not be for another. And therefore, I don't think there's anything as a generic perfect leader.


Gene Marks (00:05:07 to 00:05:20)

It is hard to define leadership only because, like you said, it's not generic. It really kind of depends on the person. So, talk to me about yourself. I mean, what kind of a leader are you? Or were you?


General Stanley McChrystal (00:05:22 to 00:06:50)

Yeah, I have evolved a lot as a leader, but there are some core things that have stayed. When I was a young leader, probably like many young leaders, I very much wanted to establish myself. When I first came out of the United States Military Academy in 1976, the Army wasn't in very good shape. Then I went, took my first platoon, and it was kids from parts of the country and parts of society that didn't have the advantage as I did. And I wanted to be in charge.


I wanted to tell them what to do, because that was my job, and I wanted to be looked at as the officer, the lieutenant, the leader. What I learned over time was, in reality, in most of what we did, they knew more than I did. They'd been around longer, they had different perspectives. They were sometimes street-wise, or I'll call woods-wise. People had that background.


There were some talents and education I had, but I was really a piece of a puzzle. And if the puzzle was complete, we were a pretty good platoon. Any one of us, or without it, we were not. And so still, for about the first 10 years of my career, I was a very driving micromanager. And when you lead organizations small enough where you can sort of get your arms around it, you can get away with that. You can essentially move every chess piece and make it work.


(00:06:50 to 00:08:04)

And then about the time I was mid-30s, I was commanding a ranger rifle company, a more elite organization. And I got this revolution from the NCOs that the sergeants just, they pushed back. They said, we don't need you to tell us how to do our jobs. We need you to do your job, Captain. And at first my feelings were hurt, but then it was liberating, because if I could accept that they would do their jobs and I did my job, we could get a lot more done.


So, for the rest of my career, I've been evolving away from that micromanagement, and it keeps going. Now, I'm still - talk to anybody who works with me - I'm still very demanding. I am still a bit impatient. I'm still relentless in being willing to push. And I could make an argument to a mirror that I actually feel pretty good about those attributes, but that is me. If people complain about, that's fair. But I don't try to do people's jobs for them. In fact, I want to trust them and I want to support them doing that. And I think I feel much more comfortable as a leader in this way than I did earlier.


Gene Marks (00:08:05 to 00:08:25)

Do you think leadership has a lot to do with someone's age and experience, or not at all? We have people listening to this that are, they might be running a startup or a small business, that they might be 30 years old, and then we have others that are in their 50s or 60s. Do you think different qualities are needed based on your age or your generation?


General Stanley McChrystal (00:08:28 to 00:09:08)

I'm not sure that's correct. I think that I've known people who are, when they are young, they are jerks, and when they are old, they're jerks. I've known other people who, when they're young, they were good. When they're old, they got angry. So, no, I think it's much more a case of what's needed in that particular organization and instance and that person's life journey. We are all not automatically something at a certain age. We are the product of all the things that we've touched and done, the people we've been around. And so I think it's not strictly age. I think it's your diverse perspectives.


Gene Marks (00:09:08 to 00:09:19)

Good. You had mentioned about I've known people that were jerks when they were 30 years old and they were younger jerks when they were older. Can you be a jerk and still be a good leader?


General Stanley McChrystal (00:09:20 to 00:10:05)

Boy, my wife and I have been having a lot of conversations about. Sure. And here's where I come down. Yes, you can. And that sounds strange, but now when we talk good and bad, I'm not saying good and evil. I'm talking about effective or not, because if you look at Steve Jobs or if you look more recently at Elon Musk, I can argue that we wouldn't have the SpaceX program doing what it does. We would not have PayPal doing what it does. We certainly wouldn't have electric cars where they are without Elon Musk's personality, that driving sense. Now, I don't know him personally. I've met him once.


(00:10:05 to 00:10:50)

But the reality is I don't think he's someone that I would be real comfortable hanging out with. But the question is, does he get things done? And the answer is, he certainly gets a lot of things done and maybe creates a fair amount of negative things in its wake. I think our society needs a certain percentage of those people. I think if everybody was sort of homogenized with the rough edges sanded off of us and wanting to get along and being very comfortable with everyone, I don't think we'd get as much done. I think some of these big personalities have got to crash through our society to force the rest of us to move forward.


Gene Marks (00:10:50 to 00:12:01)

Yeah, I literally just finished this past week watching the “Last Dance”, the documentary about Michael Jordan on Netflix, which everybody in the world watched it during COVID, and of course, I just got to it. And it was an amazing documentary about the guy, and he admits during his years with the Bulls, he was a jerk. He was tough to get along with for the very reason why you just laid out. He was set on this mission of being the very best and winning championships, and he had little patience for people that didn't align themselves with that leadership goal. So, tell me a little bit about your thoughts on creating a team around a good leader, because that's what the Bulls did in the end.


I mean, they brought Jordan in as a young guy. They saw his talents and they saw his personality, and they formed a team around him. Scottie Pippen and Dennis Rodman and others that, Steve Kerr, that they could jive with him as a good way. So, as a leader, talk to me a little bit about creating a team for yourself. What do you look for? How do you do it?


General Stanley McChrystal (00:12:02 to 00:13:45)

Yeah, if you are talking about creating it for yourself or around yourself, I think the first thing you want to avoid is hiring a Greek chorus of people who agree with you, and that's comfortable and that's what the most common practice is. But you got to avoid that. You've got to get people who do things you don't do. They either have skills you don't do or they interact with people the way you don't do or uncomfortable doing, or they talk to you in ways that you need to be talked to. And so if you're talking about a small personal staff, there needs to be somebody who can get in your face and tell you, you just acted like a jerk in the last thing, and you got to stop that.


You've got to have other people who can tell you hard truths. Now, not everybody needs to be there with a short sword poking you, because you also need people who know when you've been bruised up and you're working hard and you need somebody who can say, okay, we're going to be okay. Sometimes you need somebody to say, hey, you did great. Even though you know you didn't do great, you need to hear it. So, it's that combination of people who have both the empathy to understand you and that moment, the courage to give what's required in that moment, and the loyalty.


Because at the end of the day, they've got to be loyal to the overall mission. Part of that's to you, it's manifest to you, but part of it is to the overall mission. They've got to believe that this is what we are here to do.


Gene Marks (00:13:45 to 00:14:45)

You know, your point, it's funny. And you mentioned, I just, I read George Isaacson's book on him, Walter Isaacson, excuse me, his book on him recently. And one of the things that struck me is exactly what you just said about Musk. There was one story he told of a scientist that worked for Musk at SpaceX and just couldn't take any more, the hours and the demands and whatever, and he quit.


And the scientist said later on that within a few months after quitting, he didn't have the same. Like, he wanted to work for somebody, that he could be part of that they're doing something. It's more than just him. And Musk was that guy. And he wound up going back to working at SpaceX knowing that, okay, this guy's a demanding guy, but I believe in the overall mission. And don't you think that's one of the most important things a leader has to show is they have to communicate to their team that it's not about us, but it's about what we're trying to get done here.


General Stanley McChrystal (00:14:46 to 00:15:21)

Yeah. I think if the leader can create a narrative that is convincing of what we are trying to do is worthy, and we are trying to do it in the best way we know how, then they will put up with a lot of things from the individual leader, because that leader has made a good case. It's harder in some businesses. I mean, if you manufacture bagels, it's hard to say we're going to change the world by making really great bagels. But if you've got national service or going to space or even creating electric cars, there is an easier path to that kind of a narrative.




Gene Marks (00:15:21 to 00:15:46)

Sure. I'm going to even argue with you on that, only because even the bagel maker is making bagels that's giving pleasure and enjoyment to their customers. Somebody's having a lousy day, and they came in, they're getting a chocolate chip bagel, and it just makes them feel better. And you're right. This is not like fighting a war or doing something like building spaceships that go to Mars. But I guess everybody does a little something to contribute. And I just think the trick is communicating to your team, like, hey, what we're doing is special, and it is, in our little part of the world, contributing a little bit to that part of the world.


General Stanley McChrystal (00:15:49 to 00:16:09)

To push back on you. I don't disagree with that. But I think sometimes in those cases, the argument is about the team. The argument is, we've created team; you got jobs, you got health care, you got a sense of family. This is what life is.


Gene Marks (00:16:09 to 00:16:53)

Yeah. And sometimes a lot of people don't realize that nowadays that this is what it's all about. How about actually putting your money where your mouth is and doing stuff? Getting back to Jordan, I'm obsessing about this because I just saw the documentary, and whatever he demanded of his teammates, Stan, I mean, Jordan did it himself 10 times over. He was the first guy there to practice, the last guy to leave, the hardest-working guy. There was nothing he did answers that he wasn't willing to do for himself. Give me some of your thoughts on actually doing it. For example, you didn't just go into the military as a captain. I mean, you must have had to spend a number of years in the trenches. Can you even be a leader without having that kind of experience?


General Stanley McChrystal (00:16:54 to 00:18:29)

Well, I certainly wouldn't claim you cannot, but I say it's extraordinarily helpful if I think in the military it's helpful because you get experience at every level. So, you know what's happening at the various lowest level. When it's raining outside and you're more senior, You know what it feels like to stand in the mud and the rain. You know the implications if you draw on a map and say, this battalion will move from this place to this place, you know how far it is and you know how long it takes to walk there and how painful it is. So, it's not a clinical planning thing. It's a very human thing.


And then the other part is doing it with them, not just that you did it when you were younger, but when you become more senior, you've got a lot of things to do, a certain percentage of your time has got to be go out visiting soldiers, sharing some of the danger, sharing some of the hardship. Now, you're not there every day like they are, and they know that and they don't want you to be, but they want you to come out there and share it with them through part of the time.


And I found that I got tremendous credibility from soldiers for making the effort. And I know every military leader that I've been involved with, particularly when it gets really bad, go to that place where you've just had the most casualties, where the worst things are happening. You, the leader, go there, plant yourself there, and it sends a powerful message, one about the importance of it and your willingness to do that.


Gene Marks (00:18:30 to 00:18:59)

You don't just become a general by mistake. It takes a long time to navigate the organization. And I know, I am sure that you have come across your fair share of incompetence. People that are lazy, people that were in positions that were your superiors that you just knew you couldn't believe that they were your superiors for all different reasons, because life is not fair. How did you deal with that?


General Stanley McChrystal (00:19:02 to 00:20:48)

I love your quote. You don't become a general by mistake, and the answer is, I've always thought a few people do. Here's the way I think of it. The military really does a very good job of preparing people, selecting talent, whatnot, but not a perfect job.


And because wars are episodic, meaning you have long periods of peace and then you have wars, you have a tendency to have people rise through most of their career in peacetime, and they are raised on evaluations of how they are in peacetime, how they look and act in that environment. And what we found, what I personally found in Iraq and Afghanistan is of the body of senior leaders, largely my peers, slightly on either side, a good percentage of them were not fit for that duty. They were not competent either emotionally or in some cases just professionally, to be a general officer in combat. Now, it wasn't entirely their fault because our system had rewarded a number of things in peacetime.


You do resent it, because when you get there and it's very hard and you've got people who are not up to the task, it's pretty obvious, pretty quick. And our system is not nearly as good as the commercial world. In commercial world, you fire CEOs. The military is much more reticent. And so there's a temptation or a habit, I'll call it, of leaving people in positions of life-and-death responsibility long after they should be. And so that's a part of the U.S. military that's got to be, want to say, updated. It's got to recognize the need to do that.


Gene Marks (00:20:49 to 00:21:04)

As a leader, now, in an organization, tell me how it's different running a business today versus when you were in the military and running a team there.


General Stanley McChrystal (00:21:05 to 00:22:40)

The military was easier because there was structure. You wear your rank on your uniform, people know what you've done to get there. And in the civilian world, there's rank differences and whatnot, age differences, it's much more, at least on the surface, egalitarian. At the same time, the challenge in a civilian business, in my view, is to set clear standards and expectations. Civilian businesses only work if they make money. And so the first thing is you've got to create a model that, if you do it correctly, makes money, because otherwise it's a hobby. You create that and you set expectations.


A lot of your employees that come in may not have much experience either in business or in life at that point. and they're trying to figure out, now wait a minute, are these expectations fair? Are they this? Are they that. The great driver is capitalism, the profit and loss requirement. You can argue about work life balance, you can argue about any of the number of things which we make hot button items now, which are great unless you don't make money, right. And in which you don't make money.


It's all academic. And so, what we've got to do is make sure we cross over and say there are things that we would like to do that we can't afford to do because they won't work. There are other things that we just should do, and we've got to try to work our business processes and models so that they will allow it.


Gene Marks (00:22:40)



General Stanley McChrystal (00:22:40 to 00:22:43)

We can take care of our people and that sort of thing.


Gene Marks (00:22:44 to 00:23:35)

I can't even imagine some of the circumstances for yourself coming out of the military for all these years, now running a business, and dealing with today's workforce. It's younger, there's a lot of demands for flexibility, and working from home and different things, but it's the nature of the workforce. And my smartest clients, remember, most business owners, more than half are over the age of 50. So, there are plenty of older people that are running businesses, but my smartest clients have, they might grumble a bit about it to their spouses, but they adapt in the office. I'm kind of curious how you adapted to that, coming from a military background and now being in the private sector with a completely different type of person that you’re managing.


General Stanley McChrystal (00:23:36 to 00:24:39)

It takes adjustment. I think the first thing is we're all people and we say that we have our biases and it goes in every direction. Young people look at an old person and they're immediately biased and thinking, what does the boomer thing? Yeah, the old person looks at young people and we automatically think that they think certain things. And of course, in no case is our perception accurate, and it certainly isn't accurate in the aggregate.


It might be accurate in the individual. What I have found is it's communication. You have got to start with explaining to people; here's what we're trying to do. This is the value proposition that I am offering you as a potential employee. This is what I'm asking from you as an employee. These are the realities of the market in how we operate in that market. Therefore, if we can find a better way and do it, we will do that. But if you explain all of that, if you tell somebody, shut up and color, because that's what the job is, that doesn't work. It really didn't work with soldiers either.


(00:24:39 to 00:25:09)

There was a perception it did, but I actually found that soldiers really only want to attack the hill if you told them why that hill was important. And so it's an exercise in that in the civilian world, in today's environment, it's just more informal. And so young people are perfectly happy to ask, "Hey, Stan, why aren't we doing X?" And it takes a second, you've been working real hard, and you go, okay.


Gene Marks (00:25:10 to 00:25:12)

Did he just ask you that question?


General Stanley McChrystal (00:25:14 to 00:25:21)

How should I answer that question? And I'm sure everybody goes through it and I'm sure they feel the same about my answer.


Gene Marks (00:25:22 to 00:25:53)

So, a lot of people love to ask about lessons learned and what the failures they've had in their careers that taught them or whatnot. But I'd like to see if you can dig back a little bit, pat yourself on the back a little bit; Give me an example sometime in your life, in your leadership life, where you nailed it, you did something right, where you look back and you're like, in that one instance, that one thing that I did, I handled everything right,  and this is why I'm proud of what I did as a leader. Can you share for an example?


General Stanley McChrystal (00:25:53 to 00:25:56)

I hope not a lot of those Gene. So, you made this hard.


Gene Marks (00:25:56 to 00:25:58)

You won't be sitting here otherwise.


General Stanley McChrystal (00:25:58 to 00:26:53)

Yeah. When I was a battalion commander in second Ranger battalion, I wanted to have the battalion become proficient in unarmed combat because that gave me an option not to kill an enemy soldier, but instead to deal with them otherwise. And it just, it's a good thing for them to be good, and none of them were. So, the Army's program wasn't any good.


I brought, hired in this wrestling coach, I hired a karate guy, I hired a bunch and they come in and they teach a small group of people. And the idea was train the trainer, that small group is going to train the battalion could never get it to take. Then decided to bring in the Gracie brothers who do Brazilian Ju Jitsu. And that was important. But the most important thing is we got all the platoon sergeants in the battalion. These are the senior sergeants in every platoon of 42 people.


(00:26:53 to 00:27:50)

So, they are really the culture carriers for the battalion. And so they're about 12 of them, and we got them, and we put them in a two week course and we had them get truly proficient with the Gracie brothers. And what it did was as soon as these sergeants, influencers, you could call them, as soon as they came out of that course, they were proud of what they could do. They were going to show the Rangers what they were going to do, and they were confident in teaching the Rangers.


Once we recognized who the influencers were and got to them, I mean, it went through the battalion almost immediately. It was amazing. So, you learn who really gets people to do things or believe things, and that's a form of leadership. It's figuring out what changes the direction of an organization, and you got to find the right people.


Gene Marks (00:27:51 to 00:28:51)

I only have a couple more minutes with you, but I did have to ask you, I recently went to an Italian restaurant with my family, and it's a chain restaurant. And I went in there, Stan, and from the person that greeted us at the door all the way through to our serving staff, all the way through to the bus boys coming around and picking up our plates, everybody was like, great. They were cheerful. They were courteous. This is 2023; there's a lot of hourly workers out there that aren't so happy with those. These people seem really good with their jobs. It was kind of an eye-opening thing to me, and my feeling was, I mean, this has to come from the top, right?


Why do you think that is? Why are some organizations run in such a way where people are proud to be working for them, why they're happy in their jobs, and why that comes through to their customers? Why do you think that is?


General Stanley McChrystal (00:28:52 to 00:29:04)

I think it starts with the organization knowing how important that is. From the top, they know that that experience which you just described is the most important thing. You probably can't remember what you ate, and it doesn't matter.


Gene Marks (00:29:04 to 00:29:06)

Veal parm, by the way, but you're right.


General Stanley McChrystal (00:29:06 to 00:29:50)

I get the point how you felt. And so the reality is they understood that was important, and they probably have in place a number of different things that reinforce that first, clear standards, what people want from how they want employees to act, peer pressure from other employees, because, hey, this is not the way we do it. I would imagine that the leadership reflects the same behaviors. Then there's likely reinforcement systems that says, if you do that really well, that's reinforced. If you don't do that, that's noted. And it's just really understanding what the critical aspect of demeanor in service really is.


Gene Marks (00:29:52 to 00:30:05)

I've been speaking with Stanley McChrystal is a retired four-star general, now a speaker, an author of a few books, a board member. Gen. McCrystal, how do we get in touch with you? How do we find out more about what you do?


General Stanley McChrystal (00:30:06 to 00:30:14)

Well, I am at and we're a 101-person consulting company in Alexandria, Va.


Gene Marks (00:30:14 to 00:30:17)

You consult on leadership, I guess, right? And management.


General Stanley McChrystal (00:30:17 to 00:30:22)

Well, leadership, but more broadly, we do management overall. We make organizations function great.


Gene Marks (00:30:23 to 00:30:31)

Well, Stan, thank you so much for your time. It's a great conversation. I always learn a lot when I speak with you, so thanks. I want to wish you best of luck going forward.


General Stanley McChrystal (00:30:32 to 00:30:33)

Thank you Gene.


Gene Marks (00:30:33 to 00:30:50)

Everybody, you have been listening and watching to the Paychex THRIVE podcast. My name is Gene Marks. Thanks so much for joining us. If you have any questions or you'd like to suggest a future guest, please visit us Again, thanks for joining. We'll see you again next week. Take care.


Gene Marks (00:30:50 to 00:31:25)

Do you have a topic or a guest that you would like to hear on thrive? Please let us know. Visit and send us your ideas or matters of interest. Also, if your business is looking to simplify your HR, payroll, benefits, or insurance services, see how Paychex can help. Visit the resource hub at That's WORX. Paychex can help manage those complexities while you focus on all the ways you want your business to thrive. I'm your host, Gene Marks, and thanks for joining us. Till next time, take care.


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