Stanley McChrystal

Retired U.S. Army General; Founder and CEO, McChrystal Group

I think that the biggest thing about leadership is self discipline. Most of us know how to be a good leader. The question is, will we do it?

Summary

This week on “Leadership Matters,” Alan is joined by an extraordinary leader and public servant — Stanley McChrystal, the former commander of the US and allied forces in Afghanistan. Since retiring from the military, Stan has served as CEO of McChrystal Group, a consulting firm that provides leadership and communications insights to high level executives across a variety of industries.

In his conversation with Alan, Stan discusses his early life and education, the leadership lessons he has learned over the course of his career, and his most recent book, titled Risk: A User's Guide. At a time when leaders across sectors face risks of accelerating speed and intensity, Stan provides a thoughtful road map of the skills and abilities organizations should nurture in order to be prepared to tackle whatever sort of crises may come their way.

Mentions & Resources in this Episode

• McChrystal Group

• The Doomsday Clock

• Risk: A User’s Guide

Guest Bio

A retired four-star general, Stan is the former commander of US and International Security Assistance Forces (ISAF) Afghanistan and the former commander of the nation’s premier military counter-terrorism force, Joint Special Operations Command (JSOC). He is best known for developing and implementing a comprehensive counterinsurgency strategy in Afghanistan, and for creating a cohesive counter-terrorism organization that revolutionized the interagency operating culture.

Throughout his military career, Stan commanded a number of elite organizations, including the 75th Ranger Regiment. After 9/11 until his retirement in 2010, he spent more than 6 years deployed to combat in a variety of leadership positions. In June 2009, the President of the United States and the Secretary General of NATO appointed him to be the Commander of US Forces Afghanistan and NATO ISAF. His command included more than 150,000 troops from 45 allied countries. On August 1, 2010 he retired from the US Army.

Stan is a senior fellow at Yale University’s Jackson Institute for Global Affairs, where he teaches a course on Leadership. He also sits on the boards of Navistar International Corporation, Siemens Government Technology, and JetBlue Airways. He is a sought-after speaker, giving speeches on leadership to organizations around the country. In 2013, Stan published his memoir, My Share of the Task, which was a New York Times bestseller; and is an author of Team of Teams: New Rules of Engagement for a Complex World, which was 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.

A passionate advocate for national service and veterans’ issues, Stan is the Chair of the Board of Service Year Alliance. In this capacity, he advocates for a future in which a year of full-time service—a service year—is a common expectation and opportunity for all young Americans.

Stan is a graduate of the United States Military Academy at West Point and the Naval War College. He also completed year-long fellowships at Harvard’s John F. Kennedy School of Government and the Council on Foreign Relations.

Clips from This Episode

• Stan reflects on his time in Afghanistan and the challenges of his responsibilities

• On what we got right and wrong in Afghanistan

• On how Stan’s parents overcame their conflicting views on Vietnam

Episode Transcription

Alan Fleischmann

You're listening to SiriusXM’s “Leadership Matters.” I'm your host, Alan Fleischman. My guest today is an extraordinary leader who has played a key role in leading the United States military through some of its most difficult challenges in the last many decades. General Stanley McChrystal is the former commander of the US and allied forces in Afghanistan, and the former commander of the Joint Special Operations Command, the nation's premier military counterterrorism force. He is known for developing and implementing a comprehensive counterinsurgency strategy in Afghanistan building upon his work at JSOC that revolutionized the command’s operating culture. During his military career — in fact, throughout his military career — General McChrystal commanded a number of elite organizations and spent more than six years deployed to combat in a variety of leadership positions. 

After retiring from the military, General McChrystal founded McChrystal Group, a consulting firm that provides leadership and communications insights to high level executives across a variety of industries. He has also written a prolific number of books. He is an author of many outstanding books, one of which I just read, called Risk: A User's Guide, which provides leaders across sectors and disciplines with strategies for tackling risk in its numerous forms. General McChrystal is a senior fellow at Yale University's Jackson Institute for Global Affairs and sits on the boards of a variety of companies, including Navistar, Siemens, and JetBlue Airways. 

I'm thrilled to have the general join us today to discuss his amazing life and career and the insights he has had over the years that he can share with us. General McChrystal, welcome to “Leadership Matters.” It really is a pleasure having you on today.

Stan McChrystal

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

Alan Fleischmann

You're wonderful. And you come up in conversation so often. I work with CEOs, as you know, and you come up all the time. And people quote you — I quote you — people draw from your amazing insights. And it is quite extraordinary how you do transcend across public life, private sector and civil society as well. 

Let's get a little bit focused on where you come from. You were born in Fort Leavenworth, Kansas, into a military family. Your father was a major general. What was life like around the house growing up? Brothers and sisters, your mom and dad; tell us a little bit about them.

Stan McChrystal

Yeah, absolutely. And this timing is really fortuitous: I spent yesterday afternoon going through some of my father's belongings. He died a few years ago, and my stepmother — my mother had died when I was young — my stepmother had kept these items, papers, photographs, military awards, and things like that. And she wanted me to go through them and make sure that my siblings and I took what we wanted and kept them. And it was very interesting, because first, my father was a soldier. And his father was a soldier. And then his son, obviously, was a soldier. Actually, my dad had five sons, and we all went into the Army. And my sister married a soldier. So we were an Army family from the time my grandfather entered during the First World War, until… Well, there are still nephews and nieces serving today. In fact, the day my grandfather and my father died, he had four grandsons in Afghanistan, serving at the moment he died, and we delayed his burial until we all could come home.

But to give you a sense, it didn't feel like we were a military family as much as you would think. If you've ever seen the movie The Great Santini, where you've got this very sort of boisterous Marine Corps fighter pilot and the way he lives colors the family. We weren't that way. My father was a very reserved, quiet guy. And so we spent much of our lives not living on Army bases. But he would go to Vietnam and leave the family in Arlington, Virginia, and then he would come home. So we were very aware and proud that he was in the Army, but it didn't permeate everything about our lives. 

So yesterday as I went through his belongings, I was able to look at my grandfather's grades from Santa Clara University in California — I hope my grades never go to my grand or great-grandkids. And  then my father entered West Point in 1942. And in this sheaf of papers is the graduation announcement for June Week in 1945, when my father graduated, and then photographs of he and my mother, who he had met soon after graduation, and then through his career there are four silver stars that he had won for gallantry. One in Korea and three in Vietnam. And that's sort of a stunning number to somebody like me. And so suddenly my father takes on a different perspective than just the one that I knew him as, this good, kind of a quiet guy. 

So it was a close household. My father and mother had an incredibly close marriage until my mother died suddenly at age 45. But it was six kids, it was two parents that I never saw in a fight. And I tell people this also: I never in my life saw my parents do anything wrong. And when I say that, I'm talking about how I never saw him take a parking space he shouldn't have. I never saw him, with a wink and a nod, keep extra change from an exchange at a store. I just never saw them cut any corners in their personal behavior. They didn't lecture us, they didn't sit us down and talk about values and behaviors much. They just were a certain way. My mother read voraciously. And she was always doing different things. And my father worked very hard. But they both just conducted themselves in a way that I think was intended to give us a beacon. And I think it did that.

Alan Fleischmann

I'm curious now, because that's such an amazing statement to say about your mother and father, a beautiful one. No better legacy in the world than that. And that just makes you almost sit up straight thinking about ourselves a little bit, like those little things you do, there are their eyes watching and ears listening. And what better example. What was their family background, did you know your grandparents?

Stan McChrystal

Yeah, I knew my grandparents but not closely — well, my grandmothers. My father's side were a military family. And my grandfather died about the year I was born. So I never knew him. But we knew my grandmother, but she lived on the other side of the country. So I saw her once a year. And she was a wonderful elderly lady who would visit but was not a force in our lives. 

On my mother's side, she was from the Deep South. She was from Chattanooga, Tennessee. Her parents had split up when she was very young, so she had kind of a difficult journey. And I knew my grandmother. And she was, again, a wonderful person. But she came once a year. And so there wasn't a big exchange. But there was a sense of these two very different worlds, this military family, and then on my mother's side, this sort of pretty well established, pretty prominent family in Chattanooga, Tennessee, the Bright family that my mother came from. They were different worlds.

I remember we, in 1965 on my father's way to Vietnam, he had to go to Fort Benning, Georgia, to take a course before he headed over to a combat tour. And we, all six kids and two parents, loaded in this station wagon. It was the trip from Hell, as you can imagine — it was a car with no air conditioning. And as we took it, my mom got appendicitis halfway between DC and Chattanooga. So we rolled into town to see the family, my mom had to go straight to the hospital. 

We were suddenly amongst my mother's extended family and they were very different from us. They were wonderful people, but they were a more affluent, more established Southern people — I hate to use the term, but sort of aristocracy. And we weren't. In fact, they tried to persuade my father to leave the service so that he could get a real job. Of course, he didn't do it. But it really gave me a window into the differing backgrounds. But I was always kind of surprised that my mother came from that because she wasn't that way. She was a very liberal civil rights activist, this sort of thing. And she was against the Vietnam War while her husband was over there fighting it. So it was a pretty interesting difference, but it was a good grounding. I think it was a good balance.

Alan Fleischmann

How did your mom and dad deal with that? With her being against the Vietnam War, and your father playing such a significant role in the military? How did that work out? That must have been fascinating conversation, or was it not spoken about?

Stan McChrystal

Yeah, my mom didn't speak much about it. She certainly didn't talk to the kids and criticize it. And I think her opposition was not vociferous — she wasn't the kind of person out there marching with signs. But at the same time, I think she had serious doubts, but she loved her husband. And she supported her soldier husband. And those were tough times, because she's got six kids. And we're living in Arlington, Virginia. And suddenly, my dad just goes to Vietnam. And in those days, the military didn't do much for you when the husband went away. You just motored on on your own. And my dad, of course, went twice, as did a lot of parents. But watching her keep the family together was pretty impressive.

Alan Fleischmann 

Wow. And you went on to West Point, right? Right away when you left for college, which is a big deal. Your father, you just said, was also a West Point grad. Did you always know you wanted to do this? Was it in the water? It was in the family, “I'm going to go into the military?” Or is there a choice at one point where you said, “I want to do the same as my dad.”

Stan McChrystal

Yeah, when I'm honest, I really decided at my earliest memory that I wanted to be like my dad. My dad was a soldier who went to West Point. So I wanted to be a soldier, I wanted to go to West Point. West Point for me, though, was just a way to get there. It wasn't a destination. It was a waypoint. But I wanted to be a soldier like my dad. And so I really never considered anything else. In fact, I didn't apply to any colleges other than West Point. And that's a little questionable, because I wasn't so impressive that they gave me early admission. I didn't get accepted until late May. And you have to show up the first week of July. So I think what they were doing is they filled the class and at the last minute, they go, “Okay, we got three more slots,”  and they probably understand McChrystal.

But it just seemed natural. And it's funny: a few years ago, I did a talk at a junior high school, where I've got a relative who was in the school, and a young girl said, “What other professions did you consider?” And I said, “Well, actually, I never considered any others.” And she said, “That didn't seem very smart. Does it?” I said, “Alright, kid, shut up.” No, I mean it's a fair point. I'm lucky that the Army turned out to be something I loved.

Alan Fleischmann

You're listening to “Leadership Matters” on SiriusXM and on leadershipmattersshow.com. I'm your host, Alan Fleischmann. And we're here with General Stanley McChrystal, former commander of US forces in Afghanistan, and so much more, and we’re discussing leadership and risk. 

So you go into West Point. Clearly, that had to be a major experience for you, a challenging place for anybody. And tell us a little bit about your time there and what you learned being a student at West Point.

Stan McChrystal

Yeah, my time at West Point is a subject of much laughter, often. I mentioned that I went to West Point because my dad did and I wanted to be a soldier. And so I went to West Point with the idea that I would just sort of show up, do the four years, and move on. I didn't take the place very seriously. I got there at age 17, it was the summer of 1972. And that was the 175th year of West Point's history. So West Point took itself very seriously. 17-year-old Stan McChrystal doesn't, and we had this sort of conflict. And so I'd had a pretty good education, but I had terrible study habits. 

So I got to West Point and I struggled academically for the first two years. I mean, the first year and a half, I struggled terribly. I was right at the bottom of the class, right on the edge of getting pitched out. In fact, in chemistry at the end of the first semester of my sophomore year, they wouldn't give me the workbook for the second semester, because the instructor said, “You're not going to be here after the term exam, you're going to be out. So I'm not going to give you the workbook.” I said, “Whoa, that's upsetting,” and I made it by the skin of my teeth. But I also got in trouble for behavior because I had a very good time in high school. Probably too good a time in high school. So I tried to transition out to West Point, and it's not designed to have a good time. And so I got in trouble — in complete honesty, I got in trouble for drunk and disorderly, I got in trouble for disapprobation to a cadet superior. Most people don't know what disapprobation is, it’s disrespect. So I got two big punishments for that. And then I got another big punishment for drunk and disorderly. And this is all in my first 18 months at the academy. 

So by 18 months, partway through my sophomore year, I'm what they call a century man. I've already got 100 hours of punishment tours, walked on the area back and forth. Sometimes you've seen it in movies. Typically in a class there will be, I don't know, 10 or 15 members of a class of 1000 who get to become century men, and I made it by partway to the end of our sophomore year. I was sort of the board leader. So for the first two years, my time at West Point was not happy. Not very successful. And certainly problematic, I'd say. But I knew I wanted to be a soldier. So to me, as long as I don't get thrown out, that's kind of okay. 

And then, at the beginning of my junior year, I came back, and we had a new tactical officer for my company. He has a meeting with every cadet: you have a meeting, you go up to his office. He was a major that had come out of special forces. He sat me down, he said, “Stan, you're going to be a great army officer. And these next two years, you’re going to be a good cadet.” And I started trying to peer over his desk to see if he had the wrong file. And I said, “You're talking to me? You know, I'm about to get thrown out.” And he goes, “No. The things you're good at are things you're going to be good in the Army, and the things you're not good at, at West Point.” And he kind of laughed and said they don't matter much. 

It was amazing, because his display of confidence in me, his sort of faith, that made a big difference in my thinking. Plus, I'd gotten in enough trouble that I almost couldn't stand that anymore. And then I started dating a little girl named Anne Corcoran. We've been married 45 years now. And she sort of changed me too, because having someone I cared about was another reason to get my act together and not be on punishment all the time, that sort of thing. So my last two years were sort of amazing. I ended up on the dean's list, I ended up on what they call that superintendent’s list. Everything went well my last two years, as opposed to my first two years. So that was one of the great turnarounds, I think.

Alan Fleischmann  

But it shows you the power of mentorship, of someone taking a double-look at you. All of a sudden, you found out there's a lot of value once you felt that someone was paying attention and respecting your journey. You kind of followed up and individually, you did right by them.

Stan McChrystal

That's so true. You feel committed to them.

Alan Fleischmann 

That's amazing. When you graduated, early in your career… You've had a pretty impressive career the whole time, but it started impressive day one. You’ve done everything from commanding a Green Beret unit to serving as the military fellow at the Council of Foreign Relations. Those early years, did they start to shape your leadership philosophy? Was there already a kind of playbook for the McChrystal way, with the little things you observed?

Stan McChrystal

I think with most leaders it's an evolution, and mine was exactly that. I started in the 82nd Airborne Division as my first job, as a platoon leader. It was a good place. But it wasn't a great place, because this is the 1970s Army, and the Army was not in very good shape and the 82nd was neither. But leading soldiers with problems, with tight budgets, and not great leadership all up your chain of command — that's a lesson in itself. You learn an awful lot in that kind of environment. And then, post-Vietnam, the Army started getting better, literally every year. You could watch it every year, the Army got more professional, more effective. And it really turned around about 1981, 1982. 

By the time I'm a captain — which is when you command a company of 150 or so soldiers — suddenly I'm in an Army that is on this upswing of everything. We're getting better tactically, we're getting more healthy with recruiting and whatnot. So I learned sort of the basics in the first few years, then I become a journeyman and I truly became proficient in my craft as a captain. By the time I'm a senior captain, I’m commanding a ranger company in an elite unit. Suddenly, I realized I can do this job. There's nothing about soldiering I can't learn if I try. So I started to have more confidence and of course, that builds you up. Then, I also started to develop personal opinions or concepts of how leadership should be. In some cases, that was very different from what I was seeing in the Army. I'm not going to say that I was a complete departure or an iconoclast, but about the time I was a senior captain, junior major, I started wanting to do things a little bit differently than the very top-down structure that most organizations had been doing then. I wanted to experiment with some information flow and decision making processes that were different. I found those were reinforced in every step in my career after that.

Alan Fleischmann

I think they're just such powerful lessons and powerful days to learn there. In fact, you really had some amazing experiences. You went on to command the US and allied forces in Afghanistan, overseeing Operation Khanjar, and then the 2009 troop surge. That must have been a very complex time. I imagine, of all the positions you've had, that had to have been one of the most challenging ones. And I imagine you had to balance stakeholders, an amazing amount of them and amazingly different ones. How did you set those priorities? How did you actually make that work as successfully as you did?

Stan McChrystal

Yeah. Of course, the ultimate failure of American policy in Afghanistan… I certainly own part of that, like a lot of other people do. I say that up front with all realism, not just false humility. But when I took over in 2009, we were about eight, almost nine years into our modern involvement in Afghanistan. And during that period, actually, not much had been done. We had toppled the Taliban pretty early, and then we really tried to keep a minimal footprint over there, not do much. And so efforts to build the government, the Afghan army, police, and whatnot, hadn't really gone very far. We and our Western allies had done much less than we sort of advertised. 

The Taliban had watched that. They had started coming back early in 2003 and then in force in 2006. So by the time I took over in 2009, things were going south pretty quickly. The confidence of the Afghan people was low, the confidence of the coalition of 46 nations who were helping was low, the confidence of the Taliban was high. The skepticism of local nations like Pakistan was high. So the entire effort in Afghanistan was going the wrong way. As we can all remember, it wasn't popular in the United States. We had gone through that first period in the beginning. Then after the Iraq War, nobody wanted Afghanistan to get bad again. But the reality was, it was getting bad.

So when I took over in 2009, the big challenge was to try to reverse the momentum. To change the confidence of the Afghan people, stop the momentum on the ground of the Taliban, rebuild the coalition's commitment to this effort. Because most of those nations had come to do peacekeeping, they didn’t come to fight a war. Then, they're suddenly in a war. So we had to change everybody's mindset, so we could do the important part. And then the US population didn't want another war. And President Obama's new administration didn't want another war. And they didn't want a war that rhymed with Vietnam. And so there were all of these forces. 

My mission was to try to make it work. The political civilian masters would decide if we do it, that wasn't my choice. My reality was, they had decided we're going to do it and I have to try to make it work as best possible. But their skepticism… You know, there's a lot of buyer's remorse on the part of the US government at that point: they're in, and they'd like not to be in. And yet, we're there trying to convince everybody that we're committed and we'll make this work. So it was the hardest thing in my life, to try to get 46 nations, a terrified Afghan population, a skeptical US public, all in line for something — that's hard. It was a fair challenge. That's what leaders should be given is tough challenges. And so that's what we tried to wrestle with.

Alan Fleischmann  

I know one of the ultimate things that came later can’t be judged on your watch, but that had to be one of your greatest accomplishments when you were in the military, would you say?

Stan McChrystal

Well, I'm gonna give you a conflicted answer. I am so proud of the things we did did. We built Afghan confidence up, we started building the Afghan military up, we started doing a lot of things right. We certainly got the international coalition more focused and more effective. So, a tremendous number of things we did right. However, when I look very honestly, I step back and say it all also depended upon making progress with the legitimacy of the Afghan government. And we didn't make the kind of progress that I hoped we would. That was always the place I was most worried — the corruption, the lack of technocrats, and their ability. As long as the Afghan government couldn't achieve that credibility and legitimacy with the Afghan people, you're building on a weak foundation. 

So the military part, I'm pretty proud of, some of the economic part I'm proud of, pulling the team together I'm proud of. But the reality is, we couldn't make that progress with the government. I don't know whether all those other things ultimately could ever have mattered, but you had to make that progress. And while I was there, we just didn't make enough.

Alan Fleischmann  

Was there a moment when you said to yourself, “It's time for me to retire, to imagine moving on from the military?” That had been your whole journey. And you've been so successful, and so well respected? Was it hard to leave?

Stan McChrystal

Yeah, it's interesting. I went to Afghanistan in the summer of 2009. And I had 33 years in service at that point, and I planned to stay in Afghanistan for three years. I thought that the commanding general needed to stay that long. I believed that, in three years, with the right effort and a little bit of luck, we could turn this around. Then I intended to retire at the end of that. There was potential for other jobs, but none that excited me, they were all going to be of a different kind. So I had sort of put the finish line at the summer of 2012 for me. Three years in Afghanistan, I thought it would be the right thing. Of course, I retired in the summer of 2010, after the Rolling Stone article blew up on me.

 When I left the service — although I was very obviously unhappy with the circumstances about that — I left after 34 years. In some ways, it felt about right. I'd been at war for most of the last decade. I was about to be 56 years old. And it felt like, “Okay, I did that, now it's time to do something different.”

You know, you have a choice when you leave a career like that. One choice is to be a retired general. That is an informal vocation, you can just be that for the rest of your life. But I didn't want to be that, I wanted to be something different. I wanted to try something new. So retiring when I did was actually, in some ways, that the silver lining in the cloud, because I had the opportunity and the impetus to go out, rebuild my confidence, try new things, and sort of prove myself again.

Alan Fleischmann 

Was that then the idea that became the McChrystal Group, or did you start by first joining several boards over time? Was it that exposure to the private sector that said, “People are coming to me for advice. I could do this for them.” I mean, you have a very unique model at the McChrystal Group of what you actually do, you're very clear what you don't do. Explain that a little bit, how that all came to be.

Stan McChrystal

Yeah, Alan. You know, I had this incredible vision of great clarity. We did this detailed business plan, and then we implemented — actually, none of that's true. I stumbled out of the military and a Navy SEAL friend of mine who'd worked with me said, “You want to start a company?” I didn't have anything else planned, so I said “Yeah, why not? How hard can that be?” So we started a company with no money — we bootstrapped everything out of our pockets — with no idea what the company would do, with what our contribution to the world would be. We didn't know whether we were gonna make bagels or be consultants or whatever.

We just sat at my kitchen table and we just started this company. So a fair amount of hubris, I guess. And pretty soon, we started to say, “Well, what do we have to offer? What are we good at?” We looked back at what we had done. We said, “Well, we do military things well, but really what we learned most came in the special operations world, when we learned to make organizations work, work differently, to communicate better, to do things in a different way.” We thought that that was actually germane to every walk of life. That was the thesis of what the McChrystal Group did. We said, “we think this applies in a complex environment and everybody's in one.” So we started moving there and then, probably about the first six or eight months, it started to crystallize.

Our first client was ScottsMiracle-Gro, the lawn and garden company. I'd gone out and given a speech with them. I was with the president after the speech, and I told the story of what we’d done in special operations. He said, “Can you do that?” And I said, “What do you mean? Can we do it? I did it.” And he said, “Can you do it in a civilian company?” And I said, “Of course we can. Hire us and we'll do this.”

It's interesting, because we stayed with them for about three years and had a tremendous relationship and refined what we did. It really proved our hypothesis, that what organizations need is not specific to the military. We don't come in and tell people how to be soldiers, sailors, airmen, and marines. We tell them how organizations have to operate in complex systems. So that has been sort of the evolution of the company as we go. We get more professional, more focused, more expert in those things we do, and more aware of those things we just don't want to do.

Alan Fleischmann  

It's amazing, because often, firms don’t have that sort of clarity about what they don't want to do. It really does enhance what people's understanding is of what you do. Because you're in a bedrock of expertise. We're focusing on that and that's what you get when you work with us. That's a pretty powerful message. 

You've also authored a lot of incredible books. The most recent one, Risk: A User’s Guide, came out a year ago. It's brilliant. I mean, it's truly an extraordinary book. I'm curious, what led you to write it? What did you hope would come out of those who read it? I'm going to urge the people who are listening to buy it and read it. I'm just curious what you've gotten from it, because I'm sure you have this idea, you share the book, and then you have this double experience where people started telling you how their lives have changed because of it. I'm curious what you've been hearing, but tell us a little bit about the origin of the book.

Stan McChrystal

Yeah, this one was really a journey of curiosity, and here's why: there's a ton of books on risk. If you want to get smart on risk, you can go out and find 1,000 books that show all these detailed models and things like that. I was on the board of Deutsche Bank, USA, so we dealt with risk every single meeting and every day. I saw all these complicated models on this. In the military, we'd had matrices to figure out the risk for operations training. So I had been schooled in risk, I had been experienced in dealing with risk. I'd walked away from that and said, despite all this, most of the time, we get it wrong. Most of the time, I get it wrong. Most of the time, corporations get it wrong. You can have a chief risk officer — well, Enron had a chief risk officer. So you know, it was the dichotomy between all we know about risk and how terrible we are at dealing with risk. 

I wanted to step back and write a book that was designed for people who are only as smart as me, not the brilliant theorists and all. The person who has to actually deal with it. And that's why we put this ambitious title, Risk: A User’s Guide, because it's designed not to dumb down risk, but to make it an approachable idea. We started with no thesis. We just said, “We're gonna study risk and see why we're lousy at it.” 

About a month after we started the book, COVID arrived. And COVID became this incredible case study of how to screw it up. You've got a threat coming that creates a risk. How does society swing and miss repeatedly in dealing with it? Well, we expanded beyond that. Pretty early, we realized that the message we were getting in every one of the areas we were studying was that the greatest risk to us is actually us. It's not that the threats that come at us are 10 feet tall or unbeatable and that we just succumb to the superior foe. It's because we don't do very well. That's military case studies, that's business case studies, you name it. You go back to Blockbuster failing to buy Netflix; the last Blockbuster, I think, is now closed. Just countless cases where our failure comes in the mirror, it doesn't come from what's out there. And so you say, “All right, well, that's pretty horrifying if the greatest weakness is us.” What do we do? 

Well, actually, it's pretty reassuring. Because if you thought that the threats are unbeatable, you just lay back as there's nothing to do about it. When the greatest threat to us is us, we're the agents of ourselves. We can make ourselves better. So we created a construct where we looked at what we call 10 risk control factors. They are factors like communication, narrative structure, adaptability, timing, things that an organization typically has to do for everything they do. But it's a question of how well they do them. Are they competent in those? 

We do an analogy to the human immune system, that assesses responses and learns every threat that comes into your body. We ingest about 10,000 micro organisms every day that could make us sick or kill us. And yet, we don't think much about it, because it's usually fine until it isn't. And then when your immune system doesn't work, suddenly, little things that wouldn't otherwise kill you do. Nobody ever died from HIV/AIDS. They died because their immune system was weakened to the point where things they normally would fend off kill them. 

So we stepped back and said, “Well, if we take that construct and we apply it to organizations — to individuals as well, but really better to organizations — we say we've got a risk immune system. What we've really got to do is be more competent.” The popular word now is resilient, but I'll use competent today and say more competent in dealing with things. It's really pretty basic. If you think about a threat coming into an organization, it could be a financial threat, a health threat like a pandemic, a natural disaster, or it could be a war. And you say, “Well, the responses to each of those are completely different.” I would argue, no, they're not. Because really, about 85% of what an organization does is the same crisis to crisis or risk to risk. You’ve got to communicate effectively and clearly. You've got to have a narrative that aligns everybody on what you are and what you're trying to do. You've got to have effective leadership. You've got to be adaptable. You've got to be able to shift to the momentum. You've got to be able to make decisions when you need to. So all of those things are sort of the blocking and tackling of functions. But really if you get that 85% right, the last 15% are pretty easy. You can adapt and focus on those. But most organizations stumble on the 85%. And then they are vulnerable to everything else that arrives.

Alan Fleischmann

Did you find that the risks are greater now, more urgent? In some ways, so many of the issues that we're dealing with now feel like déjà vu of the 1970s — gas prices, inflation. Certainly, the climate change situation is different today than it was, and more urgent. But you've got conflicts again that, frankly, on the geopolitical side of things, seem all of a sudden. We're worrying about nuclear weapons. It's cultural issues that we face. We went through a lot of those same culture issues in the ’60s and ’70s, but it seems to be a lot more impactful now. Maybe because we communicated directly and certainly. 

But there are a lot of vulnerabilities around here. I'm just curious whether you feel that we're more at risk today than we were 30, 40 years ago. And then also, whether you think executives need to see certain things coming, whether it's cyber risk or other forms of risk. How would you rank the most risky or less risky things?

Stan McChrystal

Yeah, it feels more risky. But I'll stay up front: if we go back 1,000 years, you had to worry about the Visigoths coming in and sacking your city. That was a pretty big risk. Or the Black Death taking out a third of Europe's population. That is a pretty big risk, when we compare. It's different. When we go back to the Cold War, the chance of nuclear war was very real and it was on our doorstep, the ‘30 seconds to midnight’ idea. So it's impossible to say that those weren't existential risks. 

But I think it's different now, and here's why: things happen much faster than they used to. Risks and threats arrive more quickly and they are more complex than they used to be. They're difficult to understand at the speed at which they arrive. That makes it difficult to align everybody's understanding of that risk and then to coordinate a response to it. So I would argue that certain things, like a pandemic, can move faster than they ever could before, just because transportation does that. And so it could be more dangerous. 

Nuclear war has now been democratized. What I mean by that is, weapons of mass destruction are not the purview of just big nation states anymore. You actually have the potential for a group, or even an individual, to create a weapon of mass destruction, I include cyber in that. So where we used to be able to hold our primary foe at risk, the Soviet Union, to ‘you bomb us, we’ll bomb you,’ you hope for rational action on each side. You can't hold someone at risk who doesn't care or who is this vaporous entity. So it democratizes the threats, meaning more players can cause greater damage than ever before. 

So in some ways, I think we have the tools of our own destruction present in front of us in more ways now than we've had before. To go to your rank ordering of the things that worry me most, the first is disinformation. This is not a new idea. There's always been disinformation out there. There were the Know-Nothings in American society. And then, of course, in different societies back as far as time. But you can propagate disinformation now with a level of efficiency that is terrifying. Our social media, our ability to communicate at almost zero cost at incredible speed, is something we as a society are not mature enough yet to handle. We've got a tool that we're just not capable of dealing with. So disinformation scares me most, because it gets large parts of our population going in certain directions. And if you think about it, that could happen tomorrow, with disinformation definitely inserted, that would take massive amounts of us out, left, right, up, down. I think that's the most frightening part of it to me. And we could end up in the United States in a civil war, or we could end up in a world war simply because people leverage that. 

Then there are other things, like the fact that more technology is out there. Now, precision weapons, cyber weapons of mass destruction… those are available to every man. And so every man can be an extraordinarily dangerous actor on the world stage. And then, of course, the connectivity of society, which has been a huge boon to globalization economically and prosperity. It's also shown just how vulnerable that is when your supply chains are weak, where suddenly, you've created this incredible construct and you don't realize that one critical part of it is in a place that is extraordinarily vulnerable, either to a natural disaster or political upheaval. I think our societies are more tenuous in that way than even we understand. I would argue that if you took the electricity out of a major US city for 24 hours, it would go tribal. And if you kept it off for two weeks, it would be unrecognizable. So we suddenly realize just how dependent we are on certain things.

Alan Fleischmann 

From Dr. King to Blockbuster movie rentals, your book also highlights a number of examples of good and bad risk management. You mentioned in the Blockbuster example before; what would you say are the best examples of good risk management?

Stan McChrystal

I think the Cuban Missile Crisis is a pretty good case. President Kennedy, 18 months earlier, had a really bad experience with the Bay of Pigs. The bad experience was a bad idea, poorly executed. Well, what really hurt him was the decision making process that allowed a bad idea to be executed; that taught him some serious lessons. So when he went to the Cuban Missile Crisis… there's a certain amount of incorrect history that's been put out. It's been polished up, but he actually did a very good job of assembling a diverse group of people. Not diverse in terms of gender and race — because this was the early 1960s America, so it was largely white and male — but it was diverse in terms of perspectives and experiences. 

So he brought a diverse group together, he put them through a process that forced him to widen the aperture of what the US responses could be. Suddenly, he created the ability to get a better set of options. Then he provided pretty good leadership that patiently led through this. And so when we look at dealing with a challenge like that, if you get the process right, if you get those basic risk control factors right, then typically, the right answer has a chance to come out. Whereas if you get it wrong, you're cooked.

Alan Fleischmann  

Mentors and supporters are critical in the life of any successful leader. I know, it's a big part of who you are. You've been a great mentor to others in both the private sector and then even before that, in the military. Which mentors and supporters have been most significant in your journey?

Stan McChrystal

I want to make sure, first that all, our listeners understand that sometimes we confuse a mentor with a sugar daddy, or somebody who's going to just sponsor us through our career and get us promoted. They might be one in the same. But a mentor is someone who helps you think, who helps you learn. The best mentors I had in my career where people actually poked at me. I had a major, a guy named John Vines, who’s still a close friend of mine from when I first joined the Rangers. On the one hand, he was supportive of me. But on the other hand, he would hold a card at me when he thought I was outside the lanes, or not doing something right, or taking a bad step in my career, whatever. 

If you have that kind of relationship with someone that you respect, that you will listen to, you don't have to try to emulate everything about them. But I had that experience with people who forced me to be as good as they thought I could be. They weren't just constantly saying “You're great,” et cetera. They were saying “That was great. Do that again.” 

There was another guy named John Abbott. He became a four star and he was my brigade commander when I was a battalion commander. He was very good about that. Because what he would do is really focus on the things that I was doing well and he would reinforce those who had sometimes pointed out to me. And then otherwise, he would point out the things that I might have thought I was doing well and I wasn't. But it was always in a very realistic way. So I didn't think I could ever just assume that he would do what I asked him to do or support me. I knew it was contingent upon me showing a kind of commitment to be better.

Alan Fleischmann  

Democracy, both in the US and abroad, has really been challenged, is facing a whole variety of challenges. In your view, what role does the private sector have to play in supporting, strengthening, and leading, even, in what needs to be done?  How big of a role should the private sector have in trying to build that up further?

Stan McChrystal

This is something we need to talk a lot about in our society. Because if you go back to Germany in 1933, Adolf Hitler is elected chancellor. Then soon after, he acquires full power. He's not very popular with big business. He's not very popular with the military. They both look down on him as sort of a nutcase. But he starts to make it in their interests. In the military he increases budgets, he does things. By 1936, the military changes their oath of allegiance from an oath to the government to an oath to Adolf Hitler. Big business starts to believe in Adolf Hitler, because he's putting money into it. He's making it worth their while to support this regime, even though a lot of them had a sort of aversion to many things about him. 

When we think about the role of business in the US, we went through a period where we said the role of business leaders and businesses is to look after their shareholders’ or their investors’ interests. Everything else is the purview of nonprofits or of government itself. I don't think that that's a complete view. I think that business leaders are also leaders. I think businesses are part of society. I think they have an appropriate role to take positions. I don't think that they should become, you know, openly political entities that go in a certain way. But they should take positions on things like democracy in America. Because to me, that's not a partisan issue. That's a requirement. So I think that we are confusing our partisan politics — and there's a certain amount of partisan politics that’s fine — with threats to our actual democratic system. If we break this one, we're not going to get another one. If we break this one, we're going to be in a place that I don't think we can recover from. So to me, this is one of those things that every leader can't step back from. Every leader has got to step up and say, “I, personally as a citizen, and particularly an influential citizen, have a responsibility.”

Alan Fleischmann 

And do you serve the private sector, public sector, and civil society, or just the private sector?

Stan McChrystal

We do both. For the first nine years, we did no public stuff. And then with COVID, we started helping states and cities respond to that threat, and it's expanded from there.

Alan Fleischmann

When you think about your military schedule, it sounds like you still keep it up. I'm curious about the advantage of getting up at 4:30 in the morning. What time do you go to bed?

Stan McChrystal

Well, the answer is early. I get up early because I have to work out, it's just psychological. So whatever time my day starts, I have to back it up so I can work out as much as I feel like I need to. But what that does is, by the end of the day… I tell people sort of laughingly that anything that happens after 9pm in our world, I'm not there for. Fortunately, I'm at that point in life that I don't care if I miss anything after nine o'clock, but I, typically at about 9pm, am out for the count. 

Alan Fleischmann

When you hit nine and are at an event, will you stay? Or if there’s a dinner, will you leave at eight?

Stan McChrystal

I will stay till nine and complain about it. If my wife is with me, I'll be leaning over and complaining. Or if somebody's at my house and it gets to be nine o'clock, I'll be going, you know, looking at my wife, “go get them out of here, make them leave.”

Alan Fleischmann 

Is there a secret to getting up at 4:30? You said you work out, so that's probably the biggest secret, giving yourself two hours to be ahead of the game.

Stan McChrystal

Yeah, you've got to because if you don't do that, I don't feel good about myself. It's part physical. And that's sort of self esteem.

Alan Fleischmann  

And then, do you work out at home, or do you go out?

Stan McChrystal

I do it right here now. I had my spine fused about three years ago, so I can't run anymore. But I walk and I carry a pack. This morning, I did a two-hour rucksack march. I do that every other day and on the other days, I have a home gym with an elliptical, a bike, and weights. I go up to this home gym, which is a little sanctuary, and I spend two hours in there. I like working out alone. I'm one of those people in a gym who wears headphones, so that if you come up and want to talk, I try to go, “no.”

Alan Fleischmann  

Yeah, “I’m not listening.” 

What are some of the other leadership lessons that you live by every day? That are like your daily prayers, that you think reaffirming allows you to navigate life’s complexities?

Stan McChrystal

Yeah, there are a couple and they’re very personal. The first is… I think that the biggest thing about leadership is self discipline. Most of us know how to be a good leader. The question is, will we do it? We know how to treat people. We know how to be thoughtful. We know how to do those things to be prepared and whatnot. But we don't always do them. I'm the same way. So the first and foremost thing is to try to focus on my own self discipline. I'll do what I know is right. I described my parents never doing anything wrong. I think that was an exercise in self discipline on their part. 

I think the second one is how you treat people. And when you get very senior like me when I was a four star, I might deal with 200 young soldiers a day as I turn toward the battlefield. And they're one of 200 young soldiers I'll have a one- or two-minute engagement with, but I'll be the first four star general they’ve ever met. When that meeting is over, it's likely that they're going to either call or write home and tell their family about it. They're either going to say, “Stan McChrystal, what a great guy,” or they're gonna go, “What a jerk.” So you get an opportunity that comes constantly. 

The problem is, you don't get them all right. A certain percentage of those, because I'm tired or I'm something, they're gonna write back and say he's a jerk. So the first step is to minimize those. I used to kind of… I still do this, I beat myself up every night over those things in a day where I wasn't as I should have been. The key is not letting that new, lower standard become the new standard. You can't say, “I'm a jerk because I'm a jerk, and everybody's just gotta get used to that.” You gotta be willing to say: “stop it.”

Alan Fleischmann  

It’s an expression I don’t really like, but how are you at work-life balance? I think there are either moments of intensity or moments where you need to be all in focus on other parts of your life. But how do you do it? And do look at life as one pie? Or are you looking at it as separate pies?

Stan McChrystal

No, I look very much at it as one pie, and I always had been that way. When I was in the Army, my life was that, and I didn't try to separate things completely. So a lot of people would look at me and say, “I don't do very well at work-life balance, because I integrate them all, I'm never really not working.” But I would argue I'm much more comfortable that way, so I'm happy. I have three granddaughters who live next door to me, I have a great time with them. So the reality is, I think the balance for me is good, but everybody's got to find their own. And if you're in that situation where you hate work, and therefore you live for that time off, I would argue that's not a good balance. If you hate either side of your life, you have to fix that side.

Alan Fleischmann  

And how did you manage to figure it out, then you could have three granddaughters next door, that you'd have your kids to be your next door neighbor?

Stan McChrystal

It's fun. We've only got one son, when I came home from Afghanistan he and his then-fiancé moved in with us. So we all were in this one single household for a while, then they got a separate place, and then they built a house next door to us, which just turned out to be a great setup. Of course, it's tricky, because you don't want to be too much in their lives and so we were pretty careful about that. On the other hand, having grandparents next door is comfortable. I've got a home gym, my son can use that. I've got a kegerator and that brings him over a lot. Then we can see the granddaughters a lot and we can be helpful. I think it's more like it may have been 100 years ago in America, where you're in a small town, where every generation of a family lives in that town. So instead of the grandparents going to Florida to retire and be away, we're more meshed on a constant basis. And I found that very comfortable. I hope they have.

Alan Fleischmann  

That's always been my dream. My daughters are still young enough that we don't have to think about that yet. But when I look at the future, the idea of having them in the cul-de-sac or having them as my next door neighbor seems like the greatest dream of all. So that's pretty amazing. 

Your book is amazing. Your books are amazing. As I said at the beginning of this, so many people I speak to quote you. I've had the pleasure to get to know you and I respect all that you do. And I just want to say thank you for joining us here today and it's been amazing. We could have another hour together.

You've been listening to “Leadership Matters” on SiriusXM and leadershipmattersshow.com. I hope you've enjoyed it as I have. We've been with General Stan McChrystal. Not only is he a former commander and an amazing public servant, he's been continuing to teach us how best to lead with great humility — enormous confidence, but with great humility — which we're very honored by as well. Thank you so much, Stan.

Stan McChrystal

Thank you, Alan. I appreciate it.