The one trait every leader needs today, with General Stanley McChrystal

13 May 2025 · 29 min

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Masters of Scale Podcast Episode Summary

Episode Title

The One Trait Every Leader Needs Today, with General Stanley McChrystal

Podcast Description On *Masters of Scale*, iconic business leaders share lessons and strategies for growing successful companies. Founders, CEOs, and innovators engage in candid discussions about their challenges and triumphs, guided by host Reid Hoffman.

Episode Overview In this episode, retired four-star General Stanley McChrystal discusses the critical importance of character in leadership during times of polarization, AI disruption, and eroding trust in institutions. He emphasizes that character is the foundation of effective leadership and shares insights from his new book, *On Character: Choices that Define a Life*.

Key Themes and Discussions

Importance of Character

  • Erosion of Character: McChrystal identifies a crisis of character in modern leadership, urging a shift in focus from policy disputes to discussions about character.
  • Demands for Character: He believes that both individuals and leaders should be held accountable for their character, stating that society's fabric is at stake.

The Nature of Fear

  • Insidious Fear: Distinguishing between immediate fear and a deeper, systemic distrust in institutions, McChrystal explains how fear can lead to isolation and a sense of threat from others.
  • Role of Rules: He posits that rules can create a framework for behavior that promotes trust and safety, allowing society to function optimally.

Character as an Equation

  • Character Equation: McChrystal defines character as an equation: Character = Conviction × Discipline. Both deeply held beliefs (conviction) and the discipline to live by them are essential; without discipline, convictions remain theoretical.

Human Imperfection

  • McChrystal acknowledges that everyone has moments of failure (e.g., being rude) but emphasizes the importance of aspiring to higher standards rather than accepting lower norms.

Political Landscape and Character

  • Critique of Leadership: McChrystal critiques the normalization of dishonesty among political leaders, asserting that character issues extend beyond individual leaders to a larger societal problem.
  • Business Leadership Role: He encourages business leaders to have the courage to adhere to their values, even when facing external pressures.

Military Perspective on Change

  • Need for Change: McChrystal discusses the necessity of change within the military, advocating for the adoption of new technologies and a focus on character over a rigid definition of warrior ethos.

AI and Warfare

  • AI's Impact: He acknowledges AI's potential to transform military operations but warns about the consequences of losing the AI race, comparing it to the historical significance of nuclear weapons.

Conclusion

  • McChrystal concludes that character is becoming increasingly essential as individuals gain more power through technology. He advocates for a collective return to prioritizing character in leadership roles across all sectors.

Key Takeaways

  • Character is foundational: Leaders must prioritize character to navigate today's complexities.
  • Fear and distrust: Addressing fear in society is crucial for fostering trust and cooperation.
  • Personal accountability: Leaders should stand firm in their values and be held accountable for their actions.
  • Embrace change: Adaptability, especially in military and business contexts, is necessary for growth.
  • AI and ethics: As technology evolves, the importance of character and ethical considerations in leadership will only increase.

Final Thoughts This episode emphasizes the need for strong character in leadership roles amidst a rapidly changing landscape characterized by distrust and technological challenges. General McChrystal's insights advocate for a renewed focus on integrity, accountability, and ethical leadership to forge a better future.

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Transcript

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1:17Character first is the essence of who we are. It is the most important measure of us and of our lives. regardless of what you proclaim to be your character. If you don't have the discipline to live it, you don't really have it. And in reality, if we go back to the saying, all it takes for society to fall is for a few good men to do nothing. I think all of our business leaders need to consider that. If the decision that I feel like I'm being pressured to make doesn't align with being able to look my granddaughters in the eye and explain to them what I did and why, that's not going to work for me.

1:59And I think at the end of the day, that is far more important than any short-term business advantage you might have.

2:15That's General Stanley McChrystal, retired U.S. military leader and head of the respected business consulting firm, The McChrystal Group. Stan is the author of bestselling books about leadership, risk and teams, but his newest book focuses on character. Stan argues that integrity and accountability are core to freedom and to lasting business success. He exhorts all of us, as a recent New York Times essay of his is titled To Be Not Afraid. In our talk, Stan gets into character's role in AI, warfare, and hot-button issues like Signalgate, transgender people in the military, and more. Stan's focus on honesty, unity, and courage make this a conversation that's sorely needed right now.

3:01So let's get to it. I'm Bob Safian, and this is Rapid Response.

3:11I'm Bob Safi, and I'm here with General Stanley McChrystal. Stan, thanks for joining us. Bob, thanks for having me. It's good to see you again. You first appeared on the show in the early days of the pandemic in 2020, and we talked about leading in a crisis, the need for adaptability and for collaboration in fast-changing environments. Today, the landscape is very different. no health trauma gripping the world, but the sense of crisis is back, certainly the fast-changing conditions. In today's uncertainty, you're focusing on character. You have a new book out titled On Character, Choices That Define a Life.

3:52Why character? Why now? Yeah, I think we have got a crisis in the country about character, or I would should say an erosion of character. And what I'm trying to do with this book is to begin a national conversation on character. I think we need to stop arguing about policies or politics or personalities. And I think we need to talk about character. And then last, I think we need to demand it. We need to demand it of ourselves, but we need to demand it of each other. And I think that would change some of the dynamics of how we interact. And I think if we don't do that, we'll pay a stiff price. One of the hallmarks of the pandemic was fear, fear of a deadly illness that could strike anyone anytime.

4:42You've been talking about fear today, but it's a different kind of fear. That's exactly right. I mean, we normally associate fear with a clap of thunder and lightning and it startles us. But this insidious fear is where you don't trust in the system or you don't trust that the things that you could count on before, the rule of law, the integrity of the people who lead us. And when you start to fear, you fear maybe you don't have protections, but you also start to fear them, people that you start to depict as the enemy, Maybe it's from a different group in society. This fear, it causes us to close up.

5:29We get more nuclear. We get more disconnected. Everybody's a threat. And so fear is often leveraged by certain people in society because it can get them political power. It can get them economic power. But ultimately, it undermines the things we need most. It's those relationships. It's alliances in the world. It's all the things that I think allow life to be a better experience. You've said that the remedy for today's environment of fear and instability is rules. Now, that could sound kind of authoritarian, that we need to restrict activities and ideas. That's not necessarily how you mean it.

6:17No, not at all. If you think about what rules do, they say what we can and can't do. Go back to school, things we were allowed to do or not do. The other thing rules did is it protected you from the bullies. What the rules do is they let us sleep at night. They let us feel confident that our families will be protected. All of the things that they give some structure, they're not designed as limiting factors. they actually increase our freedom because they're things we don't have to worry about. There's a difference between laws and socially accepted rules of behavior, right? Just because we can do something doesn't mean we should.

7:01You talk about that this is like a loss of internal discipline. Can you explain that? These are our personal choices? They are personal choices, but then they become accepted in society as we start to normalize behavior we wouldn't like. If somebody suddenly wants to attack you on social media, that's not technically illegal. If somebody comes out and lies about you, if they do all the kinds of things that undercut your business, What gives us the freedom to believe that we can function without having to worry about that every day? You said that character is like an equation. You have character equals conviction times discipline.

7:49Character first is the essence of who we are. It is the most important measure of us and of our lives. And it's what we should be thinking about that in regard. So what makes it up? I've come up with this equation, and it's funny because I'm terrible at math, but this seemed right to me. It's the things we believe in, and those I call convictions. It's deeply held beliefs, not just something somebody told us. It's something that we have decided that we believe. We pressure tested it. We thought about it for enough time where we go, this is something that I'm willing to live for or die for because it's that important.

8:33But that's only part of the equation because, Bob, you and I could have these very strongly held convictions, but if we don't have the personal discipline to live to them, they're kind of academic because if we say, I believe in integrity more than anything else, but as soon as it becomes convenient for me to lie or cheat, I do that, then I don't have the discipline to adhere to those things which I have professed to believe in. So I think it's the two. And of course, with multiplication, if either is zero, you have zero. And that's where your character is. So regardless of what you proclaim to be your character, if you don't have the discipline to live it, you don't really have it.

9:16You also acknowledge that we are human. So sometimes we, you know, maybe things go to zero when we didn't need to. You wrote something that I saw, we periodically may be despicable, but we should feel guilty when we do? Well, see, that's the point. That's exactly right. All of us are going to fail every day. You and I are going to go through any given day, and during parts of that day, we're going to be rude to somebody, or we are going to do something that doesn't really reflect the level of character that we want to have for ourselves. Now, if we accept that as the new normal, that's the new level, and I just live to that level, then it's pretty sad.

9:59What we have to do instead is say, okay, I got that wrong. I was less than I demanded myself, but it doesn't mean I'm going to allow that to be the new norm. I am going to force myself to try to go back to the level that I aspire to be. It's a constant struggle. I'm 70 years old now. And the reality is I still struggle with my character. I still work to define it. If every time we don't live to the standard, we look ourselves in the mirror and we say, you know, okay, that wasn't what I want to be. Then we have a chance of continuing to force ourselves higher. I was thinking about your commentary and focus on this issue of character in this moment.

10:46And, you know, someone could interpret this through a political lens as sort of a critique on the willingness of those in power to say whatever they can to get their way, whether that's denying election results or recasting January 6th rioters as freedom fighters. Are you critiquing Trumpism? I'm critiquing character in general. Now, Donald Trump, my feelings on Donald Trump are public knowledge, but he is not alone. In fact, if we look at, I was very disappointed in President Biden's willingness to sort of keep from the American people his physical condition. So I am unhappy that in our political world now, we have normalized people looking at the camera and lying, that we have normalized some of the demagoguery that occurs.

11:46And again, it occurs on both sides. So nobody should look at the other and feel self-satisfied. They should say, none of us are living up to what we want to. And I think it's even wider than politics. It's part of our society where we have people who are doing influencing and other things in a way that's not at all based on truth or reality. Our audience for this show is largely business people. What do you see the role of business leadership in a time like this? I know you work with a lot of businesses and business leaders. When you see how sort of some law firm, some universities, and some corporations, for-profit organizations are reacting to challenges from the government.

12:33You wish there was a little bit more bravery, more courage in some of that response? Yeah, let me start by saying I know how hard it is. Having courage in the theoretical sense when, they say you never get blitzed in the press box. It's easy from the stands to say those people on the field lack courage and all, but I am disappointed. And I do believe that there are many organizations that will regret not having shown an adherence to the values that I think they believe they have. And we find ourselves rationalizing to an accommodation that is not worthy of us. Your intuition will tell most of us what's right and what's wrong.

13:23You know, some people need a little help, but most of us have a pretty good sense of it. And then the question is just finding, do we have the courage and the discipline to live to it? But if you're tempted to come out with a response that in your heart, you know, doesn't align with your values, then I think that's a time you have to rethink your role. And maybe you got to step away from it. Maybe you got to say, the person in this job has to do things that I am unwilling to do. And that doesn't happen often enough in our society today. For people to say, it's not for me. I'm not the one to lead this organization in this time, in this kind of environment of conflict.

14:10or even more specific, if they are being pushed into a certain decision and they say, I am unwilling to make that decision. It is too incongruent with my beliefs and what I think is right or wrong. And that means you go down. That means you lose the job. That means you, and that can hurt. One of the things that, you know, I used to tell military leaders, every time you're placed in command, which is a sacred responsibility, you have to think of it as your last command. Don't command like you want to think about your promotion to the next level. Because if you do, you'll find yourself overly conservative, very cautious about things, and you often won't do things that you really think you ought to do.

14:58And so you have to think about, I am going to do the best with the responsibility I've just been given. I want to double-click on what Stan is saying here, that leadership really is about taking on heat for the things that you believe are most important, even if that costs you your leadership role. This is something that Stan himself did in his military career, by the way, and it's one of the reasons he's so respected today. As business leaders at all levels contemplate their actions in the face of hostility from government, from shareholder activists, from employees, what is the right way to exercise character?

15:34When is it courageous to speak out? and when is it courageous to rethink your beliefs. We'll talk about that and more after the break. Stay with us. Real leaders don't back down when the stakes are high. They innovate, they push forward, and then they take the stage at the Masters of Scale Summit. Join us in San Francisco, October 7th to 9th, to hear from the CEO of the New York Times, scientists using cutting-edge technology to find cures, the leader of crypto powerhouse Coinbase, a retired four-star general, and many, many more. Apply now at mastersofscale.com slash apply25. That's mastersofscale.com slash apply25.

16:22If you're ready to take your startup from idea to impact, then AWS is your launchpad. From data storage to machine learning to secure app hosting, AWS gives you the tech trusted by the world's fastest scaling startups. And here's the best part. Join AWS Activate today and you could score up to$100 ,000 in AWS credits tailored to your stage and network. Go to aws.amazon.com slash activate and start building. Expanding your business in the U.S. can feel like a maze. Every state has its own payroll, benefits, and compliance rules, which can pull your focus away from growth. That's why founders use Deal.

17:05Deal is the professional employer organization, or PEO, that gives you a dedicated HR expert plus Fortune 500 level benefits for your team. The National Association of PEOs says businesses can grow twice as fast if they use one. So if you're scaling, make it simple with Deal. Go to deel.com slash mos and get up to three months free. Before the break, General Stanley McChrystal talked about the importance of character in addressing today's biggest challenges. Now Stan talks about how character is unfolding in the U.S. military, what most upset him about the SignalGate fiasco, how AI is changing modern warfare, and more.

17:50Let's dive back in.

17:55I wanted to ask you about the changes that are afoot in the military, in the Department of Defense. Some folks champion the idea of change. You know, some folks make dire predictions. For you, who have, you know, worked with military and military leader for a long time, what's your perspective about what's being attempted? I would say first, if I go to 30 ,000 feet and look at it from a big distance, change is needed. Change is appropriate. And I think it's going to mean significant change, adoption of new technologies, changing of force structures, all of those kinds of things. All of that is correct.

18:37even firing generals, if it's necessary, is a good thing. If you are firing generals because they don't have the skills or they don't have the right personalities. So all of those things I completely sign up for, and I wouldn't recognize a lot of sacred cows that would be exempt from hard scrutiny. Now, having said that, I am not aligned with where the current Secretary of Defense, how he defines some of the current issues and the direction. He talks about the warrior ethos, but the reality is what we are trying to do is get the best military we can. And that's not necessarily the strict warrior ethos because soldiers are a little different.

19:31Soldiers are disciplined. They follow the rule of law. When you think about warrior, it's got a little bit of a looser definition or interpretation usually. So that I think is probably a mistake. If you start to say you can't have transgender soldiers, My response would be, one, there aren't many, but two, if a transgender soldier is really good, we need them. We don't have that many extra people that are really good that we can afford. So I have a much different definition of what a really effective service member might be. I think I do. And then I also think that if you are judging military leaders on a political ideology, you're playing with fire.

20:24And here's why. We've had this extraordinary couple of centuries of the U.S. military being pretty apolitical. Not always perfectly, but generally very apolitical. And although there's friction between civilian leadership and uniforms, it's one of the healthiest relationships that you've seen on the globe for 200 years. Once you start to hire and fire senior leaders based upon their political alignment with any particular ideology, you are going to affect younger military leaders. They are going to shape their behavior. They're smart people. They'll look up and they'll say, this is what it takes to succeed in this business.

21:09And they will start to represent that behavior. And a decade from now or two decades from now, we'll have a very different kind of military and we won't like it. It will not be the apolitical, very professional force that I knew and that I think is largely the case today. So I think it's understanding the danger of that dynamic that is really critical. The issues around security, this signal gate scandal, using publicly available tools to communicate, is that really a big deal or is that like sensationalized? I mean, I know sometimes in theater you had to act fast and maybe couldn't always use every tool that you wanted.

21:52What do you see about what was going on in this particular situation? One, I do think it's a big deal. I think using signal, even though it's encrypted, it's not secure. And so you are transmitting future plans on an unsecure device, which is extraordinarily dangerous for the men and women who are going to go execute that operation. So I do think that was a big deal. It was almost a reflection of amateurism. Now, the other side of it bothers me far more. we had the mistake it comes out everybody knows it's a mistake they know that the information is extraordinarily sensitive and they get up in front of cameras and they say the information was not classified now they know that that's not true they know that's a lie it is classified and yet they look at the camera and they say something that maybe most americans can't parse the difference, but anybody who's involved knows that people whose salaries you and I are paying in positions of great responsibility consciously and intentionally don't tell the truth to you and I.

23:08That's a big problem. And that's the far greater issue here. We can minimize the event that it occurred as a mistake, but we can't minimize the lack of integrity. There are things where like half the country believe that one group of people are just lying and half the country believes another group of people are lying about sometimes about the same things. And it's it does get hard for people to parse, you know, who is acting with character when you're in that kind of noisy environment. It's extraordinarily dangerous, too, because we think about it, go to a war, a major war, and you typically have two combatants and your side's right and their side's wrong.

23:56And if you switch positions, you're going to feel the same thing. Your side's right and their side's wrong, but you're now on a different side. And so the reality is both sides start to just make the assessment that, as you say, that we are for truth and goodness, they are evil, and vice versa. The truth is usually in the middle, and yet when we make that straight distinction like you do, we communicate to our own populations what we want them to believe. We do information operations on ourselves, and over time, you convince yourself more and more that, yeah, I'm right because I'm on this particular team.

24:42If you and I had grown up in South Carolina in the 1850s, we'd have joined the Confederate Army. Statistically, we would have. When we can say, no, we think slavery was bad, but we think it 170 years later. The reality is we probably would reflect the life's journey that we've had. The key thing here is to respect the reality that your life's journey may not be complete and it may not be right. I'm curious how you look at AI's potential impact on the military and how do we know if we're ahead or behind, especially in that competition with China? Yeah. We've never had anything quite like this. The closest analogy in my mind would be nuclear power, atomic weapons.

25:31And we got them first during World War II. We won the race to produce nuclear weapons and then used them first. And when other countries followed us and developed their own nuclear weapons, we got this sort of balance. The problem with artificial intelligence, and I've had the opportunity to do some work and a big war game on it, is that if somebody achieves artificial general intelligence before their competitors, theoretically, they could then sprint ahead in a way that their competitors almost couldn't catch up. And you could have a dominant superiority. And we're not even 100 % sure what AI will do on the battlefield.

26:21We know it will make a lot of things simpler, faster, easier, logistics, planning, all those things, which will make an army more efficient. But as AI starts to do target discernment, autonomous engagement with weapons systems and robotics, we have an incomplete picture. You know, Ukraine's like a glimpse of the future. We have an incomplete picture of how dominant that will be. So I don't think there's any time except the pursuit of nuclear weapons where this idea of losing the race could mean losing the war. And when you think of AI, you have to blur the lines we had for many years of military power and separate from diplomatic or commercial power.

27:11those things are now so interwoven because the ability to leverage AI in production and things like that could give a country a decisive advantage that immediately shows itself in the military sphere. So I think first, I think two things have to happen. We need to be pursuing those kinds of regulations and understanding around the world that give us some opportunity to put rules and norms in place for AI, but we're not close to it. But parallel to that, we need to be at breakneck pace trying to develop AI. And those seem in tension, they seem in contradiction, that here we are trying to develop new nuclear weapons, And at the same time, we're trying to set up rules to limit their use.

28:06But if we lose, if we don't get at least nuke or at least parity with AI, then we're going to be in a position that's extraordinarily dangerous. And that's, again, it's not going to be the military. It's going to be this broader national effort. And the topic of character that you're so focused and compelled about today, that applies to AI, too. and how we talk about it, whether it's commercial uses or military? Well, I would argue the character becomes more important because the power of the individual is dramatically more than it was even 200 years ago. We think of the old saying about Samuel Colt who created the six-gun.

28:50We say, God made man, Sam Colt made him equal. And he leveled the playing field for people who weren't as big and strong because they could have an effective weapon. AI is going to do that and give extraordinary power, not just to nation states, but to individuals. And so those people who have that extraordinary power, and almost all of us will have some form of it, have the ability to do great good or just great evil. And so character, I think, is going to become more essential than ever. There's a lot at stake in this moment right now where we are. I mean, we're kind of on a precipice. I think we are.

Read the full transcript

29:37I think we're on a practical precipice in terms of the future of the nation, the fate of the United States, or even the fate of the world. If we're talking about making America great again, let's talk about making character central again. Let's talk about focusing and demanding character. Well, Stan, this was great. And I always appreciate you talking with me. Thanks for doing it. You're so kind to have me. And Bob, thanks for all you do. I was grateful to welcome Stan back on the show during this tricky chapter in our world today. He's got a way of boiling things down to their essence, a discipline that helps distill what's most important.

30:21The choices of business leaders, of military leaders, of all of us, They do more than impact actions today. They set the tone for the future. And it underscores the question, what kind of a future do we want? AI, the U.S. military, the worlds of business and of politics, it's all interconnected like never before. For good or bad, that puts more pressure on all of us in every realm to be better leaders. Leaders with integrity, with courage, and as Stan would say, with character. I'm Bob Safian. Thanks for listening.

31:05Meet Nicole Nicholas, Capital One business customer and co-owner of Ansett Uncles, a plant-based restaurant and community space in Brooklyn, New York, that got its start from a need for unity. The inspiration, it was born from the desire to create a space that felt like home, where we can connect community culture, good food, and come together with family and friends. That's how we birthed aunts and uncles. Nicole and her husband, Mike, were fulfilling their dream of bringing people together out of their home kitchen. But they soon learned that the demand for community was greater than they knew.

31:36It became overwhelming and we were like, we need home, but not in our actual home. We realized that there was also a need in our community for something bigger in our neighborhood. So we had to find a place. Moving from a home operation into a storefront was a huge next step. But Nicole and Mike were able to take it on with the help of Capital One Business. It's not for the weak as a small business. Finding resources is super important because that's the way you'll be able to manage and scale. We would have never done that without having Capital One to be able to help us along the way. The cashback rewards are very helpful.

32:11So, you know, it just gave us that runway to be able to breathe a little bit. Then you get to focus on the cooking of the food and making the experience great. To learn more, go to CapitalOne.com slash business cards. AI agents can make your teams more productive, but if they aren't connected to other agents or your data or your existing workflows, they can only take you so far. Any business can add AI agents, but IBM connects your agents across your company to change how you do business. Let's create smarter business. IBM. Rapid Response is a Wait What original. I'm Bob Safian. Our executive producer is Eve Trow.

32:52Our producer is Alex Morris. Associate producer is Mashimaku Tonina. Mixing and mastering by Aaron Bastinelli. Our theme music is by Ryan Holiday. Our head of podcasts is Lital Malad. For more, visit RapidResponseShow.com. Thank you.

From the publisher

Amid polarization, AI disruption, and eroding trust in institutions, retired four-star general, Stanley McChrystal, argues that what leaders need now more than ever, is character. Head of the business consulting firm McChrystal Group, Gen. McChrystal returns to Rapid Response to discuss his new book on the subject of character. From AI ethics and modern warfare to hot-button issues like Signalgate and transgender service in the military, McChrystal explains why character is the foundation of lasting leadership. Drawing from decades of experience, he urges today’s leaders to start standing up for what matters and “be not afraid”. 

More details about On Character: Choices that Define a Life here.

Visit the Rapid Response website here: https://www.rapidresponseshow.com/

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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