473 Strategy Means Choice: What Washington, Grant, and Eisenhower Teach Us About Leadership with Matt Cavanaugh
Key Takeaways
- Strategy inherently means making difficult choices, and effective leaders must accept that these decisions will inevitably disappoint some stakeholders and ruffle feathers.
- Superior judgment separates exceptional strategic leaders from average ones, and this capability is developed over time through lifelong learning and learning from early stumbles.
- Historical commanders like George Washington, Ulysses S. Grant, and Dwight D. Eisenhower demonstrate that emotional intelligence and political instincts are vital strategic capabilities for managing complex relationships.
- True strategic leadership requires balancing openness to competing perspectives with the conviction to make a final choice and stand by it under intense pressure.
- Even the most advanced technologies, such as artificial intelligence, can assist with prediction and information processing, but they cannot carry the human consequences of ultimate strategic judgment.
Most leaders understand that strategy requires choices. Fewer are prepared for what follows: disappointing people, committing resources under uncertainty, and accepting responsibility when the consequences are significant. Those pressures are not unique to the battlefield. They show up whenever CEOs and senior executives must choose a direction while facing incomplete information, competing stakeholders, and no risk-free option.
In this episode of Partnering Leadership, Mahan Tavakoli speaks with Matt Cavanaugh, a military strategist, combat veteran, former West Point professor, and author of Who Wins Wars? Lessons in Leadership, Power, and Supreme Command from Washington, Grant, and Eisenhower. Drawing on more than a decade of research, Cavanaugh examines what separated these commanders from the capable opponents they faced and what their decisions reveal about leadership under pressure.
Rather than treating victory as proof of brilliance, Cavanaugh looks closely at moments when outcomes remained uncertain and leaders made consequential choices. He explains how Washington survived repeated tactical defeats, why Grant refused to follow the accepted rhythm of Civil War campaigns, and how Eisenhower weighed conflicting advice before one of the most consequential military operations in history.
Their success depended on more than courage or military expertise. Each leader had to absorb competing perspectives, manage political relationships, understand adversaries, work within constraints, and then exercise judgment. The conversation explores the balance between openness and conviction: listening broadly enough to see the situation clearly while still accepting the responsibility to choose.
Cavanaugh also considers what these lessons mean in an age of artificial intelligence. AI can expand the information available to leaders and strengthen their thinking, but it cannot carry the human consequences of a decision. For leaders facing higher stakes and accelerating change, this conversation offers a historically grounded examination of how judgment develops, why strategic and tactical excellence are not the same, and what it takes to lead when there is no obvious answer.
Actionable Takeaways
- You’ll learn why strategy inevitably disappoints someone and what that means for leaders who mistake broad agreement for strategic clarity.
- Hear how Washington, Grant, and Eisenhower developed superior judgment rather than simply possessing it from the beginning of their careers.
- You’ll learn how to distinguish strategic leadership from tactical excellence, including why an organization can execute exceptionally well and still lose the larger competition.
- Hear how Eisenhower evaluated sharply conflicting recommendations before D-Day and accepted personal responsibility for a decision with enormous human consequences.
- You’ll learn why emotional intelligence is a strategic capability, not merely a tool for maintaining relationships or improving morale.
- Hear how great leaders combine openness with conviction, taking in competing ideas before choosing a direction and staying with it through criticism.
- You’ll learn why no strategic leader succeeds alone and how Washington, Grant, and Eisenhower used advisers, councils, and trusted colleagues differently.
- Hear how effective leaders work within political and resource constraints without allowing those limitations to become excuses for inaction.
- You’ll learn how AI can amplify strategic thinking while leaving consequential judgment with human leaders who remain responsible for the outcome.
Connect with Matt Cavanaugh
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Frequently Asked Questions
What does Matt Cavanaugh's book Who Wins Wars focus on?
Matt Cavanaugh's book examines the leadership, power, and supreme command of George Washington, Ulysses S. Grant, and Dwight D. Eisenhower by analyzing pivotal one-year periods where the outcomes of their respective conflicts hung in the balance.
How do military strategy and business leadership intersect?
Much of modern business strategy is derived from military strategy, particularly regarding how leaders funnel competing options, make high-stakes choices under uncertainty, and navigate complex political environments like boards and executive teams.
Can superior judgment in leadership be developed over time?
Yes, superior judgment is not purely innate; historical commanders like Washington and Grant experienced early stumbles and actively developed their decision-making skills through continuous learning, reflection, and experience.
Why is emotional intelligence considered a strategic capability?
Emotional intelligence allows leaders to connect with people at a gut level, understand diverse perspectives, manage political partners, and accurately assess opponents or competitive environments.
Welcome to Partnering Leadership, a top global leadership podcast for purpose-driven leaders with a growth mindset, seeking to learn from the leadership journey of change makers and business insights from leading global thinkers. For additional leadership insights and bonus content, visit us at partneringleadership.com. Now here's your host, Mahan Tavakouli.
SPEAKER_01Matt Kavanaugh, welcome to Partnering Leadership. I am thrilled to have you in this conversation with me.
SPEAKER_02I'm thrilled to be here. I've listened to a bunch of the episodes and I'm excited to participate.
SPEAKER_01I love your book, Who Wins Wars: Lessons in Leadership, Power, and Supreme Command from Washington, Grant, and Eisenhower. So much brilliance in that history, Matt, and so much relevance to strategic leadership. But before we get to that, would love to know a little bit more about you, Matt, whereabouts you grew up and how your upbringing impacted who you've become.
SPEAKER_02I'm from St. Paul, Minnesota. So for those of you that are international, I'm from the northern central part of the United States. A lot of people think of it as a cold place, and they would be right to think that my fondest memories of growing up were playing outdoor pond hockey all winter long, all over the winter break. And the reason that's relevant is that I grew up idolizing the 1980 U.S. Olympic hockey team. And it's not hard to figure out why 12 of the 20 players on that team were from Minnesota like me. The head coach Herb Brooks was from St. Paul like me, and they gave me something to look up to, something to want to be someday. And it's not surprising that I would decide to join the Army and fill a full career in the Army, in part because I wanted to wear an American flag patch on my shoulder. But a lot of your listeners will know that was a team of college kids that beat a Soviet hockey machine that had won several Olympic Games in a row, that had recently beaten the NHL All-Star team before that 1980 US Olympic, that U.S. Olympic game. And I watched growing up and idolize that team. And it I really stepped away from them with this message that miracles happen when we make them happen, when we have the strength to try something different, to do something different. And it became something for me to want to live up to.
SPEAKER_01What an outstanding story in terms of your pride and also the underdog element to that story as well, Matt. Now, one of the things I was really struck by is your McMaster story. I want to understand what you learned from him and that experience, and then how that transfers to organizations as well.
SPEAKER_02Yeah. So when I served in the Iraq War, and I served in the Iraq War at the very, very beginning, at the end of the ground war, I spent a little over a year in Iraq and then came home and then went right back. And the second time that I was in the desert, I served under then Colonel H.R. McMaster, who many people would know, went on to become Lieutenant General McMaster and the national security advisor of the United States during the first Trump administration. And I will tell you that you could see what a difference a general makes. You could see what a difference a strategic leader makes. General McMaster, then Colonel McMaster, saw the war in its largest context, and he saw our particular part in the war in its own context as well. And I'll tell you, we were serving in a community of about 250,000 people in the northwestern part of Iraq. And we arrived, and there was an element that was undermining the local government in that particular community. It's called Talafer. It's to the west of Mosul. And Colonel McMaster over the course very patiently over the course of many months built this giant earthen berm, this earthen wall around the entire city in order to later control who would enter and leave the community, and then very methodically work our way through the city to clear it of terrorists or folks that were anti-the local government. And it later became known as the clear hold and build strategy in Iraq. And it took an awful lot of resource, it took a lot of patience, but it worked. And it was this opportunity to see between the two years in Iraq what the different strategic leadership can make in a particular military problem, right? And I know many of the listeners are obsessed with business problems. And I also know that most business strategy is derived from military strategy. To me, I see clear translations here, right? Sometimes the stakes in business aren't as high as they are on a battlefield. But the stakes are still high. You can still see what a difference a strategic leader can make. That was the starter's pistol for this book. What makes a great general great? And why? How does it work? And so for me, launched this longer than a decade period of very serious and sustained study of strategic leadership.
SPEAKER_01You spent about 10 years studying these generals as well as the wars. Before we get to that, I'd want to go a little deeper into General McMaster. He eventually became General McMaster, but he was very candid with people around him. And as a result of that, even though he was as strategic as you mentioned, he wasn't promoted. So here you have someone who is strategic who does what many leaders uh say they want others to do, which is speak up and voice their opinions, but then that worked against them.
SPEAKER_02Yeah. When you get down to it, strategy means choice and choices hurt feelings. And he made decisions that ruffled feathers.
SPEAKER_01Matt, I have to stop you just to underline, I love that. Strategy means choice, and choices hurt feelings. Yes. You are not going to be strategic, whether it's in Iraq or for your organization, without the willingness to hurt some feelings, you're not going to get consensus on the best strategy.
SPEAKER_02That's right. We're going to get into this when we talk about what my model of strategic leadership looks like, but it very much looks like a funnel. A strategic leader is like a funnel. All these different options and ideas and choices and different interpretations come in through the top, and one choice needs to come out the bottom. What we want from our strategic leaders is superior judgment, better decisions, not good, bad, superior or inferior. And the best of us that are the best at that process have this sense of two things. And one is like a sense of grit to make a decision and stick to it, even when it hurts. And then the other part of it is a sense of empathy, right? Understanding that we live in a world of human beings, and those human beings have feelings and we need to navigate that. And that sense of emotional intelligence isn't just good for keeping our side together. It's good for understanding your adversary and understanding the environment that you're trying to navigate. And so I think a guy like General McMaster saw the bigger picture, saw all these different options and ideas. He picked one. He had the guts, iron gut to stick to the right decision, even though he stepped on some toes and was passed over for promotion. And it took extreme intervention for him to earn his ascension to his first general star. And he earned that. He really did very much. And the preface to the book is titled, Not All Generals Are Created Alike. And it's also true, not all strategic leaders are created alike, right? Strategic leaders are like human beings. Most of them are average, some of them are terrible or borderline insane. And then there's a small class of them that are the peak that we want to grow up to be someday. And those are the ones that I'm writing about in this book.
SPEAKER_01I love that. And I also love the fact that you emphasize the importance of superior judgment. So one of the elements, Matt, we go on a slight tangent a little bit, is that one of the people who started me in understanding AI's implications on society and organizations was AJ Agriwall, about eight years ago, wrote prediction machines. And AJ talks about how AI reduces the cost of prediction to near zero, that increases the value of human judgment drastically. So the fact that judgment will play a bigger role in our future than we expect. So now you have mentioned a few times the importance of superior judgment. Based on your study, is this something that can be developed, or did these generals have superior judgments?
SPEAKER_02Not from birth. Not from birth. The three supreme commanders and strategic leaders that I'm taking a look at are George Washington, Ulysses S. Grant, and Dwight David Eisenhower. And what I'm doing is I am balancing them against their principal opponents. So I'm not just looking at them in isolation. I'm looking at them in the competition they found themselves in. And what you find is all three of them, earlier in their lives, they're like the rest of us. They made bad decisions. They did. And they went through a process of learning. George Washington had stumbles. And in a lot of ways, George Washington might be the losingest tactical general the United States has ever had, but he won the war that mattered most. Let me just emphasize that for a moment. In June and July of 1776, George Washington had about 16,000 troops spread out over the New York City area. Well, we know is New York City today. The British invasion force that arrived off New York Harbor was over 42,000 troops, over 400 ships. And in today's population figures, that would be like an invasion force of 6 million arriving off the coast of New York. And it what basically happens in that summer in through the fall is Washington gets beaten and beaten and beaten until he pushed all the way out into New Jersey and then famously counterattacks at Trenton and Princeton on Christmas Day and in the new year of 1777. And the American Revolution survives. Truly, if America was ever an infant in a crib, this was the moment. This was when Thomas Paine wrote the line, these are the times that try men's souls. He was with Washington's army. And Washington's superior judgment is what kept the American idea alive. Grant was, as a junior officer, average, maybe even you could say below average, but he really comes into his own during the Civil War, commanding these large formations. And General Eisenhower was a lieutenant colonel when the war began. And within three and a half years, he went from lieutenant colonel to brigadier general to major general all the way to his fifth star. And he's commanding the largest invasion force that humanity has ever put together. What you find is that it's almost unfair to try to figure out who is going to be able to handle these kinds of circumstances, the heights of strategic leadership. But there are some little breadcrumbs we can follow, right? Like I mentioned earlier in our conversation. How it try to dig into someone's strategic decision process, understand how they take information in that funnel and they come, they arrive at a particular judgment. Another one is how well, what is their emotional intelligence like? How well do they relate to other people? Because strategic leadership at its core is seeing the world one way and attempting to leverage a whole organization to try to change it in some way of your making. That takes lots of people, right? It's really difficult to do. And if you don't understand people and connect with people at a gut level, you're not going to succeed at it. And then when you have to make a hard call, do you make the hard call? And some of these commanders, some of these gentlemen, they made the hardest calls you can possibly imagine. And it was gut-wrenching for them, truly gut-wrenching.
SPEAKER_01So I would love to understand them a little bit better, Matt. One of the things I was wondering as I was reading about them, and I wonder all the time when I read about success, whether business success or in this case military success of these generals, I go back to Annie Duke, the champion poker player. And resulting. Is it that these are three generals that won for a bunch of different reasons? Yep. And therefore we go back and study them and say, aha, this is what contributed to success. You're asking a wonderful question. Is it that they actually contributed to that success?
SPEAKER_02That's right. The way that I describe it in the book, imagine a poker game and you have two players with equal amounts of chips at the start of the game, at the end of the game, one player has all the chips, the other player has none of the chips. You can rewind the clock or rewind the tape on their match, and you can see the moment at which we were at a FET accomplished. We know that this particular player is going to win. This straw is the one that broke the camel's back. We obviously can't run experiments when it comes to military wars like this. But what we can do is we can zoom in on a moment where the outcome was still in doubt, right? A moment where the war or competition could have gone either way. And what we're doing in this book in particular is I'm taking about a one-year period of time. And the reason that I take that long period of time is that it eliminates luck from the equation. Luck can turn a particular moment or a day, but it can't explain a campaign or a career, right? And so when we zoom out to that sort of one-year period, we can identify major strategic judgments that the two commanders are making that bounce off of one another. So I'll give you an example. Most folks are familiar with the American invasion of Normandy, D-Day, so to speak. And actually, there's a movie out right now called Pressure that's about that decision to launch the invasion on that particular day, right? What most people miss is that Eisenhower didn't just make one decision and say, yes, let's go today. There were a number of decisions surrounding the entirety of the invasion. So, for example, many people know that the United States and the Allies made airborne drops on D-Day. So there were two American airborne divisions and then a combined Allied division that dropped right behind the German defenders on D-Day. The idea being that you basically try to get the defenders to turn around instead of facing the beach, right? So they're worried about two different sides. A little over a week before the invasion, Eisenhower's air component commander comes to him and says, Sir, we cannot make the airborne drops because I estimate and assess that 70 to 80% of them will be combat ineffective. They'll either be killed or wounded. So if we do it, we'll just be dropping these guys to slaughter. Another option out there was General George Marshall back in Washington, D.C., told Eisenhower, I want you to make the airborne drops two-thirds of the way to Paris. Because what we're going to do is we're going to leapfrog ahead. We're going to do a deep envelopment of the enemy. And then Eisenhower's ground invasion commander said, I need those drops right behind the beach because they're going to have the maximum impact there. Those are three different options coming into that funnel, right? And Eisenhower, he goes into his own like little command room by himself and he writes down, this is the most soul-wracking decision you could imagine. Because if I'm wrong and I drop these three airborne divisions behind the Germans, and 70 to 80% of them are killed or wounded, that's on me, right? Everybody's looking to me to make this decision. Of course, he made the decision. They did make the drops. Only about 8% were killed or wounded, and it worked, right? And actually, his air component commander wrote to him, Sir, I'm so sorry to have added to your list of concerns. I genuinely believe that's the way things would turn out. On the other side of the field, Adolf Hitler is deciding how to defend the beach. And he has 10 divisions to spend for reserve. Erwin Rommel wants all 10 of those divisions placed right on the beach. Because by his experience, that's the best place to put his mobile reserve. Another German general wants to put the 10 divisions a little bit further back so that they can respond to anywhere on the beach, on northern France, further south, wherever. Hitler decides to split the baby into three. He takes three divisions and places them far forward, right on the beach. Three divisions puts them in the middle, and then hold four divisions in reserve for only his release authority. I'm this is just one case that I'm trying to draw out. But we can see in hindsight, through looking at dispatches and decisions and memoranda, those two strategic judgments that those competing commanders are making, one is objectively better than the other. And we can see in part, not all the way, but in part, why strategic leadership makes a big difference.
SPEAKER_01What a beautiful example of it. And what a powerful way to describe it, Matt. I was mesmerized, just listening to you go through the example. Again, the one thing I do wonder as I listen to this, I am in awe of Eisenhower being able to do this, is that we spend $50 plus billion dollars a year on leadership developments. And now let's say focusing on judgment as well. I still wonder in what ways can that be developed? Are there patterns you saw in these experiences that tells you this can be worked on and developed? I know they developed it. Can we develop it?
SPEAKER_02100%. So I think there's a cycle in strategic leadership. There's like a challenge that emerges, right? So you have a challenge that emerges. There's a choice that has to be made. There's some clash. And strategy doesn't matter if you're the New York Yankees and you're facing A little league team. It's not a big deal, right? Your natural imbalance in talent is going to make all the difference. But the reality is when the state, when the two sides are relatively closely matched and the stakes are high, strategic leadership makes a big difference. So there's a clash and then there's consequences that result from that. And I really feel like while we can't crawl inside the brains of these particular individuals, we can see what their decisions were made. We can see the artifacts of their thinking. And then we can go back and we can take a look at some of the characteristics that followed along with some of those particular things. And one of those is all of them had political instincts, emotional intelligence. They really did connect well with others. They had the skills to persuade others. If you look at their writing, which I think is a direct translation of clarity and thought, Washington, Grant, and Eisenhower were exceptional communicators, and they were very good at that. Another one was we focus on degrees and we focus on things that you hang on the wall. But all of these were lifelong learners of the first order. Washington had this massive library that he kept at Mount Vernon, and he was interested in everything. You name it, plants, animals. He had books about military strategy. He had books about religion. He had lots of fiction. Grant, the saint, was a lifelong learner and reader, and the same for Eisenhower. In fact, actually, mid-career Eisenhower was offered an opportunity to leave the military and to become a journalist because he was such a quality writer. They all had childhood challenges. They came, all three of them came from what you would describe as not terribly wonderful home environments from when they were growing up. And then lastly, they were pretty young. They were all in their 40s or early 50s. I think that these sort of lists of characteristics, while they don't apply to everybody, I think there are some of those breadcrumbs we can follow.
SPEAKER_01Now, looking at all of them, particularly in Washington's case as well, there is an element of politics that they had to maneuver around as well. It's one of those things that sometimes people don't really reflect on and recognize with respect to military. So when I deal with CEOs, they're talking about the stakeholders, they deal with the board members, all the different ways they're being pulled in different directions. One of the things that comes across is how in every one of these instances, these individuals didn't only have to command the military, they had to be involved in a very complex political environment and manage all of those relationships as well.
SPEAKER_02So if I'm translating it to business, it's a CEO that's operating with a chairman or a board, and you are doing two things simultaneously. It's almost like in nature, an eagle or many hawks that fly have this visual ability to have almost picture in picture. So they have both a very focused view of their target on the ground, but they also have this wide angle lens at the very same moment. I think what you find in strategic leadership, when it's at its peak, when it's at its best, you have someone who's maximizing for a particular focused objective. And for these Supreme Commanders, it's battlefield results and strategic awareness of how they stand in relation to their competitor. But in the very same moment, they're also operating in democracies where that emotional intelligence is kicking in and they know that they also have to keep their political partner onside and on board. And there's really striking examples of that. So I mentioned Washington in New York, right? He's completely overwhelmed by this British onslaught. That invasion force that the British sent was the largest invasion force the British Empire had ever sent anywhere. When they were abandoning the city, the Continental Army, amongst the general officers that Washington is with, most of them want to burn the city of New York, to deny it as a winter haven for the British. But the Continental Congress had expressed to Washington that they wanted him to hold New York, right? So he's got this tension between military necessity and what politics is driving him to need to do. He navigates that tension very, very methodically, but he does eventually leave the city without burning it because he knew how important the political side of the effort was. Because the moment that the American public started to see that the Continental Army was not, it might send a chill into Philadelphians that the Continental Army might be burning their city next, for example. Like another example is that General Grant is fighting while his political partner, President Abraham Lincoln, his boss, is campaigning for the presidency. And he knows that if Lincoln loses the election, the war is over. Maybe not in a military sense, but in a political sense. So he's also got to navigate those tensions as well. So those tensions that exist in every boardroom in America or around the world exist in battlefields and with amongst democracies as well. And I feel like that's a very healthy tension in the sense that you could easily imagine a situation where a military leader is exercising judgment without any oversight. And that's a dangerous thing. That's a dangerous thing because there is no feedback loop. There is no feedback loop. And the feedback loop on a battlefield is a really painful one.
SPEAKER_01Yeah. And I wonder whether it was with Hitler's case or Putin's of the world, whether that ends up costing them in the long term because they don't have that feedback loop.
SPEAKER_02I definitely agree. And you should know, by the way, that's part of the case with Hitler was that he was overruling his military leadership so much and so often that you can easily see that the German high command was just non-existent and was very detrimental to their strategic performance. Pound for pound, there have been studies that have shown that in terms of killed, inflicting casualties on the opponent, and then receiving casualties from the adversary. The German army in the First World War and the Second World War was the most tactically effective in both wars, and they lost both of them. This is the difference between tactics and strategy, very much that lesson to me is really important.
SPEAKER_01Another thing that struck me with respect to strategy, and I think they all have this in common, most specifically Washington and Grant, it's almost as if they changed the game. The same way organizational strategy, a lot of times, the most effective organizations that break through, they change the game rather than trying to play the old game. We'd love to get your thoughts on that as well, Matt.
SPEAKER_02This is the thing that Sun Tzu was getting at attack the enemy's strategy. I taught for many years at West Point, and Sun Tzu is tough to teach because it's kind of like the buy low, sell high approach to strategy out of course. But when you are able to change the contours of the competition in a way that alters the competition in your favor, it's always like to me, it's the one strategy that really does always work. And with Washington, he was looking to exhaust an adversary. They had more of them. On some level, they had so many advantages. And there's a moment in time in late 1776 where General Howe is pursuing the Continental Army and makes the decision to suspend his campaign for the winter, just to stop fighting, just to put the brakes on the campaign. And Washington's great, to his great credit, he saw this moment in time as an opportunity to counterattack against a force that in almost every way was superior to him. Like I said, he had lost battle after battle after battle. And with Grant, the way of the civil war was often that you would fight this big battle, and both sides would go to their corners and lick their wounds and recover for a month or two until they assembled on another battlefield. And Grant made the decision to say, no, we will make this a continuous fight all the way till the end. And Grant didn't do that with great happiness in his heart. There are several recorded instances in the historical record where during this campaign that I describe in the book, Grant is he's crying. He's not doing it in front of his high command. He's not doing it in a public way. He's going to his own quarters because he knows that the number of killed and wounded that are being produced by this decision is literally filling Arlington National Cemetery. The beginning of Arlington National Cemetery comes from the Union casualties during this particular bloody stretch of the Civil War. It's the highest rate of casualties we've ever had as a country, if you include the Confederate casualties, which I do. So this is also the sort of the burden of Supreme Command and strategic leadership. Like I said, strategy means choices, choices hurt feelings. They hurt people. And when we're talking about Supreme Command, it literally hurts people. And so you can see exactly why this was so difficult.
SPEAKER_01It is horribly difficult in any strategic choice, including and most especially what you mentioned. One of the things I wonder, Matt, is there's a need for conviction at a certain point when you go through that funnel, the strategic leader owns the decision. However, there has to be involvement and input of others in a way that contributes to that. How did you see these three generals balancing that?
SPEAKER_02No human being exercises strategic leadership in isolation. There is no such thing as the solo genius operating independently. Even a guy like Elon Musk, who is running six companies simultaneously, everybody understands he's not really running those companies on a daily basis. He's got some really talented subordinates. So it's the same way with all of these individuals. I like to think of the difference between war and warfare. There are some parts to war and strategic leadership that are ever present, that are timeless, no matter what period of time you're in. Kind of like every conflict that humans have had since one ape hit another ape, slapped another ape. We've put helmets on. We've worn helmets since for thousands of years because we know that it's important to protect our thinking machine. At the same time, it's always changing. And that's the warfare part of it. Warfare, the impediments of strategic leadership are always changing. So General Washington would host councils of war. And we have records of these informal gatherings. He would bring together his senior leadership for big decisions and then voice, listen to the opinions that they voiced. A guy like Ulysses S. Grant was even more informal. He would write dispatches to trusted friends and advisors like General William T. Sherman, William Tecumseh Sherman. And then General Eisenhower had a staff that would actually look a lot like what major corporations look still even echo and mimic today. Again, most of modern business is built on this military foundation, how it is that we're going to win in a competitive endeavor. And they took information in and they bounced ideas out in different ways. But again, it comes back to this balance, like this humble confidence that they all had to be able to listen to all these different ideas, to be open to them for a period of time, and then to choose a course of action and stick with it, right? To make a decision and stick with it. And that's even against withering criticisms. General Eisenhower had nuclear disagreements with Winston Churchill about the way the end of the war should be fought. And I document a few of those cases when I'm telling the story towards the last third of the book. So much so that Eisenhower, a couple of months before D-Day, said, I have made this decision. If it does not go my way, I resign. And Franklin Delano Roosevelt backed him up. The combined chiefs backed him up, and Prime Minister Churchill, the British High Command backed off. I do see those same echoes today. When a CEO makes a particular decision for a particular course of action, sometimes there's going to be investors, sometimes there's going to be outside opinions that just don't agree, but that's why someone has earned that title.
SPEAKER_01That's where the value of judgment that you keep referencing comes into play. Now, the other thing that I saw, Matt, they have in common that you also highlight is their deep understanding of people. And I wonder in what way did their understanding of people impact their strategic decision making?
SPEAKER_02Yeah, I think that with a guy like Eisenhower, for example, when you look at the sum total of his high command, the staff that he was working with, this was in a day and an age where it still took quite a bit of time to travel and they didn't have push-button instant communication like we do. And he had to work on a staff and with allies from all across the English-speaking world and beyond. They also had to, for example, incorporate the ideas and the sentiments from the free French forces that had fled France after the fall and the Vichy government took over. With a guy like George Washington took command of an ad hoc pickup fighting force. And he literally would have to go to different state governors to ask them for troops. And so he would have to bank, borrow, and steal, just like sometimes I can imagine strategic leaders be they in education or the clergy, the business community, or in politics, you don't always get the resources that you want from the get-go. So you have to work with, with and through a system of other people and get their buy-in, get their endorsement, get their support, win it, persuade them. There's this sort of simple notion about wearing a uniform and stars that says that people just snap to and do whatever you want when you want. And that's not definitely not always the case. One of the things that General Ulysses S. Grant was proudest of during the U.S. Civil War was that he never went back to Lincoln and asked for more troops. He recognized that the resources he had, the war effort was stretched thin as it could be. And he said, I will fight with what I have. I think there's something to working within the system of constraints that you have. I think there's a book out right now, David Epstein, Inside the Box, that the constraints you live with can actually be freeing in many different ways. So I think really highly of strategic leaders that do that. And I think we have three examples of folks that did that in this book.
SPEAKER_01Now, one of the things I wonder, Matt, is as we go into this world of AI, where I'm sure you've played around with different AIs, character AI, where you can, in essence, have your board of advisors, you can have George Washington and Ulysses Grant and Eisenhower give you their best judgment on what you should do or shouldn't do. I wonder how you see that impacting the kind of judgment it takes for strategic leadership moving forward when we have access to quote unquote the judgment and insights of any of these characters.
SPEAKER_02I think that AI is an exceptional tool for thinking, for bouncing ideas off of, and it can expand, it can amplify intelligence. That, like to me, that's the way that it can and should and must be used. Where I think that it has a limitation is that it doesn't come with a heartbeat. It doesn't come with a gut. And I think that when we're talking about strategic leadership, again, we need strategic leadership when the competition is close run. It's not the Yankees and the Little League, and the stakes are high. So what happens, the outcome matters, right? And I think when we have those kinds of high consequence judgments that need to be made, they need to become attached to a heartbeat. Like I know that strategic leadership extends far beyond a battlefield. We need it in our boardrooms, we need it in our dugouts, we need it on sports fields, we need it in our principals and our teachers that are guiding the future of our education. When the consequence, or in medicine, for example, I don't think when the consequences are so high, we can give this all the way over to the machines, even if the machines provide us with a really powerful amplification and an ability to see around corners that I don't think we've had before.
SPEAKER_01So it is important for us to wrestle with these ideas, to understand them, to own them, and to then develop our own judgment as a result.
SPEAKER_02Yeah, I can't emphasize enough. General Brant said this: no two wars are alike. No two competitions are alike. Every competition that we step our foot, it's like a river. You can never step into the same river twice, right? You can never step into two competitions that are the exact same. And so that's where I think human creativity and adaptability really matter. I really believe firmly there is no strategic silver bullet. But I think if we look hard enough, and I think we find it in the traces of these Supreme Commanders thinking, there is some strategic buckshot. And we can learn to pick that up and use it, put it in and fire it for ourselves. 100%. I do find that just thinking through some of these things can be of great value. Any kind of strategic leader, I think, is going to benefit from, I called it in the book, getting under Napoleon's hat, crawling into Napoleon's brain for a moment, and trying to see the world the way that he did. And I think we're the better for it the more that we do things like that.
SPEAKER_01And with beautiful storytelling, it becomes more pleasant doing that as well. And you do that with the book, Matt. So for the audience, both to follow your work and your book, where would you send them to?
SPEAKER_02It's as simple as go to who winswars.com. Who winswars.com. The book is distributed by Simon and Schuster and it's published by Matt Holt Books. And then if you go to whowinswars.com, you'll also get to my author website, that kind of thing. And I'd very much look forward to bumping into people and hearing feedback on the book.
SPEAKER_01Appreciate the conversation, the magnificent storytelling in the book and in the episode as well. Who wins Wars Lessons in Leadership, Power, and Supreme Command from Washington, Grant, and Eisenhower. Thank you so much, Matt Kavanaugh.
SPEAKER_02This is fantastic. Thank you so much. I really appreciate the time and I look forward to listening some more.
SPEAKER_00You have been listening to Partnering Leadership with your host, Mahan Tavakoli. If you enjoyed this episode, please leave a rating and review of the podcast on your favorite podcasting app and forward the conversation to a friend or colleague so you can help more people discover their purpose, grow professionally with meaning, and have a greater impact. For additional leadership insights and bonus content, visit us at partneringleadership.com.
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