Full Transcript for 473 Strategy Means Choice: What Washington, Grant, and Eisenhower Teach Us About Leadership with Matt Cavanaugh

still high. 00:05:33.279 --> 00:05:36.800 You can still see what a difference a strategic leader can make. 00:05:36.959 --> 00:05:39.360 That was the starter's pistol for this book. 00:05:39.600 --> 00:05:41.920 What makes a great general great? 00:05:42.160 --> 00:05:43.120 And why? 00:05:43.600 --> 00:05:44.800 How does it work? 00:05:45.040 --> 00:05:53.120 And so for me, launched this longer than a decade period of very serious and sustained study of strategic leadership. 00:05:53.600 --> 00:06:00.480 You spent about 10 years studying these generals as well as the wars. 00:06:00.639 --> 00:06:05.199 Before we get to that, I'd want to go a little deeper into General McMaster. 00:06:05.600 --> 00:06:12.560 He eventually became General McMaster, but he was very candid with people around him. 00:06:12.879 --> 00:06:19.920 And as a result of that, even though he was as strategic as you mentioned, he wasn't promoted. 00:06:20.720 --> 00:06:35.439 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. 00:06:35.920 --> 00:06:36.319 Yeah. 00:06:37.040 --> 00:06:43.759 When you get down to it, strategy means choice and choices hurt feelings. 00:06:44.079 --> 00:06:46.800 And he made decisions that ruffled feathers. 00:06:47.199 --> 00:06:50.959 Matt, I have to stop you just to underline, I love that. 00:06:51.680 --> 00:06:56.240 Strategy means choice, and choices hurt feelings. 00:06:56.399 --> 00:06:56.879 Yes. 00:06:57.120 --> 00:07:10.240 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. 00:07:10.720 --> 00:07:11.120 That's right. 00:07:11.279 --> 00:07:18.160 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. 00:07:18.399 --> 00:07:21.759 A strategic leader is like a funnel. 00:07:21.920 --> 00:07:31.040 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. 00:07:32.319 --> 00:07:42.800 What we want from our strategic leaders is superior judgment, better decisions, not good, bad, superior or inferior. 00:07:43.199 --> 00:07:50.639 And the best of us that are the best at that process have this sense of two things. 00:07:50.800 --> 00:07:58.240 And one is like a sense of grit to make a decision and stick to it, even when it hurts. 00:07:58.480 --> 00:08:01.360 And then the other part of it is a sense of empathy, right? 00:08:01.519 --> 00:08:08.079 Understanding that we live in a world of human beings, and those human beings have feelings and we need to navigate that. 00:08:08.160 --> 00:08:14.720 And that sense of emotional intelligence isn't just good for keeping our side together. 00:08:14.879 --> 00:08:20.879 It's

good for understanding your adversary and understanding the environment that you're trying to navigate. 00:08:21.040 --> 00:08:29.120 And so I think a guy like General McMaster saw the bigger picture, saw all these different options and ideas. 00:08:29.600 --> 00:08:30.639 He picked one. 00:08:30.879 --> 00:08:41.840 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. 00:08:41.919 --> 00:08:47.919 And it took extreme intervention for him to earn his ascension to his first general star. 00:08:48.000 --> 00:08:48.879 And he earned that. 00:08:49.440 --> 00:08:50.799 He really did very much. 00:08:51.120 --> 00:08:55.840 And the preface to the book is titled, Not All Generals Are Created Alike. 00:08:56.000 --> 00:08:59.440 And it's also true, not all strategic leaders are created alike, right? 00:08:59.679 --> 00:09:02.159 Strategic leaders are like human beings. 00:09:02.639 --> 00:09:09.200 Most of them are average, some of them are terrible or borderline insane. 00:09:09.360 --> 00:09:15.759 And then there's a small class of them that are the peak that we want to grow up to be someday. 00:09:15.919 --> 00:09:18.320 And those are the ones that I'm writing about in this book. 00:09:18.559 --> 00:09:19.360 I love that. 00:09:19.440 --> 00:09:24.879 And I also love the fact that you emphasize the importance of superior judgment. 00:09:25.120 --> 00:09:43.360 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. 00:09:43.519 --> 00:09:56.639 And AJ talks about how AI reduces the cost of prediction to near zero, that increases the value of human judgment drastically. 00:09:57.039 --> 00:10:02.559 So the fact that judgment will play a bigger role in our future than we expect. 00:10:02.720 --> 00:10:08.320 So now you have mentioned a few times the importance of superior judgment. 00:10:08.639 --> 00:10:20.320 Based on your study, is this something that can be developed, or did these generals have superior judgments? 00:10:20.639 --> 00:10:21.600 Not from birth. 00:10:21.840 --> 00:10:22.559 Not from birth. 00:10:22.720 --> 00:10:30.240 The three supreme commanders and strategic leaders that I'm taking a look at are George Washington, Ulysses S. 00:10:30.480 --> 00:10:33.360 Grant, and Dwight David Eisenhower. 00:10:33.600 --> 00:10:39.600 And what I'm doing is I am balancing them against their principal opponents. 00:10:39.919 --> 00:10:43.279 So I'm not just looking at them in isolation. 00:10:43.440 --> 00:10:48.399 I'm looking at them in the competition they found themselves in. 00:10:48.799 --> 00:10:54.320 And what you find is all three of them, earlier in their lives, they're like the rest of us. 00:10:54.480 --> 00:10:55.840 They made bad decisions. 00:10:56.000 --> 00:10:56.720 They did. 00:10:57.120 --> 00:11:00.240 And they went through a process of learning. 00:11:00.480 --> 00:11:02.240 George Washington had stumbles. 00:11:02.480 --> 00:11:12.080 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. 00:11:12.399 --> 00:11:14.879 Let me just emphasize that for a moment. 00:11:15.200 --> 00:11:24.480 In June and July of 1776, George Washington had about 16,000 troops spread out over the New York City area. 00:11:24.639 --> 00:11:26.879 Well, we know is New York City today. 00:11:27.360 --> 00:11:38.879 The British invasion force that arrived off New York Harbor was over 42,000 troops, over 400 ships. 00:11:39.120 --> 00:11:47.519 And in today's population figures, that would be like an invasion force of 6 million arriving off the coast of New York. 00:11:47.919 --> 00:12:07.600 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. 00:12:07.840 --> 00:12:11.200 And the American Revolution survives. 00:12:11.360 --> 00:12:15.279 Truly, if America was ever an infant in a crib, this was the moment. 00:12:15.440 --> 00:12:19.519 This was when Thomas Paine wrote the line, these are the times that try men's souls. 00:12:19.600 --> 00:12:21.200 He was with Washington's army. 00:12:21.440 --> 00:12:26.720 And Washington's superior judgment is what kept the American idea alive. 00:12:27.200 --> 00:12:42.080 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. 00:12:42.480 --> 00:12:48.559 And General Eisenhower was a lieutenant colonel when the war began. 00:12:48.799 --> 00:12:56.960 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. 00:12:57.279 --> 00:13:02.559 And he's commanding the largest invasion force that humanity has ever put together. 00:13:03.840 --> 00:13:23.200 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. 00:13:23.440 --> 00:13:28.720 But there are some little breadcrumbs we can follow, right? 00:13:28.960 --> 00:13:31.759 Like I mentioned earlier in our conversation. 00:13:33.200 --> 00:13:44.320 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. 00:13:44.559 --> 00:13:49.039 Another one is how well, what is their emotional intelligence like? 00:13:49.200 --> 00:13:51.519 How well do they relate to other people? 00:13:52.000 --> 00:14:05.679 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. 00:14:05.919 --> 00:14:08.399 That takes lots of people, right? 00:14:08.559 --> 00:14:10.080 It's really difficult to do. 00:14:10.240 --> 00:14:18.159 And if you don't understand people and connect with people at a gut level, you're not going to succeed at it. 00:14:18.399 --> 00:14:22.480 And then when you have to make a hard call, do you make the hard call? 00:14:22.720 --> 00:14:27.840 And some of these commanders, some of these gentlemen, they made the hardest calls you can possibly imagine. 00:14:28.080 --> 00:14:31.600 And it was gut-wrenching for them, truly gut-wrenching. 00:14:32.159 --> 00:14:35.759 So I would love to understand them a little bit better, Matt. 00:14:35.919 --> 00:14:53.440 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. 00:14:54.399 --> 00:14:55.679 And resulting. 00:14:56.159 --> 00:15:03.919 Is it that these are three generals that won for a bunch of different reasons? 00:15:04.000 --> 00:15:04.320 Yep. 00:15:04.480 --> 00:15:10.000 And therefore we go back and study them and say, aha, this is what contributed to success. 00:15:10.320 --> 00:15:11.759 You're asking a wonderful question. 00:15:12.080 --> 00:15:15.840 Is it that they actually contributed to that success? 00:15:16.240 --> 00:15:16.639 That's right. 00:15:16.799 --> 00:15:26.799 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. 00:15:27.039 --> 00:15:39.200 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. 00:15:39.279 --> 00:15:42.080 We know that this particular player is going to win. 00:15:42.399 --> 00:15:44.879 This straw is the one that broke the camel's back. 00:15:45.120 --> 00:15:51.759 We obviously can't run experiments when it comes to military wars like this. 00:15:52.000 --> 00:16:00.080 But what we can do is we can zoom in on a moment where the outcome was still in doubt, right? 00:16:00.399 --> 00:16:05.519 A moment where the war or competition could have gone either way. 00:16:05.759 --> 00:16:13.360 And what we're doing in this book in particular is I'm taking about a one-year period of time. 00:16:13.759 --> 00:16:19.360 And the reason that I take that long period of time is that it eliminates luck from the equation. 00:16:19.679 --> 00:16:28.399 Luck can turn a particular moment or a day, but it can't explain a campaign or a career, right? 00:16:28.879 --> 00:16:44.320 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. 00:16:44.480 --> 00:16:46.399 So I'll give you an example. 00:16:46.720 --> 00:16:54.320 Most folks are familiar with the American invasion of Normandy, D-Day, so to speak. 00:16:54.480 --> 00:17:05.119 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? 00:17:06.480 --> 00:17:15.039 What most people miss is that Eisenhower didn't just make one decision and say, yes, let's go today. 00:17:15.839 --> 00:17:21.119 There were a number of decisions surrounding the entirety of the invasion. 00:17:21.359 --> 00:17:29.920 So, for example, many people know that the United States and the Allies made airborne drops on D-Day. 00:17:30.240 --> 00:17:39.039 So there were two American airborne divisions and then a combined Allied division that dropped right behind the German defenders on D-Day. 00:17:39.279 --> 00:17:45.359 The idea being that you basically try to get the defenders to turn around instead of facing the beach, right? 00:17:45.519 --> 00:17:48.000 So they're worried about two different sides. 00:17:48.559 --> 00:18:06.720 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. 00:18:06.799 --> 00:18:08.400 They'll either be killed or wounded. 00:18:08.640 --> 00:18:12.160 So if we do it, we'll just be dropping these guys to slaughter. 00:18:12.799 --> 00:18:24.799 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. 00:18:25.279 --> 00:18:28.240 Because what we're going to do is we're going to leapfrog ahead. 00:18:28.319 --> 00:18:31.519 We're going to do a deep envelopment of the enemy. 00:18:32.720 --> 00:18:41.519 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. 00:18:41.680 --> 00:18:45.599 Those are three different options coming into that funnel, right? 00:18:45.920 --> 00:18:56.960 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. 00:18:57.119 --> 00:19:07.519 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? 00:19:07.680 --> 00:19:10.079 Everybody's looking to me to make this decision. 00:19:10.319 --> 00:19:12.960 Of course, he made the decision. 00:19:13.279 --> 00:19:14.960 They did make the drops. 00:19:15.200 --> 00:19:19.440 Only about 8% were killed or wounded, and it worked, right? 00:19:20.640 --> 00:19:29.279 And actually, his air component commander wrote to him, Sir, I'm so sorry to have added to your

list of concerns. 00:19:29.440 --> 00:19:32.480 I genuinely believe that's the way things would turn out. 00:19:32.799 --> 00:19:39.920 On the other side of the field, Adolf Hitler is deciding how to defend the beach. 00:19:40.720 --> 00:19:45.119 And he has 10 divisions to spend for reserve. 00:19:45.920 --> 00:19:51.440 Erwin Rommel wants all 10 of those divisions placed right on the beach. 00:19:51.920 --> 00:19:57.920 Because by his experience, that's the best place to put his mobile reserve. 00:19:58.079 --> 00:20:08.240 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. 00:20:08.960 --> 00:20:12.240 Hitler decides to split the baby into three. 00:20:12.559 --> 00:20:16.160 He takes three divisions and places them far forward, right on the beach. 00:20:16.319 --> 00:20:23.519 Three divisions puts them in the middle, and then hold four divisions in reserve for only his release authority. 00:20:24.079 --> 00:20:27.440 I'm this is just one case that I'm trying to draw out. 00:20:27.759 --> 00:20:41.839 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. 00:20:42.319 --> 00:20:49.759 And we can see in part, not all the way, but in part, why strategic leadership makes a big difference. 00:20:50.400 --> 00:20:53.440 What a beautiful example of it. 00:20:53.599 --> 00:20:56.240 And what a powerful way to describe it, Matt. 00:20:56.400 --> 00:21:00.799 I was mesmerized, just listening to you go through the example. 00:21:00.960 --> 00:21:16.400 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. 00:21:16.480 --> 00:21:20.319 And now let's say focusing on judgment as well. 00:21:20.720 --> 00:21:27.519 I still wonder in what ways can that be developed? 00:21:28.000 --> 00:21:36.079 Are there patterns you saw in these experiences that tells you this can be worked on and developed? 00:21:36.240 --> 00:21:37.519 I know they developed it. 00:21:37.759 --> 00:21:38.960 Can we develop it? 00:21:39.279 --> 00:21:39.759 100%. 00:21:40.160 --> 00:21:43.680 So I think there's a cycle in strategic leadership. 00:21:43.920 --> 00:21:46.880 There's like a challenge that emerges, right? 00:21:47.039 --> 00:21:49.440 So you have a challenge that emerges. 00:21:49.680 --> 00:21:52.720 There's a choice that has to be made. 00:21:53.200 --> 00:21:54.799 There's some clash. 00:21:54.960 --> 00:22:01.519 And strategy doesn't matter if you're the New York Yankees and you're facing A little league team. 00:22:01.599 --> 00:22:03.279 It's not a big deal, right? 00:22:03.599 --> 00:22:10.079 Your natural imbalance in talent is going to make all the difference. 00:22:10.319 -->

00:22:20.400 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. 00:22:20.640 --> 00:22:24.799 So there's a clash and then there's consequences that result from that. 00:22:25.039 --> 00:22:36.079 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. 00:22:36.240 --> 00:22:39.119 We can see the artifacts of their thinking. 00:22:39.279 --> 00:22:48.160 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. 00:22:48.319 --> 00:22:53.599 And one of those is all of them had political instincts, emotional intelligence. 00:22:53.759 --> 00:22:56.400 They really did connect well with others. 00:22:56.640 --> 00:22:59.519 They had the skills to persuade others. 00:22:59.759 --> 00:23:14.079 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. 00:23:14.319 --> 00:23:23.279 Another one was we focus on degrees and we focus on things that you hang on the wall. 00:23:23.599 --> 00:23:28.079 But all of these were lifelong learners of the first order. 00:23:28.319 --> 00:23:35.920 Washington had this massive library that he kept at Mount Vernon, and he was interested in everything. 00:23:36.079 --> 00:23:38.559 You name it, plants, animals. 00:23:38.960 --> 00:23:41.519 He had books about military strategy. 00:23:41.680 --> 00:23:43.440 He had books about religion. 00:23:43.759 --> 00:23:45.599 He had lots of fiction. 00:23:45.920 --> 00:23:52.559 Grant, the saint, was a lifelong learner and reader, and the same for Eisenhower. 00:23:52.640 --> 00:24:03.599 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. 00:24:03.839 --> 00:24:06.400 They all had childhood challenges. 00:24:06.559 --> 00:24:14.720 They came, all three of them came from what you would describe as not terribly wonderful home environments from when they were growing up. 00:24:14.880 --> 00:24:18.079 And then lastly, they were pretty young. 00:24:18.319 --> 00:24:20.960 They were all in their 40s or early 50s. 00:24:21.359 --> 00:24:28.880 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. 00:24:29.119 --> 00:24:39.440 Now, 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. 00:24:39.680 --> 00:24:45.519 It's one of those things that sometimes people don't really reflect on and recognize with respect to military. 00:24:45.680 --> 00:24:55.519 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. 00:24:55.759 --> 00:25:14.960 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. 00:25:15.279 --> 00:25:23.519 So 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. 00:25:23.599 --> 00:25:33.039 It's almost like in nature, an eagle or many hawks that fly have this visual ability to have almost picture in picture. 00:25:33.200 --> 00:25:41.519 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. 00:25:41.759 --> 00:25:52.799 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. 00:25:52.960 --> 00:26:02.480 And for these Supreme Commanders, it's battlefield results and strategic awareness of how they stand in relation to their competitor. 00:26:02.720 --> 00:26:20.559 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. 00:26:20.720 --> 00:26:24.559 And there's really striking examples of that. 00:26:24.640 --> 00:26:27.279 So I mentioned Washington in New York, right? 00:26:27.519 --> 00:26:31.279 He's completely overwhelmed by this British onslaught. 00:26:31.440 --> 00:26:37.759 That invasion force that the British sent was the largest invasion force the British Empire had ever sent anywhere. 00:26:38.000 --> 00:26:54.880 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. 00:26:55.119 --> 00:27:01.440 But the Continental Congress had expressed to Washington that they wanted him to hold New York, right? 00:27:01.680 --> 00:27:10.160 So he's got this tension between military necessity and what politics is driving him to need to do. 00:27:10.880 --> 00:27:24.160 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. 00:27:24.400 --> 00:27:37.279 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. 00:27:37.680 --> 00:27:49.599 Like another example is that General Grant is fighting while his political partner, President Abraham Lincoln, his boss, is campaigning for the presidency. 00:27:49.839 --> 00:27:53.759 And

he knows that if Lincoln loses the election, the war is over. 00:27:54.799 --> 00:27:57.839 Maybe not in a military sense, but in a political sense. 00:27:58.079 --> 00:28:01.359 So he's also got to navigate those tensions as well. 00:28:01.519 --> 00:28:15.279 So those tensions that exist in every boardroom in America or around the world exist in battlefields and with amongst democracies as well. 00:28:15.519 --> 00:28:29.119 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. 00:28:29.680 --> 00:28:31.359 And that's a dangerous thing. 00:28:31.519 --> 00:28:34.559 That's a dangerous thing because there is no feedback loop. 00:28:34.799 --> 00:28:36.240 There is no feedback loop. 00:28:36.319 --> 00:28:40.400 And the feedback loop on a battlefield is a really painful one. 00:28:40.799 --> 00:28:40.960 Yeah. 00:28:41.119 --> 00:28:53.920 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. 00:28:54.240 --> 00:28:55.039 I definitely agree. 00:28:55.119 --> 00:29:14.720 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. 00:29:14.960 --> 00:29:26.720 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. 00:29:26.960 --> 00:29:35.920 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. 00:29:36.160 --> 00:29:42.079 This is the difference between tactics and strategy, very much that lesson to me is really important. 00:29:42.720 --> 00:29:54.079 Another 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. 00:29:54.319 --> 00:30:05.680 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. 00:30:05.839 --> 00:30:08.480 We'd love to get your thoughts on that as well, Matt. 00:30:08.720 --> 00:30:13.279 This is the thing that Sun Tzu was getting at attack the enemy's strategy. 00:30:13.440 --> 00:30:22.880 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. 00:30:23.200 --> 00:30:38.400 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. 00:30:38.799 --> 00:30:45.440 And with Washington, he was looking to exhaust an adversary. 00:30:59.440 --> 00:31:00.960 They had more of them. 00:31:01.200 --> 00:31:05.039 On some level, they had so many advantages. 00:31:05.279 --> 00:31:24.000 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. 00:31:24.319 --> 00:31:37.279 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. 00:31:37.440 --> 00:31:40.400 Like I said, he had lost battle after battle after battle. 00:31:40.559 --> 00:31:55.279 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. 00:31:55.359 --> 00:32:02.160 And Grant made the decision to say, no, we will make this a continuous fight all the way till the end. 00:32:02.400 --> 00:32:06.880 And Grant didn't do that with great happiness in his heart. 00:32:07.119 --> 00:32:17.839 There are several recorded instances in the historical record where during this campaign that I describe in the book, Grant is he's crying. 00:32:18.000 --> 00:32:21.200 He's not doing it in front of his high command. 00:32:21.279 --> 00:32:22.880 He's not doing it in a public way. 00:32:22.960 --> 00:32:38.079 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. 00:32:38.319 --> 00:32:46.640 The beginning of Arlington National Cemetery comes from the Union casualties during this particular bloody stretch of the Civil War. 00:32:46.799 --> 00:32:53.680 It's the highest rate of casualties we've ever had as a country, if you include the Confederate casualties, which I do. 00:32:54.000 --> 00:32:59.359 So this is also the sort of the burden of Supreme Command and strategic leadership. 00:32:59.519 --> 00:33:03.920 Like I said, strategy means choices, choices hurt feelings. 00:33:04.000 --> 00:33:04.880 They hurt people. 00:33:05.039 --> 00:33:08.559 And when we're talking about Supreme Command, it literally hurts people. 00:33:08.720 --> 00:33:12.960 And so you can see exactly why this was so difficult. 00:33:13.279 --> 00:33:19.200 It is horribly difficult in any strategic choice, including and most especially what you mentioned. 00:33:19.359 --> 00:33:31.359 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. 00:33:32.880 --> 00:33:41.119 However, there has to be involvement and input of others in a way that contributes to that. 00:33:41.759 --> 00:33:47.519 How did you see

these three generals balancing that? 00:33:48.319 --> 00:33:53.039 No human being exercises strategic leadership in isolation. 00:33:53.200 --> 00:33:58.160 There is no such thing as the solo genius operating independently. 00:33:58.319 --> 00:34:08.559 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. 00:34:08.800 --> 00:34:11.119 He's got some really talented subordinates. 00:34:11.280 --> 00:34:14.159 So it's the same way with all of these individuals. 00:34:14.400 --> 00:34:17.440 I like to think of the difference between war and warfare. 00:34:17.599 --> 00:34:25.760 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. 00:34:25.920 --> 00:34:31.840 Kind of like every conflict that humans have had since one ape hit another ape, slapped another ape. 00:34:31.920 --> 00:34:32.880 We've put helmets on. 00:34:32.960 --> 00:34:39.119 We've worn helmets since for thousands of years because we know that it's important to protect our thinking machine. 00:34:39.360 --> 00:34:41.519 At the same time, it's always changing. 00:34:41.599 --> 00:34:43.360 And that's the warfare part of it. 00:34:43.599 --> 00:34:47.599 Warfare, the impediments of strategic leadership are always changing. 00:34:47.760 --> 00:34:52.079 So General Washington would host councils of war. 00:34:52.320 --> 00:34:55.440 And we have records of these informal gatherings. 00:34:55.679 --> 00:35:02.719 He would bring together his senior leadership for big decisions and then voice, listen to the opinions that they voiced. 00:35:02.960 --> 00:35:04.400 A guy like Ulysses S. 00:35:04.480 --> 00:35:06.239 Grant was even more informal. 00:35:06.639 --> 00:35:11.840 He would write dispatches to trusted friends and advisors like General William T. 00:35:12.000 --> 00:35:14.159 Sherman, William Tecumseh Sherman. 00:35:14.320 --> 00:35:24.320 And then General Eisenhower had a staff that would actually look a lot like what major corporations look still even echo and mimic today. 00:35:24.480 --> 00:35:32.480 Again, most of modern business is built on this military foundation, how it is that we're going to win in a competitive endeavor. 00:35:32.800 --> 00:35:38.719 And they took information in and they bounced ideas out in different ways. 00:35:39.039 --> 00:35:57.119 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? 00:35:57.280 --> 00:35:59.199 To make a decision and stick with it. 00:35:59.280 --> 00:36:02.880 And that's even against withering criticisms. 00:36:03.039 --> 00:36:14.239 General Eisenhower had nuclear disagreements with Winston Churchill about the way the end of the war should be fought. 00:36:14.480 --> 00:36:20.719 And I document a few of those cases when I'm telling the story towards the last third of the book. 00:36:20.960 --> 00:36:28.079 So much so that Eisenhower, a couple of months before D-Day, said, I have made this decision. 00:36:28.239 --> 00:36:31.039 If it does not go my way, I resign. 00:36:31.280 --> 00:36:34.239 And Franklin Delano Roosevelt backed him up. 00:36:34.400 --> 00:36:40.239 The combined chiefs backed him up, and Prime Minister Churchill, the British High Command backed off. 00:36:40.559 --> 00:36:43.360 I do see those same echoes today. 00:36:43.679 --> 00:36:59.760 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. 00:37:00.639 --> 00:37:06.000 That's where the value of judgment that you keep referencing comes into play. 00:37:06.159 --> 00:37:14.559 Now, the other thing that I saw, Matt, they have in common that you also highlight is their deep understanding of people. 00:37:15.039 --> 00:37:22.159 And I wonder in what way did their understanding of people impact their strategic decision making? 00:37:22.719 --> 00:37:45.199 Yeah, 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. 00:37:45.519 --> 00:37:54.639 And he had to work on a staff and with allies from all across the English-speaking world and beyond. 00:37:54.880 --> 00:38:09.519 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. 00:38:09.840 --> 00:38:17.039 With a guy like George Washington took command of an ad hoc pickup fighting force. 00:38:17.280 --> 00:38:23.840 And he literally would have to go to different state governors to ask them for troops. 00:38:24.079 --> 00:38:40.800 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. 00:38:40.960 --> 00:38:50.880 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. 00:38:51.119 --> 00:39:00.400 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. 00:39:00.559 --> 00:39:03.519 And that's not definitely not always the case. 00:39:03.840 --> 00:39:06.639 One of the things that General Ulysses S. 00:39:06.800 --> 00:39:09.760 Grant was proudest of during the U.S. 00:39:09.840 --> 00:39:15.760 Civil War

was that he never went back to Lincoln and asked for more troops. 00:39:16.079 --> 00:39:23.519 He recognized that the resources he had, the war effort was stretched thin as it could be. 00:39:23.760 --> 00:39:26.320 And he said, I will fight with what I have. 00:39:26.559 --> 00:39:31.840 I think there's something to working within the system of constraints that you have. 00:39:32.000 --> 00:39:40.559 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. 00:39:40.719 --> 00:39:43.679 So I think really highly of strategic leaders that do that. 00:39:43.760 --> 00:39:46.559 And I think we have three examples of folks that did that in this book. 00:39:46.880 --> 00:40:12.079 Now, 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. 00:40:12.400 --> 00:40:27.119 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. 00:40:27.599 --> 00:40:38.239 I think that AI is an exceptional tool for thinking, for bouncing ideas off of, and it can expand, it can amplify intelligence. 00:40:38.400 --> 00:40:42.960 That, like to me, that's the way that it can and should and must be used. 00:40:43.280 --> 00:40:46.719 Where I think that it has a limitation is that it doesn't come with a heartbeat. 00:40:46.800 --> 00:40:47.920 It doesn't come with a gut. 00:40:48.000 --> 00:40:58.639 And I think that when we're talking about strategic leadership, again, we need strategic leadership when the competition is close run. 00:40:59.199 --> 00:41:03.199 It's not the Yankees and the Little League, and the stakes are high. 00:41:03.360 --> 00:41:06.480 So what happens, the outcome matters, right? 00:41:06.960 --> 00:41:15.679 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. 00:41:15.920 --> 00:41:21.280 Like I know that strategic leadership extends far beyond a battlefield. 00:41:21.440 --> 00:41:33.119 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. 00:41:33.360 --> 00:41:51.599 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. 00:41:52.159 --> 00:42:00.880 So 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. 00:42:01.199 --> 00:42:03.039 Yeah, I can't emphasize enough. 00:42:03.280 --> 00:42:06.639 General Brant said this: no two wars are alike. 00:42:06.800 --> 00:42:08.400 No two competitions are alike. 00:42:08.559 --> 00:42:11.360 Every competition that we step our foot, it's like a river. 00:42:11.440 --> 00:42:14.320 You can never step into the same river twice, right? 00:42:14.480 --> 00:42:17.840 You can never step into two competitions that are the exact same. 00:42:18.000 --> 00:42:23.920 And so that's where I think human creativity and adaptability really matter. 00:42:24.159 --> 00:42:28.239 I really believe firmly there is no strategic silver bullet. 00:42:28.400 --> 00:42:38.079 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. 00:42:38.159 --> 00:42:42.159 And we can learn to pick that up and use it, put it in and fire it for ourselves. 00:42:42.400 --> 00:42:42.719 100%. 00:42:43.199 --> 00:42:49.039 I do find that just thinking through some of these things can be of great value. 00:42:49.360 --> 00:43:02.159 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. 00:43:02.480 --> 00:43:06.960 And I think we're the better for it the more that we do things like that. 00:43:07.360 --> 00:43:11.440 And with beautiful storytelling, it becomes more pleasant doing that as well. 00:43:11.599 --> 00:43:13.840 And you do that with the book, Matt. 00:43:14.000 --> 00:43:19.199 So for the audience, both to follow your work and your book, where would you send them to? 00:43:19.519 --> 00:43:22.800 It's as simple as go to who winswars.com. 00:43:23.039 --> 00:43:24.639 Who winswars.com. 00:43:24.800 --> 00:43:28.960 The book is distributed by Simon and Schuster and it's published by Matt Holt Books. 00:43:29.280 --> 00:43:35.599 And then if you go to whowinswars.com, you'll also get to my author website, that kind of thing. 00:43:35.760 --> 00:43:39.840 And I'd very much look forward to bumping into people and hearing feedback on the book. 00:43:40.320 --> 00:43:46.239 Appreciate the conversation, the magnificent storytelling in the book and in the episode as well. 00:43:46.559 --> 00:43:53.519 Who wins Wars Lessons in Leadership, Power, and Supreme Command from Washington, Grant, and Eisenhower. 00:43:53.679 --> 00:43:55.599 Thank you so much, Matt Kavanaugh. 00:43:56.239 --> 00:43:57.119 This is fantastic. 00:43:57.280 --> 00:43:58.159 Thank you so much. 00:43:58.320 --> 00:44:01.119 I really appreciate the time and I look forward to listening some more. 00:44:02.639 --> 00:44:06.800 You have been listening to Partnering Leadership with your host, Mahan Tavakoli. 00:44:07.440 --> 00:44:23.039 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. 00:44:23.280 --> 00:44:29.360 For additional leadership insights and bonus content, visit us at partneringleadership.com.