Admiral Sandy Winnefeld — Sailing Upwind: Leadership and Risk from TopGun to the Situation Room

Are you thinking about how to grow your business with near and offshore staffing, but you're also wanting to make sure that it's reliable, cost effective and really well done? I think docsa talent is the way to go. Here's why. They don't just fill your jobs. They bring integrity, top talent, and a people first approach that's hard to find. I've known the people at Doxa talent for over 20 years now and I say that you can count on them. I have talent. Talk to Doxatant and you won't be disappointed. Go to doxatant.com Bill G. Again, that's doxatant.com Bill g. One more time. Doxatalent.com Bill G. Check it out today. Oh, I'm excited about this conversation today. We're talking about sailing upwind, sailing into the wind and all the challenges. I'm a sailor, I'm a pilot. All things I love to do and I think are so related to leadership at every level, right? Whether you're leading a couple of dozen people or whether you're leading thousands. And then along the way, we face challenges that are inevitable. That's our conversation today. Very special guest, some of you may already recognize if you're looking at video, if you've seen the title. Retired Admiral Sandy Winifield is up next. Hi again, everybody. My name is Bill Gallagher, scaling coach and host of the Scaling Up Business podcast. We bring our show to you every week, a couple times with some lessons, something to do with growing your company and leveling up your leadership along the way, which is what's so great about this, all our shows and more. Wherever you're getting this now, like subscribe, turn on your notifications, all that kind of thing, or go to scalingcoach.com where you'll find all our back catalog of episodes plus all our workshops, boot camps, things like that that you might want to do to get your company scaling up. Okay, so I'm joined on the east coast now by retired Admiral Sandy Winnefeld. Sandy, welcome to the show.

Well, it's great to be with you, Bill. Been looking forward to it.

I'm so excited to have you on, not just because you're a sailor and a pilot, but like the, the arc of your career is outstanding. So just a couple highlights for people who don't know. Sandy retired as the vice chair of the Joint Chiefs of Staff, but he commanded the Enterprise, norad. He was a top gun, the sixth Fleet. A couple of things along the way. So it's really and you started out in San Diego. I'm originally from Southern California. And you sailed in the beginning, which is I think where the, the title comes from for the, for the book and the focus.

It does indeed. And you know, sailing had such a profound influence on my career. Not only the sort of hands on pieces of operating a boat in current wind and tide and competing against people like you might in a fighter aircraft, but it also taught me that you can actually move a machine against a prevailing force of nature. And I did an awful lot of that in the bureaucracy in the Pentagon. So it was a very apt metaphor for the title of the book.

One of the things that I love to do is do little mini coaching sessions with groups of CEOs or leaders while sailing on the San Francisco Bay where I'm normally based. And San Francisco sailing is very intense for most people. We get very brisk winds on a regular basis and it can look calm on the periphery. There could be sun overhead, but that wind is just blowing it. And then all of a sudden you can be overwhelmed with fog where you can't see anything. And the boat's he. Even if you're in a sizable, like a 50 foot boat or something, you feel something.

Yeah. As shifting wins too. It's not constantly from the same direction because of all the terrain and the buildings and all that. You know, that wind swirls around in San Francisco. I haven't sailed very much up there, but I know it's rough. I've been in there in the bay.

It's intense. I had to teach family to sail once before. We went on an extended family sailing trip in the Mediterranean. So we met in San Diego. I'm like, that's going to be a lot easier than meeting in San Francisco. And you can get a little. It's warmer, the water's warmer. Like everything's a little bit, a little bit easier.

Yeah. Just try to sail a boat from San Diego to San Francisco and you get a real treat. You better be ready for some.

Yeah. Going north against the current is a challenging direction. Sailing south is a lot easier than going back up. Yeah. So that's great. We're going to have you share some stories and, and reflections from the, from your life and, and why don't you start off early on? Top Gun is a fantastic place to start. We all know that. And you were actually at Top Gun when they were shooting the first movie, right?

I was indeed. Everybody's famous for 15 minutes. Right. And so my name appears in the credits along with some other Top Gun Instructors who were in the movie. But yeah, Top Gun was such an amazing experience. I went through my first Tour as an F14 pilot, went through the class during that time, and then miraculously got selected to come back as an instructor. And I'll tell you, never a day went by when those of us who were instructors there didn't, didn't sort of say to each other, like, who did we fool in order to be able to come to this amazing place? And it was, it was where the highest possible standards of excellence in not only flying, but in teaching, both in the air, to keep it safe, to keep it meaningful with these very expensive sorties that we would fly, but also the, the standards we had on the ground for giving a lecture. You know, if I was to give a one hour lecture to the class, I first had to give it to the assembled instructors and endure about a six hour debrief criticizing every single thing that I did. And it's possible to fail that. You know, we call it a murder board. Top Gun invented the term murder board. So it was incredible. And it was also incredible because the inmates ran the asylum. It was all of us young, you know, second tour pilots who were really in charge of it. We had a commander, but he was kind of a, you know, make the, make the trains run on time. But we actually kept the standards up and ran the thing. And then the, the most impactful thing for me from a cultural perspective, which I think is very relevant to businesses, was positive peer pressure. We all knew we were doing well and in the Navy and the community, and, and we just, we didn't compete with each other. We all bucked each other up, held each other to a higher standard. And that was such a refreshing, wonderful environment to be in. Highlight and the movie. Yeah, okay, the movie was there, right?

Well, the movie immortalized and romanticized, right. The fighter pilot lifestyle, in particular, the Navy. I served briefly in the Air Force, and that's a very different culture and environment. And Top Gun and Red Flag are probably pretty different experiences from a lot of standpoints.

Although we, we actually worked very closely with the Air Force fighter weapons school up at Nellis. We were both doing tactics development. There were things that the Air Force fighter weapon school was really good at, and there were things that we were also very good at and we learned from each other and in fact, exchanged pilots. We had, you know, a couple of Air Force exchange pilots at Top Gun while I was there, and they were their best of the best. And it was really, you know, it was a little controversial too. When we got our first pilot, there were some people who were against it. It was like, no, no, no, we're going to benefit from this. And in fact, we did.

Yeah, I think, well, anytime, right? You exchange points of view practices. You think about at both places exchanging with foreign pilots. You know, at Nellis we would see regularly pilots come in from other air forces around the world and they would fly. And you know, you learn tremendous things flying around the Israelis. But, but like everything you're going to learn who fly different environments, different cultures.

That's true, but you're right, there were different, different cultures. I remember one of our Air Force pilots went out on a sortie one time and the canopy came off of his F5 and he came back and landed and he was not going to get out of that airplane until somebody came and thoroughly inspected to make sure he hadn't done anything wrong. And he thought he was toast. And we were like, hey, stuff happens, you know, you're a competent pilot, you know, you have earned your stripes here and you know, get back in the airplane tomorrow. He was shocked. Anyway.

Expected to be career ending, huh?

Yeah.

Or at least limiting.

True.

Well, so the first thing before we move on to the next story or chapter I think is interesting is so in that environment, right, you go from like mastering it at a basic level, like being able to compete and fight in that environment, but then being an instructor where you not only have to provide good adversary, good challenge to the incoming participants in the program, but then you also have to remember, recall and do all that under G load, right? Sustain, sustaining, maintaining situational awareness. Like the whole, like that's intense.

Very perceptive question, Bill. We would go out and, you know, we were responsible for making sure that all the flights were conducted safely in these very aggressive and high tempo environments. And then you're right, you're, you're, you're operating this airplane under high G, you're trying to fly precise airspeed and G, you've got to keep sight of your opponent, you got to manage your weapon system, you got to do all those things and you have to remember, you know, maybe three different fights from a single one hour sortie. And then you've got to come back and make sure that it's debriefed in quality fashion. A three dimensional fight debriefed in two dimensions on a whiteboard. And try to get the teaching points across. And it's not. And then another layer of complexity is maybe early on in the class you're teaching these young pilots how to Fly and fight well, but then you're also having to teach them how to debrief and teach, because that's what they're supposed to go back to their squadrons.

Go back to their squadrons. Yeah.

One of the interesting things about that is these are some pretty high energy, high ego people. And so one of the things we had to learn as top gun instructors and teach to these students is to pull the ego out of the debrief. And one of the reasons why I think our fighter pilots, Navy, Air Force, Marine Corps are the best in the world is because we are brutally hard on ourselves in the debrief, but in a tactful fashion. So we would. Instead of referring to what were you doing at this point in the fight? It was like, what was the F18 thinking? To kind of take the who out of it? And all those little techniques are developed. And I think there's a good lesson in there for leaders everywhere is be really sensitive to your audience and speak to them in respectful terms at the same time you're teaching them. It's a very important, I think, point.

You know, it's interesting. I served under a couple of commanders in my brief time in the Air Force, and I won't name any names, but I can remember one who. He just must have had some deep insecurity or something like that, but he was a drag. And I know that he kind of plateaued out. And I remember this other guy who. Who started as an enlisted guy early on in his life and then progressed up and eventually became general. And the difference in his humanity and humility. They both, you know, were willing to take charge, but one did it from a different place than the other, who did it in service of that servant leadership mindset. Like, I'm here in this role for. For this unit in service of our mission, but I'm not better than you. I'm not dominating.

Oh, you're. You're so right. And, you know, of the many, many characteristics of a good leader, the very first and most important one is character. And I think the components of that character are things like integrity and courage and humility. Genuine humility, not false humility. And so the best leaders I've ever worked for were able to combine the fact that they were. There were very bright people who had, you know, had a mission in mind and wanted to accomplish something, but they managed to do it in exactly the fashion you described with. With humility and care for their people.

It's. It's a. I think it's such a valuable lesson. And I. And I know that I. In my good moments, I have it. Today. I still. I'm endlessly arrogant, for sure, but at least I catch myself in it a lot of the time now. And. And I think early in life, as a younger man, I. I had this, like, real thought that someday I'd, like, have enough classes or training programs, that kind of thing. And then I. I wouldn't have said it in this way then, but, like, I'd cease being human. I'd transcend that, and I'd be some kind of golden being, and I would just be awesome. And then I wouldn't have. I suddenly arrived. And then I remember one day in my mid-30s, and. And I was being coached and trained by someone, and then I watched him go up and demonstrate something for me, and I was like, oh, he's, like, way beyond me. And he just screwed that thing up. And I had this moment that turned out to be so powerful and enduring, and it was like, I'll never be finished. And at first, that was for a half a second, that was depressing. But after that, I was liberated. I'm like, oh, I could just be a student forever for the rest of my life. And that became a deep personal and company value. Never finished. And I think of Jack Lalanne, the old exercise guru who, like, trained until his 80s. Like, that was really inspiring. Like, oh, I could just be a student until I die.

Sure. You know, in the book, I talk about five anchors of leadership, and the first one being leading yourself. And an essential element of leading yourself is lifelong learning. Knowing your stuff. But you never stop learning about your profession. You never stop learning about things that are adjacent or even far from your profession. And most importantly, you never stop learning about leadership. I still learn things every day that I want to. I want to hook onto this, you know, framework that I've got in my mind for. For what you have to do to develop yourself into a good leader. And you're so right. You don't start off with all these things in mind. I mean, I think there are sort of three things you have to do to learn to be a good leader. One is study, and that's maybe reading books about leadership. It may be reading books about leaders or maybe listening to Bill Gallagher's podcast, but one way or the other, you know, study. And then another one is observation, because we've all worked for good and poor leaders. You described that yourself earlier. You had two Air Force guys, one great, one not so great. You learn from them all, and then the last is run to the sound of the guns, man. Anybody gives you a chance to lead something, go for it. Particularly when you're young, because that's when the lessons are kind of free.

Step up, raise your hand, lean in.

Yeah, exactly.

Yeah.

But it goes on forever. You're absolutely right.

So sailing up wind, you can't sail exactly into the wind. You have to sail a little bit off really great boats, sail higher into the wind than not. And you can sail directly downwind, but it's not the best way to sail. So, like, you've got all points of the compass except directly into the wind and probably best not. So sailing into the wind is like dealing with challenges. And of course, wind shift, current shift, things happen. Talk, then share some of the examples. You talked about the challenges commanding an F14 squadron. You talked about with F18s on the Teddy Roosevelt. Like, I don't share some of the sailing against the wind challenges.

Sure. I'll give you an example from when I was a squadron commander. We had come back from a deployment, we were getting ready to start our workup period for the next deployment. So we were sort of lowest on the totem pole. And normally you'd have a decent amount of flying money and, and go off into your training, but this was a very tough year for the federal government. And we were told that for the last three months of the fiscal year, we would have basically no flying money. Yeah, we would have maybe be able to fly one sortie a week. Not every pilot, just the whole squadron, one sortie a week. And I was called by a three star admiral who said, show the pain. Show us the pain. And I said to myself, you know, that's not my job to show pain. First of all, my job is to take whatever little money the taxpayers give me to make the best possible fighter squadron I can. And how is that going to impact the morale of my squadron when I'm walking around? Okay, everybody, this really sucks. Let's show the pain. So we made a decision very right away, basically that we were going to come out of this better than when we went into it. We were going to try to be innovative. We weren't supposed to touch our airplanes because they were worried we were going to cannibalize the parts. But we got special permission to tear them all down and put them all back together. Corrosion control, very important in Navy airplanes. And we did that. We took everybody to the simulator in the middle of the night to make the maximum use of that and really pounded ourselves on the safety side. We visited Nellis, went to the fighter weapons schools museum they have up there, which is quite interesting. A lot of old Russian airplanes and things like that I can talk about now that I couldn't talk about then. And we, we essentially set ourselves a goal at the end of this three month period where we were going to fly every single one of our airplanes within the first week that we got our money back and that we were going to fly a 50 sortie day dropping live weapons. And people told us we were crazy. I said, no, we're going to manage this risk, we're going to set a goal and we're going to achieve it. And we did. And I almost called that admiral back and said, you know, you ought to take money away from people for three months all the time. But I didn't really, didn't really want to do that. But the point was to overcome adversity and to try to turn a negative into a positive. And, and you know, we weren't sailing straight into the wind when we did that, but we were kind of, kind of tacking back and forth there, doing the best we could to push against that problem and actually do our job. Make the best fighter squadron you can.

You know, it's interesting when, when everything's favorable, when the economy's up, when you're in a fresh market space that without a lot of competition, you tend to be weaker in execution, you tend to be sloppier, you tend to introduce inefficiencies, but when pressed with hardship, you have to innovate, you have to get stronger, you have to operate more sharply. And, and so I think that's actually a useful thing to think about. Like the value of the hardship.

Yeah. You know, and Bill and the world is changing so fast. I think we're getting maybe this, everybody's felt this for centuries, but I just feel like the, the things are accelerating and change is happening so fast, you may not have time to get yourself into that very efficient, hard nosed, you know, innovative mode. When the thing happens, you gotta be thinking that all the time. And I think the most successful business leaders I see are constantly, you know, scanning the horizon. You know, there's, there's a goodness to being paranoid about certain things and they're, they're constantly trying to push on their system to do better. And I think that in this world you got to do that.

Yeah. If you're not like thinking about staying sharp and playing to your strengths and developing those before you hit a crisis is real. I was out walking our dog earlier today with my wife and we're talking about some scenarios that we could imagine the next couple of years in different triggering events in the world. And like, well, if that kind of goes then, if my business went like this, then my purpose is and like our mission as a company and my. How I spend my career when I'm committed to, like, oh, well, we could lean into that in that way. So what would we need to do now? Because that could or could not happen. Right. We've got major triggering events going on in both in Asia and in Eastern Europe. Just scare the hell out of me.

And you know, in business we talk about disintermediation or disruption or whatever adjective you want to use or verb in the security context. We're in the same place. And you. I think one of the keys is to be able to imagine what this is going to be like when it really happens, and then to ask yourself, okay, are we, are we making any assumptions about this that we shouldn't be making that are false assumptions? Because that's fatal.

Yes.

And then trying to take, particularly in my former world in the military, a very difficult, both military and congressional and industrial bureaucracy and not only change the means, but also change the ways of operating so that you actually have a chance to prevail in a situation like that. But I do worry about that quite a lot, Bill. I don't know that we are in that place that you're talking about right now as far as those crises go.

Yeah, I mean, I could imagine, you know, I mean, there are the actual, like, geopolitical events, the stuff with Russia, the stuff with China that's developing, but then there's all the ripples of unrest that it can affect banking and commerce and all kinds of things like that. So, you know, who knows?

And, and yeah, just look at what business should be thinking in terms of China. You know, there, there are businesses that actually do business in China. There are businesses that have supply chain coming from China and, you know, ride that pony as long as you can. But you really need to be thinking a couple of things. You know, we would like to kick this can down the road as long as we can, and frankly, so would China. But they have declared. And when a dictator declares that they're going to make something happen, then they generally do. So you need to be ready well in advance, you know, not two weeks, but maybe four to six months to detect that this bad thing is about to happen and then have a campaign plan in place for how you're going to disentangle yourself, whether it's you Know, getting out of your business in China by selling it to somebody in China, or having alternative means of supply, or by maybe giving up a point of margin in order to have a little bit more inventory, whatever you have to do, and then have the discipline to execute it. When you see that change coming, that is what good business leaders do. They look around those corners and make sure that they're well positioned to, to take those things on.

You know, this is a great segue into this next little bit in the elevation of leadership. I, I had a mentor who had a son who served a couple terms under Obama as one of the special assistants. And, and so he gave us a little tour of the West Wing one weekend and we popped in and when it was emptier, his president was away. And so we got to go through the Oval Office and the Cabinet Room and down to the door, the situation room, and, you know, all, all around it. And so that's cool, you know, if you've never done that before. But what was fascinating to me is how he said, look, my job is really just all about managing personalities, psychology, and egos. He's like, so when the opposing party leader from Congress or Senate has their high school friends who want to tour around, we want to show them a good time because we don't want to add any difficulty to the negotiation on the next bill or whatever. We don't want to want to add a personal friend. And if I know this person's got a beef with that person, I'm going to walk them down this corridor, not that corridor, so they don't have to pass each other and have an interaction that I'm like. And, you know, I was thinking it's more about policy and formulating positions. And he's like, no, it's really, it's people.

Yeah. I think when you get into inter branches of government discussions, you have to do that, and in particular with Congress, because they're all, frankly, they all are great patriots, but the only thing that matters more to them than patriotism is their own reelection.

Right.

So I think there is a dynamic there, I will say, under two different administrations where I spend a lot of time in the White House sit room, both the George W. Bush administration and the Barack Obama administration, that once you got into that world, into the sit Room, that first of all, there was nobody that was talking about domestic politics. There was not once a situation where somebody said, hey, if we do this thing with this foreign policy thing, it will help us with the election. I never. That may have gone on outside the sit room, but not in the sit room. And I would also say there's a remarkable similarity between the understanding of the problems we were facing and the solutions to those problems between what you would imagine were completely different philosophies, political philosophies. But when you get in that room and I tell people when you're sitting at the end of that table like you're the president, the world changes. The, the, the rhetoric of the campaign trail, you know, all the yelling and screaming goes away and you now have the best intelligence in the world. You have the best sense of our capabilities and our limitations and you have the, the blood and treasure of the United States on your hands and it completely changes the perspective. It's amazing. And I, I think most, not all, but most of our leaders kind of step up to that.

You know, it's, it's nice to hear that, and I've heard that from others who were in some of those meetings conversations as well, that, that it's not like the just obnoxiousness of some movie character and TV characterizations where they dramatize people as being just nakedly self serving and throwing out all these little political angles when they're dealing with like real lives and, and serious things. It's nice to hear that there are.

People from, from both of those administrations who I can consider my close friends because you know, there's nothing to build a friendship more than, than shared hardships and, and, and crises together. And we always tried to keep a little sense of humor in those meetings, but I had a healthy respect and a lot of people had different positions. You want to talk about landmines, you know, the State Department's going to be from, from Venus and, and you know, Defense Department's going to be from Mars there.

Right.

But always choices, conversations, always respectful discussions and hopefully getting to a mutually agreeable answer. So I was just going to ask.

You a question about that to expand on. So one of the things that our leaders in both our coaching and listening, watching the show will bring up is the challenge of going through the levels of leadership. So I've got a dozen people, I've got a few hundred people, I've got a thousand people, I've got a few thousand people. I, one of our clients right now is going from 1,000 to 2,000 people. One of our clients last year was going over 4,000. And in these inflection points, your leadership style has to change at each point. And you went from just being a pilot to being an instructor to being commander and Then ever larger things and then eventually serving in the White House. What is that progression like or what stories could you share about the evolution of your leadership and the, the people that you saw doing the same kind of thing?

Well, that's an amazing question, and it's also a very complicated answer, to be quite honest with you. But at the most fundamental level, changing from small organizations to larger organizations, you find that you're, you're not only your span of control increases, but your ability to know everybody decreases. Right. So in a small team, you're able to instill culture and look people, right, everybody right in the eye and make sure that culture is getting through and that the tasking is understood and everybody's taken care of and high standards, good care. When you get to leading a million people or whatever, the thing you have to count on is that your subordinate leaders have the same vision that you do. So it's terribly important, I think, especially when you first enter into one of those jobs, is to do a deep dive with those senior leaders, make sure that they understand your cultural views, your, your vision for what the organization's going to do. And so that when you pull out of that, you know, two week, whatever immersion, that you have confidence in them, that they, that, that when they have a tough decision to make, they're going to go, well, what would Gallagher say here? Or what would Winnefeld say here? What would he do? And that, first of all, frees you up to go outside the organization and do your job outside the organization. Organization. But it also means, you know, you can't possibly control everything from, from the center. But at the same time, it's terribly important that that senior leader in a large organization get all the way down to what we call the deck plates in the Navy and sniff around by yourself without an entourage and go talk to people and see how they're doing, see what's frustrating them, see if they've drunk, drank in the culture, because you'll see if it's penetrated down through those layers. And then don't spend a lot of time down there. You got to get the heck out of there fairly quickly. But you have to do this if you're really going to have your cultural views penetrate all the way to the deck plates. You have to check it yourself.

Yeah, it's interesting. Years ago, we were adding factories overseas in different countries at the same time as we were ramping up our production. And, and somebody said, well, like, how are you going to vet the factories? And that kind of thing. And I'd had somebody come back from it, from one of the factory tour, investigate. And they talked about the things that they saw there and smelled. And then I realized, oh, so there's the, like, critical, objective things, like, you know, how many of this and what of that and the things that you could directly inspect, observe, measure. I said, but then there's something else, because people know some of that stuff and they'll do their best to spoof you if they want to spoof you. But then there's the thing that's harder to do. And I called this the sniff test. And I think it applies to, like, everything. What does your gut say? And literally there were factories that we could go in where they smelled so bad. Either, either like chemical, biological, like something just was off. And you'd be like, wow, this whole place feels wrong. The expressions and people are wrong. I don't know what the facts are here, but I can just tell you something ain't right.

And I'll tell you a good friend of mine who ran and runs a, a large industrial organization. I've, I've gone around with him a couple times, and he would walk through a factory with a plastic bag and he would pick up all the loose stuff that he found. And he didn't dump on people, he didn't yell at people, but they saw him. He was setting the standard. And I guarantee you, you know, the second time he would walk through a factory and he had a whole bunch of factories. Those places were spick and span. It came from the culture, came from the top.

Isn't that great?

And one of the things I look at in an organization is almost every organization has five things up on the wall, right? Five values or things they believe in. And I tell people everybody has those five things on the wall, but not everybody has good culture. And good culture is whether people want to run to work in the morning, whether they feel like they're being taken seriously, whether they feel like they're being held to a high standard, whether they feel like they're being taken care of at the same time they're being held to that high standard. And you can, you can, like you use that metaphor, but you can almost smell it when you go into a place. If, especially if you're an experienced leader, I can walk onto the bridge of a ship that's about to get underway and watch them go through this process of getting underway, you know, and doing all that. And I can tell you within 10 minutes whether it's a good ship or not.

Isn't that awesome? Yeah. And you know what? In the beginning of anything, you don't have that awareness. You don't have that sensitivity or situational awareness. It's like everything's overwhelming and you don't see all the detail. But people talk about, like, how, you know, a beginning tennis player will, like, the ball just comes at them and they see nothing. And then a really masterful player or pro player can see the spin and the. Where it's coming and that kind of thing. And I think about the first few skydive jumps I took, and like, in the beginning, it's just a whirl of stuff. And then after a while, I could start to see and I had more body awareness and that kind of thing. Like, in any pursuit, there's a elevation of your awareness and sensitivity. Like a flying thing, right?

Yeah. I think. I think that there are essentially four things that determine whether somebody is going to be highly successful in their. In their chosen profession. One of them is natural ability. Everybody's got a certain amount of that. Another is the quality of teaching that you've got, whether they're teachers on the way up or mentors or what have you. Another is your personal motivation. How hard do you work? How bad do you want it? And then the fourth One is experience. 10,000 repetitions or whatever Malcolm Gladwell said. And I found that I studied baseball, hitting a baseball a lot, and I found that, like, the best hitting coaches were the ones who had the least amount of natural ability and had to work the hardest in order to. Became. To become great coaches. Well, I want a coach like that. I don't necessarily want the person who was like the star at the pinnacle of their profession teaching me. I want somebody who had to bust their ass to get up there so they could show me, you know, firsthand all the lessons they had to learn on the way. But if you could, and I would, I'll candidly tell you, I didn't come into this business with a whole bunch of natural ability ability. I had some, but it was hard work. I had great teachers. And then, you know, just paid attention along the way, questioning attitude, and eventually you wake up and you go, I think I know this business, but I still have a lot to learn.

What's the hardest lesson or moment that you could think of in. In your leadership experience, the, the deepest challenge that you think you've had so far?

You know, there were a number of them, but I think that the most personal, hard challenge was having to take a young man's wings away from him and. And it Was it would have been easy actually if the guy had been flat hatting, had been breaking all the rules and that sort of thing. But this guy really wanted to be a good pilot and really tried hard, but he just wasn't good enough and he was going to hurt himself or hurt somebody else and you know, but you know, you have to do the hard thing sometimes in pulling somebody out like that. And in the process you do it with compassion. You try to set them up for success somewhere else. But I think those are the hardest moments is getting ready, getting, you know, having to cut somebody loose who really does want to succeed but just isn't making it.

Yeah, you know, that's an interesting one and I think that comes up regularly for our, the leaders who watch our program and that they have to deal with people who are just not suited to the role that they're in. And a lot of times we have self delusions we want to be that pilot or whatever when we should be in some other role and you might like it. That's the sort of the fallacy that Malcolm Gladwell doesn't. You could spend 10,000 hours at something and still suck because it's just not where you belong. I've spent a lot of time running triathlons and marathons and I'm never going to be on the podium. It's just not wired in me. But I've developed and benefited immensely from doing that work and enjoyed it. But I just knew that I was never going to be competitive. It's just not the whole. On the other hand, leading a show or doing some of the other work I do, I might easily be the best in the world at some point in some aspect of.

Yeah, I couldn't agree more. And you discovered in your triathlons and the like that the people who succeed are the ones who keep going after everybody else quits.

Yeah.

And you may not make the podium, but you're going to do pretty well.

Yes. I have a really good transition right now, getting on and off the bike, getting in and out of the water though. I'm fantastic at those things.

You just have to do it.

Yeah. It's just the times in between that I'm not very fast.

I know the feeling. Trust me, as I get older, I know the feeling. Feeling.

I remember one day I was out swimming off Coronado and. And I think it's beautiful. And I'm a little like, I don't know what the current's doing here. And I'm not, I don't live down here. Normally I was just down on vacation and getting a swim in, and these four guys come just swimming right past me, like in formation, swimming together. And I'm like, oh, yeah, they're. They're at the base down the street there.

Yeah, right. Yeah. And they were swimming north to get away from the sewage, probably. But, yeah, those guys are pretty amazing.

That's pretty hardcore. So, yeah, that's an interesting thing. And then who's the best leader that you've learned from or observed or one or two? I don't. You probably observed a few that you thought had some fantastic qualities.

Yeah, I work some for, for, for the whole spectrum. I work for leaders that I learned the sort of. Okay, I'm not doing that from. But I was also very blessed to have a chance to work for some amazing leaders. And I think, you know, who better than General Colin Powell? I was his aide for a year. I worked on the Joint Staff before that for a year. So I was observing him and briefing him and doing things, and then I actually worked directly for him. And he was just remarkable, both in his wisdom, his ability to bring disparate concepts together, his understanding of human nature in a discussion and a negotiation, and also his whole leadership philosophy. And I'll never forget this. You know, probably the best leadership SOUNDBITE lesson I ever got was riding around in the front of a car one day, and, you know, he didn't usually talk too much to me when I'm in the front seat, you know, the baggage carrier, and he's doing important work in the backseat. But he said, you know, Sandy, the essence of leading people is holding them to the highest possible standards while taking the best possible care of them. I went, wow, how profound is that? Because if you do one and not the other, it doesn't work. But if you do them both, it's magic. And you. It. Same thing with your kids and same thing with young people who work for you and certainly older people who work for you. It just works. And that's, that's probably other than, you know, character mattering more than anything. That's probably the most important leadership lesson that I, I learned and digested as I came up through the, through the ranks.

Yeah, It's a beautifully stated thing. And you could pick it apart. Right. So if you just take care of people without holding them to a high standard, that's coddling. And if you go crazy on you.

Right.

And if you don't take care of people but you really push them, that's driving them too hard. That's Running them into the ground. Right. It's that combination of the two that's a, that's a beautiful tension of really caring for them, but also like calling them to rise up.

Yeah. And, you know, there's an old saying that morale never rises when standards fall. I would also tell you that a sailor, soldier, airman, a Marine will run through a brick wall if you do two things. One is hold them to the high standards and, you know, take care of them and make sure they know that. And then the other thing is to do your best to make sure they understand why they're doing what they're doing. And, and you usually have time to do that. You know, you don't have to give, give a big long explanation, but telling, telling them, making sure they know how important it, what they are doing is. Now there are times, you know, in the stress of combat, you know, you don't have time to say, well, here's why we're going to do, you know, it's like, go do this. But they get that. And I think those are, are powerful things for getting people highly motivated to do very difficult things.

So that's a great place to maybe go and spend a minute on. Sometimes business people envy military leadership because they have power. Right. They can say, do this and that, people have to do that, or you can put them in jail and you have absolute authority. It's Machiavellian where business leaders don't people just walk off the job right now. People can desert, people can go awol, but you have a different kind of control. And yet we see that. So how's that different today? How do you contrast military versus business leadership?

Yeah, it's really interesting. I'm on the compensation committee for two major public corporations and it's eye watering to see what some of the motivation that's applied in that world.

But, I mean, in the pages.

Yeah, and, and that sort of thing. But, but it is, there is a difference there, I will candidly admit. It's not like people are yelling in the military and do this or else, you know, that kind of thing. But, but there is the expectation that if you put out a task that it's going to get, you know, accomplished. And, but, and there is an expectation there that if, particularly with your, your most close leaders, subordinate leaders to you, that if they think you're making a mistake, that they have the license to come in, in private and say, hey, you know, Admiral, I think, you know, you may want to consider this aspect of that. And then, you know, if you explain to them, well, why it is you're doing what you're doing, they'll walk out the door and execute or you may actually learn something and you might modify what you're doing. So there is that, that particularly at the senior levels in the military, there is that healthy dynamic. And where that healthy dynamic does not exist, you see leaders that will fail. But I also think that in the civilian world, and there's a little bit of an adjustment there, that, that there's more, you know, persuasion required more mentorship. But I've also seen some pretty edgy leaders in the civilian world who are tactful but, but edgy and that their expectation is high that people are going to do what they expect them to do. So it's not as far apart as you might imagine, but there are, there are some differences there and it depends on the leadership style.

Of course, I remember like with our companies today, we talk about Simon Sinek start with why. We talk about the purpose. We talk massive transformational purpose. We talk about aligning our long term goals to purpose so that we're fulfilling something that people care about. There's some feeling, there's some emotional drive affecting their actions and their decisions and that's a big factor. And but I also remember in the military it was only a tiny thing like we'd have some threat briefings that are supposed to scare you about some guy come out and act like a Russian general and try to paint a picture of something. But it wasn't like a daily thing like this matters today because remember, we're doing this. That wasn't such a high thing. And I wonder if that's changed in how you contrast those.

I think it depends a little bit at the level of leadership in the military. At the unit level it's less, here's why we're doing what we're doing kind of thing. Whereas at the higher levels there's some real intellectual work going on there. How are we going to solve this problem? How are we going to take this on? And what are all the various dimensions of this thing that leads to considerable amount of complexity that, that bears the kind of discussion you're talking about. So I think it matters there a little bit. And back to the sort of same discussion we're having. One of the things I think under these five pillars that I've got leading yourself, leading people, leading organizations, leading execution and leading change. Well, within leading organizations there's a little thing that says understand power and all the different types of power. There's reward power, there's coercion power, there's referent power, there's expert power. And again, along the way, it's a good thing for aspiring leaders to learn and understand that. That's just one little slice of all the things you have to try to learn if you're going to be a good leader. And you kind of referred to those and your last discussion there.

Yeah. So it's a great framework and thing to think about those anchors. You got to start with yourself. Right. If you're not managing your own motivation, your own integrity, your own rigor, your own prep work, your own work quality. Right. How could you possibly lead other people if you could fake it for a minute, maybe. And we see people sometimes doing that, but then it's going to catch up to you.

Yeah. You know, and each of these anchors that I have, you know, sort of has four threads. And one of the threads in leading yourself is what I call manage your brain. And that, that gets into a combination of managing stress and also sort of poise under pressure. You know, Colin Powell had a saying, never let him see you sweat. Right. I mean, you could be going through the worst possible crisis. And I've been, you know, in a situation where, you know, there was a merchant ship that was trying to hit USS Enterprise and I've got to, I've got to take a very bold move to avoid it, but I can't be there panicking and yelling and screaming. It's just got to be, you know, cold, quiet, calm. Let's do this. And when people see that, they stay calm. And if they see you panicking and yelling and screaming around, they're going to panic and yell and scream around. So that that sort of managing your brain piece is important. And then, you know, the managing stress part, I think that a lot of leaders don't necessarily do well and it shows. But you know, in naval aviation, we have a sort of a way of doing this. When you're trying to land an airplane on the back of an aircraft carrier in the middle of the night when the deck's pitching, that's not when you want to be thinking about your love life or your parents health or your financial situation. And we literally teach people to put those things in a little box in the corner and bring them out when they need to be brought out, when you have a chance to deal with them, but literally, in your mind, put them in a box in the corner and focus on what you're trying to do.

Manage your brain, you know, so this is a good thing to highlight it and point out for our listeners, there's all different kinds of leaders and every organization has leaders in different areas. Right. And you might be really good at planning and orchestrating things and thinking through all the minutiae and the detail. You might be really good at inspiring people. You might be really good at helping people find their part of something. You might be really good at keeping the team dynamic together. You might be fantastic with strategy and you might be a great coach who people just look up to and they want to be around. Like you could be any of these kinds of things, might not necessarily be great at all of them and you might need to lean into them. But not everybody is cool under pressure and not everybody has learned to figure out how to handle stress and change and not see and yet manage yourself in a sustainable fashion. Right. It's not a normal kind of thing for a lot of us to do that.

It's not. And I think that the more you can be exposed to situations like that as a young person, whether it's through athletics or some other endeavor to kind of get yourself accustomed to those stressful situations rather than kind of sitting on the couch, I think the better off you are to handle those stressful situations. Yeah, no, I totally agree.

Finding a way to. So I know that in a total crisis I'm really good. And it probably started because my parents argued and were fairly dramatic and, and I had to kind of be the oldest kid and keep things together. And then later I had some extreme experiences. I was around a bombing and I, you know, I dealt with loss of life and things like that and I could stay very cool. And even now in a, in an economic meltdown, in some financial crisis, in a business crisis, I can stay very level headed. And then later I have to manage my emotionals because I, you know, there's a, there's a account to refill, to sort of recharge yourself after you've dealt with something like that. And I'm really great with strategy and the persuasion, but execution, the consistent like day to day, the routine things. I hate that stuff. Like it just like that's for somebody else. Right. So I've just learned, instead of beating myself up for that, surround myself with people who like the routine, who like to follow the plan, who don't need to reinvent everything.

Yeah. I think one of the things though that whether it's a leadership topic or just a success topic, that especially when you get leaders who have been in a lifelong specialty who are now migrated into a broader world. So let's say you grew up in a CFO pipeline and you've been a CFO your whole life, and now you become the CEO and you got a lot, a lot of other verticals that you're playing around with there besides the cfo. The temptation is to migrate towards that CFO thing and, you know, because you're comfortable there.

Yeah.

And I think a good leader has to really work hard to become as expert as possible in those other verticals, business verticals, or whether in the military, whatever, so that you can be that good, good, good CEO. And, you know, early on in my career, I decided that, that I absolutely hated paperwork. It was the bane of my existence. So I decided, well, and I knew people who, when they hated paperwork, they'd stuff it in a corner and it would stack up literally feet high when I, I can tell you stories. But I decided that I, if I hated it, I was going to get really good at it. Because if I got really good at it, then I could slay it. I could get it done quickly and push it out of the way, get that thing over with and get more into something that I really enjoyed doing. So there is that sort of, you know, migrate toward the thing you hate.

Lean into the discomfort. Yeah, yeah, yeah.

And then, and then get off to what you really like doing.

Yeah. So I like. You have to develop some routines around something, structure a plan. You have to develop a muscle for something that might be a challenge or it'll trip you up. Right. That stack of papers that you were supposed to have dealt with will bite you in the butt with something that you didn't do. And a mission or a team or something is going to go wrong because you didn't do your paperwork.

Yeah. And I think, I think that one of the things that leaders can do that's the most valuable for their organization is to instill habit patterns in the organization that are good. Habit patterns. It's not just words. It's actual habit patterns in the organization. And one of the most formative experiences for me on the execution side was I was a fighter pilot. And then I went into the Navy's nuclear propulsion program. I had to go to nuclear power school for 18 months. It was the hardest thing I've ever done in my life, academically.

Yeah.

But what I learned from that program, because, you know, knock on wood, they haven't had an accident in 75 plus years of operating hundreds of nuclear power plants. And there. It's not an, it's not an accident, it's not a fluke they have a number of operational excellence principles that they. That are very simple. You know, integrity, level of knowledge, procedural compliance, forceful backup, formal communications, and a questioning attitude. And you usually find that when there's a mishap or a big mistake, that it's two of those things that were violated. And then if you debrief those things in the context of those principles, it wasn't like, what went wrong here. It's like, hey, what principles were violated? It only reinforces that culture and those habit patterns inside the organization. So I think if a leader can put out a very sort of easily understood, simple sort of rubric for establishing habit patterns and then reinforces those patterns, I think it'd be very valuable for an organization.

You know, we talk about that again and again. The fundamental people like, oh, yeah, values. Values. Like that's like when you not only have values that are real values, and you're actually training and organizing your behaviors, your patterns, your routines around those values. And. And then when things go wrong, looking at them from that lens, so valuable, so fundamental. And if you want to go from leading a small team to leading thousands, if you've instilled values across the organization, then you don't have to watch everybody every second, right?

And if you have an organization that's growing from tens of people to 100 people to 200 people, I call it cultural dilution, where if you're not careful, a leader has to probably be saying something more often than he or she thinks they need to be saying it in order to retain those cultural aspects. As you get larger and larger as an organization, sometimes it can be quite simple. You know, I'm on the board of Enterprise holdings, which owns Enterprise national and Alamo Rent A Car. And you know, the founder of Enterprise Rent a Car, who was a Navy fighter pilot in World War II and happened to fly off of USS Enterprise, said something very simple. You know, take care of your customers, take care of your employees, and the bottom line will take care of itself. And they live that to this day. And it's why they've got the best customer service of any rental car companies in the country. You know, three. All three J.D. power awards. Why? Because they take care of their employees, they take care of their customers. It's amazing how simple it is.

You know, one of our past speakers, General Stanley McChrystal, and he said something pretty memorable to me, talking about reorganizing the way they. They did special operations and. But he said, a farmer never grows anything. And I think about it all the time. A farmer plants do the growing. The farmer creates conditions for growth and so too the leader, you know, you create the fertile ground, you give it water, you hopefully pick a spot with some sunlight. You know that that's the farmer's job is to create the right conditions for growth. I think it's powerful metaphor for leadership.

Yeah. And so the Latin root of culture is cultura, which is essentially good soil.

Oh, isn't that beautiful? I did not know that. I've always told people culture, the root of it is cult. And so you should create a cult of your own design. A good cult, not the weird cult, right?

No, but Stan, Stan, I was around him, visited him in Iraq or Afghanistan. One of the other one, he was running the JSOC out there and he really did have that place humming a complete culture change that. And they were, they were amazing what they were able to accomplish. So I think the world is. Stanley.

Well, I could keep talking to you for a long time. This is such. I've been excited about our conversation and it's been thrilling and I would love to hear more stories. We're going to run out of time here on our clock, but I want to tell our listeners viewers to go get yourself a copy of Sailing Up Window Wind Sailing Upwind. Is the book Leadership and Risk there? Put it on screen. Yeah, from Top Gun to the Situation Room. We'll put the link, it's right there on the screen and then we'll put the link also in in the show notes so that people can get that in in our email blast and that kind of thing to follow up on it. But I look forward to seeing you again some more soon. Yeah, it's been outstanding.

Pleasure. Writing the book was a labor of love and I hope I pulled it off with humility and I hope your listeners are able to check it out. Thanks for having me on.

Well, it's a brilliant metaphor and you've got a tremendous number of stories in here that I think we can all learn from. A couple shout outs to some of our folks. Wanda Mitchell gets our show ready every week. My friend and mentor, Vern Harnish, who created the Rockefeller Habits and the scaling up framework that we use with our growth clients. And then to the folks at Podfly Productions who get our show ready and out the door every week. It's such a pleasure to work with everyone who just gets their job done now year after year, now 500 or so episodes in. It's awesome source the great team. Thanks again everyone for watching, for listening. Until then, keep scaling up. Foreign Are you ready to turn your goals into daily wins? You should check out our Scoreboard software powered by Align. It's the official software for scaling up. With Scoreboard, you'll get an AI driven coach for priorities and KPIs and it'll help keep your team focused on what matters most. With Align, you can track your goals in real time and you'll even see results on the go. With their mobile app, you can rest easy knowing that Align has world class onboarding and support to set your team up for success. This is really more than just software, it's what I actually use to manage growth in our scaling up client teams. Unlock clarity and results with Scoreboard by Aligned. To try it now, go to aligntoday.com Bill G One more time. Aligntoday.com Bill G that's aligntoday.com Bill G Check it out and try it now.