The Daily Stoic - Major General Dan Caine on Becoming a Great Leader

Episode Date: October 9, 2021

On today’s podcast, Ryan talks to Major General Dan Caine about the importance of defining success before you set out to try to solve a problem, the responsibility of leaders to be as prepared as possible, the ineffectiveness of holding others to the standards you hold yourself to, becoming a lifelong student of leadership, and more.Maj. Gen. J. Daniel Caine is the Director of Special Programs and the Department of Defense Special Access Program Central Office (DoD SAPCO), the Pentagon, Arlington, Virginia. He has commanded a joint special operations air directorate, a joint task force and a group. Maj. Gen. Caine is a Command Pilot with more than 2,800 hours in the F-16 and has served as a Joint Terminal Attack Controller in a special mission unit assigned to the U.S. Special Operations Command.Sign up for the Daily Stoic Leadership Challenge: https://store.dailystoic.com/products/leadership-courseTalkspace is an online and mobile therapy company. Talkspace lets you send and receive unlimited messages with your dedicated therapist in the Talkspace platform 24/7. To match with a licensed therapist today, go to Talkspace.com or download the app. Make sure to use the code STOIC to get $100 off of your first month and show your support for the show.Cometeer partners with the best locally owned roasters in the world and through their breakthrough brewing technology, provides a delicious, high-quality, balanced cup of coffee for a fraction of the price. For a limited time, you can save 20 Dollars off your first order - that’s 10 free cups on your first order, and shipping is always free - but only when you visit cometeer.com/STOICLinkedIn Jobs is the best platform for finding the right candidate to join your business this fall. It’s the largest marketplace for job seekers in the world, and it has great search features so that you can find candidates with any hard or soft skills that you need. And now, you can post a job for free. Just visit linkedin.com/STOIC to post a job for free. SimpliSafe just launched their new Wireless Outdoor Security Camera. Get the new SimpliSafe Wireless Outdoor Security Camera, visit https://simplisafe.com/stoic. What’s more, SimpliSafe is celebrating this new camera by offering 20% off your entire new system and your first month of monitoring service FREE, when you enroll in Interactive Monitoring. Just go to https://simplisafe.com/stoic to claim this deal.Sign up for the Daily Stoic email: https://DailyStoic.com/signupFollow us: Instagram, Twitter, YouTube, TikTok, FacebookFollow Dan Caine: Twitter, HomepageSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Hey, prime members, you can listen to the Daily Stoic podcast early and add free on Amazon music. Download the app today. Welcome to the weekend edition of the Daily Stoic. Each weekday we bring you a meditation inspired by the ancient Stoics. Something to help you live up to those four Stoic virtues of courage, justice, temperance, and wisdom. And then here on the weekend, we take a deeper dive into those same topics. We interview stoic philosophers, we explore at length how these stoic ideas can be applied to our actual lives and the challenging issues of our time. Here on the weekend when you have a little bit more space when things have slowed down, be sure to take some time to think, to go for a walk, to sit with your journal and most importantly to prepare for what the week

ahead may bring. Hi I'm David Brown, the host of Wendree's podcast business wars. And in our new season, Walmart must fight off target, the new discounter that's both savvy and fashion forward. Listen to business wars on Amazon Music or wherever you get your podcasts. Hey, it's Ryan. Welcome to another episode of The Daily Stalk Podcast. One of the best experiences I've had in all of the cool stuff we've done with Daily Stoke over the years, has been over the last nine or so weeks

this leadership challenge that we did, called it the Daily Stoke Leadership Challenge. You know, a lot of our challenges have been like 10 days or five days or 14 days or 21 days, but this was a nine week challenge. Originally, I thought I was gonna be six weeks. We ended up having so much good stuff. It became nine weeks, basically an email every day for nine weeks. The best stoic thinking on how to be a leader, because although not all stoics are leaders, all the major stoics of history were leaders. Mark, it's really a cynic.

The major stoics of history were leaders, Marxus, Realis, Seneca, Musoneus, Rufus, Zeno. These were people who made things, who founded things, who led people, who made the hard decisions of leadership. And one of the coolest parts about the challenges we did these deep dives, these hour conversations with me and real leaders in different industries or domains, leaders in athletics, leadership coaches, leaders in academia, and then of course, leaders in the military world. And that's where today's conversation comes from. This is my conversation with major general,

with major general Daniel Cain, who is the director of special programs at the Pentagon in Washington DC. He was the first pilot in the sky on 9-11. He spent more than 28 hours in the cockpit of F-16s. He was the joint terminal attack controller in the special mission unit assigned to the U.S. Special Operations Command. He was also the deputy commanding general assigned to the Special Operations Joint Task Force in Iraq and Syria. He's a father, he's also had an interesting business career.

He started and scaled several companies. And I actually got connected, introduced to him by one of the directors of personnel in the Texas Rangers, the baseball team who Dan, who General Cain has been a long time advisor and friend of General Cain is just a fascinating figure. We've gotten to know each other. He's given me all sorts of amazing advice over the years.

And then it was interesting to see him and his mind said, even this, I said, hey, we're doing this little thing. I'd love to have you be a part of it. Which, which, could you spare an hour? He said, of course, I'd love helping leaders. I'd love to be a part of it. But he actually drove all the way out to, from, from Dallas to spend time with me to prepare for the interview of all the leaders, the only one to do that. Because he just was really committed to getting it right. He stopped by the, the only one to do that, because he just was really committed to getting it right. He stopped by the painting porch.

Bookstore and pictures and books, which I also appreciated. But it's just been really interesting to see him do what he does to talk to him about the events of the world. And he was just the perfect person as part of this program. Now generally, this would just be for members, for people who participated in the challenge when we did it live over the last nine weeks, but this interview was so good and so timely, I wanted to show it to you.

And so first off, I hope you enjoy the conversation. We just reopened the course, so you get access to all my conversations, the Q&A as I did, all of that, and you can check that out at dailystoke.com slash leadership challenge. I think you'll really like it. We've had some awesome testimonials. Actually, you know what, here, I'll give you one of the testimonials right now.

I really enjoyed this program. Thank you for I've done almost, almost all the daily stoic challenges since I started doing them like five years ago or so. And I have to say that the cost of the program and the amount of value brought in was quite amazing. So anyways, don't take my word for it. Listen to him. Check out the Daily Stoke Leadership Challenge at dailystoke.com slash leadership challenge and enjoy this very timely and wonderful interview with the one and only major general Daniel Cain I think it will help make you a better leader. You can follow him at Dan the one and only major general Dan Cain you can follow him on Twitter at Dan

underscore Cain with an e on the end on Twitter or go to his website at dancane.net. Remember that's D-A-N-C-A-I-N-E. Joy this conversation. A bunch of stuff about defining success, about communication, about responsibility, preparedness, the ineffectiveness of holding others to standards. You don't hold yourself to, and how to be a lifelong student of leadership. I think you're really going to like this interview. And I do think you're like the Daily Stoke Leadership Challenge as well. I wanted to start with 9-11 being this is the 20th anniversary.

You know, we've talked to a bunch of interesting leaders in the course of this course. And they've been through some crises and difficulties, but nothing quite like being one of the first planes in the sky on 9-11. So could you maybe walk us through that day and what that was like? Of course, yeah, it's hard to believe it's been 20 years, you know, last weekend and it's just strange to look back on that. On September 11, 2001, I was actually stationed here in Washington, D.C. out at Andrews Air Force Base. I was flying F-16s, I'd been to the Air Forces, Top Gun School where we don't play much volleyball, we mostly focus on getting better as tacticians with a little bit of gestors

my Navy brothers and sisters. And we had just gotten back as a squadron from out in Las Vegas and now, a Salesforce space for we were getting ready to deploy. And that Tuesday here in Washington was a beautiful and gorgeous day. And I was not scheduled to fly that day. I was originally sort of running the flying operation for the squadron as the chief instructor and tactician.

And as we came in that morning, we obviously had no idea what we were going to face. And we were in a meeting at the squadron, just a training meeting when one of our young intelligence professionals came in and said an airplane has just hit the World Trade Center. And of course, my first thought was to small civilian airplane, this couldn't be. And, you know, we all, as you get older, as leaders, you start to develop that spidey sense of just something's not right. And I felt that got up, walked into our, our squadron lounge where we had a big flat screen TV. And, and remember, I still get chills today, even remember clearly the helicopter news shot showing the first tower burning when the second airplane flew into the picture and hit the building.

Silence could have heard a pin drop and we sat there for what seemed like a long time, which was probably just a very few seconds. And I went to the desk where we had all of our communications gear. And I picked up the phone and called the Secret Service and said, I don't know what's going on, what he needs to do. We had a relationship with the Secret Service in Washington because we flew out of the same airfield as the president. And the next phone call was the White House saying, get anything you can airborne. The nation is under attack. And right at that point in time,

my boss, Brigadier General Dave Wurley walked in and I handed him the phone and I said, hey, sure, this is for you. And we went and got ready to fly. And it was myself and a wingman and there were two other folks as well. And we got our gear on and went running back to the ops desk and met General Worley. General Worley read us the rules of engagement for defending the national command authority. It was very liberal and it was on us. And you know, when you think about leadership for the folks on the call and on the video here, I will never forget what then General Wurley said to us.

He's just read us the rules of engagement, which are extremely liberal. The decision is clearly mine. It's the cap commander, the mission commander over the combat air patrol. And he reads this verbatim. And then he pauses and he looks at us and says, hey, Dan, look. I don't know what you're going to face out there. I think you're probably going to have to make some very

difficult decisions, but here's what I want you to know. I trust you. You're going to do the right thing. And no matter what, I have your back. And you want to talk about saying the exact, exact right thing at the exact right moment. We ran to the jets and scrambled and we're flying that morning.

We took off, I think, right around the same time that the real heroes or some of the real heroes of that day, the passengers of flight 93 were assaulting inside the airplane, knowing full well what they were facing, knowing what had happened in New York City, and yet finding the courage to step up, not having taken the same oath that we take to uphold and defend the constitution, but knowing

that their nation knew them to do something. So, flew that the rest of that day and a lot of intercepts and a lot of sort of keeping airplanes away from downtown Washington and our swatter and flew for the next 45 days after that. And I deployed pretty quickly overseas to start fighting Al Qaeda. What's to bring all that together? I think there's a couple interesting themes. So one, which is open lines of communication. I think it's pretty incredible that you're just sort of very quickly on the phone with the White House.

I was reading a book about Admiral Rickover recently, and I didn't, they just sort of mentioned it offhandedly, but I guess for maybe it's still the case, but it was the case during the Cold War, that every commander of a nuclear submarine could directly call the White House. Like there was just a phone they could pick up and it would ring at the president's desk. And so I think sometimes we think these these organizations are huge and

there's this massive chain of command, but at the top, it sounds like, well, we didn't call, they called us just to be clear, you know, I called the secret service. But that's what I mean. That's what I mean. Yeah, yeah. Yeah. Is that at the end of the day, at the really elite operators, you have to be completely flat. There has to be open lines of communication and flexibility there. And flatness is something from a leadership perspective that we value greatly. Certainly I value greatly. And I drive the organizations that I'd bless to lead or be a part of towards that flatness. I think as leaders, if we don't understand what is happening

at the edge of the empires that we're blessed to lead, serve, and to end the help with, then we can't possibly understand what's really going on. It's a flatness as a key to that. Yeah, because often, you know, I think especially at the lower levels, you can be like, well, I pass this up the chain and something will happen.

But I think it's interesting that you called the Secret Service, you didn't sort of wait around and say, let's see if somebody needs me, let's wait to see where this goes. You sort of use the contacts you had on that day to sort of say, you know, what do you need for me? What can I contribute? What's going on? I think we've got a responsibility as leaders at whatever level you're leading at to be proactive and not reactive, to realize when there's a white space and lead your organization or yourself towards that white space to improve

the overall effectiveness, efficiency, combat, whatever kind of organization you're leading and move towards the problem. When that goes to the passengers on Flight 93, which you texted me a transcript of that sort of call on 9-11, which it always sort of gives you the chills to read. I think the idea that they weren't sort of technically leaders in any way. It was a handful of people talking on phones on airplanes, which I think younger people don't even remember was a thing that you could swipe your card and get a handset out of the back of a seat. But they sort of anointed themselves leaders and it was, I thought it was remarkable is that you have this 911 operator relaying

information from all over the world, sort of that all these people involved, although they had no official authority, or even official obligation to do anything, took it upon themselves to say, like, look, we might not be able to solve this thing, but we can not contribute to the problem. We can not make this tragic event more tragic, and we're gonna try to do something. And I think, you know, I just And I think about them every day, right?

And that is real courage knowing what is going on in the United States at that point in time. And having the intestinal fortitude, the bravery to stand up and go forward knowing, it's just an incredible example. You know, America started to fight back immediately. And they were the first steps, the firefighters that headed up buildings were the first steps, you know,

the people of the Pentagon were the first steps. And out of this tragedy of September 11th, we can find incredible goodness on who we really are as a country. And I hope we just always take advantage of those examples moving forward. Yeah, it's almost easy to celebrate the firefighters and the police officers, but there were also the office managers and the employees and the people who had, you know, they worked in this enormous office together, but they never met before. And again, had no real obligation to anyone but themselves and decided, hey,

I'm not leaving anyone behind or, hey, I'm going to do what I can here. You know, that is also what leadership is. Leadership isn't this thing you get promoted to necessarily. It's also what you do in moments of crisis. Absolutely. Absolutely. And it could have been a lot worse that day. Had those people not evacuated the towers and those people stood in the stairwells and helped other people get down there or people in the Pentagon could have been a lot worse.

Were that plane, you know, Flight 93 could have crashed into the White House or the Capitol Building? It would have been much worse. And then when I think about leadership, although thankfully you didn't have to, it strikes me that what your commander was talking about was the idea that within the latitude that you had been given, you would have, you potentially would have to make

some very hard decisions in the moment, which is also something we've talked about, but sort of the definition of leadership to me is, you know, can you make hard decisions with limited information and limited time? Yeah, you know, and as I reflected on that day, and look, we just did our jobs. We just did our jobs, and thankfully,

we didn't have to make the decision to shoot somebody down. As I reflected back on that day and folks have asked me, were you scared or what was going through your mind and what not? I mean, of course, but overwhelmingly, the thing that, and I'm grateful for this experience

in some ways as a leader, my largest concern was not to miss somebody and not to be able to prevent, or be unable to prevent an airplane going into the White House, going into the Capitol. And that drove everything. And as I didn't realize it at the time, I was younger and a captain, you know, young captain. But as I've reflected on that over the years,

I'm grateful for that and other situations like that where I built some trust and confidence in my own instincts as a leader to be able to make difficult and complex decisions with limited information in short amounts of time. And that is something that I've learned that value greatly in my life. Yeah, and it strikes me as similar to the idea, as we talk about different organizations

and how they're structured, that what your commanding officer did there was give a really clear sense of what sort of commanders intent was. Like he was like, this is what you're being tasked with. These are the legal constraints that you have to operate on. Here's what I expect of you. And then he said, the rest is your call, right?

He sort of trusted that you're training, your judgment, your conscience, you know, your sense of duty would take care of the rest. Absolutely. And clarity of guidance, especially in today's day and age, and how you think, develop, and then articulate that guidance is so important to organizations, and so important to leaders to get it right and get it out there and stay consistent on what that guidance and intent looks like because in the end what that drives towards is what is the culture that your organization is going to embrace and how are you going to move the organization from where it is now to where it probably needs to be. And Gerald Whirlate, who tragically, in a horrible

story after he retired, was volunteering with his wife at Walter Reed Army Medical Center, and they passed away in a metro rail accident in Washington, D.C. Instantly killed the two of them together. So I don't know this. Yeah, I went to see his grave over the weekend and talked to this family, but getting that clarity, guidance, and intent right and then being consistent over and over and over again on what that culture has to be in order to achieve

that end state is really important. A lot of that comes down to sort of boiling it down to the ability in my mind to understand what is the situation, the context, the resources that you have, and then bringing those elements together into guidance and commanders intent. elements together into guidance and commanders of tech. Raising kids can be one of the greatest rewards of a parent's life. But come on, someday, parenting is unbearable. I love my kid, but is a new parenting podcast from Wondry that shares of our freshly honest and insightful take on parenting.

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So if you like to laugh with us as we talk about the hardest job in the world, listen to, I love my kid, but wherever you get your podcasts. You can listen ad-free on the Amazon music or Wondery app. So how can leaders get better at doing it? Cause I know like when I often look at mistakes that people who have worked for me or people I'm on a team with have made, it almost always comes down to

us not being on the same page about what was expected. And it's usually my fault. Like, usually I didn't explain what I wanted. By the way, I'm the same way. I'm always like, you can ask my teams, it's, I'm constantly saying the way, I'm the same way. I'm always like, I think you can ask my teams. I'm constantly saying, man, I have that up. I could have been a better leader. I gave crummy guidance.

And I think humility, authenticity, candor, and realizing that we're all students at this no matter whether you're a business leader, an educational leader, or a general or admiral in the military, you got to go to school on it. And I think back to your question, you know, I've spent a fair amount of time over the years thinking about how do I best understand the situation that I'm dealing with. And it started when I was a young fire pilot before I became a special operations officer. And it was, how can I learn everything about the adversary or the situation that I'm dealing with.

And that started this journey of insights for me. You know, I used to think about who am I fighting today? What kind of airplane are they? And what did they do yesterday at work? Did they go to sleep last night? What do I think they ate this morning? What's the weather like? How's their airplane configured? What how did I sleep? What's going on with me? How did I prepare? And just starting to think deliberately about asking really good questions to try to understand all the subtleties and the big levers, but also the subtleties of the situation that you're dealing with,

and trying to bring your organization into this conversation so that you can get an aligned stacking of hands on what the problem is. Defining the problem and understanding the problem together, I think is a key to gaining that understanding and context in the situation you're dealing with. And you're right, man. I'm in the exact same place. Man, I didn't give you good guidance.

You did exactly, my friend, as I asked you to do, and I give you shitty guidance. You did exactly, my friend, as I asked you to do, and I gave you shitty guidance. That's typically what I'm saying. I think defining the problem is very key. The other way, I think to look at it, then I'd be curious your thoughts. I guess this is a tad more important in this civilian world, but it certainly would make sense in the military world,

which is defining success. Like, what does success look like? What is this problem being solved look like? Because if we don't know what success looks like, how do we know how far to go? How do we know when we've arrived? How do we back out a solution if we haven't solved for what success is?

And I think that to me is the most essential role of a leader, whether it's a sports coach, whether it's a board of directors, it's a CEO or it's a person who's hiring a freelancer to help them on something, which is where are we trying to get here, right? What does success look like? Because there's lots of different forms of success for every project or person. And if you don't define a really constrained specific version of success, you might get a solution to the problem, just not the one you want.

And you're going to experience creep, you know? We're both friends with the Texas Rangers and, you know, I'm chocolateing because I've asked our mutual friend, Chris Woodward, many times, what are we solving for? Yes. And what do you mean by that? And I think as leaders, and especially for this great group of leaders who've taken the time to join this cohort, to sort of think about leadership, it comes down to that clarity and asking real questions. And I find, even for me, who I'm old and tired, but I still find that a decent

amount of the time, I'm not really asking the right question or we're not talking about the right thing. It's until you get to that root cause, that root area of specificity with though, by the way, even in business, because I spent several years as a business guy, even in business with enough specificity that then you can go measure, it is what you need to measure in order to determine whether or not you're on trajectory or off trajectory to achieve that in-state. And then having those routine stops along the way to make sure that you're pausing and assessing are we headed in the right direction or not? And that sometimes helps avoid creep as we as we move forward.

We're related to that and not to get you in trouble because I know you're wearing uniform, but it strikes me that the tragedy coming out of 9-11 from the civilian side is that we don't give the military who I think has done a pretty good job of the last 20 years. We don't give them great guidance and clarity on what success looks like. So we call it the war on terror. What does that even mean? What is success?

What is the actual outcome of Afghanistan or Iraq, right? We could put all the politics aside. I think the problem or the inherent difficulty in both of these ventures, which is an inadequate word. But it wasn't completely clear what we were doing, what success was supposed to look like, how long it was supposed to take, and is that where the creed comes from

and where the confusion comes from and then the difficulty extracaiting comes from is that you can have the most talented people in the world, the most dedicated people, the most committed people, the most brilliantly equipped people in the world. But if it's not totally clear what they're doing and how they're supposed to succeed, they're probably not going to be able to do that. Yeah, and there were some super talented folks who in the last 20 years have been in the middle of exactly what you're talking about. And we've talked about this. I'm a addicted reader. I'm your dream customer because I buy the hard copy, buy the audio, and buy the Kindlebook.

because I, you know, buy the hard copy, buy the audio, and buy the Kindle book. And I look forward to the next one, by the way. And I know I owe you some addresses. The... Of course. I would encourage everybody on the Zoom call to read the Afghanistan papers, which just came out ironically prior to the president's decision to leave. And I think you'll find in there, again, staying away from the politics of the decision, given that I'm an active duty military officer. But I think you'll find in there some very important nuggets and lessons about clarity of end states

and some interesting things to think about as we look at the way this amazing country of ours that is the best worst system out there, as our founder said, but it's difficult in transitioning administration over administration. And, you know, it's been, I think, for anybody in the military that's on the net or anybody that's spent any time over there, this is a bit of a challenging chapter to sort of see all of these things play out. Again, not a political comment.

I support the president's decision, but the trying to achieve and driving towards clarity of an end state, and then sticking to it, which is hard to do, if think it'll be what we learn out of this. Yeah, I think that's right. And one of the things I wanted to ask you, because as we talk to different kinds of leaders,

and I've talked to different leaders over the years, there's kind of this envy that envy or almost despair. It's like, hey, this isn't the military. I can't make you do stuff, right? We think about, if you're the CEO of a company, you have some control over the organization people, but much less, I think people speculate than if they were members of a regiment or you were a general or something.

But I think the operative word you used was guidance, right? Commanders guidance or commanders intent. Is that a myth? Is it, even in your organization, is it, and your line of work? Is it still much more about convincing people to do things as opposed to being able to make them do things? Right? Let's talk to me about that. Yeah, I mean, I think if you're a leader in today's military that has to say, I'm ordering

you to go do this, then we've got much bigger problems. And I have, I have never, that I can remember, said, I'm ordering you to go do this and making somebody do something against their will. I think I think world class leaders and I have a long way to go till I'm a world class leader are people who can use EQ as much as followers to get to an outcome that they want without using a overt directive force or rank for to make that happen. There is a certain level of respect, if you will, or deference that comes with rank in the military. But when I was in the private sector for a few years, I worked with a bunch of young

right out of college graduates who couldn't give a rat's ass what I did in the military. And it was all about my ability to connect, build rapport, sort of lay out the lie behind we wanted to go do something and then motivate, inspire, incentivize, encourage, love, occasional kick in the ass to go do this and they were fantastic. And so I think we need to be careful in civilian contexts to think that the military, of course, there's a rank structure and all that, but I just don't see, and of course, I do acknowledge I'm coming at this conversation as a two-star. But the same, I use the same approach when I was a captain, a dynamic, repetitive processes that allow them to connect with people, understand where those people are coming from, and then clearly communicate

where the organization is going to go, and then lead by example to bring that organization, whether it's a civilian business or it's a government entity towards that end state. Yeah, there's an Eisenhower quote that I love that I think I talked about in the last session, but he said the art of leadership is getting people to do things because they want to do them, which I love. You think about the immense power that he held, probably, in all of history, Do you think about the immense power that he held? Probably, in all of history, commanded the most men, the most power, and hopefully nothing like that will ever happen again.

And he's still thinking about persuasion and incentives and alignment. Not a force. All the time. And I mean, that's what I'm in the Pentagon working for the secretary across the interagency with outside organizations or with the various military services. That is what's running through my head.

Not talking to so and so or such and such and they're a particular rank. It's what's going on in their head. Where are they coming from? What is their motivation? What are they trying to achieve? What am I trying to achieve? How do I achieve compromise or if not, how do I recruit them onto what I'm trying to do through influence? I mean, Marshall, which you and I've traded notes on Marshall. Marshall was much the same way, right? I mean, these fantastic examples of stoic leaders who understood the sort of human power of influence and persuasion without having to walk around

putting their rank in the face. And MacArthur is a completely different case. Yeah, right. Yeah, I mean, when I got to imagine that as the military gets more diverse and more reflexive, reflective of the civilian world, all these things take on even more significance because it's not a bunch of white dudes from the same place, the same backgrounds, the same experiences, the same shared assumptions, boss and each other around. It's having to really connect and understand where different people are coming from with different experiences, different priorities, different ways of thinking, and

figuring out how you get them all on the same page. As opposed to, I am ordering you to do this, and you should be afraid of me, so don't don't ask any questions. Absolutely, and I think that comes down to how entuned with understanding culture and then adapting that culture towards what you need to get it towards and then being able to drive it home over time. And it involves, you know, this really set of dynamic skill sets that has to be adaptable. And if you're sort of a one trick leader, I don't think you're going to be effective in the future.

And so that's what's so wonderful about all of the folks on the Zoom and the call here, effective in the future. So that's what's so wonderful about all of the folks on the Zoom and the call here, they're all investing in time to develop their leadership skills and traits to be a broader set of tools. That brings up something important, this idea of being a student of leadership, right?

That it's not something that you just pick up because you're naturally charismatic or because you're brilliant. Walk me through your journey sort of studying leaders or there are some that you really admire. You talked about reading. How is your education as a leader gone outside of just trial and error and experience on the job. Well, I definitely, and you're so great about getting this quote out there, all leaders are readers, but not all readers are leaders. And I think Truman got it right.

And I think the ability for me, I started out as a young fighter pilot and then went on to sort of scale through that and then did a did a White House Fellowship in DC, which, which allowed me to gain real insights into civilian leaders and sort of into the special forces community and back into business and sort of bounced in and out of government over time. The consistent theme through all of that was this real sense of humility that I wanted to be a leader worthy of those amazing humans that I were blessed to be in the leadership of, whether it be in the private sector and business or in the military or in the interagency. So reading was the thing that allowed me to accelerate those insights. And it has been a part of my life since I was in college. I mean, I'm just, I can't get enough of it. And there's not enough time in the day that I can read.

I read a book a week, typically. I mean, and what I try to do is to be thoughtful and intentional about what it is that I'm reading based on the jobs that I think I'm going to so that I'm prepared ahead of time or if I'm encountering a situation I'll go seek wisdom of others who've been in the same situation. So I've read a lot of Marshall and all the forest folk books on on Marshall. I read David Rolls book on Marshall that we traded notes on and I had him on the podcast. Yep, absolutely. And what a great

what a great guy very kind with his time. I've you know recently been curious about the relationship between the Department of Defense and the intelligence community. So I'm reading about that interaction. I, of course, took a spin through World War II history. I'm curious about the rise of China and the juxtaposition of the fall of great societies. Routinely, I read this great book called The Daily Stock. You probably heard of it. But I think history repeats itself over and over again, and as leaders, if we're not mindful and deliberate about learning those insights,

then we let down to a certain extent those that were given the gift of leading. And I don't want to be that guy. I've always sort of worried that I'm not going to be worthy of the gift of leadership. And so I'm pretty serious about it. And I enjoy it. I mean, chair. No, and I love General Mattis' book, Calls on Chaos, because he talks about this a couple times. You know, he says, he says, one, it's not, you know, sort of that you can read. It's whether you are reading. And he talks, I really liked his concept

of being functionally illiterate. So if you have hundreds of books about what you do, you're functionally illiterate, right? Which is, which is almost more embarrassing than being actually illiterate. And I thought what he was saying about your line of work that I think is particularly important and I think just a slightly less high stakes version of it is true for all of us. He was basically saying, you can't learn on the job when you're sending people out into

battle because you're going to be learning your lessons at their expense. He's like, you can't be filling body bags as you figure it out as you go. And I think that's, you know, you're entrusted with people's time, with their careers, with the best years of their life, you know, in the civilian world. The idea that you're going to make a bunch of mistakes and have to lay people off or put people in the wrong role or not know basic things that you could have figured out by reading a book is not just stupid, it's very disrespectful and wasteful of what these people have entrusted you with. So I'd like that you said that. I couldn't agree with you more. And I think it's a responsibility

that we all have as leaders to be as prepared as we can be, and to be voracious readers across our entire career. And then after that, I think it just goes to being a good human, learning the lessons of history, and preparing ourselves as much as possible. Well, and this is a thing I think for leaders, it's like whatever position you're in, whether you just got promoted to sales manager, or you're the executive of a Hollywood studio, or you just got, you know, you're you're a rookie in the NFL, or you're, you know, you're the executive of a Hollywood studio or you just got, you know, you're rookie in the NFL or you're, you know, you're a midshipman at the Naval Academy. Somebody has been there before and written a book about there is a memoir about basically everything that's ever

happened. And so the idea that you would not want to experience like, not want to experience the thing multiple times. I think Milan Canberra in the unbearable lightness of being me, is it's great line about how the problem with life is that you only learn by doing stuff and you only get to do everything one time, right? You never, you don't get to run your life over and over again and take the optimal path. But I would push back and say, reading is the one way that you get extra cracks at something. You want to learn from the person who was a congressman

and screwed it up. You want to learn from the person who was a congressman and then became president, right? Like you want to go through the different cracks or run throughs or reps of whatever you're going through, and then hopefully build on that, as opposed to being, you know, the first, whatever you just got promoted to,

and acting like you discovered, you know, Terra in Cognita, and that this is all brand new, fresh territory that's never been explored before. Well, that goes to the genuineness of humility and being worthy of the command that you're given or the leadership opportunity that you're given. I know when you're young and you get into your first management role,

you probably think, I got this, but I sure maybe early on did, and then I realized I have so much to learn, and I still feel that way today, where there's just this genuine desire to be as prepared as I can be, and that translates into a lot of reading, and always learning, you know what?

And I think it also, to your point about reps, we don't get a lot of them. And I think there's this decay, and this is why I think this program so great. There's this, I think there's this decay in American leadership across the entire continuing government, business, industry, you name it. And only through accelerating insights, are we going to gain detraction and the proficiency

needed to be who we can be as a country. And I know American exceptionalism and the meritocracy are starting to degrade a little bit. And, you know, when you, when you flick past that outer shell, how much breath and depth is in there and subject matter expertise and leadership, and it's a little, it's a little concerning. No, I was just reading something about China, and I'd never thought about it this way, and it was interesting. They were talking about how almost nobody in the Chinese military has any combat experience. Because China has been isolated for so long,

and didn't get involved in a number of global conflicts that we have. Outside of basically their brief involvement in the Chinese war against Vietnam, and then some UN joint missions, almost no one in the Chinese military has any actual combat experience. So it struck me as one,

obviously experience is a great way to learn, although it's very costly. And so you could see that as both a blessing and a curse, but it also struck me as like, wow, I better, they better be doing a lot of reading, right? Because you are missing by not having the firsthand experience, you're at an enormous disadvantage as costly as, as some of the mistakes and blunders that America has made

over the last 50 to 60 years, they have been educational in a lot of ways. We failed to not always learn lessons, but I was thinking about how if you don't get a lot of reps, it almost increases the need to have to be an avid student of whatever you're doing because you're having to make up for lost ground. student of whatever you're doing because you're having to make up for lost ground. Yeah, I'm pretty sure the Chinese are reading all of our books. And probably try to get into a lot of our computer systems to read those books that are not you have published. Well, what does your reading routine look like? Like, how do you, because you mentioned you read in all the formats? How do you think about it?

Yeah, I mean, my days are somewhat set at this point in my life. You know, I get up between four and four, fifteen and I, I don't know, I'm an early rise. You're on the Jocco track. I think I normally beat Jocco out of the rack. So it's a good way to start the day being a seal out of the rack. I think so. And, you know, I'll read hard copy books then. I read some philosophy. I read some faith stuff early on. I do some journaling in the morning. I've been doing this for years and years. I'll write letters to my to my daughters every morning and send them something on text or Instagram. And then I'm religious about working out. I get to the gym early on in the morning

between six and six 30. I'll listen to books in the gym. I'll listen to podcasts in the gym. I'll then sort of come back and get ready for work. I'm listening to a book on tape going in. I'll occasionally take a scan through the news, but if the crap hits a family will hear about it, and I think American mainstream media is struggling a little bit with antiseptically presenting facts. So that's not a political comment, just an anecdotal comment. And then I'm, I keep my Kindle generally up to speed

with the hard copy books because I travel a fair amount and I'll haul that with me and move forward. At the end of the day, I'll come back, I'll deduce some decompression and some thoughtful thinking about the day, how did it go, what did I do right, what did I do wrong, how can I be better? I'm a guy who's got, you know, always carrying around three by five note cards

or four by six note cards, so I'm taking notes there. And then putting them into the Evernote, which I've been using since like 2007. And then I go to bed, I'm super exciting. I'm going to bed around 8.30 at night. Wow. And the next day, and the next day off to the off to the races again,

but I'll tell you the morning ritual has been so good for me. It is so important to start that day with thoughtful deliberate stillness before the craziness of the day starts. I think you got it right in your book about stillness really being the key. And I just really strongly advocate for that

with all the people that I mentor and help grow as leaders, I think it just makes us so much better humans. And we're fallible. If we don't take care of ourselves and our families, we can't possibly be the leaders that the folks we lead deserve. So. I've got to imagine seeing your fair share of raw recruits or sort of people

from civilian life coming into the military over the years. How do you talk to someone who's sort of not a morning person and make them a morning person, right? Like what is that? Because I see this question a lot and someone asked it, but like for people who are like, oh, I could never get up at 4 a.m. Maybe they can't, maybe 4 a.m. too early. But how do you focus on sort of a leader's morning routine and focusing on the morning? I mean, it's more and more people are tacking that way and I'll say that I travel in.

So I think it's gaining traction. But it's just about asking thoughtful questions that allow them to get to that logical conclusion on their own. Like, what do you think is gonna make you the most effective leader for the people that you lead? And they start going down there and I go, well, you know, how do you ensure that when you hit work, first thing in the morning, you are absolutely ready.

And inevitably asking those really thoughtful questions generally leads to that self-realization that I got to change my rhythm, my daily rhythm to be as effective as possible. And you know, I mean, this is just the model that I use. I mean, I think I'm careful to make sure that people have a system and try not to force my system on them, as long as they're executing

to their maximum potential, which is what I'm always striving for in the cultures that I try to build. I think any system is better than not. For young folks, it's a lot of times they just need a little bit of guidance. Yeah, no, I think it's like, when do you do your best work? And how do you design your day around that?

And I think what are the chances that you do your best work at four in the afternoon after, you know, you put up with a bunch of crap and phones and air and stuff in the beginning of the day. I mean, I'm so serious about it that I block it when I get to work at the Pentagon. I block the first hour. just don't put any meetings in there. It's just thinking space and time to either read emails or read something and then I literally do the same thing at the end of the day. And because I know I'm very self aware that I will not be my best at the end of the day.

If I've been scheduled back to back, which happens a fair amount, I'm smoked at the end of the day. I'm not going to make great decisions. I'm not going to be as thoughtful as I probably need to be in these very complex matters that come into things. And so I just make a decision proactively back

to the proactive versus reactive. I make a decision such that back to the proactive versus reactive. I make a decision such that I can control my counter and I can't always put that on minute block that time. One of the questions I see here is actually from a deployed battalion commander. And he's talking about how do you deal with sort of gossip or rumors or I guess just, you know, the stuff that people talk about at work or disagreements or resentments, you know, the sort of negative stuff that a leader has to both be above, but also deal with because it can be cultural cancer. Yeah, totally, and that's a great

question. So thank you for who members deployed. Thank you for your service and for the service of your family for being overseas and taking care of our nation's business or our allies and partners business over there. You know, certainly in a military context as a battalion commander, you know, we are blessed to have a wing person, a command sergeant major who is a senior enlisted leader who's our wingman as a commander a command sergeant major who is a senior enlisted leader,

whose are wingmen as a commander, and whose job is to understand the sort of subtleties, tenor tone and direction of where the entire battalion is going. And when the CSM, the command sergeant major comes and says, hey, we've got these rumors and things like that. My approach has always been to not get buried down into the eaches and others, but to have a sense of when there's a lack of understanding of what's happening or where we're going. And I think as we have younger and younger soldiers, sailors, airmen, Marines, guardians,

I can't forget them now, and Coast Guard folks. Wait, if that's the Space Force? That's the Space Force. Yeah, Space Force Guardians. So you know, now I've hooked up. You know, I think you have to get a sense of when it's time to get an all hands together. And I did this in the private sector too,

when we did some layoffs, or we had things like that, which are very difficult. It's always better to sort of get at that and get clarity out there and be ready to answer those questions that come back to you, but to alleviate that distance between where you're trying to go as a leader and where the organization thinks they're going. And so I think clear communication is important. There will always be, especially in the military, there will always be a little bit of rumor going on. You're never going to fight that.

I think what you have to do is rely on your subordinate leaders, those leaders underneath you to help you understand when it's time you got to get everybody together. And I think you want to lean on to your company commanders and platoon lieutenants and PLs out there to get that culture right. When I start hearing a lot of rumors, I start hearing jitteryness in the system that tells me that maybe we're not talking about culture enough and we need to turn the volume up on that even more so that there's clarity all the way down the organization on what it is that we're doing. There's a great rule.

I heard as a writer, but I think it applies to business too or any kind of complaint, which is like when someone tells you that something's wrong, like with your writing, they're always right, right? And then when someone tells you how to fix it, they're always wrong, right? So the idea being, if someone's upset, they're not wrong. They are upset. They might not be informed correctly.

And so their solution is we shouldn't be doing this. Actually, the solution is I have to explain to you why we're doing this, right? So, when my editor comes to me and says, paragraph three isn't working, well, actually, maybe paragraph three stays exactly the same, but I have to edit paragraph two to explain why paragraph three exists. Absolutely. So I think thinking about it with a little bit of empathy and going, look, I'm not going to invalidate your feelings. Your feelings, your gripe is your gripe, but I can do a better job explaining to you why that's incorrect. I'm not incorrect, but why that needs to be seen in a larger

context. And I think we have to be authentically open to that feedback, right? Because if we're so egotistical and our ego is, you know, creating barriers to that receptivity, man, we're going to jack that up and we're going to be all hands up and we're going to miss that opportunity to realize that perceptions are reality and especially in complex organizations or complex situations or even one-on-one human to human interaction perceptions are reality. We just got to be sort of checking our ego at the door and it's about what's right, not who's right.

And if you just keep staying on that over and over and over again, I think you find that you start to figure it out with big asterix next to it that you always need to be going to school. Well, let's talk about the opposite of gripes and complaints and gossip. Let's talk about praise because I think there's this perception that the stoic is like sort of emotionless, that the stoic is so strict with themselves, they demand everyone else be strict. But to me, that's a recipe for being a bad leader. So how have you thought about praise, both receiving praise, but I think more importantly, giving praise as a leader to keep people motivated and committed to the mission.

Well, I think we're all humans and praise and feedback balanced with each other are really important components of good leadership. I've always thought of the appropriate way is to praise in public and critique and private. And I'm quick to let people know how great of a job that they're doing. And I'm, but I also try to be a little bit thoughtful

about how much volume there is on that, right? And I, not because, I mean, if they're doing a great job, I let them know that, for sure. But my point is that I want to create, at least in the military context, I want to create leaders that sort of have this stability to them. One of the things that I talk about is state frosty. When I'm talking to leaders who are going to combat or who are going to be in combat, I talk about, let's keep our cool, let's state frosty, right? In that context. about, I talk about let's keep our cool, let's stay frosty, right? Sure.

And in that context. And so, you know, when I want that, I want that praise to be deliberate, I want it to be intentional, I want it to be thoughtful, I want it to be also, you know, somewhat measured so that ego doesn't become an enemy down the road. Because in the end, it's about the deed, not about the glory. And a true selfless leader is one who doesn't care about a true servant leader is one who doesn't care about the glory, but cares more about the team and more about the deed. And so I hope that makes sense. I'm quick to praise, but you know, I'm more inclined to say, Hey, hey man, great job or hey man, great job with that. I'm also equally quick to debrief myself and to bring them into that debrief as well. Man, I screwed that up.

I could have done that better. Here's a, here's something for you to think about too. And I think how we set that tone in feedback regarding your question on on on praise coming to me. I think grace is an important component of leadership. And I'm always grateful and gracious about it. But I never let it I never let it go to my head. I don't mean to sort of back to your initial point about Stoics being unemotional. I'm grateful and I'm humbled by it, but it's not about me. I really believe as a servant leader

that any successes that I've had in my career or in my life are direct reflections of those leaders or subordinate leaders that have invested in me. And therefore, I think I owe it to them to be thoughtful in how I receive that and to reflect that back towards those subordinate leaders or other leaders or mentors that I've had? Well, I think about that because like, let's say you're someone who is selfless and a servant leader and you're like, well, praise is an important to me. It doesn't do anything for me. Maybe it even makes me a little uncomfortable.

It can be easy to make this assumption that other people are all wired the same way, right? And you realize, oh, no, like they need to be recognized, right? They need this. And I think understanding that it's called self-discipline, not the other way around. Like the standard you hold yourself to the stoic say, is not fair or reasonable or a good idea to just assume other people are on the same wavelength

to same priorities. That's where I got to be really in tune with EQ and I got to really read humans well. And the limbic brain is such a gift in terms of understanding human dynamics and body language and stuff like that. And each individual, each of us is so unique that you have to take the time as a leader to get to know how folks work. And yeah, what motivates this person

versus that person, somebody, somebody's about responsibility and recognition, somebody's about money, somebody's about solving good problems. And you know, some people just shouldn't be on the team and you've got to figure that out. Absolutely. Yeah. Let me see if there's any last questions but this has been absolutely amazing. Oh I guess the last question is so talking about routine because I think it's really powerful big part of the stoic mindset and certainly though something I was thinking about the last two

weeks was on the road. How do you think about routine and good habits when you're deployed, when your schedule is not under your control the way that you might, it might be when you're at home or you're at the office. I mean, it's a great question and thanks Ryan. I appreciate I can see the chat there on the margins. I think it's about being committed to finding a way and a rhythm that works for you. And it won't look perfect and it may take some time to stabilize. But when you're overseas or on a deployment

or on a work trip or whatever, I think you need to thoughtfully sit down. I do this even before I go on the trip. Where is there a gym? What do I think these days are gonna be like? And I try to get ahead of this so that when I land in whatever place I'm gonna be at, I'm set up for success right off the bat.

And I look forward to it. And I do the same thing with my team. And so, you know, there's, and if your schedule's moving around, I think you just got to stay flexible and agile and up on the balls of your feet. But what I will tell you is, is when you master that,

especially in a dynamic environment where the schedule's changing, but you find a way to get your reading in or get your workouts in, or even if they're not as effective or the same as they are when you're at home. The fact that you've done them will bring you strength and power and comfort that you almost can't measure. I mean, because you'll feel like you've accomplished

something for the day. You feel like you stayed close to what you know is your center post of how you set up your life. And I think being agile and flexible is an important component to this, especially when you're on the road. Now, I mean, I don't know what's work, but I can always find a place to work out.

I can do the stairs in a hotel. I can do it in my hotel room, my TRX, whatever. I can always find a way to make it work. Yeah, I think one of the things that I've come to think about, especially having kids or young kids sort of throw it out, is if routine to you is the order that you do things and the place that you do things, you're very vulnerable, right? Because everything has to go right. If you think about it instead, like these are the daily rituals that I practice, then you can shuffle the order around.

Do you know what I mean? It's like, hey, I wake up early. Okay, that's more or less a new, but I work out, I take a walk, I do some reading. You can shuffle those around based on the particulars of where you happen to be. Like when I travel, I run in the morning, when I'm at home, I tend to run in the afternoon because I have more freedom at home than I do on the road, right? And, and, and, and you know, I'm not worried about hotel checkout times and, you know, where am I going to get a shower after. So I think if you can figure out, to me, obviously, if your day is chaos, you've got to figure out a routine.

That's step one. But once you've figured out a routine, the next level of this is that flexibility, or Robert Green talks about formlessness, the flexibility to be able to make it work in any and all environments is really important. Yeah, I'm laughing because no plan survives first contact with the enemy Murphy or a four and a two year old

or five and three, right? So no way, no how, but good on you guys, you and your wife for trying to keep some structure going. Well, general, this was absolutely amazing. and your wife for trying to keep some structure going. Well, general, this was absolutely amazing. And I can't wait to see you back in Texas soon. And thank you for your service and for taking the time here to teach us about leadership. I know it made a big difference for everyone,

certainly me as well. And I appreciate it, I'm so glad we met. Yeah, same here. And I'm passionately invested in this. And if anybody has any follow-on questions, you can find me through the Daily Stoic or on social and I'm happy to answer them. I want to thank everybody and you and your team

Ryan for the opportunity to spend some time with you. You're the best. All right, man. Talk soon. All right, cheers everybody. All right. Thank you. Yeah. Hey, prime members, you can listen to the daily stoic early and add free on Amazon music.

Download the Amazon music app today, or you can listen early and add free with Wondering Plus in Apple podcasts. on music app today, or you can listen early and add free with Wondery Plus in Apple podcasts.