The Wealth Cast Ep 23 - Kevin Cheesebrough - Leadership Under Any Circumstance

On Episode 23 of The Wealth Cast, Chas hosts former nuclear submarine commander Kevin Cheesebrough, Captain USN (Ret). Kevin is now a Professional Certified Coach with the International Coach Federation serving as an executive leadership coach and mentor. Chas and Kevin discuss how the skills Kevin developed in the Navy transferred into civilian life, from emotional intelligence, to managing data, to how important it is for leaders to trust their instincts, and more.

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Hello, and welcome to The Wealth Cast. I’m your host, Charles Boinske. On this podcast, we bring you the information that you need to know in order to be a good steward of your wealth, reach your goals and improve society. On today’s podcast, I’m thrilled to have Kevin Cheesebrough as my guest. Kevin is a friend of mine and former commander of a nuclear submarine, as well as serving in his current role as leadership coach for executives in business and in industry. On one programming note, Kevin and I, as I mentioned, are friends, and many of my friends refer to me by my middle name, which is Philip. This is an artifact of being a “junior,” and my mother not wanting to have two Charleses in the house at the same time. So I hope you enjoy the show. Thanks again for joining us.

Kevin, welcome to the podcast. I’m so glad to have you here. And appreciate you spending some time with us today.

Well, Phil, first, it’s a real honor to be on your podcast. And you know, just sharing some of my experiences through my times in Navy leadership, especially on a submarine. So yeah, real, real honor to be here.

Well, thank you, and I’ve been looking forward to this conversation. You don’t often get a chance to have a conversation about leadership with someone who’s captained a nuclear submarine and experienced all the stresses that must go with that in terms of leadership responsibility.

So you were kind enough to talk to me earlier about some things that you learned during your experience in the Navy, and I thought we could tick through a few of those, because I think the listeners will find that really helpful. So why don’t we just start sort of start at the top and, and work through the list?

Hey, it sounds like a plan!

All right, simple is better!

One of the things that you mentioned in our last conversation was the importance of, for a leader, to train their relief and develop their relief. And could you talk about that for a minute, because I think that’s really important.

Well, one of the premises from the very start, I mean, from whenever I was a junior officer on a submarine, to the point where I was now commanding officer, I learned from the bottom up that my superiors were there and really concerned about how I was developing as a leader. And as I went up through the, you know, through the ranks becoming engineering officer of a nuclear submarine and had about six division officers and about 60 people below me, you realize that the most important thing you want to do is walk off that ship and have people trained well, to go off and continue on that legacy of leadership, and being able to continue to lead a complex piece of equipment.

So as you see, I was particular. It was interesting, because I sat there and I’m thinking, “These young junior officers 20 years from now, one of them is going to be a CO.” And you had to have that expectation, knowledge that, you know, I got to really be on-game to make sure they develop in the best way possible to be the best commanding officer, and it turned out two of them did end up commanding a nuclear submarine at one point.

Well, job well done!

Well, you know, it was just, it was one of those, like, it’s always you sit back and say “I’m not sure how much I contributed, but obviously, and they had successful tours, you know, no ships running around, they didn’t get relieved for cause or anything!”


So I must have done something right. And it was rather interesting. Whenever I entered the civilian world, how there was almost even that fear of trainee relief at times, you know, that concern that, “Well, if I train them, they’re gonna take my job.” You know, it just seemed to be like number 10, you know, on the list of tending to worry about. So I’ve used it even in my leadership. Coaching is, “You know, what are you doing to train your relief?”

One of the things I thought was interesting is that you mentioned previously in our previous conversation about the Navy creating what I sort of, as a lay person, would think are very short tours of duty, you know, a year and a half or two years on a submarine as a CO and then move to the next or new next assignment. There must be method to that madness from my perspective. But that sounds like that gave you the opportunity to iterate that process a number of times during your career and I wondered what you learned through those iterations.

The Normal rotation for a submarine officer is three years on a ship, two years off. Three years is really for the family mental health at times, because you can only be gone so long, and then you just get burned out. And not just the active duty person—the family puts on a lot of stress. I mean, Navy families really put on a lot of stress when they’re gone.

So that cycle is there to give that opportunity, and it’s also for growth. You know, it’s also the ability to go from being a junior officer ashore, and then you come back as a department head, and in my case, I was Engineering Officer of a nuclear submarine, had about 55 people that, you know, that I worked with. I was responsible for everything from the nuclear reactor to the ice cream machine, and sometimes the ice cream machine had priority.


Yeah, and so that gives you the opportunity then to go and go to shore go back as XO. And the short tours are generally also instructive themselves, you know. They add to that development process you go through, and even in a short tour, it’s where I got my master’s degree, and I was able to, then you have time for that. So it’s designed to go do that. But it’s all development. I mean, you go off to be, you know, go be CO without being XO, and XO is standing back behind, it’s kind of being the Chief of Staff, or we used to call him the head buttkicker in some respects. You know, the good cop, bad cop. But the XO, you know, but learning how to even manage the complexity before you then had to stand back at that higher level as CO and kind of know what all the tweaks are that are going on in leading that complexity.

So it’s all developmental, and you know, you get to be CO, I think it was what 38 whenever I got to be CO? Which whenever I look back on it, it’s like, well, 38, you’re in charge of a $2 billion submarine, and 140 people, it’s like, “Wow, that’s pretty neat. They really trusted me with a lot!”

That sounds like a stressful situation to me!

Well, you know, the aspect about that, though, is you learn so much as you go through it. Technically you’re solid, but you’re still there as the person who is—there’s nobody else to turn around and look at. Whenever you’re out there and submerged and you’re in those you know, where you can’t communicate with anybody, you’re the person that has to make decisions. And that’s just a little bit different at times than being able to pick up the phone and text somebody or text somebody these days and get backup.

Sure, I can’t imagine!

One of the things that we talked about was, you know, and you alluded to it earlier, being three years on a ship with limited contact with your family. What that means on the other side is you really get to know your crewmates really well. You had mentioned in one of our conversations about developing emotional intelligence, living together with these folks for you know, 24/7 underwater in cramped quarters. What, sort of, did you learn about human nature and emotional intelligence through that experience?

Well, you know, it’s interesting, because it was probably about eight, nine years ago, is whenever I first was introduced into the concept of emotional intelligence, and I looked at it and I said, “Well, I think we were really doing a lot of this whenever we were in that environment of, you know, being submerged for two and a half months,” and realized it was more formalizing the concepts that that were there as far as self awareness, self management, understanding other people’s emotions, and how do you manage relationships, or self awareness, self management, social awareness, and relationship management.

And I look back on it, and I realize we had to do that from the very beginning. When you’re imagining being with people 24/7, three meals a day, watching movies, celebrating Christmas, Easter holidays, you really have to learn how to separate your emotions, to not really create chaos. When we’re here just feeling in that moment of, “I’m just, you know, upset or whatever,” you really had to learn, “Okay, there’s a time to put people under stress,” and then there was that time where, “Okay, I need to really be able to self manage myself,” and “Okay, we’re going to sit down at dinner and we’re not going to talk business. We’re just going to talk about ‘Hey, what movie do you want to watch?’” Or you know, “what Liberty port we’re going to,” and you know, “where we hope to go visit,” and being able to basically manage those emotions and then step back.

To compartmentalize those—

—Yeah, a lot of it’s compartmentalization, and then I think even in the whole issue of emotional intelligence, is really managing your emotional energy. And we really had to—I call it the emotional gas tank. There’s only so much emotional energy in the gas tank, and you had to really siphon it out a little bit at a time knowing that, okay, you know, in a moment, you know, when we’re out there, you know, in the Cold War when you’re out there looking for the bad guys, there are a lot of moments of boredom followed by a lot of moments of kind of panic. So you had to, you had to save up that emotional energy to be able to be there.

But you also had to be really aware of that social awareness of the people you’re leading. And just noticing, because they’re usually positive indicators that “something’s different here,” and just looking at somebody’s affect, and being able to have that, you know, that empathic connection with them to say, “Okay, well, I’m really sensing some, some anxiety, scariness here,” and which generally led up even to that aspect of asking the right question: “What’s up, I see that, you know, you don’t feel confident about going to periscope depth right now, you know, what’s your sense?”

You know, it really was an important element, which now I include, in most of my coaching. I always include an emotional intelligence assessment, because it’s really important for all leaders to have that ability to be self aware, and then self manage, which are the two biggest keys to be able to do that.

That’s helpful. You mentioned just a moment ago, or you alluded to, the role of intuition in your job as CO. And as a lay person, you picture—and I’ve never been on a nuclear submarine, so I’m imagining all this, of course—but you imagine electronics galore, lots of data, a tremendous amount of input from your crew, about where you’re headed, and what’s going on around you. But, you know, I thought it was really interesting, that intuition still plays a role.

Oh, absolutely. And it’s interesting, my Navy career, we went from analog fire control systems, to these super high speed computer systems for fire control, and sonar, things of that nature. But you still had to use your intuition to determine, “Does this make sense? What am I sensing about this?” And it was still humans that are managing these devices, and just using the intuition to sense, “Do I really feel confidence, or am I sensing a hesitation here?” Even though whatever that machine may be, or that device, the digital display is telling you there. The old question, “Does it make sense? Does it make sense?”

Yeah, I think the immediate reaction for most people is, it’s hard to imagine a situation where someone has more data than a submarine commander, right? So even in that role, you’re forced, or for the good of the crew, and for the good of the mission, or however you want to phrase it, you’re better off using some intuition / gut feel, to help, you know, frame your decision making a little bit. And I thought that was really interesting, because in business, we have that all the time, right? We have less data than you had, and yet, sometimes folks are uncomfortable, really leaning forward with their intuition. I wonder if you see that in your coaching program?

Well, I hear a lot of the term “dashboard” a lot. You know, “My dashboard is telling me this,” but my question on this, again, “What is your intuition telling you?” And that is, to me, that is the biggest key is, “What is your intuition telling you about what you’re seeing?” And you know, what if that data is inputted wrong? What does your intuition tell you about that? 

You know, that’s the biggest key, is just being able to step back and look at and say, “Does this make sense?” And, you know, I found that frequently, where I usually had my one or two indicators, I could look at and say, “Okay, these two indicate that truth is here.” Yeah, that’s the key, what indicators do you validate to be able to give you that truth. And, you know, it still came down to, I remember, we had—we even had a manual plot. We had all this digital equipment we had, we kept one manual plot whenever I was, when we had our fire control tracking party. And I’d look at that, and I could tell there’s a manual plot, just a person listening, writing down bearing rates, and ranges and all that, and that was almost my biggest indicator of truth, and it was a manual plot. I had all these other plots, but sometimes, you know, the junior officers would be sitting there telling me, “Hey, you know, we have a good solution on this contact, and I’d look over to this plot and go “There’s no way. There’s no way, so let’s figure this out.”

And sometimes I would set you know, even things like range bearing and speed across line of sight based upon the manual plot. I think even in business in the leadership world, you have to sit back and say, “What am I sensing in this that really brings it?” But don’t get locked into just looking at the data. And I see that a lot. In fact, sometimes it just harasses the daylights out of people below you. You know, you’re looking at data and asking questions before they even had any ability for themselves to see it and figure it out.

Yeah, the ability to step back and see the big picture even you know, as a as a CO of a submarine or the leader of a business has to be a key skill. It has to be. Based on my experience of business, I see that clearly. But it just surprised me that with all the technical data, it’s still true of a submarine commander

I think you had shared, Kevin, a story with me about, I believe it was about coming into a harbor or a port in bad conditions and a decision that you made to just wait, even though the data said you could proceed.

Well, and this was one time where I was stationed at Norfolk on the Finback, which was coming to port but it was just foggy—thick fog. And yeah, we have a radar on a submarine but the radar repeater was not on the bridge where I was the CO just taught on the submarine. You’re relying on a person below trying to tell you, “Okay, the course is good and you know, coming up the channel.”

And one thing in fact, it was one of those fundamentals I learned whenever I was in—before you get to be a CO you go through a six month perspective commanding officers course, and one of the instructors there said, “Don’t ever come up a channel unless you can see the next set of buoys.” Which basically meant you have to rely on seaman’s eye, not on what somebody is telling you on a radar, that “Okay, you need to come left a little bit, whatever,” because that’s how you navigated out of a channel. You can see that the next set of buoys on the right are drawing right, the buoys on the left are drawing left, then life is usually pretty good. 

But you can’t see that, and there was no way I just, you know, I said, “My intuition told me, this is not a good idea to come into here.” So we went back out past 12 miles from land, and just hung out until the fog lifted.


And the interesting thing is, is that even the person I was in charge with, no issue. You know, you’re the person who’s got to make a decision, you have to be able to put eyes on target and see what’s going on, and in most situations in the Navy, nobody questions whenever you say safety was the fundamental. But my intuition was, you know, “I’m not gonna bring the ship up here and risk a nuclear reactor hitting an outbound merchant, you know, sinking in the middle of several shoals.” I mean, that’s not a good idea!

That’s a bad outcome.

Yeah, could ruin a few restaurants on the beach there.

Exactly! Further, you know, the conversation we had—you talked about the importance of taking care of, you’re caring about your people and their families. And I wonder if you could shed some light on that a little bit, because I can imagine that being a lot easier if you’re on a base, where you’re interacting with the families, etc., and getting to know them. But being out to sea for prolonged periods of time has to add complications to that. I just wondered how you went about doing that—the process of caring for people when you’re, you know, stuck on a submarine in the middle of the Atlantic, wherever you were?

Yeah. Well, it took a lot of prep. It started with prep before we left: Prepping families for this and the Navy had a reasonable infrastructure that provided for families in preparing. You know, the sailors and the families, as far as pre, “This is what’s going to look like when you leave, these are the issues that normally come up, how are you going to manage them.” For every sailor, we made sure that their direct deposit that was up, it was going to a bank account that the spouse could get access to, little things like that.

Yeah! Little, but important things. 

Yeah, little but important things. Was there a person that they could then contact and reach out to, you know, as far as, we always had an ombudsman on the ship, who was—and actually, she went to about four weeks of school, where the Navy explained to her just, gave her all the background, just here’s how Navy pay works. Here’s all the things, not that she was going to solve them, but she could direct them to the right person along the way.

And then there was my wife, who was, you know, the CO’s wife had a big responsibility—she generally was the pulse on what’s going on with the wives. If there was an issue going on, they’d call her and, you know, I had times whenever my comms were calling my wife and saying, “We’re thinking about medevacing somebody off because of some issue with, you know, family, and what’s your sense? What’s going on?” And so that was part of it. But a lot of it was just prep, you know, making sure we get paid, to contact somebody, and there was somebody you could go to.

And knowing Susie, I’m sure she did one heck of a job in that role.

I think she was happier to get relieved of command.

I don’t doubt it.

And one of the things you know, in your comments—you talked about sort of separating your, what you call the business of the ship versus the recreation of the ship—whether you’re watching a movie or whatever you did your downtime on, you know, while you’re at sea. How did you foster the ability to have fun on a ship like that, in this, you know, in between the stressful moments? Was there a methodology? Or was it just gut feel?

No, we, you know, we set up different events on weekends. Of course, you always had, on deployment you always had halfway nights, and a halfway night was putting on skits and doing things of that nature. And then we were allowed to take out near beer—you know, there’s no alcohol allowed on submarines, but near beer was allowed. So even after six weeks to two months at sea, I would say even near beer tasted pretty good! 

I bet it did!

So there was that. And of course, depending on where you’re going, if you went below the equator above the Arctic Circle, you had the ceremonies of the blue nose going past the Arctic Circle, and then 55 north, and of course, going past the equator and Shellbacks.

So those are always events that were interesting, that kind of got the crew kind of jazzed. And then there were other things we did just, you know, some ships we had kind of like the underground newspaper, which was usually at least edited by the XO or somebody to make sure there wasn’t—(laughs). And we were in the days before we did too much of the digital world. So you know, nowadays you’d probably worry about finding it on Facebook, right?

Sure. I’m sure that’s true!

So we’d have those and you know, just little things that would, you know—there was always a rivalry on submarines, between the nuclear trained sailors and the non-nukes. And they used to call them the Backenders, and then the navvys and the coners, because they were on the front end of the ship. And they’d have their little rivalries going on, you know, which were within the bounds, but it just kept things a little bit lighter, especially whenever you’re out there, it was sometimes just boring. Before you get into the mission area and/or trying to find whatever the mission is you’re trying to accomplish, it sometimes gets a little boring. So those things help.

I’m sure they did. I wondered, the last thing that you mentioned that I think is certainly worth talking about, is your role as a leader on a ship or in a business, and the unintentional impact you can have, if you’re having a bad day.

Everybody goes through—you know, you’re trying to make sure everyone else is having a great experience, right? As best they can be on a ship, or in a business, or whatever the case may be. And inevitably, you run into rough seas yourself, whether it’s having a bad day, or some news that you didn’t find help for, whatever it might be. What do you recommend to leaders in terms of making sure that if they’re having a bad day, they’re not unduly influencing the rest of the crew, or the team or the firm?

Yeah, that’s one of the fundamentals I learned through sometimes the school of hard knocks. When the head of the—the CO of the ship—is having a bad day, it just resonates throughout the ship. I mean, there’s this tension that would go along, “Hey, the skipper is, you know, yelling at the control room.” And so if he headed back aft, everybody was just kind of in that mode of, “okay, tension.”

So I learned that from the bottom up—what that effect was, and so you only have to be able to monitor yourself. And it was almost developing that awareness of when I am at the trigger moment, and knowing those triggers, and sometimes even sleep deprivation was the trigger, you know? “It’s gonna come quicker here, so you know, maybe it’s time to go take a nap.” And which I learned to do a lot of, because you just, sometimes, you’re stuck for hours, and then you need to take a catnap along the way. But sometimes you need to have that to keep that trigger from coming along.

But it was the awareness of knowing it. Knowing that, “Okay, I need to just go in my stateroom right now, like, you know, it’s safe out here, but if I stay around, I am going to totally affect the concentration of the people around me, and they’re going to get tense, cortisol is gonna flow, and they’re going to lose the clarity they need to have these moments.”

You know, I learned it from the bottom up, but whenever I got there, I realized when I walked out of that stateroom—I won’t call it “Showtime,” but there was a little bit of, you know, “Okay, you know, you’re really challenged right now, but you got to put on the medium-to-happy face to be able to ensure for the good of the ship, the higher moral thing for the ship, to go do that.”

You know, I work a lot with leaders who say “Well, isn’t violating your authentic self?” I said, “Well, authentic self is just not wearing your emotions on your sleeve. I mean, authentic self is just holding yourself to your values and what’s important, and if you have to, if you walk out and yeah, you may feel like this is a really tough day, but you need—the higher value is the effect on the people you’re with—that has to become the authentic person you are: the fact that you’re holding that value of the good and the people.”

In my experience, you probably can do more good for your organization, whether it’s a ship or a firm, by keeping that in mind on the really hard days. The easy days—when it’s easy to be, you know, forward leaning and cheery and everything else, you’re not going to see the value there as much as you would if you can keep people motivated and pursuing the mission when the chips are down.

Well, even when the chips are up, you know, my biggest worry was being gone for six months on a deployment, and you know, you’re coming up the homestretch of Thimble Shoals Channel, and even I’m excited, “Hey, I get to see my family, you know, I’m looking forward to getting the ship tied up and just sometimes just getting a good night’s rest,” and you get that excitement, you have to back off yourself too, to keep everybody else in that perspective of, “Okay. Deep breaths, you know, we got two more hours to go. So far things are going well, we just need to, need to, be able to just keep focused.” And so sometimes you gotta be in tune, you got to throttle it down and manage it with yourself, and with the folks you’re with, so that, you know you continue safety.

Yeah, it sounds like it’s all about being even keeled. You know, when you’re in good and bad situations, just trying to be relatively steady. Sounds like the way to go.

Yeah, it comes back to that emotional intelligence aspect we talked about, you know. You really had to learn how to manage that and manage your triggers, and know when it’s time to, you know, go to the stateroom, and maybe stick your head in the pillow. But don’t do it in front of the troops. 

I understand.

And just “Okay, got it. Yeah, deep breaths. We’re doing good. All right.”

Kevin, this has been really helpful. You know, going from training relief all the way through how to maintain your cool by stepping into the stateroom on occasion, and even taking a nap. I think it’s all been really valuable. And I hope that this can serve as a springboard for further conversation, perhaps down the road. We can reconvene and talk about some of the other experiences that you had and perhaps some of the lessons that you learned that can be shared with the listeners to improve their leadership capabilities, etc. So I just wanted to say thank you so much for spending time with me. I’m looking forward to the next time.

Okay, great! Yeah, it was a real pleasure, and it’s always a pleasure being with ya, Phil. And you know, next time, hopefully it’s around the corner.

We’ll look forward to getting together with you and Susie when the coast is clear.

Great. Great. Well, thanks again for having me.

You’re very welcome. Take care.

Thanks so much for joining Kevin and me today on The Wealth Cast. If you’d like to learn more about Kevin’s services as a leadership coach, please visit the show notes for this podcast, where you’ll find a link to his webpage as well as a complete transcription of this recording. Thanks again for joining us and have a great day.

Kevin Cheesebrough Coach, Inc.


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About Kevin

Portrait of Kevin Cheesebrough

Kevin Cheesebrough, Captain, USN (Retired), came into the coaching profession with significant experience in leadership and career / life transition. Kevin served in the United States Navy Submarine Force for over a quarter century, and the experience he gained in leadership led to a successful tour as Commanding Officer of the Sturgeon-class nuclear submarine USS Finback (SSN-670). During that demanding tour, Kevin and his crew completed three challenging deployments that included operations in the Arctic. He completed his Navy career as the Professor of Naval Science at Pennsylvania State University, where he developed over two hundred midshipmen into future Navy and Marine Corp Officers, and where he also taught leadership and ethics.

Kevin now serves as an executive leadership coach and mentor, certified by the International Coach Federation. He brings over 35 years of leadership in both military and civilian life, along with the experience and knowledge gained throughout that period, to his clients.

Kevin earned a Bachelor’s in Nuclear Engineering from Penn State University in 1976. He completed his Master’s in Management Science through the Rensselaer Polytechnic Institute, while on active duty in 1983. He completed Duquesne University’s Professional Coaching Certification Program in 2014.


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