In Episode 104 of Veteran Led, John s. Berry hosts Lieutenant Colonel Retired Oakland McCulloch, renowned leadership expert and author of Your Leadership Legacy: Becoming the Leader You Were Meant to Be.
Oak dives deep into the timeless principles of leadership, sharing how trust, service, and adaptability can elevate teams and organizations. From lessons learned in the military to adapting those skills in civilian life, this episode is packed with actionable advice for anyone looking to lead with integrity and purpose.
What you’ll learn in this episode:
Whether you’re leading a team or striving to grow personally, this conversation will inspire and equip you to leave a lasting leadership legacy.
Explore Resources from the Episode:
Leadership is about people and trust. People aren’t going to trust you if they don’t get to know you, and you can’t trust somebody else if you don’t get to know them. So you got to get out of your office. You got to get out where the people are that you’re leading and actually get to know them down where they’re working. I promise you, you call somebody into your office and you ask them a question, you are going to get a different answer than if you ask that same question down where they’re working. Because once you call them to your office, it’s like going to the principal’s office. Now I’m in trouble. So get out of your office.
Welcome to Veteran Led. Today’s guest is Lieutenant Colonel Retired Oakland McCulloch, leadership expert and author of Your Leadership Legacy: Becoming the Leader You Were Meant to Be. Welcome to the show, Oak.
Yeah. Well, thanks, John. I appreciate you having me on the show.
So we talk to Veterans here about building bigger, better futures after service. And I’m going to hit you with the hardest question I have, because this is where a lot of Veterans struggle. How do I become an even better leader after military service?
Yeah, I think there’s two things that you really need to be able to do. Number one is you got to reflect back on what it was that made you successful in the military, because I promise you that will make you successful in the civilian world. You may have to change some things, how you do some things, but the principles will all be the same. I think the second thing is that you got to be willing to put your ego aside. I talk to a lot of Veterans who come out, a lieutenant colonel, master sergeant, Sergeant Major, Colonel, and they expect immediately that they’re going to get the same respect that they got when they were in the military. In most of the civilian world, they don’t even know a colonel is. They don’t know what a sergeant major is or any rank in the army, because a lot of them had never even met a soldier. Sad, but true. And so you got to be able to put your ego aside and say, yeah, I got to start earning that respect like I did when I was in the military. And I think if you could do those two things.
The reflection piece, I think, is huge. Just reflect back on those things that made you successful. The little things that made you successful, because those are the things that are going to help you earn that respect with the people that you’re now going to lead.
Let me tell you about some of the worst leadership advice I got as a young second lieutenant. You were an infantry lieutenant. You know exactly what I’m talking about. I was promised to become the Alpha Company XO or the Scout Platoon Leader, but instead, I became the Support Platoon Leader. And when you’re the Support Platoon Leader, they send all the ash and trash from battalion to you to go to your ammo section and whatnot. And I was getting all these dirt bags. We’re going to the National Training Center, and I went to battalion Sergeant Major. I said, Hey, Sergeant Major, look. I said, There’s a problem here. I got to support the entire battalion, and I’m getting all the dirt bags. I knew they were dirt bags when I was in the line unit, so I knew what was going on. And he said, Lieutenant, they had high enough ASVAB scores. They’re physically fit enough. They were accepted by the army. If you cannot train them to standard, it is a leadership failure on your part. What do you say to that, Oak?
Yeah, I think that’s… We all have those soldiers that you just, no matter what you do, you can’t get them trained. But my philosophy, and I took over some platoons and organizations that were broken, and I had to fix them. That was why I was put there. The way I always did it was I started small. I said, Okay, let me give them something that I know they can do. And once we get to that point and we accomplish that, then I took it a step higher, and I just kept adding a step every time that they were successful. Every time they were successful, we celebrated that success. I made a big deal about it. Every time they weren’t successful, I sat everybody down and said, Okay, again, the reflection piece in the army, you call it an AAR, it doesn’t matter what you call it. I said, Okay, what were we supposed to do? What did we do? And how can we get better at it? No blame, not blaming anybody. Let’s just figure out how to get better. And I actually, whenever possible, I would throw it out there and let them suggest how we need to get better.
And when it made sense, we would use that. Here’s what I found when I did that. Not only did I gain a little bit of respect with them because I asked them their opinion. But then if I use some of their opinions, then no longer is it Lieutenant Colonel McCulloch’s idea or Lieutenant McCulloch’s idea. It’s our idea. Now they got some skin in the game. Now they should want to work a little bit harder to make sure that it works because they had some input into it. I think those two things. I think if you can do those, start small, build on the successes that you know they can get, then start building on it and try to use some of their opinions. I think you will find that you will get to those people that maybe you wouldn’t necessarily get to, but were the ones that you could save. Again, you’re not going to get to everybody.
Yeah. The old saying goes, Christ couldn’t save them all, neither can you. But I like what you said is it I think you can find sometimes in their input or their feedback that there are pieces that you can implement, and maybe at no cost to your vision or to your mission. And you may say, Well, this may be a small piece. I don’t know that it helps, but it doesn’t hurt, and they’re going to own it. Is that what you’re saying?
Yeah, absolutely. You can’t ever sacrifice your values, your morals, your standards. But the analogy I always use when I say that we should use somebody else’s opinion and their knowledge, their skills, their abilities, and I always use the analogy, the number nine. If we got to get to the number nine, why do I care how we get there? Seven plus two is nine, but so is eight plus one, and five plus four, and six plus three. Don’t care how we get there. We just got to get to the number nine. And I think if we look at it that way, you’ll see that things don’t always have to be done your way. They can be done somebody else’s way. And I learned that lesson as a young lieutenant with my first platoon sergeant. Here, I was a 24-year-old lieutenant taking over my first platoon. My platoon sergeant had been in the army for 23 years. Why would I not take some advice from a man like that? But again, got to be able to put your ego aside, and a lot of lieutenants can’t do that. And so they don’t use all that skill, knowledge, and ability that their soldiers have or whatever organization they enter after they leave the army.
There’s a whole lot of skills, knowledge, and abilities in there that you don’t have. Be willing to put your ego aside and use those people that have those skills.
Yeah, absolutely. I read a book by a Veteran named Dan Sullivan, and he wrote a book called Who Not How. And what I took away from that book was you find the right person. You don’t need to know how to do it. They know how to do it, but you just got to find the right person. I think of the army mission statement. It never tells us how. It’s who does what, no later than, when, vicinity of where, in order to what or why. And so you get the who, what, when, where, why, but they never give us the how in the mission statement, and that’s for the leaders to figure out. But the mission statement always starts off with who. Who are you going to choose? Is it going to be Alpha Company, Bravo Company? Who are you going to put in that position to be your main effort? Who’s going to be the support effort? But it seems that that’s the biggest question sometimes as leaders is figuring out who is the most qualified person to solve the problem for us. And I like your… Going back to being that second lieutenant where you realize your platoon sergeant is the who, who has the experience and can probably guide you.
But being that new lieutenant. And I think when we come out of the military, it’s like being a lieutenant all over again. How do you find that platoon sergeant? How do you know whether that senior person is going to be that great platoon sergeant who’s going to take care of you, take you under his wing, or whether this is just some burned-out old crusty dude who shouldn’t even be in the company anymore? How do you know who to trust?
Yeah. Well, I think that’s a great question. I always tell people, you got to remember, leadership is about people and trust. And so people aren’t going to trust you if they don’t get to know you, and you can’t trust somebody else if you don’t get to know them. You got to get out of your office. You got to get out where the people are that you’re leading and actually get to know them. Ask them questions. Actually, spend time with them down where they’re working. I promise you, you call somebody into your office and you ask them a question, you are going to get a different answer than if you ask that same question down where they’re working. Because once you call them to your office, it’s like going to the principal’s office. Now I’m in trouble. So get out of your office. I had a boss who retired a three-star general, a good mentor of mine. And he told me one time, he said, Oak, I don’t care how high up in the organization you get. Never, ever, ever, ever, turn down a chance to go get your own cup of coffee.
He said, Two things happen when you do that. He said, Number one, you show everybody that works for you that you’re no better than they are. You have to go get your own cup of coffee just like they do. Number two, if you do that, hopefully you got two or three different ways to get to the coffee pot and back to your office. And along the way, you stop and talk to people and get to know them and let them get to know you. In the last 16 years, my last three years were on active duty when I ran my own Army ROTC program, and the last 13 years, when I was a recruiter for one of the Army ROTC programs here in Daytona, I had my hand in commissioning over 600 lieutenants, and I told every single one of them before they got commissioned, that your goal should be that every day you get out of your office, you go find one person that you’re leading, and you find out one new thing about them. Not about the work. You can find that out throughout the day, whatever. But make it a point to find one person, find one new thing about them.
What’s their spouse’s name? What’s their kid’s name? What sports do their kids play? What’s their hobbies? What do they like? What don’t they like? Get to know them. Here’s the key. You got to let them get to know you as well. And some leaders don’t want to do that. And I got it. You got to keep the leader-led relationship. That doesn’t mean you can’t get to know the people that you’re leading. You have to. That’s the only way you’re going to build trust.
That’s a great point. Where do you draw the line in the civilian world between getting to know someone and what we call in the military is fraternization. Because as you know, one of the challenges as a leader, especially in a civilian organization, is once you start spending a lot of time with one key player, another key player might feel left out. Now, I’ll just tell you, for me, I look for my A players, and I spend as much time with them as I can because I figure if I hang out with excellence, it’s going to draw more excellence. People are going to say, Oh, I want to hang out there. I said, Be that good because everybody gets my love, but only my A players get my time. So I’m just wondering, I’m wondering your thoughts on that. How do you do that where you’re connecting with everybody, but you’re making sure you’re spending your time where it’s going to have the most impact for the organization with your best people?
Well, in the army, we always said reinforce success. I think that’s what you’re talking about. That works just as well in the civilian world as it does in the military. And you’re exactly right. You get to know everybody. You take care of everybody. But the people that you know that you can rely on, that you know are going to get the job done, that’s going to take care of not only you, but the organization. That’s where you got to put your main effort, and that’s where you got to spend the most of your time. But I think the only way you’re going to figure out who people are is to get to know people. And by trial and error, you give somebody something and you figure out they can’t do what you’re asking them to do. Then it’s up to you to start training that person so that eventually they can do what you’re asking them to do. Or get rid of them, one of the two. Sometimes it comes to that. But I think that the key is you got to get to know people. As I go around to companies and I talk to companies, lots of times I get people who say, Well, I gave this job to this person, and they didn’t do a good job.
I said, Was that the right person to give that job to? I said, How do you know it was? Because I’ll bet you that the person sitting right next to them would have loved to have had that job and probably could have done it just as well, if not better than the person. The only way you’re going to know that is to get to know the people and figure out what their strengths are, what their weaknesses are, what they like, what they don’t like. If you don’t figure that out, you’re going to be given people the wrong job all the time.
Yeah. And I found in the military, you know what? People follow orders. At the end of the day, if you lead, they will follow, and you can set the example, and you’re probably going to be okay. But in the civilian world, you can only lead the willing.
Absolutely. I agree 100%. And I ran into that at the food bank when I left the army and that was my first job out of the army. There were some people in that organization who had been there for a long time who just had no… All they were there was to draw a paycheck. That’s it. One of the stipulations when I took that job was, I was the associate director, I wasn’t the director. One of the stipulations was that I had all control over hiring and firing. I fired some people within the first six months I was there, and hired a bunch of people that some of them are still there today doing a great job for that organization. You got to figure that out. There are people who aren’t going to play the game, who aren’t going to come to the table and are just there to draw their paycheck and go home.
Absolutely. Now, I read one thing in your book, and you said, Look, leadership is leadership, and I can run a hospital. Now, I really want to dig into this because my position is that generally when you’re around, say, lawyers or doctors, they’re technicians, engineers, they’re technicians. And so they’re not necessarily going to be leaders or receptive to the same type of leadership that maybe we would see in the military where everyone’s a leader, right? We have a chain of command. We know that if you don’t move up, you move out. And so leadership is just part of the culture. But as we move into things like hospitals, law firms, things like this, leadership becomes more difficult because you’re dealing with technicians and people who have, I think, a different outlook on life. So I’m curious, Oak, you’re going to go in and run a hospital and you realize that you’re going to be dealing with a lot of technicians now. How do you adapt your leadership style or strategy, or do you keep it all the same?
No, I think the principles remain the same, because I do believe leadership is leadership. What makes you a good leader is going to make you a good leader anywhere. How you deal with the new set of people that you’re going to be leading certainly has to change. I’m not going to talk to somebody like I did when I was talking to a bunch of infantry guys. At the food bank, I couldn’t talk that way. I had to figure it out. But I think the key, and you’re absolutely right, there are technical things that you don’t know, and that may not be your expertise. But I would tell you, put your ego… Put your ego aside. Go find a person in that organization. Because a hospital, just like the military, just like any organization, it’s divided into sections, and there’s leaders in each one of those sections. So figure out the leader that you got to get on your side to help lead the people that they know, and they know how to lead those people because they’re a technician just like they are. So use those people. Teach the culture that you want, establish the culture you want, to figure out the standards that you got to train people to.
But the principles remain the same. I believe that. But you do have to change how you communicate them and how you… You might even have to change a little bit of how you interact with people, but the leadership piece of it should be the same.
Now, one thing that you say is leadership is about service. And certainly, it is. At the end of the day, we’re all servant leaders. We all want the team to be successful, which means we have to invert the org chart. We’re on the bottom trying to hold people up and help them do great things. But that being said, where I have struggled is, especially in organizations filled with lawyers or technicians or bureaucrats or politicians, it seems like they want leadership to be about consensus. And I’ve always I’ve always found that getting consensus doesn’t always serve the organization. I’ve always believed that leadership is about results. I’d love to hear your thought. Is leadership about consensus, results, service? In one word, what is leadership? I know there’s a lot of definitions you talk about them in the book, but if you could say it’s a result, it’s consensus, it’s service, what would it be?
I think it’s service, but I would say it this way. In the army, we had the saying, Mission first, people always. And that’s my philosophy. I got to accomplish what I got to accomplish because in the real world, results do matter. Fantasy land where everybody’s a winner and everybody gets a trophy, maybe not. But in the real world, results matter. So we got to get the result. But if you’re a servant leader, then I think you also take into account how getting that result is going to affect the people that you have the privilege to lead. And it is a privilege to be the leader. I think too many leaders today have forgotten that. I believe it’s about selfless service, with the caveat that you got to accomplish the mission. That’s the whole reason you are a leader, is to get something done. The servant leader piece of it is how you get that done. But you got to, and in my opinion, that’s the right way to do it, taking care of the people. Because if you take care of them, they’re going to take care of you. You make them better, they’re going to make the organization better.
And in the end, you’re going to get what you want. I always used to tell the young lieutenants and cadets getting ready to be lieutenants, leadership is not about you, and yet it’s all about you. I’d always have one of them say, Well, Colonel McCulloch, how can it not be about me and all about me. And I said, It’s not about the privilege you get or the titles that you get or that you get better pay. Those are nice, and leaders get those things. But if that’s the only reason you want to be the leader, please go do something else because you’re never going to be a good one. It’s all about you and how you treat and empower the people that you have the privilege to lead, to make them better. I’d always have somebody say, But I want my next promotion. I want my next pay raise. I said, If you do this right, you’re going to get it by making them better, and they’ll make the organization better, which you will get credit for, and you’ll get your next pay raise and your next promotion, but you get it for the right reason, not because you were greedy, but because you helped other people become better not only at work, but hopefully even better people.
Outstanding. Now, this is my favorite part, especially because there’s some rich examples in your book, the After-Action Review. Three examples of great leadership that you’ve either experienced or read about or heard about, and then three examples of horrible leadership. Don’t have to name names. So let’s start with the good.
Yeah, well, I could connect two of those together, horrible and good. I was in a S3 air for a CAV squadron. So I was a senior first lieutenant. And we had a major who was the operations officer who was not married. And his rule was, if he was in the office, you were in the office. It didn’t matter if you didn’t have anything to do. If he was in the office, you had to be in the office. We’d stick around there till 6:30, 7, 8:00 at night just doing busy work because we were there. We had to be there. We didn’t have a choice, for no reason. We’d work on operations orders that weren’t due for another month or something. It was just busy work. He left. The new major came in. The day he came in, I’m sitting there in the office at five o’clock, and I’m working on an op order that’s due three weeks from now. He sticks his head around the corner and he says, Oak, what are you doing? I said, Well, I’m working on this operations order, sir. And he said, Is it due tomorrow? And I said, No, sir.
He said, Then go home. You want to talk about morale going through the roof like that? I mean, all of us left at five o’clock. He said, If I need you here after five o’clock, I will tell you that I need you. Otherwise, I expect you to leave and go home at five o’clock and do whatever it is you do at home, and I don’t want to know what that is. And I think those two, good and bad. Another good one that I had was I had a boss who would actually come in, sit down and say, Okay, not just with me, with the other captains and especially platoon leaders, and would say, This is the problem we have, or this is the decision we have to make. Give me some ideas. We’d throw them out there to him. He may not use your idea. So I adapted this method. When I could, when somebody’s shooting at you, you don’t have time to call everybody together and get ideas. But when I could, I would call everybody together just like he did. What generally happened with him, and I found it happened with me, is sometimes I would use somebody’s great idea.
Sometimes I wouldn’t use any of their ideas. Sometimes I would use a little bit of somebody’s idea and a little bit of my idea. But again, once you’ve done that, you build that respect, you build that trust, and they got skin in the game. They had a part in it. Even if you didn’t use their idea this time, you might use it next time. And so I adapted that. The third thing that a great leader did that I saw that I adapted immediately is the getting to know people, how to get to know people. I was a captain at the National Training Center, and I was an OC. And so I was… The new Lieutenant colonel came in, and I came in just about the same time. One day, I was walking past him in the hallway, and he said, Oak, how are you doing? I said, Fine. Fine, sir, and I kept walking. He goes, No, no, no, no. He said, Come here. How are you doing? I want to know. How’s the transition from Fort Knox to Fort Irwin going? How’s housing? Is that going okay? You got all your stuff.
What’s your wife’s name? How’s she doing? You got any kids? He spent probably, I don’t know, 5, 10 minutes with me there just asking me some questions, getting to know me a little bit. And I thought I was special. A couple of days later, I saw him do it to another captain right outside in the hallway. But I was a captain then. I was, I don’t know, 32, 33 years old, so 30 years ago. And I still remember that like it was yesterday. So I started doing that from that point on. I make it a point to stop and talk to people and actually listen to what they’re saying and make them actually talk, not just, Fine, how are you? And move on. Those were the three good ones. I had a boss who… We were on deployment, and I won’t say where, because then everybody would know who he is. Christmas Day, freezing cold outside. We got platoons everywhere, spread across the AO doing checkpoints and guard points and stuff like that. Christmas Day, I got up, made a phone call to my wife and kids, 6:00 in the morning, and then I left the office, and I went around, and I went to every single one of those outposts or guard posts, or whoever was outside that wire.
That boss I had never left the office that day. You think those soldiers didn’t realize that he didn’t come out to see them that day? You better believe they did. I think that’s probably one of the worst examples I’ve ever seen of leadership.
Wow. Yeah. Okay. Any additional ones?
Certainly, I have. I’m just trying to remember.
I think there are always the cheap lessons when you learn from somebody else’s bad leadership and say, That’s not who I want to be.
That’s right. I tell people all the time, you can learn just as much from somebody who does something poorly as you can from somebody who does something well. What you learn is that you will never do that. I’m sure you, and most of the people listening to this podcast have been in a formation sometime and had a CEO or a senior NCO or somebody say something, and the hair on the back of your neck stands up and you’re like, Yeah, I will never do that. You learn from those things as long as you actually learn from them and remember them and don’t do them again. Those are probably the two bad examples that I want to throw out there.
Well, thank you so much for sharing those examples. Of course, for readers who want to learn more, they can find your book, Your Leadership Legacy: Becoming the Leader You Were Meant to Be. I know they can find it on Amazon, and you have some other books as well. What are those other books, and where can those books be found, Oak?
Yeah, that’s my only, I guess, technically my book. My master’s thesis from when I was in college is out there, and it’s the Decisiveness of Israeli Small-Unit Leadership on the Golan Heights in the 1973 Yom Kippur War, and that’s out on Amazon as well. Then I’m working on my second book now, and it’s going to be on success, the things that you have to do to give yourself a chance to be successful. Anybody who stands up and tells you, Do these 10 things, and I guarantee you will be successful, run away from those people. There are no guarantees. There are things that can help you increase your possibility of being successful, but there are no guarantees.
Yeah, I’ve learned that you can deserve to be successful by doing all the right things, but that doesn’t mean that you’re going to be successful, but you can control what you deserve. If you’ve done the work and you’ve done the right things, then so long as it happens, then you’ll feel good about it. But if it doesn’t, you know that you did everything you could.
If it doesn’t, then you try something else.
Absolutely.
One of the best talks I ever heard was General Hal Moore. He stuck with me and sticks with me still today. One of the things he said that I absolutely agree with and that I think I embody as well is, Life is not like baseball. It’s not three strikes and you’re out. If you try something and it doesn’t work, try something else. If that doesn’t work, try something else, and just keep trying until it works. That’s part of being successful is that motivation, that drive that self-discipline to do those things that you know that you need to do. Even if it didn’t work this time, it might work next time. If it doesn’t, you tweak it a little bit and try something else.
Perseverance. Outstanding. Oak, for Veterans that want to learn more about you or maybe even get a hold of you, where can they find Lieutenant Cronen Retired Oakland McCulloch?
Yeah, so I have a website, and on that website, it has the links to all my social media, which is where we connected, LinkedIn Then mainly is what I use, but I’m on all the social media. Some of my stuff is on YouTube. I’ve got an Instagram. You can go there. Also on that website, it has my cell phone number and my email address. Always happy to hop on a Zoom meeting or take a phone call from somebody to either just connect with somebody or to help them through a problem, or if they want me to come speak at their conference or association or whatever it is that you’re doing, I’d love to connect with some people and talk. I spend a lot of my day just on YouTube or on Zoom talking to people, just getting to know them. You may not ever be able to help me, and I might not ever be able to help you, but you never know. Somewhere down the road, we might be able to help each other.
Outstanding. That’s what I found so great about the Veteran community. We’ll put the URL in the show notes, but if you have it, what is the URL for your website?
Yeah, www.ltcoakmcculloch.com.
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