Thirty Minute Mentors Podcast Transcript: Interview with Lieutenant General Vince Stewart

I recently interviewed Lieutenant General Vince Stewart (USMC, Retired) on my podcast, Thirty Minute Mentors. Here is a transcript of our interview:

Adam: Our guest today is a retired Marine Corps general and was America's highest ranking military intelligence officer. Lieutenant General Vince Stewart spent 38 years in the United States Armed Forces, with his last two roles as director of the DIA and Deputy Commander of the United States Cyber Command. General Stewart, thank you for joining us.

General Stewart: Thanks, Adam. It's great to be with you.

Adam: Great to have you on. Long before you were General Stewart, you were a 13 year old immigrant from Jamaica. How did the experience of immigrating to America and living in the U.S. as an immigrant, shape the trajectory of your career and shape your perspective as a leader?

General Stewart: Yeah, when we came to America, you talk about culture shock. We arrived in New York in October. So first of all, coming from a tropical island to New York City, a large industrial hustle and bustle in the fall, that kind of woke us up very quickly. But we came here because the promise of America was it was the land of opportunity. This is where if you went to work, rolled up your sleeves, and went to work. You could achieve just about anything you want it to. Oh, I didn't understand that. There are some limitations. I didn't understand the challenges. I knew simply that the United States of America had a dream that said, go to work, show up, getting things done. And you got a chance to rise to the top of your profession. And that's the approach that we took; all of us did. I was fortunate enough to get my education paid for. I was fortunate enough to land in a position in the Marine Corps that inspired me to be better than what I ever anticipated for myself. And I believed in that long standing American dream of opportunity for all, so that drove my efforts. And in most cases, it was worked out fairly well.

Adam: What attracted you to the Marine Corps and what are the best leadership lessons you learned from your years as a Marine Corps officer?

General Stewart: You know, I started off being so heavily recruited that I went to Western Illinois University. Western Illinois University is the home of the Fighting Leathernecks and got its name from the Marine Corps, was petitioned by one of the Presidents before rock Hanson, a Marine who was a silver star recipient. So we were the Leathernecks. But I was recruited heavily by the army to join the Army Reserve Officer Training Corps. I knew at some point that I wanted to serve my adopted country. And so I went off to the Army ROTC camp in Fort Knox, Kentucky for about six weeks. I came home for two weeks, went to the Marine Corps platoon leaders course for six weeks and coming out of the platoon leaders course, there was no doubt what I wanted to do because I was challenged every single day of that six weeks. It pushed me harder than I ever was ever pushed. And I wanted to be part of that. I wanted to be a part of something that was challenging and rewarding. Now I'll tell you, after 38 years, Marine Corps taught me more about being a leader, being a man, being a husband, being a father, simply because it talked most about getting mission done by training and preparing your people for the mission, talks about trust, talked about commitment, talks about excellence, talks about the things that you must do in order to be successful in life. All of it’s transferable to the Marine Corps to, again, be a better father, a better husband, a better person. And so I think, although I had a great foundation, I think the Marine Corps built on that foundation by leadership principles and ideas that I wish I had known 40 years ago, I would have still been a better father, a better husband, and a better person.

Adam: Looking back, what do you believe were the key elements to being able to rise to the top of such a competitive field? Marine Corps, the military, you're competing amongst the most competitive and what advice do you have for listeners on how they can make it to the top in whatever it is that they're pursuing?

General Stewart: Be ready. I tell the folks that I mentor when the stage light comes on, and all eyes are on you, you better be ready. That means you should have prepared, that means that you should have identified those areas that you are weakest in and are doing something to improve on those weaknesses. Whether that is speaking or writing, whatever that weakness is, you've got to dedicate enough time to offset those weaknesses. And where your strengths are, you better identify those strengths also and continue to do things that will improve Even in those areas where you think you are, you have great strength. If you're not prepared when the lights come on, the judgment begins, should you be there? Should you have the opportunity? So, when the lights come up, the stage is set, it's time to deliver. So preparedness is an absolutely essential commitment of time. So that you are ready when, you know- the Marine Corps has a model to be ready when the nation's least ready. I want my mentors, my mentees to be ready at all times. And that means I require them to read. I require them to work on their speech. I require them to present themselves in a professional manner all the time. And there's no excuse for not doing that. So preparedness and being ready for action are probably the key things. I try to tell people to be successful. I wish I had done that. I guess it's ironic to say I wish I'd done that better than I did because, as it turns out, it worked out okay for me. But just being ready is really the key and you don't get ready by being lazy. You may be given opportunities, but it's what you do with those opportunities that really matter. People genuinely generally want us to be successful. They'll create opportunities for success. And the question is, what do you do with those opportunities? And you may not get a second chance if you blow the first one.

Adam: At the DIA you lead a 16,000 person agency, you also lead much smaller platoons earlier on in your career. What are the key elements of effective leadership leading big units, small units? What does it take? What should listeners understand?

General Stewart: I think regardless of the size, the first thing I think is important, just know who you are. If you don't, if you don't understand who you are, and again, going back to the idea of where are your strengths and weaknesses? Because you can, you can write the best commander's philosophy and post it all over your enterprise, but you're judged by how you present yourself. Does your philosophy that you write reflect your day to day behavior demeanor activities. So if you can't translate who you are into commander's philosophy, and then translate that on a day to day execution basis, the folks will see right through you, they'll recognize that your words that you write do not reflect how you conduct your business day to day. I think the first and most important thing is who you are, so that you can demonstrate that every single day. The second thing I think is important is how you get a common set of values, whatever they are, and I will try to enumerate values here, but as an organization that everybody believes in certain core values of who they are as an organization. And you've got to over communicate that. And none of that applies at every level, small unit leadership all the way through to large organizations, we got to be very clear about what our mission is and what our core missions that we must be the best at doing. I don't want my machine gunner at the small unit level to be okay at this machine gun thing. I'll figure it out. We're relying on him to understand what his mission and his role is. And being the very best you got to train them hard to get to that level of excellence. Same thing within a large organization, everybody has to be clear as to what the mission of the organization is and what their role is in the mission. So you start with the top leader needs to understand who he is, so he can communicate that and can express that every single day. Folks have got to understand what their values are to the organization of the organization and how they fit within those values. They're clear on their mission. And each person not only knows the mission of the organization, but where they fit within that mission, so that they can understand their role and play their role as part of the greater good of the organization. And then you've got to wrap that around the history of the organization because if you understand your history, and you understand the mission, and you're clear on your values, and you're clear on your roles, now you can start refining the culture of the organization. All of those things wrapped together creates a culture of mediocrity, or a culture of excellence. And once you figure out which end of that spectrum you want to be, then you can try the organization appropriately. And again, this applies to small unit squads, the company level all the way through large organizations. And then finally, how do all of the leaders communicate all of that, all of our vision, all of our mission, all of our values, all of our ideas, all of our roles, and have a well developed strategic communication plan where you're telling that story, multiple times multiple formats, at the small level all the way through publishing things out there on the web. I think those are probably some of the key components for success in an organization.

Adam: What I love about what you said is, the advice you gave is pertinent to leaders in any organization, it doesn't need to be a military leader, it doesn't need to be a leader of a government organization and intelligence agency. You could be an entrepreneur, you could be a leader of a nonprofit, you could be a sports coach. The advice you gave on how to lead is so universally applicable and I really appreciate it and hope listeners were taking notes because everything from understanding yourself to being able to connect with and inspire the people around you, that's the essence of what leadership is all about. So I really appreciate that.

General Stewart: Yeah, you know, Adam, the thing about, especially when you talk about combat leadership, you're asking people to put their lives on the line in a combat environment, you better talk your way through what that really means. You're asking them to do the unnatural, asking them to risk it all because you have thought about what is the mission. What is the end state, what is at stake. And so if you can't figure out a way to inspire folks to take the hill, and again, it really, it transcends combat, because in the business world taking the hill is sort of more about how you get your return on your investment in your profit margins and alike, but it still applies to inspiring people because they understand exactly what their role is and how they play that role for the greater good of the organization.

Adam: You know, I've asked this question to other leaders, including other military leaders who have had on the show, and I'll ask it to you because you brought it up. And I think it's so relevant regardless of what kind of organization you're leading or what level within the organization you have a leadership role in, or even if you're not a leader, and you're trying to figure out how to become a leader or how to become a better leader. How do you inspire the people around you? How do you better motivate the people on your team, whether it's preparing troops for battle or whether it's preparing employees to become more effective in getting their job done day in and day out?

General Stewart: It goes back to that first item; if you know yourself. The challenge, I think sometimes we have is that we're not willing enough to show who we really are to our workforce. There's some notion you've got to be more stoic and you can't get too close. I never bought into that. I think the more you can show who you are, that you are, in fact, human, that you genuinely care about and you have genuine concern for the welfare of your people. You want them to succeed, you want to listen to them. You know, I've used this and I hear a lot of people using this; God gave us two ears and one mouth so we can listen twice as much as we speak. Sometimes it's really hard for leaders to listen. But if you can convince your workforce that you are listening to their issues and concerns, and you're genuinely trying to make their environment, their work, their situation better because you are connected to them on a human level that motivates the heck out of them, there. Probably nothing that I've seen that shows the humanity of a leader than to say, you know what, I got that wrong, to convey to the workforce that yes, I've listened, I've seen and I'm learning. And folks, I got that wrong. Now help me get it into the right place. That shows leadership. Humanity, I think, goes a long way to motivating people now. It's great to show your humanity, but it's not necessarily great. It's that, that humanity causes you to collapse at the time when you're necessary to make tough decisions. That's a balance that you have to play. So you start by showing some humanity, showing some compassion. Now, that doesn't mean you don't push people hard- you'll work hard to be excellent. But if you're going to push them hard, and working to be excellent, you probably shouldn't ask them to do anything that you're not either willing to or capable of doing. Now, there's some limitations like, as you get older, there's less physical things that you can do. But it's got to be very clear that you're in the mix with the troops. There is that phrase, you don't want to tell a young marine to go hike five miles with a full combat load while you sit on the porch, having mint julips. They want to know that their leader is with them in hard times, in good times, willing to make tough decisions, willing to learn from those tough decisions. Probably one of the most powerful things I think I learned at the DIA was to just go listen to people in the cafeteria. And that showed they didn't realize how much energy I was drawing from listening to their issues and concerns. They enjoyed seeing the human side of the director, and I was learning about the organization and drawing energy from their energy so that I could do a better job as a director. So you motivate them by demanding excellence, you motivate them by showing a little bit of humanity, you motivate them by just just genuinely showing that you give a damn about them.

Adam: Yeah, I think that's phenomenal advice. And I think that every leader should adopt the philosophy that you've articulated perfectly. I really couldn't agree with you more. On the topic of humanity; you wrote an incredibly powerful essay this past June, and I highly recommend that everyone reads this essay. It's called, “Please Take Your Knee off our Necks So We Can Breathe,” and it described your personal experiences and harrowing detail, battling racism in America, and how we could move forward as a country. I wanted to ask you a couple of questions on the topic. Number one is what advice do you have for leaders on how we can cultivate a true culture of diversity and inclusion within the organizations that we lead? And number two, how can we as leaders step up and really make an impact to help solve this problem?

General Stewart: Yeah, you know, probably the first thing I would tell the leaders because generally what we start off as well, we need to recruit more people in the disadvantaged minority and we bring in more people and that will somehow solve it. I would say probably start at the middle of the problem. Think about how you're gonna retain rather those that you have in your organization today. I just had a conversation with a young captain who was leaving the Marine Corps. And I asked him a very simple question; what would it take to keep you in the Marine Corps? And he was, he was kind of surprised, taken aback. He said I was the first person who ever asked that question. And looking across many organizations, we have talented people now in our organizations who don't believe that we want them to stay in our organization. So I think the first part I would tell organizations is, look around, see the folks who are in your organization that make up that disadvantaged demographic, whether it's female, Hispanic, African Americans, whatever it is, and go talk to them. Ask them how do they feel about being a part of my organization? And what would it take for me to keep them and continue to cultivate them to be leaders in our organization? So I'd start there. I'd certainly work backwards then to targeted recruiting. And again, the targeted recruiting is, if I'm going to join the Marine Corps, I have to really believe the Marine Corps wants me. So my message in this targeted recruiting and recruiting is let me tell you what I'm trying to build culturally in this organization. And there is a place for you at the entry level, and here's a place it's going to get you to the middle level. And ultimately my boardroom is going to look like the nation. But this is not going to happen organically. It has to be by design and that way causes some people to be anxious because they'll define it as photos, or tokens. But we've been studying the heck out of this problem with race in America, race in the boardrooms, for years now. And the idea is just be patient, it will happen organically. I no longer believe it will happen organically. There's much bigger issues then in the society of an organization, their issues about community reform, and I don't just mean police reform. How do you build trust back in our communities, so law enforcement and the citizens that they protect, actually are not terrified of them, but really believe they're there to serve and protect their education reforms, making education accessible to a larger population, and preparing that population for the digital environment of the future. Their economic reforms about how you create opportunities for African American to get into that middle class to get the potential that they could get into that upper tier, and they struggle with that. There's judicial reform that is essential going forward. So there's a whole host of things that we need to be tackling. But if you want to have some benefit in your organization, start or make a difference in your organization. I say, start with retaining your highest quality, disadvantaged minority, by letting them know that you care about them, and you want them to be part of the future, your organization.

Adam: A topic that is important to all leaders, regardless of what kinds of organizations they are leading, are managing risk and making effective decisions. You lead an intelligence agency. So those were two topics that were clearly very important to you as a leader. What are your best tips on risk management and decision making?

General Stewart: Oh, that was really, really hard because, you know, I know folks who will take one data point and execute, because they have a much higher risk tolerance. And I know folks will have 1,000 data points and are still wringing their hands because they just don't have enough to feel comfortable pulling the trigger. So I think this is really about the individual level of insights that drives them to pull the trigger. And I don't know a good way to quantify it. I've been a bit of a risk taker, I've had to dial that back, the more senior you get, the larger the organization that you're trying to manage, because my risk tolerance is different from the organizational risk. So I have to be mindful of that. If jumping out of a perfectly good airplane seems risky to others- it's not that risky to me- but if I tell the entire 16,000 person organization, we're all going to jump there's probably going to be some issues three. I think a big part of this is, and it goes to the second part of the question is, decision making, that one of the most important things for a leader of an organization is how you involve your leadership team in decision making, giving them again an opportunity to have their voice, not be paralyzed to make a decision. And then as a leadership team, as you execute, everyone is moving out in the direction of the decision. One of the things I've seen in dysfunctional organizations is not all the members of the leadership team are comfortable in the decision making process. They're not comfortable with having the really hard conversations there. You have not created an environment where they're comfortable with the hard conversations. And then you think you've made a decision and there are many members who think that That's where the conversation begins. I'm trying to be a little bit polite here. I believe when you create an environment, a decision making environment where your leadership team feels comfortable throwing dissenting views out there, having their voices heard, once the decision is made, everybody executes. I used to tell my team that I believe in execution; you can either execute the decision or you can be executed by choice. But what I never wanted was the team to walk out when you think there's a decisions being made. And now begins the discussion about why did we make that decision? And how do we undermine that decision? And how do we play the passive aggressive role so you get to create an environment where voices are heard, dissenting views are listened to and you take the best of those insights and you make a decision and the entire leadership team acts. Again, some will be much more tolerant to risk. Others will be more cautious. But as long as you get your leadership team all, generally speaking, the same decision, as opposed to, you know, going back down to their work segment section and go, I don't know if I really fully agree with this, but the boss said, we got to do this. Cuz immediately that makes it an executable. I don't know if that answered the question.

Adam: Yeah, absolutely. And I actually had General Martin Dempsey on the podcast earlier and one of the things that he told me when I asked him about this topic, and about his experience advising President Obama was that President Obama was insistent that all of his advisors express their opinions, even if they were opinions that he didn't agree with and the point that general does He was articulating was that it's really important as a leader to make sure that you give the advisors around you the opportunity to speak and to have the opportunity to express themselves, even if they're expressing advice that you're not going to ultimately take. Because that's how you build trust. That's how you ultimately build winning relationships with the team that you need with you to make those key decisions. And I think that that's very much in line with the advice that you shared.

General Stewart: Yeah, you got a couple of things that you can get from your leadership team. You can get them as advisors because you want to hear their views whether you agree with it or not, because it helps to shape your decision, or you want them to be an audience. And, if you want them to be an audience, it doesn't really matter who's on your leadership team. They can just listen to you while you spout off and applaud you when you're done. I kind of liked the model that way. The diversity of ideas, and they're comfortable enough in that environment to say, “Boss, I don't agree with that. And here's why I don't agree with that.” And then we can all as a leadership team, have a conversation about that, which an individual doesn't agree with. And I think that makes everybody a little bit better the first time you do that it's uncomfortable. But once you get to the point where you built a leadership team, and you use the key word, that’s trust each other, you can be vulnerable with each other, you can get some incredible advice and things that you may have blind spots to that you never even thought about. So they can be an audience or they can be advisors and I kind of like the advisor part.

Adam: That's a great way of framing it and a really important way for leaders to understand who they have around them and how they're really considering those relationships. So, I really appreciate that.

General Stewart: I'll tell you one other thing though. It's hard to get them started in sharings. Sometimes it's hard. You always have somebody who always wants to spout off. But part of what you've got to do is study your audience when you're in that setting early and you can see some body language or someone wants to say something, but they're just not quite comfortable doing it. So the first couple of times you call someone out because they appear to want to say something, you get one of two things, either people speak up or because they know you're gonna call on them, or they sit on their hands and never move because they don't want to be called out. But either way, you got to pull them out, you got to get all their views and opinions, because it helps you make better decisions.

Adam: You're taking me back to my days as an MBA student. When you're sitting in an accounting class or you're sitting in a finance class, there are certain kids who can't wait to have the teacher call on them and can't wait to have their voices heard. And then you have other kids who are just sitting there praying to God that they don't get called on because they didn't do their reading. And I could tell you that, depending on which class it was, I was either in category one or category two. So for accounting, I was definitely not the guy hoping to get called on but for some of my other classes, I was there with my hand up. And I'm sure if any of my MBA classmates are listening to this podcast right now, though, they're nodding. So I'm gonna ask one last question. And that is a question about the mental side of success. You spent your career in the military, not only ready for battle, but often engaged in warfare, including in your last post cyber warfare, how do you prepare mentally for success? And how can anyone develop a winning mindset?

General Stewart: That really is a great question. The mental preparedness, I guess, part of this is I'm a historian. I consider myself a historian, I got my degree in history. There's really nothing new under the sun that someone else hasn't experienced and assured in any biography of some sort, so you can kind of immerse yourself in history, which is probably a good start point. But you never know how you're going to react the first time you're faced with danger. And I don't want to overplay this, I am not an infantry guy who's been on the fine lines, but taking people into a combat environment where you're not sure how it's gonna play out- my first my first experience was Desert Shield, Desert Storm, and leading a small Platoon, I guess, a little bit better than a platoon- a pretty concise detachment, now I think about it. And the idea that you might not bring someone home you took with you... It was tough to reconcile mentally that you have in your hands the life, in this case, of a number of young men, and how will you deal with a casualty or deal with death? And there's no reading that prepares you for that. There's nothing but the experience that prepares you for that. I think the readings of history and watching historical documentaries give you some idea but there's nothing that replicates being on the ground at any time. In the cyber domain, though, I don't know if you get the same sense because it fires from afar. It’s capability from a global platform and you don't necessarily see the impact, except that you know that you're having some impact around the globe, so, I don't know. Mentally, it has not struck me as something I wrestled with this. Maybe you've given me something to think about, the mental preparation for cyber warfare because it's remote warfare. And maybe that's a dangerous thing because if you can't see the consequences. Now if I dropped the 500 pounder, I see the consequences then. If I shut down the electrical power grid, I kind of know what the consequences are, but I don't see the impact on not only my adversary, but potentially the civilian population. And I recognize that there's an impact there. But because it's so remote, I don't think about it the same way as a kinetic strike. So you've given me something to think about- how you mentally prepare for cyber warfare, and all of its implications? So now you give me a homework assignment.

Adam: How can anyone develop a winning mindset?

General Stewart: How does one develop a winning mindset? I'll tell you, I've gotten a lot better at this than I have before. I used to be horrible watching the Chicago Bears. I would take it personal because losing was just so painful for me. I just, I was an intense competitor. I didn't want to lose at anything. That's why I guess one of the reasons I love guys like Michael Jordan, who can not only will his team to win, but doesn't find losing acceptable in any way and it's driven by, I have to be successful without being a horrible human being in the process. I think anytime you start accepting, losing as, okay, you tolerate something less than excellence. You tolerate anything that looks like mediocrity. You absolutely cannot develop a mindset of winning. Winning is winning is what matters. In any competition coming in second or third or fifth is just, it's not acceptable. And if you don't have that kind of mindset then mediocrity becomes okay.

Adam: I think the Chicago Bears might need you to come in and give them I would say a pep talk, but they need more than a pep talk from you they need.

General Stewart: Their measures are gonna be okay. I think. I think the sports media likes to hate the Bears. And I don't know how you go from last year, going into the season when you're a contender. And, and a year later, you're the worst team in the league. I think they like to, they like to beat the Bears. But if you know anybody who can get me into the various locker rooms or pep talk, let me know. I'll be happy to do that.

Adam: We'll see who's listening to this podcast. General Stewart, thanks so much for joining us. Thanks for all the great advice. It was a pleasure.

General Stewart: Alright, thanks, Adam. I appreciate you having me on and hope something I said was meaningful to your audience and thanks again.