Insights With Ben Chodor: Featuring Jimmy Blackmon

Ben Chodor's Insights series is back with Jimmy Blackmon, a leadership expert, author and professional speaker.  

Ben Chodor

January 28, 2021

Jimmy Blackmon is one of the most experienced military combat leaders in the United States. He has led high-risk missions all over the world and served as aviation commander during battles in Afghanistan - in which four Medals of Honor were earned. 

Even more extraordinarily, Jimmy is an IBO World Champion in archery, made the U.S. Armed Forces World Cross Country Team and has run a 2:33 marathon!

Jimmy’s leadership experience in the armed forces has led to a prolific career as a writer and speaker. His unique perspective contributes to his ability to motivate teams to work together purposefully towards a common goal. 

It was my honor to interview Jimmy about his latest book, Cowboys Over Iraq

Watch the full interview below, and stay tuned for more conversations in 2021!

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Ben Chodor: Good morning, good afternoon, good evening wherever you are, and welcome to the show Insights with Ben Chodor. 

I’m actually really excited this week, and one of the reasons why is that I get to interview Jimmy Blackmon, whose book Cowboys Over Iraq was an incredible read. I actually read it in two days - two afternoons sitting outside in the sun. Loved it. I learned a lot about leadership. Incredible storyteller. In fact, instead of me talking, let me bring Jimmy in. 

Jimmy! First, thank you for your service, sir. It is amazing what you and your fellow soldiers have done for our country. It doesn’t go unnoticed by me, and I really appreciate it, so I just wanted to first say thank you.

Jimmy Blackmon: Well, thank you, Ben. 

Ben: Now, you don’t have to thank me! I’ve got to tell you one thing before we jump into the book - one of the things where you had me at the very beginning of the book, you start talking about when you first got to Iraq, and you sat around with a bunch of the other senior leaders and everyone was smoking cigars, telling their war stories. And I truly felt like I was there at that picnic bench, sitting there as people look at their cigars. Even when I go play golf with my friends, they do the exact same thing. Is it lit? Is it not? And the moment you have a cigar in your hand, it’s time to tell stories. It was amazing. How did it feel, now in hindsight after writing the book, when you were there, and they were all regaling you with their stories? 

Jimmy: Yeah, so for me, that’s at the beginning, as you mentioned, and so I showed up actually after the initial invasion had taken place. So those guys had created these bonds and this crucible of war, and they had all these stories that they loved telling, and they’re so exciting, but I’m not involved in any of that, so as a senior leader coming in, it made me wish that I had been able to be there and be a part of that. But it also gave me some concern - okay, how long are we gonna be here - we had no idea - am I gonna get an opportunity to be a part of that conversation? Am I gonna have an opportunity to be able to tell my own story? At that point, I didn’t know. 

Ben: Yep, it’s great, I mean there’re so many little things throughout the book that really struck me. You tell a story about the troops - as the ground troops - at first not trusting their air coverage until they got to know and until they actually saw that, and I find in business, it’s the same thing. When I bring a leadership team together and new people come in, building a bond of trust doesn’t just happen, right? It’s something that has to be worked on. 

One of your quotes, General Petraeus’ quote, “It is a military axiom that no plan survives first contact.” 

I mean, when I heard that my head kind of went, “My God!” It’s also the same thing in business. You go down with this plan, the first thing you do, but the moment you’re out there and there’s customers and competition, it’s not the same thing. Why did that resonate with you? 

Jimmy: Yeah, so, we know that the plan, I think it was Eisenhower said, “In peacetime, plans are worthless, but in combat plans are everything.” Planning is everything. It’s kind of along the same lines of, we plan for the worst situation we think, and we try to build flexibility, but then, once the enemy gets a vote - once the game is on, they’re living, thinking, breathing enemy, just link in business - our competition gets a vote, pandemics get a vote, as we see, markets get a vote. And so, how do we build flexible, agile organizations that are unified by vision and purpose and have a flexible strategy that very quickly they can put inputs to adjust? 

Ben: Do you think it could be taught? Because, reading the book, you can tell that they way your mind works, you’re thinking several moves ahead, and you’re very flexible. But do you think you can take anybody and teach them that same concept? 

Jimmy: So, you said anybody, and I believe, well, no, I’ve thought about this a lot - not anyone. Some people, for example, just can’t delegate and trust their subordinates which creates speed and agility. They just can’t let go - it’s a personality thing, so they may be taught, and they may understand, but they can’t do it. Others see it and it’s proven to them, you see the success of Steve Schiller, who was my boss there, and others go, “Hey this is working, what I’m doing is not,” and they do change. 

So, it’s a spectrum. Some folks learn and see it and, you know, and can go a little bit down that road. Others, it’s about risk aversion and accepting risk as a leader - it becomes a challenge for many. 

Ben: Is it easier when you go into a corporation, and now you’re consulting, and taking a bunch of executives and teaching them to be a little more flexible, or a soldier who has been taught just to do everything the same over and over again? In the book, when you talked about your first night there - your shoes had to be lined up perfectly, even though you didn’t think anyone really cared, but you knew it would keep you up all night if you didn’t. Is that something that you think? Like, a soldier is taught to go down this road, follow, and be flexible. Is it easier to teach someone business, or is it just the person? 

Jimmy: Let’s say my experience is generational. I’m 51 years-old. My generation and older, a lot of folks, it’s hard to teach an old dog new tricks. I meet a lot of senior executives that have been very successful that struggle with change. Our millennial generation, the Gen Z, which is now in the workforce, they’re very open to change and they’re open to try a lot of - they’re very entrepreneurial, and they’ll try new things and roll with it more than my generation and older. 

Ben: That’s so interesting to me. So, how do you break through to a group that’s not used to being flexible? 

Jimmy: Yeah, I call them “small victories.” One thing at a time - show them some success in other organizations, other companies in their industry. Show them that the status quo for the last ten years is not going to make you successful in the next decade. What got you here is not going to take you to the next level. And it comes down to, really today, especially with a lot of large, older companies, it comes down to these organizational characteristics, these traits that permeate throughout the organization, you know? During the industrial era, we were very hierarchical and bureaucratic by nature, and it was ideal for it’s time and place. The 21st century has fundamentally changed the environment in which we operate. And those things that made us successful throughout the 70s and 80s and 90s, they don’t work today. 

Ben: It is so interesting, as part of Notified, we’re a bunch of different acquisitions and some of the groups that came from larger organizations, they don’t like to take risks, they don’t understand when I talk to them like “we need to disrupt ourselves.” We need to think out of the box, and we need to use ingenuity and initiative and, you know, in the book you even talk about how you guys retrofitted some of the helicopters so they would work better in the Iraq heat, or where you were, so they’d be better for combat. I find it one of my biggest frustrations: how do I get through to people? It’s okay to disrupt what you know. 

Jimmy: We’re calling this the age of disruption, right? And what initiated that was technology, and now we’re seeing that it’s much more than that. This pandemic has forced us to take a unique look at ourselves, and we’re finding out who’s really important in our companies. 

I had an executive vice president of a Fortune 500 company tell me, “You know, I think I could die and nothing would change.” It’s like, I didn’t realize how unimportant I really was. 

Ben: Alright, so, not to jump off the book, but since you brought it up, and as we’re going through COVID-19. When you look at everything, what does it make you think? With your military background and everything that’s going on, can you believe we’re going through this?

Jimmy: Yeah, so it’s, you know, the war, as I mention in the book, necessity is the mother of all invention. The war really sped up our learning curve. It forced us to question our assumptions and the way we had always done things. We were getting out maneuvered by an inferior enemy and it was because all of our authorities were held at the very top of the organization. It made us slow and bureaucratic, which really caused us to assume more risk to the force, because we were late getting there. We were shooting behind the target. And so, this pandemic is, I think, terrible that we’re having to go through this, however, it is a forcing function to cause us to question many of those same things in terms of business. As we try to define the new normal, we’re going to see that it’s not a new norm that is a steady state. We transformed from that old version of us to a new version, but it’s a set of characteristics. We’ll realize that some folks can work from home, some folks can’t. Maybe commercial real estate will take a hit, I think, and that means that we’re questioning a lot of the assumption we made. We’re going to find some sort of hybrid model of normal, but we’re going to try and create organizations that, when the next thing happens, whatever it may be, we’re postured to be able to take advantage of that, not be a casualty of that. 

Ben: I agree. So, with your background though, do you enjoy being in an office with others as opposed to working alone? 

Jimmy: I am a people person. I’m doing an executive leadership series with a company now. I did the first cohort of their leadership in person, and I’m doing this one on Zoom, and it’s just, the ability to shake a hand, put a hand on a shoulder, look in an eye, read body language of everyone in the room - for me, I thrive and feed off of that. 

Ben: Me too - I miss people. Alright, I’m gonna look down at my notes because I want to get your quote perfect here. A phrase in the book that stuck with me was, “While war is common, it’s not natural. It produces unparalleled bonds, a brotherhood forged in the heat of combat.” 

Do you think we come together more easily the more difficult and harrowing the task is? And how do good leaders facilitate this? 

Jimmy: Yeah, so that quote is interesting because the first cut of the book, my editor came back and said that some would argue that war is natural. And what I mean by that, to clarify, is that I don’t think it’s natural to humans. It affects us all. And it affects us all differently. Okay, so yes, so in my last book, Pale Horse, I was sitting at my desk and my doc came in, and he threw two pieces of paper down on the desk in front of me and he said “you need to understand this.” And I'm like “what is this?” And it was single-spaced, two pages. He said “every one of those lines is a soldier in your organization that I am either medically treating or counseling for stress or anxiety and how this is affecting them. As a leader, I’d become so focused on the mission, what we were doing, because we were fighting every day, and so we have to understand that the environment is stressful. I mean, what’s going on in homes today, people are worried about “are my kids going to go back to school, and I going to get day care?” If it’s some hybrid model of online learning and in-person, how can I manage that? Single-parent families are different from traditional families. There are so many complexities that leaders and going to have to have the skills to handle that we have to be very open to everything, not just us, everybody doesn’t feel the way I feel or handles the stress in the way that I handle stress. 

Ben: I agree. I’ve been trying to spend a lot of time with my global executive leadership just asking them what they are going through, and I do feel like, in our own way, we are going through our own war. Our business is growing because we do a lot of virtual and a lot of PR, but one of the most interesting things is that, as we fight each of the battles, whether it’s technology things that we’re working on or whether it’s employee things or customer things, I feel like we’re building a stronger bond together, because we all have the same mission. I think one of the things that everyone, since they’re working from home, likes to know more than ever, why are we going up this hill, how are we going to get there, now that we’re on this hill what’s our next hill? They love knowing what the next thing is, because they can’t look to someone to the left and right of them to sort of boost them up. And this is nice, and it’s nice seeing you, but this isn’t any human interaction. 

Jimmy: No, and I agree. So, these are new leadership challenges. How do you build that team, those relationships, how do you unite between vision and purpose when people are displaced? When it is virtual? And we can’t underestimate the discussion that takes place after the meeting or before the meeting starts. Just like conferences - I’m a keynote speaker all over the world at these big conferences. It isn’t just the seminar, it isn’t just the speaker, it’s dinner that night. That’s where business and relationships, trust and those things take place. That can’t be done virtually, so it’s a challenge, but you bring up another great point, that Steve Schiller in my book was a master at, and that is this idea of intent. He spent a tremendous amount of time trying to communicate very clearly our vision, our purpose, and his commander’s intent, as we call it in the military, so that everybody had alignment of what that vision was. And then he trusted and empowered them to make decisions based on that mutual understanding. And that’s what we need to speed our businesses up today, to empower and entrust subordinates to execute and make decisions based on that common vision and purpose. 

Ben: Yep, again, the whole thing is, my job is to empower other leaders to make decisions, whether it’s one down, two down, three down in the organization. And it doesn’t happen overnight. But, since you brought up Schiller, one of the interesting things that you mention is how he had this whole excitement and enthusiasm for innovation, that it was infectious, right? And before we go to that, it just made me think, you also mention that every time you would talk to him, he really made you feel like he was interested in what you say, and I know that I’ve spoken to a lot of people that I’ve reported up to, and I’m sure some of my team has had conversations with me, and they can tell I’m sending emails and I’m not giving them 100% of the focus. Was he really like that, when you were with him, he was lasered in on what you were talking about?

Jimmy: Yeah, I laugh, because Steve Schiller was a unique individual. He had just little things - when you would shake his hand, he would catch you off guard almost every  time. He was known for this - he would shake your hand, and when you started to shake, he’d pull you off balance and you’d fall into him, and it was really awkward. And if you knew him and if you were around him a lot it would get you. Little things like that, conversations would always begin with a laugh, always begin on a light note, whether you were a private or whether you were his peer, he would do those little things and be very engaging, and he championed innovation and initiative. He knew that he had to get others to see that their peers were coming up with ideas, were innovating, trying to make us better, and when he would reinforce that, they would go “hey! He is listening, he does want to move the needle in terms of our readiness and capability.” And so, it made others eager to try new things. I mean, he did not see the world with a ceiling or floor, I assure you. There were no walls in the building. He was open to pretty much anything, and that made some people uncomfortable. But it cost him to be able to, at an unprecedented pace, make us more perfected. 

Ben: I love that. So now, you’re doing your job with corporations. How do you instill that in a leadership team that you’re working with? 

Jimmy: Yeah, so, one client that I have right now, they are investing in a portion of the business. So, they’ve identified this area that they need to create new products, they need to sell new products, and they’ve gone to great lengths to find the right leader of that organization, number 1. They have not just thrown the hiring process out there, they’re looking for the right types of people with the right skill set to think innovatively. They’re championing this. So, I think that’s a really good model, especially if you have a very large business. You’re not going to change the business overnight, but if you can identify areas, almost like your beta test, where you can show it and prove these things, then it starts to kind of cross pollinate across the business. 

Ben: I love that. Alright, I want to jump because I have a couple more questions for you and I know your time is valuable. Let’s talk a bit about the importance of morale and tactics to keep it high. I’m a big believer of revving up the troops, revving up the team, getting them excited, hearing them. But, you know, you say it really boils down to “people need to be heard.” How do you enable that? How do you enable that in the military, that you can enable people to be heard when you’re giving them orders, and how do you transition that into business? 

Jimmy: So, it kind of goes back to that listening. When I do all my leader behaviors and leader traits, a seminar that I do, one of the things I talk about, just to share this example with you, we have a tradition in the military where every Thanksgiving, we the leadership dress up in our dress uniforms and we invite our soldiers to bring their families and eat Thanksgiving dinner. And we the leaders serve them Thanksgiving dinner. So, we dress up in our uniform, they bring their families, we feed them, and they sit down at the tables throughout the dining facility. And then it’s traditional that we the leadership roam around table to table, meet the children and the wives. And a question that’s often asked is, “How are you doing?” And I would get my leaders together before we did this, and I said “they know whether you truly want to hear the answer to that question before you ever ask it.” 

How are you doing? 

They know if you care. 

And so, I would then tell my leaders, those young men and women are willing to die for you. All they ask is that you be worth dying for. Is that too much to ask? 

Ben: That’s very humbling. 

Jimmy: And so I ask business leaders - be the leader you would desire your son or daughter to work for. Isn’t that a fair litmus test? Be the leader you would want your own child to work for. When we engage people in that way, in a meaningful way, we listen to understand, not just to hear. We engage and they trust us, leader to lead, lead to leader. We can move organizations. And people get up wanting to come to work. You control your little corner of the world, and so,  you get to choose every day whether to place people, put the key in the ignition in the work and say, “I’m going to work, and we might have a bad day, but I work with good people in a good climate, and I want to be there and work with those people.” OR, they can put the key in the ignition and go “another day at work.” 

Ben: I say a lot on my end of the week video to my team, you know, every night I go to bed wondering if I did right for my team. Because I’m responsible for 1,300 people globally, and I need to make them feel engaged, empowered, motivated, and yet, at the same time, I don’t know if I’m always doing the right job. So, as you’ve gone through it in your career, and some of the soldiers you’ve worked with, do you have any anecdotes on how they have taken this ability to create morale, motivate, that you want to share? 

Jimmy: Well, it’s humbling and very rewarding when guys that worked for me are now taking over as battalion commanders of four to six hundred soldiers. Brigade commanders, I have one I emailed about six times two weeks ago to look at his leader development program. And of course he’s modeled it after the one he went through when he worked for me, and that is very rewarding. 

Ben: So let me ask you one last question. If you had to give a message, I have 1,300 people in my organization, but there’s like 8,000 in the global organization, plus all the other people who are watching and listening to this. When they go to work every day, or are running a team, what are one or two things that they should be thinking about to motivate them or to keep morale up? 

Jimmy: I don’t care how technologically advanced we’ve become, life is and always will be about people and relationships. That’s the most important thing. I truly believe that. Engaging with people in a meaningful way, gaining their trust. We develop trust using the equation character times competence equals trust. Character - it’s easy to lose, but it’s hard to gain if you don’t have it. Building a team of people of character and then demonstrating competence day in and day out, performing, doing  your part, pulling your fair share of the load, that equates to trust and that is powerful in organizations. 

Ben: I love that, and actually, you know, a saying I just heard that resonates with me is “a true test of a leader is how many leaders you end up making.” And it sounds like, in your career, you’ve created a lot of leaders, and our country is thankful for it; I’m thankful for it, and now you’re doing it in the world of business. 

Everyone should read the book, it is amazing: Cowboys Over Iraq. It is a must read. 

Most importantly, Jimmy, stay safe. Thank you for your time, and, again, thank you for your service, sir. 

Jimmy: Thanks for having me on, Ben. 

Ben: Have a great day. 

Jimmy: You too. 

Author Name
Ben Chodor