[Podcast] Scaling Leadership Development to Align with Team Size


Duration 27:24


Leading a team of five is different from leading a team of 5000, leaders must adapt and evolve to the size of their team. Chris “Elroy” Stricklin, former Thunderbird pilot and senior military leader, shares how he transitioned from leading formations of aircraft to commanding more than 7000 people across the globe and what business leaders can do to scale their approach to leadership development from one team to another.

What you can take away from this episode:

  • Key leadership techniques for one-on-one mentoring
  • How to scale success for a small team
  • What to do when leading a large organization and you can’t personally interact with everyone on the team
[Below is a transcript of the episode.]

Thor: Hello and welcome to The Business Thorcast. Leaders are made, they’re not just born. Everyone can be a leader, but it’s something that needs to be developed over time. Not every leadership role is the same, and leaders need to adapt and evolve to fit the position. So, what are the key leadership techniques for one-on-one mentoring? How do you then scale successes for a small team? And finally, how do you lead a large organization where you can’t possibly interact with every single person on the team? I recently sat down with Afterburner team member, Chris Stricklin, fighter pilot and senior military leader, to talk about the transitions he had to make as he went from leading formations of aircraft to commanding more than 7,000 people across the globe.

Thor: Today we’re going to be talking with Chris Stricklin. Chris Stricklin is an F-15 pilot, in the United States Air Force. He was not only an F-15 pilot, he went on to become an instructor in the F-15 and he taught at Tyndall Air Force Base. He was the lead evaluator pilot there. He was also a Thunderbird pilot. So, he flew with the aerial demonstration team with the Air Force. Thunderbirds, if you’ve never seen them fly, exactly like the Navy’s Blue Angels, only better because it’s the Air Force, right, Chris?

Chris Stricklin: That’s right.

Thor: And after that, he went on to become a squadron commander in charge of 50 people, went on to Afghanistan and led a team of more than 1,000 people in combat. And then finally, his last role in the military was in charge of 7,000 people remotely dispersed all across the globe on one of our nation’s most critical defense initiatives. Welcome to the show, Chris Strickland.

CS: Thanks, Thor. I appreciate you having me on today. And I definitely appreciate the ability to sit down for a cup of coffee and talk about leadership, what we learn from the military, and how we apply that to business.

Thor: One of the best things that I find and I like about working at Afterburner is that these conversations take place all the time. This stuff happens over a beverage of choice, when we’re on the road, over breakfast. We just happen to have a microphone sitting in front of us right now, but we’re constantly having these dialogues about what we learn from our adventures.

CS: That’s exactly it. And I think that’s how your ThorCast started, Rachel and the team in the office heard us sitting around shooting the breeze one day and went, “Wow, we need to record this and get other people to listen to it, and continue the conversation beyond our small group at Afterburner.”

Thor: Yeah. We’ve been exposed to some incredible opportunities, incredible adventures in each of our journeys, and it made a lot of mistakes along the way, too. And it’s a great opportunity to talk about how we’ve learned from those mistakes and moved on and became better leaders for it. So this is the first time that I’ve probably ever called you “Chris.” You know that I know you as Elroy. You know me as Thor. That’s your call sign. And we know, as fighter pilots, we all have call signs. I lived with mine for 15 years. How long have you had Elroy as your call sign for?

CS: For 23 years.

Thor: And there’s always an interesting call sign story behind every name. There’s a reason why that person got that name, and there’s typically two versions of the story, one that’s safe for public consumption, and one that probably is a little bit more PG13/R rated and requires a couple of beverages of choice to actually tell it. Why don’t you tell us the PG version of why you are Elroy?

Elroy: So, it’s pretty easy when I’m standing in person with people because I just point to my face and say, “Have you ever watched the Jetsons, the cartoon on television?” And at that point, they all throw their head back and laugh because I have what is called the natural. Because if you’ve seen Elroy Jetson and you’ve seen my bio picture, you know that we are one and the same.

Thor: You really should go Google Chris Stricklin right now and see the picture, because it’s uncanny. You’ll immediately say to yourself, “His boy Elroy,” after you see the picture online. But let’s talk about your experience. First, I want to ask you, you had all these different roles in your career, you got to lead people at every different level, got to participate in some incredible things in the sky, what was your favorite job out of all those?

Elroy: That’s a tough one and most people, when they ask that question, think I’m going say the Thunderbirds, and flying the red, white and blue jets. But in all honesty, it was my opportunity to work at the Pentagon, 25,000 people working in one building.

Thor: Yeah.

Leadership and Decision Making

Elroy: And the reason I loved that is because I was incredibly low ranking. I went there as a captain, as a young 30 something, and I was routinely in meetings with people four to five echelons above where I was in the organization. And it wasn’t just what I got to do, it was my ability to see their leadership behind the scenes, see what they took into account as they were developing their decisions, see what they negated as they were developing their decisions and see who they brought them in to bring into the conversation, so they learned from people around them. It was being a fly on the wall in meetings like that that affected our nation and our military that really was my best opportunity in the Air Force.

Thor: So, a lot of people are listening to that and they’re probably saying, “Yeah, but you’re inside the Beltway. This is the bureaucratic nightmare, and just the definition of the machine that really doesn’t move.” How did you see them actually make decisions and be effective in that environment?

Elroy: I was really impressed with how informed the decisions were. When you watch the news, you always think they’re just making off-the-cuff decisions. And to watch the experts they brought in, to watch the research they put in, and also understand that the military moves. There is a definitive end to your decision making, and you have to not get bogged down in analysis paralysis. At some point, you need to have the 80% solution and move forward with it. You can’t continue to bring people in and talk until you have that 100% all-knowing decision.

Thor: It’s such a great point. We didn’t have the luxury of sitting back and admiring the problem in the military, did we? We often had situations where we very quickly had to come up with a plan, not necessarily just in combat, in training, in exercises, we were put to the test and they made sure that we came up with that 80% version of the plan that we could go out and execute right now instead of waiting for perfection.

Elroy: That’s true. More often than not, anytime we were given a task, it started with, “This is due Friday afternoon at 4:00. You’re taking off on Saturday morning at 8:00 AM to go around the world.” We always had that end game in mind before we ever started planning, before we ever started thinking, and before we ever started formulating our decisions.

Thor: And this was something I noticed in business school. It’s probably the starkest example of how we were different from the rest of the world. I remember sitting down in business school and being a little bit overwhelmed because they spoke a completely different language? It sounded the same… I basically spoke Portuguese, they spoke Spanish, and it sounded the same, but it wasn’t. And they were talking about EBITDA. And even just differences as simple as revenue and gross profit and net profit, all those things just sound like a foreign language to me. But the one place where I saw military members in general have an edge, have an advantage, is when we would do exercises in that classroom and they would challenge us to do something as quickly as possible, come up with a plan to go execute it, and there was a lot of hand-wringing that took place among the corporate team members in this executive MBA program that I was in. And a lot of were reluctant to make a decision, stick to it, and then iterate afterwards. Have you experienced that, too, after working with Afterburner for a while now?

Elroy: After working with Afterburner, you and I know from sitting down with Fortune 100 companies, with CEOs, with C-Suites, the amazement in their face, because they do a good job of making decisions. But when we ask the key question of, “Where are you taking the organization? What end game are you trying to get to?” And you and I both know, behind closed doors, they go… A lot of them, I’m not going to say all of them, will say, “I didn’t think of it that way. As we were working our plan to get there, I never have thought about that there.” And we have to define that for both our organization, for our people, for our members, as we go down that decision-making path.

Thor: And you’re kind of taking it to the graduate level. And if I’m interpreting it right you’re saying, the reason they don’t have a sense of urgency to act right now on the tactical things or they’re not comfortable acting on the tactical things is they don’t know their long-term destination. It’s the equivalent of hopping in the car and saying, “Where are we going to go today,” when you don’t know where you want to be in a week on the road trip that you’re about to take.

Elroy: That’s exactly it. And as you look across corporate America, no different than the military, we are tactically executing as hard as we can.

Thor: Yeah.

Elroy: Everyone’s coming to work every day and running full speed in the sprint, but they don’t realize they’re actually in a marathon or know where the finish line is 26.2 miles down the road.

Thor: Yeah, what a great point. That we have got to define that vision for success upfront to make more informed decisions and have more confidence about the short-term actions that we’re going to take right now.

Elroy: And to take that one step further, it’s about the power of passion. So, as you look at everybody in your organization, whether it’s 50 people a 1,000 people or 7,000 people, if they all know what that finish line, what that goal looks like, then they can back it out and go, “How do my actions every single day contribute to the success or failure of that goal?”

Thor: Yeah.

Elroy: And as I challenge people in all of my leadership roles, know how you fit in every single day. If what you do on a daily basis doesn’t contribute to the overall vision and mission of the organization, you need to back off and talk to your supervisor so that we can re-allocate your manpower somewhere else. And that is not meant to be a negative. It’s meant to say there is no overage of manpower in any business, in any military, in anywhere in corporate America. We have to know that what we’re doing makes a difference and that we contribute to the overall success of our organization.

One-on-One Mentoring

Thor: What a great point. And you’ve taken that leadership role, and that teaching role, and you started with the one-on-one relationship, where you’re teaching a student in F-15s. And then you moved on to teaching three wingmen at the same time, you take a formation out as instructor, and then you led a squadron with 50 pilots, and then you moved on to a 1,000 in a combat zone, and then 7,000. One of the questions that comes up most often, when we’re helping out corporate leaders, is they’ll tell us, “I felt pretty comfortable in my last job. When I was leading the small team, I knew everybody’s name and I knew the names of their kids, and we knew each other really well, we just executed like a well-oiled machine. Now, I’m in charge of all these people, and I can’t shake their hand. I certainly can’t be in front of all them at any given point and time.” So, how do you make that transition from instructing 50 people to now 1,0000 people that you’re in charge of?

Elroy: I think that’s a good question, as you think about it. And I will tell you, overall, in the military, we do a job for two years. Every command tour in the military is exactly two years long. From the time you take the flag to signify you’re in command, until the time you hand it over to the next commander, it’s two years. And every time I sat down in any role, from the smallest to the largest, I will tell you, after I took the flag and I sat behind my office door, I felt incredibly uncomfortable. I felt incredibly ill-prepared for the challenge that was in front of me because I knew, when I open that door, people would look to me for answers, for solutions and for knowledge. And I look back on the military and say, “This has been going on for a long time. We develop leaders, that’s what we do.” And the military assumed I was ready, just like everybody else when they took the flag, and therefore, I must be ready.

Elroy: And I would step out there and lead and do what I knew how to do, do what the Air Force had taught for 16 years, for 18 years, for 20 years. No different than in corporate America. Many times, as we’re out consulting with companies, I have people go, “Well, when I enter a leadership role,” and I step back and go, “You’re in leadership role right now. It doesn’t matter about your title; your peers are looking at you for leadership. They’re looking at you for what to do, for how to do it, for how not to do it. Are you making a good impression on those around you, because we are leaders every time we wake up in the morning and everything we do?

Thor: You said so many interesting things in that statement. I want to break down just a couple of them. Before this podcast started, I literally just got off a call with somebody who’s in charge of key accounts for a large organization. Key accounts are their contracts that are over about $20 Million. Average order values in the neighborhood of $60 to $80 Million. They had their first greater than $100 million deal this year. And we’re talking because one of their teams, they got seven teams within this group, one of their teams is not going to make their Q4 goal, and this is one we’ve been watching really closely. And the feedback I’ve given her up to this point is that the leaders of this team are really good at loving their team and really good at making them feel appreciated, like a leader needs to do, but they’re not good at the boundaries. They’re not good at pushing their team out of their comfort zone and executing on something when they don’t feel ready.

Thor: And as I’m talking to her… No kidding, half an hour I had of this conversation. As I’m talking to her, I’m thinking about when I was just starting to fly in the Air Force and how I spent a career being uncomfortable. Because just like you said, if they would’ve waited for me to say, “Hey, I’m ready to solo, I’m ready to go up there and fly by myself,” that day probably wouldn’t have come, because if it were up to me… You could never mitigate enough risks when I was a young 22-year-old at that point and make me feel comfortable with it. But we did it because the system pulled us in that direction, and I knew the machine that was pushing me through, knew it better than me. So how do you create that? As a leader in a corporation listening to this right now, how do they build that?

Define What Success Looks Like

Elroy: So, you have to think about that, and just like you said with flying and soloing, soloing the F-15, a $50 million aircraft that is the size of a tennis court, and we soloed it the fourth time we climbed the ladder. The first three times, we were with an instructor, and the fourth time they said, “You’re going out by yourself.” And none of us felt like we were ready, but our instructors empowered us and equipped us with the tools and techniques we needed to be successful, with the ability to safely take off and land that massive supersonic aircraft. And it’s the same thing in leadership, you empower your organization. You have to have boundaries. Everybody wants to be in a bound organization, as much as they say they don’t. Do you set work hours for them, tell them what’s acceptable and what’s not? That way, if they need to come in late one day, they know to go to their boss and go, “Hey, boss, I need two hours off. I’ll get my work done, but I’m going come in two hours late for my family.” But you have to set those boundaries. You set the fact that professionalism is expected.

Elroy: Many organizations don’t talk about this. They say, “Well, that’s assumed.” You need to define this for the people that you lead. What does professionalism mean? So, in the military, in the flying world, I look at professionalism and know that it is the one way that we bound everything that makes us. It’s the only way you can achieve the proper blend of pride, desire and aggressiveness, as you move forward, and that is the epitome of what a fighter pilot is. That’s the epitome of what your organization should do to be successful in corporate America. You want to blend those three things together to motivate those around you so that you’re not overly aggressive. Everybody understands your desire and knows the pride you take in your work.

Thor: But so often, boundaries and creating constraints on teams, it just sounds like heavy-handed stuff that’s going to slow us down and certainly stifle innovation. I remember I was talking with somebody at a tech company, and we were in Paris, France. They have a very laissez-faire attitude there. Hence, the French word, the hands-free mentality, where we just let you do your thing. And they were pushing aggressively against having any policies or any constraints or any process that we’re trying to provide and that we had seen succeed with other groups. And they said, “You’re killing our innovation. You’re going to turn us into robots.” And I remember hearing that and saying, “We don’t want to stifle your creativity, but we want you to be creative on the important things.” We want to create boundaries around the minutia, around the trivial things. I don’t want to come up with my own way to go through my checklist in the cockpit for my ground checks, right? I want to do that exactly how the 50,000 other pilots before me did it so that I’m not taking any chances in the air. But then as I get more refined as a pilot, I want to be able to apply my creativity and look at how I can do that engagement more effectively. So, along those same lines, when you’re leading 1,000 people, how do you create boundaries but at the same time still ensure that innovation is taking place?

Elroy: You talk about boundaries, and more often than not, people do exactly what you just did and think about limits, limits on what we can do. But you can also open those limits. And one of the ways I did that with all of the teams I worked with was I very clearly said in the beginning, “If you find a problem, find a solution.” And that may sound like a simple statement, but too often, as we’re out in corporate America, I go, “Hey, you know the problem’s there, why didn’t you fix it?” And I hear, “Well, that’s not my job. That’s not in my job description.” The perfect example is this, I call it the soda can test, put a warm open soda can about half full out in your squadron, in your business, in your organization, and watch and see how long it is before it’s picked up.

Elroy: If people have that attitude of, “It’s not my job,” they’ll walk by and see it and go, “Somebody left their Coke there.” Then you may find those people in the middle that’ll test it, that’s the reason I said a warm one, they’ll pick it up and go, “Ooh, it’s kind of warm, somebody probably needs to pick that up,” and they will keep going.” Or you find those people that know that office is theirs and they own the success of it, and they will come by, see it, pick it up, realize it’s not cold, and go throw it away at that point. That’s how you determine the mentality in your office. Because if you ask, they’re all going to tell you what you want to hear. So, you have to have those little tests to go, “Do people fix things that think it’s not their problem?” Or, “Do they fix everything they find that’s a problem that makes us better as a team?”

Thor: I think it’s very insightful that you’re not leaving a half full beer can in the fighter squadron, as well, because there’s just as likely a chance someone’s going to walk by and pick it up and drink it.

Elroy: That’s right. That’s right. It’s really for the safety and success of everybody.


Thor: Exactly. What a good test and something we can take away to the corporate teams as well, make sure that they’re leaving the campsite better than they found it. We heard that again and again in the military, that’s such an important thing to do. You talked about empower, you talked about motivating your team, building that alignment, let’s talk about how do you now set them up for success where you have to go hands-free. You didn’t shake everybody’s hand with 7,000 people when you’re leading them across the globe, remotely dispersed teams. How do you equip them with the tools to go execute your intended effects along the way?

Empower the Entire Organization

Elroy: So, I look at that twofold. First of all, it’s like our instructor pilot getting us ready for that fourth ride solo. They gave us the tools, they gave us the experience, and they knew that we would be successful before we went out and flew. You have got to do the same thing with your team, because you know that the ultimate measure of a leader is not just the success of your organization, it’s how much you empower and equip those below you to take over for you and be a better leader than you were down the road. They need to know that you are taking to heart their development, that you’re growing them as a leader, as a part of your team, and then also think about communication. I call it two up, one down. Every time people are in a room and they walk out, they assume everybody else in the organization knows everything they do.

Elroy: Whenever I walk out of a meeting, I want to know that I make sure the information goes two echelons above me. If you do that, you’re watching out for your boss and your boss’s boss. But don’t forget about those below you. When you walk out of a meeting, make sure everyone one echelon below you knows what went on and where the organization is going. That’s how you equip them with the knowledge to be successful down the road, so they don’t get blindsided by a change in direction. It goes back to having that crystal-clear picture of where the organization is going. When it’s updating and in every meeting with expectations, you need to communicate two up, one down through the echelons of the organization.

Thor: You bring up an interesting point. It reminds me of a conversation I had last week. We work closely with the MIT Sloan School of Business. There’s a professor there that’s on our board and that we interact with on a pretty frequent basis, and he was telling me about this study that they just conducted. They were looking at companies that are larger than 1,000 people and asking them, “What is the company vision? What are the three top priorities for the organization?” And when they’d asked the C-Suite that, everybody in the C-Suite would be able to answer that question. They’d ask the middle management, and then they’d also ask the people closest to the action, closest to the frontlines. I’m just setting you up for this so you don’t know where I’m going to go with it, but I’m just going to see if you have some intuition for it. Where do you think the biggest breakdown occurred in that communication? Was it from the C-Suite to the middle managers, or was it from the middle managers to the frontlines? What do you think?

Elroy: This is an easy one, because we see it in organizations we’re in all the time. The C-Suite is always motivated and knows exactly where they’re going. The lowest level of echelon is motivated in what they do every day. It breaks down at the middle management level, the ones that are charged with relating the vision of the organization to the tactical execution. It’s the breakdown between those two, which is when businesses aren’t successful.

Thor: Yeah. And I didn’t set you up for it. That’s exactly the answer though, and I’ll tell you the numbers. They said that when they asked the C-Suite… Like I said, 100% of the C-Suite knew what the three priorities were. They asked the middle managers, only 22% of the middle managers knew what the top priorities were. When they asked the people closest to the action on the frontlines, 18% of them did, which just goes to show you that the breakdown typically occurs from the mouths of the people that know it the best, from the C-Suite, even though they figured that they’ve communicated it 100 times, it still hasn’t been captured by the middle managers to the extent it needs to be, to be passed down to the rest of the team. And look at how strong the communication is between the middle management and the frontlines, which makes sense because you think they’re working together very often and they actually have a pretty strong execution rhythm. It’s the key leadership at the top that’s kind of in the ivory tower that is not communicating effectively enough.

Elroy: So, if I could give an example… As I give examples, most people assume it’s going to be a military one, this one’s not. Recently I had the opportunity to go to Manhattan and sit with the CEO of a $12 billion company, $12 billion of market cap. Happens to be, he has 7,000 people working for him, same as in my last job in the military. And I looked at his vision. My first meeting was sitting down with him and saying, “Where is your vision of where you’re taking this organization?” And then I went out and talked to his C-Suite, and I said, “Where do you think his vision is?” And I said, “I want to go out and talk to the lowest levels of the company.” And one of his C-Suiters said, “Let me give you an example. Last Christmas, we shut down. Our entire organization shut down, the entire market shut down. Over the holidays, and said, ‘Go spend time with your families.’ The leaders said you will not come to work.” They actually gave him an order to go home.

Elroy: One of the executives forgot her computer, so she swung by the office on the day before Christmas, and she was walking up to get in the elevator and the mailroom clerk was walking out with this huge box in his hands. And she said, “What are you doing here? Didn’t we say everybody had to go home?” And he goes, “Let me tell you why I’m here. I know what our vision is for the next year, and these are the samples. If everybody else in our corporation, in our industry is taking the week off over Christmas, I want our customer to see our samples when they walk back in at the beginning of next year. If I don’t get these samples in their hands, we will fail to make our market goals for next year.” This was the lowest-ranking person in the company. It was the mailroom clerk, and he sat there in the elevator and explained to her how the success of a $12 billion company hinged on him mailing this on this one day.

Elroy: If you don’t think that translates vision to tactical action… I mean, that brought a tear to my eye and it’s a better example than we even use in the military. And I told the CEO that and said, “You are completely running this like a fighter squadron, and that’s why you’re going to be successful.”

Thor: And the biggest challenge that CEOs will bring to us, they’ll say, “We’ve got this great strategy… ” We know behind the scenes, they really don’t. We can help them refine that. But they’ll say, “We got this great strategy. We’re just not seeing it connect to the daily execution.” And I always push back at them at that point and challenge them on how well they’ve communicated it. For me, it typically falls into one or two categories. One, they haven’t communicated it enough. If the average human needs to hear something seven times before they remember it, and I’ve told you this four times already, Chris, but you haven’t remembered it up until now. But I guess I got three more to go. And then the other one is they haven’t made it succinct enough, haven’t made it concise enough for them to digest it in one sitting. In other words, they have this big, huge, grand strategy they’re pursuing, and nobody can remember all 49 different pieces of it and be successful. Have you noticed anything else that occurs during that breakdown in the communication?

Elroy: I think you hit a good example. If I could give one military example. When I was in Afghanistan, we were in seven locations around Afghanistan. And myself and my chief of strategic thought flew to every person in the 1,000-person organization, and we gave them our mission brief, our vision of where the organization is going. And once they heard it directly from us, we said, “From now on, if you’re in a room and when a distinguished visitor comes in, we will point to you and go, ‘You can give the mission of the wing.'” And it empowered them to understand where we were going, why we were going there, and how they fit in. And that organization achieved more success because of the communication, because they understood the reasoning that went into our decisions, why we were choosing that as a goal, and how they executed toward that goal. That is the biggest thing. It goes back to two up, one down. And everybody in the organization communicates two levels above and one level below. We don’t have that middle management problem of translating vision to tactical execution.

Thor: Love it. So, we’ll wrap up. I want to give you the last word. Any parting thoughts on how you see connecting, what you’ve learned in your vast experience to the biggest needs of corporations? What would you leave with our listeners?

Elroy: The biggest thing I would say is the power of passion. When you talk, be passionate. Going back to the CEO, when I asked him why he did what he did, and if he enjoyed being the CEO, he leaned to the front of his chair, and I thought he was like a young new hire in the company about how excited he was. I could feel his passion, and it resonated through the organization. The same thing as military leaders. When we lead an organization, we know that lives are on the line and we have to understand and translate our passion to everybody else. If you, as a leader, have that passion in your mission, in your success, you will empower those that work for you, that work with you, that work around you to have that same level of passion. Engage the power of passion of your team.

Thor: Well said. Well, Elroy, thank you so much for joining us today. Great insights. What an incredible career and experience you’ve had. Happy to have you on the Afterburner team, and helping to lead the way behind the scenes with corporations today as well. Looking forward to having you on again. You and I both know you’ve got an even more amazing story to share on a future podcast. We won’t give the details of that right now, but there’s some exciting, interesting insights that we’re going to be putting out there from that experience.

Elroy: And incredible lessons learned that came from that experience.