Built to lead: Lessons in Military Leadership

Updated: Feb 21

Questions for a Leader

Podcast Guest

Last night I had the privilege of being a guest on another podcaster’s show, Vitamin Lead with TJ Reid. This isn’t the first time that I will be a guest rather than playing the host and it is always interesting to see what I can learn from the experience. After all, it’s not every day that you get to reverse roles and be the one getting asked questions rather doing the asking.

What I have learned most about myself after this most recent interview is that I have been extremely blessed by the Air Force and the direction that my career has taken me, the people that I have met along the way and the places that I have been able to see, that my leadership perspective is truly unique and one that is my own.

TJ’s show is great, a quick hitter with interesting guests coupled with his genuine interest makes for a smooth listen. On top of that, like any good leader, he is prepared. TJ does his homework when it comes to his guests and I was no different. Not only had he listened to Vet Pivot, but he knew about my time as a Military Training Instructor and my coursework with the Massachusetts Institute of Technology. For some that may be off-putting, that their life details can be found so readily is a sign that maybe they are too engaged in the internet. However, for me, it was exciting to see that someone had taken an interest in my career, found it to be noteworthy, and asked me for my perspective because they saw the value in that. I also have a tremendous amount of respect for any professional that commits to their craft and takes their work seriously.

Three Questions

The Hat

The interview with TJ could be broken down into three questions that stood out to me. The first of which had to do with my time in the military and how that shaped me as a leader. I was asked about my time as a Military Training Instructor, and what that meant to someone that has never been in the military. In the simplest analogy that I can use, every single person has an introduction to a new job, where they go through training and learn the ropes so that they can fulfill their duties. For most people, there is a person that they train with that understands how to do the job that they will be doing. In the military, that person is the Military Training Instructor (Drill Instructor/Sergeant in other branches).

What TJ wanted to know was simple, what is the biggest thing I learned from my time in that role. This got me thinking, how do you sum up five years of the rawest, soul-searching, life-changing assignment that I had in my military career into one lesson in leadership? The truth is you don’t. So, what I gave as an answer is that I learned something about myself and I learned something about people.

1. I had been wasting a lot of time in my days. This was the thing that I learned about myself. When I got to basic training to be an instructor, I quickly realized that the instructors that I aspired to emulate could fit a metric shit ton of training activities between the hours of 0445 and 2100. How? They simply broke everything down into 15-30-minute blocks of activity and tackled one thing at a time. It may sound simple, and that is because it is. However, this approach to your daily routine takes discipline, because there will not be some crazy person with a big hat getting in your chili if you break schedule compliance. When I started to apply that to my goals and my work routine after my assignment as a Military Training Instructor, it was like I could finally see the damn matrix. I was friggin’ Neo, and I was kicking ass.

2. People are not one size fits all. Perhaps one of the hardest lessons was that you cannot lead people the same. Each of us has the default to wanting to lead people the way we would want to be led. This is a falsehood, however, and one that will get you into some predicaments as a leader that could end up costing you the respect of your followers. Every single person requires a different approach to being led in order to achieve the ultimate leadership outcome: inspiration. To inspire someone to follow out of commitment rather than compliance is the one true test of your leadership, and that will incur a cost to you as the leader. What does that cost? You must learn your people, what makes them go, and determine first how you can serve their needs rather than making them serve yours.

The Scholar

To say that I was a late bloomer in school would be an understatement. It took the discipline and maturity that I gained from the Air Force to prepare me to tackle my education. It’s something that I still kick myself over to this day, “Why were you such an asshole as a kid? Why didn’t you take your parent's and teachers' advice to heart and apply yourself? You thought you were so damn smart, dumbass.” Running this dialogue through my head constantly eventually turned into motivation when I applied my new core values ingrained in me by my Military Training Instructor.

As I progressed through the ranks prior to my time as an instructor, I tackled school slowly yet surely. I was on track to finish at somewhere in my fifteen-year mark. By the time I got to San Antonio and started leading flights of trainees at basic training I was halfway through my bachelor’s degree. During my time wearing the hat, I did not take any school. The demands of the job left no time for personal achievement, especially as a rookie instructor. It wasn’t until I had been there for almost three years that I finally felt comfortable enough doing the job and school at the same time. Make no mistake though, as I was in the matrix, and I crushed course after course in order to accelerate my education timeline.

I had accelerated so much that by the time I hit year eleven, on December 28th while my third child was being born, I finished my undergraduate degree. Yes, you read that correctly, I finished the degree in the delivery room while my wife was in labor and an hour before our daughter was born. I cut it close too because I was signed up for my graduate degree and had been accepted into Purdue University’s Master of Science IT Project Management degree program.

During that program I kept my foot on the gas pedal, knocking graduate work full time, working my Air Force job full time and being a family man full time with two of those rascals being in diapers. In the meantime, I still found time for the gym every day and some sleep each night. The trick was my schedule matrix of 15 to 30-minute blocks of productivity. I had gotten so good at this application that I enrolled in Executive Education at M.I.T. Sloane School of Management while still going to Purdue full-time. Maybe I was a glutton for punishment, but just like a good accountant, I had seen that my time had room in the budget for this investment and I was ready for the challenge.

I finished my master’s degree, and my coursework with M.I.T. on-time and graduated in May of 2019, just 15 months after I finished my undergraduate degree. That feeling of accomplishment was surreal, and I realized that I was capable of anything when it came to academics. I was so inspired to keep going that over the summer I was accepted into the Doctor of Technology program at Purdue and decided to take it on. I will finish in 2022 (or sooner, time permitting).

The Podcast

The last thing that we spoke about during the interview was the podcast. This one is easy for me to talk about because it’s the most recent adventure and one that I take an immense amount of pride in. Vet Pivot was started for one simple reason: to pay it forward. After all, I was seeing the matrix and I will have learned nothing about leadership if I kept that to myself.

Adam and I served together as instructors, brothers of the hat, and ultimately, he transitioned out of the Air Force before I did. When my time came to hang up my boots, I looked him up and we connected on LinkedIn. Adam was the first person not closely related to me to be a contact on the platform and for that, I was both grateful and inquisitive.

After talking on Zoom for a little while Adam kindly put me in touch with some awesome people. The one that stands out in my mind was Kevin O’Brien. Kevin and I chatted on the phone and had nice conversations about what I was after and what my resume and value were in the civilian market. What I appreciated about Kevin is that his advice and insights were second to none and he told it how it was. He was also in the area that I was looking to move to so that was a plus. Kevin went to work for me, helping me make connections and be strategic in my job hunt. Ultimately that led to an introduction to Bob Waldo.

Bob was a champion for Matt Kuchera. Like my very own hype man, I always felt like Bob was taking care of me. Much like Kevin, he was a straight shooter and never tried to bullshit me, which was refreshing from a person in recruiting. Bob worked for the company that was my number one choice for an employer and best aligned to my education, experience and interests. Within a week he landed me six interviews, four of which were interested in hiring me and one whose offer I negotiated and ultimately accepted. I was through the front door of my new employer within three weeks, and a month before my date of separation.

As I am often reminded, this is rare, and my job as Adam affectionately puts it is a unicorn. I feel blessed to have met the people that I did along the way who saw enough in me to give me the chance to be what I knew I could be when I was buried in books or under the hat for sixteen-hour days. I needed to pay that forward.

Vet Pivot is my pay it forward gesture. Something that I can use to give back to the community, to help guide the veterans that are out there and need a helping hand or a beacon to navigate with. Think of it as GPS for your military transition, but not with the stuffy British voice, rather more like the voices you used to be able to download to the old TomTom or Garmin devices (mine was Mr. T – “I pity the fool that misses this turn! Slow down, Mr. T don’t get no tickets!).

The transition process is hard and stressful. It is a time where we are walking away from security and the men and women that were to our left and right watching our backs. We go it alone, or so we think, and Vet Pivot is there to debunk that myth. We want you to know that we are here for you, that others have done it before you and that you can do it too. Oh, and it doesn’t have to suck, let’s have some fun while we do it: work hard/play hard.


I am extremely grateful. I am grateful for my family. I love what I do for work. I get a sense of incredible pride in helping the men and women who serve through Co-Hosting Vet Pivot. In so many ways I am a very blessed man. I have already begun shaping my legacy, digging my well if you will. Beyond that, I am excited for what is to come. I can’t wait to see where Vet Pivot takes me, to what heights we can climb. Where will I go with my career in my firm and the people that I will have the privilege of working with there? I marvel in the development of my children and how my wife leans into her maternal instincts as they grow up. I can look at my life and be damn proud of all that I have accomplished. It is a marker, a checkpoint that level sets me, so I understand where I have been successful as a leader. I’m leading myself and my life how I want it to be led. TJ made me think about that during the interview tonight. What is the biggest leadership lesson I’ve taken away from my life?

"You must be able to lead yourself before you can lead others. And when it is time for you to do so, you must lead them before your personal ambitions – to serve them humbly, only as someone who has already led themselves could understand."