Know Your People — This is perhaps the hardest of all the lessons, and one I think about all the time. I worked for many leaders that had no interest in me as a person. I was there as a cog in the wheel, just as replaceable as anyone else. It’s hard to be motivated when you feel like a cog. One of the best leaders I ever served under was someone who really knew us all. He knew our families, what drove us, our backgrounds, and he built a real culture of trust. Knowing “your people” also includes knowing those that you see but don’t manage every day. Teams are made up of a lot of critical roles, many of them in support roles or back office roles. Real leaders appreciate the contributions of the entire team and go out of their way to get to know all their people.

As a part of my series about “Life and Leadership Lessons Learned In The Military”, I had the pleasure of interviewing Tom McAndrew. Tom is the Chief Executive Officer for Coalfire. He is recognized as one of the world’s leading cybersecurity experts in both the commercial and government sectors. Mr. McAndrew joined Coalfire in 2006, and since that time, has held key leadership roles spanning Sales, Operations, Service Delivery, and Technical Testing, most recently serving as the company’s COO. Prior to joining Coalfire, Mr. McAndrew had a distinguished career in information security and weapons systems for the Navy; he still serves in the Navy Reserves. He has worked for the Space and Naval Warfare Command, Office of Naval Intelligence, National Reconnaissance Office, Office of Naval Research, and has made deployments in support of overseas combat operations. Mr. McAndrew is a graduate of the United States Naval Academy, holds a Master of Business Administration degree from the University of Washington, a Master of Science degree in Information Technology from the University of Maryland, and a Master’s certificate in Space Systems from the Naval Post-Graduate School.

Thank you so much for doing this with us! Can you tell us a bit about your childhood “backstory”?

I grew up in Bellevue, Washington. I learned to become independent early in life, since about the 8th grade — my mother, a Japanese citizen who moved to America at 28, raised two children on her own after she and my father divorced and he moved out.

I was always active in sports: I earned two blackbelts (Tae Kwon Do and Arnis — Filipino knife/stick fighting) and was recruited into Interlake High School football. I enjoyed school and was class president, graduating valedictorian. I chose to go to the Naval Academy and begin a career in the military.

I am married, with three children. I met my wife in pre-school, though we didn’t start dating until high school. I have one sister, Lori, who lives in Barcelona, Spain. I am passionate about Nintendo, sports, computers, music, and car stereo systems.

And what are you doing today? Can you share a story that exemplifies the unique work that you are doing?

I’m the CEO of Coalfire, one of the largest cybersecurity advisory firms in North America.

Cybersecurity is a huge challenge today; breaches and vulnerabilities are in the news every day. I’m responsible for building an amazing team that supports more than 1,800 clients with their challenges. This includes everything from assessing enterprises’ cyber risk, to helping an organization rebuild trust after a breach, assisting large cloud providers with security programs, conducting penetration testing, and more. Since we don’t resell products, we are unique in that people are buying our services solely for the great people we have and the objective guidance they provide. I spend a lot of time out in the community, such as supporting the Federal Trade Commission on their hearings on Competition and Consumer Privacy. I’m also on the board of Cascadia College Foundation and a Board Advisor to the University of Washington Center for Information Assurance and Cybersecurity.

I’m also still in the Navy Reserve, serving as a Commander with the Office of Naval Research. One of the areas I’m passionate about is giving back to the community and encouraging junior and senior high school students to stay engaged in STEM. I have supported several sciences fairs as a judge. I also support a motorcycle riding training non-profit.

Can you tell us a bit about your military background?

I graduated from the Naval Academy in 2000 and became a surface warfare officer. After completing training in Newport at Surface Warfare Officer School (SWOS), I reported to USS Peleliu, LHA-5. This is a large helicopter carrier, over 800 feet long and carrying around 3,000 people.

I was four weeks into my first deployment when the tragic events of September 11th, 2001 occurred. Peleliu was in the port of Darwin, in Australia and we were sent to the Persian Gulf to launch the initial combat forces into Afghanistan.

On Peleliu I served as a Deck Officer (think of the people that drive the ship, lookouts, maintenance), and then served as the Fire Control Officer (ran the ship’s weapons and combat computers), and was a Tactical Action Officer (TAO), which meant I was the senior officer on watch responsible for protecting the ship against attacks.

Can you share the most interesting story that you experienced during your military career? What “take away” did you learn from that story?

One event that I think about quite frequently is when we were on our way back from the Persian Gulf. I had just completed my second deployment and we were wrapping up a seven-month tour. We were in Guam to do a required “cleaning” of all our vehicles before heading back home. While we were transporting the tanks, one of them fell off the transport ship and sank to the bottom, killing the Marine inside.

There are three things that stuck with me:

1. We often overlook the risks at the beginning and end of events. It’s common in life, business, sports, etc. There is so much focus on the middle, and it is just human nature to get tired or complacent at the end. If you are in a leadership role, you need to ensure that the team has focus all the way through.
2. Sometimes there is just nothing you can do. We like to believe that we have more control that we actually do. In this case, once the tank fell, there was nothing anyone could do. We had a short amount of time, and there were no practical options to save him. Often, we like to take shortcuts on training or planning and leave it to people to figure things out on their own, but sometimes they will face situations where there are just no good options.
3. Finally, I think about how everyone is connected to other people’s lives. We all touch our families, friends, and co-workers in ways that we may not appreciate. We also may not see them as interconnected human beings outside of their role.

I’m interested in fleshing out what a hero is. Did you experience or hear about a story of heroism, during your military experience? Can you share that story with us? Feel free to be as elaborate as you’d like.

Herb Bridge is one of my favorite people that I’ve ever met in my life. I think that he is a true hero. I had the pleasure of meeting Herb in the mid-90s. Herb was the co-owner of Ben Bridge Jewelers, a national jewelry store that started in Seattle. Herb served in WWII, Korea, and was a very successful owner. I consider him a true hero who made the world better. I have a particular fondness for Reserve officers (I’m still a Navy Reserve officer myself). People forget that most of humanity saw citizen soldiers — people who had farms, jobs, and a family and would be called away to support their countries’ needs. Today, most people think of the military as a full-time profession, but there are thousands who continue to serve in the citizen-soldier mentality. I won’t repeat Herb’s story (it’s an amazing life from an amazing man).

I will share a few stories I had. First, when I was accepted to the Naval Academy, Herb wrote me a letter congratulating me. Herb was not an Academy graduate — he was a University of Washington graduate. He heard of my story and wrote me a letter out of the blue. A Navy Admiral and CEO of a large company wrote a simple letter thanking me.

He also started a birthday club, where every year he would take out people that had the same birthday (anyone born March 14th, any year). He helped me get into my MBA class at the University of Washington and took me out to lunch. He was committed to sharing his knowledge with the next generation.

He was known as Mr. Downtown for all the philanthropic work he did to make Seattle a better place. I consider him a hero because he had a huge sense of purpose, of making the world a better place.

A Navy Admiral, a business leader who was coached by Warren Buffet, and a great community legend.

Based on that story, how would you define what a “hero” is? Can you explain?

A hero is someone who is called to a higher purpose, who makes sacrifices in their personal lives to be ready for the call. A hero is the result of a series of conscious decisions that someone makes, each getting them closer to their ultimate purpose.

Does a person need to be facing a life and death situation to do something heroic or to be called a hero?

Definitely not. The movies glamorize life and death situations because they make good drama, and there are many life and death situations that are great stories for us to remember. But a hero is not usually made in just a single event; they happened to be heroic in that situation because they prepared themselves mentally and physically for that moment.

Based on your military experience, can you share with our readers 5 Leadership or Life Lessons that you learned from your experience”? (Please share a story or example for each.)

1. Know Your People — This is perhaps the hardest of all the lessons, and one I think about all the time. I worked for many leaders that had no interest in me as a person. I was there as a cog in the wheel, just as replaceable as anyone else. It’s hard to be motivated when you feel like a cog. One of the best leaders I ever served under was someone who really knew us all. He knew our families, what drove us, our backgrounds, and he built a real culture of trust. Knowing “your people” also includes knowing those that you see but don’t manage every day. Teams are made up of a lot of critical roles, many of them in support roles or back office roles. Real leaders appreciate the contributions of the entire team and go out of their way to get to know all their people.

2. Sense of Purpose — One of the things the military does a great job of is instilling a sense of purpose. From “taking the hill” to connecting to a rich history. It’s why so many senior citizens are wearing a baseball cap from their command. Serving in the military is one of the most important things they have ever done. It’s much harder to do that in the business world. It’s hard to develop that same sense of purpose when you are spending your days on phone calls and emails.

3. Simplify — Great leaders are great simplifiers. The challenge is to pick the three things that really make a difference and ensure that everyone knows them. As Albert Einstein said, “Make things as simple as possible, but no simpler.” Simplification is part art, part science. Great leaders take complicated ideas and thoughts and synthesize them into clear, concise statements. One business example we just wrapped up was “hire 100 in 100.” It was a company push to hire 100 employees in 100 days, something we had never done. But we embraced it, and got the entire company focused around that goal (and met it).

4. Do the Right Thing — Some call this integrity, others call it morality. Whatever you call it, you should always go to bed at night knowing that you did the right thing. The hard part about doing the right thing is it is rarely a black or white decision. We live in a world of grey, and you constantly have to make decisions with the information you have available. Sometimes you are right; sometimes you are wrong. Sometimes your mistakes will hurt people that you care about. But you always need to do the right thing and develop a moral compass to make those decisions.

5. Assume Good Intent — I remember when I first reported to my ship — there was an old, salty officer who basically told me that I should assume that everyone is lazy, untrustworthy, and needed constant oversight. As a young officer checking into my first ship, I was as naïve as any other junior officer. After about 90 days onboard, I understood his feelings. It seemed like no matter how much you trusted in people, you would always be let down by one or two outliers. So, you can either assume that you are working with the outliers or assume that most people are trying to do the right thing, and you’ll occasionally be wrong.

Do you think your experience in the military helped prepare you for business? Can you explain?

My experience helped me prepare for business, but not in the way that most people think. As I went through the military, I was always thinking about how it might apply to the outside world, and I consciously chose roles in the military that would help with the business world. For example, in the Navy you rotate from sea duty to shore duty, meaning after you spend a few years on a ship, you usually spend a few years in an office. Most people are burned out from their deployments and want an easy job to relax and see their families. Many of my friends took cushy jobs in San Diego, where they taught a few classes and played basketball. I chose to move across the country to Virginia Beach and get experience behind the scenes, working at Naval Sea Systems Command where they built and supported the software and hardware that went into Fire Control systems. It wasn’t a cushy job, and since my customers were the people on ships, I understood how important it was to get our job done right. I picked a command that had mostly civilians to get used to working with civilians, and I also went to school and earned my Master’s degree on my own time. I realized that I had done so much good stuff in the military, but on paper, I was behind my peers. I looked at my resume from a civilian point of view and realized that I needed additional school and certifications before I got out. If I had not completed my schooling and gotten my cybersecurity certifications before I interviewed, I would never have gotten a job. Many veterans wait until they are out of the military to go to school, and by then, it’s too late. They will accept a low-end job when they get out and may find it very difficult to get the career they had hoped for.

Some people assume that if they spend a few years in the military, it will somehow jump start their careers automatically — not true at all. There are thousands of veterans who get out every year who realize that the unique skill set and military life they have lived does not translate at all. If I had just relied on my military experience, I would be a tug boat operator, not a CEO of a cybersecurity company. The military doesn’t prepare you for life in the business world; you have to take your military experience and consciously apply it to the business world.

As you know, some people are scarred for life by their experience in the military. Did you struggle after your deployment was over? What have you done to adjust and thrive in civilian life that others may want to emulate?

While I certainly never had the challenges that many of my friends had, transitioning back was not easy. In the Navy, we have the luxury of working our way back slowly because we are on a ship and it takes about a month to get back home. You slowly transition back and work out from a combat mentality to a civilian mentality; that certainly helps. The military has learned this, and many people have to take some time off in Germany before being flown back to the U.S.

I remember the first day back in San Diego. I was walking through the shopping malls and I had this tremendous sense of guilt. It was sunny outside, people were just going about their business, and I thought to myself “they have no idea about the thousands of people that are on the other side of the world, putting their lives at risk.” I remember thinking how superficial everything felt, and quite frankly how spoiled we are. For me, I turned that guilt into drive. That I had a unique perspective of the world that others didn’t. It drove me to focus on making the world better and feeling that I had an obligation to serve, to never feel guilty because I didn’t take advantage of my God-given talent and the amazing opportunities I have as an American.

Are you working on any exciting new projects now? How do you think that will help people?

I’m lucky because I work in the “unsolvable” world of cybersecurity. It’s a complicated world that is at the center of all we do. You can’t open a newspaper without hearing about a data breach, hackers, or private data that was used inappropriately.

Today, I’m working across several fronts to make our lives better. At the national level, I’m working to improve the relationships with our international partners, including supporting the Asia Reassurance Initiative Act (ARIA), designed to advance our national security and economic interests in the Indo-Pac region, specifically, supporting the cybersecurity initiatives.

I’m also working with the industry to improve the security, transparency, and resiliency of technology companies. Coalfire works with some of the largest technology companies such as Amazon, Microsoft, IBM, Google, and many others. The work we are doing will impact everything, from e-mails to cars to refrigerators to the military. Just know that our team is working hard every day to try to keep your data safe and secure.

What advice would you give to other leaders to help their team to thrive?

Someone once told me “there are no smart people.” By that, he meant that you should believe and trust in your own judgement. There is no shortage of consultants that want to charge you money for their advice on how to build “high-performing teams.” But every scenario, team, and business is different; you were picked for your leadership role because others trust in your judgement. Take control.

What advice would you give to other leaders about the best way to manage a large team?

One piece of advice I was given was not to be afraid of larger teams. As a manager, you shouldn’t have more than eight or so direct reports, so if you manage 8 or 8,000, it’s not a whole lot different. Your world is pretty consistently those eight.

However, as you deal with larger and larger teams, you need to think further out. Strategy becomes more important — thinking one year, three years, further out. Also, you need to have a strong understanding of the competition and what they are doing.

Finally, your communication style needs to change. Simplifying your message and driving focus is a critical role. I constantly tell my team that great leaders are great simplifiers. It’s easy to give eight people eight things and track nearly 100 items. It’s much harder to think strategically and focus on the three things that will really move the needle in your business.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

One of the best leaders I ever worked for was Adam Gregory. Adam was a Senior Chief who technically reported to me. As a 24-year-old responsible for running a team of 30 technicians, Adam was the senior enlisted leader. It’s weird when you are in charge of someone who knows more than you and is nearly double your age and calls you “sir,” but it’s the way the military works. Adam was one of the hardest-working guys I’ve ever met. While on Peleliu, we were on the way into the Persian Gulf, passing by a ship on their way out of the gulf. We realized that our sailor on Peleliu had a husband on the other ship and we were going to pass right by each other. They were going to be apart for a year and be within a few hundred yards of each other on the other side of the world. What could we do? We got sailor on an inflatable boat and onto her husband’s ship to reunite. Good leaders go the extra mile for their employees and mission, inspiring true loyalty and engagement along the way.

How have you used your success to bring goodness to the world?

As I get older, I spend more and more of my time giving back. I think that when we start our careers, it’s all about us — about advancing, making more money, taking care of our families. When we get older, we realize it was never about us. I love Mother Theresa’s “Do Good Anyway” poem, and I have it hung in my office and at home.

I’ve been spending more time giving back to my community. I particularly like to focus on areas where there are less affluent people. Community colleges are a great example. At Cascadia, where I’m on the foundation, there are many people who don’t complete school because they can’t afford little things like parking passes, books, etc. Education has been a huge factor in my success, and I hope that I can give that chance to someone less fortunate. Through my efforts at the college and personal donations from myself and friends, we have given more than 50 scholarships.

I’ve also recently been much more active in motorcycle safety. I love riding motorcycles, but there is some inherent risk. Most people have never had much training, and it make a huge difference. 28,000 motorcyclists died from 1990–1999; 50% was due to negotiating a curve, and another 25% was due to braking and steering. Safety training makes a huge difference and saves lives.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I wish we could do more for non-traditional students. Many people who have jobs today are in dead-end jobs or jobs that may be replaced by technology in the near future. However, most technology jobs are hard to get into, hard to get started, and hard to transition to mid-career. We need to get better at workforce retraining and give working adults the chance to make their lives better.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“In preparing for battle, I have always found that plans are useless, but planning is indispensable.” — Eisenhower

I have thought about this quote frequently and use it to ensure that we have good plans but realize they may need to change the second we start to execute. It’s a fine balance between needing more information and going through “paralysis by analysis” and just “winging it.” Leaders have to know when to charge the hill and adapt, and when to hunker down and plan.

I’m also fond of “he who defends everything defends nothing,” a Sun Tzu quote. It’s important to drive focus and attack/defend only a few business fronts. Most people go too broad.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them 🙂

I’d love to spend some time with Valentino Rossi, but otherwise Warren Buffet would do ☺ I love Rossi because he is a legend and built a legacy in an industry that didn’t really have legacies (at least not like Rossi). I love Buffet because I love his focus and the way he simplifies things. I’d also love to meet with any successful Naval Academy graduates. I’m always inspired when I meet with them.

Thank you so much for these amazing insights. This was truly uplifting.

Heroes Among Us: “Know Your People” With Coalfire CEO, Tom McAndrew was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.