Lessons learned from one headhunter’s three decades behind the scenes about calling, purpose, legacy, dual-use tech & national security

As a headhunter I ask lots of questions. I like to joke that I’m part headhunter, part connector, part psychologist, and part therapist. The questions I ask seek to gain insight into where an executive came from, the decisions and judgments they made along the way, what worked and what didn’t, and most importantly, what they still want to accomplish. Then I listen (with a constant reminder of the adage – two ears and one mouth, which I struggle with).  Here’s what three decades of listening to many thousands of investors, executives, advisors and national security officials have taught me about calling, purpose, service, impact and legacy. I am pleased to share lessons learned divided into 3 categories:  Philosophy; Leadership Lessons; Questions to ask yourself and your team.

1) Philosophy

Have a Vision for Your Career & Pivot When Needed

Before 9/11, I was focused on Bay area starts-ups and VC firms. After 9/11, I found my own personal ‘calling’ and purpose by deciding to focus on serving the national security community. My family and I moved to the Washington DC area in 2003 when I founded Benchmark to make our nation’s security, and those who served her, my life’s work. I traded a west coast network for a new mission: matching visionary tech founders with leaders who can preserve democracy and keep America safe. An inspiring corollary, my closest friend Scott had a calling to be an astronaut. In achieving that dream, he attended the U.S. Naval Academy, graduated among the top of his class, flew F/A-18’s, and during the production of the original movie “Top Gun” his squadron trained the Top Gun instructors that flew in the movie. After being disqualified from the astronaut program with a medical condition, he quickly pivoted to another goal which he accomplished. Scott would always say our focus should be “Mission over Me” and “Service Over Self.”   I wish more people embodied that philosophy.

What is Your Calling?

This is a deep question. Have you ever personally asked it for yourself?

The broad categories of your calling could include God, family, and country. Most people may immediately think of a ‘calling’ to serve a higher power. A calling is something bigger than yourself. Another way to think of a calling is “What is your Why?” After 9/11, there were countless very successful people who found their calling. Some were corporate executives, NFL players, and entertainers. Something triggered them to change their goals and aspirations. Here are other perspectives to consider. Some may think of a ‘calling’ as a service to our great nation. It is said there is no greater sacrifice than laying down your life to benefit a greater good. Napoleon said,

“Money motivates neither the best people nor the best in people. It can move the body and influence the mind but cannot touch the heart or move the spirit; that’s reserved for belief, principle, and morality. No amount of money will induce someone to lay down their life, but they will gladly do so for a bit of yellow ribbon.”

Legendary CEO headhunter Gerry Roche would ask candidates and colleagues what they wanted on their tombstone. Your true answer to that question will certainly change your perspective and help move past your to-do list this week or your quarterly goals and help you internally search for what really matters. Many corporate executives are exactly on the path of their choosing. But far too many others are climbing the proverbial corporate ladder to please somebody else or prove somebody wrong. When I ask candidates what job they would have if they hit a big lottery, very few say I’m so passionate about what I’m doing I would keep it the same.  

Legendary football coach Vince Lombardi explains it this way in his book about leadership. The root word of career is carrier (French for carrousel) which means “around and around.” He states that living a life of purpose and just having a career are typically very different. Your calling is at the intersection of a Venn diagram of three things: doing something you’re great at, feeling valued, and believing your work is making people’s lives better. When those three things line up, the impact can be exponential.

Reverse‑Engineer Your Legacy

Another deep question to ask is “What Legacy Will You Leave Behind?”

Most of our executive candidates do not leave a senior job to make more money.  Someexecutives and investors we speak with talk about reverse engineering the time they may have left. Their primary goal is to make a difference, do things that matter, create an impact or leave behind a legacy. Most of the former senior military and NatSec officials recognize that their service made a difference and the legacy they left preserved Democracy and the freedoms America has fought for. Fewer corporate executives have the “service gene” or talk about serving the greater good.

I recently heard someone speak on their definition of wealth. They said that instead of using assets or income (monetary measures) to solely define the metric for wealth, more people should think of this definition:  Your Service Is Your Wealth. To reverse-engineer your legacy is to envision something greater than yourself, and from that vision, chart your course, overcome the obstacles needed to achieve it. Find the right team to join or recruit, maintain your ‘North Star’ and empower each other to achieve success together. A good way to visualize your legacy is to envision what you want your tombstone to say.

Give More Than You Get

Among the wiser things I have heard about leaving behind a legacy came from a retired Admiral and war hero. He counseled that in life the only thing you can take with you is the legacy you leave behind. That legacy is built upon the relationships you’ve had throughout your life. He called it “relationship capital.” He said to think about it like this: imagine every relationship in your life (family, friend, peer, co-worker, your waiter, house cleaner and even strangers) being measured as you would a bank account. But in this case, money is not the currency of debits and credits. Credits grow in your account by your actions (listening, helping, complimenting, donations, taking time, taking care and lending attention and imparting wisdom) all without any expectation of a return. He advised that at the end of your life, the goal would be to have a “credit balance” with every single relationship in your life – meaning, “give more than you get.” He also suggested that we determine if each day is a “getting day” or “giving day.” He would allocate every Monday and Friday only to volunteer efforts or find ways to be of service to younger people. If more people led companies with this unique philosophy, they would achieve greater success and everyone would feel appreciated. He posed this question as well – would you be more fulfilled if you started another business or if you started a charity? Your answer may be a measure of your relationship capital.

Do What Matters

The great mathematician Richard Hamming would ask colleagues a simple question: “What are the most important problems in your field?”  Given the response, he would continue, “So, why aren’t you working on them?”  

What problems and opportunities matter?  Does it involve AI, quantum, autonomous systems, cyber, hypersonic weapons, or something else? Our values are under threat. Individual liberty, freedom of open debate, enabled scientific inquiry, and democratic accountability have produced more flourishing humans and society than any other political system in history. These values are under threat. If we want our values to survive, we must defend them.

2) Leadership Advice 

Trends in Seeking Your Next Opportunity

Over the decades, I have worked with and had the pleasure of getting to know many thousands of senior executives and hundreds of senior government officials. One trend that has remained consistent is that the high majority who transition careers choose the jobs that are merely available to them instead of holding out for what they really want or were meant to do. My former executive search mentor would tell candidates that you can’t accept the perfect job, life changing job, or even generational changing job, unless it is offered to you.

I would recommend making the effort and taking the time to get more data, gather perspective, rule out what you don’t want to do, listen, then choose wisely. I advise candidates to listen to their gut. Most people let their head talk their gut into making the right decision. I have seen too often that the head fails you, but the gut rarely does. I also encourage other headhunters to truly listen to their candidates’ desires, not just placing a candidate because it completes the search. Everyone will be better off if there is true alignment; this is how everybody wins.

Masters, Mentors, and Morning Routines

From my optic, most successful people are constantly seeking wisdom and knowledge from those that came before them. The search for wisdom (from Aristotle to Sun Tzu to Marcus Aurelius) dates back thousands of years but is just as applicable today. Strategies and tactics change and evolve but first principles are always foundational. In my experience, we have found that it’s the values behind a company’s mission and vision that ultimately define the true competitive advantage, separating the winners from the losers.

Most successful people have had a mentor(s) along their journey; someone who exemplifies or clarifies where they want to go, and who is willing to guide, teach, and challenge them. Whether living or not, most have had a ‘North Star’ that reminds them of the sacrifices to make and what their ‘why’ is. The most successful people are also disciplined in their morning routines; it’s sacrosanct to many of them. Whether they include exercise, journaling, praying, meditating, visualizing, or just putting aside time to be grateful for their blessings. Most start their day by carving out time for themselves.  

The morning builds the foundation for mission-driven success. As a Navy SEAL I follow says, “up before the enemy.”

Advice For Future Leaders

Know thyself. Learn your strengths, your management style, what you aspire to be. What key component of a team you can do better than anyone else? Ask yourself what job or skill would make you jump out of bed every morning? What mission or vision of a company can you truly get behind and enhance? What leader would you follow into a burning building?

Your values define your character, and nothing is more important. Strive to be a trusted, committed professional of strong character – your reputation depends on it. Find your path and become deeply knowledgeable in your position and area of expertise through continuous learning, education, research, and best practices. Then go beyond that platform to become a “thought leader” who creates foundations for knowledge in your field of endeavor, and who evangelizes important new thoughts, ideas, and practices essential to your peers and their success.  

If you or someone you know is just starting their career, encourage them to dream beyond taking on the titles of fighter pilot, general, admiral, Navy SEAL, or CEO. Invite them to also consider the path of a cyber warrior or tech entrepreneur, serving national security and building mission-driven solutions and capabilities. We need the best of the best in each of these roles, securing our country’s way of life, freedoms, and democracy; these roles take on many forms.  Our future, both nationally and globally, hinges on whether the next generation can solve the most vexing challenges facing our national security.  Regardless of your path, find your calling, be passionate about what you do, and make everyday count.

3) Questions to Ask Yourself and Team

• What mission, what calling, gets you out of bed every day?
• How, where and with whom can you contribute your unique strengths or calling to our country’s mission for national security and prosperity?
• Have you started building your “relationship capital” and enjoy the miracle of compounding?
• Do you have masters, mentors, and role models, and are you one to someone else?
• Are you more focused on your character than your reputation?
• Do you have a greater thirst for wisdom and knowledge, rather than power?
• Are you giving more than you are getting?
• Service can be your wealth, how wealthy are you now?
• Only teams win, are you on the right team?
• And finally, what one sentence do you want written on your tombstone?