An Encounter with Greatness
A chance meeting that opened my eyes to how effortlessly a true leader can inspire confidence and trust
I spent years as a crummy CEO. I said the wrong things, made stupid decisions, and treated people poorly. Then in 2012, I joined a CEO coaching group (Vistage) and began the long process of learning how to lead. In this group, we read a lot of books about leadership.
One of the more influential books we read was Simon Sinek’s Leaders Eat Last. In this book, Sinek explores why some teams pull together effortlessly while others tear themselves apart. The setting for his book is a company of United States Marines, who faced life and death decisions every day in combat in Afghanistan. It is a powerful book that I strongly recommend.
Leadership is like any skill, it requires practice to perfect. I spent years studying, practicing, and often failing at being a better leader. However, it was not until 2019 that I met a man, and a Marine, who opened my eyes to true leadership.
What Had I Gotten Myself Into?
I was at the RSA conference in San Francisco. RSA is a massive annual trade show for information security. A friend from Amazon Web Services (AWS) suggested I attend a meeting with a person he knew. He did not tell me much about the meeting. His only comment was that I would find the meeting interesting. Since I valued this relationship, I accepted the meeting.
The meeting was in an unusual place, the Marines Memorial Club and Hotel in San Francisco. Stepping into this building is like stepping back in time. The walls are covered with plaques and memorials to fallen Marines. As a student of World War II history, I found the pictures of battles on Guadalcanal and Okinawa fascinating. I even spotted a picture of John Basilone, a well-known World War II hero who was killed at the battle of Iwo Jima. I felt humbled to be in the presence of such heroes.
I made my way up to the conference room. There were about a dozen well-dressed people, all talking among themselves in the room. I immediately felt like an outsider. I sat there steeped in all my usual insecurities. I still had no idea who I was meeting or even what the meeting was about. I was starting to feel as if an ambush was awaiting me.
Then a man entered the room and the entire chemistry of the room changed. This person had a distinctive presence. He was an average looking man in a suit, yet he commanded the immediate respect of everybody (else) in the room. What had I got myself into here?
Executive Gravitas
He did not introduce himself immediately. He sat down and asked us to introduce ourselves. I had no idea who he was.
We went around the room. Each person introduced themselves and explained what their respective employers did. When it was my turn, I gave my standard pitch I had used many times before. However, the man paused and considered my words. He showed genuine curiosity about my business and what we did. He asked me numerous questions. Each question showed curiosity, yet also compassion for me.
I immediately trusted this man. He seemed genuinely interested in helping me.
It was only at the end of the meeting I learned that the man was General Vincent Stewart, deputy commander of the US Cyber Command. General Stewart had had a brilliant and distinguished career in the US Marines. Right out of basic training he had been promoted to command an armor company. He had risen through the ranks to become the first African American Director of the Defense Intelligence Agency in 2015. He had retired from the Marines in 2019 and served on several corporate boards. Sadly, General Stewart passed away in 2023.
I met General Stewart just once. Yet his presence has stuck with me ever since. He was the epitome of a person with “Executive Gravitas.” Over the course of a single meeting, I felt like he genuinely cared about my business and was a person I could trust. He was not boastful, he did not talk about himself, and he never once name-dropped people he knew. Instead, he asked questions, listened, and shared ideas. He spoke about what he valued, such as honesty and lifting others up. At the end of the conversation, he went around to each person and asked them “What can I do for you?” The genius of this question is that it made all of us want to work for him, rather than him working for us.
After this meeting, I spoke with some of the people who had served with General Stewart. “I would take a bullet for that man,” commented one person who had served with him. That is what true leadership can inspire.
Leading With Values
Up until that meeting, I had studied leadership, but had never experienced a true leader in action. Meeting General Stewart opened my eyes to how effortlessly an effective leader could inspire people and drive the mission forward. I resolved at that point to be more like General Stewart. To listen, encourage others, and stay focused on the mission.
My experience with General Stewart also reinforced how important it is to lead with your personal values. General Stewart did not merely talk about his values, he embodied them in real-time.
Soon after this meeting, I began talking about the values that I cherished, such as being bold, solving problems, and cultivating a diversity of ideas. Not everybody agreed with my values. However, many did. The more I discussed values, the easier it became to communicate and lead.
Moreover, values transcend personality. When you share values with people, you can connect with people who are nothing like you. This was a huge revelation for me, as I am a socially awkward person who struggles to connect with people.
General Stewart showed me that true leadership comes not from your title, the people you know, or the giant valuations you got on a term sheet, but from the values you believe. I am honored to have met him. He earned a place among those heroes in that hall.
This is an excerpt from my book, The Founder’s User Manual — Practical Strategies for the Startup Leader, which will be published soon at Amazon.com.
