A Personal Epiphany on Leadership

I recently had a chance to talk to a sales executive who was considering the CEO’s job at another company, a possibility about which he was very excited. He understood the risks but simultaneously expressed—with great confidence—the belief that he was a perfect fit for the gig. He thought he had all the necessary skills, and said he had family support.

It bears repeating: the most important part of being a great CEO is being a great leader. Team building, high team performance and maintaining high morale are really important elements of his current job, but these are a subset of the traits — among many more — which are required for the CEO job.

Putting aside his capabilities and qualifications as a potential CEO, he forgot to take the most important step on the journey, which is to pause for an unencumbered moment of self-reflection.

I learned to do this shortly after the acquisition of Black Duck. Begin with thoughts of somewhere special to you, for example think about your favorite spot on a beach, or that special resting place during a hike, or some other peaceful place. Approach the moment of self-reflection this way:

Tapping into your innermost self, answer the following questions:

1. what do I really want to do for work or in a job?,

2. who and what do I really want to work with?, and

3. how do I really want to conduct my life outside of work?

Begin with those, get your answers, and branch out from there. There are many other questions to follow, but this is an important foundation.

After Black Duck’s exit, I decided I wanted to focus on working with high-integrity entrepreneurs in their first or subsequent startups. I wanted to serve on boards and make real contributions doing things like holding regular and productive one-on-one Zoom sessions and meetings with CEOs, the ELT, and key company personnel.

I did not want to work with phonies.

I was particularly passionate about helping the next generation of leaders, and to share my operational expertise with them. As for my tech focus, I became driven to understand more of AI and ML, cybersec, dev tools—especially open source—and Kubernetes technologies and markets.

Finally but most importantly, I wanted to spend more time with my wife, kids, and friends. I realized that I had put my career ahead of these people and I needed to spend more time with them because I really valued them. (Another benefit: more fine wine and bourbon to be enjoyed.)

While there have been a couple disappointments,  I have to say I’m thrilled. Almost all of the startup CEOs with whom I’ve worked are wonderful in every sense of the word. (They know how I feel about them.) I can say the same for the board members, ELT, and others team members I’ve collaborated with. The technologies are fascinating and I love teaching at Harvard Business School, where interacting with students, working with prof’s, and preparing for each class is pure joy.

But it all started one day in February 2018 while I sat on a windowsill in the second-floor man-cave (aka my office) in my Boston house, pondering the questions I suggested above. Sun streamed through the window, and I was enthralled by a certain stillness. I could sense my heart beating … Then my wife passed by, saw me, and said: “Hey Rambo! You’re an operator! Go out there and help create some companies, help finance them, and then help them to exit. And get off my window sill. You’re messing-up my drapes.”

{Please note: This is Susana’s nickname for me. It was conferred on me by my colleagues at Javelin Software back in the day. No one else is permitted to use this nickname. I have an 18 inch Bowie knife to enforce that rule.}

A good reminder: that moment of self-reflection is necessary as is real-time decision making and assessing opportunities and threats. Find some peaceful and quiet place to ask yourself those three questions, and then get ready to go out and get at it.

Oh, and stay off the drapes.

---