Finding Your Voice as a Leader

Over the last few weeks, several founders have told me about a common challenge: how does one transition from building and selling to leading a team? There is plenty of advice out there about what a "good CEO" should do: hire the right people, point them in the right direction, and get out of the way. Yet despite knowing the rules, one client told me that it simply feels awkward to lead. He shared his worry about whether his team would take him seriously if he shared his vision with them. It would be far easier to return to the comfort of a functional IC role. Another told me a story about the anxiety he felt when, during an offsite, his team seemed to reluctantly follow an order during a competitive game of laser tag.

When I listened to these leaders, who had both built impressive businesses, I couldn't help but think about an experience I had in middle school. Some time in 6th or 7th grade, the Gifted and Talented class put on its annual play. That year, I was cast in a small speaking role. Despite the fact that I only had 2 lines, I was thrilled at the chance to get on stage and deliver them. But there was a problem. During rehearsals, the GT teacher - we'll call him Mr. H - wasn't happy with the way I spoke my lines. Try as I might, I couldn't figure out how to deliver them any other way, much less in a way that would satisfy Mr. H. You could sense his frustration grow steadily with each attempt. Eventually, Mr. H pulled me aside and said, "Brian, I'm really sorry, but I'm going to have to pull you out of the play. Someone else is going to take your place." As a 12 year old, this was devastating news that reduced me to tears. How could I have screwed up so badly? Was I not good enough? Will anybody ever take me seriously again?

That moment shaped my ability to assert myself and take up space as I grew older. It deeply affected my self-esteem to a degree that I did not realize for a long time. The lesson was: if you don't do things right, you will be taken out of the play and literally lose your voice. And if you cannot speak your voice, then you fundamentally cannot belong.

In that search for belonging, I eventually started a company. I built a product, one that would be a reflection of myself, in the hopes that others would make me feel seen and heard. Over time, our traction let us assemble a team, which brought me to that same place my clients are today. That place where I could no longer hide behind building a product and would have to face my childhood battle for others to hear me once again.

The struggle to assert oneself forces us to confront the question, "Why should anyone take me seriously?" Or more to the point, "Am I good enough to be taken seriously?"

Many founders, somewhere along the way, learned to doubt their ability to make a statement to the world. And yet, at its core, entrepreneurship is an assertion. It is a strong belief that you can make the world better. When other people join your team, they do so because they agree with that belief. So why do we struggle with the notion that the people on our teams will follow us?

Here is what I have to offer when you find yourself in this position:

  1. First, pause for a moment and ask yourself where your hesitation comes from. A useful question is, “What is the story I’m hearing in my head right now?” Be patient but persistent here - you probably won’t get to understanding in just a few seconds.

  2. Connect back to why you took on this challenge in the first place. I don't mean the part about boosting your self-worth but rather, the true purpose behind the product or service that you put out there. That purpose is likely what attracted your team in the first place.

  3. As Jerry Colonna might say, remember that you have a right to take a seat at the head of this table that you set yourself.

  4. Recognize that when you are caught up worrying about what your team will think of you, you are actually preventing them from doing their best possible work. Without clear direction and connection to purpose, the team will keep working hard but you may not like where it takes you. So if anything else, focus on serving your team before serving your ego.