Five Things I’d Tell My Younger CEO Self
And the one practice that would have made all five easier
Someone asked me recently what I’d tell myself back when I first held the CEO title. The five things below are my answer. None of them are complicated. Each one took me years, and more than one company experience, to learn. I spent almost twenty years in the CEO seat across three very different organizations: a music company I founded in my San Francisco apartment, a company whose founder hired me to run what he had built, and a climate nonprofit that took a delegation of U.S. governors to the signing of the Paris Agreement. For the last seven years I’ve coached CEOs and founders through the same terrain. Here’s what I wish I’d known sooner.
Relax your grip on the wheel.
In a startup you have to put in the effort. There’s no way around it. But effort has a point of diminishing returns, and past that point it starts working against you. Relaxing your body, your mind, and the people around you isn’t the opposite of sustained effort. It’s what makes sustained effort possible, and it leaves room for the creativity, connection, and fun that pressure tends to squeeze out.
1
Connect more deeply with the person in front of you.
2
Meeting to meeting, task to task, it’s easy to forget the human sitting across from you. Slow the conversation down. Listen to hear, not to respond. Most of what I’d call my mistakes as a CEO happened when I was moving too fast to see and be present with the person in front of me.
Seek more audacious counsel.
I had advisors, board members, and investors. What I didn’t do enough was ask the people who felt out of reach. Their view would have given me a bigger picture of my business and the opportunity in front of it. So my advice: Make the ask. Almost everyone says yes. And when the counsel isn’t right for you, listen, assess, then trust your gut.
3
Know when to hit eleven.
It can’t be an eight or a ten all the time. You need to be able to push to eleven, and then ease all the way off. You won’t always time it perfectly in the moment. But intentionally carving out a little space in your week is what lets you read whether this is a gas moment or a brake moment.
4
Accountability equals trust.
Early on, I wanted people to be happy with me, so I hesitated to hold the line. I believed direct conversations would cost me trust. The opposite is true. I learned that being clear and direct, and holding people accountable with respect and compassion, is how trust gets built.
5
W H A T M Y F I V E R E F L E C T I O N S H A V E I N C O M M O N
Every one of them is hindsight. I can see them now because I’ve finally had time to look back. Most leaders don’t look back until the pressure lifts, and the pressure never lifts on its own. The practice offered in the download on this page builds a small piece of intentional reflection into every week, while you can still change your course.