it was a profound experience—an experience of myself. Not who I wanted to be. Not who I thought I should be. Nobody special. Just me—bones and flesh, thoughts and emotions coming and going. It was beautiful. Better than any drug—and I’d tried more than one. In that moment I made a decision, as much as you can decide anything long-term when you’re 28, unemployed, and single. I was going to ride that self-discovery train as far as it would take me.
I spent the better part of the next decade doing just that. I had jobs and ventures to pay the bills. But my heart was in the search. I went on more and longer retreats. I travelled to high mountains in faraway places to look for wise teachers. I moved to San Francisco, which, to a Jewish kid from the New York suburbs, was the mecca for all things weird and leading edge. I helped to start a renewable energy business. I dove headlong into the world of alternative healing: studied to be a yoga teacher, trained in somatic psychotherapy, and considered going back to school to get a master’s in psychology. I joined up with some friends to create a nonprofit that teaches meditation and mindfulness to kids in juvenile hall. I fell in love and had the first real long-term relationship of my life.
Along the way I found a few things that I was genuinely good at and could have made a career of. But I still couldn’t shake that feeling. The one that was sure that whatever I was supposed to be doing with my life, I hadn’t found it yet. It turns out, I didn’t need to. It was about to find me.
In 2011 I came across an opportunity that I couldn’t resist. I took on the CEO role at EMyth, the business coaching company behind the well-known book. The owner had decided to relocate the company to Ashland, Oregon, the small town halfway between Portland and San Francisco where I was living. Finding myself at the helm of a name-brand coaching company, with a mandate to revitalize the culture and take things in a new direction, was the kind of big city opportunity that I never imagined I’d find in a town known primarily for its annual Shakespeare Festival.
The first few years were a thrilling and wild ride. I was still pursuing my own personal work on the side, but the leadership journey I was on was too exciting to leave room for much else. I had a platform to express myself out in the world, the kind I’d always dreamed of. Along with my co-managers and our small but dedicated team, we took the company through a full-blown transformation: from culture and brand to technology and process, and everything in between. The team was inspired. The brand came back to life. People whose books I’d read said they loved my writing and the new message. Consultants who’d been around the corporate-transformation block praised the changes we’d made.
But there was a mismatch. It was there from the start, but I didn’t notice it from the uniquely weird viewpoint that comes with the CEO title. I was managing the business in the only way I knew, fast and full of risk. But being in a small town created some very real limits. The pace and kinds of risks I wanted to take were out of step with the stability and lifestyle most people move to a small town to have. People were genuinely inspired by what we were doing, but I was leading a different company in my head than the one that was there on the ground.
Isn’t it incredible how life brings you the voice you need to hear in the moment you need to hear it? I was in mid-realization of that mismatch when I went to a conference and heard two well-known corporate visionaries—Gary Hirshberg of Stonyfield Farm and Curt Richardson of OtterBox—share their stories of stepping out of the CEO role to make room for the leader the business needed next. My next step was as excruciating as it was clear: It was time for me to let go of what felt like my baby and make room for someone else. Second to meeting my wife, stepping out of the CEO role and into a supporting one was the best thing that ever happened to me.
Over the next two years I had two unique new experiences that few leaders ever have the “good fortune” to get. The first was that I got a taste of my own medicine. I saw what it was like to live and work in the culture that I’d created: The unrealistic pace of projects, how my appetite for risk was not shared by everyone on the team, how what looked like a clear initiative in a leadership meeting could still be incredibly confusing to the team trying to implement it. In my new business, this is one of the things we work actively with CEOs to see: how one idea from the top can spiral into 100 projects for the team and overwhelm them in ways the CEOs can’t even imagine.
But the second experience was the one that really hit me. It was that, as the CEO, I was radically overestimating the quality of mentoring that most managers—myself included—were doing with the people on their team. It’s a phenomenon I see repeating itself every day in the work I do now with managers at every level in different organizations around the world. What managers are doing, including some of the smartest and most caring people I’ve ever met, has almost no real mentoring to it. And even the mentoring they’re trying to do to get people to take personal responsibility is undermined by the background company culture dynamics that send a very different message: Keep your head down, do your job, and don’t rock the boat.
It’s incredibly easy for the CEO to miss. Under the enormous pressure of the role, their vision gets tighter. It becomes finely tuned to fluctuations in numbers and goals, and less sensitive to the interpersonal and interdepartmental dynamics. Employees start to feel less important even though you, as the CEO, know they’re not. And because you’re the person who holds everyone else’s paycheck in your hands, you almost never get honest feedback about how people are feeling. That is, until they’re frustrated enough to quit or they act out enough to get fired.
When it comes to employee development, what managers do—what I was doing—was almost exclusively the easy stuff: encouraging words, good advice, and, more than anything, jumping in to fix short-term problems to keep projects moving along. But what my team needed was something else entirely. They needed me to listen. They needed me to hear what they were saying and do something about it. They needed me to hear what they weren’t saying and use that insight to create more definition to their role so that there was even a job for them to own. And they needed me to set clear boundaries and make sure everyone was held accountable to the same standard. They were not lazy. They were not incompetent. And they were not uncaring. They were waiting.
I made a decision. Since I’d tried everything else, I was going to try something new, something that I’d written a lot of blog posts and delivered a lot of webinars and workshops about but had never really done. Not with all my heart. I was going to let my team tell me what they needed from me instead of me telling them what I needed from them. I was going to help them grow personally and trust that the professional side would take care of itself. I was going to do everything in my power—which was still quite a lot—to improve the experience of working there. I decided to do whatever I could to create a great place to work, one conversation at a time.
I started talking with each person on my team in a new way. I asked them far more personal questions than I’d dared to do before—not about their personal lives, but about their personal relationship to their work. I did a lot less assuming that I knew, or was supposed to know, the answers. I took the risk to let my guard down and shared more of how I struggled with some of the very same issues they did. They responded. They took ownership of their work in ways I always wanted them to but never knew how to bring out of them. And what was most rewarding for me was that the changes they were making translated into other parts of their lives. Sometimes I would hear about it directly, other times I could tell by how they talked about their lives in the water-cooler moments of the day. A few of those conversations when I got to hear it directly were what gave me the confidence to keep going.
I was in my office wrapping up a few things before heading home one afternoon. One of the guys on my team, who’d been working for me for about a year, stopped by on his way out the door. He was smart, capable, and was doing fine work. Still, as I’d come to know him over time, I had a sense that he had a whole other gear. For some reason, he was holding himself back. I’d made it my mission to find out why, and to see if I could help him take the next step in his own growth. We talked about the theme every week in our individual meetings. I gave
