Entrepreneurs Need to Lead and Be Led

“You talk as if you only like the sound of your own voice. Is it deliberate?”

I was stunned silent at the other end of the line.

My first six months as a manager and I was on a rapidly sinking ship, a non-profit voyage of the damned, with staff who loved everyone else and couldn’t find nary a redemptive glimmer in me.

I was locked in a cycle.

Read a new book. Go to a new training. Schedule another staff meeting.


I was doing everything I could. I was generous and giving.  Besides, they would grow to eventually like me. Because I, the girl with the books, could always could find a new strategy and a better way. But I couldn’t and they didn’t. Six months in and, for some reason, we were still missing each other.

Until I was told by someone much smarter than I was, that the reason I was searching for? It was me.

Six months and I had never asked the staff a question. I was just barking orders. Moving them like pieces on a chess board. “Go here!”, “Don’t do that!”, “It would be better if…” Not once did I ask them how to proceed.  Find out their motivation and create, with their expectations and strengths, a shared vision made real by the ongoing and mutual reshaping of each of us.

That staff on the other end of the line was the first person I ever asked about my leadership. This person gave it to me straight and taught me to reshape my management by going beyond myself. By asking difficult questions. Interrogating the process.

The ideological debate between managers versus entrepreneurs aside, both fall for overwhelmingly similar pressures and pitfalls.

How many of us are constantly riffling through seminars and strategies? Making our training and development about what “we” think we need to learn differently? Picking up the shiniest leadership tool in the box when we could just as soon talk to a person to find out if we are meeting people’s needs let alone our enterprise’s overall goals?

As belated and blessed teacher Rabbi Edwin Friedman alludes to in his seminal work, A Failure of Nerve, the details aren’t in the data. They are in the life of a unique emotional process that exists in every institution and community. As leaders, our task is to understand this process, which includes how people and systems interact and react. But ultimately, according to Friedman, our task is to master ourselves. 

That’s right: We can’t control our environments or even our staff people, but we can master ourselves.

At the start of my life as a manager, I’m struck that not only did I not know who my staff were but that I also did not know who I was.

I wanted to be liked but I barely knew which gifts I could offer up to the world, let alone my staff, gifts that were specially and sacredly mine to share.

In 2016,  I began my second-career and vocational journey as a Student Rabbi.  It is a journey of communal listening and learning, supporting individuals’ unique spiritual journeys toward the Jewish lives they imagine leading. And, as I support people’s becomings, as I watch them choose their own lives, I feel closer to my purpose than I ever thought possible.

The strong leaders I have learned from reflect this complexity: We have a duty to investigate and enhance our selves and we must move necessarily and deeply beyond them in order to foster lasting leadership.