He Taught by Asking: A Reflection

My first and most significant boss and mentor, Stuart Kelman, passed away a couple of months ago. While we hadn’t been in close contact and saw each other only occasionally, his death was devastating for me. It was similar to how I felt when my father died. Stuart taught me an enormous amount about how to be a leader during the five years I worked for him.

Stu hired me to build a non-formal high school program for Jewish teenagers. We took groups of teens to nearby retreat centers for the weekend—four times over the course of a year. Over time this became an enormously successful program—adding different levels and a leadership development component. All that after a very rocky start.

We had conducted a pilot with 25 teens and that went brilliantly—so I went into our first full-on weekend, with over 100 teens, with a high level of confidence and a strong team of teachers. While I don’t remember exactly what went wrong that weekend, an awful lot did. The program didn’t land, kids were skipping activities, staying in their cliques, and not connecting across them. We had three more weekends ahead of us—and I wasn’t sure if we were going to be able to pull this off.

Around the Table

On Sunday afternoon, when we got back, I called Stu. He invited me over and we sat down in his dining room, at the big, wooden table that I got to know well over the years, and he handed me a scotch. He asked questions. With warmth, with care, and with intensity. He asked me about what happened, where I thought we had missed the mark, what I might do next—and more. He asked me to zoom in—and to zoom out. I felt deeply supported, deeply understood and equally challenged. My exhaustion transformed into energy and what had felt impossible, felt possible.

Back on Track

I left Stu’s house with a clear sense of what my next steps were. I knew I had to gather the team, treat our first “failure” as a powerful learning experience and, together, build a program that would address what we had learned. I rented a house on the coast and pulled together the whole team. We reimagined what a weekend could look and feel like and built out a massive Star Trek–themed simulation game about modern Jewish history. We worked our butts off and did some of the most creative design work any of us had ever done. The weekend arrived. The kids became part of teams representing diverse Jewish communities and ideologies and together addressed a Star Trek survival challenge, bringing their different perspectives to bear. It was a triumph. With that energy at our backs, we built out two more weekends that were each just as creative and engaging.

Teaching Me to Look

By asking questions, Stu helped me step back and look at what had happened differently. He offered no solutions and wasn’t concerned that I might arrive at completely different answers than he might have. Instead, Stu offered questions that enabled me to look differently—to see possibility where I saw a failure, to zoom out rather than get caught in the small details. Stu could have been more directive and gotten involved in the work, but that day and in our many, many meetings over the years, he continued to ask questions. And, over time, I learned to ask the questions myself. He trusted me because he trusted that I would ask the questions that needed to be asked. He had taught me to look differently and trusted the way I looked. I never felt that I had to see what he saw—Stu’s trust in me came because I had learned to look the way he looked. Not once in the five years that I worked for him did Stu step into the work itself. Given that I was twenty-five at the time, that now strikes me as amazing. I am certain that I am the leader and the coach that I am today as a result of the lessons I learned from him.

Many of us lead and delegate by trying to get people to do what we do — the steps, the method, the way we’d handle it. We might even lead by getting people to see what we see. That’s a step in the right direction. Asking questions and helping others look more deeply and systemically is a very different act of leadership. It’s helping someone learn to look at the context, the stakes, the why behind the how. It’s much easier to let go, to leave something in another person’s hands when you trust that they are looking the way you look. I realize it couldn’t have been easy for Stu to do what he did that day—or over the next five years. I came in with challenges that felt bigger than me and would have been happy to have gotten answers. Stu could have done just that and felt good about himself. He could have gotten the satisfaction that comes from providing answers, being a hero. He probably had to tolerate the discomfort of watching me struggle. I knew then and know with even more certainty now that his questions enabled me to look and to see differently—and ultimately led to me doing better work than I ever thought I could.

Staying with the Questions

Even now, many years later, I am not confident that I’m as good at staying with the questions as Stu was. I sometimes struggle to turn a question from a client to me into a question back to them—or to hold back an idea that my client hasn’t seen yet. Maybe Stu struggled too—and I didn’t know it. Maybe what seemed effortless was more work than it seemed. Thinking of that gives me even greater regard for Stuart and more confidence that we can learn what he taught. The question “What would Stuart do?” has lived with me since I worked with him years ago. And, when I ask it today, I experience it as a nod to a person who made such a big difference in my life.

Where are you offering answers, when you might ask questions? Where might you invite people to look with you rather than provide solutions?