Whose Chair Am I Sitting In?
Whose chair am I sitting in? It is a strange question to ask in a conference room, but it is the one that two and a half days of training kept putting in front of us.
I spent this week at the Fall Institute of the Wexner Field Fellowship, learning about difficult conversations from Toby Berkman and Aarati Halbe of the Consensus Building Institute, whose work draws on Difficult Conversations: How to Discuss What Matters Most by Bruce Patton, Douglas Stone, and Sheila Heen, a book I have read and reread that came to life this week. As a Head of School, I have my share of these conversations: with parents, students, staff, board, and sometimes donors. As a Jewish communal professional, I have them with people I will see at kiddush on Shabbat, at the JCC, and even when walking in my neighborhood.
One of the more impactful sessions came from the exercise with three chairs. What each of us shared in the room stays in the room, so I will share the method and keep the stories confidential. One person, the presenter, brings a real, difficult conversation. A partner, the helper, interviews the presenter about it. Then the presenter changes seats, literally, and becomes the other person in the conversation, the absent party, speaking in the first person while the helper asks questions. Two people, three roles, three chairs. The ground rule was a phrase I have not stopped repeating: geography is destiny. Where you are sitting is your reality.
Here is what that move makes possible. From the absent party’s chair, you can sometimes discover that the difficult conversation you came to rehearse is actually the wrong conversation to be having. It also sent me home asking what kind of chair I offer to the people who have to meet with me. And what type of chair am I sitting in?
Hillel taught, “Do not judge your fellow until you have reached his place” (Pirkei Avot 2:4). The Hebrew is al tadin et chavercha ad shetagia limkomo, “until you reach his place.” For me, “place” had always been a metaphor. Hillel did not have a helper to interview him (unless you want to consider Shammai as his helper), but he understood what the training took two and a half days to build: you cannot speak well to someone you have only seen from your own seat.
At the end of the institute, we moved from sitting in a chair to building one. I adapted the 5 Chairs design thinking exercise from the Stanford d.school K12 Lab and Digital Promise for this group, with some help from Claude (Claude could draft an agenda; it could not sit in the chair). My plan was to have fellows design chairs for assigned profiles. At the last minute, I changed it. Instead, each fellow drew three chairs for the actual person from their own difficult conversation. In groups of three, we shared our drawings, and each table chose one design to rebuild in four more materials: cardboard, pipe cleaners, clay, and finally tape and toothpicks. The materials are humble on purpose, and nobody was graded on craftsmanship (good news for those of us whose last pipe cleaner was at summer camp, and kudos to the camp directors who felt right at home). Twice, in the cardboard and clay rounds, we handed out disrupter cards, new facts that the chair had to survive.
A chair designed for everybody fits nobody. A chair designed for one real person, drawn three ways and rebuilt in four materials, asks a different question from “what do I want to say?” It asks, “What does this person need in order to sit here?” It was fascinating to watch Jewish communal leaders work together, to see who took charge, who had a unique take, and who just wanted to play with the Play-Doh. But it gave us a chance to sit in the uncomfortable, to think about what chair we provide to others.
In the debrief, someone asked whether we knew the CBI faculty would use three chairs in their exercise. We had not. I am not one to see a sign in every coincidence (though in my line of work, a coincidence with a Jewish text attached gets a second look). What I will say is that two groups of people, working separately, reached for the same object to teach the same thing: that a conversation changes when you stop defending your seat and start asking about someone else’s.
In a single week I am an educator, a supervisor, a colleague, a neighbor, a spouse, a parent, and a Jewish communal professional, and the people across from me are often several of those at once. When Rabbi Stacy Rigler and I opened our cohort’s institute with DISC, we were asking the same question from a different angle. DISC is a simple self-assessment that sorts our default style into four types: Drive, Influence, Support, and Contemplation (D, I, S, and C; the letters get different names in different versions of the model, and the labels matter less than the idea). You choose the words that sound most like you, tally the columns, and see which one you reach for first. The point we kept repeating is that no style is the best one, and every group needs all four (the room that is all D is fast and wrong; the room that is all C is careful and still meeting). My results came out highest in the D column (dominant, determined, decisive; I will let my colleagues supply the other adjectives), and I wrote a reminder at the bottom of my worksheet: other people are not a failed version of you.
What I am taking home is small and practical. I will sit in their chair before I speak (even if only in my imagination, and even if the helper is a very patient colleague), and when my inner voice gets loud, I will name it to tame it. I will build for the person who will actually sit in it (not the average one, who has never once come to a meeting). And I will lean into the uncomfortable pause and stay in the conversation long enough to reach the finish line (a pause is allowed; leaving the room is not). The handwritten sign I made a few years ago hangs by my desk and says it plainly: “Relax. Listen longer. It’s OK to amend. Lots of small changes make a big change. And be your own anthropologist.”
Our schools, synagogues, federations, and camps are, among other things, rooms full of chairs. Ben Zoma asked, “Who is wise?” and answered, “One who learns from every person” (Pirkei Avot 4:1). I would only add that it helps to learn from where they are sitting.

