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Finding the Ways That Work

“There’s a right way. There’s a wrong way. And there’s a way that works.”
-Dr. Avivah Sayres, passing along the wisdom of her supervisor, Dr. Hyman Spotnitz

Sometimes all it takes is a pack of cigarettes to resurrect the dead.

I was a young coach when a man I’ll call Bob reached out. Recently fired in his early sixties, he was frightened and trying to imagine another chapter in his life. Our coaching began, as it often did back then, with a few phone calls. No video calls then. With each call, I knew him a little better and liked him a little more. He struggled to find the money to pay for coaching and, wanting to help, I agreed to work with him at a reduced rate.

From the first, hearing why he wanted coaching, I knew something of his humiliation. My father had also lost his job late in life. Dad came home and told us there would be no Christmas that year. Then he cried. It was the first time I’d ever seen him cry. After the firing, my father was never the same.

And I learned a lesson I still hold today: you’re on your own, buddy. You can’t trust the company. (Which is why I like being an entrepreneur. I’m on my own, buddy.)

Bob arrived for our first meeting wearing a short-sleeved robin’s egg blue shirt with a pocket over the left breast. In that pocket was a pack of cigarettes. My father carried his cigarettes in exactly the same place. Suddenly, the man I had known over the phone became someone different: a man with kids, devastated by the loss of his job and terrified that he could no longer be the provider, the thing that defined him and so many men.

And suddenly I was ten all over again.

For the entire hour, I stared at that fucking pack of cigarettes. As Bob talked about losing his job and fearing for his future, I listened, or tried to, but I kept drifting back to my father. At 67, not much older than I am today, Dad died from complications of emphysema.

Sitting across from Bob, I felt the same emotions I had felt as a boy: fear, sadness, and an unsympathetic disappointment. In the years after he’d lost his job, I went from being afraid for our family to feeling bitterly disappointed in him. The anger I felt at Bob was anger that should have been, and had always been, directed at my father.

Afterward, I called my analyst, Dr. Avivah Sayres. I told her what had happened and that I couldn’t work with Bob. She cut me off, insisting that I stay right there, right in that seat. Bob had brought something forth in me, something deep and unresolved, and it was my responsibility to Bob as well as to myself to work with it. Sending Bob away would leave the feelings untouched and me vulnerable to repeating the same pattern with someone else. I would not grow as a coach if I steered myself away from the difficult feelings a client brought up in me.

While she didn’t call it that at the time, that conversation was supervision. And it is one of the many such conversations that made me the coach I am today.

Supervision is a protected conversation in which a coach brings the experience of working with a client to another trained practitioner. The client’s predicament is part of the inquiry. But, importantly, so are the coach’s reactions. The supervisor helps the coach ask: What’s happening here? What part of this is mine? (Or, as a therapist friend of mine would say in our twice-monthly analytic group after a particularly challenging client session, “What was that?”)

I continued working with Bob, and I kept bringing what he stirred in me to Dr. Sayres. Over time, the pack of cigarettes became just a pack of cigarettes, and the light-blue shirt became just a shirt. The scared, struggling man became someone I could happily help. He did find another job. His story ended well.

He was not, and never had been, my father. My father was no longer sitting in the client’s chair, and the dead returned to wherever it is they go.

In this month’s episode of the Reboot Podcast, I speak with my colleague Liz Stewart, who leads supervision at Reboot. Liz describes the moment a coach knows there’s something to bring to supervision: “Something came home with me.”

The coaching session has ended, she explains, yet part of it lingers. The coach is unusually tired, still rehearsing an argument, or thinking about the client at dinner. In supervision, Liz listens both to the story and to the person telling it. She notices where the coach speeds up, when they move past something troubling, and what arises in her as she listens. Then she slows the conversation down. One of the questions she’ll ask is, “Do you have any experience with this feeling?”

The coach can no longer hide inside a case report.

Training gave me frameworks, techniques, and a code of conduct, all of which I needed. But it didn’t prepare me for the psychological impact of the work. In my early years, I sometimes needed an hour of meditation, and occasionally an hour of smudging, after an hour of coaching. Something had been stirred up, but I didn’t always know what it was or where it belonged. “What was that?” indeed.

That’s why supervision is at least as important as training. Certification establishes a minimum standard of competence, but it doesn’t anticipate the client whose despair follows you home, the founder whose wealth awakens envy, or the person whose story returns you to your childhood. Those encounters become part of the curriculum only when the coach has somewhere to take them.

There’s also an ethical responsibility behind supervision. If I don’t examine what a client awakens in me, I risk using the session to work out my own unfinished business. Fear becomes advice and envy becomes judgment. The need to be loved makes me hold back from challenging a client, the very thing they come to me for.

Good intentions offer little protection from unconscious motives, even among coaches.

Coaches are asked to enter the most consequential moments in people’s lives. We sit with marriages coming apart, companies running out of cash, children in trouble, and the vertigo of sudden wealth. A conversation begins with a board meeting and ends with the father whose approval the client is still trying to win. To enter these conversations is to be entrusted with more than a performance problem. Both care and harm are possible.

I’ve been coaching for nearly three decades, and I still bring my clients into my own analytic work. Experience hasn’t lessened the need for supervision. The more certain I seem to be, the more useful it is to have someone who can call me out. I tell my therapist and my Reboot colleagues the same thing: “Don’t let me believe my own bullshit.”

In this conversation, Liz and I explore the feelings coaches carry home, the difference between supervision and mentoring, and the responsibility to examine the person who enters every coaching session with us: ourselves. Whether you’re working with a coach or thinking of heeding the vocational call of coaching, it’s a worthy conversation. Enjoy it.

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AI Can Ask the Questions But It Cannot Feel the Room Coaching supervision is its own discipline. It’s a dedicated space where coaches come to examine their relationship with their work — with their clients, with the teams they serve, and with the parts of themselves that enter the room, whether they mean them to or not.
When Coaching Stops Working: The Hidden Doorway of Supervision One of the most overlooked aspects of coaching is how we, as coaches, bring ourselves into the work. The stuck moments, the unexpected discomfort, the dynamics that subtly unsettle us—these aren’t just client issues. They are invitations to turn toward what’s happening in us. To ask, What is this moment asking of me?
Personal and Professional Depth To be a more effective coach is to know yourself and what you bring to situations, as well as how to be in service to what is larger than you and what is unsaid and emergent in any space, be it 1-1 or in facilitation.

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