The Subordinate as Coach

February 18, 2026

By Dave Bushy, PCC

How can I coach my boss?  A client asked me this question the other day.

My response was open-ended:  “How do you coach anyone?”

After a few humorous asides from my client, including “Why do you always answer a question with another question?” we dug into the genesis of the query and how my client felt she could approach it.

“Let’s start off with what you know about your boss,” I said, setting the stage for our session.

“Well, he’s bright and he cares a lot, but I suspect he doesn’t fully understand my role.  Maybe he never served in a position like mine. Sometimes it seems as if we click and sometimes not.”

“Tell me more,” I smiled and received a thoughtful look back.

“Well, I’m not sure his experience gives him perspective.  He has wonderful aspirations that don’t seem as realistic as they might be.  He wants everyone to like each other, to trust each other and to work well as a team.  But that doesn’t work out in reality.”

“What happens when you ask him about how he sees things playing out on his team?

“Well, he gets defensive and then I get defensive back.  Actually, I go on the offensive, trying to convince him that he is wrong and I am right.”

“Sounds as if you trust each other enough to argue.”

“Mostly, but it ends up going nowhere and we usually just move onto another topic.  But boy, does it simmer inside of me.”

“And what happens with that simmering?”

“It becomes a sort of unseen presence in our conversations.  I try to avoid the feeling it gives me, but it definitely grates on me and I can feel it eroding our relationship.”

We spent some time talking about how my client carried those thoughts and what she felt her options were.   Speaking at length, she continued to emphasize the desire for him to understand her and the need to press forward with her arguments. 

I continued our conversation with the curiosity of a coach.  Inquiry has always been my tool and I stayed curious throughout.  My questions, it seemed, continued to help the client explore the relationship, and what was happening each time she spoke with her boss.

My questions were my tool and something interesting happened with the use of that tool.  At one point in our conversation, my client said, “You ask a lot of questions and then you listen.  Why don’t you ever try to convince me of something?”

I laughed and responded, “And what would that do?”

She laughed at length with me and then said, “I guess I’d argue back.”  And then I noticed a distinct shift in my client, as a she paused at length and then looked intently at me and said, “I wonder if I just asked my boss questions like you do?  Open-ended questions, without any pushback or argument back.”  She sat quietly for a long time, in deep reflection, as I stayed silent and gave her time and space.

She added, “I’ve proven to myself that I can’t convince him by arguing, but I can stay curious about what he is thinking and why.  I can ask questions and then ask more.  Perhaps that will be a catalyst for exploration of how we work together – and maybe that’s enough for now.”

“And how will you do this?” I responded.

She smiled and then responded with a simple question, “What happens if we just find out?” and then laughed out loud.

Dave Bushy of Boston Executive Coaches – bostonexecutivecoaches.com – is a an ICF-certified coach who was trained at the Gestalt International Study Center (GISC).  Dave is a former U.S. Army officer and senior airline executive who works with leaders throughout the world.

Image by Peggy und Marco Lachmann-Anke from Pixabay

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