People often ask me what actually happens in a coaching session. It's a fair question. Coaching can sound abstract from the outside, and if you've never worked with a coach, it's hard to picture what our time together would feel like or what you'd walk away with.
So rather than describe it in general terms, I want to walk you through one session. Dana (name and details changed to protect client confidentiality) gave me permission to share it.
The Question She Brought
Dana is a leader who had already made a difficult decision: an employee on her team needed to be let go. The plan was in place. But as the time came closer, she found herself second-guessing it and wondering whether she should delay. She had been turning it over again and again without getting anywhere, and underneath it all was a real fear of being seen as the bad guy by someone she genuinely cared about.
Starting With What She Wanted to Leave With
Every session starts with some version of the same question: what do you want to come away with today? Dana said she wanted a path forward she could feel comfortable with, and secure in, as the best possible choice. That became our anchor. It didn't mean we followed a script. It meant we had something to return to, and near the end we did, to see whether she had found what she came for.
Making Room for All of It
A decision like this is never only logistical. Alongside the practical questions about timing and HR, there was grief, moral weight, and worry about damaging a relationship. Part of my role is to make it safe to bring all of that into the room, so Dana didn't have to tidy up her feelings first or manage mine. When people don't have to perform being okay, they can think more clearly.
Listening Underneath the Question
On the surface, the question was "now or later?" But as Dana talked, other words kept surfacing: humanity, integrity, authenticity, not wanting to cause harm. I reflected those back to her, in her own words. Hearing them out loud changed the question. It was no longer only about when to act. It became: how do I act in a way that's true to the leader I want to be?
Noticing What Shifts
As the question changed, something in Dana began to change too. When she considered moving forward with the original plan, carried out with care, she noticed a feeling of relief. We paused there so she could actually feel it rather than rush past it. That kind of physical signal often tells us something our thinking hasn't caught up to yet.
Arriving at Clarity
By this point, Dana could see something that wasn't visible at the start. Moving forward with the plan didn't have to mean abandoning her values. She could carry it out with empathy and honesty. And delaying, which had seemed like the kinder choice, would actually have felt less authentic, and potentially more damaging, over time. The decision was hers. She arrived at it herself, and she could say why it felt right.
From Insight to Next Steps
Clarity matters, but it isn't the finish line. Before we closed, Dana named her concrete next steps: her conversations with HR, how she wanted to approach the conversation with her employee, and, just as importantly, how she would take care of herself around a hard day. We ended by returning to where we started. Did she have a path forward she felt secure in? She did.
What a Coaching Session Is (and Isn't)
I didn't tell Dana what to do. I didn't hand her a framework or a list of pros and cons. Coaching is grounded in the belief that people have their own inherent wisdom, and my role is to help clear the way so they can reach it. Sometimes that includes tools like tapping or meditation. In this session, it was conversation, careful listening, and attention to what her body was telling her.
Every session is different, but the shape is often similar: name what matters, explore it honestly, and leave with something real to act on.
An Outside View
This session was later reviewed by Optify, a leadership coaching provider that assesses coaches against the International Coaching Federation’s Core Competencies before selecting them for its coaching bench. One line from that review captures what I hope every client experiences:
“What stands out most is Jill’s ability to help the client move from moral distress and internal looping toward values-based clarity.”
-Friderike Butler, Coach Recruiter, Optify
Curious What This Could Look Like for You?
If you're carrying a decision that feels heavier than it should, or you're simply curious what coaching could offer you right now, a free 30-minute discovery call is a good place to start:
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