Conversations I used to avoid

Author: Kathy Callahan

In my early days as a supervisor, I used to dread sharing difficult feedback.

Maybe I was avoiding conflict. Maybe I wanted everyone I worked with to like me. Maybe I was worried I wouldn’t say it well or wouldn’t know what to do if it went badly.

What I do know is that I avoided those conversations, or delayed them. And when you do that, they don’t get easier. They get heavier.

Later in my career as a supervisor, and as a supervisor-of-supervisors, I was much more comfortable with these conversations. They triggered no anxiety in me. I prepared, and stepped into them confident, and comfortable in my own skin. Clarity.

What changed?

A few experiences over time started to shift this for me.

The first was many years ago. I remember anxiously preparing for a feedback conversation, imagining all the ways it could go badly. I stepped into the room, nervous and slightly sick to my stomach.

And then… something unexpected happened.

He listened. Really listened. Took notes. Made changes. The turnaround was significant, and he went on to stay with the organization for many years, growing into more senior roles.

That experience helped me trust that people can respond to clear feedback in ways you don’t always expect, and that the results could be positive.

The second experience was much harder. The team had been struggling because of the consistent underperformance of one teammate for months—some would say years. But we loved her; she was one of us. Despite numerous feedback conversations, nothing improved. Working with HR, we eventually had to let her go.

What happened next changed me as a supervisor. The team’s performance and overall wellbeing improved. Work/life balance was restored, as they were no longer compensating for this gap.

My delay, my discomfort in addressing the situation directly, hadn’t just affected that one person. It had been affecting everyone.

It wasn’t a lesson I enjoyed learning, but it was a necessary one.

But the third situation, that was the paradigm shift.

For years, we had been building our work at EnCompass using Appreciative Inquiry, not just with clients, but in how we ran the organization. And I started to ask myself: why wasn’t I applying that same approach to supervision? What would these conversations look like if I did?

That question shifted something.

An appreciative supervisor starts with co-creating a vision of success. Together, you hold a clear picture of what strong performance, collaboration, and teamwork look like. And then the conversation becomes about alignment with that vision.

We celebrate when we are aligned with that vision, in appreciative feedback conversations. We talk about when we are out of alignment with that vision, in constructive feedback conversations, using generative questions.

For me, that brought a kind of clarity I hadn’t had before. And with that clarity came a lot more ease. Not because the conversations are always easy, but because I’m no longer avoiding them or overloading them.

I have them more often. And I have them with a clearer, more appreciative frame…using Appreciative Supervision.