I Went for a Haircut. Got Into a Leadership Conversation

I wasn’t planning to talk about management last Tuesday.

I was planning to get a fade, maybe catch whatever was playing on the TV in the corner, and be home inside an hour. But that’s the thing about nineteen years in this work — it just comes out, whether you planned it or not.

I’ve been going to Players Studio in Oakville for about a year now. Raf runs the place. He’s a young entrepreneur — sharp, hard-working, the kind of guy who’s clearly building something with intention. We’ve built a rapport the way you do with a good barber: slowly, over a lot of small conversations, until one day you realize you actually know each other.

That day, something was different. He wasn’t his usual self.

It didn’t come out as a formal complaint or a question. It just surfaced the way real things do — mid-conversation, between talk about other stuff. He had an employee who wasn’t performing. Not in one way. In several. Attitude. Output. Reliability. Communication. All of it, at once, from the same person.

“Is it always like this?” he asked. Not really to me. More to the room.

I should have stayed in my lane. I was there for a haircut.

But I’ve spent the better part of two decades managing teams — in SaaS, in fintech, across global support organizations with people on multiple continents. I’ve seen this exact situation more times than I can count. And I knew what I was looking at before he finished the sentence.

So I told him what I knew.

We ended up talking for the better part of the appointment. He went from venting to asking questions. By the end, he was taking mental notes. He even sent a voice message to his girlfriend — who works in banking, completely different world — and she came back saying it applied directly to what she was dealing with too.

That’s the thing about good management. It doesn’t care what industry you’re in. The fundamentals work the same whether you’re running a barber shop in Oakville or a department in a bank downtown. The principles don’t change with the industry. They just change with the person’s willingness to apply them.

Over the next four posts, I’m going to walk through exactly what I told him. Three foundational principles that most first-time managers either don’t know or know but never actually implement. And then the two conversations that sit underneath all of it — the one you should be having from the start, and the one you keep putting off.

None of this is complicated. That’s actually the point.

Next up: the reason your employee seems busy but nothing gets done — and why your calendar is the place to start.