About this series: This is the final post in the Barbershop Leadership Series — five management posts that came out of a conversation I had at Players Studio, a barbershop in Oakville run by a young entrepreneur named Raf. He was quietly struggling with a difficult employee situation when I showed up for a haircut, and we ended up spending most of the appointment talking through how to handle it. The conversation covered time blocking, structured note-taking, setting clear expectations, and now — the conversation that holds all of it together. Each post stands alone, but if you want the full series, it starts here.
Something happened partway through the conversation with Raf that I’ve thought about a lot since.
He pulled out his phone and sent a voice message to his girlfriend. Right there, mid-cut. She works at a bank — completely different industry, different environment, different scale — and he just wanted to share what we’d been talking about. She listened and came back immediately. She loved it. She said it applied directly to situations she was dealing with right now.
That’s the thing about good management. It doesn’t care what industry you’re in. The principles we’d covered — time blocking to create space for leadership, structured note-taking that shifts accountability, setting expectations before you need to enforce them — none of them are barbershop ideas. They’re just management. And good management is the same whether you’re running a shop on Lakeshore or a department in a bank tower downtown. The fundamentals don’t change with the industry. They change with the person’s willingness to apply them.
Which brings me to the hardest one.
After we’d talked through everything else, Raf came back to the original problem. The employee. The one who was late, inconsistent, dismissive, checked out.
“So what do I actually do?” he asked. “Like, how do I have that conversation?”
It’s the right question. And it’s the one most people never ask — not because they don’t want to know the answer, but because asking it means committing to actually doing it.
Let me be direct about something first: avoidance is not a neutral strategy. Every day you delay a performance conversation, the situation worsens in ways that are easy to miss until they’re not. The employee’s behaviour continues unchecked. Your frustration builds quietly. Other team members notice the gap between what’s expected of them and what’s being tolerated from someone else. Standards drift. Trust erodes. Research consistently shows that only about 31% of leaders feel genuinely comfortable having difficult conversations — which means the majority are managing the discomfort by doing nothing. And that inaction has a compounding cost.
A Gallup analysis found that 42% of employee turnover is preventable — and that nearly half of employees who left voluntarily had no meaningful conversation with their manager about job satisfaction in the three months before they resigned. The conversation that wasn’t had is often the reason people leave. Sometimes it’s because the manager never addressed the problem, and the employee eventually found somewhere else to go. Sometimes it’s because the frustration came out sideways in a moment of heat that damaged the relationship beyond repair. Either way, the cost falls on the business.
Instinct-driven leaders — and Raf is one, which is not a flaw, it’s just where he is right now — tend to handle performance conversations one of two ways. They either avoid them for as long as possible, hoping things will self-correct, or they let the frustration build until it comes out sideways in a moment that doesn’t land the way it needed to.
Neither works. And both have a cost.
Here’s the cost of avoidance that most people don’t think about: the employee doesn’t know there’s a problem. I mean that literally. In many cases, the person you’ve been quietly frustrated with for weeks has no idea anything is wrong. They’re going about their job with their own interpretation of how it’s going. They might even think things are fine. They haven’t been told otherwise. So they’re not trying to fix anything, because as far as they know, nothing is broken.
Every day you delay is another day that gap widens. Another day the standard isn’t being met. Another day you absorb the cost in stress, in lost productivity, in the quiet resentment that builds up on both sides when expectations are misaligned and nobody says anything.
The conversation is uncomfortable. But it is never as expensive as the silence.
So how do you actually do it? Here’s the framework I shared with Raf — simple enough to remember, structured enough to keep the emotion out of it.
Talk about what you observed, not what you feel. The moment you say “you have a bad attitude” or “you don’t seem to care,” you’ve made it personal and the employee’s only real option is to defend themselves. Nothing gets resolved. Instead: “I’ve noticed you’ve arrived after your start time three times in the last two weeks.” That’s a fact. It’s observable. It’s not a character assassination. The employee can’t argue with what happened — they can only explain it or own it.
Be specific about what you need. Don’t end the observation without the expectation. “I need you to be here and ready at your start time, every shift.” Pair the observation with the standard. This is where all the work from the expectations conversation in Part 4 pays off — if you’ve already set the standard, you’re just referencing it. You’re not inventing a new rule in the middle of a performance conversation. You’re holding the line on something you both agreed to.
Ask what’s getting in the way. This is the part most managers skip, because it feels like it softens the message or gives the employee an out. It doesn’t. It’s just good leadership. “Is there something going on that’s making it hard to hit these expectations?” Sometimes the answer is personal — something outside of work that’s affecting performance. Sometimes it’s a process issue on your end that you didn’t know about. Sometimes they’ll say nothing, and that tells you something too. But asking creates space for a real conversation instead of a one-sided lecture. And it’s the difference between managing someone and actually leading them.
Set a clear next step — and a timeline. Vague performance conversations produce vague outcomes. “Let’s see how things go” is not a plan. At the end of the conversation, you need to land on something specific: what the employee will do differently, by when, and how you’ll both know if it’s working. “Over the next two weeks, I need you to hit your start time every shift. We’ll check in next Thursday to see where things stand.” That’s a plan. It gives the employee something concrete to work toward and gives you a clear point at which to assess progress.
Document it. Once the conversation happens, it needs to exist somewhere outside of your memory. A quick email after the fact: “Following up on our conversation today — here’s what we discussed, here’s what we agreed to.” This isn’t about building a paper trail to fire someone. It’s about creating shared accountability. The employee wrote the meeting notes in every other conversation — here, you write the follow-up. Because this one matters most.
Raf was quiet for a moment after I walked through this. Then he said something that I’ve heard in different versions from a lot of new managers over the years.
“I don’t think I can do that. It feels too formal. We’re a small team. It changes the vibe.”
I get why it feels that way. When your team is small and the relationships are close, structure can feel like you’re adding unnecessary distance. Like you’re becoming someone different from the guy who built this thing from scratch.
But I asked him to think about it differently. The structure isn’t the opposite of the relationship — it protects it. Right now, his relationship with this employee is being eroded by a slow accumulation of unaddressed problems. The vibe is already off. The tension is already there. He’s already frustrated, and the employee probably senses it without understanding why.
The conversation — structured, calm, based on observable facts and clear expectations — is the thing that actually resets the relationship. It gets the problem out into the open, where it can be dealt with. That’s not formal. That’s just honest.
I’d also push back on the idea that having these conversations changes who you are as a leader. Research on psychological safety in teams makes the point clearly: psychological safety is not the absence of tension or accountability — it’s the presence of honesty. A team where problems are addressed directly and fairly is a team where people feel safe to raise concerns, take risks, and tell you when something isn’t working. The avoidance of difficult conversations doesn’t preserve psychological safety. It destroys it.
By the end of our conversation, Raf got it. Not just intellectually — I could see it land. The investment up front in structure, in documentation, in a real conversation, is less expensive than the alternative. It always is.
This is true whether you manage one person or a hundred. I’ve written about this in the context of larger support organizations — the dynamics are different at scale, but the root principle never changes. You cannot lead people you won’t talk to honestly. And honesty, delivered with structure and care, is one of the most respectful things you can offer someone who works for you.
We’ve covered a lot of ground in this series. Time blocking to build space for leadership. Structured note-taking that shifts accountability to the employee. Consistent one-on-ones that catch problems before they become crises. Setting expectations clearly and early. And finally — having the direct, honest conversation when someone isn’t meeting the bar.
None of this is revolutionary. I want to be clear about that. I didn’t invent these ideas in a barber’s chair in Oakville. These are the fundamentals that work, applied consistently, over time. The reason they’re rare isn’t because they’re hard to understand. It’s because they require intention. They require you to build the time, do the work, and have the conversation — especially when your instinct is to stay in motion and deal with it later.
Raf is a genuinely hard-working guy who cares about what he’s building. He has the right instincts for the craft and the right values for the culture he wants to create. What he needed — what most first-time managers need — is a framework to match the intention.
I hope this series gave him some of that. And if you’ve been reading along and some of this sounded familiar — if you recognized yourself in a few of these situations — I hope it gave you something too.
The barber shop is always open.
← Part 4: Four Problems. One Root Cause.
← Read the full series from Part 1
Hutch Morzaria is a Director-level CX and Support Leadership professional with 19 years of experience building global support organizations across SaaS, Fintech, and enterprise technology. He has hired dozens of support and CX leaders across his career and holds ITIL Expert certification across V3 and V4.
