When Your Employee Is Also Your Mate
He was a mate first
He hired his mate. Of course he did. Someone he trusted, someone he wanted to see do well.
Then life started going sideways for his mate. His marriage ended. Money got tight. One rough year rolled into the next.
So, he did what good people do. He covered. He let the late starts slide. He picked up the slack himself. He told himself "he's going through a lot. He'll come good."
That went on for years.
By the time he called, it wasn't just a work problem
When he finally rang me, it wasn't about a few late starts anymore. The business was at risk.
Every conversation he hadn't had was now ten times harder. Every option on the table was going to cost something.
We got him through it with a fair outcome, and the business survived. The friendship didn't.
Why good bosses wait too long
I ran into him recently. I'd honestly forgotten the details, but he hadn't. He was grateful. He was also still sad.
I get why he waited. Most people in his shoes do. They wait because:
Loyalty. You don't kick a mate when he's down.
It feels personal, not professional. "It's not really a work thing, it's just life."
Awkwardness. "How do I raise this without wrecking what we've got?"
Nobody to ask. Small businesses don't have an HR department down the hall.
Waiting feels kind. It usually isn't, for either of you. The longer it runs, the fewer good options are left.
What reaching out earlier actually looks like
Here's what I'd have told him in year one. None of it is complicated, and all of it is easier early.
Have the conversation, even if it's informal. A coffee is fine. "You haven't been yourself lately. What's going on, and how can I help?" Afterwards, write it down: the date, what you talked about, and what you agreed. This isn't about building a case against your mate. It's so you both remember the same conversation if things don't improve.
Offer real support. What's right depends on what's going on for them:
Time off. Annual leave or unpaid leave. And if it's taking a toll on their health, personal leave too. Depending on your policies, you may have more flexibility than you realise, especially for the odd day here and there.
An Employee Assistance Program (EAP), if you have one. It gives them free, confidential counselling, often with someone they'll never have to see at the pub.
A different way of working. That might even mean going casual, if it genuinely suits their life right now. It has to be 100% their choice, never something you push.
Know where the line is. Support and flexibility go a long way. But the moment it starts affecting how the business runs, it's a performance conversation. That means jobs running late, customers noticing, or the rest of the team carrying the load. Having that conversation doesn't mean you stop being kind. It means you're clear about what the job needs.
Try it yourself first, then bring someone in. Informal chats work best between the two of you. Once things get more formal, have someone else sit in, either a senior person in your business or me. Let your mate bring a support person too. It takes pressure off the friendship and keeps things fair for both of you.
Don't expect it sorted in one chat. This usually takes a few conversations over weeks or months. Some things will improve and some won't. That's normal. What matters is that you started while there were still good options on the table.
You don't have to choose between kind and fair
Calling someone early isn't a plan to get rid of your mate. It's how you keep backing him without betting the business on it.
Most of the owners I help wish they'd called sooner, and he certainly did. If you've got a mate on the payroll and a knot in your stomach, call me now, not when it's a crisis. We'll work out a way through that's fair to them and to you. And ideally, one where you're still mates at the end.
