We need to talk about That One Team Member.

You know the one. Lovely person. Great chat. They can do the job (in theory), but somehow, they never seem to do the thing you keep asking them to do. Not unless you remind them. Repeatedly. In seventeen different ways. It starts off as a mild annoyance, like misplacing your keys. But then it snowballs. You find yourself getting more and more irked. You rewrite their to-do list in your head. You chase them up (again). You question whether you were clear. You wonder if they care. You question everything. Eventually, it hits breaking point. You either: – Snap and go full “shouty boss” (which feels gross), or – Sigh and do it yourself (which feels worse). Either way, you end up pissed off, depleted, and wondering whether it’s you.

If this feels painfully familiar, you’re not a terrible leader. You’re a human being who’s trying to run a business and not lose your mind in the process. But the uncomfortable truth is: this keeps happening because you’re letting it.

Oof, I know. Sorry not sorry, but stay with me.

What most business owners don’t realise is that the problem isn’t just with the team member, it’s with the dynamic. A pattern has formed. You ask, they delay. You remind, they ignore. You get louder, they tune out. Eventually, you either give in or blow up. It’s not working. For either of you. What this situation actually needs isn’t another reminder, or a rage-fuelled Slack message. It needs clarity, boundaries, and a pinch of assertive leadership. Not aggression. Not passive-aggressive Post-Its. Not martyrdom with a side of resentment. Assertiveness.

The ability to clearly state what’s expected, hold people to account, and lead like a grown-up (even when you want to scream into a pillow). It sounds simple, but most of us were never taught how to manage like this. Especially if you’ve gone from solo operator to team leader almost by accident. Or if you’re a natural people-pleaser who hates confrontation and would rather just “pick your battles.” Now, you can turn this around without turning into a dictator. You can stop the cycle, you can set new standards, and you can do it in a way that actually earns you more respect, not less.

But it starts with making a decision: to stop tolerating what’s not working.