Every entrepreneur eventually reaches the same crossroads: the moment you realize leading a team isn’t just about inspiration or delegation – it’s about communication. And not just the fun kind. We’re talking about the awkward, emotional, high-stakes moments most people try to avoid.

These are the hard conversations at work.

They show up when someone’s not pulling their weight. When a team member asks for a raise you can’t give. When someone’s behavior starts to chip away at your culture. And they don’t get easier just because your business is growing.

But here’s the truth: if you’re building a team, these conversations aren’t optional. They’re inevitable. And your ability to handle them – directly, humanely, and with structure – is what defines you as a leader.

Let’s walk through the three hardest conversations you’ll face as a business owner, and how to approach them in a way that builds trust instead of breaking it.

Addressing Performance Issues

This is hands-down the most delayed conversation for new managers. You see someone missing deadlines, making mistakes, or not owning their work – but because they aren’t being disruptive, you let it slide.

The problem? Silence sends a message. And while you’re quietly fixing their work or waiting for improvement, the rest of your team starts to wonder if performance really matters.

Here’s how to do it right:

• Be direct, and focus on facts – not feelings.
• Clearly describe what’s not working and how it’s impacting the team or business.
• Define what improvement looks like, and by when.
• Offer support and resources to help them succeed.
• And always follow up in writing – not just for legal reasons, but to ensure shared clarity.

Handled well, these conversations become turning points – not endings.