Why Founders Can’t Outsource Difficult Conversations as They Scale

I meet so many brilliant founders who can build a brand from scratch, but feel stuck when it comes to difficult conversations.

This has come up repeatedly over the past year. More than one founder has said some version of, “I don’t do difficult conversations. I’d rather someone handle them for me.”

I get it. They’re uncomfortable. They take energy. And early on, it can feel easier to hand them off.

But as you scale, you simply can’t outsource every difficult conversation.

There are too many of them. And when they’re avoided, small issues quietly turn into big ones.

So instead of becoming the permanent “difficult conversation person,” my approach is different: I handle the immediate issue and teach you the skills to do it yourself as you scale.

Founders don’t need someone swooping in every time tension shows up. They need the confidence to have the conversation quickly, fairly, and move on with running the business.

Here are three difficult conversations most growing brands face:

1. Delayed performance conversations Small issues become big ones when they’re left unaddressed. Rework and missed deadlines can quietly cost 10–20% of weekly output.

2. Unclear or inconsistent compensation conversations Replacing a frustrated high performer often costs 50–125% of their salary.

3. Role clarity conversations when the business outgrows someone Teams with unclear roles can lose up to 30% of their execution speed.

Difficult conversations don’t get easier by outsourcing them.

They get easier when you learn to do them yourself, consistently and fairly.

That’s how you protect the business, support your people, and keep everything moving forward.