The hardest part of entrepreneurship and leadership is having to let people go. It freaking sucks. After 15+ years running businesses, this task has never gotten easier. I still lose sleep before these conversations. I still carry a pit in my stomach walking in.
That discomfort, I've come to believe, is actually appropriate. If you stop feeling it, something has gone wrong.
Why It's Hard — and Why It Still Has to Happen
When you let someone go, you second-guess yourself. You wonder if you tried everything. You think about their family. You replay conversations wondering if there was a different path.
But here's a framework that helps me: think of it like shoes and feet. Some shoes feel great on one person and terrible on another. It's not that the shoe is bad — it's that the fit isn't right. Some people simply don't align with a company's environment, culture, or requirements. That's not a moral failure. It's a fit problem.
There's also the GWC test: does this person Get it, Want it, and Have the Capacity to do it? When the answer is no on any of those three, staying becomes unfair — to the team, to the business, and often to the person themselves.
Five Tips for Letting Someone Go
A phone call or email is not acceptable for this conversation. Show up.
You can be direct and still be kind. These are not mutually exclusive.
Whatever led to this moment, they are still a person. Behave accordingly.
Don't over-explain or hedge. Clarity is a kindness. If a decision is right, don't spend time apologizing for it.
How you handle this moment shapes how your team sees you as a leader. Be thoughtful about the message and the timing.
This is one of the necessary responsibilities of leadership. It never gets comfortable — and maybe it shouldn't. But doing it with integrity, speed, and humanity is something you can control.