Letting Someone Go: How to Do It With Clarity and Care

Not because they don't see the issue. Because they care, they hope, and they don't want to hurt someone. That hesitation is human. But avoidance compounds the damage. Every day you delay, the team sees it. They're watching how you respond to underperformance - and they're drawing conclusions about what the culture actually is.

The Reframe That Changes How You Think About This

Early in my career I thought of my team as a family. That framing worked for a while. But families are unconditional. Teams are not.

The better mental model is a high-performing sports team. Every person is on the field because they add value, show up consistently, and make the people around them better. When that's no longer true, it affects everyone. Letting someone go doesn't mean you don't care. It means you're choosing the team over the discomfort of a single conversation.

Knowing When It's Time: Performance vs. Fit

Not every underperformance situation calls for the same response. There's a meaningful difference between a coaching problem and a fit problem, and treating a fit problem like a coaching problem just delays the inevitable.

A useful lens: look at performance and impact together, not separately. Low performance but high impact? There may be something worth working with, clearer expectations, better support, or a different role. Consistently low performance and low impact? Rarely a coaching problem.

One question that cuts through uncertainty: would I hire this person again for this role today? If the honest answer is no, you have clarity. What you're carrying at that point isn't indecision. It's a decision you haven't acted on yet.

When a PIP Is the Right Tool

A Performance Improvement Plan isn't a formality before a termination. Used properly, it's a structured, transparent opportunity to course-correct, with clear expectations, genuine support, and a defined timeline.

A PIP only makes sense when you genuinely want to retain the person if they improve, expectations have already been communicated clearly, and this isn't the first conversation about the issue. A PIP should never come as a surprise. If you haven't already had direct feedback conversations, start there- don't jump to a formal plan.

How to Actually Have the Termination Conversation

Be direct in the decision and human in the delivery.

• Be clear that the decision has been made. A termination is not a conversation — it's a notification. Hedging or circling creates confusion at the worst moment.

• This is not a feedback session or a recap of everything that went wrong. The person doesn't need a summary of their shortcomings. They need to understand clearly what's happening, what comes next practically, and that they're being treated with respect.

• Give space for emotion. Stay grounded. Calm, steady, and compassionate is what people carry with them after these conversations.

• Where possible, give them ways to leave on their own terms. How someone exits your company says everything about your culture.

What the Team Needs After Someone Leaves

The people who remain are watching. How you handle the exit, whether you're clear, fair, and consistent, shapes how much they trust your leadership going forward. You don't need to share details. You do need to communicate that a change has been made, what it means for the team, and that you're moving forward.

Founders who lose team trust after a departure are almost always the ones who communicated nothing. Silence creates a vacuum. People fill vacuums with the worst available interpretation.

Frequently Asked Questions

How long should a PIP typically last?

30–60 days is standard for most roles. Long enough to see real behavioral change; short enough to limit the cost of a prolonged underperformance period.

Should I tell the rest of the team what happened?

Not details, but acknowledge the change directly. Something like: 'We've made a change on the team. Here's what it means for how we're organized going forward.' Anything less creates speculation.

What's the biggest mistake founders make when letting someone go?

Waiting too long. The cost of delaying, to the person, the team, and the business, is almost always higher than the discomfort of acting sooner.

The full Hiring With Confidence bundle inside The DTC Operator includes the Performance vs. Impact Matrix, the complete PIP structure and conversation guide, the termination process step by step, and the team communication approach that maintains trust through the transition. It's $79. [Get the bundle →]