When to Let Someone Go

SDS 056: When to Let Someone Go

Hey! thank you for reading issue 056 of Startup Definition Sunday (SDS). You can read past issues here.

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I just got back to Nairobi after a busy week doing due diligence in Lagos. Amid the hustle, I managed to catch up with some amazing friends who are building transformative businesses in Nigeria.

One of the most thought-provoking conversations I had was about one of the hardest decisions any founder faces: when to let someone go.

Let’s face it—no one enjoys confrontation, and firing someone is never easy. But in a fast-paced startup, the ability to make tough decisions quickly and thoughtfully is critical to your company’s success.

If you’re a founder wondering when it’s time to let someone go, here are three key signs: consistent underperformance, misalignment with company values, and negative impact on team morale.

In today’s issue, I’ll share 3 actionable tips to guide you through this difficult process while helping you retain the best talent.

Define Clear Performance Expectations

From day one, be transparent about what success looks like. Communicate goals, deliverables, and the metrics you’ll use to evaluate performance. Regular check-ins and documented feedback are essential to avoid surprises down the road.

If someone is consistently underperforming, keep a paper trail of missed deadlines, behavioral concerns, and other issues. When it’s time for a tough conversation, you’ll have concrete examples to refer to. Sit down with the employee, explain the concerns clearly, and give them a chance to improve with specific goals and timelines.

Implement a "Failure to Improve" Policy

Offer underperforming team members a structured opportunity to course correct. Set a timeline (typically 30–60 days) and clear improvement goals.

Rather than jumping straight to termination, provide resources, training, or even consider another role that might better suit their skills. If they still fail to meet expectations, you’ll need to part ways. This approach shows you genuinely care about their success, even if it’s not within their current role.

Ensure a Dignified Exit

When the decision to let someone go is final, handle it with empathy and care. Make the transition as smooth as possible by:

• Offering a severance package (if feasible)

• Providing a reference or assistance with their job search

This not only preserves your company’s reputation but also maintains a positive relationship with the individual—you never know when paths might cross again.

My Two Pesewas

Remember, great companies are built by great teams. Letting go of the wrong people is just as important as hiring the right ones.

While firing someone is never easy, taking a thoughtful, process-driven approach can minimize the stress for everyone involved. By setting clear expectations, giving people a fair chance to improve, and handling exits gracefully, you can protect your company while fostering a team of top performers. 

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That's all for today. As always, thank you for being an engaged reader. Let me know your thoughts on this issue. I’d love to hear your experiences or tips on navigating tough decisions in leadership.

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Until next time,

Jasiel

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