How startups can fire with compassion

Adapted from my 4/1/19 Twitter thread by request

Pretty much all startups/young founders struggle with firing, but we don’t talk nearly enough about it. It’s one of the most difficult parts of leadership, but we *can* make it a lot less painful with a little bit of process.

So here’s the advice I share regularly with founders, with the hopes it helps you examine your current process and see opportunities for improvement!

First, to learn to fire well, you must:

  • Accept your responsibility as a manager and avoid externalizing the blame. (“That person is just terrible” is a too simple of an explanation for a nuanced situation. Plus, you were the one who hired them in the first place!) Another thing to watch out for is being stuck in paralysis.
  • Balance being human/kind <> upholding accountability & performance. Empathy & listening skills will take you far.

#1 rule: No one should ever be surprised with a “you’re fired.” That’s how you create disgruntled employees, embarrassing Glassdoor reviews, dip in team morale, etc.

An out-of-the-blue firing is a failing on the *manager’s* part, not the employee’s.

2. Confront the issue early. Does the employee *know* that they’re not performing? Are you confident you have all the info, or could there be context you’re missing?

Instead of sitting on your hands / jumping to conclusions, practice having direct (but kind!) convos early!

3. Give them a fair shot to improve. As a leader, it’s your job to try to make it work, each employee is owed that.

Practice listening skills. Demonstrate that you believe in them, and you *want* to see them improve. Commit to giving a LOT more feedback (specific & documented).

4. Sometimes simply doing the above solves the problem. In which case, yay! You’ve turned around a struggling employee! 👏 (new Manager Level unlocked!)

If not, it’s time for more serious action. Loop in HR/Legal if they haven’t been already — make sure you’re in compliance with local/state/fed requirements.

5. Create a Performance Improvement Plan: an official, *written* agreement that outlines exactly how an employee needs to improve to keep their job.

Like an actual firing, a PIP shouldn’t come as a shock either.

Presenting a PIP means it’s the 11th hour — the manager should commit to giving even MORE feedback. Final chance to make it work, give it your best effort.

6. You can offer an “out.”

This is a process I’ve seen work out very well. At the same time as the PIP, present an alternative: “You can go through the PIP, or a severance now to get a head start on your job search.”

Here’s the logic — you’re going to have to pay their salary anyway, so that’s a wash. The real value is freeing up the manager’s time, a precious resource.

I’ve had many employees take it, in certain situations it provides relief for all parties in very challenging situations.

Employees are less likely to be disgruntled if they leave on their own terms. But they HAVE to believe that you really tried to help & gave them a real shot.

7. Be mindful about departure communications. This is always going to be hard, b/c of the need to balance *transparency* (people are naturally curious) vs. *privacy* (how would you feel if it it was happening to you?).

There’s no one right way to do it, use your judgment and aim to learn from each situation.

[Note:] All of the above goes out the window for cases involving violence, harassment, fraud, etc. when safety & integrity of the team are at risk. ⚠️🙅🏻‍♀️ Investigate, then move quickly and decisively.


This thread of advice might not work for everyone, but it is a starting point for fast-moving teams who have yet to build a process.

It should be iterated on/adapted to the context. Every termination is personal & nuanced — this is about people’s livelihoods after all.

I’ve seen the gamut w/ firings — good/bad/ugly — and that’s why I want to see more teams be better at it! Feel free to DM me for more resources, and I’m available for consulting on this topic + all things startup team building. 👋

We’re all learning together. You don’t need to know all the answers, just how to ask for help. Your employees are counting on you 🌟


Thanks for reading! I write/tweet regularly about all things related to scaling startups, leadership development, Diversity & Inclusion, the tech employee experience. Follow for more content: @jenistyping.