When Great People Leave

How to react when a key employee tells you they are moving on

Building a company is akin to riding an emotional rollercoaster with highs and lows you experience on a daily or even hourly basis.

One moment you’re walking out of a customer meeting having just agreed on terms for a multi-year contract that you’ve been through the ringer on with legal, their finance and procurement teams. You walk into your next meeting, a 1:1 with one of your top engineers expecting to talk product roadmap. And that’s when they let you know they’ve accepted an offer from another company.

Down we go.

Image credit: ChatGPT

The Gut Punch is Real

When someone leaves, particularly when you’re still a small team, it can feel devastating. You’ve worked late nights together on getting a customer feature rolled out before a demo. You’ve traveled to conferences looking to drum up new leads. You’ve recruited other people to the team.

This person wasn’t just an employee, they were a believer. Someone who signed up for the uncertainty, the lower pay and equity that might never be worth anything, the long hours and the constant adapting to the market. And now they’re...leaving?

It can feel like a betrayal.

The emotional reaction is understandable, but it’s also important to remember not to take it personally.

Step 1: Figure Out if They Can Be Saved

Before you spiral, take a breath and ask yourself: Is there a way to convince them to stay?

Most often, the answer will be no. By the time someone sits you down for “the conversation,” they’ve typically already mentally moved on. They’ve gone through an entire interview process, negotiated terms, and made a decision. And then they have gathered the courage to finally tell you. That’s a lot of psychological momentum to overcome.

But it’s worth exploring. Maybe there’s something you can address - a role change, additional responsibility, a compensation adjustment, or even just a more flexible work arrangement. However, be honest with yourself about whether any fixes would be sustainable, and perhaps more importantly, fair to the rest of your team. Paying one person significantly more than others, for example, or giving them special privileges to stay often creates more problems than it solves.

Step 2: Understand the Why

Assuming they’re truly committed to leaving, your next job is to understand why. And I mean really understand, not just accept their polite explanation about “pursuing new opportunities.” Because, for someone to leave a startup they previously believed in, a concrete sequence of events had to take place:

1. Something changed at work that made them question their fit, growth trajectory, the opportunity ahead for the company, etc.

2. They became more amenable to taking calls from recruiters and going through interview processes

3. They found something more attractive at another company, whether it was better compensation, more interesting work, clearer career path, better work-life balance, or simply a company they believe has better prospects

It doesn’t happen overnight. So again, don’t take their decision personally, take it as data.

Spend real time with them understanding what attracted them to the new opportunity. Was it the money? The role? The company’s trajectory? The team they’d be joining? The location or flexibility?

This isn’t about changing their mind, it’s about learning what you might need to change to retain your current team and attract more great people.

Step 3: Handle the Transition with Grace

Assuming it’s not an acrimonious departure (and hopefully it’s not), how you handle their exit matters enormously both for them and for the rest of your team.

First, make sure you create a plan for picking up their responsibilities. Nothing creates team anxiety like critical work falling through the cracks.

Second, and this is crucial: sit down with your existing team and address the departure directly. Don’t make a big deal of it, but don’t pretend it didn’t happen either. A departure can be jarring for the rest of the team, particularly when they don’t have context. It’s human instinct for people to wonder, “What do they know that I don’t know?” and potentially question whether they should stay themselves.

Be transparent: “Sarah has decided to move on to pursue another opportunity. We’re excited for her and wish her the best.” Then use that moment to reinforce why you’re building what you’re building, where the company is headed, and why the remaining team is critical to getting there. Often moments like this can serve as a rallying cry for the rest of the team.

The Long Game: Alumni as Assets

Assuming someone leaves on good terms, stay connected. Celebrate their wins. Ensure they are proud to be from your business. Some of your best customers, partners, and even future employees might come through your alumni network.

I’ve seen former employees become customers, refer great candidates, and even come back as the company grew and their career goals evolved. But this only happens if you resist the urge to burn bridges when they walk out the door.

It Gets Easier (Sort Of)

As your company grows, individual departures will sting less. When you have 5 people, having one leave can feel like the end of the world. When you have 50 people, losing one great person is meaningful but not existential.

But here’s what I’ve learned from the founders I work with: every departure, handled well, makes you a better leader. You learn what motivates people. You get better at spotting early warning signs. You build systems that make your company more resilient to key person risk.

Most importantly, you learn that people leaving doesn’t mean you or your company failed. Sometimes great people leave great companies for reasons that have nothing to do with you.

The rollercoaster will keep rolling. There will be more highs and more lows. But each time, you’ll be a little better equipped to handle the ride.

---

What’s been your experience with early employee departures? How did you handle it, and what did you learn? Reply in the comments below.

---