When Good People Leave
One of the biggest gut-punches you can take as an operator, builder, or manager is when a good person on your team decides to leave. Especially if you weren’t expecting it. Odds are you are understaffed, overwhelmed, and desperately need that person in their seat. Your first reaction will be to save them, but if they’ve already told you that they’re leaving you’ll be too late. How do you right the ship, cover for that person, and do your best to make sure everyone is still happy?
Getting this wrong means risking that this person is likely the first domino of many to fall. Getting it right means solidifying your team and leaving this period stronger than before. When faced with this situation I consider three things: The Moment, The Team, and Lasting Change.
The Moment
When a good person tells you they've decided to leave you have three goals. Your goal in the moment is to..
Control your emotions
How you handle yourself when someone tells you that they’re leaving will define the outcome. Blowing up, throwing a fit, and making a public scene will cause your team to fear you and the person leaving to resent you. Neither is a good option. When having this conversation it’s paramount, absolutely paramount, that you remain calm and control your emotional swings.
Understand why
Instead, when notified that someone is leaving, you first need to understand if they’re genuinely leaving or if they’re floating a trial balloon. Neither is good, and both will require action but different actions. A direct and straightforward “are you sure?” is usually sufficient to suss out their intentions. If they’re leaving, DO NOT FIGHT THEM ON THIS. Even if you convince them to stay for a short period, keeping someone of low morale around will infect their peers. Being halfway out is a contagious disease in a growing company.
Once you have your answer, you can work on the next steps. Provided they’re leaving, you’re going to want to understand as much about their decision as possible to make sure the rest of your team is secure and you have the opportunity to fix anything you might be blind to. You’re going to want to conduct what an HR team would call an “Exit Interview,” it’s a series of questions designed to figure out what happened, surface issues to fix, and understand what the company can do in the future. Like any good root cause analysis, it should be blameless. I’ve found that once people are in an emotionally safe zone regarding their decision and departure, they’re usually voracious in their explanations of what to fix.
Make a plan
Finally, you need to make a plan with the person. The plan should include clear next steps around them documenting their current work streams and projects. Once documented, you should align on the exit date and communication plan. I think that someone who quit without giving notice should leave ASAP and should probably not return to the office (or digital office). That doesn’t mean that you shouldn’t do an exit event, just that you shouldn’t let them linger.
The Team
If you handled things well with the departing team member, you should be set up for success with the team. Here’s what you should do next:
Map and engage their peers
Set up 1:1s in the leaver’s sphere of influence. Set up as many as you can for the next few days. Focus on any cynical or skeptical team members.
Prep for communication
You completed the exit interview in order to compile useful information about what needs to be fixed. Now is the time to 1) make sure you’re fixing those things (provided that they are real and urgent) and 2) create a comms plan for you and your managers to talk to those things. That comms plan doesn’t need to be crazy complex, just bullet points about next steps, actions and work streams.
As you do this, you should send the comms out to the team. I suggest having the leaver send an approved message that is short and sweet that gets followed by a note thanking them from the CEO or appropriate leader.
Whatever you do, do not degenerate the leaver. You should never say things like “we were going to fire them anyway,” “they weren’t that great.” “or this isn’t a big deal.” Your team is looking to you for leadership but they’re also looking at how you respect their peers. People will start to assume that you don’t respect the team if you say things like that. Trust will go poof!
Celebrate
If someone worked at your company for a while (greater than a year), you should celebrate their contributions. Have someone close to them plan a happy hour, lunch or similar activity 2-3 weeks after the announcement of their leaving. Staging it out a few weeks will allow any hot tempers to cool and give you time as a leader to deal with any of the issues that need to be addressed. If you do it too soon, it might have the unintended consequence of accentuating smoldering issues.
I’m a big believer that leadership should attend things like this. It is a visual representation of caring for your people. You’re showing your current team that you care about someone that is leaving -- this is the emotional bookend to handling the initial quitting conversation well. You don’t need to stay out all night, but showing up and saying something nice will go a long way.
Lasting Change
If you’ve navigated the above well, you’ll no doubt want to avoid it in the future. Here are a few tips for doing that.
Stay interviews
If you have a people team, I recommend having them do “stay interviews.” Stay interviews should be similar in content to the exit interview, but be completed with employees who are currently at the company. The people team should uncover and investigate issues and complaints.
Transparently fix things
When you identify issues you should be transparent with the team about the issues and transparent with the plan to fix them. People will give leadership a lot of rope if they admit they’re aware of issues and articulate the hypothesis for fixing said issues. The team loses trust when leadership doesn’t recognize issues. You can communicate what you're working on through all-hands or written updates, but either way, focus on building trust by delivering against your commitments.
Winning solves problems
Winning is a panacea. If a person leaving was due to stagnation or slowness in the business, you need to address both the root cause and manufacture ways to win with the team while fixing the root cause. People feel better about their environment when they perceive themselves and their company to be winning.
Draw a line
Sometimes people get fixated on the idea that “things have changed.” Of course they have, it’s a start-up. If you’ve all done your jobs well, a whole bunch of stuff should be changing. Occasionally, these early employees can be a hindrance to the required growth and change. You’ll need to eventually draw a line between the old and the new in cases like this. You need to work with each tenured employee and get them to commit that they’re on board with the new ways. They can disagree, but they need to commit, and not complain.
Don’t take it personally
As a leader, I’ve always taken every person leaving my company or team personally. This seems to be a natural byproduct of caring, but if you take it personally every time, you are doing a disservice to yourself and the company. Things change, roles change, and people change -- it’s not going to be right for everyone all the time. When someone leaves, learn what you can, fix any issues, and move on.
Wrap up
It sucks when someone great wants to leave. If you follow the steps above you’ll have a plan for limiting the chance of it happening again and building a stronger culture. Just make sure that you don’t take it too hard -- every great story has their moments of failure.