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Dear Founder,

I’m sure you’re somewhere between being pissed off that you are being deserted, and worried about what you’re going to do to make up for this person’s contributions. Maybe you’re even more concerned that this will be the start of an avalanche—how many more people are thinking about leaving?

TAKE A DEEP BREATH. If you become as successful as I hope you will, this will be the first of many people who will leave over time. It always hurts when a key contributor leaves.

Before I give you my recommendations, let me start with a fun and true story.

Two co-founders of one of our successful breakouts asked to meet me to discuss a serious HR problem. They said that one of their early stars now had turned into a big performance problem. They wished they could fire him, but there was an issue: his dog was universally loved by everyone. The founders thought people would really be bummed to see the dog go. My advice: fire the employee and keep the dog! I was just kidding, but I was serious that they needed to address the problem. (They did, the dog left too, someone brought a new dog in and many years and hundreds of employees later we still laugh about the story.)

My advice for when you’re about to lose someone who means a lot to the organization:

  • Find out why they’re leaving. Are they running away from something or running toward something? Do they have their heads on straight regarding the situation?
  • Are they salvageable? If there is something wrong, can you fix it?
    • I always use additional compensation as a last resort, as it’s usually not compensation that makes someone want to leave.
    • If you can fix it, is the person mature enough to re-commit and be wholly engaged?
  • If you think they are salvageable, still do a gut check and make sure you’re not getting gamed. Sometimes people use the threat of leaving as a way to angle for more money. Unfortunately, people sometimes do disingenuous things. I’ve experienced situations where people have lied about the size of a job offer. You want to give people the benefit of the doubt, but you do have to be careful too, as you don’t want to build an entitlement culture where people think that if they threaten to quit they become eligible for a promotion. This will make costs go crazy and will render you powerless. Reserve the times you are willing to go through heroics for 1% of the employee population—the true talent—not 30-50% of the people who are trying to get a better offer. Everyone knows what’s happening, and you have to be mindful about how they view your response. If you aren’t careful, soon everyone will be at your door with a counter offer and a request for a raise and promotion. How can you tell what’s what? Probe where they’re going. Then tell them that it sounds like a great opportunity and that if it doesn’t work out they are welcome to come back.
  • If they definitely will be leaving, can you negotiate a transition plan that’s beneficial for both of you? Can you get their agreement to help out in a pinch even if they’re in a new job?
  • Treat them with respect and dignity on the way out. Celebrate their contributions and let them know they are welcome back if things don’t work out where they’re going.
  • But remember, you need to celebrate the people who stay and do good work as much as—or more than—the folks who leave. I’ve heard people say they only got recognized when they left (the squeaky wheel gets all the grease syndrome), which leads to very bad cultural dynamics.
    • Make sure the team knows that the departing person will be missed, but talk about the actions you can take and they can take to ensure the company will still achieve its dreams.
    • Recognize that this is a great opportunity for someone else to step up and get a promotion.
  • Finally, look back and assess whether this was a surprise. Did you see it coming? Make it a point to proactively know where all your key talent stands and work hard to keep them motivated and in the game.

I know it’s a big loss and a big hassle to have to deal with a key hire departing. But, it’s totally normal and manageable. Get through the pain quickly and elegantly, and get yourself back to terra firma as fast as possible.

All the best,

Maynard