How To Be A Boss: Seven Tips For Hiring — And Firing — A Friend

When I first became a boss, one really tough thing was supervising my former co-workers and friends.

Kind of makes sense – right? You have to be a jerk sometimes and your erstwhile pals don’t take kindly to it. The bad: I lost a lot of party invitations. The good: the pay was better.

But the really hard part was, and has, been deciding whether or not to hire friends at all. A lot of entrepreneurs, for instance, do this during the startup phase. I did it at larger organizations, but still…it wasn’t a great when things went wrong. (Even when things didn’t go wrong,  you were always worried that things would go wrong – and how it would reflect on you.)

You don’t quite have that problem – you run the whole business after-all. But there are still some rules-of-thumb for founders who are considering hiring folks they have a relationship with.

1. If you have to hire a friend, only Hire “A” players. That means folks at the top of their game. Yeah, I know. You do that all the time. But you tend to cut your friends some slack. That’s life. But it only creates a lot of problems. Your better employees resent cleaning up after your talentless buddies – and may look elsewhere for work. Customers will be annoyed. Even if the “A” player is a jerk, at least he or she is a talented jerk.

2. Don’t Supervise Friends. If your “A” friend really has the chops, let your co- founder or a trusted employee run them. It isn’t always convenient, but it gets pretty uncomfortable directly supervising friends. And someone will always think you’re cutting them slack or paying them more or both.

3. Keep Your Door Open. I hired a friend to help me run a small magazine. He eventually left. When he did, a stream of folks came into my office to describe unspeakable stories of management malfeasance. I asked: “Why didn’t you tell me?” They replied, all of them: “Because he was your friend.” Jeez. The solution? Make sure all your employees know they can come to you if they have a problem.

4. Avoid the “Favor Syndrome.” Here’s how it goes. A friend will call you asking if you could give their friend, who “is really good,” some work. I have to tell you: This never, ever turns out well. If someone is calling you, that means their pal has been having trouble finding work. And you know what that means? More often than not often, that means they’re not very good.

5. Test Drives: See the “favor syndrome.” It doesn’t hurt to dole out a tryout assignment. If it doesn’t work, you may have to ghost your friend for a while. But it’s a lot better than friend-divorce. And speaking of which….

6. No Hard Feelings. I love this one. You tell your friend they have to agree that that the working relationship might not end well. And if it doesn’t, they have to leave and still like you. Well, it won’t work out just that way. But talking about it upfront helps.

7. Fire Fast. Yup, fire your friend if things aren’t working out. If you let problems linger, you’ll look bad to your co-founders, your employees, and your customers. You’ll lose your friend in the process, but so be it.

Your business, you know, is your only real friend.


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