Esquire Theme by Matthew Buchanan
Social icons by Tim van Damme



How to fire a colleague but keep a friend.

I have a bit of sticky situation. I have a friend with whom I sometimes work in a professional capacity. More specifically, it is my business, and I have hired him from time to time. While his output is generally good—i.e. he is skilled at what he does—everything else is quite bad. He misses deadlines, is arrogant, brusque, and refuses to accept responsibility. What’s more, constructive criticism has not seemed to do the trick. How does one fire a colleague but keep a friend?

I sort of assume that you’re asking me what lie you ought to tell. Are you? Because I think if you’re going to fire him but you wish to continue the friendship, you should probably lie. Honesty is not always the best policy, and whoever said that obviously was a reductive asshole who didn’t have any friends.

Now, if you hadn’t included the last sentence—if you didn’t wish to preserve the friendship—I would probably not counsel lying. I might counsel telling him kindly, but firmly, that he’d been a disagreeable person with whom to work. And that might, in fact, be the “ethical” thing to do. If he’s being disagreeable with you, he may well be disagreeable in work with other employers, which bodes ill for his professional prospects. I also wonder how much fun it is to be friends with someone who behaves this way (to anyone, but especially to a friend who is paying him!). But you didn’t ask about ethics or the advisability of fraternizing with arrogant people, so we will talk about evasion.

First, though, for the sake of his future, make one last ditch effort at explaining to him what he’s doing wrong, in polite terms. Try a new medium: if, in the past, you’ve tried constructive criticism via email, try it in person, or vice versa. It’s hard to say, “Stop being so brusque!” But there is language for this type of thing. Sometimes pointing out that someone is being obnoxious is enough. For example, “Are you irritated about something that I (or another employee) have done? You seem a little put out.”

If that fails, we move on to getting rid of him. You could lie in a few different ways. The way in which you lie will depend on what kind of a person he is, and the nature/degree of openness of your relationship. So, for example, how many follow-up questions is he likely to ask in a slightly sticky social and professional situation? Most people don’t want to have conversations with friends about why said friends have suddenly found them obsolete. But don’t bet on that—some people would like nothing better, or cannot restrain themselves! So the tactic you choose will depend on him, and your knowledge of him.

If you think he’s not likely to probe much, you could say that it’s too hard for you to work with a friend, or that it’s harder than you thought, and that you’re having trouble being a boss to a friend. If he is likely to probe or argue his case, a more straightforward and less squishy lie (though more untrue) is to say that it’s too hard for the business to pay him what he’s worth and you need to bring in someone who is more junior/entry-level. A third option is to gradually ask him to work on fewer and fewer projects and hope he never asks what’s up. If he does, you could employ the entry-level explanation, or suggest that you are phasing out the kind of work that he does. These will have to be plausible lies in which you are unlikely to be caught. Think them through. If you’re planning to replace him with a world-famous hotshot, you can’t claim that you can only afford to pay someone who just graduated from college last week, obviously. You might consider the direction of your business more generally: are there areas into which you’re hoping to expand, or ways in which you’re hoping to change your work, about which someone other than your friend might have more expertise? If that’s the case, it could be a way to frame your gradual phase-out of him. It’s true that “we’re going in a new direction” certainly rings cliché (and hostile), but you don’t need to say it quite like that. Nor, in my opinion, do you need to treat an arrogant and brusque responsibility-avoider with kid gloves. But there I go again, changing the agenda.

In short: locate a version truth or a plausible lie that you are comfortable saying out loud. Think out various contingencies before you act. But don’t forget that this is your business, and you are well within your rights to run it in the way that you see fit. (I find this song very inspirational in such situations. Just kidding. Mostly. But I mean, look at that “Screw you!” expression. And those vertical stripes! Oh, just lovely.) And good luck! I’m very sorry; that sounds like a seriously quease-inducing situation.

Also, sorry that I keep telling people to lie. But like I said, who wants to be a reductive asshole with no friends?