It’s an intriguing question that Harvard Business Review recently addressed. Is it possible to be friends with your boss? Unfortunately, after a litany of qualifying questions, the ultimate conclusion was that it “depends on your personal preference.” Well, Harvard Business Review, if that’s the only thing that matters, then why am I reading your article in the first place? Is it possible to eat a peanut butter and jelly sandwich upside down while engaging in anal sex? I don’t know, I guess it “depends on your personal preference.” Thanks for the non-answer, dillweed. So in an effort to do what HBR elected not to do, I’m going to definitively answer the question. Yes, you can be friends with your boss.
HBR brings up a good point in that a friendship with your boss won’t work out if you have ulterior motives for the relationship. Well, that just remains true for life in general. If you’re trying to be friends with any people for ulterior motives, be it that they’re rich and you’re a mooch or they’re hot and you’re stupidly hoping you can be friends with them for long enough to get a bangarang out of the deal, your friendship probably won’t go well. This point really goes toward the whole concept in general. If you’re trying to be friends with someone for a shitty reason, it’s probably going to end badly.
Let’s look at HBR’s example of how being boss and underling friends can be an issue. Here, the friends are Jason (the boss) and Martin (the employee). Somewhere along the way, they had a falling out and stopped being buddies. Then it was weird at work. Well, yeah, ding dong, that’s what happens when you have a falling out. If I have a falling out with one of my friends, it’s weird when we run into each other. So then Martin eventually moves to another company and Jason seems relieved. You mean like how millions of people move to new companies and their bosses breathe a sigh of relief every year? I’m not sure the whole friendship/breakup dynamic is the biggest issue in this story.
Here’s a nice little anecdote of my own. My roommate’s boss is friends with him. Actually, he’s friends with all of us. He was friends with my other roommate first, because that roommate interned for him. When that roommate’s brother moved out, he got him a job with said boss. Now both roommates are friends with the boss, friends with me, two of them are brothers, and you’re totally confused. It’s okay, so are we. The point is, my roommate’s boss is a cool guy who hangs out in our group, hits the bars with us, and invites us over to try his new recipes because he’s a foodie, and I’m okay with that because I like food. How does it work? Well, it mostly works by neither of them being morons. It’s seriously that simple. When two people are friends, they know each other’s limits and vulnerabilities, which only strengthens the boss/employee relationship, provided you aren’t a douchebag. My roommate might be his assistant, but his boss knows that he wouldn’t be able to function without him. They have a mutually beneficial parasitic relationship. I think that’s called symbiosis, but I slept through science class. Which one? All of them. Why do you think I write for a living?
The point is, the answer to this question isn’t nebulous or up to personal preference, it’s just dependent on you not being an asshole. Yes, if you, as the employee, are trying to befriend the boss to move up, it’s probably not going to go well. Yes, if you’re the boss and you manipulate your friendship status to get your employee to do more work, it’s probably not going to go well. I don’t think this is all that complicated. If you’re a dick, this friendship will crash and burn, which shouldn’t come as too much of a surprise, because if you’re a dick, all of your friendships will crash and burn..