When Your Friend Is Also Your Boss: A Cautionary Tale

by Logan Sachon

This series is brought to you by TurboTax Federal Free Edition.

Mike Dang: Logan, do you remember when I was your boss? Good times, huh?

Logan Sachon: Well, Mike, I do remember it, but apparently not the way you do, because I thought it was a terrible time.

Mike: Yes, well, becoming your boss was sort of an accident. We both started out as contributors to the website where we worked, and you sent me this really cute email saying you liked my writing, and I replied that I really liked your style too, and then we IM’d everyday forever. Yay! Best friends! And then I got promoted a bunch of times and became your boss. It was all very sudden, but also sounded like it would be fun.

Logan: The fun part for me was that I thought it’d be nice to not be scared of my boss anymore. (I’ve only had one Genuinely Scary Boss, but I think it’s healthy to be a little bit scared of the person who signs your checks, and so I usually am.) But I wasn’t scared of you because you were my friend — nothing scary about that! But not being scared of you resulted in me turning into the worst possible employee version of myself. I remember this really awful Dark Period of me sucking at my job and taking advantage of your friendship/boss-ship and milking your leniency and kindness in a not totally accidental way. And wanting to stop but not being able to stop. That was a drag and kind of stressful and awful for us both.

Mike: Well, I covered for you a lot, and I probably shouldn’t have done that. That made me a bad boss because it meant I was treating you like a friend — a friend who covers for his friend because he doesn’t want his friend to get in trouble with the boss. But that didn’t make sense because I was your boss. So I should have just made you own up to your mistakes so you could learn how to not repeat them. Lesson learned!

Logan: One not fun thing that I’m not going to do would be to see how many emails and Gchat conversations come up if I search “I’M SORRY MIKE” or “YOU SHOULD JUST FIRE ME” or “DON’T HATE ME BUT.” My approximate guess is that there would be at least one for every day you were my boss. Okay, I’m going to look one up. Okay, I’m done. I think I have PTSD from reading through those chats.

Thinking back on that time: I was sort of like a little kid, trying to see how much I could get away with. Every now and then I would have a small break and I’d smack my head with the realization that if I did my job well, I’d be helping you and making your life good, and that should be worthy! And then I’d do that for a second, and then… I’d stop. Because, you know, I wasn’t the boss, and as a lower-level employee, my job was to basically get away with as much as I could. This chat is not showing any of my best qualities at all, is it?

Mike: To be fair, half of it was my fault. See? There I go trying to cover for you again. But indeed, I really struggled with simultaneously helping you and taking care of business at the office. Because as a friend, I wanted you to be happy! I think this was all exacerbated by the fact that you worked remotely and I didn’t have the luxury of physically standing over you to make sure you were getting all your work done. I would often wonder what you were doing when you weren’t responding to my Gchats. So that is another thing I would have done differently — I would have made you move to New York and physically work out of the office.

Logan: I was reading blogs, Mike. That’s what I was doing. And yes, I think being in the office might have been better. I would also like to take this opportunity to say that I’ve never been fired from a job, and that I am (generally) a good employee and person. Thank you.

Mike: I will say that when I was not your boss, working with you was the best. We had a lot of fun times! I think this whole experience taught me that I am good at being a friend, and good at being a boss, but not good at being a boss-friend, because I was also managing ten other people who were not my friends, and that actually went really, really well.

Logan: I missed you as a coworker, when you were my boss. When we had other bosses, I used to IM you all the time with fun confessions about having not starting a post that I just told a boss was nearly done, whoopsydoops, la dee da. And you’d always be stressed out on my behalf, but also supportive. But when you were my boss, I couldn’t tell you the truth about the post having not been written, because you were the one I had just told I had written it. Very confusing.

You did give me a raise one time, as my boss-friend. Nepotism?

Mike: I gave you a raise and I remember how amazing it felt to be able to do that. Like, it was one time when I actually felt I had some sort of power! But you deserved that raise because I gave you more responsibilities, and this was when you were actually doing really great — before you started not doing anything, basically. And no, I didn’t feel like it was nepotism because I negotiated a raise on behalf of all our contributors, and when it came to you, I laid out your case to my own bosses, and they were the ones who approved it. As you know, I go through all the appropriate channels for these things.

Logan: Ha, yes, that was kind of a joke to see how upset you would get at implied nepotism. You are the most Moral and Ethical person I know.

I think we both could have handled the whole boss-friend situation better, but if anyone asked me for hot tips on how to do it, I would simply advise against it. Because, ultimately, worker bees and boss bees simply don’t have the same goals. Like, bosses want to get as much out of you as possible, and workers want to get away with as much as possible. Bosses should be bosses, and friends should be friends. That said, I think it’s okay for friends to be co-bosses. I think equal distribution of power would work for me/us (as it has worked for others, historically).

Mike: But I agree that the boss-friend situation is a very sticky situation that should be avoided at all costs, if possible. I think the best situation is having a boss with whom you are friendly, but not actually friends. You want to be able to fire or promote your employees without feeling that you are ruining a friendship or playing favorites. But perhaps there are boss-friends out there that have had nothing but amazing times, and if they’re out there, I want to hear about them!

Logan: I don’t think they exist. I would like to close with one more example of the bossfriend relationship not working out: Lord Grantham and Mr Bates. They were friends, then Lord G became his boss, and it was nothing but drama drama drama after that. Very trying, very taxing. I don’t think they’d recommend it, either.

Mike: I blame Bates for the whole Mr. Pamuk situation. He should have been quietly lurking the halls like everyone else, and prevented Mr. Pamuk from entering Mary’s bedroom.

Logan: Well it wouldn’t have been a thing if it wasn’t for his dumb wife. Don’t talk smack about Mistah Baaates. Also: Doesn’t it seem like it should be “Pamouk”? I feel like that spelling would be better.

Mike: You’re fired.

Logan: Too late! I quit.

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Mike Dang and Logan Sachon are happily just friends.