How to Screw Up a Friendship When You Become the Boss

A lot can go wrong when you transition from buddy to boss.

I don’t know about you, but I think learning about what not to do can be more effective than hearing about what I’m supposed to be doing. (There’s something there about the motivation of avoiding pain vs. seeking pleasure, which we could delve into in depth, but that’s not for today).

Today I’m here to talk about how to wreck a perfectly good friendship because yay! you got promoted, and maybe didn’t handle the transition from buddy to boss with the utmost grace. Managing your friends can be full of minefields. Because I have a lot of experience in the leadership mistake-making department (and I get to work with smart clients who have a made a few mistakes of their own), I’m able to shed light on the ways we mess this already-complicated situation up. Do these things if you want to ruin a perfectly good friendship with a friend who now happens to report to you. (Or, do the opposite, if you want to preserve the friendship. Whatever motivates you.)

Make sure you don’t acknowledge the potentially awkward situation at hand.

Everyone knows it’s weird when you go from buddy to boss, but in the interest of wrecking your friendship, don’t take the five minutes to acknowledge this and talk about how important your friendship is and how it will likely evolve. Don’t prioritize the need to talk about the boundaries of friendship and supervision, that there’s room for both if managed well together. Just sit back and watch your friendship go downhill in a hurry.

Ramp up the company trash talk, big time.

Just because you’re the boss it doesn’t mean you have to earn the respect of your team. It’s more important to try to be liked (then fail miserably at that in the end anyway). If you used to spend 30% of your lunch hour bitching about work, ratchet it up to 60%. (When you’re the manager, bitching is called venting.) People love a boss who complains about the company a lot; it makes them feel really proud of the organization and motivated to do hard work.

Tough love isn’t just for parenting.

It’s really important to let your whole team know that just because you and Kristi do karaoke every single Saturday night together, you’re a professional and you don’t have favorites. Treat Kristi like garbage and the point will be made: criticize her more often than others, make sure her ideas are dismissed on a fairly regular basis (even the good ones which you can “come up” with later and take credit for in the end anyway), and get really close at work to Reggie (a guy you’d never invite to karaoke, let alone share the stage with on a Saturday) just to prove the point, again, that you don’t have favorites.

Friendship means never having to say you’re sorry.

If relationship annihilation is your goal, stay above the apology fray. If you’ve been unfair to Kristi and want to acknowledge your missteps in a moment of real vulnerability, remain silent. If you know you’ve been avoiding giving feedback to George because you double date every month and the situation is just plain awkward, don’t apologize for surprising him with a 2 on his performance review. Remain silent.

Think like a shark: when you smell blood…

You have the inside scoop on your friends. You know where their weak spots are, like how Derek fabricated half of his resume, like how Sophie feels like a fraud, like how Andy has one foot out the door. Don’t reassure them when you go from co-conspirator on Friday to manager on Monday that you want to work with them to get better and do great things together. Exploit their weak underbellies. Attack, like a shark.

Defend your beer pong championship title to no end.

You worked hard for that office beer stein trophy. Some managers tone down their booze-infused escapades in an attempt to appear professional – but not you. Take team bonding to the next level as the life of the party who doesn’t care about being respected. Never be the first to go home, and when you do go home, make sure it’s with a lampshade on your head. Show up at the 8 a.m. status meeting hung over with the lampshade still on. R-e-s-p-e-c-t.

Let it all go to your head.

Don’t miss an opportunity to let your friends-now-subordinates know where you stand in the hierarchy of things. Post to the org chart prominently above your desk. Talk at length about the executive meeting schedule that they don’t need to worry about. Remind them, as often as needed, that supervision is Hard Work. Use the word subordinate a lot, which is always an employee-favorite. They will reward your inflated ego by sliding from friend to acquaintance to subordinate to former employee in no time. Mission accomplished!

If you’re in a company where you’re working towards a promotion, chances are you’ll reach that goal and then have the awkward task of leading the very people you’ve befriended along the way. There’s no perfect way to navigate this transition, but with a lot of hard work, you can isolate yourself from pretty much everyone and systematically kill off every work-friend you’ve ever had. That’s why they say it’s lonely at the top, right?


Jodi Wellman

Jodi is a co-founder of Happy Work Spectacular Life, loves red Skittles (maybe too much) and is contemplating where to get the Happy Spectacular logo tattooed on her body.

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