Ask a Boss: I’m Going to Be My Frenemy’s Boss!

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Dear Boss,

I’ve been at my company for over five years and have been in several different positions, but am just taking on my first supervisory responsibilities. The trouble is that one of my direct reports, Tim, is someone I do not get along with (and that’s an understatement).

We used to work in the same position and were very good friends for a long time, but I ultimately found his friendship incredibly toxic. Based on the intimate knowledge of his life that I acquired when we were friends, I really believe that he needs therapy. When he used to come to me for advice, I suggested this a few times (and explained that I’ve turned to therapy for assistance in the past and found it helpful), but he has refused to seek professional help because he sees himself as a victim in all situations and always believes he is in the right.

To keep things professional and cordial at work, I have maintained a basic, superficial relationship with him since purposely drifting out of our close friendship. I am polite in the office but avoid all personal interactions as much as possible. This has worked surprisingly well — until now.

My new role as his boss was not a surprise, and things have been very rocky since he saw it coming. He has behaved very rudely toward me on some days — shouting to get my attention, interrupting conversations I’m having with other co-workers, telling me that I don’t know what I’m doing, etc. On other days, he has been so cavity-inducing sweet and polite that I cannot help but get frustrated at the level of his passive aggressiveness.

I am incredibly nervous about managing a group of people for the first time and I do not know how to tackle this additional challenge. I generally try to give everyone the benefit of the doubt, but I gave him a lot of chances and now he makes my skin crawl every time he opens his mouth. I find it hard to see any redeeming qualities he might have on a personal or professional level. The majority of our office feels the same way about him — he has been around for longer than I have and has offended almost everyone because of his attitude.

How can I approach being his manager? I know I need to be removed and impartial. I know I need to try to help him improve the way he interacts with other people in our office because (a) it will help him improve professionally (he desperately wants a promotion and feels personally attacked that he has been passed over for everything he’s applied for, even though he’s been told multiple times that his attitude is his No. 1 barrier to more success) and (b) his pettiness can really bring down an otherwise-happy team culture. But I am so distracted by my personal feelings that I don’t know where to begin with him or how to start to overcome this.

I do not feel comfortable going to my boss or new peers about this, because the level of my feelings would make me look like the unprofessional one. I have heard from his past supervisors that he is a nightmare to manage — and most of them used to be his friends, too!

Hey, welcome to managing: You get to deal with jerks! It’s actually better than it sounds, though, because you actually have the authority to do something about them.

That doesn’t mean that it’s easy though, and dealing with this kind of behavior tends to be especially hard for new managers. You’re still figuring out how to exercise the authority of your position appropriately even in more routine interactions, and a lot of new managers (hell, a lot of people) hesitate to be direct and firm when someone is out of line.

But here’s the key thing you need to know in order to effectively manage this guy and the rest of your team: As his manager, you now have a responsibility to shut this down. You can’t let him shout at you or others, rudely tell people they don’t know what they’re doing, or behave so poorly that he alienates most of his co-workers. Even if you were willing to tolerate him doing this stuff to you — which you shouldn’t be — you have a responsibility to the rest of your team to shut it down for their sake, because it’s incredibly unpleasant to work in an environment where someone is doing this. Moreover, if you let it continue, you’ll undermine your own authority — definitely in Tim’s eyes, but also with the rest of your staff, who are looking to you to use that authority when it’s called for.

That means that you’re going to need to talk with Tim one-on-one and say something like, “As long as you’re working here, I need you to get along with colleagues and treat people politely and professionally. That’s as much a part of your job as any work I assign you. That means that it’s not okay to yell at people, berate or insult them, or otherwise create an unpleasant environment for others here.”

Based on what you’ve written about this guy, that’s not going to be enough to stop it, so I’d assume that you’ll also end up needing a second, more serious meeting. In that meeting, you’ll need to say, “We talked previously about the need to treat people here politely and respectfully, but the problems we’ve discussed have continued. I need to be clear with you that these are serious concerns, and if this continues, it could jeopardize your job here.”

And since you know that he wants a promotion and feels slighted that he’s been passed over, you could also add: “I know you’ve mentioned in the past that you’d like to be promoted. I want to be transparent with you that that can’t be on the table while this continues to be an issue.” But really, the situation is at the point where it’s more important to warn him that he could be fired than to get into why he’s not being promoted.

And you truly do need to be willing to fire him over this if he continues after you clearly tell him to stop. If that seems harsh, consider that this is 100 percent in Tim’s control to stop. This isn’t a situation where he’s trying really hard to excel at his job and just doesn’t have the skills to make it work. This is just Tim choosing to be a jerk. He can stop being a jerk and save his job if he wants; that’s fully within his control. But if he chooses not to, you need to use your authority to say “nope, that’s not how we operate on this team.” Otherwise, you’re abdicating one of your core responsibilities as a manager.

Speaking of which, do you have any sense of why his past managers haven’t addressed the problems with his behavior head-on? What you’re describing is something that people do and should get fired for in healthy organizations, and so I’m curious about why that hasn’t happened yet here. Is your company so averse to firing people that they let toxic employees stay around for years? Or were his previous managers particularly wimpy? Or new managers themselves, and therefore maybe hesitant to take this on?

Figuring out the reason this has been allowed to go on for so long will help you figure out your own next steps. If you’re working in a company that resists letting people go even in the face of really disruptive behavior, this is going to be a harder battle — because you really need the option of firing Tim (or imposing other consequences) in order for him to take you seriously when you tell him his behavior isn’t okay. Otherwise your conversation with him won’t have any teeth behind it.

If you’re working somewhere like that, you should start laying the groundwork now for dealing with it: Talk to HR and/or your own boss, explain the toxic behavior you’re seeing, that you’re going to lay out clear expectations of behavior for Tim, and that you want to be prepared in case that doesn’t solve the problem. Find out what the company will require from you if Tim ignores your warning, and do what you can to get that process moving now if it sounds like a lengthy one. Usually that will mean documenting the problems and your conversations about it, and it may mean using a formal improvement process with him before your company will let you impose real consequences.

And actually, getting your ducks in a row like this is smart to do even if you’re not working at a firing-averse company. Your boss should be in the loop about what’s going on, so that you don’t blindside her in a couple of months by announcing that you need to fire Tim, when you’ve never raised the issues with her before. Especially as a new manager, when you have a serious performance issue on your team (and this qualifies, believe me), you need to fill your boss in about what’s going on and what your plan is for handling it.

I know you said that you don’t feel comfortable talking to your boss about the situation because you’re worried that your level of frustration will make you sound unprofessional — but that kind of frustration often comes from feeling powerless in a situation, and this whole plan is about putting you back in control. When you realize that you have the authority to say “no, this isn’t okay, and as your manager I’m requiring you to stop” and that you have the tools to back that up with action, it’s usually much easier to stay calm.

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Ask a Boss: I’m Going to Be My Frenemy’s Boss!