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‘My Best Friend at Work Is Bad at Her Job!’

Photo: The Cut

Dear Boss,

I started working as an executive assistant at a company I love last summer, and a couple of months later, another executive assistant — we can call her Tracy — started too. We are the only two executive assistants at the company, and a lot of our work overlaps; although we assist different executives, the teams reporting to them work together a lot. I’m a career administrative support worker, whereas Tracy has more experience in human services/social work. I’m much more organized and detail-oriented, whereas she has great empathy and interpersonal instincts.

On Tracy’s first day, we mutually clocked each other as queer and discovered within a week that we share a lot of the same values. We quickly developed a strong rapport and consider ourselves “work besties” now; we regularly eat lunch together and have made plans to hang out after work.

But Tracy’s performance isn’t up to par with mine, and it’s becoming a problem.

I got up to speed very quickly when I started the job, and by the time she arrived at the company, I was well established and able to help her out a lot. Because of our friendship, she’s been open with me about how the kind of work we do doesn’t come as naturally to her as it does to me. I instinctively picked up the slack so that we’d excel together as a team but … I can’t continue to be responsible for her!

During Tracy’s onboarding period, I said great things about her to our shared supervisor, Kathy, and to the executives Tracy works under. As time went on and she didn’t learn as quickly as people expected her to, or as quickly as I did, I’ve felt less like I can put myself on the line for her. But I’m not sure how to pull back without hurting Tracy’s feelings. Especially since we so enthusiastically bonded as friends at the beginning.

I already let our supervisor Kathy know that I’m invested in Tracy’s success, but that I’m having a hard time deciding where to draw the boundary between the two of us working as a team versus doing things on our own. After our conversation, Kathy told me that she needs to depend on me less often and learn how to catch and correct mistakes on her own. Kathy said she’s keeping an eye on the situation and to let her know if I notice any more issues.

I just don’t know how to navigate the nuances of our shared responsibilities, let alone how to decide when I should/shouldn’t help with Tracy’s work. And I’m particularly concerned that Tracy might lose her job. On one hand, having a counterpart with whom I’m so comfortable and compatible is definitely an asset, and I care about her well-being. On the other, it isn’t fair for me to take so much on.

Professionally speaking, I need to put my own oxygen mask on first! Personally speaking, I’m not sure if I should also pull back from our friendship. How should I approach this?

Work friendships can be really tricky in ways people don’t always anticipate. Of course, friendships outside of work aren’t always straightforward either, but work friendships are especially primed for getting tangled up in conflicting loyalties and obligations.

It makes perfect sense that as a friend, your first instinct is to help Tracy. That’s you being a good friend — and you also have an incentive to ensure she sticks around because you like her. But you’re right that you have a professional obligation to limit the amount of help you provide her with — both because that help comes at the expense of you focusing on your own work, and because your manager has explicitly said you need to pull back.

I’m going to argue that it’s actually better for Tracy, too, if you don’t support her so much. That might sound counterintuitive, but if the reality is that this job isn’t right for Tracy, it’s better for her to figure that out now so that she can find a different role or company where she’ll thrive. It’s draining to have a job that you’re not good at, and in the long-term that will likely harm her reputation and confidence — so if she really can’t succeed in this role, it’s so much better for her to figure that out early on (and before she has a long stretch of mediocre work on her résumé).

Plus, even if you were able to continue supporting her at the level you have been — which you probably can’t, now that your manager is involved — what’s going to happen if you leave your job at some point? Or even just take a long vacation or get really busy with your own work? You don’t want to inadvertently set Tracy up for a situation where she’s heavily reliant on you, because you won’t always be there. You might be doing her a favor in the short-term by helping now, but it’s really not great for her in the long-term.

But how do you pull back without seeming callous or weirdly chilly, or without having a jarring transition where one day you’re fully available to her and the next day she’s totally on her own?

If you didn’t have a close personal relationship with her, one option would be to just explain that you’re getting busier and won’t be able to continue helping out with ___ (insert examples of things she’ll now need to do on her own). It’s reasonable to set boundaries like that with colleagues, especially with someone who’s newer than you — someone you were willing to train at first, but now they need to operate more fully on their own. So it’s fine to just say, “I’m swamped with X this week — sorry I can’t help!”

But given your bond with Tracy, I think you’ll both feel better about the situation if you’re more up-front with her. You could say something like, “I know Kathy said she wants you to depend on me less and catch and fix mistakes on your own. I want to be up-front with you that she shared that with me too, so I’m going to pull back and try to be better about not jumping in to help.”

And then you could add: “I feel weird about this. You’re my friend and you’ve been open with me that the work isn’t coming as naturally to you as you’d want, and my instinct is to help. I’m worried about continuing to do that after Kathy has talked to both of us, though, and I wanted to let you know what I’m thinking so that you have context for me trying to be better about staying in my lane.”

It’s hard to give specific advice on how to navigate your shared responsibilities without knowing the specifics of what those are, but in general, the more you can have a clear division of labor between the two of you — so that you each know, for example, that you’re responsible for requests about X while she handles all requests about Y — the easier it will be. If your system now is more like “one of us jumps in to handle things,” and that someone is usually you, I’d try to nail down something more specific. If the work defies broad categories like that, your system may need to be more fluid but could still mean saying things like “I’m going to have my hands full with X today; could you handle Y and Z if they come up?”

If you notice that Tracy continues struggling, there also might be a bigger conversation to have with her, one where you reflect back to her what you’re seeing — the parts where she’s struggling as well as the strengths she brings to the role — and ask her if she’s happy in the job and sees herself there long-term. Sometimes people get so caught up in thinking they have to make a job work that they lose sight of the fact that there’s no shame in saying, “You know, this job isn’t for me.”

If you’re willing to be that kind of sounding board for Tracy, I don’t think you need to pull back socially. It could be a relief to her to have someone to talk about the situation with someone who knows the nuances of it. That might feel awkward to you — it can feel awkward to be successful when your friend is floundering. But if you’re willing to tolerate that discomfort, it could be a great favor to help her sort through this without sugarcoating it or B.S.-ing her.

Order Alison Green’s book, Ask a Manager: Clueless Colleagues, Lunch-Stealing Bosses, and the Rest of Your Life at Work, here. Got a question for her? Email Her advice column appears here every Tuesday.

‘My Best Friend at Work Is Bad at Her Job!’