When the person in charge is the problem

Got a boss who drops the ball, can’t handle feedback, or makes their inept kid your intern? Here’s how to manage up

As the space between work and not-work becomes ever more blurred, questions about how to do this thing we plug away at for 30 or 40 or 70 hours a week become all the more expansive. In Work Flow we delve into the novel dilemmas created by the new ways we work, as well as timeless questions about ethics, gender assumptions, and toxic work situations (and how to escape them). How we work is an important component of how we live—and we’re here to help you do better at both.

Something messing with your flow? Unload your work problems here, and you’ll not only feel heard but you’ll also get unbiased, real-world advice. (That’s something your work sibling/spouse just can’t offer.) Tell us everything: editorial@wework.com.

My manager is going through a midlife crisis and a divorce, and doesn’t seem to care about anything work-related, which means I have to stay late and get stuff done when he leaves for the bar. What do I do about this? I actually really used to like him. Now I feel like all I do is clean up his messes, and it’s making me so angry.

Remember back in high school when you’d get stuck on a team project with a bunch of slackers and have to do the project yourself if you wanted to get it right, or done at all? It stinks when things are not fair. It stinks to have to accommodate for someone else’s lack of focus, or work ethic, or inability to do the job for whatever reason. It really stinks to confront the reality that we never truly leave high school, that the dramas and traumas and various emotional conundrums and struggles to coexist happily with others continue to follow us wherever we go through a life, even into our workplaces.

But, of course, the circumstances shift. You are an adult, and you actually are in control, as much as any of us can be. Since it sounds like you once had a good relationship with this person, I suggest talking to him directly—but not when you’re furious, and not after he’s been to the bar. Look: He knows that he’s been slacking, that he is going through a whole bunch of stuff, and that he is leaning on you (and maybe others?) heavily as he deals with these major waves in his personal life. Somewhere deep inside, he probably feels guilty and ashamed and sorry for himself, at the same time that he is insistent on this as his course of action, for whatever reason. In a very light defense of the guy, while it’s not cool to drop out at the office and leave all the lifting to your coworkers while you belly up to the bar, it’s also extremely unpleasant to have to go through a divorce. I suspect your manager is utterly tapped out, attempting to deal with a whole bunch of awful things at once, and he’s self-medicating to help him through it. The result is good for no one, especially not a manager who is supposed to, you know, manage. He is not doing his job, and he’s expecting you to do it, and you are entitled to feel exactly how you feel about that. 

But you liked him once, I’m hanging onto that, and I think you should, too. And you would still like the job, too, if it wasn’t like this, I think? So talk to him. Tell him that you know he’s going through a lot. Be discreet, but share how you feel, and listen to what he has to say. Try: “I’m really struggling now, as I feel like the burden of the work has fallen upon me, and I’m staying late day after day to get everything done. This is not tenable for me. Is there a way we can handle this better?” This may not fix anything. He might still blow off work and leave you to clean up his messes, and you might keep getting angry, but it’s your job to advocate for yourself, and staying late and picking up tasks and a whole bunch of associated resentment is no way to live. As your manager, it is this person’s role to deal with exactly these issues. If he doesn’t respond or take the conversation seriously, it’s time to take the quandary up the chain to human resources or your manager’s manager. Beyond that, you might want to start actively looking for a new manager. Because no matter how much you used to like this guy, you can’t live like you’re in high school forever. 

My manager is terrible at taking feedback, but really needs some. HR is useless at my company; I’ve gone to them previously and they’ve never done anything to help. Is there a way to give feedback that doesn’t feel like feedback? How do I note that what she’s doing could go over a lot better with some slight changes, without getting screamed at for trying to “correct” something she’s done?

Ahhh, feedback. No one wants to be told they’re bad at something (do you? I don’t!), and I suspect your manager has some baggage in this arena, which comes out in defensiveness to perceived “corrections.” I’d tread lightly given that—if she’s “screamed” at you in the past, she may not be the best candidate for even the most constructive criticism, not to mention, of course, that she’s your manager. Is there someone between you and HR that might be more amenable to listening to your thoughts, and then funneling your wisdom down the chain?

If not, my best advice is to make your feedback about the situation and not about the person. (Also, pepper it with some positives—don’t just unload a bunch of negatives and expect it to go over well.) Offer to help, or to be a part of a solution that you identify in the conversation: “I love how we’ve been accomplishing X and Y; do you think that might work with Z, too?” “I really admire how you are able to do blah blah blah and blah blah blah. I noticed that BLAH might be getting short shrift. Is there a way I might be able to help out there?” Or even, “Your last presentation was so good. But sometimes it’s hard to hear you in the conference room. Would you ever want to practice and I can test sound levels for you?” It helps to have something of a solution already in your head. Don’t make your comments personal or accusatory; stay calm and direct the conversation in a proactive way toward the resolution you’re looking for. Talk about results and the company’s bottom line are always going to be far more compelling (and harder to argue against) than saying, “Hey, I just don’t like this,” or “It annoys me or makes it hard for me when you do this.” Some experts recommend asking your manager if they’d like feedback before just launching into it. (That might help avoid the negative reaction you’ve been getting, though it’s clearly very much “feedback” then.)

Speaking of which, I’m curious about your past history of going to HR (for what, and what did they do/say?) as well as your fear that your manager will start yelling at you for something she takes as a correction. Because there’s been defensiveness before, before reaching out, I’d deeply consider what feedback you want to give and why—and whether it’s worth it. Is it indeed a “slight change,” or is this really about how the two of you communicate as a whole? Is there something else going on? There’s some soul-searching to be done. If you really find you can’t talk to the manager and your HR is as useless as you say, what about suggesting (even anonymously) that the company implement an anonymous feedback system for all employees, in an effort to bring about a greater understanding of what’s working (and a better bottom line!) across the board? Maybe it’s your HR that needs feedback, to start with. Share this study with them, and take it from there. 

My intern is awful—sheer incompetence levels of awful. He lost some important paperwork, had a reply-all fiasco, and can’t even be trusted to pick up coffee. I’d insist we fire him, but he’s also the boss’s kid. What do I do?

I am so sorry to say this but… you probably need to wait this one out. An intern, generally speaking, is only going to be with you a short time before moving on to some other job/ torturing some other employees, and if your boss played a role in placing their kid as intern, they surely know enough about their kid to know that this was going to be a problem. And yet, parental love can be blind, and no parent wants to hear from their employee that their kid is awful. As luck would have it, the circumstances you describe are quite public: It seems like everyone knows the intern is bad—maybe even his parent? So keep on doing the best job you can, document the intern’s mistakes (just in case they come back to haunt you), and make sure to only assign him duties related to things that can’t be destroyed. Then, count the days until Bad Intern’s time to leave. Share this story with all of your non-work friends, who will hang onto your every word, and eventually sell it all as a screenplay and make bank.

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