ask a boss

‘Should I Tell My Boss Everyone’s Mad at Her?’

Photo: The Cut

Dear Boss,

I started working at my current job about eight months ago. My team is small — it’s just me and my boss, who’s the director — and we have many projects that require us to work with other teams within the company. Most of the time, we’re asking people from other teams to take time out of their daily workload to assist us. Asking people to jump in on projects is not always easy, especially when it feels like everyone is bogged down with a tremendous workload. I consistently try to be a bit lighter in my approach when asking for assistance — my manager, however, sees no problem essentially bullying her way into a quicker response.

Right after starting the job, I noticed many people spoke warily of my manager, who we’ll call Jane. I could definitely understand their issues — she can be quite abrasive and overpowering. She is very negative and constantly micromanages just about every project she’s on. Regardless of those qualities, I’ve still been able to gel with her. Sure, sometimes she pries too far into my personal life or snaps at me for little to no reason, but I’m able to compartmentalize, and I’m happy with my position. Outside of the difficult parts of her personality, I don’t necessarily mind working with her. 

We’re in the midst of a large project at the moment and need quite a bit of IT assistance. The only person who can help out is currently on a business trip across the country. He’ll be back within a day or so and reminded Jane about his absence several times before he left. Today, Jane asked me to call this man multiple times and ask him vague questions that she had already emailed to him. Unfortunately, because she’s my direct boss and I can’t really say no, I had to make the call and apologized profusely to this man. He was understanding with me, but proceeded to tell me to tell my boss to “go F herself” and let her know “the world doesn’t revolve around her work.”  

I wish I could say this is an isolated incident, but Jane has asked me to do things like this before, like abruptly calling people to demand something that could wait until they’re able to email her back. I’ve told Jane that people get frustrated by this, but I’ve watered it down significantly. I haven’t shared how angry people get, mostly because I’m worried she’ll throw a fit, or even worse, confront them, which could damage my relationships with those co-workers.

Whenever I express discomfort with the way she asks me to approach people again and again, she says I’m just “being shy.” I’ve told her multiple times that I’m not shy, but what I haven’t said is that I don’t enjoy harassing my co-workers. 

How do I confront her without making it seem like a personal attack? I want to discuss this in a healthy way, but every time I try to talk about it, she doesn’t seem to take anything in — she’s just immediately on the defensive.

Jane sounds like she’s the type of person who sends an email and then pops at your desk a minute later, saying, “Did you see my email?” And there is a reason those people are considered universally aggravating.

My hunch is that Jane is so used to her way of operating — micromanaging, following up too soon and too often, and not considering that people have priorities that might be different than her own — that she’s truly oblivious to how she’s coming across. Or, to the extent that she’s aware she’s irritating people, she probably thinks they’re in the wrong. I know I’ve had times when I’m so caught up in whatever I’m doing that it’s easy to forget that my project isn’t as urgent to other people and that they might rightly need to prioritize other things before turning to my thing. We’ve all probably had those moments! Jane’s problem is that it’s her default way of operating.

I get why you’ve downplayed how angry this is making people, especially since Jane seems like the type to shoot the messenger. But if you truly want to address this, you’ve got to be more upfront with her about what’s going on. Watering it down means she’s not experiencing the true consequences of what she’s doing — you’re absorbing those yourself so she doesn’t have to.

I hear you that you’re worried it could damage your relationships with people if you tell Jane how angry they are and then she goes and confronts them. One way to address that is to ask their permission first. The next time someone expresses anger to you about Jane’s demands, you could say, “Do you mind if I share with Jane how frustrated you are? I think it could be useful for her to hear that.”

But even if you don’t do that, in most cases it should be okay for you to pass along the gist of people’s reactions to Jane. Of course, if someone is obviously saying something for your ears only, that’s different — but if your sense is that they do intend for their push-back to reach her, let it reach her. It’s possible that hearing how frustrated people are will nudge her into pulling back on some of these requests. But if you’re not being fully upfront with her about that, there’s no real impetus for her to change anything.

Try sharing people’s unvarnished reactions with her three or four times before you address the issue more broadly with her. It’s going to be harder for her to write you off as “just shy” when she’s already heard a few of these unfiltered reactions. Even then, though, I’m not convinced that addressing the issue with her in a general way is to going to get you the results you want, given what you’ve said about her defensiveness — and you might have more success pushing back on individual instances as they come up.

But if you do want to try the big-picture conversation, you could try saying this: “I’ve been getting the strong sense that people are really frustrated when we call them about questions we’ve already emailed them, or when we push them to respond immediately without accounting for other priorities they have on their plates, and I worry it’s damaging our relationships. For example, I know Bob and Lucy are really good about responding to emails, but they’re also swamped with other things, so it won’t always be immediate. I’d like to experiment with giving people more time to get back to us — I think we’ll still get what we need in plenty of time, and I think people will stop being so aggravated.” (Note the “we” language — that’s intentional. You’re framing it as being on her side, which might help.)

The other option is to skip that conversation entirely and just push back on individual instances. The next time Jane tells you to call someone when you think it’s going to annoy that person, you could say, “You know, he just got the email yesterday — I think it’s going to be aggravating if I follow up this quickly. How about I make a note to call him on Friday if hasn’t responded by then?” Or: “He’s been really irritated when I’ve followed up this quickly in the past. He’s generally really good about responding once he’s back in town, which will be in two days. I can make a note to check back if we haven’t heard anything by the end of the week.”

If none of that works … well, it’s probably not something that rises to the level of going over her head; that’s an option to reserve for bigger issues (or to let her annoyed recipients raise themselves), although you can certainly mention it if Jane’s boss ever solicits feedback from you.

But there is one other thing you can do, which is to be really direct with people when you contact them on Jane’s behalf. You shouldn’t openly throw your boss under the bus, but it’s okay to say something like, “I’m so sorry to bother you with this and I know you’re swamped, but Jane asked me to check with you about X” … and then if someone gets angry, “I completely understand why you’re frustrated, and I’ll let Jane know that as well.” If you’re being clear that you’re not the one initiating these calls, and if you’re understanding about it when people react badly, they’re pretty likely to put the blame where it belongs.

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.

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