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‘This Is My First Job Postgrad. Is My Boss’s Behavior Normal?’

Photo-Illustration: by The Cut; Photos: Getty Images

Dear Boss,

I graduated from college last year and since then I’ve been working at my first full-time job. I am in a client-facing role at a small-ish nonprofit, and mostly I love it.

Lately, though, I’ve been having some issues with my boss, Gillian. She has always been kind, open, and accommodating; in a lot of ways I’m grateful because I’ve heard so many boss horror stories. But she’s flaky, and it’s becoming more and more of an issue. For example, she recently implemented a weekly standing meeting for the two of us, which I was happy about because previously our meetings had been inconsistent. However, she’s usually at least 30-90 minutes late. It becomes hard for me to schedule meetings with clients on afternoons I’m also meeting with her because I know it will inevitably be pushed back. She is always apologetic, but the trend hasn’t changed. This isn’t a huge deal because I know things come up … but also it’s hard to get her to commit to help with anything without a face-to-face discussion.

My primary complaint is that every time I meet with Gillian and ask her to do something, she promises to do it (often by end of day) and almost always forgets. This becomes frustrating to me when it affects my work with clients. For instance, I have to clear any big purchases with Gillian so she can order them. We have no issue communicating about what’s feasible/affordable and what isn’t, and she is generally supportive of the bigger purchases I suggest making for clients. But she promises to purchase things, then doesn’t do it! My role doesn’t have the budget to make the purchases myself, so I can’t just get her permission and do them on my own. I have to wait for her to make the transaction. I’ve learned not to promise things to my clients until I’m holding the items in my hands, but I feel guilty for taking such a long time to get their needs met when it could be done so much faster. 

Gillian tends to respond to about a quarter of my emails during the week — usually the ones that involve outside stakeholders — and is only a little better over text and phone. I don’t think I’m communicating an inappropriate or overwhelming amount — maximum once a day, and only about things she’s previously promised. To her credit, she is generally reachable when something urgent comes up with a client and she has been supportive in those situations. 

None of these things are huge problems on their own, but I feel like they’re building up and together they’re really frustrating. That’s especially true because I am super-organized and committed to meeting my deadlines and I hate to be perceived as unreliable for something that isn’t my fault! 

I feel like I have no idea what’s normal and what isn’t in a postgrad workplace and boss-employee relationship. Is this something I just need to take in stride and continue to work around?

Well, there’s how things should be and then there’s how things actually are. There are indeed plenty of managers who are flaky and unreliable, and their teams do just end up finding ways to work around them — in many cases, getting things done in spite of them, rather than because of them. It shouldn’t be that way — you should be able to rely on your boss to do what she says she’s going to do — but sometimes that’s the reality of it.

That said, I don’t think you’re there yet. Your boss’s flakiness very well could end up being something you just need to adapt to, but it’s too soon to say for sure; there are tactics to try first.

For starters, name the issue to Gillian! You may think she must realize how often she flakes out, but she might not be aware of how frequently it happens or, importantly, how it’s affecting your work. (Or she might have a vague idea in the back of her mind but is avoiding looking at it head-on because so far she hasn’t had to.) The framing to use when talking to her isn’t “You suck and I can’t count on you,” but rather, “Our current systems aren’t working; can we put new ones in place?”

Sit down with Gillian and say something like this: “I wondered if we could talk about a better workflow for making purchases. It’s taking a long time to get items for clients; for example, Client A ended up waiting two months to get X and Client B still doesn’t have Y, even though we promised it to her last summer. I know you’re juggling a lot, so I wondered if it would help if, for example, I send you a weekly reminder of what purchases we’re waiting on, or if there’s some other system we can put in place that would help.” And feel free to include other ideas that could help. For example, would she be willing to give you formal authority to spend up to $X a quarter so you can keep things moving? (I’m focusing on the purchases since that’s the example you gave, but you can adjust this language to include other challenges too.)

It could be that the only fix is for Gillian to get her act together — which isn’t something you can implement on your end — but who knows, there might be improvements to the procedure that would help her do that. Even if there aren’t, you’ll have flagged for her that the way she’s operating is causing problems for your work.

Now, when you raise the subject, you may find that Gillian isn’t as concerned as you are. In nonprofit work in particular, people are often stretched thin and making near-daily trade-offs on priorities. It’s possible Gillian is deliberately de-prioritizing your requests because they’re less important than other work she has on her plate. But even if that’s the case, it will be good to hear it so that you can adjust your expectations and get a better sense of what’s realistic. Either way, it’s a worthwhile conversation.

It’s also smart to ask Gillian if you’re using the best methods to communicate with her. You could say that you’ve noticed she’s not as responsive over email and ask if she prefers you text or call instead, or save up everything that’s not time sensitive for one call or meeting a week, or follow up if she hasn’t responded after two days, or so forth.

Separately, at some point, you should also address the situation with your meetings, which could sound like this: “I know your schedule is really busy and so you often have to push back our meetings. That ends up meaning I either can’t schedule clients on those afternoons or I’m late for them or need to cancel entirely. Is there another day or time that we could plan on more reliably?” Again, ideally this will lead to a solution, but if nothing else, it should nudge her into realizing she’s making things difficult for you. As with the discussion above, you might hear that while she knows it’s not ideal, it’s also unavoidable … but it’s important to bring the issue to the surface all the same.

If you have those conversations and nothing changes, then yes, at that point you’ll know this is simply how your boss operates and then you can move into a mode of figuring out the best ways to work around it. Or you might decide you’re willing to change jobs over it. Although, I will say, this comes up with enough managers that working around it is a useful skill to have.

Find even more career advice from Alison Green on her website, Ask a Manager. Got a question for her? Email askaboss@nymag.com (and read our submission terms here.)

‘This Is My First Job. Is My Boss’s Behavior Normal?’