Dear Boss,
I’m on a team that is still working remotely due to COVID. I mention the remote aspect because this problem didn’t come up in person. Often — probably one to three times in a typical week — I’ll find myself in the following situation: I finish a stage in a project and need my boss’s feedback before I can progress. I send him a message asking him to check in and get a notification that he’s seen the message, but he doesn’t answer. We also have a weekly one-on-one meeting that has been in place for over a year, but sometimes he’ll even miss that, with no notification and no response if I send a message about it.
It’s even worse when it happens near a deadline: We agree to check in before the end of the day in order to get the project sent out that same evening, I finish up and ask for that check-in, and I (a) get no response and so the project goes out late, (b) send the project out on time but unchecked, or (c) get a response saying “now works” later in the evening after I’ve already left my desk for the day (though working from home means I almost always respond when this happens).
On the one hand, it seems like it’s his responsibility to make sure I have work to do, and if he doesn’t want to make use of my time, then okay. On the other hand, I get kind of annoyed! It’s stressful sitting around wondering what I should be doing or unilaterally deciding to send the project out late or unreviewed. I get antsy twiddling my thumbs and not having any work to log for that time.
I’m not sure if this is a problem with me or him or both of us. Does he need to communicate better and manage more actively, or do I need to be managed less? If the latter, how do I improve my independence? If the former, how do I go about asking him for more reliable communication? How can I fill the hours in a way that’s not soul-sucking busywork? Do I owe him after-hours responsiveness when he doesn’t respond to messages during the day?
For additional context, I’m pretty young and inexperienced and really want to do good work and make a career in this industry. Overall, I love my job and working for and with my boss. He’s never mentioned anything, good or bad, about any of this — whether or not I choose to send out projects, how I communicate with him about scheduling, the amount of his time I take up, etc. I’ve been proceeding on the assumption that if he wants me to do something different, he needs to tell me. But I’ve also been binge-reading your work lately, so thought I’d ask.
You can and should talk to your boss about this. He might have no idea that it’s causing you stress, and a simple conversation could solve a lot of it.
But first, on the question of who’s behind the problem: I suspect you’re each contributing to it in different ways. On your boss’s side, he’s ignoring previously agreed-upon timelines, so work is going out late and he’s leaving you stuck stressing about whether there’s something more you should be doing to move projects along. He’s also missing meetings without warning and not responding when you follow up with him, and he’s assuming you’re willing to meet after hours without having ever asked if you mind. These are all his problems.
On your side, you’re being pretty passive. It doesn’t sound like you’ve called his attention to the pattern and inquired about other ways to handle it or asked what to do when a project is in danger of being late. You’re leaning a little too hard on “Well if he wants to pay me to sit around doing nothing, that’s his call.” That’s not to blame you, though — since you’re early in your career, it’s understandable you’re deferring to how your boss wants to do things without raising its impact on you and on the work. In fact, from what I’ve seen, most people early in their careers would respond the way you have, with a combination of frustration and resignation.
But there’s a better way to handle it, and learning it now will set you up well for working with future bosses too.
The thing to know is most managers will assume the way they operate is working fine unless you speak up and explain that it’s not. Partly that’s because managers usually have a lot of other things they’re responsible for, and their attention may be stretched thin. But it’s also not totally unreasonable for your boss to expect that if something is going wrong with projects you’re responsible for, you’ll say so. That doesn’t absolve him of responsibility here, but it does mean there’s room to take action on your side.
So talk to your boss! Explain that because you have trouble reaching him during the workday, projects are going out late or you’re finalizing them without his sign-off, and ask how you should be handling that. Ask if you should try to reach him in a different way (for example, if you typically email, maybe it’s better to call or text) or if you should be more persistent. And ask whether you can move certain types of work forward without his sign-off if he’s unreachable or whether it’s better to miss deadlines in those cases. You might hear that there are different things you should be doing. Or just raising these questions might cue him to realize he needs to do things differently on his side.
You should also mention that once you reach a point where you need his input before you can move forward, you’re often left with nothing to do until he gets back to you, and ask if there are longer-term projects you can work on during those times. Maybe there aren’t, but if he doesn’t even realize this is happening, filling him in might spark a good discussion about ways to better use that time. For example, if he doles out projects to you one at a time, is it possible for him to give you more assignments at once so you always have something else you can turn to while you’re waiting on him?
As for the impromptu after-hours meetings, you can either address those explicitly in this same conversation or handle them separately. If you want to address them directly, you could say, “We often end up talking after hours, but that’s hard for me to accommodate. I don’t mind doing it in an emergency, but can we aim to talk during the workday instead?” Alternately, you can just not be available when those “How about right now?” messages arrive in the evening. I know you’re responding because you are available, but by doing that you’re training him to see those times as working hours for you. Instead, respond the next morning with “Just saw this, had already logged off when you sent it last night” and suggest a better time (or just call him). You might hesitate to do that because it means delaying your work further, but if you don’t, those after-hours calls will never stop. It’s worth accepting some short-term discomfort in order to reset the norms of when you’re available.
If none of this solves the problem, you may have to resign yourself to this just being how your boss works — but it’s very much possible that a straightforward, collaborative conversation will resolve some or all of these issues.
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