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‘My Boss Demands Unrealistic Timelines When Assigning Me Work’

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

Dear Boss,

My manager regularly hands me projects that have unreasonable deadlines. I’ve tried to push back or offer alternatives, but the conversations usually go like this:

Manager: “We need to do an updated training for the Blue team. Can you do an overhaul of the materials and present it?”

Me: “Sure. It will take me some time, but I can do that. When does it need to be ready?”

Manager: “Great! We have the meeting set up for the end of next week.”

Me: “Wow. That’s an aggressive timetable because I’ll need to do X, Y, and Z to get it created. Plus I have meetings 1–4 p.m. every day this week and all the other things I’m working on. Can we push the date out?”

Manager: “No. Super Big Boss wants it then. You can table the other things and just do this next week.”

Me: “I don’t think that’s enough time. You know how things always come up that we’re not planning for.”

Manager: “I’ll make sure that doesn’t happen. You’ll be fine. I know you can do it!”

Me: “Could we do it in stages? Maybe X next week and then Y could be the following week to give me more time? I can get the smaller part done next week for sure.”

Manager: “Nope. It has to be everything. We have the whole team scheduled to start the project that following week, and they already have bookings. You’re so good that I know you’ll be able to get it done.”

And she’s right, I have done it (several times) and done it well. But I HATE it, and the time frames are getting shorter and shorter. It’s to the point that my work is no longer great and/or it’s incomplete. And sometimes I’m not the one delivering the final product, so my unfinished part is impacting other people. When it is me responsible for the delivery, I’m frequently going into situations wholly unprepared. Even when it is something I can pull off, I lose sleep stressing about it getting done and end up working overtime (I log my hours, so my boss knows I clocked back in from 7–10 p.m. multiple days in a week).

She knows I don’t like doing it, but I think I need to be more firm about communicating my obstacles. Or maybe I need to say no? We’re a small team, so I know my only other co-worker will get stuck with it. Or just spectacularly fail once? As much as I hate that idea, I think my reputation could weather the hit as long as it’s something fairly low-stakes. 

How do I say to her, “There’s no way that can happen in the time frame you’ve given,” in a way she’ll understand?

Yeah, you’re giving her a soft no, expecting her to respect it, and she’s barreling right through it.

It makes sense that you’ve tried approaching it that way. Most of us aren’t socialized to say to our bosses, “No, I will not do that” or “No, that cannot be done.” We’re trained from the time we start working to look for ways to say yes or — when that’s impossible — to use softer pushback and expect our bosses to pick up on it. And good bosses do.

The problem is that your boss is ignoring what you’re saying. She hears your concerns and doesn’t care, and at this point she’s learned from experience that if she pushes you, you’ll find a way to get it done. Maybe it won’t be perfect, but you’ll get it finished. If she cares about “done” more than she cares about “perfect,” this is working out well for her! She runs roughshod over your objections, you feel you have no choice but to give in, and she gets what she wants.

And for the record, it’s possible that the work doesn’t need to be perfect. It’s possible that the work you consider shoddy is actually good enough for what the situation demands. Sometimes speed is more important than quality, and maybe when she’s telling you to rush through it, she’s saying she’s fine with cutting corners. It’s worth talking that through with her, because you might have different ideas about how much effort is required.

But assuming that’s not the case, or if it is the case but it still doesn’t solve the time crunch, you’ll need to take a firmer approach when your boss comes to you with an unrealistic deadline. Right now you’re asking, “Could we change the deadline?” and when she says no, you give in. What if you instead moved to a firmer “it’s not possible” framework? After all, right now what makes it possible is your willingness to lose sleep and work lots of extra hours. What if you took those things off the table? Then the conversation might sound more like this:

Manager: “We need to do an updated training for the Blue team. Can you do an overhaul of the materials and present it?”

Me: “Sure. The earliest I could get it done would be three weeks from now, because I’ll need to do X, Y, and Z to get it created. That would also mean putting projects 1 and 2 on hold until next month.” 


Manager: “No, Super Big Boss wants it sooner.”


Me: “It’s a matter of X hours of work total, so it’s not possible for it to be ready next week. If it has to be ready by then, we’d need to bring in someone else to do a lot of it.”

Manager: “You’ll be fine. I know you can do it!”

Me: “No, there’s no way to do that. In the past when they’ve given us deadlines like this, I’ve made it work by logging extra hours and losing sleep, and that’s not something I am able to do again.”

To do this, it might help to imagine the tone and wording you’d use if she were proposing something that was truly and obviously impossible — even if you worked 24/7, it still wouldn’t get done. To use an intentionally extreme example, if she said you needed to be 3,000 miles away one hour from now, you’d hold firm on saying it couldn’t happen, right? You need the same mental framework here. You’re not willing to sacrifice your nights and your mental health anymore, so some things are simply not possible.

It also makes sense to talk with your boss about the pattern before another one of these assignments happens. Sit down with her and say, “Recently you’ve been giving me rush projects with deadlines that are really difficult to meet, like X and Y. The only way I’ve been able to do it has been by working late every night and not sleeping. For the sake of my health, I’m not able to continue doing that. I want to get aligned with you on what to do when we’re asked to complete things in an unrealistic amount of time.”

You also might talk with your co-worker — the one you’re worried will get stuck with projects you refuse — to let her know you’ll be setting firmer boundaries and encourage her to do the same. If you’re both saying no as a united front, you might have more luck getting through to your boss.

I don’t recommend “just spectacularly failing” in order to make your point unless you absolutely have to, since there’s a lot of risk that you’ll just be blamed for it. But if none of the above works, it might be all that you’re left with. In that case, you should explicitly warn your boss ahead of time — as in, “I need to be clear that I cannot commit to that deadline. I will do my best to get as much done by then as I can, but I do not think the whole thing can be completed then.” And then remind her again as the deadline is approaching — “I know they wanted X by Friday but, like we talked about, it’s not looking likely. I’ve worked on it solidly all week but am only about halfway through and will need at least another week to finish.” By keeping your boss in the loop, she won’t be able to say you’re blindsiding her when you miss the deadline. (And while this is going on, resist the temptation to knock yourself out to finish in time. Work steadily, but work your normal hours and don’t stress about doing more.)

If your boss objects to this approach, then the next step is for the two of you to have a conversation about what the role really requires; if your boss thinks it should require long and sleepless nights, let’s get her to say that out loud so you know what you’re dealing with … but hopefully it won’t come to that.

Find even more career advice from Alison Green on her website, Ask a Manager. Got a question for her? Email Her advice column appears here every other Tuesday.

‘My Boss Demands Unrealistic Timelines When Assigning Work’