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‘My Boss Won’t Give Me Any Direction’

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Frequently, my manager will assign me a project and not give me very much instruction. When I ask questions, she tends to get frustrated and tells me to just figure it out. So I do my best! But when I come back later on with the work mostly or completely finished, she’ll tell me that I didn’t do it the way she wanted me to and admit that she should have given me more instructions.

For example, I was recently working on a project somewhat outside of my experience, and  I asked her some questions about what to do. She told me she was hoping that I would take ownership of the work and that she didn’t want to do it herself. I tried to explain that I was just asking for guidance on where to start and not for her to take it over. She seemed to kind of understand and she said she’d send me some suggestions later. She never did, so I just started working on it anyway. 

Today we met about the project, and it was the same thing. She noted that what I’d done so far partially worked but was missing a crucial piece, and even said again that she should have given me that context earlier.

These interactions leave me feeling like I am constantly failing at my job, but am I off base to feel like she is setting me up for failure? Is there any way to get out of what feels like a never-ending cycle?

You’re not off base. Your manager is bad at delegating.

When she assigns you projects, she clearly has an idea of what she wants (or doesn’t want), because when you complete the work and show it to her, she’s able to identify that it’s not what she had envisioned. But she’s not putting in the effort up front to articulate the expectations she has in her head so that you’re on the same page from the beginning. That leaves you stuck guessing about what performing successfully might look like, and then frustrates you both when your guess turns out to be wrong.

What’s even more maddening is that she seems to realize it! She keeps telling you at the end of this cycle that she should have given you more guidance earlier, but then doesn’t apply that realization to the next project.

I suspect that, like a lot of managers, she wants you to read her mind. She wouldn’t say it that way, of course, and I’m sure she doesn’t think of it that way. But if she’s telling you she wants you to take ownership for something but isn’t willing to talk through how she envisions that thing when it’s done well, and that she can communicate in shorthand without much detail … well, mind reading is the only way that would work.

To be fair, it is true that at a certain level of seniority, it becomes more reasonable for a manager to expect you to figure out the details and to know what doing a particular project well looks like. But even then, if that’s clearly not happening, a good manager knows she needs to invest the time to get more aligned on those things — not just keep going through this cycle over and over.

In any case, since we know your manager isn’t good at expressing the expectations and assumptions she has in her head when she assigns you work, what can you do on your side?

First, it’s worth talking with her and naming the issue explicitly. You might figure she’s already aware of the problem — after all, she’s in these frustrating conversations with you — but there’s a decent chance she hasn’t stopped to pinpoint exactly where things are breaking down or thought about how to fix it. You could raise it by saying something like this: “I’m finding that often I’ll understand an assignment one way, but discover when I turn it in that you had different expectations — and sometimes we both acknowledge that it would have helped to have talked in more detail earlier on. Could we try taking more time to discuss what you’re envisioning before I start working on something? I think it would save us both time later on!”

If your boss responds by again saying she wants you to take ownership, you can say, “I want to take ownership for my projects, and to do that with confidence, I want to be sure I understand what you’re envisioning. Right now I’m often just guessing, and sometimes we’re picturing different things. If we can take a few extra minutes to make sure we’re on the same page, it’ll be much easier to take ownership from there.”

Of course, the real thing you’re going to have to take ownership for is probably drawing those details out of your boss with each new assignment. When she assigns new work to you, don’t be afraid to proactively ask questions, including things like:
- “To make sure we’re on the same page, what I’m picturing is X. Does that sound right to you?”
- “So what I’m taking away is that doing this well would mean (fill in details). Does that sound right?”
- “Is there anything similar we’ve done in the past that would be a good model to look at?”
- “Are there specific ways you’d like this to be different from X or Y?”

Then, once you get started on the work, consider sending your boss an early “slice” of it to weigh in on (like the template you’ve created to track data or a key segment from a document you’re writing). Giving her a chance to provide input early on can end up saving you a lot of time on the rest of the work — especially since it sounds like she finds it easier to react to something concrete rather than thinking it through in the abstract.

Even doing all that, though, there will still likely be times when you turn in a piece of work and hear it’s not what your boss wanted. That happens even with managers who delegate well. That doesn’t necessarily mean you failed; sometimes it takes several rounds of back-and-forth to figure out exactly what something should be. If you’re not sure if that’s the case, you can always say to your boss, “Did I misunderstand your instructions? If there’s a way I could have avoided getting it wrong, I want to make sure I have that info for next time.”

That can be useful to ask because it’s possible that you’re more frustrated over these redos than your boss is. Who knows, what you see as failure after failure she might see as a necessary part of the process.

If you do all this, it should make your boss more aware of her own role in this cycle and help you both bring her expectations to the surface earlier on. But if she bristles at your attempts to draw details out of her at the start of projects and just huffs some more about ownership, then you don’t just have a boss who’s bad at delegating. In that case, you have a boss who’s bad at managing in more fundamental ways, and that’s much harder to change (impossible most of the time, really). But even just getting clarity on that — and knowing that it’s her, not you — can make working with her more bearable.

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.

‘My Boss Won’t Give Me Any Direction’