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Advice / Succeeding at Work / Management

The 2 Questions You Need to Ask Yourself if Your Boss Keeps Making Your Job Harder

You rearranged everything and have devoted the last week to a new, important project. Which would be fine if your boss hadn’t just informed you that it’s being scrapped and there’s no need to work on it anymore.

It’s frustrating, it’s annoying, and it’s definitely vent-worthy, but it happens. However, if it’s happening a lot, then you might start to think your boss is purposefully getting in your way.

But can that really be the case? Is your boss really an evil troll who’s there simply to stop you from getting your work done? Or, is it possible she’s just trying to do her job and manage you?

Whenever people are working through this, two complaints consistently come up—“My boss assigns me pointless work” and “My boss doesn’t care about my professional growth.” So, in honor of those two issues, here are the two questions to ask yourself before coming to your big conclusion.


1. Is There a Reason My Boss Assigns Me Extra Work?

I had a friend who had an actual boss from you-know-where. He’d ask her to research the three best ways to launch a new project, and after she’d spent all week on it, mention that he didn’t have use for that project anymore. He’d drop work on her desk whenever he felt like it and ask her to have it completed by start of work the next day, compelling her to spend all hours of the night at the office. Then, she’d find out later that work wasn’t really that urgent.

Need I say it? None of these assignments helped her do her job. They only reflected that her boss was on a power trip—one that inevitably motivated her to leave a role at an impressive company much earlier than she might have otherwise.

Now, let’s assume that your supervisor isn’t that extreme. What does she do? She asks you to tackle other duties as assigned, because your organization is lean and so everyone takes on more grunt work than they’d like. Or maybe, she asks you to do something way below your pay grade, but includes an explanation that the intern called out sick, she’s in a serious bind, and your help would be very helpful.

Yes, the result is still mornings and afternoons and sometimes whole, entire days where you have to backburner your real work. But if your actions still benefit your team, department, or overall goals; your boss is just doing his or her job.


2. Is My Boss Encouraging Me to Grow and Develop My Skills?

Everyone wants to innovate; everyone wants to disrupt; everyone wants to change the status quo and make things better. And sometimes a new approach is more efficient, more profitable, or shinier. But other times, it doesn’t make sense. It’s too expensive. It’s a time suck. It’s fixing something that’s not broken.

And it’s your boss’ job to know the difference.

So, while it stings just the same when your manager shoots down your suggestion, remember that not all “nos” are created equal. If he always says no, or if he always says he’s too busy—and never finds time to hear you out—your boss is getting in your way. That also goes for a manager who doesn’t offer you any opportunities for growth. He never mentions professional development opportunities, he won’t let you take time off to attend a conference, and he has no suggestions for how you can grow in your role.

But if she encourages you to think creatively and take on new, interesting projects (elsewhere), she’s helping you focus your energy on what matters most. Yes, you’d like her to come right out and say, “While this is genius, we don’t have the money/the client is a pain/it just doesn’t align with our overall goals.” Unfortunately, that’s not always possible (or realistic). So, look for whether your manager encourages you to keep sharing your ideas and learning new things. If she asks how you’d tackle a situation or what approach you’d suggest in other areas, it’s probably just this matter.



You hate it when your boss gets in your way—and she probably hates it, too. But before you decide she’s a terrible manager, consider if she’s just doing her job. However, if you answered “no” to both the questions above, things are not on a good path. Start by asking to set up a meeting to discuss your workload and responsibility. If your boss won’t make the time, or if she keeps repeating the behaviors above, you should probably start looking for a new job where your manager will let you shine.