Contrary to what you were told as a kid, there is such a thing as a stupid question. We have an unfortunate tradition in corporate America of assuring people that “there’s no such thing as a stupid question.” If someone is failing, often managers will treat that as a training problem, not an ability problem.
But I am here to tell you the plain truth: if you find your manager frequently saying “if you’re not sure, then please just ask me, I’d rather that than you…” you should take that at face value but should also (unless you’re new, which is a special case) be very concerned about your career and take a deep look. What’s he’s really saying is “I would rather you take up my precious time with stupid questions than leave behind messes that cost me even more time because I can’t trust you not to screw up. God, I can’t wait to lay you off.”
Why is that? Why is it that managers will sometimes tell you to ask questions when what they really want to do is fire you? Well, for one, it’s difficult to fire people in America (though not nearly as difficult as in Europe). It’s also emotionally uncomfortable to have a direct conversation with someone so new managers will try to avoid it by just taking over control of what you’re doing.
That’s really what managers are doing when they say “just ask me.” They’re taking over your job–the job you should be doing on your own. They’re not happy about it and you’re not happy about it.
So how do you claw your way back into their trust? Unfortunately, this falls into that soft skills category that’s difficult to make a list of rules for. But here are a few guidelines for spotting situations where you should say “wait a minute, am I screwing up here?”
1) You’re asking a question you’ve already been given the answer to before
2) You’re asking a question you could answer yourself if only you did some cursory research (Google is your friend!)
3) You’re asking a question that doesn’t make sense given the context (why are you asking about the Christmas party during a release planning meeting?)
4) You’re asking a question that you already know the answer to and really you’re just asking it to show how smart you are
5) People are having a hard time understanding what you mean, and have to ask other people to interpret what you’re saying
6) You’re having a hard time understanding other people, but nobody else in the room seems to be having the same difficulty
7) Projects and tasks you’re assigned to tend to be late/fail/have issues for no concrete, identifiable reason. “Stuff just happens” to you and you can’t put your finger on why
8 ) Projects and tasks you’re assigned to tend to be late/fail/have issues for concrete reasons, but with a higher frequency than everyone else on the team.
9) People avoid talking to you because they think the conversation will suck too much time out of their day
There is an exception to this rule: if you’re new. If you’re new you should ask as many questions as you can. Stupid ones, irrelevant ones, smart ones, you name it. Get them all out there right now because that honeymoon period is ticking away…