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I sometimes have trouble knowing when to ask a question. In the past I had been told I asked too many questions so now I make an effort to ask fewer. This basically means I try harder to find the answer by myself (usually by trying things out or reading documentation) before asking someone else. I think the problem was, when I didn't understand an explanation I didn't say anything, and when I asked again my manager got upset. So now I learned it's really important to get things right the first time around.

At another job my boss would come up to me and ask what I was doing, and I guess I phrased the reply in such away that sounded like I was stuck (though in a sense, isn't that all work is, is a series of getting stuck and unstuck?)

For example I would say "I'm trying to install the latest version of python" and he would say "what's the holdup" and I would say "I'm getting an error message" and he would say "why didn't you ask me?"

Well I could try google searching to find the solution.

This happened on several occasions so I finally asked "how long do you want me to work on something before asking you?", I think he said 10 minutes but latter at a meeting, he told his manager I asked how long I should wait until I ask him a question and said he didn't know how to reply. His manager said "as long as you think you're getting somewhere, don't ask, but as soon as you have no idea what to do next, don't waste any time and ask right away".

Admittedly, the boss was a bit of a nut case and that's why I quit. But how do you know when to ask a question as opposed to try to find the answer yourself? I would say part of it is how busy the other person is you're going to ask.

marked as duplicate by Masked Man, Chris E, gnat, Xavier J, mcknz Jan 3 '17 at 19:02

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    His manager got it spot on, "as long as you think you're getting somewhere, don't ask, but as soon as you have no idea what to do next, don't waste any time and ask right away" – Draken Jan 3 '17 at 6:37
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This is totally a 'level of responsibility' question.

There's a few different types of questions in a work environment:

  1. I'm doing a task & I need help with it.
  2. I need a tool for my task
  3. I have an overarching question about my role
  4. I have an overarching question about the business (policy, law, or other outward facing concern)

If the thing that you're doing has anything to do with 2, 3 or 4; then go to the manager straight away and tell them what you're doing, and ask if they would like to take over or have anything to say about the task before you begin. After that you can go to them with any question, because these tasks fall outside the scope of your direct area of responsibility and fall significantly more into your managers area of responsibility.

If your task is a "I'm doing a task & I need help with it." then it's a judgement call as to when you should ask a question, and how long you should wait. If you're using the time as an opportunity to learn, you can leave the question longer before asking if and only if you're not going to fall behind on your work (within reason).

The Python example that you gave is really a type 2 question. I can understand your manager being a bit taken aback when you told him you were installing a new version of Python, because it's an unusual thing to need to do. While you probably could have got the install going without anyone's help, it's just the 'kind' of thing that would cause your manager some surprise, and I would again put this down to it being 'outside your area of responsibility' even though doing the install and so forth would have just 'been part of the task'. So sometimes it's harder to judge when you should ask. This can still be true of something that your manager would think is under your level of responsibility (or level of pay) such as emptying the kitchen Dish washer.

So rule of thumb, think about how 'suited' what you're doing is to your level of responsibility. If it's more than 25% over, or 50% under, go ask.

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