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In some of my past jobs I had gotten the feedback that I asked too many questions. Or that I asked them in the wrong way. To be clear I only got this feedback occasionally. I have since taken corrective measures such as searching documentation (if it exists) and taking notes to avoid repeating the same question. I recently started a new job. I frequently find myself in the middle of something that surprises me and compels me to ask questions. For example today I was told to go to an office across the street to do some work. I never new we had an office across the street and don't know why some people work there instead of the main office. While I was in it I asked someone sitting close to me what they do there. He gave a very technical and domain specific explanation that didn't make sense to me. Back at the main office I asked a coworker and he told me not to worry about it. The thing is I work in the IT department and think it would be useful to know where different people work so I know where to go to when I receive a support request. Should I pursue questions like this or just do as I'm told?

As another example most of the staff rotates between two main locations. I have no idea why we do this instead of just assigning staff to one. Is this a bad question to ask? I never intend to "rock the boat" but I think I unintentionally do sometimes. How can I prevent this?

Often times I am asked to do something without knowing the context. Instead of telling me the task I am told the individual steps one at a time. As an analogy it's like someone saying "get a dish, put a slice of bread on it, put peanut butter on the bread, now put another slice of bread on top" as opposed to "make a peanut butter sandwich". I've started replying "what is it we're doing?". Is this OK to ask? As an aside there are many workers who have been with the company for a really long time.

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    Essentially yet another duplicate of workplace.stackexchange.com/questions/192717/… ... Changing tools has significant costs. Even if you can show that doing so will pay for itself, the resources to invest in that change may not be currently available. First focus on doing the job. Log the major changes as wishlist/backlog/technical debt items to be considered when resources are available. Which may not be until the next new-product cycle.
    – keshlam
    Commented Aug 24, 2023 at 4:50
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    Asking questions that enable you to do your job is very important (like "how do I know which building people are in?"). But a couple of questions sound more like veiled criticisms of previous decisions ("what software is so important that we keep XP on the network" and "I have no idea why we do this instead of just assigning staff to one"). Are you really interested to hear why they've done those things, or only to confirm your belief they're doing the wrong thing? Commented Aug 24, 2023 at 7:21
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    @Maximothe1 This is called Legacy software. Entire BUSINESS SECTORS exist on legacy stuff. Heard of the Y2K problem in banking? People didn't plan on their systems to run for multiple decades. It did.
    – Nelson
    Commented Aug 24, 2023 at 8:10
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    @JoelEtherton If you're implying you should stop after the interview that seems spectacularly bad advice. Commented Aug 24, 2023 at 15:17
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    @mattfreake - I'm saying explicitly that you need to start during the interview stage. It doesn't stop. Commented Aug 24, 2023 at 16:26

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The key question isn't only about the right time, it's also the right people.

The general rule of time is to ask questions when mood is neutral-to-good. Any emergency and "drama" situations are really the wrong time.

As for right people - figure out who is more open to help, and stick with them. Ideally, it's your manager, but if that's not happening, find someone else. But due to corporate chain-of-command it should be your boss.

Now, in order to understand if you're really asking too many questions you need to make an analysis: go back in time to the questions you asked, think them through. Could you have asked less or was it fair? Did you exhaust other research options? It may not be your asking that was the issue. It might have been bad management for refusing to give you support.

asked to do something without knowing the context

This is a huge problem with no easy way around it. You need to bring this up preferably to your manager. I don't know your manager so cannot say how he\she would react. Try to frame it as much as "I'm asking for details as it makes my output better". If you think approaching your manager is not a good idea, again, try to find someone else who can help. For the sake of your sanity and performance you really need to ask the right questions (talking from experience here). You have the right to know. If you're getting backlash because of basics, it may be just poor management\company culture. Again, think about how you frame the questions, if there's another place you can look for an answer in try that, but look for a balance.

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When you feel a question burbling up and you want to ask it, stop for a moment and determine:

What will you do with the answer when you get it?

For example, you might "feel better because now I understand something that was confusing me." Or you might "tell the person they can stop telling me step-by-step because I actually know how to make a peanut butter sandwich." Or you might "tell them they are wrong to be doing that thing for that reason and get started on convincing them to change."

You seem to see these as all the same thing, but they're not. Thing 1 is fine, though curiosity and a desire not to be confused may be more valuable to you than to other people, and the interruption for the question may be an irritant. Thing 2 is sometimes fine and sometimes not, maybe this team makes pb sandwiches their own special way and therefore wants to give you all the steps even when you think it isn't needed. Thing 3 is exhausting in a way I don't think you understand at all, so I'm going to elaborate.

Companies exist for a long time. Their assets, like software, exist for a long time, generally longer than the teams that work on them. Process and procedure does the same. Sometimes, these things become out of date. They aren't as good as some other options that exist. When that happens, people look at them and evaluate whether to update or not. Sometimes, they update. Sometimes, they don't. They accept something suboptimal. It might be because the distance from optimum is very small. It might be because there is no time to update, or no-one available who can do it. It might be because they know updating carries its own risks and could make things worse, not better. Whatever, they look into it and they make a choice. They probably revisit the decision semi regularly. Maybe once a year someone says "do we still need that XP machine?" or "should we move the flagship product to another language or framework?" or the like. And people gather a pile of information and make a choice. Maybe they will finally be getting rid of that thing in a year or two. Maybe an upgrade project is bubbling on someone's back burner. Maybe that business line will shut down soon. Whatever. Things are under control.

And then a new person shows up and just keeps picking and poking. Why is this like that? And then some really non-neutral questions, questions that arrive with a giant dose of judgement and scorn like "what software is so important that we keep XP on the network just to use it?" where it's clear, you think these people need to answer to you and to justify their choices to you. When you don't know the story or the reasons at all. You can say you're asking trying to get the story, but the way you're asking carries all kinds of judgement you can't make until you know the story.

And you know, when I've been part of teams that have a suboptimal part, we know it's suboptimal, we wish we could fix it, but money isn't free and time isn't free and Judgemental New Person demanding an explanation as though I answer to them ... I just want it to stop.

So, practical advice. Ask all the "thing 1" questions you want. If some of it is just idle curiosity then say so. "Is there like some sort of weird historical reason for how people got assigned to one of the two locations?". Be cautious with "thing 2" questions. They can carry an "I'm smarter than you're treating me" tone and also risk you doing things wrong because you told someone you didn't need to be shown how to do them. And just stop doing "thing 3" questions forever, unless the person directly reports to you, and even then do them very gently.

In your particular situation, where you have asked at least one "thing 3" question, some people may now kind of cringe when you ask anything, wondering if this is the opening to a lecture about how they're doing it wrong and should adopt some solution that you can tell instantly will be so much better and totally worth adopting. This may make people on edge and reluctant to discuss simple things like who works in which location, worried they are going to be pestered to change an arrangement they're not responsible for.

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    ^This ... So much this! You're spot on, and Thing3 should become part of the workplace lexicon. Commented Aug 25, 2023 at 23:19
  • Thanks for the thought out answer, though I'm having trouble making sense of it. It might be helpful to define thing 1, thing 2 and thing 3 instead of giving single examples. Are you saying all questions fall into one of these three categories? There is often differences between how a question is intended to be perceived vs how the listener perceives it. With your system would you try to predict how it would be interpreted? For example I certainly don't intend to make a thing 3 question where I'm implying I'm smart than them.
    – Maximothe1
    Commented Aug 28, 2023 at 0:25
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    Those are all cases where you are asking because you want or need to know something. When you get your answer you're going to say "thankyou." That's not a problem (though too much if it can be irritating.) It's very different from the cases where you get your answer and say "aha well in that case...." because you were not asking just to gain information. You were asking to set yourself up to do something. It wasn't just a question, it was the start of something. Commented Aug 28, 2023 at 0:34
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    "For example I certainly don't intend to make a thing 3 question where I'm implying I'm smart than them." - but your Windows XP question very much sounds like you've already decided it was a bad decision. So it sounds like you think you're smarter than them Commented Aug 28, 2023 at 14:20
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    It's the way you asked it "what software is so important...". That sounds very judgy, like you've already decided it isn't important enough to justify the decision. The same with why people aren't just assigned to one building, it sounds like you think your idea is better and you're about to try and convince the person you're asking that's how it should be done. Commented Aug 29, 2023 at 5:54
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Honestly, nobody can answer this question for you. Every company is different, and every person you talk to is different. Some companies may have a very open culture which encourages questioning, some may prefer that you act as a good little drone who stays in your cubicle and does what they're told without asking. Same with individual people - some are more open to answering questions than others. Same with different days as well - if there's an emergency, it is generally not a good time to ask "why".

The trick is to develop a good "radar" for the environment you're working in (company, people, time, everything else) and ask good questions when it's appropriate to do so.

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What am I supposed to do, act like it's normal to have a Windows XP machines on the same network where confidential data is stored? I would find that negligent.

No, but you're curious and ask like there might be a reason why that has happened. The way you phrased it makes it sound like you've already decided, as the new person, that there isn't and you know better than the person who's been in the company for X years. Because the person will know that's what you're really saying and won't respond well to your "question".

Once you have all the information, you can act on it if it's your responsibility (or take it to the person whose it is).

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    There is an important difference between asking about something and questioning it. The former is usually benign. The latter has to be done with awareness that there is probably a good reason things are as they are, that changing things can be expensive, that challenging a decision before you understand those drivers is, frankly, arrogant at best... and Isn't Your Job unless they explicitly ask for suggestions.
    – keshlam
    Commented Aug 25, 2023 at 18:45

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