am I annoying my coworkers by asking for a ton of context on everything?

A reader writes:

I am three months in at my new company, and I’m the newest member of a team that only came into existence about nine months ago. There are tons of growing pains/opportunities/whatever you want to call them, but I’m really energized by the atmosphere and I’m generally thriving (as is the team).

I’m inquisitive by nature: I always want tons of context and I tend to ask a lot of questions that boil down to “but why is it this way?” Ths is innate in me, but I amplify it at work because at other jobs I’ve seen insufficient, untimely, or incomplete information torpedo a project or client engagement. Further, because we are a growing team making policy and procedural changes on the fly, I view my approach as essential to ensuring we are looking at a situation from all perspectives.

When I do press for additional context from a particular teammate, I’ve noticed that she will appear flustered or defensive, and I worry that she may feel that I’m challenging her in some way. I am decidedly against “power moves” and I’m sensitive to the scourge of mansplaining (or “man-questioning” in this case). More broadly, I don’t want to appear to my team/management like an annoying wrench-thrower standing in the way of progress.

Is there a way I can couch my questions so that my intentions are clear? Do I have a sit-down with the teammate I’m worried about offending?

I wrote back and asked, “Are you only doing this when you’re heavily involved with a project and really need the context, or are you also doing it more casually, when you don’t really need that context and are more just curious?”

It’s fair to say that this is my everyday default setting, but I amplify it in project meetings/communications so nothing slips through the cracks.

Hmmm. It’s possible for this tendency to be really irritating and to come across in ways you don’t intend — like as challenging a system that someone might not have time to fully explain to you, or as thinking you know better than others, or as focusing on the wrong things at the wrong time.

It’s not that there’s not value in understanding why things are a certain way. That can help you do a better job of your own work, and it can help you and others spot areas where things could be improved or problems warded off.

But just because there’s value in it, that doesn’t mean that you should do it whenever and wherever. There are going to be a lot of times when that’s simply not your job, or where it’s not the most important thing to be focused on at that moment. And if you seem oblivious to that — even though you mean well — you risk really alienating colleagues over time.

Now, if doing this is your job — like if you were brought in specifically to do efficiency analyses or something like that, and everyone knows that — that’s different. Even then, though, you wouldn’t just do it willy-nilly at meetings; there would be a time and a place for it, and you’d have a set of priorities that would govern where you’d focus first. (And in your case, it doesn’t sound like this is your specific job; it sounds like this is just your inclination.)

In general, you need to pick and choose. There are times when it does make sense to dig in and really ask questions and ensure you’re getting all the context (generally, with your own projects or projects where you’ll be playing a major role, or where you represent an important perspective that might be getting overlooked). But if you do it all the time, as your default setting, you’re going to exhaust people and come across as if you don’t understand who’s responsible for what (or as if you don’t respect the people who own the areas you’re questioning and questioning), or as if you don’t get what it makes sense to spend time on and when.

If I were in your shoes and questioning how this might be coming across — but not convinced it was a problematic behavior — I’d ask people straight-out. With the coworker who seems to be bristling when you question her, you could say something like, “Hey, I sometimes ask a lot of questions because I do better work if I understand the context for something and I like to look at a situation from all perspectives. But I don’t want to overstep, and I’m worried that I may have. Am I reading you correctly in situations like X and Y recently that it was too much?” You’re not looking for a yes/no here so much as you’re looking for a conversation — it’s giving her an opening to talk about how this is landing with her.

But no matter what she says, you really need to consider whether, in any given situation, it’s your job to look at the situation from all perspectives. For most people, it’s going to be their job sometimes and someone else’s job other times. When it’s someone else’s job, they might welcome input sometimes — but not every time. And they probably won’t welcome feeling like you are stepping in to do their thinking for them, especially when giving you the full context might take significant time that they don’t have.

Read an update to this letter here.

{ 365 comments… read them below }

  1. Ms.Vader*

    Reading the letter, it does come across like you are doing this because you don’t trust that anybody else has discussed the points you bring up so that can come across condescending. Perhaps that isn’t your intent or your viewpoint, but that did stand out to me.

    If you know the times when are just asking for the sake of asking without it really contributing to the solution, perhaps you can say something along the lines of “I think i understand what I need to do for this project; but I have some questions that I am just generally curious about and it may help me do this job better. Do you have time to answer some more quick questions?” And then limit yourself to like 3 or so questions.

    By just asking a lot of questions that people don’t understand why you are asking can really get people’s back up. I would feel better if I knew what context I myself was providing answers to.

    1. Knork*

      That stood out to me too. Sometimes an organization has growing pains, and sometimes lack of information can cause problems, but those aren’t always your problems to fix, and it isn’t always your risk to manage.

    2. smoke tree*

      Yeah, I think as a new person, you especially need to avoid creating the impression that you’re challenging the way everything works. It sounds like this letter writer’s intentions are good, but he’s going to risk alienating everyone else on the team if he inadvertently makes it seem like he’s appraising everything they do, or quizzing them on their jobs, or even just if he seems to think his need for background information is a higher priority than what they’re actually discussing.

      When the urge for context strikes, unless it seems urgent, I would suggest writing down the question, taking some time to observe and try to find out information independently, and then if you still have questions, bring it up later at a time when your coworkers don’t seem too busy. I think being considerate of coworkers’ time is one of the most important ways to make a good impression in a new job–plus if you’ve already tried to find out some information on your own, you’ll have more to contribute and won’t risk sounding like you’re testing them.

      1. Amber T*

        Yes – I was that new person who asked a lot of question and made a lot of suggestions. I definitely overstepped at times, but thankfully I had coworkers who laughed it off, didn’t take it personally, and basically said I’d understand why we do things a certain way once I’ve been around longer. And it’s true – I have. Sometimes “inefficiencies” to an outsider/someone new aren’t actually inefficiencies.

      2. Blue*

        I like your points here. I’m definitely a questioner myself, and knowing the why is actually a really critical part of the work I do, but I was hyper conscious about hammering people with “whys” when I started a new job last year. I found it helpful to contextualize my reason for the question. Especially as a new person, “I want to understand this better so I can be better at my job and operate more independently moving forward,” generally comes across as a reasonable motivation, versus an implied, “I want to know more about this because I don’t trust that you thought it through all the way.” Tone can also make a big difference in how this comes across, especially if you’re following up with more questions.

        And I fully agree with holding back some of your questions and trying to draw conclusions on your own. If you wait, you may observe a few related things and spot a pattern. Asking your coworker to confirm that you’ve come to the correct conclusion rather than expecting them to explain from scratch generally lessens the burden you’re placing on them. If nothing else, you’re consolidating your annoying questions into a concise time period instead of bugging people all day!

      3. RUKiddingMe*

        This. My default setting is “why.” I’ve learned over the years that context usually happens without annoying all and sundry…and if it doesn’t, and I need to know (read: *need*) then I can ask.

        OP identifies as male and specifically states he doesn’t want to come across as mansplaining. Good for him. I will point out that when questioning women colleagues about “why,” especially as the new kid, this can definitely come off as “explain yourself to my superior male personage.”

        Not st all saying OP thinks this, or that his coworkers do, but they might. It’s a risk.

      4. Glitsy Gus*

        I really like the writing down the questions and saving them for a bit suggestion. Not only will it keep meetings moving and prevent coworkers from feeling like you are challenging or questioning them, but you may end up getting the answer to your question a little later in the meeting. If you do still have a few questions that haven’t been answered at the end, you can either speak up about those ones or do a bit of digging yourself.

    3. Future Homesteader*

      Yes! I really like your language. Context for the questions always helps, especially if it’s a situation where you’re worried about coming across as confrontational. It also helps the questionee (?) frame their answer so it’s most helpful for your purposes.

    4. CmdrShepard4ever*

      I identify with the OP. I am very curious/inquisitive by nature, but have had to learn to curb this both in professional and personal setting.

      My team used to be smaller and I generally knew what everyone was always working. As our team got a bit bigger (it is still small just a few more hires) I have not been in the loop on what everyone is working on all the time. While I am curious, it doesn’t impact me and I don’t need to know.

      Personally when speaking with my significant other many times I ask questions about small details that I don’t need to know or matter again for curiosity. My partner on the other hand has the social capital to say, “You don’t need to know that, or you are asking too many darn questions again.” They also know when I am curious or have a question about something, I won’t be satisfied until I Google it.

    5. designbot*

      I really like that framing, because that gives the opportunity to say “no, actually I don’t have time right now, I really just need help putting out this fire.” or “This isn’t a great moment for that, but circle back some other time if you’re still interested in learning more about this area of the business.”

    6. a1*

      I think it’s a weird assumption that just because someone asks questions means they are challenging anyone or anything, rather than just wanting to learn how things fit into a bigger picture. I know this is a common reaction, but I just don’t get it. I remember one of my first jobs my colleagues warned about working with John D “he’s a real ass”, “he doesn’t trust anything”. When I finally worked for him I was surprised. I thought he was very easy to work with. Yes, he asked questions, but that was to fill in his own knowledge gaps. He was the one that had the most contact with our clients (although my department did, too, just not as much) so he was going to need to be able to answer any questions they may have. And since he knew the clients well, he knew what kinds of things they’d ask. And the thing is, he’d only ask each question once. He wrote it down, made sure he understood and that was it. He wasn’t “questioning” anything or anyone. I actually really liked working on projects with him,

      1. Falling Diphthong*

        A non-work example would be the gatekeepers of nerd culture. What one person perceives as “Great, we can talk about Doctor Who!” their target perceives as “Think you’re a Who fan, huh? Well here’s a quiz…”

      2. Liz T*

        Well, people make that assumption because they’re usually right. People often question INSTEAD of outright saying, “that’s a bad idea/I don’t want to do that” because we’re trained that outright statements are aggressive but ‘just asking questions’ is not.

        1. Ethyl*

          “Just Asking Questions” is even a known trolling/derailing tactic! It’s not a massive illogical leap to think someone might not be engaging in good faith when constantly questioning you.

          1. Clever name goes here*

            OP sounds exhausting, to be honest. Sometimes asking questions is completely appropriate. Other times asking questions telegraphs self-centeredness and entitlement (I’m curious about this so why don’t you turn yourself into a human google result and tell me what I want to know). Some people know the difference. Some very clearly do not.

            Nobody wants to be grilled by Mr. just got hired about why everything is the way it is, especially in the absence of any immediate need for the new guy to know all that.

            1. JelloStapler*

              I have an employee like this, that I believe is all in good faith, but often comes off like “you are all doing what I think you should be doing”. It IS exhausting, especially when many of those very things are completely out of our hands and our organization is very slow in response.

      3. designbot*

        honestly I think there’s a lot of cultural and intersectional overlays to this. In my schooling, the professors did this during design reviews and it was both to get an understanding of your thought process *and* an attack. Someone they really liked would get softball questions with little followup, someone they didn’t would get hammered on issues that were overlooked for others, always in the form of a question. A side effect I’ve noticed of that is that it sets the questioner up as a gatekeeper, to use the very apt word from Falling Diphthong’s post. And those gatekeepers are usually male, usually white. I know I notice I get questioned a lot more than men at my level do, usually by men, and once you notice that it’s hard not to see it as a challenge.
        I know it’s probably tempting to say oh, but this is particular to your industry and not universal, but consider the Socratic Method. It relies on teaching through questioning, and is the foundation of for example medical education. Many of us are taught that questions come from teachers, not from learners, and it is the responsibility of the person being questioned to prove their knowledge to the person questioning. I think that’s a major cultural context we can’t just decide we should all ignore one day.

        1. Else*

          Very, very good point. This speaks to something I’ve felt but not articulated, thank you.

        2. Saint Dorothy Mantooth*

          “…and it is the responsibility of the person being questioned to prove their knowledge to the person questioning.”

          Oh man, you nailed it. Very well put.

      4. Princess Consuela Banana Hammock*

        It’s not the questioning that’s inherently challenging. It’s the tone, frequency, and context. If you ask broad “why” questions, it’s going to sound like you’re asking someone to justify or defend why they made the choices that they made. But if you disclaim your learning style (e.g., need the context), ask targeted questions in a humble way, and ask a person if they have time to talk to you, they’re more likely to accommodate you and give you answers.

        All of us have conversations where we’re asked to explain our approach, but we shouldn’t have to do it every time we converse with a particular coworker (because it’s a time suck, it can undermine relationship-building, and it can begin to feel like the questioning coworker is challenging your competency). That’s especially true when you don’t understand the other person’s motives for asking the questions—general curiosity is usually not a good reason to derail others’ time.

      5. The Man, Becky Lynch*

        I think it also stems from some people thinking you should just know things or wait and see how they all click together, instead of straight out asking for an explanation or details.

        Thankfully it’s always within my job scope to ask questions and I’m happy to answer them as well, I’m usually the person people ask first at this point in my career. It always makes me so flustered that so many people are conditioned that asking questions is bad and poorly received, so I get people sliding into my office almost like they need to tell me a secret but it’s actually to say “I’m so sorry to ask but how do we XYZ? Has this happened before? How can I prepare for it next time?” and I’m like “Dude…asking questions is part of the learning process, I’m not going to eat your face [today, for this but maybe tomorrow for something else, sometimes I like to eat faces!]”.

      6. Not So NewReader*

        It’s the multiple questions that tip the scales.
        It does not sound like OP is just asking questions for the sake of doing her own work well. She is also looking at processes that are department/company wide and questioning things.
        When training a new person or getting them up to speed on something, endless question or unfocused questioning can derail the training. It does not feel like training any more, it feels like brain removal. “I want to know everything you know, so tell me now.”

        I can point to numerous examples of time where people asked too many questions and failed to learn the task in front of them.

      7. ket*

        There is something in the manner of asking questions that can influence this; part of it is whether someone will accept an answer. If someone ask, “Why X?” and you say, “Because Y,” and they follow up with, “well did you think of Z? what about W? are you sure you considered V?” endlessly, it can get frustrating — and when sometimes the answer is, “Because I like A better” and they continue that, it can drive one nuts.

        “Why do you use green ink?” “Because I think it’s pretty.” “But did you try blue?” Argh!

    7. Hey Karma, Over here.*

      “I view my approach as essential to ensuring we are looking at a situation from all perspectives.”
      I think it is important for OP to make sure he understands it from his perspective first. I think it would help if you took a step back, reviewed the process and see if you can determine the answers yourself. I’m a big questioner in meetings (I’ve learned to limit to three as a rule) but I’ve also found, after 20+ years, that if I start my part one of two things tends to happen, I either realize as I’m doing it this way or I see a specific issue or two. I can go to my boss with I don’t understand why we’re doing X because Reasons. About 30% I get, whoa, damn that’s not going to work. The rest of the time, there’s a rule/procedure/other dept thing that explains it. But I don’t know that, because it’s not in my purview. Learn everything you can, but learn more by doing than asking.

      1. Willis*

        That line popped out at me too. If a big part of OP’s job is to make sure the team is “looking at situations from all perspectives,” than that would be one thing. But if it was another coworker’s job to develop Process X or Project Y and they do so, a lot of questions can begin to look like you don’t really trust their work or their own ability to look at different angles. Sure, it may be an essential thing to do, but is it essential that you are constantly the one doing it? If not, I’d focus on questions that really truly have to do with context you need and reign in the others.

      2. Not So NewReader*

        Looking at a situation from all perspectives is not always doable in the work world. That is more of a classroom exercise where time is a luxury. Time is much more compacted in the work place. More often than not you are making your best guess and running with it. This is why some people are allowed to guess and others are not, because the best guessers win here.

        1. Observer*

          And sometimes, even when it’s doable, trying to consider something from every perspective is not a good use of time. And sometimes it’s even counterproductive.

      3. Yorick*

        Yes, that line sounds like OP thinks he’s smarter than everyone else and assumes that no one else has thought of everything, which is especially problematic because he’s new.

        Of course, he might not actually think those things! But it does sound like he could have at least a touch of that mentality and he should consider where that comes from and how it affects his relationships with coworkers.

    8. BethDH*

      I like the idea of limiting the number of questions too. It seems to me that OP might need to learn to prioritize questions because it sounds like his questions have become a dominant part of interactions with coworkers. He mentions that he’s sensitive to this because lack of information has been a problem in the past, so if he can think about what types of information are most critical and ask only about those things, that will help show that he values his coworkers’ time and isn’t just trying to pick holes in their processes for fun.
      It also might be worth listening to the whole explanation or assignment first, then taking a few minutes to collect the questions after that and present them at once. I’m an over-questioner myself, but I’ve also had really annoying interactions with people who don’t wait to ask their questions and ask something that would be clear if they waited through the explanation and then considered it in context.

    9. Princess Consuela Banana Hammock*

      I agree, and I think this is important insight. If someone were constantly asking me questions that amounted to “why do we do this this way?” or “why did you take these steps?” I would find it tiring. And if it happened every day on everything, it would make me defensive.

      I like all of Ms. Vader’s scripts, because they’re more likely to get someone to see the interaction as a collaboration instead of an interrogation.

      [I say this as a person who needs to understand the context to produce a strong work product.]

      1. Not So NewReader*

        Unless a person is hired just for their ability to ask questions, it’s probably a good idea to severely limit the number of questions and chose the ones that are of immediate practicality.

      2. BoredFed*

        I fear that OP may be conflating “context” with detail.

        When I’m explaining issues within my area as SME, I try to first explain the context, that is, the intellectual framework. For example, “This is what we see our customers looking to accomplish by conducting a tea ceremony. That context drives, in significant part, the shape of the teapots and cups, the materials we use, and the images we paint.”

        Understanding that framework helps folks see where details fit, and teaching it is the equivalent of “teaching a person to fish rather than feeding them fish.” It is part of the duty to explain well.

        But “context” in this sense is measured in ounces rather than tons. By contrast, a person asking dozens of questions at a granular level about “why did you do this this way” would soon … exhaust patience.

    10. Sleepytime Tea*

      As someone who loves to know the WHY of things, and I’m an analyst so that’s literally in my job description sometimes, I can also say that it is important to know when the “why” is important and when it isn’t. If you’re asking “why” because you have suggestions on a way to make things better, and need to understand if there’s a specific reason why things are the way they are first, then that is incredibly valid. If you are asking just because, then you are just questioning needlessly and people can take that as you wasting their time or challenging everything unnecessarily.

      Example of a good why: “I’m wondering if there’s a reason we put the teapot handle on last in the production process, because I was just thinking that if we put it on before the lid then there’s less chance that we would knock the lid off and it could save us a lot of money on replacement lids.”

      Example of a bad why: “Why do we put the teapot handle on last?” That’s where the machinery is set up. “Right, but is there a reason it’s set up that way?” Because that’s the only place it fits on the production floor. “Was there a reason we couldn’t reconfigure the production floor so that it could go in a different place?” *Coworker beats head against the desk.*

      The big difference here is that in the first example you have a specific reason for your why, and you’ve given the context for it, and the person can then give you exactly the piece of information you’re looking for. In the second example the conversation can carry on like it does with a 4 year old, asking “but WHY” a million times without ever getting to the point, which yes, will drive people insane.

      If you want someone to invest time answering your questions, there needs to be value to it. And really, your time has value too. If you’re asking why and spending a lot of time (potentially holding up meetings!) on getting these answers, but at the end of the day it’s not adding any value, then as Alison said, you need to take a close look at whether the questions you’re asking are actually contributing to your work product in some way.

      1. a good win*

        I like your examples a lot. It’s clear the first one is going to quickly lead to the context you’re looking for, where the second is more meandering and feels more aggressive, probably because the answerer can’t tell where it’s going or how to answer such a broad question that could be answered lots of ways.

      2. Teapot analyst*

        I am also an analyst, and find myself genuinely curious about a lot of random things. The big advantage is that the curiosity is directed at many different people. Yet most of them are strangers, so I have had to work on my approach. I find that an honest “That’s neat! Do you mind telling me more?” opens the conversation very quickly. When I *need* someone’s answers then I am more direct and explain myself “I’m an analyst, working to improve handle design so that you can get a better grip, so when can we talk for a few minutes?” These are different contexts than the LW, but it shows that people who ask “Why?” for a living can aim to be thoughtful about it. In technical discussions I also aim for bonus points by providing context of my knowledge – if I need to talk with someone about blue glazing then I give a couple lines about my experience with red and orange glazes, so the conversation takes less time.

        In all honesty the LW sounds exhausting. I know analysts who question everything and it is often because they don’t listen very well, or aren’t willing to do a bit of research. I may be wrong about the LW but I have met people who have similar views of themselves, and they are almost all completely well meaning but also time-sucks.

        1. Safetykats*

          Yes, this. A big part of my job is educating people on the how and why of specific evaluations that are part of their job. When you ask me questions that you could have discovered the answers to by reading the procedure, or the instructions to the form, or the referenced technical basis documents, you just show me that either you’re not competent to do your own basic research, or you don’t respect my time. I would recommend OP make sure that they’ve done the research they can do before asking questions that require more experienced – and possibly more valuable staff to spend their time explaining things that could easily could have been discovered by another means. In the end, most people will be less annoyed, and more impressed.

        2. Sleepytime Tea*

          I do this to! “Wow that’s so cool! Do you have a few minutes to tell me more about that?” gives people the opportunity to share knowledge with you, and gives them an out for “I don’t have time right now, but sure, let’s get together later.” And if I come in and say “So I know x, y, and z about this thing, but I want to make sure I am taking everything into consideration for my project. Is there anything else I should be looking at or that I should know” lets people know that I am coming to them with my ducks in a row and already have a basis for my questions.

          As an analyst you have to rely on so many other people to give you information that you get a lot of practice in what approaches result in something productive as well as create positive relationships. If you think I’m annoying and constantly bugging you then you are less inclined to spend time helping me in the future.

      3. Teapot Painter*

        Oh my gosh, Sleepytime….one of my family members is the definition of the “bad why” person, and it is indeed the most infuriating thing ever!! And then the family member gets huffy when the misleading and rambling questions don’t get the answer to the actual question, which the receiver of the question doesn’t know of course. It’s an awful vicious cycle. Thank you for laying it out!! Now I understand more about why I get so frustrated.

  2. Not Me*

    I think you can ask “why do we do it this way?” for anything, it’s the timing that matters. It might be better after a project is completed if your sole purpose is to better understand. “Now that we’re done with that project, can I ask a few questions so I better understand the whole process for next time?” is totally reasonable.

    The most expensive phrase to any business is “because that’s how we’ve always done it”. I see the OPs thought process as a very healthy view for any business. As long as it’s done at the right time and in the right way.

    1. Sleepy*

      It’s also exhausting to get new people who are enthusiastic about changing processes, when a lot of the obvious changes have been tried already and rejected because, well, they didn’t work. I’d rather have someone new who genuinely wants to understand why things are done a certain way rather than going full-bore on suggesting changes without bothering to understand the context. Definitely, choosing the right time and tone is key.

      1. a1*

        Just because someone asks questions doesn’t mean they want to change anything though. They just want to learn.

        1. Washi*

          I don’t mean this unkindly, but I’m not sure the OP is fully owning her motivations in this letter. She says she just wants context, but she also says “at other jobs I’ve seen insufficient, untimely, or incomplete information torpedo a project or client engagement.” I get the sense that if OP thought something could be improved, she would say so.

          The thing is, you have to play the long game as a new team member. My current newish job has processes that are ABSURDLY inefficient holdovers from 1980s level of technology. But for a variety of reasons, that’s the way things are done, and if I go in guns blazing, I might change one tiny piece of it, but also everyone will hate me. I’m focusing on improving things in my own small area and building capital, and gradually people have started coming to me more and more for advice on improving things, which is a much better position to be in!

          1. Not Me*

            But he would have to know why something is done the way it is before suggesting improvements. He’s not saying that he blindly runs into a project meeting and starts barking suggestions. He asks questions to better understand “why?”. I think the key to the sentence you quoted is “…information…”. He doesn’t say “I can fix it all!”, I take this as “if the right questions are asked, the right information is considered”.

            Again, I said the where and when of this question is key. If done at the right time and place this is a question no reasonable manager or organization should have a problem with.

            1. katelyn*

              If you live with a toddler for any length of time you will learn how exhausting “why?” can become. I concede that knowledge is important, and an understanding of processes is necessary for work to be completed in a timely and efficient manner.

              But your co-workers aren’t your parents or your teacher, sometimes you need to put in the time to observe and figure out the why for yourself as you process things… which is what we ask of all new learners after they have made it through their earliest “why” phase…

              1. Eukomos*

                I’ve never had a toddler, but my impression is that they just ask “why? why? why?” endlessly. As someone who always needs to know the context, I make sure to have an end! I just genuinely need the contextualizing information. When people give me an instruction I need either a very clear description of the desired result or a little basic context to carry it out correctly, otherwise I always manage to forget a detail that I didn’t know was important or misconstrue something. With the context for why we are doing what I’m about to do, I do an excellent job. A little extra time at the front end making sure people understand the reasoning behind the task can really improve outcomes, and it doesn’t have to take very long.

                It’s also critical to my morale. Even outside of work, if a doctor says “do this exercise daily” without explaining why it will help, I just…don’t. It seems unimportant to me if I don’t know why I’m doing it. I don’t do well being treated as a mushroom!

                1. Gerald*

                  I agree completely, but in this case I think the issue is that one shouldn’t need to know Why for everything, when it is just for curiosity and not necessary for their work. My doc would give me a funny look if I asked Why my cousin’s neighbour needed a knee replacement.

            2. I Took A Mint*

              “But he would have to know why something is done the way it is before suggesting improvements.”

              Sometimes it might not be the time or place (or his place) to suggest improvements. He says “I view my approach as essential to ensuring we are looking at a situation from all perspectives” but is this always the role he has been asked to play? Is this always the highest priority, or should his curiosity sometimes take a backseat to a tight deadline, or to respecting a colleague’s intelligence enough to trust that something is well-thought-out? It’s clearly damaging his relationships so I think OP needs to dial it way way back.

          2. Barefoot Librarian*

            I was in a similar position when I came to my job four years ago too, Washi. It was literally in my job description to manage our systems and software and they were ANTIQUATED. However, I knew that before I changed everyone’s world I needed to fully understand how and why they set things up the way they did and, more importantly, build professional and personal capital so that when I did make a big change, people would know me well enough to trust me. I ended up completely overhauling our central system a couple of years in but it would have been a terrible idea to do it earlier.

        2. Princess Consuela Banana Hammock*

          I think it’s important for people who ask a ton of questions to be aware of how they’re perceived. Folks can rail against the “assumptions,” but all of the reactions folks are listing are common pitfalls that new employees fall into.

          The advice is keyed to helping OP stay out of those pits, which is something somewhat within OP’s control. Railing against the existence of the pits isn’t actionable or within OP’s control.

        3. Yorick*

          But OP seems to want to know the context in order to suggest improvements though, and that’s not really appropriate when you’re this new (unless that’s specifically his job)

      2. Cattiebee*

        I really want to emphasize the point about tone. OP, maybe run a sample of the types of questions you tend to ask past a close friend whom you trust to be really honest with you in order to assess your tone and word choice. “Why did you do that?” and “I don’t understand why you did that” said in a genuinely friendly and curious tone will be received entirely differently than those exact same words said in a condescending tone. The former suggests you want to learn, while the latter can come off as if you’re asking/demanding your coworkers to explain themselves to you.

        The same thing applies with word choice. If you’re asked to document two things that seem similar to you in completely different ways, for example, saying “hey these unicorn flying reporting requirements seem a lot more complex than the unicorn dancing reporting requirements we discussed last week. Are there additional government regulations or anything else I should be aware of when reporting flying unicorns?” sounds a lot better than, “ok, well, last week you said I only have to file annual reports on dancing unicorns, so why can’t I do the same for flying unicorns?” The first sounds like you’re trying to get the details correct to excel at your job. The latter sounds like you’re challenging their system before you even understand it.

        Having a trusted someone to give you feedback on how your communication style is being perceived by others might be really valuable here.

      3. nonymous*

        >when a lot of the obvious changes have been tried already and rejected because, well, they didn’t work

        this describes all my coworkers. and then when I present topic in an organized manner – so that they can see all the rejected options and I don’t have to repeat that process they complain it’s too much detail.

    2. Serin*

      I think it’s a great idea to ask questions after, rather than during, a process. In some office cultures you could even schedule a meeting for postmortems and lessons learned.

    3. HalloweenCat*

      I completely agree! Sometimes the most obvious “but why” question is one that hasn’t been considered! Recently, I was brought in on a project in the lates stages. They asked me to figure out the most cost-effective way to have envelopes printed with our return address but then individually labeled with mailing addresses. I let them talk through what they needed and when they were done I asked one question: “This might have already been discussed, but why aren’t we using window pane envelopes?” Because no one had asked if we could yet! (We could.)

      1. Observer*

        Of course. Context matters, ironically. In this case the context was that you were there to *change the process*, so it was reasonable to ask why the process was the way it was and not a different way. But if you were brought in to discuss how to report the expenses to the entity paying for the project, the question would be a lot more iffy.

    4. Pilcrow*

      Totally agree with the timing portion. If there is a deadline or time-sensitive issue you just need to get the job done and then you can do a review afterward. If there is a fire and I ask you to turn on the hydrant, that is *not* the time to question why the hydrant is behind the building, why it uses that size hose, and why does the company use a water system instead of halon.

      Some suggestions:

      Don’t fire off questions in the moment. Peppering people with random questions when they just need something done tends to put people on the defensive, especially if they are under pressure. Another thing to keep in mind is that people may not be switching gears into analysis mode when their minds are in execution mode and your questions are making them lose focus.

      Make sure you’re asking the questions to the right people. Maybe they don’t know the answer. That tends to frustrate people.

      Ask quality questions, not random fluff. Make sure that your not asking questions you could find out yourself with a little extra thought or research. Getting asked to explain simple or irrelevant stuff is annoying.

      Try collecting questions in a document. This helps organize your thoughts to focus in on what you really need to know.

    5. Is It Performance Art*

      I work in a STEM field and we do a lot of process documentation, so this may or may not apply to your field, but the documentation for processes can be really helpful for this. Calling Mattresses Dog Kennels sounds counterproductive, but if one of the sales people puts a paper bag over his head anytime someone else says “mattress”, there is a reason and in most places i’ve worked, something this important will be noted in the documentation. Documentation can also be really helpful because sometimes the reason you do X the way you do becomes pretty clear as you get further in the process. This can save time for everyone.

      1. Calpurrnia*

        Came into the comments looking for discussion of documentation! I’m a person very much like the OP (voraciously curious, wants to know how everything fits together into the bigger picture, doesn’t like being told “because that’s the way it is”…), and I’ve found that you can totally sidestep a lot of people’s instinctual “bristle” reaction to being questioned if you frame the question in a documentation context. People are much more willing to share their knowledge when you’ve basically up-front implied “you’re a wealth of valuable information, I’m not at all doubting your process, I want your input to make sure I get this right in the docs I’m building to make this easier for all of us”.

        To figure out how much of an undertaking the documentation part will be, start with “can you point me to the place on the intranet/wiki/etc where I can read more about this process?” Plus, look through what (if anything) they dumped on you as a new hire – powerpoints, background info, whitepapers, whatever else? – and get a feel for what’s in there and, more crucially, what isn’t.

        Then (if your workplace has a strong, already-established documentation culture) you can do your research and answer your contextual/curiosity questions on your own time, without taking up tons of other people’s time. And when you go back to them with a followup question, you can open with “I read through that site you sent me and it was really informative, thanks! I was curious though if there’s any more detail somewhere on the X process, since it’s mentioned in a few places but never really explained. Is there somewhere I can look for more on that, or someone to ask about it?”

        Or, if they don’t have much documented, gave you nothing to start with, and/or they don’t have anywhere to point you when you ask for it, take it on yourself as a project!! “As I’m learning and getting up to speed, I’d like to get all this background and contextual info together and build/overhaul an onboarding docs site for future new hires. Can you walk me through how this process works and why we do it this way?”

        Basically, if you’re going to all this trouble to learn and ask all these questions, then document them so that future people will be able to get answers themselves. Build a website or write a manual or whatever makes sense in the context of your workplace. Gather up whatever materials are already out there, and overhaul them so they cover the level of detail that you’re asking for. Then in a month or a year when another super-curious newbie comes in asking the same questions, they can be pointed to this awesome reference that’s a wealth of info to sate their curiosity and broaden their knowledge, rather than making the old-timers roll their eyes like “oh here comes another upstart who wants to know everything about everything in week 1”.

        I think that most people will be a lot more generous and a lot less likely to think you are questioning/doubting them if you make it clear that you value their insight so much that you want to capture it for knowledge-sharing and documentation purposes. (I’ve found this to be true of *most* coworkers, personally; the remaining folks who resist giving straight answers, keep everything close to the vest, and won’t share knowledge in the interest of “job security” or whatever… are usually terrible team players and not long for any functional workplace, IME. Unless, I suppose, you work in a field where security is a significant concern and “need-to-know basis” is a phrase that gets used? Which a. you probably already know if this is the case, and b. might not be the best fit for an insatiably curious personality. Again, from my own experience.)

  3. Not All*

    This letter gave me flashbacks of an old coworker. Whenever his name was on a meeting invite, we automatically doubled the time allocated. Drove everyone absolutely bonkers and wasted So. Much. Time. Whenever efficiency was important, we learned to schedule meetings when he wouldn’t be available. Not good for his career but he rode the “it’s important for me to understand context” and “it’s just my nature” horse into the ground. One regular meeting leader resorted to giving him tokens at the start of each meeting and he had to pay a token each time he spoke…when he was out of tokens he had to remain silent the rest of the meeting. Worked pretty well but she was the only one with the political capital to get away with it and for some reason even THAT didn’t get through to him that he was generally asking way too many questions in meetings!

    1. Serin*

      Oh, man, I wish I had tried that technique for a former co-worker who never shut up (not questions, in that case, just endless chains of irrelevant anecdotes). At a certain point you stop worrying about hurting someone’s feelings and just try to do something that will stop you from nailing him in a box and shipping him overseas.

    2. Liz*

      I love the token approach! While thankfully I don’t have many meetings at all in my current job, this generally reminds me of that annoying person in your mind-numbingly boring college class, where the professor drones on endlessly. You know, the one who, when the prof. asks if anyone has questions and everyone holds their breath except that one, who proceeds to ask 9 more questions that are not simple yes or no

    3. LSP*

      I used to work with a woman who seemed to always find a way to bring the discussion back to herself or her son who was on the autism spectrum. The job was not focused on kids, autism, special needs, or anything else where that would be relevant, but that didn’t stop her. She would monopolize Q&A at every staff presentation just to talk about *her* personal experiences (sometimes about her son, sometimes about being a woman, sometimes just to make a bad joke that was completely out of context). Or she would ask questions that made me think she hadn’t actually been listening to the presentation at all, and was just waiting for her time turn to speak.

      I did a Six Sigma training with her and it was almost intolerable how she just refused to engage in the topic we were actually supposed to be discussing in favor of personalizing everything.

    4. bikes*

      I wish I had the nerve to try the token system with my resident why-guy. One time, we spent an hour and a half discussing why our electronic files were organized the way they were and why he couldn’t re-org during his first week on the job.

      OP, you *will* get invited to less meetings and ultimately have less say in important matters if everyone feels like you are grilling them while they are on deadline.

    5. ..Kat..*

      Doing this in meetings has the potential to waste the time of many people at once. When I have worked with people like this, they did not come across as wanting a better understanding. They just came across as time wasting jerks who thought they were so important (they weren’t) in the organization that everyone else had to explain everything in minute detail so that the jerk could give his (unnecessary) blessing to a process that had nothing to do with him.

      I recommend that you pull back and only do this when necessary.

    6. Software Engineer*

      Just repeat ad infinitum “let’s take that offline,” that’s the corporate speak we use at my work to say we’re ratholing (whether because people are going around on something important but that doesn’t need the whole room or because somebody is asking questions not totally relevant)

      You have to have people who are leading the meetings knowing that they’re in charge of the meeting and can redirect the conversation as needed and not just be held hostage by some dude

    7. Jules the 3rd*

      Yeah, the key takeaway for me is: Don’t do the questions in meetings with everyone.

      Pick 1 topic from a meeting, write down the topic and who seems to know about it. Ask one person, outside the meeting. “X was mentioned in the meeting, and as I’m still learning, I wanted to get more background on that. Can you tell me why we do X / do X that way?”

  4. Amber Rose*

    I generally don’t mind explaining things to people, but there’s definitely a time and a place and sometimes there are very good reasons why we do the less efficient X instead of Y, but to explain that to someone who is just curious would take a while, distract me from what I’m doing and generally be sort of pointless. A lot of the time, you pick up the whys and whats just by working there long enough and seeing things in action.

    OP, in a new team with growing pains I’m betting you’re all wildly busy and maybe putting out fires on a regular basis (as this is how my own company stumbles along). Your coworker may seem flustered because you’re asking her to switch gears from “oh god everything’s on fire” to “we do X because [long explanation]” and then back to firefighting, which is not… great.

    I get that you want to know lots of stuff but you’re super new. Try to figure out some stuff for yourself first and give it some time.

    1. Not Me*

      This is a great way to raise new talent who have no idea what they are doing and then penalize them when they aren’t doing what you want them to do.

      He has questions he thinks will help him do his job better. If those more senior in their roles or in the company don’t have the time to answer questions, they need to hire someone who does to manage the less experienced talent.

      Hiring someone new and expecting them to not ask questions and just follow along hoping they understand is an equation for failure.

      1. Amber Rose*

        No, the OP has questions about things they are merely curious about. That’s very different from asking questions relevant to a current task.

        1. Escapee from Corporate Management*

          Amber Rose nails it. This is not telling OP to never ask questions; it is when and how. If you need the information to get the job done correctly, ask in the moment because getting it wrong is not an option. If you are curious about the process, but asking the question would impede the timeline, schedule time to have the discussion afterwards.

        2. Not Me*

          He didn’t say he was merely curious. He said he’s seen in previous roles “insufficient, untimely, or incomplete information torpedo a project or client engagement.” and he’s hoping to help stop that from happening in this organization.

          If they didn’t hire him for his insight on these kinds of things, that needs to be addressed with him. If they did, they need to allow him to ask “why do we do it this way?”. Diversity of thought is invaluable in a lot of organizations. Waiting and watching and hoping you figure it out is most likely not what they hire new people for.

          1. Amber Rose*

            It doesn’t sound like they did hire them for that though, and as for that being addressed with the OP… like, that’s the point of this whole letter. Maybe go back and read it again? I feel like we’re talking about two different subjects here.

            “Waiting and watching and hoping you figure it out is most likely not what they hire new people for.”

            No, but as has come up numerous times, a good trainer allows the new hire to try first, then ask “I think this is what’s up, am I right?” As opposed to just giving them all the answers. 3 months is very soon to be grilling people on every little thing, when much of that would be learned in the process of doing work over time.

            1. tassieTiger*

              It could definitely just be that I work in food service-but having someone try something first without training would be a disaster.

              1. Not So NewReader*

                And in many arenas. I have not found a place yet, where I would throw caution to the wind and let the newbie “try it” without some instruction/preview from me.
                While a new hire should not stand around day-after-day until they catch on, there are times where it is totally appropriate for a new hire to step back to watch and learn. And some of that is expected.

                For me, an example of when I would step back is if cohorts are arguing about a specific situation that happened before I got there. That’s one example, I have a few things that I try to avoid getting involved in, I just observe and soak up information.

          2. Polynesian Sauce*

            If OP was hired for that they likely wouldn’t have written in asking in the context they did. Diversity of thought is only valued when your thoughts are useful. Before you learn a process your thoughts aren’t useful on that process and asking why is this this way while learning how isn’t helpful.

            1. It’s A Bird, It’s A Plane, It’s SuperAnon*

              “Diversity of thought is only valued when your thoughts are useful”

              I need this cross-stitched!

            2. Not Me*

              “Diversity of thought is only valued when your thoughts are useful. ”

              How does anyone know if his thoughts are useful if they don’t consider them?

              Regardless, he hasn’t offered any thoughts. He’s asking why things are done the way they are. He’s at the “how does this work?” stage of the process. He’s trying to do his best to understand what is happening. He didn’t say anything in his letter about making changes or giving input.

              1. sunny-dee*

                Which is the problem. (You can’t defend his incessant questioning as “diversity of thought” when he’s not offering any perspectives, it’s not his role, and there’s no reason to believe that is why they hired him.)

                He flat-out says he just likes asking questions and amps it up at work. Honestly, the “I’ve seen stuff fail for lack of information” thing seems more like an excuse than any kind of reasonable approach.

                Having someone question you Every. Single. Time. they are in a meeting or given an assignment is exhausting. This isn’t questioning like “where is the old file cabinet?” It’s “so, like, why are we filing things again? Why is the cabinet in the corner? Why does this file go in that cabinet?” And for no other reason than curiosity and it might be useful.

                The problem may only be with a single team member, but I’d bet everyone has noticed this. If this one person is stressed or under a tight deadline (or stuck with doing something where the reason is “because a VP made this decision and it’s stupid, but whatever”), responding to an endless series of pointless questions would probably make her look flustered or defensive because of trying to find a diplomatic way to shut it down without introducing more questions.

                1. Not Me*

                  Right. Which is why I said the time and place of the “why?” matters in previous comments. I think telling someone to just “wait and see if they figure it out” isn’t the best approach for someone who needs more information to get going.

                  He asked how to best ask his questions.

                2. sunny-dee*

                  He asked how to best ask his questions.

                  And that is not the right question to be asking. Probably 90% of these questions shouldn’t be asked at all.

              2. fposte*

                “How does anyone know if his thoughts are useful if they don’t consider them?”

                But that’s not how workplaces work–you could also say how do you know that everybody in the company can’t do the CEO’s job unless you try them. The workplace default is to position-appropriate thought contribution, which involves a consideration of the time and effort of everybody involved, not just the question-asker.

                It’s absolutely appropriate to ask some questions, especially when you’re learning. But it’s vitally important for every employee to understand that their individual questions are not their workplace’s priority and that you can ask for too much time and energy for your particular position and questions.

                1. Not So NewReader*

                  Am chuckling. If everyone spilled out every thought they had, nothing would get done. There is a cross-over line where asking too many questions looks like the person is trying to avoid work.

                  Sometimes the answer is “Because of reasons we have to do it the slow hard way. Now, stop asking questions and roll up your sleeves and help us move this one ton delivery of potatoes right now.”

          3. BethRA*

            Allison: “Are you only doing this when you’re heavily involved with a project and really need the context, or are you also doing it more casually, when you don’t really need that context and are more just curious?”

            OP: “It’s fair to say that this is my everyday default setting…”

            That sounds to me like he is plumbing the depths in places where it’s not his job at least some of the time, and that’s going to take a lot of time and energy on the part of people who may not have it to spare.

            1. Not So NewReader*

              If it’s a default setting, then the defaults need to be changed. Very soon.

              1. Quandong*

                Also, the OP’s perception of what ‘amping it up’ for work will be very different from other people’s perception if it’s a default setting.

                Not everyone has the same baseline. From the OP’s description I would find their questions exhausting and intolerable because my baseline is so different from theirs.

          4. Annette*

            Why would they have hired him for his insights about fixing disasters. He’s not a mobster. They probably hired him for normal reasons. Big assumption.

            1. Not Me*

              That’s one of the assumptions Allison covered in her response. It’s a totally reasonable one. Companies hire people to assess efficiency all the time. It doesn’t sound like the case here, but it’s not outside the realm of possibility. And it certainly doesn’t imply anyone is a mobster.

          5. Princess Consuela Banana Hammock*

            I think you may be responding to arguments that Amber Rose hasn’t made? AR has done an excellent job explaining why the OP’s approach can undermine OP’s own efforts, and her reading of OP’s letter looks accurate to me (i.e., she’s not jumping to conclusions or making broad speculations about what OP has written).

            OP explicitly wrote that he asks questions because he’s generally inquisitive and curious. He also asks questions relevant to his job, but it sounds like he’s asking a lot of questions that have nothing to do with his work or work product. This isn’t about diversity of thought or thought process—it’s about understanding when and how it’s ok to ask work-related questions of others (including senior folks) in most workplaces. It’s important for OP to hone the when and how skills in order for OP to be successful going forward.

            1. Not So NewReader*

              Some questions can be answered just in following the process through to it’s conclusion. There is an expectation that one should wait to see how things unfold.

              I remember a friend talking about visiting relatives. Relatives were from the mid-west, where the view is huge, long stretches of road where one could see for miles. The relatives could not get over the hills and curves here in the NE. With every hill or curve they would ask, “What is on the other side?” After asking this question way too many times, finally someone explained that we do not ask that question, we just patiently wait and see what is on the other side and that is part of the enjoyment about the ride the surprise of finding out what is around the corner or over the hill.

        3. Washi*

          Exactly. As far as I understand the letter, the OP isn’t asking about things because otherwise she can’t get her work done, she’s asking because she is curious and suspects she could do better. I am also that type of person – I am very organized and tech savvy and efficient and have improved processes in every job I’ve been in. But you HAVE to know the time and place for that, because it is a very thin line between “eager with fresh eyes” and “naively overstepping with patronizing attitude.”

    2. Falling Diphthong*

      I’ve learned that a good number of my questions will be answered if I just go through whatever the task is. After a few rounds, I’ll make up my own checklists and quick answer form for that particular task.

      1. lawschoolmorelikeblawschool*

        Yes! It took me a few years of working but now I try to see what I can glean on my own before asking questions. Obviously this is different if something is on a super tight schedule, and there is no time for me to figure it out.

      2. Sylvan*

        Same here. If you want to know why people do X before Y in Z process, usually watching or doing Z yourself will answer your questions.

  5. Some Sort of Management Consultant*

    My current project manager had been training me in something adjacent to this: letting things go and accepting I can’t (and shouldn’t) know everything all the time. That it won’t work to keep track of every little detail in all parts of a project when I have my own areas of responsibility to tend to.

    And goddammit, it’s a hard habit to break. (I’m still fairly junior, 4 years since graduation.)
    In my case, it’s also linked to a need to appear smarter than the others in the room, dazzling them with my brilliance so to speak. (At least I’m aware of it ;)) and that’s an even harder habit to break.
    Is that something you recognize in yourself, OP?

    1. Falling Diphthong*

      I had a series of phone meetings where two people stood out–senior to me, on the same level as each other in terms of job title. When Susan started to ask a question I would inwardly cringe, having learned that it would swirl into a long involved detour while people (sometimes including me) tried to explain basic things she seemed unable to grasp. When Miranda started to ask a question I perked up and paid close attention, having learned that it was likely to be an excellent point that would substantially shape this aspect of the project.

      Knowing whether one is Susan or Miranda is a reflective view I’m not sure many people have. But I will say that in a given meeting, Susan probably asked a lot more questions.

    2. Original Poster*

      OP here!

      Your last paragraph resonated with me so hard. I recognize my urge to demonstrate my thoughtfulness, intelligence, and helpfulness, and only now do I see that this questioning habit is an extension of that. I think a “show, don’t tell” approach is probably the way to go here.

      1. KimberlyR*

        I also have this failing. I get new ideas quickly so I often jump into asking for explanations, blurting out possible solutions, and otherwise being the kid in the class who raises their hand first and shouts, “Me Me Me!” I have to consciously hold back and listen to others’ contributions. I also ask for explanations but a lot of times, I’ll phrase it as, “I know we are doing it this way. Have we thought about that way, or is this something that hasn’t worked before?” But I also wait until we’re not in the thick of things, or not in a big meeting full of people who don’t want derails, etc. You can still have big ideas and big contributions. But you can also actively listen before speaking or questioning.

        And for the one frazzled coworker, I think its worth having a conversation and letting her know you aren’t questioning her or her actions, just seeking to understand. Maybe you can give her permission to let you know when its too much or she doesn’t have time to stop and give you the play-by-play. Hearing that you’re ok with that will probably cut down on her frustration and she may be more open to giving more context in the moment.

      2. Dust Bunny*

        I mean this in a friendly way: Realize that this urge is about you/your needs more than it is about the work/your coworkers’ needs. Proceed accordingly.

      3. Some Sort of Management Consultant*

        Oh, I’m so glad it was useful for you! It’s something I’ve realized about myself just in the last few months (well, I knew it already but I haven’t been able to verbalize it) and it was such a “whoa” moment for me!

        “Show, don’t tell” sounds like an excellent summary of what we both need to practice! :)

      4. Not So NewReader*

        This is yet another reason why too many questions is not good. It does read as insecurity, as a struggle to show others one’s worth/value. So other people do see that you are trying (perhaps) too hard to show your value. It’s not a huge leap in logic for them to conclude that you are not sure of how you fit in or whatever.

        A good way to show value is through offers of help with specific things. You know Mary is running late on her reports, so you can ask her if she would like assistance with some of the preliminary work which would free her up to concentrate on the report itself. And I would say it that way, too, “I can pull preliminary stuff A and B over here to free you up to concentrate on the rest, if you would like.”
        I have even done this with new-to-me bosses. It’s a nice way for the boss to get a feel for the scope of the work I can do.
        Don’t do it all the time and don’t do it at predictable intervals. Keep it random and casual.

      5. TK*

        Hi OP, good to recognize that. I think often asking too many questions can actually get in the way of wanting to look smart. It demonstrates social tone-deafness and a lack of consideration for other people’s time, plus the questions themselves can be dumb if you’re asking about an area of business you don’t know much about.

        It’s better to be known as someone who contributes only when appropriate, and when you do (infrequently) ask a question, it’s a zinger that gets people thinking about something important.

  6. It’s A Bird, It’s A Plane, It’s SuperAnon*

    I appreciate Alison’s script here. You’re acknowledging that you ask a lot of questions in the moment and asking if it is a problem. But I wonder if most people will answer “no” to be polite, and if asking a mentor or your manager is a better course of action, because they can give feedback without having to explain or defend their own reactions.

    As a new team member, would it make sense to set up a time to ask a mentor to team lead all of your context questions at once, rather than peppering them into every request?

    1. Slow Gin Lizz*

      “As a new team member, would it make sense to set up a time to ask a mentor to team lead all of your context questions at once, rather than peppering them into every request?”

      I was coming here to say just that. And if you’re asked to do a task and stumble across a step of it that doesn’t immediately make sense to you, you can sit on it for awhile and see if it makes sense after a day or two. Just make sure if you continue doing the task you don’t make any irrevocable changes based on something that doesn’t make sense to you.

  7. KHB*

    Could it be that the questions you’re raising and perspectives you’re introducing are things that had already been discussed to death long before you got there?

    Because you’re the new guy. Even though the team as a whole is pretty new too, the other people have been there longer than you have, and they probably know more about the job than you do. It sounds like you’re not asking for this information for your own understanding, but because you think you’re raising ideas that nobody else has thought of before. And that might not be a safe assumption.

    1. Slow Gin Lizz*

      Agreed, KHB. OP, if you want to be sure you are not annoying people in this kind of situation, you might want to consider starting your questions with “Have you discussed this before?” or something along those lines.

      Oooh, but not “I’m sure you’ve discussed this before…” nor “I don’t know if you’ve thought about this…” (two sides of the same coin, really) because, IMO at least, those two phrases can easily be thought as condescending by the listener.

    2. Not So NewReader*

      OMG, yes. Back to my experience training people. I can tell you for a fact that if you think of it so have the previous ten people before you. So if a person trains a lot, answering the same questions over and over from each person can get a bit tedious. I always appreciated people who used the wait and see approach. And it seem to me that those were the people who caught on faster. I think in part because they kept their thinking in the current moment. They were not seven steps ahead of me trying to figure out how step number 9 would work out and missing what I was saying about step number 2.

      I was really surprised to learn just how often people ask the same questions, with no way of knowing that others have also asked. I developed a habit of working these FAQs into the way I trained.

  8. Curlykat*

    Recommended reading: The Four Tendencies, by Gretchen Rubin. It will help you understand your Questioning Tendency (and others), and how to work better with others of different tendencies.

  9. Dust Bunny*

    Short answer: Yes. Odds are good that you’re annoying your coworkers.

    Honestly, this sounds exhausting. I don’t think your coworker is flustered because it hasn’t been thought through; I think she’s sighing internally at having more of her time and energy sucked away by your NEED TO KNOW. (And that’s from somebody who likes context and whose job is research-ish and thus actually involves finding context for things.)

    The thing is, 1) this sounds like you assume that nobody else has ever thought this through, which is insulting, 2) you assume that even if it were thought through to the ends of the world, it could somehow work differently, which is not always the case, and 3) you think you should have a say in how it works/you think you can “save” the situation from a subpar process, which . . . see #1.

    I’m in a sub-professional position in my department, so there are a lot of things–most things–in which I have no say. I ask for context *if it will help me complete a task* but otherwise I let it go because my supervisors are busy enough as it is. You don’t always need, nor are you necessarily entitled to, the Full Story.

    1. Dust Bunny*

      I’m remembering the Ask Why letter a few months ago:

      My reply there still stands: Intensive questioning shifts the burden to provide an answer from you to your boss/whomever you’ve asked, and that can be unfair and out-of-touch. If you need this information to do your job, then ask what you need. If you’re doing it to scratch your Questioning Itch, stop, or at least curate your questions and do it later at a time when you and your supervisor can agree on a time to meet and discuss.

    2. Dust Bunny*

      I hope this doesn’t double post: I notice the “ask why too much” letter is linked below. My reply to this is the same: Intensive questioning shifts the burden of providing an answer from you to your supervisor/whomever you’ve asked, which can be unfair and out-of-touch.

      If you need the information to do your job, ask what you need. If you’re doing it to scratch your Questioning Itch, stop, then consider and curate your questions to ask your supervisor at a mutually-agreed-upon time.

    3. TootsNYC*

      I sometimes feel insecure about whether I really am an expert in my field, and the times I reassure myself are often the times when I instinctively DON’T do something a certain way (because I know that it’s filled with landmines), or when I ask for something extra to be done (I asked someone compiling stuff from back issues to record photocredits, issue, page number, and something else, and I got all kind of pushback from her and all the other people. I didn’t quite have the capital to just say, “Do it or else,” but I made my case (“we may find ourselves needing that info”) and they argued we wouldn’t.
      Believe me, when we did, I decided I had the political capital to go to them all individually and say, “I told you so.”

      We wasted SO much time on their pushback and questions, “but WHY do we need it?” and then SO much time when we had to get it after all.

      So even when someone is new, part of expertise is knowing the likelihood that one method or another will be successful or not, and making decisions based on a huge bank of knowledge that’s so deep it’s almost instinctive.

    4. cmcinnyc*

      On that “sub-professional” note–I’m an EA and I am the buffer between my dept and the bureaucracy. There is a lot of red tape and nonsense I have to cope with it. Some of it for good reason. Some of it really should change. But I can’t change it. And neither can you. So we work with it. And the best way to do that is to just DO IT, not argue about it.

      1. Dust Bunny*

        A huge amount of what I do is hog-tied by industry standards. And they are there for good reasons (so the format of our work meshes with that of other institutions), but they are not always intuitive. I need to know a) what they are, b) how to use them, and c) that they are not negotiable. Knowing the history of them might be interesting but it’s not necessary, and it’s definitely not necessary when we’re busy and pressed for time. I can ask about them, sure, but some other time.

        1. Seeking Second Childhood*

          Good lord yes… sometimes my depth fields the same questions many times in a row, pretty much asking why we need to be considered in the production schedule, and the answer is right there on page X of the UL standard that we must meet to be allowed to sell our product.

    5. anon today*

      My husband used to ask why because he assumed that no-one else (that is, me) ever thought this through and that if he thought about it, thing would be different. Since we had the time and space and love and commitment to hash this out, we did, and now he approaches questions differently and isn’t so insulting :) after some spectacular fails on his part.

      On the other hand, I had a coworker who genuinely was wonderfully curious but derailing. I’m giving a presentation to 14 people, and she’s the only other technical one: she asks something that ends up equivalent to, “Why is that the definition of entropy?” Entropy/its equivalent here is just an equation for an industry standard, one way of doing things, not the only one. I start flashing back to quantum mechanics in college and answer, “You know, I’m not prepared to answer that at this time. We can talk afterward.” She follows up: “well, can you give an intuitive idea for why that’s the definition of entropy?” …….. .. “No.” Remember, 13 other non-technical people. 20 minutes left. I’m not prepared to give a pop science lecture on entropy. We’ve got other stuff to cover. I really had to shut it down :( and felt rather bad, but also quite exasperated because she didn’t want to let go!

    6. Not So NewReader*

      I can promise you, OP, that every place you work will NOT be working at maximum efficiency. Matter of fact, they will probably be far from it. It’s good to dial back that expectation.

      Once I am in place a while, I spend any capital I might have on safety issues or on the worst of the worst inefficiencies. That is how I pick my battles. Places are paying us to get the work out IN SPITE of all the things that are wrong.

    7. Aerin*

      Late reply, but yup, exhausting is the right word. Explaining the reasoning behind something takes time and energy, and figuring out *how* to explain something can be challenging, especially if you’re put on the spot. And double especially if you’re not the one who made the decision so you don’t even have the answer yourself! Honestly, after 2-3 times of this I would start actively avoiding the person if at all possible.

      Plus, it puts me in mind of a lot of non-work conversations where people demand a lot of context, which is also a no. Google is a thing, if you care *that* much about going in-depth do the legwork yourself. I did not volunteer to be your research assistant or trainer.

  10. JobHunter*

    If I were the person being questioned, I would also be watching for signs that you are digesting the information given to you. Sometimes people half-listen and ask for answers that have already been given.

    1. Jane Gloriana Villanueva*

      Great point. OP, I think Alison’s answer is great to help you realize there’s no one size fits all answer, and so much of it depends on context (and a different office = different context, so this could be very different in a new job!). But do be aware of what JobHunter brings up. I started to add more details verbally and in email so that my employee who asked ‘why’ *all the time* would have more and more context as appropriate, but he clearly doesn’t pay attention to my provided answers all the time, especially if they are written down — which is super frustrating to me because I try to have it written for him to refer back to if it is a complex case.

      Once, I solicited his opinion and then told him the choice and why, and unfortunately he really took it personally that I hadn’t chosen his suggestion. I wanted him to have input and I did consider it, and I explained why [this was at a time when he didn’t consider the bigger picture], again in writing, but then his answer was a flippant, hurt, “You don’t have to explain all your desicisons to me. You’re the boss.” If only he abided by that with every OTHER decision (haha), but this one particularly mattered to me because I wanted him to learn my thought process and the larger framework to be prepared for similar future inquiries.

      With your coworkers, definitely strive to make sure you are digesting the information provided and accepting the feedback. You can and should ask ‘why’ but you need to make sure your work demonstrates you’ve absorbed it.

  11. Allornone*

    I feel you, OP. I was kind of like this at a former job. Most of the time, it didn’t present a problem because my bosses knew I just wanted to have a firm grasp of the work, but one particular manager always took it to think I was challenging her decision process. I really wasn’t, but she couldn’t see it another way. I learned to tone it down a bit when dealing with her, only asking needed to know and really framing my language in essential questions to ensure she understood I meant no disrespect. It still wore on me, though (ow I think I might not ask things enough) But yeah, be careful who you phrase things, and work to watch your tone. And maybe ease on questions. It seem oddd, I know, but you really don’t need to know everything.

    1. TootsNYC*

      there’s also the “Someday, I’d like to get you to share your decision-making process; I think I could learn a thing or two.”

      1. Allornone*

        Exactly! I used one a couple of times with success. I felt for the manager. Her bosses didn’t give her the respect they deserve which probably what played into her being defensive with me. Learning to understand and work with that was a learning experience and has become a go to story for job interview questions concerning conflict

    2. Not So NewReader*

      Ugh. One place I worked the load tolerance was ONE question. If I asked a second question, I would see the upset starting… I quickly learned to pick my questions very, very wisely. This was in a workplace were the boss was not a strong leader. Boss tried to be friends as well as the boss, and we know how well that works out. Not.

  12. Dee-Nice*

    I was training a temp once who would interrupt me multiple times while I was explaining procedures to ask, “Why do it this way? Why wouldn’t you do (XYZ) instead?” It annoyed the hell out of me and I always wanted to ask her to save her questions till the end of the tour. It doesn’t sound like this is what OP is doing, exactly, but I do wonder how much time could be saved by simply waiting for a little more experience at the job to fill in the missing context when it’s not immediately necessary to know. Then, if you find something that really could be improved, you’ll have had the hands-on knowledge to back it up. Sometimes being new means just going with the flow for now.

    1. Dust Bunny*

      My dad does this. He’s showing off how smart and engaged he is. Never mind that if he would just shut up and listen I’d get to the answer, anyway. It’s really disruptive.

  13. blink14*

    I can see how this would come off as annoying, particularly if you are questioning things that have been in place since before the team was put together. A lot of times, there are rules/procedures/systems in place that everyone knows are stupid, but no one can make any changes to them for whatever reason. Questioning issues like that is probably really tiring at this point, especially for longer term employees on your team.

    I would be straightforward about why exactly you need the information and what you plan to do with it – evaluate a procedure, compare the current procedure to another option, etc.

  14. Luna*

    Asking to double-check you got the information right or that you want to ensure you ask about something before it could become a problem is fine. But repeatedly asking ‘why’ something is this way would bother me. I can understand not being given decent training — I realized on my first shift alone that I was not shown a very *basic* thing that should have been taught to me during my previous two weeks of training. And it did cause problems.
    But it’s just a question of moderation, as with most things. Some questions are okay, but dragging things on with repeated questions will get annoying.

  15. Kateagory5*

    There are also a lot of times when the answer is “That’s just the way we do it here, and any perceived gain in efficiency would not be worth the time & effort it would take to change it,” or, “It might not be the most efficient for us, but it’s way more efficient than the alternative for department B.” It gets exhausting to explain this all the time, especially from someone new who does not have the experience with other departments. It can feel a bit like being attacked, honestly, and make someone a bit defensive if you’re always getting 10 levels deep into why something is done the way it is. Some stuff is just entrenched, for better or worse.

    1. Serin*

      Or “Because Kermit, the Vice President of Sales, insists on it, and we all know it’s nonsense but we have an unspoken agreement that it’s easier to go along than to deal with his endless arguments.”

      1. your favorite person*

        There were LOTS of things in my department that were done a certain way because the President said they were ‘sacred cows’ and people would be upset if they were changed. Turns out, they were HIS sacred cows, everyone else has liked the changes. Sometimes, you just have to wait out leadership changes.

        Regarding OP, I asked a lot of questions, too, but I spaced them out and waited for times that allowed for longer discussions. Then I’d later come back with “you probably already tried this, but what about ___” via email. Then they could respond (if they wanted) at their leisure.

    2. Evergreen*

      Couldn’t have said it better! I have a newish colleague who manages to come into every process and ask ‘why not this way?!’ No, it’s not that i’m lazy and not that i’m an idiot, I can also dream up better ways of doing it – but the cost of changing it just isn’t always justified by the potential benefits

  16. gecko*

    Seems like you are picking up on this specific coworker’s signals that she doesn’t want to talk about work with you this way, for whatever reason. Maybe she feels like all the questions are meant to catch her out in some way, maybe she’s worried about not knowing the answers, who knows.

    I think, no matter whether you dramatically change your working style, you know pretty well that you should cool the inquisitiveness with this specific coworker. It’s not necessary in every situation, as the original answer points out, and with this person it sounds unwanted. You’re getting the signals from her, and I think it would be collegial to pay attention to those signals.

    1. Librarian of SHIELD*

      I agree with this 100%. If you can tell that a thing you’re doing is making someone else uncomfortable, you should stop doing the thing in your interactions with that person.

      That doesn’t mean you can never ask this specific coworker a question ever again. Just that you should be super mindful about what questions you’re asking, why you’re asking them, and the timing of the conversation. You may even find that once you’ve cooled it on the questions for a while, she might not bristle so much when you do come to her with a question that’s actually relevant to the work you’re doing together.

    2. CM*

      I think the gender dynamic the OP mentioned might also be relevant in this specific case. I’ve run into a lot of random male coworkers who seemed to feel like they had the right to interrogate me and decide for themselves whether I was qualified to do my job and get involved in (what they considered to be) their projects — almost like doing another round of interviews after the company already hired me. I’ve had that from men who predated me and men who were hired way after me. I’ve also had it from men whose work had literally nothing to do with mine — usually followed up by condescending comments about how impressed they were. (Glad you approve, random strangers who don’t even work in my field!)

      So, whether or not that’s what the OP’s trying to do here, there’s lots of room for it to be interpreted that way since this is, in fact, a thing that guys seem to do.

  17. Engineer Girl*

    There is an issue that is implied but not directly mentioned. That is the matter of time. Every time you ask questions you are demanding that someone give up precious work time for your curiosity. If it’s for something you are working on then that’s OK. But if it’s for your own curiosity then it’s highly presumptuous and disrespectful of others time. That’s especially true in a startup where there is never enough time.
    I suggest that you request a tutorial on things related to your job. Ask for a time that works for both of you.
    In other things I suggest waiting until you see how the operation works. At three months, you don’t have enough information to be challenging the processes.
    In short, other people are there to do their own jobs, not be a 24/7 walking encyclopedia for your questions. Be respectful of others time by asking questions related to your job. Ask other questions at a time and place that does not interrupt others work.

    1. Dust Bunny*

      This. If you just want to know but don’t need to know to do your work, this is actually really self-centered.

      1. Quandong*

        Truth. No matter what the intention, this is taking a lot of time from coworkers who are trying to do their jobs.

    2. TootsNYC*

      also–if you truly want to learn, try this:

      try to figure out from your own observations what the answers are to those questions you would have asked in the last meeting. Watch as things move forward.
      I even sometimes create a hypothesis (“I think this is the reason/danger/payoff”) and then watch to see if I’m right.

      Later, when there’s more time, you can say, “I was thinking you did X because of Y. Was I right?”

  18. Jennifer*

    Understanding why I’m doing something can be extremely helpful instead of someone just saying “do this” and dumping a bunch of work in my lap. It helps me learn the job a lot faster. That being said, the number of questions can become overwhelming. Also, if you’re new and still learning the ropes, sometimes people who have been there longer can bristle when being asked so many questions because it sounds like you are doubting a system that works for them. Maybe it does need to be improved, but sometimes your questions/suggestions will carry more weight if you’ve been there a bit longer.

  19. Knork*

    If something you’re doing is making a coworker flustered, defensive or otherwise unhappy, and you don’t have to be doing it, you should stop doing it with that coworker.

      1. Hardcore parkour*

        Double-yup. These “flustered” and “defensive” vibes may seem like a subtle hint that maybe something is up that may involve you but you can’t really be sure. To me, she is bonking you on the head with a sign that says “QUIT IT!”

    1. Quandong*


      And if it is something that must be done, find another way to interact with them.

  20. Rusty Shackelford*

    I’ve worked with a couple of people who would say “I don’t underSTAND why we’re doing it this way” when they meant “I don’t want to do it this way,” and would demand detailed explanations that they would attempt to pick apart, looking for a gotcha or a loophole. And even if that’s not what you’re doing, it’s entirely possible that it’s being interpreted that way.

    1. ElleDee*

      I have a questioning nature myself and have to be really careful it doesn’t annoy or overwhelm the people around me. Here’re things I do so that I can information gather in a way that in unobtrusive as possible and improve my contributions to the office:
      – If I have a new process, I try to do that process as instructed before I ask questions about it. Many things become clear as I actually do the task myself.
      – I observe and listen and try to draw connections myself first without taking up the time of others.
      – If I ask “why”, I am as clear as possible that I’m not about to launch into a dissent. I accept that sometimes the reason isn’t great, but there is probably some logic behind it that I need to respect, at least until I have a full picture of all the pieces *and* a plausible solution. Sometimes it’s just “the boss likes the thing to be a stupid way” or “regulations” and that needs to be treated as a prior. Sometimes there’s a long history behind the current situation and people do not want to revisit it.
      – Certain people understand where I’m coming from and see the benefit of my approach, but some people don’t, and changing their mind is not a good use of time. Leave them alone.
      – Be mindful of people’s time. Explaining things requires it, so you need to be grateful for people sharing their thoughts, especially if they are candid.
      – Undoubtedly some things will need to be changed, but new people don’t know what they are yet. Information gather, digest, then propose only your best ideas after you have a good idea of what the impacts will be.

    2. CommanderBanana*

      ^^ Thank you. I have a coworker who would always claim not to understand something when what she meant is that she didn’t want to do it. So we’d end up in this stupid circle of me trying to find ways to explain something that was actually very understandable. It was just that she didn’t want to do the thing.

  21. Ashley*

    As someone who loves context and does ask questions something I have found helpful is to try and frame things, “so I know for next time…” This has helped me get to the root of the info if I feel like there isn’t rhyme or reason and it matters, but I also realized I knew what to do for next time more often then not so I saved asking a few questions that were unnecessary.

  22. Merci Dee*

    This letter brought to mind the posting from last week about the grumpy “that’s just who I am” co-worker, along with the link that Alison posted to the Marshall Goldsmith article about “An Obsessive Need to Be Me.” (link to last week’s letter to follow) It seems like the OP has walked into one of those situations where the need to “be inquisitive” and ask lots of questions might quickly reach the point where it no longer benefits OP or the team if it continues in the way that it has.

    Asking a few questions to clarify an assignment and make sure you’ve got a good grasp of what the assignment requires is always a good thing; asking “but, why?” just because there’s always another reason to ask it serves no one.

  23. Czhorat*

    If you know why then you also know both how to prioritize and which part of a task is most important, and why.

    Context is important.

    1. Dust Bunny*

      Except that it’s not always. If you need to know which part of a task to prioritize, the direct and concise way to find out would be to ask your manager what s/he wants prioritized.

    2. LawBee*

      Getting context is good, yes. Narrowly defining “context” is also possible – to your point, finding out where that task falls in the overall project is good information. But not every single task needs a history lesson of how the workflow got to that point, what the decision tree looked like, every other alternative process that was considered, etc., which is what it sounds like the LW is trying to get. Sometimes you just do the task as assigned and move on.

      1. Ethyl*

        Right! Not to mention that honestly, if whatever you’re doing is annoying your coworkers (humming, bad breath, asking too many questions, standing too close, telling weird long pointless unfunny jokes about cats), even if there’s a super good reason you’re doing it, you really outghta stop it.

  24. LawBee*

    Honestly, I got sympathetic exhaustion just reading your letter. If you think you’re asking too many context-questions, then I guarantee you that you are. And if your coworkers are getting flustered, it means that you’re hitting them with questions that aren’t relevant at that moment, so they’re not prepared to answer them. I would definitely feel challenged and a little put-off if my coworker was demanding all the background behind every process. Sometimes it’s just not worth explaining!

    Maybe set up a lunch date with a coworker specifically to go over institutional/group history (such as it is), and then start practicing asking relevant questions in the moment, and tabling your context questions for later.

  25. boo bot*

    OP, you say, about your colleague’s reaction to your questions: “I worry that she may feel that I’m challenging her in some way.”

    That may be because you are. If you’re asking her to rigorously explain and justify her work and her decisions on a regular basis, you’re essentially asking her to report to you; moreover, that intensity of questioning carries a strong undercurrent of, “prove to me that you didn’t do this wrong.”

    I think your concerns about “power moves” and “man-questioning” are on the mark. You may be motivated by genuine curiosity, but from the way you describe your actions, you may be coming across as more adversarial and less respectful than you intend.

    I would find this exhausting; I *have* found it exhausting when people have done it to me.

    1. LQ*

      All of these points. You are absolutely, entirely, completely challenging her. That is all you’re doing.

      You may think you’re trying to understand, but you don’t have the authority or the time to understand every single tiny bit of someone else’s job, because that job is a full time job. And yours should be too.

    2. Sylvan*

      Yes, that makes sense. You’re trying to show your interest in learning, but you might unintentionally look as if you want coworkers to earn your approval in situations where your approval isn’t really the point. If you think this might be happening, limit your questions to subjects that affect your own work. If you’re curious about someone else’s work, don’t disrupt them; strike up a conversation when you both have some free time.

      1. boo bot*

        you “look as if you want coworkers to earn your approval in situations where your approval isn’t really the point.” This is so spot-on.

      2. Original Poster*

        Thank you for the frankness! I’m a firm believer in the idea that I can only control what I say and how I say, not how it’s interpreted. This specific thread has really connected that idea with my original concerns.

        1. TootsNYC*

          But…this doesn’t mean that you can IGNORE how it’s being interpreted.

          You absolutely can influence how you are perceived, and how the things you say are interpreted. Because they are interpreted IN LIGHT OF how you are saying them.

          Pay attention, and when people are interpreting you as meaning something you didn’t intend, that’s now YOUR responsibility to change how you communicate. Because you’re not being effective.

    3. The New Wanderer*

      This is my reaction too. I strongly believe that the new person’s role is to learn as much as possible in order to contribute most effectively, but first by listening and then by asking the clarifying questions you still need answered. If you’re just barreling straight into questioning everything and everyone, you’re not using anyone’s time effectively, including your own. And if the team’s only existed for 9 months anyway, things are probably pretty fluid still so asking “Why is it this way?” all the time isn’t as helpful as you think to either you or the team.

      Context is important, and finding the inefficiencies inherent in not questioning some existing processes can be a good thing. But it’s really not the role of the newest team member to solve all the problems.

      My favorite suggestions so far are:
      1) limit yourself to 3 or so questions so you have to choose them carefully. Best if you save them for toward the end of a meeting instead of asking throughout, so that people aren’t sighing internally every time you speak up and stop the meeting flow. Do this even if you set up a 1 to 1 meeting with a colleague to find out more about their project – choose your top few questions to kick off the conversation and then let them talk more than you do.

      2) find a mentor, or just someone more senior than you, who agrees to meet with you once a week to answer all your context questions. Personally I have this setup with a mentor and it is incredibly helpful because we can have a really useful discussion about how things work a) without derailing ongoing meetings/projects and b) the conversation is more candid and ‘bigger-picture’ than if I ask each colleague about their projects.

    4. EventPlannerGal*

      I agree, and I think the mansplaining/“man-questioning” element is really something worth reflecting on. The OP says he’s aware of it, but being aware of a concept and theoretically wanting to avoid it does not always translate into our everyday actions. I know that when I picture myself being interrogated in this “but why?” sort of way by a relatively new male colleague who says he ~just wants to help~… nope, not a fan of that concept.

    5. BananaPants*

      OP says in another post that this colleague is his program manager – he is absolutely challenging her and doesn’t even have the self-awareness to recognize it. Regardless of his motivations, this behavior needs to STOP immediately, assuming the damage hasn’t already been done.

      OP is the new guy and he was not hired to be a change agent, nor is he in a leadership position where he actually has power to drive sweeping process changes. He needs to know his role and suppress this compulsion to question everything, and just do his job.

  26. FatCat*

    Yeah, I once had a co-worker from hell who used this tactic as a cover for mansplaining, hectoring and know-it-all-ism. His reputation spread and no one would work with him. You might not mean it that way, but someone will probably think you’re being an @ss because they’ve had that experience before with a questioner. I agree with the advice to step back and think before you ask. Also, if I may suggest, if you represent a group that has traditionally held power in the workplace and society and you’re questioning people who represent groups that haven’t had that privilege, your chances of being perceived as arrogant and annoying just went through the roof.

    1. anon today and tomorrow*

      Yes. This is my experience as I wrote in a comment below. There was someone like this at my last job where we had to add extra time onto meetings and no one wanted to work with him or even give him help because everything would be met with “but why????” only so that he could suggest something that had already been tried.

    2. LabTechNoMore*

      I’m going through this right now with my new coworker, and started seeing red reading this letter. (I’m a guy, but also younger and a PoC.)

      Currently it’s not possible to loop in coworker on any of my projects (despite desperately needing the help!) because they’ve already repeatedly and vehemently have voiced grave concern, unprompted, over how I’m doing my work, from issues ranging from legitimate (slightly more accurate to do it his way, but would take a month to implement), to absurd (very strong opinion over word processor for text viewing documents.

      OP, you really need to cut out this behavior before it damages your reputation amd working relationship any further. With the constant stream of criticism he’s giving about my work to me, and my boss, affecting my credibility on the team, I’ve started looking elsewhere.

    3. BananaPants*

      I have a coworker who turned out to be this guy. His “devil’s advocate” type of questioning was immediate and constant. I don’t know that I’d always characterize it as mansplaining because much of it was directed to other men – including men who were much higher than him in the corporate pecking order. I’m sure he thought he was showing how smart he was, but in reality he just bogged down meetings and alienated peers and superiors because he didn’t know his role.

      As his technical lead/supervisor I counseled him several times on how he was coming across, and he just kept insisting that he was innately curious and “needed” context for decisions that were made when he was in grade school. His project teams started cutting him out of informal group sessions because NO ONE wanted to deal with him and I think our manager celebrated when he finally managed to transfer Annoying Dude into another department.

  27. BRR*

    It’s tough to say for sure if you’re annoying your coworkers without experiencing this first hand but my gut feeling is you might need to reign it in some of the time. It’s great that you want to learn! I have some coworkers who don’t and it’s incredibly frustrating. There’s also the phrasing. You don’t want it to come off as challenging people even if that’s not what you intend.

  28. Not Today Satan*

    I think it’s fair to assume LW is asking too many questions, but I have a more positive interpretation of him than most others here, it seems. When I managed people, it drove me crazy how often I’d ask, “why do you do X this certain way?” and they’d have no response other than, “that’s what I was told to do.” If you don’t understand the Whys of your job, you barely competent, IMO–it can make it difficult to spot mistakes, or concerning trends, and whatnot. I’ve gotten a lot of promotions in a short time and I’m certain it’s because I’ve gone out of my way to deeply understand how things work.

    BUT (big but) when you’re new or low on the totem poll, “why?” questions should be for your understanding ONLY. Working some place for 3 months and asking why questions because you’ve “seen insufficient, untimely, or incomplete information torpedo a project” is a really easy way to become a resented, annoying coworker.

    1. Danger: GUMPTION AHEAD*

      I think there are priority layers to asking the “Whys” of a job and some things are outside of your scope to question. For example, in my job knowing why we classify certain things in the llama tracking system in a certain way is critical to doing the job right. Wanting to know why we track llamas and not alpacas would make me think you didn’t really get the role you were hired for or the mission of the unit. And there are some things that all the “Whys” in the world aren’t going to clarify things (e.g. procurement system, travel requests) because it is a jury-rigged system that is trying to meet the needs of too many different types of programs and kinda sucks for everyone

      1. Joielle*

        I think this is key: “…would make me think you didn’t really get the role you were hired for”

        I’ve had this come up with interns, where I need to hand off a simple but time-sensitive task so that I can do some more involved part of a project. Once a deadline has passed, I’m happy to take as long as necessary to explain every aspect of the project – interns are there to learn! – but at that moment, I really just need them to accept my explanation, do the task, and save other questions for later. Even after explaining in almost exactly those words, I STILL get tons of context questions from some interns. It feels really tone-deaf and disrespectful of my time. I don’t expect anyone to read my mind, but I do expect people to understand their place in the organization.

        I get that people are interested in context, but the nature of a junior role is that sometimes you have to just do the task you’re given.

    2. LH Holdings*

      I firmly disagree with many of these statements. People are “barely competent” if they don’t understand every Why of their job? In so many positions, policy and procedure decisions are make so high above someone’s position they they never truly understand the inner workings that led to those decisions. Does that make them incompetent? No, it makes them a person who is judiciously using their time instead of chasing down every rabbit hole trying to find the elusive “Why?”

      1. Not Today Satan*

        I don’t mean obscure details, but like “I compile this list every week because we have a contract with [basic info about the client/funder/whoever–not necessarily their name] that requires X Y Z information” rather than “I compile a list because a boss 3 bosses ago told me to.”

        1. Danger: GUMPTION AHEAD*

          What about, “I do a purchase order this way (which is an admittedly stupid a cumbersome way) because a boss 3 bosses ago decided to do it this way when we bought the system and now if you don’t do it the system rejects your PO”

          No one understands why it is this way, no one has to power to change it because we don’t have the money, and if you “why” me on this or make suggestions on how to fix the unfixable I am just walking away.

    3. Lily in NYC*

      Ha, I’d love to see you come and try to figure out a part of my job. I don’t understand it, but I do what I’m supposed to and have given up trying to learn it. But I am not “barely competent” for not understanding the arcane red tape of government procurement. Sometimes it’s more intelligent to know when it’s ok not to understand something.

      1. Danger: GUMPTION AHEAD*

        I’m cracking up that both of us came up with procurement systems as the ultimate, unexplainable, puzzles. We handle a lot of federal, state, local, and foundation grant money plus private donations and our system works (after a fashion) for all of them, but is not optimal for any of them

        1. Lily in NYC*

          I laughed when I saw your comment as well! I manage compliance for government contracts, so you can imagine what my job is like. I love your username.

  29. Probably Nerdy*

    So many questions here seem to follow the same format: “I do something unusual and people sometimes act annoyed by it. I don’t think I’m annoying. Am I annoying?’

    If you have to ask someone if you are annoying, then yes, yes you are. And yes you should stop.

    1. Name Required*

      Asking context for processes is really not an unusual behavior at all.

      I’m not sure this is a fair reaction — just because a coworker is annoyed doesn’t mean that the coworker is having an appropriate reaction. There are lots of reasons why an outside perspective can be helpful.

      1. Former Young Lady*

        Certainly, but anyone who’s been to grad school remembers That One Classmate who asked lots of barely-relevant questions to show off how sharp and inquisitive they were. It wasted everyone else’s time and turned participation points into a zero-sum game.

        It is just as frustrating in the workplace when someone who’s supposed to be in “learning mode” is so eager demonstrate their unique knowledge. An outside perspective ceases to be helpful when the person sharing it has no inside information yet.

        1. The New Wanderer*

          Or the new coworker comes in with a Disruption Mindset, like they alone have the unique ability to ask why something is, instead of learning first how things are and asking questions later about why, if it’s relevant.

        2. Please No More Meetings*

          Oh man, boy do I ever. There were always long discussions at dinner about who That Guy (usually That Guy, but occasionally That Girl) was in your [whatever subject] class was. The best was when That Guy walked into your dining hall and you could FINALLY point him out to your roommates and they knew him as That Guy, too!

        3. Name Required*

          Yes, but I’m not seeing evidence for this in the letter and a lot of these comments (like yours) are coming across as projection. What we know is that OP joined a new team that is making a lot of policy and procedure changes as they go, OP has been burned at past jobs when context was left out of the picture, OP feels like they do a better job when they understand context, and OP is an asker not a guesser. Asking questions and asking for context is what OP feels like he need to do to do a good job, it isn’t about showing off.

          The “type” of person you’re describing typically isn’t self aware enough to know that they are annoying people, or ascribe it to that person having a negative reaction to their awesome knowledge. OP is recognizing that his coworker is reacting negatively and wants to know if that’s on him or coworker, and how to adjust his behavior.

          But regardless of whether your feel like your comparison was fair or not for OP, Probably Nerdy was making a blanket statement that if have to ask if you’re annoying, you’re being annoying. That’s not helpful or true advice.

          1. Allonge*

            OP is an asker not a guesser
            Yes, and of course this has an impact. However, it is a preference and not an excuse.

            I am a guesser, and yet I have to often s*ck it up and ASK already, even if I hate admitting that I don’t know something.

            OP needs to learn to guess (or go without an answer), as he is overdoing the asking. Overdoing almost anything is or can be pretty annoying.

          2. Former Young Lady*

            Your point about ask/guess cultures is well-taken. (I wish companies would test for THAT personality dimension rather than the woo-ier Sorting Hats they like to use these days!) When I first read about ask vs. guess, it rocked my world. I still tend to deal in hints rather than anvils, and that admittedly colors my perception of interactions.

            OP’s response below definitely suggests more self-awareness than many of us gave him credit for, and I think that will work in his favor.

            I am going to push back just a little on the “projection” angle, because I think a lot of us recognize ourselves in his description of the coworker whose face clouds over when the questions start. But, further to your point, OP seems with-it enough to notice the reaction, to seek advice about it, and to take that advice. He calls it his “default” setting but doesn’t seem to be using that as an excuse not to learn. I confess that I’ve got some warm-fuzzies right about now.

          3. Joielle*

            Asking for context is what OP FEELS like he needs to do a good job, but the reality is, OP can probably do many tasks without understanding the whole backstory. Having context is OP’s preference, not a literal requirement for most things.

            I agree that “if you have to ask if you’re annoying, you are” is not always true, but in this case, OP is being annoying.

  30. Amelia*

    Offhand, I can probably think of 10-15 inefficient practices at my company that I’d love to see examined and updated. But I can also think of many more practices and procedures where we just needed to pick something and stick with it. So we run Salesforce, not Hubspot. We can expense $20 things without the receipt but not $25. Our brand guidelines are X, Y, Z. Not everything has an intense backstory. Having certain things settled and clear means we can free up space to focus on client needs, creative solutions etc. If a new colleague asked me to provide background and color on a specific client strategy, that could be valuable for both of us. If he frequently asked me to explain things like why our corporate logo is a dolphin instead of another animal, I’d find it annoying and frankly, reminiscent of my toddler.

    1. Falling Diphthong*

      One of the disillusioning realizations of parenthood is that your toddler asks “Why?” not because they are boundlessly curious about the entire world and surely destined to win a Nobel prize for it, but because “Why?” is a simple adult attention button that they can push over and over.

      1. Quandong*

        Asking ‘why?’ is a time-honoured method for getting attention, not only for toddlers.

    2. LQ*

      I think this is a great point. Sometimes you need an answer and you could spend a decade making the exact right decision that is woefully out of date and entirely irrelevant or you could make a decision that’s imperfect and move forward. I work with a lot of people who want every decision to be perfectly vetted beyond reason and with everyone agreeing 100%. And they never get anything done. You don’t want to be the person who wants perfect over existing.

  31. Bex*

    I’m super inquisitive by nature, and I feel like I’m more effective when I understand the big picture, so I get where the OP is coming from. But it sounds like the OP might be derailing other people’s meetings/agenda’s by asking questions that don’t necessarily benefit the whole group.

    When I started a new job about a year ago, I spent the first 6 months in listening mode. But I also had regular check-ins with a couple peers, with the explicit purpose of bringing me up to speed. In those meetings, I got to set the agenda and it gave me space to ask all my questions and dig into background at a time when it wasn’t impacting my team’s productivity. I usually kept a running list of questions during other meetings, and then tackled them at my one-on-ones.

  32. GreenDoor*

    Ask context questions *when the answers are relevant to you performing your part of the task well*. Otherwise you’re just wasting time. As a manager, I just need a task done, I don’t have time to edcuate you on the whole History of Everything every time I ask for something to be done! I might even find myself grativatating towards the employes that’ll just take the ball and run with it and avoid employees like the OP that make every assignment way more work. Which isn’t fair to anyone!

    That said…I would hope that people would approach me at a quieter time and say, “hey I was curious about….” when I DO have time to provide more context. Other times, it’s actually more efficient to work through a task first – many questions may get answered just by getting the work done. And like others suggested, some questions may be better posed in an after-task review where the whole focus is discussing what worked, what didn’t, what has been done in the past, and new ideas for going forward.

  33. RachelM*

    You don’t mention your level of experience in your post – just that you’re new to the team – but your second paragraph suggests that you might not completely understand your own motivations. As Alison said, unless you were specifically were brought in to address process-oriented issues then what you’re doing is a power move to keep questioning things that are in place, even if they are newly in place or decided “on the fly”. It changes the focus of attention from the task/project at hand back to you and your questions about how/why things are the way they are.

    We have someone like this on my team right now, and it’s exhausting. Nearly every meeting is derailed by a why question. She’s been here well over a year and she still seems really really new, unprofessional, young, and naive. It might feel like asking these questions makes you seem more expert than your colleagues, but needing to know everything often comes off as a sign of immaturity. You don’t have to ask every question at the moment you think of it, and if you find yourself thinking you’re annoying your co-workers then you likely are!

  34. Secretary*

    I am totally like this, I want to ask why about everything I do, ESPECIALLY in a new job. This may or may not be helpful to the OP, I have a certain way that I walk into a new job that has helped me with this a lot.

    For the first 30-60 days or so, I do everything exactly, EXACTLY as my predecessor did it. If my manager lets me know I have flexibility to change things up, sometimes I’ll even say, “I hope you don’t mind, I was going to do everything the way Susan did, at least for about a month so I know why she does it this way.” Most managers are thrilled at this, and if they’re not then I scrap the rest of this.

    After 30-60 days, I usually have ideas about how things can run more smoothly, and will begin to ask questions like, “Why do we do it this way?” or “Would it be ok if I changed this process and do X instead of Y, because it will get done twice as fast?”

    Most of the items I see within the first 30-60 days that would be good to change are actually being done the way they are for a reason. By giving it some time, I’m able to discover WHY without asking about it. That just leaves the items that I need to ask, and I come off as being innovative, instead of annoying.

    1. sofar*

      That’s what I do, too! Not only does it help me see that there are reason the company or team does something a certain way. But, you have so much more credibility if you DO want to change/question things if you’re already familiar with the existing process.

      Sometimes, early on, I’ll ask for context, but big-picture stuff, but it’s always always always tied to my immediate ability to do a project.

    2. Baby wipes and duct tape*

      This so much if you don’t know the process on something asking all of the “curious” questions makes no real sense because they are just questions for being questions if you don’t have a way to use the answers.

    3. Aurion*

      Yes, this was what I was coming to suggest.

      OP, I have been the newbie who (wanted, sometimes did) asked why–and have been right in that The Way Things Were Done was inefficient or wrong! More frequently, there was nuance in The Way Things Were Done that weren’t evident to me, and explaining the whys and wherefores was going to take a significant chunk out of everyone’s time…but in time, I intuited why myself. I try to pay it forward by explaining why of my own volition when I train people, but I think there will just be a lot of This Is How It’s Done in any workplace.

      So unless you were brought in to be an agent of change, OP, spend the first several months listening more than you speak. Ask questions about how–ones directly relevant to your own work so you can do it correctly, but don’t question why in the early days. Sometimes why will be self-evident once you have more experience. And if not, well, after a few months of good solid work you’ll have more political capital to spend on asking why without it being so much of a power play.

    4. Librarian of SHIELD*

      This is a really good way to go about being the new person. I’ve seen a lot of people crash and burn, especially at a supervisory level, because they wanted to rush in and put their own stamp on things before they really understood the organization or their place in it. Taking some time to get to know the situation before you shoot off a list of questions or suggestions is a really good plan.

    5. Yorick*

      This is a great strategy, but for some jobs this period needs to be way longer than 2 months. Sometimes you won’t come across all the parts of your job description within that time.

  35. Lora*

    OP, here is what I would recommend, since you are early in your career: Go to every seminar and read everything you can and before you ask why something is, Google it no matter how elementary that sounds. It’s crazy-making to have someone asking you Why Why Why when the answers are easily Googled. I generally expect that new people will research things and then only ask a human when they’re stuck – people are mostly very busy and don’t have time for Why We Do That 101. There are trade organizations, regulatory guidance documents and industry standards for a great many things, and they will help you understand why some reasons are set in stone and immutable vs. what might be more flexible and readily changed.

    But yeah, it is quite annoying for someone to pepper you with 40 questions when you have other, much more urgent/interesting things to do than educate them, especially when the answer is readily available online. Moreover, it suggests that you’re not really able to use a library or do research online effectively, that you don’t know how to search information out for yourself when you need it. People mostly don’t mind pointing you in the direction of where to find more information, but spoon-feeding information gets tiresome real quick.

    1. Original Poster*

      I’m new to the company, but have been building my career for the past decade.

      I should take it as a sign that you assumed I’m younger than I am (i.e. should have grown out of this behavior). But here I am asking for help :)

      1. Beth*

        Oh man OP, I definitely assumed you were maybe 22 or 23 from your description of your behavior.

      2. Observer*

        Yes, it’s a sign – it REALLY doesn’t come off as the behavior of someone really experienced.

        But asking for help *IS* an excellent move. So there is hope yet :)

    2. Allonge*

      This. I really appreciate it when someone at least makes an effort to be self-driving in finding an answer. Ask: really interesting project – can I read/find documentation on how it started etc. rather than: WHYYYY was it done LIKE THAT? You will have a lot better questions after you have done it / read up all about it, too. And if you learn how information is preserved in your organisation, soon enough you won’t have to ask even that.

      You are new – now is the time to ask all the questions, in principle. But there is only a limited time for anyone else to answer them. Self-sufficiency should be the goal of your questions, not sheer curiosity.

    3. Rebecca1*

      Yes! I am someone who loves answering questions at work, but I vastly prefer to answer them when the asker has at least tried to research them first.

      When you have a question that is not time-sensitive, one good way to ask it is “where would I find out the answer to this?” Then the responder can simply point you to the documentation, if it exists, or choose to answer the question themselves, but they are much less on the spot. Of course you also should wait for a less-busy time to ask something non-urgent.

  36. MuseumChick*

    This is not going to come across as inquisitive. It’s going to come across like you don’t trust your co-workers and/or the company. Are you by any chance in your early 20s? I find this in a quality I find a lot in people fresh out of school. School teaches you to be inquisitive and ask a lot of questions until you understand something. At work, well, it doesn’t work that way most of the time. I am not going to sit there and explain to you all the office politics, judgement call, best practices of for the field, etc that when into my making a certain decision.

    Sometimes the reason something is the way it is, well, it not something a co-worker will want to discuss. Maybe Best Practice in there field say do it A way. But they know doing A way will upset Jane for X reason. B way could work, but the CEO has made in clear in the past the he hates format B. Then there is C, that will take longer and won’t be as good as A so you end up with some hybrid system. None this is anything your co-worker would want to communicate to you.

    Here’s the thing, while our personalities don’t disappear when we are at work we are expect to reign them in to an extent. I swear a lot outside of work but never at work. I have a dry and sarcastic sense of humor. I tone it down at work. I think you need to tone down the “But WHY?” part of yourself a great deal while you at work.

    1. Original Poster*

      I’m in the age-doesn’t-matter-and-time-isn’t-real phase of my life, but my driver license says I’m in my 30s.

      1. Penelope Garcia’s glasses*

        You know, if you have a habit of asking a lot of questions then it’s good to get into the habit of being straightforward when you’re the one answering.

      2. e271828*

        You are old/experienced enough to know how to listen and observe to deduce context. If you cannot do that, you had better learn to.

        (NB: Listening and observing, then thinking about what you are hearing and seeing, doesn’t involve continually asking for context.)

  37. anon today and tomorrow*

    Wow, did this part get my hackles up: I’m inquisitive by nature: I always want tons of context and I tend to ask a lot of questions that boil down to “but why is it this way?” This is innate in me.

    I’ve had so many men use the “I’m inquisitive by nature! I want to know why!!” as an excuse to mansplain, whether they were aware of mansplaining or not. Which of course made me defensive because every “Why?” felt like they were indicating they knew better than me or that clearly I had never thought of a solution they were so ready to suggest.

    I’m sure you don’t mean it this way, OP, but there’s a chance it’s coming off this way to your coworker. There’s a time and a place. One “Why?” isn’t going to raise hackles, but if you’re asking it everyday, as you mention, and using it as a way to make sure nothing slips through the cracks, it’s going to come off as challenging everyone else on the team.

    Especially since you’re new. Unless you were hired for the job of making sure nothing slips through the cracks, it’s only going to make it look like you don’t trust anyone else to get their work done.

    1. boo bot*

      Yes, so often in this kind of dynamic, “Why? is not-so-secret code for “I’m going to prove you don’t know what you’re talking about.”

      I have had so, so many men do this, and the OP should dial it back because even if his motivations are 100% altruistic, a lot of women will interpret what he’s doing as an attempt at the above.

    2. Joielle*

      Yes! Especially because “I’m inquisitive by nature” often comes with the barely-unspoken corollary – “and the rest of you are a bunch of incompetent dullards content to do the bare minimum.” Even if that’s not what OP is thinking, that’s how it can come across.

      I’ve had interns like this before, and after fielding dozens of “BUT WHY” questions about simple tasks, let me assure you I was not impressed by their inquisitiveness.

  38. notanexpat*

    This kind of question was often on my mind when I was new in a kind of general “program assistant” or “associate” role with several managers or no particular workstream; I didn’t know exactly what to do, or what would make me valuable to have around, but I was worried about not being useful, so I tried to get a wide-ranging view of every task I came into contact with to see if that was it.

  39. Tammy*

    My (neurodivergent) brain likes to understand the big picture, so a script that’s worked well for me is to say something like “I’m really interested in how this tool alignment work I’m doing fits into the larger need to be more efficient in our llama shaving efforts. Would you be willing to take a few minutes sometime and help me to understand the larger context?” This is less of a problem for me now – I’m a mid-level manager, so I’m responsible for understanding the larger context a lot of the time – but questions like that helped me earlier in my career to tease out the big-picture info while communicating that my intent was curiosity and learning and that I was respectful of the other person’s time.

    1. [A Cool Name Here]*

      I’m with you – I almost cannot work without the big picture. I am not a “put the nugget in the slot” person. I need to know why.

  40. CaliCali*

    Yep yep yep. I was guilty of this when I was younger, because since everything was a new idea to me, I wasn’t thinking about how these thoughts and discussions were likely not new to everyone else. And being the “person who asks lots of unnecessary questions” isn’t really the title you want to have.

  41. CatCat*

    It’s good that OP has some insight into this and that it is annoying people. I have a coworker like this and the questions come across as challenges and like I have to explain myself (I do NOT). I’ve gotten better at deflecting it. “That’s just the way it is.” “That’s how it was when I got here.” “That’s how I was trained to do it.” But it can be exhausting. I kind of “get it” about the coworker now and that it’s not necessarily really a challenge though it feels that way at times.

    I have another sorta new coworker (former employee, rehired, but our time did not overlap) that started in a similar manner. I was starting to feel kind of prickly and I am sure that was coming across. That person deployed language similar to Alison’s script and that REALLY helped our communication.

  42. Jamie*

    This is funny as I am going through the same thing atm, except I was brought in to improve the QMS system so I’ve been doing gap analysis’ since I started.

    Even when your job is literally to ask people to walk you through their processes and explain the nuances of how and why they do what they do tone is really important. I make sure people understand I’m seeking to understand how things are currently done and work with them to find ways to improve their process.

  43. Has an OP in her professional life*

    OP, I love your inquisitive nature and would love to get lunch. In a day-to-day workplace context, I definitely want ot answer all of your questions and will value your detailed mind. But it’s just that if I do, I will be working overtime, not sleeping and/or not getting my project work done. Me getting behind on my work because a new colleague has lots of questions had happened before. I don’t like it, because I feel like my time isn’t being respected.

    I love an inquisitive nature, but it definitely makes meetings take very long. If you’re in a meeting and talking more than the leader, that’s not a good sign. If people look at their computers when you talk, also not a good sign.

  44. Not One of the Bronte Sisters*

    I think a lot of you are ignoring that OP’s team is “making policy and procedural changes on the fly.” If that’s the case, I think background and context are absolutely essential. OP is absolutely not there to blindly go along with “the way things always have been.” OP, I think I would like working with you, because I am very much the same way. I am a lawyer, and have spent much of my career as an in-house lawyer, and being given incomplete information is one of my pet peeves. And, frankly, when I’m asking questions in my capacity as an in-house lawyer, I need to know the answers in order to protect the company–it doesn’t matter if my internal clients don’t understand why I’m asking. That having been said, perhaps you need to pay attention to how you are doing this. Do you interrupt people when they are still speaking? Do you ask really irrelevant questions (like why is the law abc rather than xyz)? Do you fail to respect their time? How is your tone? My boss in my first in-house legal position advised me, “If you don’t understand the deal, keep asking questions until you do. Very often what you’ll find out is that they don’t understand the deal either.” But you can do this is a polite and respectful way.

    1. Jennifer Juniper*

      Aren’t people just supposed to go along with policy and procedural changes unless they’re a manager or director or or something like that? Yes, I’m being serious. Asking why is going to be seen as being obstructionist and not being a team player in many organizations.

      1. Original Poster*

        OP Here: at least on my team, we are creating our own workflows, procedures, and policies as a collective. We have general guidelines, goals, and oversight from our management.

        For example, we log all of our customer interactions in a ticketing system. The ticket layout was designed before I joined. Last month, we had to overhaul the entire layout because the data we were collecting (which is defined by the fields we included) wasn’t as useful. We brought in someone from the analytics team to help out, and when we implemented the changes, we lost a lot of data. To recover, we had to set aside a whole day (x3 workers) to put everything back where it belonged.

        It’s these kinds of ‘on the fly’ decisions I was referring to. But the point(s) made elsewhere about tone and phrasing are well taken.

        1. ComeOn!*

          But this is also just how it goes when working in new systems – revamping. You might have unrealistic expectations that work is more controlled than it really is. And how great is it that you recovered the data! I think you can flip the negative (we were not well enough prepared, not enough questions were asked, etc) to – WOW! the team made it happen.

        2. Observer*

          The thing is that when you ALWAYS ask why – when it’s your default, you actually lose the ability to ask why and get a useful answer when it really counts. Also, it’s important to ask the right questions. In this case, it doesn’t sound to me like “why” would have been useful anyway.

          Sure, it might be useful to find out why the original system was designed the way it was. But the core questions your team should have asked and gotten answers for before making the change was what data do you need, and how will the old system map to the new system. (I’m talking from lots of experience cutting over systems.)

        3. RachelM*

          But this is what post-mortems are for. There’s no way you’re going to get everything right the first time and it doesn’t sound like the decision you’re talking about here was on the fly. It just sounds like people made a decision and it was off and now you deal with it by having a post-mortem. That’s how new systems work. Again, I’m not sure how early on in your career you are but no one gets stuff like you’re describing here right the first time, data is lost a lot of the time, and you live with it.

    2. Washi*

      Yes, if the OP is sitting in a meeting where people are actively developing a policy, then I think it’s totally fine to ask for context if you don’t understand the decision making. But this is apparently OP’s “default setting” and it’s not clear how senior they are. In a lot of contexts, it would not be appropriate for the OP to subject senior colleagues’ decision making processes to the Socratic method.

  45. LQ*

    In addition to making every one in the room report to you you’re also demonstrating that you can’t think for yourself. Why are we ordering more TP for the bathrooms? Because we moved 50 people onto this floor and so they’ll use more TP. You should be able to figure out a lot of answers on your own.

    Before you ask the question of someone else, come up with 3-5 reasons why it might be the case that the thing that is happening/going to happen/suggested is doing so. Exercise your own understanding of the world, your logic, your education, your experiences of the company.

    If you are worried about insufficient information or missed information torpedoing a project take meticulous notes. That is the biggest and most valuable Not Your Job thing you could do. (It also takes you out of the mansplaining/demanding that the female coworker answer to you dynamic out of it.) Then loop back through and if you really think something vital is missing, ask yourself (not someone else, ask yourself) a few questions: does this thing actually matter, has someone else likely considered and dismissed this, does this put us into legal trouble.

    If you have to say something try: “Hey, I’m sure I missed something but when I was reviewing my notes I saw that we don’t have a vendor for the secondary locks. I assume this has been handled but wanted to check since this is within my area of expertise.”

    If you do all this then you can end up in a job where you get to ask things like why are we doing it this way, and no really, show me in the law where it requires that this paper be pink. And then actually change it so you don’t have to have printed pink paper because it turns out to be a messy guy who retired years ago didn’t want to lose it. I’m guessing this is the kind of thing you want to do, but you have to be able to think through the problems yourself and demonstrate that you can not just ask why.

  46. Hikachu*

    I think the key to actually being able to change your behavior here is processing the underlying emotion as you why you feel the need to analyze the situation from all perspectives. The easiest way to do that, is the next time that this pops up, and you feel the urge to get more context and analyze it from all perspectives, don’t, and then see what comes up. Is it a fear of something?

    The language you used seemed to be quite… like you were driven by a desire (possibly for security or success), or how you see your own personality, and while I think those are a fundamental part of who we are, there are times when we learn to deny them that allow us to achieve higher levels of achievement (or whatever your goals are). It’s harder to self-sabotage when you’re at least questioning why you are acting a certain way.

  47. Kella*

    Two thinks OP said stuck out to me:

    “I’ve seen insufficient, untimely, or incomplete information torpedo a project or client engagement.” And also, “It’s fair to say that this is my everyday default setting, but I amplify it in project meetings/communications so nothing slips through the cracks.”

    This reminds me a lot of some issues I have, as many others in the comments have pointed to, with trusting that other people will do their part of the work effectively and/or with worrying that if they do it wrong, the consequences will come down on me.

    I’m wondering if in those experiences you had where insufficient information crashed a project, was the blame and responsibility inappropriately placed on you? Have you had bosses or other authority figures with bad boundaries that didn’t make clear what was your job and what wasn’t and blamed you for things you couldn’t possibly have prevented? Because wanting to make sure nothing “slips through the cracks,” sounds like you are concerned with far more aspects of the work happening around you than are actually your job to worry about, and that makes me wonder why you think you need to do that.

    I’d suggest two things:

    1. If you have trouble making a call on what you need to worry about and what you don’t, ask your manager if they can help you relearn this habit. You could either ask her specific questions, is this my job? Do I need to worry about this? And/or have her flag things she sees when you’re worried about something you don’t need to be.

    2. If you just absolutely have to know the larger context of something even if it’s not strictly your job, be deliberate in your word choice in asking. Saying, “I’m really curious about this, would you mind explaining to me how x works, if you have a moment?” instead of, “Yeah but, why are you doing it that way?” makes it clear why you’re asking and that you’re not making a power play. In particular, acknowledging that you don’t have an inherent right to their time, that they’d be doing a favor in explaining it to you, is important.

    1. Original Poster*

      You asked some questions that I’m prepared to answer!

      “I’m wondering if in those experiences you had where insufficient information crashed a project, was the blame and responsibility inappropriately placed on you? ” – While I haven’t been pinpointed for blame erroneously, I have been the last person standing (not fired or resigned) as the ashes of a lost account smoldered away. I was asked to answer for the actions of people who were not able to explain/defend themselves. This particular situation is unlikely at my new company, but has definitely colored my day-to-day approach. Though, that had never occurred to me before being asked. Thank you!

      “Have you had bosses or other authority figures with bad boundaries that didn’t make clear what was your job and what wasn’t and blamed you for things you couldn’t possibly have prevented?” Ding ding ding, right on the nose! Granted, I think my new situation is on a much healthier team and wouldn’t expect this kind of behavior. However, because we are so new and our mandate so broad, we don’t have the procedures for many of our day-to-day processes hammered down. My questions are to make sure we’re all under the same understanding of our current workflows, but I realize now that my questions are also informed by the long-term insecurities exacerbated by my most recent job. I’m working on not mapping my lingering feelings of that job on this new situation (which is honestly great).

      This feels like therapy all of a sudden! Thank you for the thoughtful questions and advice. I am grateful.

      1. pegster*

        See? Isn’t therapy great?

        But one thing that stood out in your reply OP, was this “My questions are to make sure we’re….”. That seems like a bit of a red flag. I think that many people are sensitive to someone asking questions for ulterior motives (ie. not asking a question to get an answer, but to using your question as a way to inform other people of something – sort of assumes you know the answer before you asked). I think there might be a better way to do that, and you might even want to consider if that should be your role. I get how you might have been left holding the bag in the past, but just something to consider.

        1. Quandong*

          I noticed this phrasing too, and it sounds like something a person who is a manager might say, or a project leader. OP if this isn’t explicitly your responsibility and role in the team, perhaps you might pay attention when you get the urge to take on this task.

          1. Kella*

            Yes, I noticed that too.

            OP, I’m super glad my interpretation was helpful! But as pegster and Quandong pointed out, “My questions are to make sure we’re all under the same understanding of our current workflows” points to you feeling responsible for *everyone’s* workflow, rather than just your own. Unless we’re misunderstanding the nature of your job, it’s not your responsibility to ensure that everyone has the same understanding, just to make sure that *your* understanding is the one that will get you where you need to be.

            That’s more of the feeling responsible for things that aren’t yours pattern and getting your responsibilities and others blurred together. I assure you, it is MUCH less stressful to let go of worrying that other people will do their jobs and focus on your own, once you learn to trust that they will in fact manage without you figuring it out for them, and once you trust that management will sort out any problems that surface, you don’t have to do that.

  48. Pay no attention to the man behind the curtain*

    Oh bother, we have someone like that here and it’s exhausting. It’s especially exhausting when the topic is very low stakes and really doesn’t need a “why” — either it’s mostly self-explanatory, or it’s just too trivial to delve into it philosophically. There doesn’t have to be a “why” for every little thing in life. Right now my Mr. Why is questioning everything in the style guide — why do we use AP style, why don’t we add periods for degrees like MD or PhD, why do we abbreviate the university name one way instead of another way… Thing is, he’s not in marketing or public affairs; he really doesn’t need to know why, just what the style is and how to use it properly. If it’s not his preference…so what.

    1. Jennifer Juniper*

      Send him over to a grammar website and he can explore there to his heart’s content. That guy sounds like a huge pain.

    2. TootsNYC*

      and for many of those specific questions you list, there is really only one answer: Because.

      It’s style. Someone somewhere thought periods were unnecessary and old-fashioned, and that’s what we do. There is no other reason. What’s important is to be consistent.

      OK, maybe “we use AP style because more people know it and the books are easy to get, so it’s easier to be consistent. And because we often send out press released, and almost every person we send them to uses AP style, so we’re more likely to get picked up.”

      But I bet that’s not the answer he’s looking for.

  49. Jennifer Juniper*

    When someone asks for detailed information every single time, I start panicking because I’m scared I’ll be dragged into an endless round of tangents and not be able to make it out the door on time or not be able to get my chores done. The OP could also be making his coworkers anxious by doing an unnecessary time-suck routine.

  50. Former Young Lady*

    My former partner was a lot like the OP — it was one of those deeply-ingrained traits that can be either a superpower or an Achilles’ heel, depending on context.

    One reason she is my former partner: she never could figure out when to deploy the inquisitiveness and when to stand down. For every one process she improved, there is another where she exhausted others by demanding explanations she could have Googled, or torpedoed our productivity by trying to reinvent the wheel. She made herself miserable, and she got a reputation for those blind spots. Her real innovations became needles in a haystack.

    As a natural problem-solver, you need to make sure you “triage” your inquiries appropriately. Each time a question arises, first ask yourself:
    – What is the likelihood that this question has already occurred to those who set the policy/designed the process/etc.? Am I really the first person in the history of the institution who might have questioned this?
    – Do I need to know urgently, or I can I write it down and follow up later? Is it possible the person training me has an interest in getting me up-to-speed on the “how” and “what” before she has time to address the “why”?
    – Might a quick Google or a cursory skim of the handbook satisfy this curiosity? Could I ask for links/resources to study on my own?
    – If I am really convinced that I can improve this process, does the revolution have to happen right now? Is it possible I could glean more insights by first familiarizing myself with the status quo?

    The paradox is that this kind of knowledge is also institutional knowledge, and it requires its own cocktail of time + asking questions + reading the room. Always remember that when you’re the new kid in town, everyone else is investing in you. If the position took a while to fill, they’ve almost certainly been doing extra work in the interim. If they’re training you, that’s probably taking even longer than the work they were covering after your predecessor. They desperately want to get you up to speed with minimal friction, so they can get back to their own workloads. They are already under pressure, and even good-faith curiosity might feel more like a demand that they justify their existence.

  51. Stuff*

    When you’re new – unless it’s your job to change things – it’s best to just hunker down and do your job. At some point if you see something lacking then you can drill down and ask questions. But in reality most of your questions have already been asked and answered before and you just waste other people’s time.

  52. SpaceballOne*

    Speaking as a person in charge of an aggravating product that many people in my workplace are very invested in, but very few take the time to actually understand — please be careful with all this questioning. I have heard so much “helpful criticism” and so many loaded questions (“but why would you do it this way when it makes the final product so inconsistent?”, “but why won’t you take more control of the product, if you think it’s inefficient?”) that my hackles go up the moment someone opens their mouth. I really appreciate a sincere “So, why have you found this to be the best option?” — it at least nods to the fact that I’m an intelligent person who might, you know, have a reason to do things the way I do.

    Questions for context can be fine, but be very careful of how you word them, and don’t overdo them.

  53. Original Poster*

    Wow, I was told to expect great feedback and expanded interpretations in the comments, so thank you all for your thoughtful input.

    For further context, I joined a team of two existing individual contributors (I am the third), a program manager who is responsible for representing our interests as we relate to other teams in the company. What has been made clear to me after reading the Manager response and the subsequent comments is that my questions could definitely be rubbing the program manager the wrong way. Definitely “not my job” territory.

    Now that I have seen some of the more negative interpretations that could arise from my inquisitiveness. I think the first, most helpful tactic will be to ask myself, “Is this really my responsibility to worry about?” and “Can this wait?” I will also have that conversation with my peer to get her feedback directly.

    Thank you all again!

    1. First Time Poster*

      Way to take feedback, OP! Very good luck to you!
      I’m kind of how you are with questions. I’ve learned to tone it down in recent years by using the types of suggestions above. Turns out, when I’m not questioning *everything*, I am more heard when I do ask a question. Now I’m known as the “insightful one with good questions”!

      1. Willis*

        Yes! to be being better heard when you ask less questions.

        Also, props to the OP for writing in and being so receptive to Alison’s advice and the comments. I think the tactic you outlined sounds good and could really improve interactions with your annoyed colleague. (Also, I kinda love that the approach to curbing the number of questions you ask is to begin by asking yourself questions…sort of turning the tables, eh?)

    2. Dust Bunny*

      We’re an opinionated bunch.

      We don’t want you to not ask, but we also don’t want you to meet resistance when you really do need answers.

      1. Observer*

        but we also don’t want you to meet resistance when you really do need answers.

        That’s SO important to realize.

    3. Myrin*

      It’s great to see you’re so open to examining yourself and really taking in what people are saying. Good luck navigating this in the future, OP, you really sound like you’ll be able to implement the advice given!

    4. LCL*

      What is really awesome is when new people, such as you describe yourself, write down those questions and we can return to them later. I work in an environment where the emphasis is on processes that get the job done using a mix of ancient, old, and cutting edge new technology, while not killing anyone or breaking anything. If we have a process that works, and I am questioned about it in the moment, I may shut you down with ‘because that’s how we do it. But after this job I want to hear your insights and suggestions for how to improve things.’ There is often some way to improve a process, and analyzing it helps keep us sharp. So it may not be your questions that are off, so much as the timing. I can explain something all day, after we have got the work done.

    5. Kathenus*

      Thanks for posting and for being so open to feedback. I’ve dealt with some similar things in my past, where either asking questions or giving an example of something from a past job of mine can come across really wrong. My organization can be very hierarchical – what matters is your time here not necessarily your overall experience – to some, anyway. So I started asking three internal questions before chiming in, in some contexts – Does it need to be said? Does it need to be said now? Does it need to be said by me? It’s really helped give me an internal checksheet to help keep me from stepping on toes with some folks. Maybe some sort of method like this, or writing down questions for possible later investigation as was mentioned above, might be useful for you as well.

    6. Beth*

      Asking yourself these questions sounds like a great approach! Hopefully through that self-interrogation, you’ll be able to pinpoint when your questions are going to have a real impact–and if you limit them to those situations, you’ll likely get a reputation for asking insightful questions at exactly the right time, instead of one for generally overstepping and being challenging to work with.

    7. AngryOwl*

      What a lovely response to feedback that had to be tough to read at times. Thanks for providing more context, and good luck!

    8. Jules the 3rd*

      Wow, you’re taking this well! Please send us an update at EOY on how things are going for you.

    9. Anne*

      One thing I would caution you about, as a manager of a team with many arcane processes that receives data from many other departments, there are going to be times when if you ask these questions the answer will be “I don’t know, we just do” or something that sounds weird or nonsensical or like the process or method is unnecessary. And that’s not because these things are necessarily true, but the person you’re asking may not be the person with the actual answers.

      People misunderstand things or make assumptions based on their own experience and their piece of the process, and they think they have the big picture but the view they see through the frame is really a small part of a whole. Things get lost over time and turnover so while the executor of the process may once have understood ~why~ they format this 30-column spreadsheet in a very specific way, the person doing the process today may not know that it’s because the system it will be imported to has very specific data requirements. “We just do” the process this way. Or they make up their own reasoning.

      Being flustered may not mean people haven’t thought through their processes and you caught a gap – it may just mean “I know there’s a good reason for this but I don’t recall it off the top of my head”, or “this is how we were told it had to be sent to Anne’s Department”, or even “I get awkward when being put on the spot”

  54. Sylvan*

    OP, I don’t think you have any bad intentions, but you might want to dial this back. A different perspective, if it helps? I’m curious – I’ve yet to have a job that didn’t let me be a fly on the wall in some way – and I’m also very quiet in real life.

    – If your question isn’t about how to do your own job, it can wait. Prioritize.
    – People will usually answer your questions if you wait for them to finish speaking or demonstrating.
    – If that doesn’t happen, someone else will probably ask your same question.
    – When you’re working on a task with someone, the reason they do something in a certain way might be clear by the end.
    – When you’re learning a common task, Google or YouTube can probably answer your questions.
    – If you feel your thoughts or questions are too important to skip, but you don’t want to disrupt people, write them down. Save them for later.
    – You don’t need to talk a lot to demonstrate that you’re smart or capable. People can tell. :)

    1. Potato Girl*

      I <3 your last point and wish I could stitch it onto a sampler and hang it above my coworker's desk. People who ask questions for the purpose of showing off are so very tedious.

  55. Observer*

    I haven’t read most of the replies yet, so I may be duplicating – Sorry!

    One thing jumped out at me – you mention that you “press” this coworker for information. Unless you *need* that information or it is REALLY relevant to your projects, you are WAY over-stepping. It’s just not appropriate to press people for things as a “default setting” on stuff that you just want / like to have / find interesting.

    Given the explanation you give for your behavior, I have no doubt that you definitely come across as not trusting anyone else’s thought process. At minimum people are almost certainly thinking “Why is he pushing for all of this extra information that he really doesn’t need when we’ve got all of this stuff to get done?”

    1. Argh!*

      One of the key life skills to learn at work is to tolerate uncertainty and discomfort. We need to learn the difference between what we need in order to do the job and what we need in order to *feel* we can do the job.

  56. Bend & Snap*

    I’m an auditory learner but I don’t grill people on a whim.

    Listen in meetings and formulate questions related to your work and role
    Set up a time with the right person to ask those questions and apply your knowledge
    Be patient as you learn your role and the business
    Be aware of what you’re asking of others

    Ask questions, especially in public, about things that don’t pertain to your job
    Ambush people with questions when they almost certainly should be doing their own job
    Overstep your role and question people about how/why they do things in their jobs

  57. anonaa*

    Alison’s advice is spot-on as usual. OP, it’s good you’re aware enough to ask the question, too.

    I know that if I were your colleague, there’s a chance I’d be pretty annoyed by this behavior – like you’re essentially saying that having your curiosity satisfied is more important than my time.

    I’ll admit I’m a little biased as a woman doing kind of niche work in a larger organization where a lot of the leadership is male/tends to mansplain. Honestly sometimes when people ask me questions about a deep-level aspect of my work and it’s not based on something they need to know for their job, I can also bristle a little that they think this deep-level thing is something I can explain to them and they’ll understand in a few minutes. So it’s not only the claim on my time, but the implication that this stuff that I have a ton of training and experience with is simple enough that they’ll fully understand it right away.

    BUT – if you’re genuinely curious, I would be totally fine with being approached at a time I’m not obviously crazy-busy. If a curious colleague asked me if, sometime when it’s convenient for me, I’d give them a little more background on xyz just because they’re curious, I’d be happy to do that.

  58. Destroyer of Worlds, Empress of Awesome*

    When I worked for the whistleblower company, my first receptionist there was a “why”-er. I asked her to type a letter. “Why?” How about you read the letter while you type it and find out. I asked her to make a New Hire Checklist. “Why?” Why would any person need something like that? So they didn’t miss anything. It got the point that my boss (the president who looks like Charles Krauthamer if CK used Just for Men Jet Black) told me to sit down with her and talk to her about that and many other things. So I did. I explained to her that her constant questioning and “Why”-ing was inappropriate….sometimes things just were that way. I was new in the position too, and was going to stick with tried and true methods to get this company going (it was a start up and her role was *not* collaborative with me, I was her manager). So anyway, I’m talking to her and explaining why all of her why-ing was going to shoot her in the foot and that it had to stop because I didn’t have time to explain every decision I was making and also, well, I didn’t report to her. She reported to me and if I feel she needs to know the why, I’ll tell her when I give her the assignment. But for now, the why-ing had to stop.

    She looked me dead square in the face and said…..”Why?”

    I &hit you not. I felt tears well up in my eyes.

    1. CommanderBanana*

      My god.

      What happened??? Please tell me she left or you got rid of her.

      Also, as my mom would say, sometimes “because I said so” is actually an answer.

      1. Destroyer of Worlds, Empress of Awesome*

        Well, immediately after she said it, (i had had my hands clapsed under my chin) my hands sort of fell to the desk and I said “You’re kidding right?” She screeched “NO DAMMIT I’M NOT F*CK THIS I QUIT!” and she stormed out.

        1. The Man, Becky Lynch*

          Hahahahahahahaha, yeaaaaaaas, this ending is the best even though it was a painful journey to it. At least you didn’t have to fire her because instead of the “You’re kidding, right?” my response would have been “You know what, this isn’t working out, you can go ahead and clean out your desk.”

          As a former EA/support person, I cannot imagine ever responding to requests with “why”, I ask backup questions to preform the task like “use letterhead or just slap a logo on it?” or inquiring about the formatting if necessary but “type this up for me will ya” and responding “Why tho?” is such a crazy concept to me, I cannot even start to begin to wrap my mind around that nonsense.

          1. Destroyer of Worlds, Empress of Awesome*

            That was exactly my deal, too. Even though she said she understood the chain of command, I think she really ultimately thought ours was a collaborative effort when it really wasn’t. There would be things to collaborate on later, but when I’m establishing processes from scratch, well, that wasn’t the time.

            She was 20, very young, and actually wanted to rewrite her job description with duties she wanted to do. I was like, “Ummm yeah, NO.”

      1. Destroyer of Worlds, Empress of Awesome*

        A couple of months later, I ended up being fired for being a whistleblower (which was the source of much amusement on a few Friday open threads back in July) and three weeks after *that* I was in the hospital with stress related cardiomyopathy.

        I’m positive she was part of the reason……

      1. Destroyer of Worlds, Empress of Awesome*

        Didn’t have to worry about it!

        Immediately after she said it, (i had had my hands clapsed under my chin) my hands sort of fell to the desk and I said “You’re kidding right?” She screeched “NO DAMMIT I’M NOT F*CK THIS I QUIT!” and she stormed out.

  59. That One Person*

    I would consider phrasing of questions too because there’s a difference in demanding or digging for an answer, and posing a question out of curiosity/a desire to understand the process. In one strain you’re coming across as bossy, looking for something specific, or maybe just aggressive. Anything from tone to word choice can help change that, though as OP stated that they’ve seen things made or broken by inefficient and incomplete information destroy projects I’d especially be careful about that coloring the questions too. I tend to like to know the “whys” of things too because if I understand why something is done the way it is, then it makes sense to me and becomes something teachable to others as well. If I don’t understand then it leaves me on shaky grounds so when I run into deviations and things outside the norm…I become lost. Basically with math if a teacher could clearly outline why we did what we did with problems then I was golden, and if their example was sloppy and all over the place…well the text books could only go so far for me.

    However asking more in the frame of understanding the process is different, just still be mindful of coworkers’ workloads and time as well. If they’re already stressing then trying to take time when they feel as though they’re already running about isn’t going to help. Thus you might have to let things go for a short or long term interim because it may not be a good time to change that process right in that exact second. Some people may be finicky about questions regardless of anything else out of sheer personality, but it still helps even a little in the approach form.

    If something’s still a new process given that you’ve only been there three months there’s some room for leeway in some areas I imagine, but again still be careful how you ask in those situations.

    1. Original Poster*

      Framing my questions more thoughtfully is one point I’ve taken away from all of the great comments, yours included. Thank you!

      1. Danger: GUMPTION AHEAD*

        Timing is also very important. If we are in a 1 hour meeting and I have X, Y, and Z that I need to cover, with Y and Z being the meat of the matter, and you keep asking me questions about X for 10 minutes I will be ready to throttle you by minute 5. If you hit me up after the meeting and say, Hey, I have some questions about X, do you have 15 minutes this week to talk about it?” I am going to be totally happy to answer your questions

      2. EventPlannerGal*

        I’m glad you’re here in the comments, OP!

        One more thing that I would suggest is to think about how you’re responding to the explanations that you do get. This plays into the mansplaining/man-questioning thing – I can’t tell you how many men I’ve had demand an explanation of something from me, then respond with something along the lines of “oh, well, I wouldn’t have done it that way… but your way is okay, I guess.” I’ve had this about work, about hobbies, about my own Masters dissertation, whatever.

        Basically, are you responding in a way that reinforces the fact that you are asking out of genuine interest/desire to do well, and thanking your colleague for taking the time to explain? Or are you just going “oh, okay” or “hmmm” or “well, I wouldn’t do it like that…”? Because that will really affect how people will perceive your questions going forward.

  60. Liz T*

    Oh lord–IN meetings? Please please don’t do this in meetings! It makes the meetings take three times longer than needed and totally disrupts the agenda. If you’re curious, ask as a favor, separately, not when you’re holding everyone hostage.

    You are absolutely aggravating people and yes, probably coming across as sexist, or at least ignorant of male privilege. (I have had men do this to me while I’m trying to run an event on a very tight schedule and the answers didn’t even affect them. I’m not saying they wouldn’t do the same thing TO men, but I’ve only ever gotten this treatment FROM men.)

    1. Guacamole Bob*

      I’ve noticed there’s a certain level of self-confidence or even arrogance that is usually noticeable when people do this in meetings. The background assumptions that you’re making as a questioner in that scenario include 1) that it’s okay to use everyone else’s time to go over the answers to your questions, even if everyone else already knows the answer, 2) that the people in the meeting haven’t done a good job up to this point and so it’s worth re-hashing the whole process in that moment now that you’re present, and 3) that you have the right to have answers to all the nitty gritty on everything even if it doesn’t really concern you.

      The people who I’ve had do this recently are all men – the particular brand of self-confidence that it requires tends to come from those who have traditionally been in positions of privilege.

      1. Liz T*

        Absolutely–and the training starts really early. I will never forget the name of the 8th grade teacher who chided me for speaking without raising my hand and then praised a male classmate for saying the exact same thing, also without raising his hand. Boys are just conditioned to feel that their comments are desirable in a way girls are not.

    2. anonaa*

      Yes, this! Especially your last point – it’s always people in the more privileged position who ask these kinds of questions.

  61. Bopper*

    Me and G were new to our product. We were both assigned a feature of the product to work on.
    I was assigned left handed spouts and he got right handed handles.
    He wanted to know everything about teapots before he could get started.
    I learned about spouts and what is needed for left handed ones…and did my project. In the course o that I learned about spout/pot intergration points and the overall use of teapots.
    He took forever and got his mentor annoyed…what was supposed to be half a day of training dragged on and on because he wanted to know everything.

    So to the OP…pick your battles. You want to keep learning but not at the expense of taking up too much time of other people.

  62. That Would be a Good Band Name*

    OP, I feel you on this. I am a person that needs ALL the details. If I’m responsible for ABC, but I also know how ABC is linked to DEF and what effect that has on GHI, then I better understand my job. However, I learned there is a time and place for the questions. Meetings are almost never the place (takes too much time). I’ve found that people are most receptive after everything is finished and then you go back and say “I’d really like to understand this better. Can you help me with why we ABC and not BCA?” Especially since you are new, it gives the framing of just wanting to understand.

    1. Falling Diphthong*

      Meetings are almost never the place.

      I think this is a valuable insight–people much prefer a focused meeting that sticks to the essential topics and then lets everyone get back to work, over one that wanders off into interesting tangents every five minutes. Even though the latter makes for a better casual conversation.

      See the example upthread of an office Fergus whose colleagues doubled the time estimate for any meeting he had to attend, and tried to make them during his dental visits if time was crushing.

    2. Spargle*

      “If I’m responsible for ABC, but I also know how ABC is linked to DEF and what effect that has on GHI, then I better understand my job. ”

      I always wonder at statements like this. At some point, I would think that it’s just information that’s fun and interesting to know, but doesn’t actually impact the job itself. Some tasks don’t require understanding, they just need to be done.

      1. TassieTiger*

        Well, if ABC is the shape of the teapot lid, and DEF is the different countries your teapot lids are shipped to, you might start to want the culture of those countries to inform the shape lid design

        1. Allonge*

          But then again, your grandboss may have decided 5 years ago that that kind of customisation is just Not Gonna Happen. In which case you are wasting company time – yours and the askees.

        2. EventPlannerGal*

          Right, but it’s also vital to have a good sense of perspective on what will and won’t actually be useful. It’s very easy to end up spending a lot of time going down very interesting rabbit-holes with this sort of thinking that ultimately don’t take you anywhere; and while people are welcome to do that, if you’re asking other people to spend time guiding you down those rabbit-holes you should have a good reason for them to do that, and not ask it all the time.

          1. Falling Diphthong*

            Family trip version:

            “Let’s go down this fascinating rabbit hole…”
            “We need to choose a place and get dinner. Everyone is hungry.”
            “But there’s an interesting thing to explore! We don’t want to rush into a decision. It could be the wrong restaurant!”

            There’s a time to go down your interesting rabbit hole, and it’s not every damn time you see a bunny.

        3. Dust Bunny*

          . . . that would be interesting but it’s still not vital to the task, though, since the shape is already determined. If you want to reevaluate lid designs based on X parameters, that’s a separate project that it may or may not be your place to spearhead.

  63. CoffeeNut*

    I am someone who likes to ask the why questions a lot too. If I understand why/how we are doing something I am able to understand how my decisions affect others and can make better decisions. Once I realized some people were perceiving me as being difficult I started saying something to point out I am not trying to make things harder for them or challenging them, but I have a sincere interest in learning about the subject. “I’m not trying to be difficult, I genuinely don’t understand…” Most people are more understanding then and not on the defense or will simply state they have already told me all they know.

    1. Argh!*

      I think it depends on whether you’re in a decision-making role or just following procedures. Most people are just doing the latter when they’re new, until they learn enough to make decisions.

    2. Observer*

      In ai situation like this just explaining what you’re after is useful. Something like “I want to make sure that my decisions on spouts doesn’t have an unintended effect on your handles” goes a long way as well.

  64. EtherIther*

    I’ll be honest OP, just based on reading your letter, you’re probably annoying people. The notion of “I want to know how EVERYTHING works and make them better!” is just not always suitable. We’re sort of taught that in school, but it really applies less to jobs. A lot less. If your job isn’t specifically to improve processes, it isn’t likely to be a productive way to think all the time, and could be annoying your coworkers.

    I would really work on reframing how you see your inquisitiveness. Inquisitiveness is not always a positive trait! You should be less inquisitive when appropriate, and there’s times when it’s really just going to result in you being a pain for your coworkers. The reality is, work isn’t always the place for that sort of thing.

    If you’re particularly interested in learning and how things work, perhaps pursuing that outside of work would help? Take a class? Read some books on new subjects? And so on.

    Good luck!

    1. Keyboard Jockey*

      Or find a job in technology, where learning at a constant, exhausting rate will be foisted on you whether you want it or not! (says the front end developer)

      1. EtherIther*

        That’s true! It’s possible OP would be happier in a different type of job. (or perhaps learn they don’t enjoy that exhausting rate of change, haha)

  65. ComeOn!*

    Keep in mind that you (all of us) also learn by doing. Not all of your learning/training will occur by other people explaining things — or by verbal discussion. Rather, connections are made by engaging in the work. Sometimes when I am asked questions, it can feel like the person wants me to do the work of parsing out everything rather than them taking a risk and trying to make it work. It also assumes that I have all the answers and that answers just have to be imparted. But I find work to be more exploratory than that. Mistakes are part of the process (we are not doing brain surgery in this office!) — and that is what is fun.

  66. Obelia*

    OP, I’m currently working with someone who likes to approach things the same way you do, and we haven’t found it offensive – it’s quite clear that the person is asking from genuine interest and wanting to be fully informed – but it can make training / handover SO hard! It can disrupt your train of thought and you end up spending lots of time on things which aren’t immediately essential, at the expense of the key points.

    There isn’t necessarily anything wrong with wanting to know that contextual information, but as others have mentioned, it can be more useful sometimes to allow the person providing the information to set it all out in the way they find most practical, and then ask the context questions afterwards / later / at another time.
    Great to see you in the comments, sounds like you’re taking everyone’s feedback on board in a really positive way!

  67. The Happy Intern*

    As someone whose direct coworker was exactly like this for several months before our manager outright “Shh’d” her (they were mortified and immediately apologized) I can assure you that doing this is not only irritating, but also a real time waster and energy drainer. It doesn’t matter if it comes from good intentions, unless it’s your job to be asking “why” questions constantly I can almost guarantee it’s not just one coworker who’s irritated by it, others are probably just better at hiding it. It’s frustrating to have to constantly explain things that are already known, things that aren’t important to the task at hand, and it’s frankly exhausting to be the person on the other side of those questions. It’s also important to keep in mind that unless it’s your personal project that you’re intimately working with, assume that the person you’re dealing with already has the information they need for their decisions and don’t need to be questioned on every little thing because it’s their project not yours – you’re not the only person competent at their job on your team, you have to trust your coworkers are too.
    The biggest thing to help with this is to find the information you want on your own before asking people. While this is challenging if you’re doing a lot of new things, I work at a startup too and you’d be surprised how many things are actually industry protocol and therefore lots of info can be online if you know how to look! I’m sure this will help reduce your need for answers and will also give you a lot of extra information along the way that could potentially help someone down the road!

  68. Argh!*

    Just from the title, I’d say “yes.” Then after reading the letter & response, very much yes. Maybe not every coworker and maybe not every situation, but they don’t really want to spend their time this way. A *little* context is important, such as “Be sure to check off every item on the invoice so Betty can pay the vendor.” More than that would be too much, and if the person doing the training is super busy (probably catching up after having to do two jobs for months), they may not even want to go that far. Betty would let you know why it’s important after you screw up!

  69. CM*

    OP, you mentioned above that you’re starting to see your questioning as as extension of needing to prove how smart you are. The one piece of work advice that always stuck with me about this, which I think will be useful to you, is: Don’t be smart, only be helpful. Before you open your mouth, ask yourself: will this move the discussion or task forward in a way that will help us achieve our goal? If the answer is no — you’re just curious, or needlessly playing devil’s advocate, or showing how much you no — keep quiet.

    If you are curious about how things work and genuinely believe that the context is needed for you to do your job, I recommend keeping a list of questions and finding a time to ask them to your manager or a friendly coworker when you’re not disrupting their work.

    1. CM*

      “showing how much you no” was a weird typo. I no how to spell but sometimes I forget.

  70. The Man, Becky Lynch*

    A lot of this has to do with who you’re asking questions of and their own personal feelings towards you or your questions.

    I love questions and will answer just about anything, barring it’s not confidential or propitiatory of course. My boss is the same way, however everyone fears him because of his title in the company, so guess who gets to field the questions everyone wants from him? Yeah that’s me.

    However I have limitations, if you’re whole questioning process is to try to make me change how things are done or convince me you know my job/our company better than anyone else despite only being here 3 months, I will shut it down. The thing is that I’m also vocal and will tell a person if they’re being too abrasive or asking questions that are none of their business or concern, most people are conditioned to never do such a thing because they’re supposed to be ‘nice’ and it’s not ‘professional’ to tell someone they need to stop talking and start doing some actual work.

    Know your audience, always know your audience. It’s my motto for everything at this rate. If you feel they’re frustrated, they are probably frustrated and not feeling like they can tell you to knock it off. So please, just stop.

  71. Artemesia*

    I need context. I noticed that it made doctors often defensive and especially made nurses defensive to be asked for the reason for treatment suggestions; the nurse response was always ‘doctor wanted us to do this’ which is not good enough for me. ‘I understand that this med is used for this, why are we using it for this other thing?’ This sort of thing really annoyed medical professionals who worship the idea ‘doctor said. . .’ I found that it helped if I said to the doctor ‘I really do better when I understand what the situation is and why we are doing things a certain way. I am not doubting the recommendation; I just need to understand it.’ Most doctors these days — less so, 40 years ago — are good with this. But it really helped to frame it as my need and not questioning their expertise.

    I think on the job it is similar. Sit down with a colleague ONCE at the start of something and say ‘it drives me nuts to be dropped down in the middle of things without really understanding the context of how we got here and why we have chosen this approach; I just do better getting it done if I understand how things fit together.’ And then discuss context. You are the listener and learner, not the challenger. It is the constant annoying picking at everyone that makes it seem like know it all new guy challenging everything we do.

  72. Keyboard Jockey*

    I may be in the minority here, but I think this is a very valuable tendency — misapplied to meeting situations. If you want to ask “why” in a meeting, write it down and ask in private afterwards so that folks who already know the answer don’t have to sit through an explanation of the last five years of company history, or somesuch. It’d also be valuable to not just ask why something is as it is, but to add some context of your own around why you’re questioning it: do you think there’s a better way? a viewpoint that’s not being considered? That kind of thing is _far_ more valuable to bring up than just asking the “why” question, which doesn’t on its own challenge ingrained thinking.

    1. Dust Bunny*

      Nobody said it wasn’t valuable, and almost everyone has said it’s misapplied. The misapplication is the problem.

  73. Beth*

    This is my personal inclination as well–not even because I generally suspect anything is wrong, just because I really like understanding the ‘why’ behind things. It can be a useful trait! It can go a long ways towards uncovering bad or outdated processes and unchallenged assumptions. It’s also often easier to do a task right when I understand what the underlying goals for it are.

    But unless your actual job title is something along the lines of ‘quality control’, doing it all the time is really not okay. To be blunt, it gives the impression that you think your coworkers are incompetent. You say that you’re worried about “insufficient, untimely, or incomplete information [torpedoing] a project or client engagement”–but why don’t you trust your coworkers to do sufficient work and double check their information? You want to ensure “we are looking at a situation from all perspectives”–do you think your coworkers are doing shoddy work and ignoring useful perspectives?

    I’m sure you don’t intend it to come off that way. You’re trying to be thorough, and everyone misses things sometimes, right? But it’s not your job to monitor your coworkers’ work for those things. If you insist on doing so anyways, you’ll be seen as someone who thinks they’re better than the rest of their team, who doesn’t trust anyone else to do baseline quality work. That’s a relationship killer.

    Your coworker appears defensive because you ARE challenging her. And I bet she’s not the only one that’s feeling that way. Do your best to curb this tendency for a couple months and see what happens. I’m betting you’ll find that your coworkers do just fine without you expanding their thinking, and that your relationships improve a lot in the process.

  74. Penelope Garcia’s glasses*

    Until I learned you were male I thought you might be a newish colleague of mine who has been driving people up the wall asking questions about things instead of doing her actual job. She has grilled me on things to check if they’ve slipped through the cracks when it is not her job to check or her problem if they have. My manager and I have been discussing ways to get her to stop. I feel annoyed, frustrated and undermined. Please just stop – try listening and observing instead of endlessly grilling people!

  75. Sarah*

    There’s a BIG difference between asking someone “Why do we do X that way?” and “Just for my own information, why do we do X that way?” or “I’m curious about the big picture, why do we do X that way?” or something similar. The latter should also be followed up with something like “OK thanks, that really helps me understand the overall workflow/perspective of X department/restrictions the X team has.”

    Also, unless your role is related to making sure nothing ‘slips through the cracks’ then… maybe don’t make that part of your daily work, especially if you sense it’s causing tension with others? And if things are slipping through the cracks, bring that up to your boss/the team leader and let them direct reviewing the bigger picture.

  76. char*

    Ha, I’m sort of the inverse of this, in that I have a hard time restraining myself from giving ALL the context ALL the time. I like people to know why we’re doing what we’re doing.

    But when it comes down to it, it’s not always a good use of my time to spend half an hour crafting a point-by-point missive explaining why I think it’s a good idea for my team to do the thing, when all my team really needs to know is… that I need them to do the thing.

  77. False*

    I think there are two issues being conflated here in the letter and in the comments.

    I am a WHY person (inherently), but at the same time, I’m also not (inherently) a detail-oriented person. There is a huge difference between wanting to know the WHY of something and wanting to know all the details of a project or procedure. A lot of commenters here are lamenting coworkers in meetings who derail the agenda by asking too many questions relating to precise details, which obviously can come off as undermining everyone else’s position and expertise, as well as takes up time unnecessarily. This is not the same thing as being a “why” person, and is probably more closely an attribute of “how” or “process” oriented people.

    The OP writes “I’m inquisitive by nature: I always want tons of context and I tend to ask a lot of questions that boil down to ‘but why is it this way?'” This is actually not a question about the details of a process. If I were to ask this question, I would get extremely frustrated if the other person started explaining the steps of the procedure to me again, as it’s a waste of time and signals to me that they weren’t really listening to my question, and just assumed I didn’t understand the issue. I would think, “No, that’s not my question. ‘Why’ are YOU wasting MY time by giving me extraneous ‘how’ details when I simply want to know ‘why'”.

    “Why” is a question about the background, context, and initial mindset surrounding the decision making around the issue. If this can’t be summarized in under 5 minutes, then there most likely is a huge problem somewhere that needs to be addressed. Things like “it’s in the style guide” and “the vice chairman wants it that way” should be suitable answers to the “why question”. The problem arises when this line of questioning has no exit, as in “why is this in the style guide from 30 years ago? We need to find the people who wrote and question their mindset.” or “looks like we need to corner the vice chairman at his home and make him explain every step that led him to have this preference”. If this is what the OP is doing, then yes, it’s extremely disruptive and will literally never end.

    However, I get the sense from the letter that the other thing I alluded to is happening; the OP is asking a “why” question and receiving a “how” answer, and the dissonance there is forcing him to realize that there is a breakdown in communication that’s making him and especially his coworker uncomfortable. My advice about this for the OP is to ask better “why” questions:

    “Oh, was this the new process Fergus laid out in that meeting?” Translation: Are we doing this because it was decided by someone at a higher level? If not, who decided it, and is it intended to be a standard procedure from now on?
    “I see you used these figures. Did you get this from the Wakeen report?” Translation: Did this data come from the right source? If not, where did it come from, and why is it being used in this context?

    If you come at the situation by revealing our own context and mindset when you ask your “why” questions, you are more likely to receive an answer that actually has to do with what you’re asking. That can help you lead your coworkers into explaining the context and background behind things and giving an answer that satisfies you without really taking up too much time. That being said, it’s important to understand what question you are really asking, and if it’s being perceived as a different question all together.

    1. Penelope Garcia’s glasses*

      I’m not sure how relevant this is. The LW is questioning people about things that aren’t his purview.

      1. False*

        This applies to Beth’s comment below as well, but:

        It’s not necessarily clear that these things are not within OP’s purview.

        OP states: “OP Here: at least on my team, we are creating our own workflows, procedures, and policies as a collective. We have general guidelines, goals, and oversight from our management.”

        If things are being decided as a collective, the kinds of conversations OP is having are, in fact, extremely crucial. I think the fact that many people in these comments seem baffled or second-hand annoyed at OP is at least half of the problem; non-“why” people cannot understand why this information is important for “why” oriented people, and see those lines of thought as irrellevant. However, as a “why” person myself, understanding that context is step one for me to be able to wrap my head around a project or issue and begin to think about how to solve it. Considering OP’s own internal decision making process is “why” based, and that these workplace problems are being tackled “on-the-fly” and collectively, if OP wants to make use of his skills and perspective as a “why” person, he needs to translate that thought process into a form that “what” or “how” people will understand, especially since (as seen in these comments) non-why people are extremely perturbed by why questions in the first place.

    2. Beth*

      I don’t think this distinction is going to be useful to OP in this particular situation. Even for the ‘why’ questions, there’s a time and a place, and someone who doesn’t recognize that can easily disrupt conversations and come off as undermining their peers. Asking your coworkers to justify all their decisions on their work gets old very fast, even if each individual question only takes a moment to answer.

      1. False*

        I tackled the bulk of this in my comment above, but I do want to add one thing as a bit of perspective.

        The goal of asking “why” questions is not “asking your coworkers to justify all their decisions on their work”. The need to receive “why” information is simply the start of the thought process in order to understand something. I am sympathetic to the fact that non-why people do not understand this, and have tempered my own communication style when dealing with my own managers/coworkers, but when my work intersects with someone else’s, even tangentially, I will need to understand the “why” context in order to begin solving the issue I need to handle on my end. Simply being given a process and asked to add to it leaves me with no way to tackle the problem cognitively. Especially in the context of OP, where they are formulating and developing new processes that will presumably be used going forward, to me (again, my bias), figuring out why the process is important and the background context about where it fits into the overall structure of the company is the only way to properly understand the question and to then begin to decide the how of its optimal implementation.

        1. Violalin*

          I totally get this and I’m very similar to you, but I see people bristle at this approach and I sympathize with it. Even if the goal of asking “why” questions is not “asking your coworkers to justify all their decisions on their work”, these coworkers may not have always had a hand in decision making – maybe it was a past coworker or boss who implemented the policy, maybe they raised issues and were ignored, maybe they’ve hated this project from the start and would never have gone with it if it weren’t assigned to them directly. But answering “why” with “well, my past coworker/boss was a moron/didn’t listen to me” isn’t professional.

          Of course, it’s possible to work with this by giving context, but the reality is you’ll ask “why” questions to people who don’t have “why” answers and it’s going to make them feel inadequate. I think a person who credits themselves as a “why” thinker should be able to appreciate that.

  78. PorecelainOne*

    I got crazy mansplaining vibes from the OP. He knows he does it, he knows he’s offended at least one person by doing it, but he’s still choosing to justify his actions. I am a deeply inquisitive person but I also know you need to read the room and situation and not just barrel on with the kind of privilege that you think you’re entitled to ask continuously annoying questions just for your personal benefit. It also sounds like he’s choosing not to use any critical thinking skills because instead of taking time to pay attention to what’s happening around him and process it he just demands other people’s attention so he doesn’t have to think through anything. This screams serious privilege and lack of social awareness.

    1. Not One of the Bronte Sisters*

      I don’t get those vibes at all and I am female and extremely sensitive to mansplaining. And I don’t think he’s choosing not to use any critical thinking skills, not at all. I do think he needs to respect people’s time, watch his tone and listen before he speaks if he is not doing those things now. But to stop asking questions just because it annoys someone? Seriously?? I have had a long career as an in-house lawyer and I’ve had to ask a lot of questions and I’m sure that it’s annoyed people. Well, too goddamn bad. I do it in order to do my job.

      1. Dust Bunny*

        Not the same thing at all, though. If you’re a lawyer, asking questions is part of the job (I’m an archive assistant, so asking questions as part of research interviews is also part of my job). The problem is that he’s asking questions to which he doesn’t need to know the answers to do his work, at times that may not be apt for the questionees. The vibe here is that, even if it’s just cluelessness and not malicious, he feels entitled to their time, energy, and knowledge even when he’s really not, and doesn’t need the information for which he’s digging to do his own job. That’s where the mansplainy-ness is creeping in (not that women can’t do this, too. Maybe it’s more of a general oblivious-entitlement problem).

  79. Gemma*

    OP , you sound like you may have an ‘input’ strength (using Gallups system). I have the same and usually want to know everything and anything about my teams area of work (and comment on it). I generally take quite a wide view and think that having the information is useful to spot patterns or opportunities to collaborate. In saying that, people don’t have the time to tell me every little detail of their job or consult with me. I focus on knowing my particular things well (and sharing summaries/updates etc), having an rudimentary knowledge of what others are doing, accepting that not everyone is a sharer and that there are things that I can’t know (I’m not the CEO, some stuff is confidential). I then plug all my ‘want to know’ energy into researching our area of work outside of the organisation, reading everything the company puts out, commenting/sharing on LinkedIn etc – I think its about finding away to direct your energy. It’s all going one place at the moment!

  80. CM*

    “You’re going to… come across as if you don’t understand who’s responsible for what (or as if you don’t respect the people who own the areas you’re questioning and questioning).”

    I think this part of the advice is key. I don’t think it’s weird if the new privacy officer starts asking a bunch of questions about how we handle privacy and why we’ve been doing it some particular way. I don’t think it’s weird if the new data analyst asks a bunch of questions about why we’ve been storing the data a certain way or asking for certain analyses. I don’t mind, in either case, if they do it in a way that suggests our current methods don’t make sense. But it’s weird when someone starts asking a bunch of probing questions about stuff that doesn’t involve them. It makes you wonder why they want to know.

    HOWEVER. I also once (accidentally) worked for an organization run by a con artist where literally nothing we did made sense. Every single new hire would sit in meetings and get this twisted, confused expression before saying, “Wait — why are we doing X?” Because, even if the thing we were talking about wasn’t part of their portfolio, what we were actually doing was so blatantly at odds with what we said we wanted to do that any random person off the street would immediately be able to tell something was wrong. You were made to feel like you were a bad person for questioning anything, but actually the questions were very wise, and the people who resisted getting shamed into silence were the best of us.

    The point being, I agree that this is fundamentally a trust issue, with the caveat that sometimes you shouldn’t trust. So I think the OP needs to decide if this is a situation where he’s working with liars or in a place where there’s widespread incompetence — in which case he should probably bail — or if this is probably not that situation, in which case he should ease up and wait to see if a problem emerges before he starts investigating things too much.

  81. just trying to help*

    First, as a grown adult, perform your own research to answer your many “why” questions. This research does not include interrogating your busy coworkers. This comes across as either infantile (think of that 3 year old constantly asking “why?”) or lazy and you expect to be spoon fed. Only when you can’t find the answers to your questions, and you can prove to your coworkers that you have tried to find the answers, start asking them for context.

  82. BananaPants*

    Yes, it’s likely that your coworkers find your constant questions incredibly annoying and you are coming across as mansplaining (regardless of your supposed sensitivity to this).

    If you genuinely have this many “why” questions, be a grownup and do your own research. That could include scheduling a meeting with a SME or reading existing documentation. As a manager, I expect an adult professional to do that rather than wasting everyone’s time in meetings with constant “devil’s advocate” questions and expecting to be spoon-fed the information you need to do your job. Unless you were specifically hired as a change agent, you need to know your role and stop demanding constant explanations/justifications for everything.

  83. Violalin*

    Oh man, I totally want to believe my new boss wrote this. I don’t think so, but it’s so similar. I appreciate the question-asking in a lot of contexts but I can see many of my team members bristling against it, so Alison’s advice is really good.

    From my experience on the other end of this, I think one of the reasons people may bristle against these “why ” questions is that it can feel a bit like you’re being asked to justify/defend decisions you didn’t make. I know that’s not OP’s intention, but when you had a shitty former boss who insisted you implement a system you thought was poorly thought out and unnecessary, and the first question your next boss asks is “but why is is this way?”, it feels very demotivating. And the truthful answer (“because [past boss] was a moron?”) is unprofessional. I try to remember that my question-asker is just fact-finding, and not trying to blame me for things, but I’m not surprised that some staff are perceiving it that way.

  84. Violalin*

    OP: are you my boss? If not, then: Alison, is it inappropriate to send this post to my boss?

    Joking, of course, but it’s interesting to read the flip side of this as I’m watching my coworkers bristle against our new supervisor, who is doing almost exactly what OP described. I try to remember that this person seems to be on a fact-finding mission, but I also sympathize with the people who are struggling against it. When you had a shitty boss who insisted you implement a project you thought was unnecessary and poorly thought out, and your new boss asks you “why is it this way?”… well, it can be discouraging (and “because [past boss] was a moron?” isn’t an appropriate response!).

    1. Violalin*

      lol, my first comment didn’t post so I rewrote & reposted (since I forgot what I wrote) and now of course they appear back to back…

  85. nnn*

    As someone whose genuine interest in how things work tends to come across as demanding and judgemental, I have a couple of scripts that can help sometimes:

    1. “I wonder why…” followed by an immediate transition back on topic. Tone and delivery as though it’s interesting but unknowable. “I wonder why the dog always carries his sticks off-centre like that and never in the middle? Anyway, as you were saying…” This gives them an opportunity to answer if they know the answer and care to get into it, but also gives them an opportunity to get back on topic.

    2. “Do you happen to know…?” or “Do you have any idea…?” This mitigates the demanding nature of your inquiry and sort of acknowledges the fact that they aren’t expected to be able to give you an answer, but you think they might be able to.

    3. Do the work of guessing at the reason rather than demanding it. Sometimes the demanding tone can be mitigated with a trailing “or…”. Example: “Is that a food safety rule? Or is it for allergy management reasons? Or…?” That can come across as having more goodwill rather than being demanding, and portrays more of an impression of thinking and learning rather than insisting on being spoonfed the answers.

    All these would have to be used sparingly – if you overdo them, they’ll still come across as being annoying by asking way too many questions. But adding them to your toolkit might make you come across better overall.

  86. CJM*

    This reminds me of a colleague who nearly always challenged me on code reviews. He had transferred to our department from a different one and seemed determined to prove how smart and innovative he was. But he stood out as annoying and disrespectful of our department’s norms. In the case of code reviews, the norm was to receive the emailed code review from a senior developer, quietly take the steps outlined to improve the code, and move along. Instead he walked over to my cube almost every single time to challenge me. I was surprised the few times he didn’t do that. I was big on email over visits that interrupted me, as were most of my fellow developers, and that was yet another norm that he ignored. Often he couched his challenges in questions about why I decided something the way I did, but he always came across as challenging, and I felt nothing but annoyance.

    So my reaction to this letter-writer is that so much questioning probably isn’t well-received, and he’s probably earned a reputation as annoying. It’s better in my opinion to quietly observe and learn and accept idiosyncrasies for the first year or so. At that point experience may have explained so much — and given him standing to respectfully suggest changes.

  87. Calpurrnia*

    I have a kind of similar problem where when I ask people “why do we do X?” they interpret it differently than I intend it. I like context and knowing how things connect together, so when I ask “why” I mean “what is the motivation/purpose/goal for this?”. But a LOT of people hear “why” as “what is the result of doing this?”.

    So I’ll ask “why are you applying this function here?” and they’ll respond by explaining things like “it takes the average of the teapot counts in columns 3-7 and divides by column 12”, which… yeah, obviously, I can see that with my eyes? I didn’t ask WHAT the function is doing, I asked WHY we’re applying it here. So what I’m looking for is an answer like, “the people who read the report I generate want to hear explanations for any teapot factories whose volume is down. So this function lets me identify the factories whose average volume this week is more than 10% lower than the baseline average for the past year”. I want to know the purpose of doing the thing, not just what the thing is actually doing.

    I don’t know how to ask this question other than “why”; if I wanted to know how or what it does, I’d ask that instead. We end up talking past each other a lot, as I get quite frustrated by people not hearing my question and answering a different one, and they get quite frustrated by me continuing to ask “okay, I see that, but *why* are we doing this calculation?” to something they (presumably) think they’ve already answered. I’ve had entire meetings wasted where we both get increasingly frustrated with one another because no matter how I reword my question to make the meaning clearer (“okay, but what is the purpose of that calculation? Okay, but how do you use that calculation? Okay, but what does that calculation enable you to do?”) they continue to repeat or reword the same answer as though I simply didn’t hear/understand them the first time.

    I see a lot of frustration from other commenters above. I wonder if they’ve considered whether they might be actually answering a different question than the one the person asked. And similarly, I wonder if OP might be having the same communication problem with their coworkers as I do.

    1. Observer*

      Well, it sounds to me that you actually are not asking the question you want answered. Don’t ask “why are you doing this?” because that starts you on the wrong road. Instead ask “I see that you are multiply Column C by Column D and then dividing it by the number in Cell 2X. What does the result mean and how are you using it?”

      This tell the person you are talking to that you actually understand the mechanics of the process and what happens with the result. You’re not asking about the mechanics, and you’re not asking about the history.

      But, with the original question, it’s not clear.

    2. Allonge*

      Interesting. If you asked me why I am applying a certain formula in an Excel file I would always answer: because this is the way to calculate what I want it to calculate. Why do you ask, do you have a better formula? In some cases I may say: I know it’s an awkward way of calculating this but the whole sheet goes kablooey when we use [other formula].

      If you want to know what I do with the result (why it is important), maybe ask that. What do you use this number for? In which context is this necessary? How important is it that we know this? None of this is clearly indicated by why.

  88. Quinalla*

    I was just coaching someone on this very thing the other day (he has the same tendency to want to know the “why” of everything). I basically coached him that he needs to be strategic with the asking and make sure the other person has time for the questions and yes to explain why he wants to know and sometimes to just refrain and get the work done. I also advised that the more people are at a meeting, the less you should indulge this tendency. There are some exceptions, but I felt this was a good guideline.

    And my husband has run into this at work with two different people recently and it was really derailing the meetings he was running and he had to have an after the meeting one-on-one conversation with her after saying they needed to table that for later and the other person ended up getting hostile on the call when he attempted to table the discussion for later and he had to escalate to the guy’s boss.

    So just in my small sample, yes this can definitely be a problem. I know you are new at work, do you have any work buddies/friends yet you can ask for feedback too? Otherwise, yes I would approach the person directly and talk to them about it so you can have a conversation.

  89. Doris*

    I have a colleague who does this all the time. I’ve been pretty much at my wits end with it. I can only say how it makes me feel, and I feel very confused. The nicest explanation I thought of for her behaviour was that maybe she is just a bit anxious about getting things right. But really, it does come across as challenging, and overstepping her role greatly. I had slightly more interesting tasks than her, and I think she was misled to believe that we’ d have the exact same role. She wouldn’t believe anything I told her when she asked me questions, and then she’d always say ‘oh, I’ll have to ask the manager’. It came across like she felt it was beneath her and she felt that she was much better than me and should be doing my role. So now we’re in the position where, because of all her questioning I feel like she’s a bit inept and nosy, and, given her attitude, she possibly thinks I’m not that competent. I have spent a lot of time answering her questions and the whole situation has created some interpersonal drama that I really didn’t need to deal with on top of everything else this month. I think the easier interpersonal relationships will be a great trade-off for questioning a little less often.

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