my boss says I ask “why?” too often

A reader writes:

I have a tendency to ask why things are the way they are at work, because I like to know how everything fits together. Recently, it has come to my attention that my asking “why” doesn’t always come off well with my manager, who seems to take it as a challenge to her authority. That being said, I am writing to ask you a “why” question: why do you think that my manager feels that “why” questions are an affront to her authority as a manager? Do most managers feel that way? Maybe if I have a better understanding of where she’s coming from, I will have a better sense of when it’s okay and when it’s not okay to ask “why” at work.

This depends very much on context.

In many cases, “why” questions are great! For example, understanding the “why” behind an assignment will often help people do it better (like spotting ways to improve messaging or potential obstacles in a timeline). It also usually helps people be more engaged in their work and feel more ownership of it. Plus, some people simply learn better if they understand the reasoning behind something. And frankly, managers should want employees who are curious and care about understanding the full picture of what they’re doing, as opposed to people who will just carry out orders without thought.

But there are times when “why” questions can feel out of place, like if the “why” seems to carry a subtext of “this is stupid — why are we doing this?” or if you’re questioning every small thing your manager asks you to do. And sometimes you’re expected to understand that explaining the “why” would take more time than you just doing the thing and you don’t need to know anyway — for example, if your manager asks you to drop something off on someone else’s desk as you leave her office and you ask why, that’s going to be seen as pretty out of line. Or if you’re holding up a meeting to ask questions about small details while everyone else is sitting there waiting to move on, you’re going to look like you can’t read a room or judge when to follow up on something privately.

And to some extent, you need to invest your “why” questions wisely, because people are busy. That doesn’t mean that a good manager won’t want to take the time to explain things to you, but if you’re asking “why?” 15 times a week, it may start to feel like it’s not a great use of her time or yours.

It also matters how you ask why. Look at the difference between these:

Example 1
Manager: Thanks for writing up that piece for the newsletter. We’re going to hold off on it for now but might use it down the road once there’s been more time to edit.
You: Why?

Example 2
Manager: Thanks for writing up that piece for the newsletter. We’re going to hold off on it for now but might use it down the road once there’s been more time to edit.
You: Okay, thanks for letting me know. So that I can make sure I’m producing the right things, is there anything I should know about what didn’t work with this one?

In the second one, you’re not demanding info and you don’t sound like you’re challenging the decision — but you’re still asking the question.

Of course, it’s also possible that none of this is relevant to whatever’s going on your situation. Maybe your manager is insecure in her authority, doesn’t like to be questioned, and bristles at perfectly reasonable questions — in which case, she’s the problem, not you. It’s hard to say without knowing what kinds of questions you’re asking, how frequently, and in what contexts.

{ 316 comments… read them below or add one }

  1. Faith

    This can be generational. It drove my old boss crazy when I would ask why because I was trying to learn and better be able predict how I should respond next time a similar situation arose. With the help of my current boss we figured out it was how I learned, but they also think it has something to do with being a millennial. My current boss has grown to accept they why questions generally, but Alison’s example can help soften the question and frame it better for your boss.

    Reply
    1. Kiki

      I attended a conference with a generation speaker as their opener. He asked the baby boomers in the audience, “What’s your response if your boss says ‘Jump’?” and there was a resounding chorus of “How high?”. He then asked the millenials the same thing and the audience replied with “Why?”. The speaker went on to explain that millenials like to know the big picture and how they fit into the company’s projects and goals, while baby boomers tend to just want to get their job done and please their boss. Obviously you can’t project this out to all people in those generations, but I thought it was interesting.

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      1. Snowglobe

        I feel the need to point out that it might not just be that the Boomers ‘just want to get the job done’ but that they have enough experience behind them to intuit the ‘why’ in most situations. In other words, it’s more of an age thing than a generation thing.

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        1. grey

          I happen to agree because when I was younger I was much more of a “why” person, but as I got older I was able to figure it out. I’m Gen-X for generational background.

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        2. solar flare

          that’s extremely not the implication behind “when i say jump you say how high”, though. it implies that the person will follow directions, not that they have experience and intuition.

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      2. Observer

        Snowglobe is correct. A lot also has to do with the ind of job you are doing. For some things the response to “jump” NEEDS to be “why?” and for some jobs it NEEDS to be “how high?”. There are a lot of jobs in between. But when you are being expected to “take initiative”, be a “self starter” or work well with minimal direction, “Why?” becomes a crucial question. That extra background information can make the difference between being able to function in that kind of environment or not.

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        1. Jadelyn

          And even in jobs where it doesn’t *need* to be “why?”, taking the “why” route can still be helpful. I write reports out of our HRIS for various managers and analysts across the org, and when I was very new in this role, people would say “I need a list of staff who meet X criteria, with Y and Z fields included along with their names.” And I would say “Okay!” and pull it and send it to them…and then they’d come back and say “Oh, also can you add A-E? And break it out by Y?” And I’d have to either do all the manual work to add those extra things to the existing excel sheet, or just write a new report that included the new stuff, doubling the work I had to do.

          As I got more confident in my role and more familiar with the organization, I started asking “why?” to report requests. Not in the sense of challenging whether they really needed it, but asking them to provide me with some of the context behind it. Because if I had that context, I could often intuit some of the things they might need that they hadn’t asked for yet, and make suggestions about ways to sort and break out the data that would make sense with what they needed it for. People got used to the fact that requesting a report from me meant giving me at least a bare-bones one-sentence explanation, and then began to learn that it went much smoother and I was able to provide extra support and analysis if they told me more, and now at this point people take it as a matter of course. When they ask for a report, they say “I’m doing Thing, and I need Data.” and I can reply “Okay – would you like Additional Stuff included?” and they say “Oh, yes, that would be helpful!” and everything goes faster and we’re all much happier, as they get what they need right off the bat, and I don’t have to waste time because people didn’t think all the way through their request before I fulfilled it.

          Does my role really *need* to ask why? Not for most of these requests, tbh. I could function just fine in this role if I were a “how high?” type of person. But being a “why?” person has made me better at my job and more valuable to the org, and helped develop my reputation to boot. So call me an entitled millennial if you like, but I’m counting it as a net positive.

          Reply
          1. Observer

            This is a perfect example of what I was trying to say. *Technically* your job doesn’t require why. But to be really good at it, you need to ask the questions. That’s not being “entitled” that’s taking appropriate initiative to make people’s lives easier.

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          2. Susan

            The above is how I’ve always described the difference between a business analyst and a senior business analyst. The BA will just go do what you ask; the senior will ask more to get to the core of what you are really looking for.

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      3. Random

        If you can’t project this to all people, then there’s no point saying it. I am 45 and my manager is 55, and we both ask questions in the way is the Allison has suggested to the OP. I really dislike people tagging stereotypes to generations when it’s really not true.

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        1. E.

          I disagree that there’s no point in saying things that don’t apply to all people – NOTHING applies to all people!

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          1. Random

            Saying something is generational when it does not apply to all in the generation and it happens to apply to people of all generations doesn’t make any sense.

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            1. Emily K

              I think sometimes it can be helpful to contextualize why (npi) someone does something that seems strange to me. Like, “This strange thing is much less strange/more common among X group that my bizarre colleague is a member of.” A lot of how I think about and deal with something in the workplace is related to whether it’s normal and reasonable (I should be prepared to deal with this in the workplace and this person isn’t doing anything that deserved my ire) or weird and unreasonable (I can push back against this).

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            2. Lissa

              Disagree. No trend applies to every last person, but it doesn’t make it not a trend. There are reasons why certain traits are more or less true of some ages/generations and I think it’s only a problem when people try to make it a value judgment or apply it to everyone, which I personally didn’t see at all.

              Then again I’m a nerd about this sort of thing and find these conversations pretty fascinating! It might not apply, but it’s really intriguing to look at it. It’s a lot like regional differences to me. You can’t say ALL people from NYC are different from people in midwest, but if you’re moving from one to the other it can be useful to know some differences that are likely to apply. (not American but I think those two places are widely considered to have different social norms!)

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              1. whingedrinking

                I agree. I work with international students and a key part of doing the job well is understanding cultural differences. This isn’t the same thing as saying, “Japanese students all hate being asked to speak” or “Brazilian students are always late”. However, it can give you a better understanding of where people are coming from if you acknowledge that in Japan, it is less common for students to work in groups, or that Canadian norms about punctuality are more stringent than Brazilian ones.

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            3. Courageous cat

              Well, I think whether or not something applies to an entire generation or all generations is going to be subjective no matter what, so you’re never going to be able to say any of that with certainty. Which goes back to it being ok to make certain (more harmless) generalizations as long as there’s an understanding that they’re your own.

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      4. The Doctor

        Then there is the type of boss who wants everyone to know how high to jump AND to have already jumped that height —BEFORE he even says to jump. (If you have to ask how high, then you are incompetent and disloyal.)

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        1. boo bot

          I mean, if you wanted to succeed in this job, you should have gone to the future, seen what he was going to have wanted, then gone back into the past and have preemptively done it.

          How hard is that?

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      5. Whatsinaname

        Hmmm, I would really hesitate to ascribe certain behavior to specific age groups. I’m a baby boomer and I definitely need context, so throughout my career I’ve asked lot’s of why’s. It drove some people crazy but I need to know the big picture. I’m also someone who likes to question the validity of doing things a certain way especially when I get an answer of ‘we’ve always done it this way’. I parlayed my inquisitive nature into a career by becoming an analyst.

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      6. SusanIvanova

        I want to please my software users, so when the PM with the cross-platform perspective says “jump”, the right answer is “why?” Because the KangaOS users like jumping, but the iMole people prefer tunnels.

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      7. TardyTardis

        Boomers know how hard it will be for them to find a new job if they’re fired (but of course there’s no age discrimination, right?)–millennials know they have more time and are more likely to be hired. Boomers also face more problems finding health insurance should they be fired.

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        1. NotAnotherManager!

          It’s cool, we’ve always been ignored – sometimes keeping a low profile has it’s advantages. I’m going to turn on my grunge and go back to slacking now. :)

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          1. Noah

            Gen Xers are sooooo under the radar, from President Obama to Kurt Cobain, from to Tim Cook to Public Enemy, from Quentin Tarantino to Wayne Gretzky, Gen Xers don’t seek out fame at all.

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            1. Duchess Consuela Banana Hammock

              Slightly OT but Barack Obama (b 1961), Tim Cook (b 1960), the members of Public Enemy (b 1959 and 1960), Quinten Tarantino (b 1963), and Wayne Gretzky (b 1961) are all late Baby Boomers.

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        2. Falling Diphthong

          *bwa ha ha ha ha*
          *we are stealth ninjas creeping through the air ducts of your building*
          *you ask ‘where are the bagels’ and it’s because we popped out of a ventilation shaft and ate all your bagels, but you will blame Bill from Accounting*

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        3. RVA Cat

          Gen-Xers are split between “Might as well…jump! Go ahead and jump!” and “Kris Kross’ll make ya Jump! Jump!”

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          1. Persimmons

            I guess that also means that we’re halfway between “pull your pants up” and “your pants are on backwards”.

            Also, go #TeamSammy.

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          2. NotAnotherManager!

            More like “jumping is pointless and futile, but you’re paying me to do it, so I’m going to jump as efficiently as I can without drawing undue attention to myself.”

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          3. Tongue Cluckin' Grammarian

            I nearly spit out my tea at this. I never felt more affirmed and called out at the same time XD

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        4. RandomusernamebecauseIwasboredwiththelastone

          Nah… don’t feel sorry for us. While the boomers and millennials duke it out we will silently take over the world.

          Mwhuahahaha

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        5. Hills to Die on

          As a GenXer, I am the queen of Why. I use it to learn, and I have found I need to change my phrasing also. Over time and experience, my Whys are more sophisticated, more in-depth, and less frequent. But yes, there are plenty of times over the years where I have had to explain that I am trying to understand and not question. Once people know that about me, things are much moire comfortable and communications are smoother.

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        6. Just Employed Here

          I was born in the late 70s, and we don’t even fit into any of these categories. We were still teenagers when the book Generation X came out and described disillusioned 20 somethings who had already graduated.

          So we’re really undercover.

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      1. Bea

        My boomer parents taught me to challenge authority and ask why if I didn’t know the reason someone wanted me to do something. Granted they are also the stubborn sorts who loathed to be told what to do. I rarely heard “because I said so” growing up needless to say.

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    2. boo bot

      “I would ask why because I was trying to learn and better be able predict how I should respond next time a similar situation arose. With the help of my current boss we figured out it was how I learned…”

      … Isn’t that just how learning works?

      Genuinely not trying to be snarky, just… a little surprised your bosses seemed to consider this such an arcane, millennial-invented process.

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    3. Ask a Manager Post author

      I don’t know if I agree it’s generational. (I also think we can’t protest against generational stereotypes when they’re negative but accept them when they’re positive.) I’ve worked with people of all generations who ask “why” a lot. Some do it in an excessive, annoying way and some do it in a constructive, useful way. It’s true that people newer to the workforce are less likely to know how to get the tone/wording/timing exactly right, but that’s a function of them being less experienced, not what generation they’re part of. (And I don’t see 30something Millennials doing this any more than anyone else — by the time you’ve got a decade of work experience, you generally figure out the norms.)

      Reply
      1. give me something I can use

        Sounds like Faith’s boss(es) think it’s generational – Faith themself reserves judgment, in my reading.

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      2. OfOtherWorlds

        I’m 35. My mother told me that she always tried to give a positive and encouraging response to all of my “why” questions because her own mother shut down her “why” questions and it felt terrible. So I grew up feeling OK with asking “why”. I don’t know if that’s a universal experience for people my age, but I’d be interested in finding out.

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        1. Cheryl Blossom

          I don’t feel like that has to do with age, I feel like that has to do with parenting styles– people have been reacting to how their parents parented them forever.

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          1. Lissa

            Yeah I think a ton of generational trends are in response to whatever the current parenting style tended to be – there would be outliers both with parents who parented that way, and also people who responded opposite to said style, but that makes way more sense than “a whole generation of people just randomly started behaving in X way.”

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    4. Dr. Pepper

      I think it’s more conditioning and your basic temperament. My FIL was in the military and does NOT like his orders questioned. He wants to give commands and have them obeyed. I’m exaggerating but that’s the gist of it. If you ask questions, he gets very huffy. But then there’s my father, who questions everything and asks “why” all the time. He would definitely answer the command of “jump!” with “why?” and he’s no millennial. He will happily explain why if you ask, and often even if you don’t. Both my husband and I are big on “why”, we *need* to know, despite being raised by very different people.

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      1. Falling Diphthong

        From a long-ago history class, after the Revolution the French military briefly experimented with the idea of democracy in the unit, but it turns out no one thinks it’s a good idea to charge the hill. The military is a good example of where you will often be in a circumstance where you need to react fast, and having that be instinctive can be critical to the mission, or save lives. (Or cost them. But I think on balance there’s more circumstances where “Duck!” or “Jump!” means “before the flying piece of metal which I can see coming at approximately this heading and speed intersects your throat.”)

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        1. GlitsyGus

          “So, team, should we charge the hill?”
          “I dunno, Sarge, the last time we did that a lot of us got hurt, and we didn’t even take control of the hill in the end. I don’t really want to get hurt today…”
          “Bob’s got a point, there, Sarge.”

          It is definitely a circumstance thing, I worked in a factory for a little while. In that case asking why wasn’t exactly a bad thing, but more often than not taking too long to explain something would gum up the works down the line and mess up a lot of other people’s work, so you tended to keep the questions to just what you needed to do your part right now and save the big picture questions for later.

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      2. Indigo a la mode

        Well, this kind of hits on what Alison was saying about knowing your audience and knowing how to clarify without sounding insubordinate or suspicious. Efficacy in the military relies strongly on people following orders without question. Of course there’s a difference between “Private, go dig a one-inch trench between the lawn and the sidewalk” at Basic Training (been there) and “Private, FREEZE” in a war zone, but it comes from the same place: getting soldiers to a place where, when a split second is the difference between life and death, you automatically follow your training/orders.

        In some situations, there’s room for suggestion or negotiation, but largely you can expect the military to have a culture of regimented chain of command where what the top says goes, and resisting that well-known culture is unlikely to end well for the rebel.

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    5. Cheryl Blossom

      I don’t think painting this as generational is helpful. Some people like asking why and some people really don’t. I’m a millennial and I’ve always hate, hate, HATED when people constantly needed to ask why some rules or procedures or anything are the way they are. Sometimes it really just doesn’t matter, and asking why just slows the process down for everyone else.

      (I always got mad at kids in math class who asked “why” when the teacher introduced a new principle. It’s math! Can’t you just memorize the rules? I guess knowing why the rules are true must have helped them learn somehow, but it was always so frustrating to me…)

      Reply
      1. Ex-Academic, Future Accountant

        About the math thing: Hmm, really? I can see if they were just continually asking “why?” like a toddler without clarifying *why* they were asking, or if they were asking questions that they could just Google on their own time, that that would be annoying. Or those people who have to get into a big long argument with the teacher/professor in front of everyone just to prove that they were right or how smart they are, or in order to show up another student — I hate it when people do that; they’re demonstrating that they have a total lack of respect for everyone else in the room such that they’re willing to waste everyone’s time for something that only benefits themselves.

        But I think there’s a huge difference between those things and good-faith attempts at further understanding. I am terrible at memorizing, but pretty good at remembering things that are important in some way. Knowing the logic behind the steps to solving a particular math problem is much more useful to me than plugging numbers into a procedure that seems opaque, or being able to rattle off the formula (which I may just forget again after the exam). If I understand the thing more deeply, then I’m gaining a tool that I can apply to other things later. I haven’t formally studied math since high school, but this has been my experience in other quantitative or sciencey fields.

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        1. Cheryl Blossom

          It was a constant stream of interruptions in the middle of classes about why we knew that such and such thing was true. I don’t know, math is super opaque to me and explaining the logic behind it (especially at levels higher than algebra, like precalc and calculus!) often made it make less sense to me rather than more.

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          1. All About That Why

            Okay, I’m a math teacher. I *want* people to ask WHY? For two reasons: If you only memorize the “how” to do things, it’s immediately forgotten. And, additionally, “why” helps you see the reasoning behind things like fractions and where it fits into the big picture. In college math classes, I asked “why” because I needed to see how this part fit into the greater whole. I am not someone who can learn step-by-step: I have to see where I’m heading to know where it fits in. This is true even though I am a math teacher learning Calculus (and my current professor, a colleague, refuses to tell me “why”,which makes me glad the internet has come along since high school.) A good math teacher would know how to limit the interruptions, or incorporate them automatically into the lesson.

            Off the soapbox.

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            1. whingedrinking

              Also a teacher (of languages) and yes, how much context makes a difference is a very individual thing. I’m definitely more of a big picture person. One of my majors was in philosophy and I remember finding Leibniz to be completely impenetrable until a kindly grad student gave a tutorial on the Monadology. He explained what Leibniz was trying to prove, which philosophers he was responding to, and why the damn thing was written as a lengthy logical proof in the first place – and suddenly it all made sense. Other students found this tutorial to be a waste of time because only half of it was directly about monads.

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          2. Ex-Academic, Future Accountant

            Yeah, if it was that incessant, then I think it mostly sounds like a failure of self-regulation on the part of the students and one of classroom management on the part of the teacher. The students needed to learn that monopolizing class time is not a good thing and does not make people think better of you, and if you’re really interested then you can talk to the teacher privately. Ideally, the teacher would be saying things like “that’s a great question, but we don’t have time to talk more about X today, we need to move on to Y” and then suggest some additional resources, and/or come back to it later if it’s one of those classes that has time budgeted at the end of the year for “special topics” or whatever.

            Some explanations went way over my head — my precalc teacher once did this trigonometric proof of e^iπ = -1 using the unit circle and drew all this stuff out with one of those big goofy chalkboard compasses and everything, and it was really complex and I wouldn’t have been able to explain it step by step afterward, but I’m not sorry to have seen it because it was really cool. And I bet if I were to look it up now, I’d understand it better than I would if I were seeing it for the first time.

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          3. nonegiven

            I couldn’t remember all the formulas, but if I understood why it was that way, I could derive the formula on the test and work the problem, anyway.

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      2. Shad

        I was always a student where understanding why/how made learning stick better. But figuring it out myself, and especially explaining it to someone else, always helped more than even being told why, so I’d always rather either work myself through some problems to understand it or ask a question framed as “is this why?” than just an open ended question.
        To whatever extent that’s possible, even a wrong guess for such a question might be effective as a signal from LW that the question comes from a desire for deeper understanding rather than combativeness or insubordination.

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    6. What's with Today, today?

      I’m not sure this is totally generational. I was coming to comment that my co-worker is the queen of asking WHY. She questions everything, usually a few times, but she’s a boomer.

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    7. Princess Consuela Banana Hammock

      I don’t think it’s generational—I think it’s experiential (i.e., the more experience, the easier it is to figure out when asking why is appropriate).

      OP may want to consider explaining their learning style to their boss. For example, I’m someone who needs to understand the big picture before I can hone in on a narrow question. So I tell my bosses that that’s my approach, and then they’re less frustrated when they see me spending time trying to understand the big picture (when what they want is a memo on the narrow question). Tempering their expectations may buy OP more leeway with their manager, and it might reframe how the manager perceives OP’s “why” questions.

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    8. Merula

      I had a line-sitter boss (born 1979) once tell me that he appreciated my questions but that they would hold me back because “millennials are always asking these things, so it seems unprofessional”.

      I pointed out that I asked “why” questions approximately as often as my boomer coworker who was older than his mother, and the reason behind the questions for both of us was that most of the time we were charged with explaining new things to customers, who are inevitably going to ask “why”. We were both anticipating what we would need to know to implement the changes as requested, while our silent coworkers were more likely to either tell customers “I don’t know, that’s corporate for you” or just ignore the instructions altogether.

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    1. Sabine the Very Mean

      Yeah. My counselor tells me that starting a question off with ‘why’ immediately puts a lot of people on the defensive. Find a different way to ask.

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      1. give me something I can use

        I get a lot of mileage (I think!) from prefacing responses with ‘Hm.’ It leads equally well to “I need more info” and “If we do X, then Y”, and lets me silently get past my kneejerk snark or jokey responses.

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        1. Lil Fidget

          I do “ah,” (thoughtfully, while nodding) or “I see,” and then pause, before I start a discussion. Hopefully it demonstrates that I wasn’t just waiting for you to finish before I launched in.

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      2. TootsNYC

        definitely craft some wording.
        “What’s the goal for this?”
        “What kinds of things did you factor into your decision?”
        “Which part was most important?”

        “Can you explain a little more? This fascinates me.”
        “Could you let me in on some of the reasons? It might help me be more effective next time.”

        “Would you tell me your thought process, so I can channel you better in the future?”

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        1. Jadelyn

          I’m a huge fan of “Could you clarify…?” myself, and “Just so I can be sure I’m understanding…” – enough deference to not come off as a challenge, at least when said in a genuinely open and inquisitive voice. If there’s resentment or frustration in your voice, though, all the wording in the world won’t help.

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            1. TardyTardis

              Yes, I think this reframing is good. Back in ancient Rome, Tiberius (pre-Emperor) was known as a serious hardcase, aka General Flogger. But he still (at least per I, Claudius) said that anybody from centurion on up who did not understand a set of orders prior to a battle was really really really welcome to come to his tent so he could clear up any misunderstandings (I believe he gave awards to some of them who did just so they knew it wasn’t a trap).

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      3. Hamstergirl

        Yes I completely agree – I think “why” tends to have the subtext of “I need you to justify this decision”
        Whereas I also find more specific “what” questions that get to the root of the “why” are better – for example “what are our ultimate goals for this project/task?” or “What kind of flexibility do I have with this timeline?” or “What kind of information are we hoping to gain from this meeting?” etc. they have the benefit giving you more context than just a “why” and will ultimately arm you with better information to complete whatever it is you need to complete.

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        1. Kelly O

          “Why” is what my seven-year-old says.

          We are working on teaching her that sometimes it’s better to say “I don’t understand why we do X” or “What would happen if we did Y instead of X?” – framing the question in a less confrontational way.

          It’s easy to sound patronizing when adding “hmm” or some other filler word. Just take a moment and come up with a complete sentence/thought, and then make that your question.

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        2. Princess Consuela Banana Hammock

          I agree. Even if the question is, “Can you help me understand why we’re doing this?” or “Can you help me understand the logic/reasons/needs so that I can craft a better deliverable?”, it will usually go down a little better than a straightforward “why.”

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          1. yasmara

            I agree 100%. I couldn’t put my finger on why “why” was bugging me so much, but I think that it seems simplistic/juvenile/lacking in nuance but also confrontational, especially coming from a subordinate to a boss. Whereas a question that points to something specific that needs more explanation or turns it back around to the subordinate not understanding is more appropriate in this context.

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    2. Lil Fidget

      I was thinking that too. One consideration is the situation, a second is the specific phrasing, but a third very important one is tone. Also, I think you need to convey that you understand that your desire to know more is secondary to the goal of getting the work of the office done. If that is backwards, could be part of the issue. (Or the boss is a jerk. Hard to say).

      Reply
    3. Drago Cucina

      Yep, timing and context. We’re trying to get the staff to tell us what policies they need to know the “Why?” behind so they understand and can help better explain them.

      If they ask me as I’m running between meetings (which can overlap) it may sound like, “Because of privacy.” If they say in meeting, “We’re often asked XYZ. Can you tell us more about why this is the policy?” I’m better able to explain. “The law in this area states LMN. So, we can’t legally do XYZ.”

      Reply
  2. Xarcady

    If what you really want to know is how everything fits in and fits together, ask that! Instead of why, ask, “How does this report fit in with our other reports?” “How will this change affect the XYZ process?” “I’m not sure how this new report is different from our regular monthly report. Can you explain that?”

    I get you, OP. I need to know how things fit together, so I can make good decisions when I need to, when something doesn’t fit our usual parameters. And I too have been accused of asking too many questions. I started focusing the questions more narrowly–“Our client wants X and we can do that, but will making that change affect the final stats report?” is received better than, “Can I do X for this client?” and leaving the person I’m talking too wondering, yes, of course we can do that, why are you asking?

    Reply
    1. Hey Karma, Over here.

      That’s great. Asking specific questions is going to help everyone. Either you will find other people have the same question (thanks for speaking up!) or nobody has that question (hey, we didn’t loop you in earlier!) Win win

      Reply
    2. LaSalleUGirl

      Long ago, when I was an English major temping for the investment division of a major bank, I figured it was my one and only chance to really learn about investing and performance. I gave myself a goal of asking one serious question per day (what the heck is a hedge fund? what is short selling? why ISN’T it a good thing to dump your stocks when the market tanks?).

      BUT: I told my colleagues upfront that I was going to do this because I wanted to learn, I tried to read the room in terms of when people had capacity to answer me, and I told them that it was totally OK to tell me “Not now.”

      I think the LW’s reasons for asking “Why” questions are great, but those reasons might not be obvious to the boss. It might help to explicitly frame them as part of a bigger “I like to know how things work and how the pieces fit together” project to avoid having them perceived in the moment as challenges.

      Reply
      1. mark132

        I think there is a difference between why (please educate me), and why (I disagree with what you are doing yet again).

        Reply
        1. Blue

          Newness also makes a difference here. If OP is fairly new in their role, explaining the “why” can be worth the time investment because they’ll have a better grasp of their work moving forward. If they’re asking a lot of the please-educate-me type of “why” questions but have been there for a while, that’s can be just as problematic as a challenging “why.”

          Reply
          1. Genny

            That’s a good point. There’s an element of learning here. If you’re always asking about some aspect of the teapot spout report, it sounds like you aren’t learning or are trying to question authority. If you’re asking about a variety of things and incorporating the answer you get into your performance, that’s definitely acceptable.

            Reply
            1. Lil Fidget

              Yes, and your “why” is disingenuous if you’ve been here long enough that you know the actual reason but you’re actually just using it as a starting point to rebut the assignment.

              Reply
          2. sb51

            On the flip side, if they’re VERY new, getting into all the why’s can be information overload when what you need is for them to concentrate on getting the hang of the basic processes, and once they understand the day to day, then get them up to speed on how to improve the processes/contribute at a higher level.

            Reply
        2. Amber T

          Yes – my boss (who is new to our office and his specific role, but not our industry), prefaces a lot of his questions with “For my own edification, why do we…?” He does this with his his own boss, his peers, and those he manages, so he makes it clear that he’s asking for clarification on how we do things. It’s part of his job to make changes and improve things (which he’s done and is doing!), but it’s never felt condescending or uncomfortable when he asks why we do things the way we’ve done them or suggests changes.

          Reply
    3. Anon Asst

      Plus repeatedly asking “why” sounds almost like a four year old. I can see how it would wear on boss’s nerves.

      Reply
        1. Guacamole Bob

          The frustrating part of dealing with my four year old’s why questions isn’t that they’re petulant, though. It’s more of a “this is a trivial thing that doesn’t really have an answer and there’s not really a bigger picture here” frustration. Like, this morning my son wanted to know why there were two necklaces on the shelf in the closet, and asked like six follow up questions trying to understand how this state of affairs came to be, when I’m trying to get ready for work and there’s no satisfying answer to the question besides… because Mama put a couple of her necklaces on that shelf at some point? Months ago? I don’t really know, and who cares?

          And he wants to know exactly why all road sign designs are what they are. And to some extent it’s good and interesting and productive that he’s learning how people communicate things through pictures, but sometimes the answer is “because that’s how someone decided the sign for the start of a median in the road should look.” And that bit of a building he’s asking about looks that way because someone decided it should, and I don’t know why, and it doesn’t really matter. Maybe they thought it would look pretty? On and on throughout the day.

          He’s a little kid figuring out the world, so he doesn’t know which questions are fruitful and important and which aren’t. By the time you’re an adult in the workplace, you need to develop a bit more judgment about what kinds of “whys” will help you understand your role and your work better, and which will just drive your boss up the wall.

          Reply
          1. jd

            When it comes to little kids and learning, redirecting their questions into an introspective process of self-inquiry can be super helpful. “I don’t know that one, kiddo! Why do you think that is?”, and let the imagination fly. Unfortunately I don’t think that’s transferable to grown-ups in the workplace.

            Reply
            1. AK

              I think it depends on the context of the original request though. This is a ridiculous example but bear with me- If my team’s job is sorting widgets into boxes based on color and I’ve explained that the red ones need to go in the red box because some people only order red ones, it can be a fair scenario to reply to “why do we sort blue ones?” with “knowing what you know of what we do and why red widgets are sorted, why do you think we sort blue ones?” Adults can be guided to finding answers themselves in ways that kids really can’t, since adults can do their own research and (generally) deeper thinking.

              Reply
              1. Antilles

                Managers need to be pretty careful how they do that in the workplace though, because there’s a really thin line between “teaching by asking questions / guiding them to figure out the answer themselves” and “ugh, this is ridiculous, just answer the freakin’ question”.

                Reply
                1. Jadelyn

                  Plus “teaching by asking questions” can come off patronizing as hell, if it’s not done with a great deal of care and tact.

            2. Guacamole Bob

              I do try that, and only some of the time does he scream back at me “I DON’T KNOW! YOU KNOW THAT!”

              Kids, man.

              Reply
          2. mark132

            I was thinking more of the “why do I have to do this”, or “why are we going here” more of the whining why rather than the curious why. But you definitely have a point.

            Reply
          3. Liet-Kinda (nee Snark)

            Like, this morning my son wanted to know why there were two necklaces on the shelf in the closet, and asked like six follow up questions trying to understand how this state of affairs came to be, when I’m trying to get ready for work and there’s no satisfying answer to the question besides… because Mama put a couple of her necklaces on that shelf at some point? Months ago? I don’t really know, and who cares?”

            NAILED it. I have never felt more understood. “Dada, why is there green chile in green chile stew?” “Because that’s what it is. It’s got green chiles in it.” “But why?” “Because…someone decided to put green chiles in their stew one day and it was good and everybody started doing it that way.” “But why did they do that.” “Because…gah…green chiles are delicious.” “Why are they delicious?” “OH LOOK ITS YOUR TABLET WANNA WATCH SOME PAW PATROL”

            Reply
            1. Lil Fidget

              Also my niece and nephew definitely use this technique to get out of doing what they’ve been asked (go to bed, clean up their toys, take a nap) so it’s hard to take it at face value after a while!

              Reply
              1. Falling Diphthong

                Yeah, sometimes it’s absolutely a routine “push this button to retain adult’s attention; let response flow right over your ears” or “push this button to stall enough times and maybe you won’t have to brush your teeth.”

                Reply
              2. TardyTardis

                My husband’s students would do this, and he’d go along with it for a while, and then he’d say, “Guess what, you used up all your spare time to do homework in class, hey, that’s the bell…”

                Reply
          4. TootsNYC

            little kids also ask “why” because it’s a reliable way to insist that a grownup have a conversation with them.

            Reply
    4. Xarcady

      And here I am replying to myself. Here’s a real-life example. At my part-time retail job, the chain has just started a new way for customers to pay, using their smart phones. The change was rolled out three weeks ago. Because I’m part-time, I frequently miss the morning meetings where these sorts of changes are discussed.

      I have run through a purchase with the new system, which is apparently more than any of the managers have done, as none of them could help when I got confused.

      But now I have about 4 questions that are tangential to the new process–they involve putting a hold on something, can we keep these items at the cash desk , can the customers use any register or only the one with the big sign hanging over it–things that were not covered in training.

      From experience, I know that there is one manager I could ask all the questions to, but if he’s not around? I have to ask one manager one question, and wait, possibly days to get an answer. Then ask another manager one more question and wait for an answer, or even, “No one knows.”

      I have to tread carefully on new systems, because most of our managers never test them out, have no idea how to use them and don’t know how to find out the answers. If I ask too many questions they can’t answer, some of them get upset. All I want is the info to do my job. Corporate writes truly terrible instructions and my store managers are too over-worked to test them until a customer is standing at the register, screaming at someone. And I’m not in a position to change this.

      Reply
  3. LadyL

    I just got in trouble last week for asking too many questions, so this felt very timely. I feel you LW, I don’t pick up on subtext well so I really feel like I need to ask direct questions to understand things.

    Reply
    1. Not Tom, just Petty

      I’m a talker and I get really excited when I figure out the big picture and tended to blurt, oh! so we will need X and Y or Oh, but what about A and B? We’re getting there. (Yes, I can get excited about work. I feel so old!).
      I learned to limit comments (1 every 15 minutes, so twice in a half hour meeting – it’s hard!)

      Reply
        1. Hey Karma, Over here.

          You’d think it’s intuitive, the less you say the more importance people give it. But man, all those participation points in school really do a number on people. First one to shout the answer, first one done with the quiz…It’s really hard to change. And to admit that you are the annoying coworker!

          Reply
      1. Lil Fidget

        Yes I loooove to talk and discuss ideas and get big picture and figure out the strategy (especially as in my field, there often is not a strategy and we’ve just inherited crappy systems that we feel beholden to). But, there is a place and time for that. It is not all the time. If you are always adding extra mental load to what should be simple tasks, you are not going to endear yourself to your manager. I have to repeat this to myself daily lolsob.

        Reply
  4. Hey Karma, Over here.

    Yeah, I’m with Alison on this one. It’s not the “why” its the how and the when. How are you asking? When are you asking? Look at yourself first and determine what you need/want from asking this and then discuss with your manager how to get this in the future.
    Look at it this way. You want to know why your manager said you ask why too much. She didn’t give you an explanation with this and you couldn’t think of a way to ask her. There’s the communication problem right there. You don’t know how to communicate with each other. This is a chance to change that, to build a functional working relationship where your manager doesn’t feel like you are bombarding her with unimportant or aggressive questions and you get the information you need to do your job. Even if the answer is, “because I determined that’s the best way for now.” Now the question is, will that answer be enough for you? Again, determine your goal here.

    Reply
    1. Aleta

      It’s how and when, but also how much. Even super reasonable questions asked reasonably can be grating if they’re extremely frequent. I definitely have toddler-style “why? why not? why? but WHY?”-asking parents for every little thing and even if those questions are reasonable on their own, in aggregate they’re EXHAUSTING.

      Reply
      1. The Cosmic Avenger

        And if the frequency is an issue, the manager might think the OP is asking without trying to figure out the “why?” themselves. I know the OP said they felt it was an issue of challenging their manager’s authority, and I’m not going to contradict them, but they might certainly be able to cut down on their need to know if they consider 1) how much it might impact their work product to know the “why?”, and 2) is the “why?” something they can seek/study on their own, without sidetracking their manager.

        Reply
        1. fposte

          Yes, I think it’s important to remember that this is asking for the manager’s time, not just the information, and that managers have a finite amount of time; filling people in on backstory isn’t always going to be a priority.

          I mean, I’m in education so we’re all about the why, and I fill people in a lot (sometimes even when they don’t necessarily want to know :-)). But there are why questions that I’d probably deprioritize, especially if they’re procedural questions about big institutional or state-level stuff. So the OP might also look around to see how much “why” her co-workers are asking and check if she’s taking more time than is expected with those.

          Reply
        2. Falling Diphthong

          I think it’s reasonable to sometimes push back on “this is what the other person was thinking when they said this” from OPs.

          That can slide over into doubting people on a tone that is in fact there (like you can say “Hi” in dozens of ways), but in a lot of cases it’s one of the points of bouncing a behavior off a bunch of other people–they come up with a variety of contexts in which this result might occur. And putting it into a different context might make it less annoying, or give you practical ideas on how to respond.

          Reply
        3. TootsNYC

          , the manager might think the OP is asking without trying to figure out the “why?” themselves.

          This gives you a powerful tool!
          The things we figure out on our own are the things we learn most powerfully.

          So try to figure it out yourself, and then if you’re uncertain, go check at some point (tell them you want to check some of your assumptions as part of a self-training): “It seems you used this word because the other one is so emotionally loaded–is that what you were thinking?” And they can say, “Oh, no, I’m happy to be emotionally loaded, it’s just that I think the old one was too many syllables.”

          Reply
          1. Jadelyn

            It’s also much more likely to be well-received when someone says “I looked at X process document and did some searching online for answers about Y, but I wasn’t able to find much – can you clarify why we use Y for X?” because that indicates they’ve tried to respect your time by figuring stuff out themselves rather than just expecting you to drop your own work to be available for storytime whenever they want.

            Reply
      2. RandomusernamebecauseIwasboredwiththelastone

        Agreed with you and Hey Karma. Productive ‘why’ questions are great they show me someone is engaged, wants to learn more, and is generally trying. Pick your time, topics, and quantity and you (OP) too could have productive ‘why’ questions.

        Non productive ‘why’ questions make me want to douse someone in chloroform. There are some things that don’t need an explanation, there are some things I won’t be able to give you an explanation, there are some things I’ve already explained, there are things that I will explain just not that second, and last but not least there are some things you should be able to figure out on your own.

        I don’t think this is a generational thing, I think it’s an experience thing. Remember the boomers where the original ‘challenge authority’ generation. They were just as likely as millennials or Gen Zs to ask these types of questions… difference is now they are old enough that they have the experience to know when, where, and how it’s appropriate. lol I’d argue that Gen X’ers didn’t bother asking, they just decided to do as they were told or what they wanted without asking. In about 20 years the millennials and Z’s will be complaining at all these upstart young ‘s questioning everything they do.

        Reply
    2. LKW

      Also consider whether or not you’re putting the burden of explanation on your boss or if you can try to fill in the picture and have her fill in small gaps.

      Ex 1: “So I need you to complete this task first and then this one followed by this last step.”
      “Why?”

      Ex 2: “So I need you to complete this task first…”
      “Oh, so the information from task 1 becomes an input in to task 2 and then I can confirm the accuracy of step 3 because I’ve noted, a, b, c”

      If someone asks me “Why” – especially if they are junior -I often turn that back to them and ask them what they think the reason is. Now, obviously, sometimes they can’t answer, there may be legal or compliance reasons they wouldn’t know without experience, and I’ll fill in.

      Reply
      1. TootsNYC

        , the manager might think the OP is asking without trying to figure out the “why?” themselves.

        My mother did this to us!

        Reply
    3. Tequila Mockingbird

      Basically echoing what Alison said – it’s not the intent behind the question “Why?” (a request for more information/context) but rather how the question itself is posed. OP should try fleshing out her request in the way Alison suggested, because the word “Why?” standing alone comes across as argumentative. And if OP is saying the word “Why?” a lot (several times a day), yeah, I could see that as really irritating.

      Reply
    4. Lexi Kate

      Yes, If you are just saying why then it comes off as you are my 3 year old that says why to everything. Where if you are posing it as a true question with some background then I feel like you are asking to move forward.

      Also there is a right time to ask why in a meeting where you are not explicitly there for that topic is not always the right time for asking why.

      In general I love that my workers ask for more information, but not when its going to take over another meeting or doesn’t have enough relevance for the room or when its just ‘Why’.

      Reply
    5. Jenn

      I have to agree. Is this “Why (so I can better understand this for future reference)” or “Why (please justify your actions to me)”. In practice the difference can be subtle, but crucial. This can mean instead of “why” be more explicit as to the reasoning behind your question.

      Also, accept that you may not get all info. There may be policy reasons you can’t know why. You have to accept it graciously.

      Reply
      1. Lil Fidget

        Sometimes it’s also better to posit a guess. “is this because the teapot manager needs to see the specs before they can sign off?” That makes you sound more engaged and thoughtful, and can reveal an important gap in your understanding – and at least you tried to do some of the work for your manager.

        Reply
      2. Turtle Candle

        This is key, I think. We had a new graphic designer come in to take over a team some years ago, and whenever we’d go over things that needed to be updated, she’d say “Why did you do it that way?” Which is a valid question, but the answer was “because the last designer recommended it.” (The rest of us are engineers, and generally defer to the designers on design questions unless there’s a specific implementation reason not to.) “But why did she recommend it?” Um, we don’t know, it was five years ago and we either don’t remember or didn’t second guess–but you can change it if you want, that’s why you’re here. “I’m just trying to understand why you’d do it that way.” Etc. It really would begin to feel like the underlying question was “Why were you so stupid as to do it this obviously-wrong way?”

        After a while, we didn’t even need to go all three rounds of ‘why’ to feel defensive, because the pattern made every ‘why’ question feel like a ‘justify yourself to me, dancing monkeys!’

        Reply
        1. Lil Fidget

          It would have been much more helpful for this designer to just offer their own suggestions and see if you’re open to them, rather than trying to re-litigate an original decision. “What would you think if I moved the header up and made it purple?” would be better than “why is the header so low? why is the header green?”

          Reply
  5. Monty & Millie's Mom

    I agree with this answer! Based on the original letter itself, it does seem as though the OP could be coming across a bit like a toddler asking “why” all the time, which isn’t a good look. I would double down on the part where Alison talks about how you are asking for further information. If it’s more a discussion, not an interrogation, your manager may be more willing to engage and explain more.

    Reply
    1. MuseumChick

      That’s the sense I’m getting, not to compare the OP to a toddler or anything! But that is the closest example I can think of to describe what is likely happening here. After being ask “why?” for the 500th time you eventually just say “Because!”

      Reply
      1. Monty & Millie's Mom

        Yes, I’m sorry, not comparing OP to a toddler, that may have come across as kind of mean! My apologies! And there’s certainly nothing wrong with wanting to know things – I believe questions are great! And I don’t even know if that’s what’s happening, just the way the letter was worded made me think of it!

        Reply
  6. MuseumChick

    OP, I think this comes down to a combination of factors: tone, wording, frequency, timing, etc. I get the sense the frequency might be a big factor here. If you are asking “why” questions multiple times a day, that is going to annoy most managers. They are often busy and don’t have the time to explain the “why” behind everything.

    My advice is to try and save most of your “why” questions for when you and your manager have some time to talk. And then you can use Alison’s wording.

    Reply
    1. Detective Amy Santiago

      Plus sometimes the answer might be “because it is”. Some things just are and there aren’t really explanations.

      Reply
      1. MuseumChick

        Yup. When I ask my direct report to do something I don’t want to have to explain all the judgement calls, office politics, any government regulations, etc that went into it. I just want it to get done.

        Reply
        1. Queen of the File

          This is the reason I think a manager in my area would be annoyed by a lot of ‘why’ questions. It would take a year to summarize the background and it’s not going to change the fact that the thing needs to get done.

          That said, if this is the kind of ‘why’ question being asked on the regular, maybe it is worth catching the person up from time to time on how decisions are made and ‘larger picture’ stuff at the organization, so they understand how they fit in and some of the things that go into their work that they may not know about? I could see having a meeting with my manager/team to discuss this sort of thing from time to time if people felt disconnected–provide an opportunity for input, answer questions, hear suggestions for improvements, etc.

          Reply
      2. Gaia

        So many times.

        I worked on this huge project where we had many, many, many decisions where option A and option B both produced the exact same results but it was important that we picked one and that it was consistently either A or B every time task X was done. It didn’t matter that A and B both produced C, if we chose A and you did B it was wrong.

        So many times people would come to me with “but why A, I prefer B” and the answer was literally “because that is what we picked.”

        Reply
        1. TootsNYC

          though there’s the background (if you want to train a rookie, and have time) that “It’s important for legal/compliance/efficiency reasons that the process be identical every time. And so A is the one that got picked, for reasons I don’t know because I didn’t work here then, but now all that matters is that it’s important to be consistent.”

          There *is* a “why” that you can explain that will teach someone a lot about your field and the processes in it.

          Reply
          1. Gaia

            I think the issue is I do know why A got picked because I was the one who picked A but it really was an eenie meenie miney mo situation. Haha.

            I think where people got hung up (understandably so) is if they do process A the result from the outside is C and if they do process B the result from the outside is C and really the only person that knew they did B instead of A is me and without a very technical level of understanding of what we were doing (which none of these folks had) no explanation would have sufficed.

            I totally get their frustration but I was about ready to pull my hair out. I would not handle toddlers well hahaha!

            Reply
        2. Hiring Mgr

          But in your example, the first paragraph explained it far better than your actual answer… If the people didn’t know why it mattered, “because that is what we picked” wouldn’t really help

          Reply
          1. Gaia

            You’d think so, wouldn’t you? But no, sadly not. They want to know *why* it mattered that we had to pick one and *why* it was wrong if the result is the same and *why* we chose that one over the other when they prefer the other. The why never stopped and “because we had to pick one and consistency matters” was never a sufficient answer when the end result was consistent regardless of process.

            Reply
      3. The Other Dawn

        Yes, sometimes it just is. I had a direct report years ago who would ask a lot of “why” questions. It got annoying sometimes, but I knew she was someone who needed to know how everything fit in order to understand why she was doing something; most of her questions were good ones. But there were lots of times when her questions were ones where there just wasn’t an answer other than “that’s the way it is and it has to be done that way because it doesn’t work any other way/the system sucks and we need a work-around/Jane wants it that way/the government says so, etc.”

        Reply
    2. NotAnotherManager!

      All of this! A lot of times, it’s not the question itself but how it’s phrased and when it’s asked.

      I also suggest that people try to ask confirmation or multiple choice questions rather than open-ended one, if they can, too. Using those formats requires that you do a little research and synthesize what you already know, which usually goes over well and makes it easier/less time-intensive for someone to answer your question. (I work with lawyers, and I’m going to get a faster response to, “We will be doing X, correct?” or “Do you want us to do X or Y?” before I will hear back on “What should we do?”. )

      Reply
      1. Lil Fidget

        Yes, I wouldn’t always recommend this, but since OP’s manager has explicitly stated that they want less questions, I might say write them all down and pick the most important one or two in a week for a while. Ask them in the right venue, like a check in meeting. (Usually I would say two questions a week is too low but your boss is probably looking for a noticeable change since they brought it up).

        Reply
  7. Leela

    LW–I feel you!

    I had a manager pull me in for a one-on-one and tell me I was very defensive because I kept asking follow-up questions like this. I don’t think I ever just outright said “why?” but I’d ask “can I get some more info on what the goal is with this one?” or something along those lines. It had happened many times that I’d get an assignment that was for something very, very specific and that was never shared with me, meaning that what I’d produced didn’t work because I didn’t know to tailor it to that purpose. In order to combat this I tried to ask more specific questions when I got an assignment, which she took as combative.

    It was a frustrating double-bind. Don’t ask and you’re probably missing out on key info to do this correctly, do ask and you’re challenging her authority. I wonder if you’re feeling something along those lines? It did end up helping me as far as the assignments go when I asked her if I could message her after our meeting everything I thought the assignment entailed, and she could yay/nay that. She agreed. However, it worsened my work relationship with her because she got very frustrated when I pointed back to what we’d agreed upon and mentioned that the new “rules” weren’t in there, and this is all I had to go on. If your manager doesn’t seem like someone who’d get upset over that, and you’re asking for clarification because you feel like key info comes up after assignments, this might be something to try?

    Reply
    1. ThrowAwayHandle

      I just want to push back on the notion OP needs to be asking a bunch of questions because she would be missing “key info” to do her work correctly if she doesn’t ask her manager a bunch of “why”-type questions.

      A good manager will communicate all of the key information and context you need to do your assignment correctly, and asking “why” questions beyond that point implies you don’t trust your manager to communicate assignments to you properly, which *is* pretty undermining. Maybe it’s true OP’s manager is in fact a poor communicator, but the manager’s sense that OP’s questions are undermining her, in that circumstance, is actually correct – OP is not “just asking,” she’s deliberately presuming the manager has failed to give her information she needs to do her job correctly and proceeding accordingly.

      If this is, in fact, OP’s problem – she isn’t receiving information she needs to do her job – it might be smarter to have a global conversation with her manager about that issue, instead of rules-lawyering about how many questions she can ask and in what format.

      Reply
      1. Leela

        I meant my situation as an example to check against and see if OP was feeling like they were in a double-bind, not a warning for all to heed that they’re probably missing key info if they don’t ask why. Getting written confirmation helped me find where communication was falling because in my specific case the issue ended up being that my manager was indeed not giving me proper info, not because that’s just generally how it is.

        Reply
    2. TootsNYC

      My suggestion might be to start the project and ask questions in the middle, when they arise. Then they can be very specific to the situation, which doesn’t sound like an attitude problem.

      Reply
    3. wherewolf

      I definitely pictured this situation. At OldJob I was often told that the next step is to serve tea to the client, and while I was encouraged to take initiative and could see creativity rewarded in others, every time I did it I was reprimanded/corrected–the teapot is the wrong type, I had the wrong number of servings, the client preferred Darjeeling not Earl Grey… all details I had no way of knowing with my level of inexperience.

      So next time I tried to ask more questions in advance: “What kind of teapot should I use? Does the client have a tea preference? How many servings should I prepare?” However this also frustrated my colleagues, who wanted me to come to them with, “I think we should use the blue teapot, is that correct?” and were bothered by my questions taking up too much time. And I was frustrated because it felt like I had to make up answers just to be corrected with the information I needed. Over time I failed enough times that I could begin to see how experience would shape my knowledge so I would just know which teapot to use. But because that was how everyone learned their job at this company, nobody knew how to articulate the wisdom of experience to others. In the end I got frustrated and left, so I still don’t know what I would do differently, but I share this in hopes it gives you some insight, somehow.

      Reply
  8. A person

    In one job, I had two managers who reacted like this. I explained to both of them that understanding “why” helped me to do my job better. Having an understanding of the big picture helped me plan for responses and questions to the program activities I was responsible for carrying out (this was a mid-level program coordinator position). The managers were my direct boss and the next level boss who was also very involved in directing my work.

    Turns out they were both micro managers who wanted me to follow orders and they saw no need for me to understand.

    It was a poor fit and I moved on.

    Another job I had, the manager bristled at first but warmed up once he understand what was behind my questions.

    I try to lead off now with why I’m asking why, and managers seem to respond much better to that.

    Reply
  9. Redundant Department of Redundancy

    I have a report who asks ‘why’ questions a lot, eg wanting to know why we are doing things a certain way. Most of the time the answer is that we’re a big government body, we can change our processes but we can’t force another department to change theirs. It can get very tiresome having to explain repeatedly that sometimes our organisation is a bureaucratic nightmare.

    Also on the flip side of this I’ve also had co-worker who need to know every single detail of the whole story before they would take on a task. It became such an effort to ask them to do something, that they wouldn’t be given tasks to do. I don’t think they did it to avoid work as they’d then be upset they weren’t given things to do!

    Reply
    1. Not Tom, just Petty

      I work with someone who created a similar situation to this. It’s not that she takes three times longer to do work on purpose, she just takes three times longer to produce the same work. So as a reward for being stuck picking up her slack, I’m offered first dibs on cool projects. She has wondered why. This conversation happened: Me: Because I’ll be able to meet the deadline. Coworker: well, they should just move the deadline and let me do it.
      That never happened.

      Reply
      1. Jadelyn

        How do you even respond to that? Like…the level of entitlement involved is pretty amazing, you almost have to admire it, even if it’s completely delusional.

        Reply
    2. fposte

      Yes, it’s that kind of procedural thing that I wouldn’t have time for. When you work for the state, it’s basically “Forget it, Jake; it’s Chinatown.” It’s like asking why there’s a mountain where the road should be; it’s not going to change the fact that you have to go around the mountain.

      Reply
      1. TootsNYC

        not work, but similar

        On a woodworking forum, I asked once about how to handle/replace the wooden saddles/door sills in the doorways of the rooms of my co-op apartment.

        Someone asked, “Why are there saddles there?”

        I’m like, “Dude, there just are. I didn’t put them there. How is that helpful?”

        also: “Why do you do this?” comes across as a straight-up criticism.

        Reply
    3. Guacamole Bob

      I think this is an important point – you have to be asking about things that will help you do your work better, and not come across as judgmental or, alternately, naive. We have a lot of answers that come down to “because higher-up person X wants it that way”, or “because the regulatory body wrote the rule that way,” or “because that other department is totally dysfunctional.” It would drive my manager nuts if I asked probing questions about filling out forms for IT matters, or got frustrated and pushed back on things that come down to “person X said we have to do this.”

      My manager is great about giving me context whenever he has it, and it’s critical to our work to be able to think strategically about our projects. But he doesn’t have complete information about all the workings of upper management or control over many aspects of the sprawling bureaucratic organization in which we work, so sometimes we have to roll without all the answers.

      Reply
      1. Smarty Boots

        It may be that OP doesn’t in fact know when the answer is likely to be “Because the dean/director/CFO said so” — that is, not savvy about how this particular place works bureaucratically and politically. I’ve been in this office since before the ark was built, so I know that stuff (and I know when to ask a pointed why-type question to make a point), but my less experienced colleagues do not. The OP may be in that situation.

        Reply
        1. Lil Fidget

          This is a good point, especially if OP works in a field that deals with any level of government or regulations. That field requires that sometimes you accept that things just are, and have to be done, even if its not the fastest/most efficient/most logical way of doing things. Not being able to handle that (which is reasonable!) might be a sign you’re not right for that field TBH.

          Reply
        2. TootsNYC

          and the question the OP really wants the answer to may be, “What are the advantages that come with doing it this way?”

          And there may be an answer to that. But it’s not the same as “why do we do it this way?”

          So, consider carefully what you’re asking.

          Reply
  10. Random Commenter

    I have had the problem that LW is describing in some jobs. The way it’s been presented to me is that certain process is being explained to me, and I will ask why things came to be that way. So it would go:

    Boss: so here, we will do A B C
    Me: Oh, that’s interesting. Is there any particular reason you decided not to do D E F instead?

    This distinction is important to me because my role involves a lot of advisory, and a lot of optimizing processes. So maybe there IS a reason why D E F won’t work, or has been tried before, or is too complicated, or if there are reasons why A B C is just better, I need to know. Also because if I don’t understand the “whys” I usually don’t really understand fully what I’m doing, and my performance suffers.

    What I’ve found is that when my supervisors weren’t as confident in their own skills, they’ve taken these types of “why”s as challenges, as if I’m showing off my own intelligence.

    Things I’ve found to work:
    – Soften my tone and my wording like in Alison’s examples
    – Instead of “Why x and not y?”, ask something like “is there any particular reason why x and not y, or was that just a judgement call?” – that type of qualifiers make it clear that it’s fine if there’s no reason, because “no reason” is an explanation on itself.
    – Having a talk with my boss where I explain that my brain is set to look for the explanations, that it’s not for judgement but just for understanding.
    – Letting go, sometimes, and learning which things to take at face value, ask less (again like Alison said).

    And for an extreme solution:
    – Ultimately I got exhausted, quit, and in my current role I’m expected to keep asking questions. Yay.

    Reply
    1. irene adler

      My boss doesn’t read social cues very well. For him, silence is agreement. And if you ask questions of anything he says, that registers as disagreement with his ideas. And he takes offence.
      So I’ve learned to first indicate that I like his plan. Then I ask him if he can suggest ideas for surmounting the hurdles I think I’ll encounter when implementing his plan. You never saw a more eager man wanting to help me resolve the issues that I proceed to list. This is when I get to ask the questions- to clarify things -so I’m sure there is an issue that needs attention. And, sometimes, he comes to the conclusion that the hurdle is not surmountable. Or that his plan might not be the best solution. That’s when I ask if he thinks plan B might work.

      Reply
    2. AMPG

      Random Commenter, I think your point about your role being about advising and optimizing processes is everything here. I’ve been in situations where entry-level employees would interrogate all the reasoning behind a particular process, and while in general I’m all about intellectual curiosity, in these cases the employee didn’t have any input on the process and also didn’t have the experience to know whether the questions they were asking were relevant. At that point, they’re wasting their supervisor’s time.

      Reply
      1. Random Commenter

        Yes, I agree with you about it depending on the importance, and I admit that it’s something that took a while to take a hang of. I was probably the annoying employee for a while there while I was getting the hang of it, for sure.

        To add, another strategy one can do is if it’s not important but I’m really really curious, I’ll save it for a time when no one is busy and I can ask informally. Then go very casual about it: “just out of curiosity, I was wondering about..?” just as a topic of conversation. That one has also worked to not be so annoying. But for sure you also can’t use it with every little thing.

        I was probably the annoying employee for a while there while I was getting the hang of it, for sure.

        Reply
        1. Lil Fidget

          Yep. I have to do a mental checklist: why do I want to know, is it mainly for my own curiosity? Does this question have to be answered right now for me to proceed, or can I probably circle back later if I’m still wondering? Is there another way I could get this information instead of making my manager explain (what have I already tried, is it nothing?) and last, would I have any standing to suggest changes to this process if I *did* identify alternatives? I should really only ask the question if all the answers point to ASK.

          Reply
  11. Ms. Meow

    I’m a “Why?” person, too! I like to know how my piece fits into the bigger picture. But to add to Alison’s excellent answer, you could try the other questions from the standards: what, when, who, where, and how. Especially if you do it in the context of customers, collaboration, and business outcomes. These tend to be more thoughtful questions and can lead to more specific and valuable answers from your manager. Instead of asking “Why?” you could try something like:
    “Who is the customer of this project?”/”Who is depending on my work?”
    “What went into the beginning stages of this project?”
    “When will the final outcomes of this project be available?”
    “Where will this project lead the team/department/business?”

    Reply
    1. Lynn P

      I like this — just asking “Why” feels lazy to me. What do you already know about the assignment? Are you asking “Why” before giving some thought to the answer to that question? How about organizing your “why” questions in response to a number of assignments — and see what you learn. “Why” is very important – but the work to answer this is question is a shared responsibility.

      Reply
    2. Dr. Pepper

      Think of your questions as guiding the conversation where you want it to go, and what you will do with the information that you’re requesting. That will help you shape better questions that are less likely to be perceived as passive aggressive attacks or insubordination. It sucks, though, as a “why” person. I’m asking why because I quite literally want to know, not as a lead-in to selling my own way better idea or as a way of saying I think you’re stupid, yet that’s how it often comes across. “Why” is often used as a challenge in our society, and unfortunately this is how many people take it.

      Reply
  12. mark132

    Sometimes it can depend on how often it’s being asked as well. If someone asks why at the majority of my statements etc, I’m going to get frustrated. It comes off as untrusting and challenging and annoying.

    Reply
  13. Ruth (UK)

    I like Alison’s answer for taking the context of the ‘why’ question etc into account. I’ve personally witnessed both sides of this – the person who questions everything and is always seeming to be saying ‘why? why?’ even when it shouldn’t matter / they should work it out themselves / whatever, but also I’ve seen the manager (or other authority figure) who responds poorly to any level of questioning as people try to gain understanding of what they’re being asked to do and why. (and also some in between, where a person is asking perhaps a bit too often / too much, but mostly within reason, and so on)

    Reply
    1. Queen of the File

      Agreed–there are lots of reasons that this could be an issue. I think pausing for a moment to ask yourself “what do I hope to gain from asking this question” and “do I really need this information” could be helpful. This would help make sure you’re not in the category of questioners who constantly ask ‘why’ out of idle curiosity or because it’s easier than spending a moment trying to work out answers for yourself.

      Reply
  14. AnonGoodNurse

    How I sympathize! Allison’s advice is very good. It took me years to pick up on the fact that I was annoying my bosses. I tried dialing back my questions and re-phrasing. It helped, but I was often on my boss’ grouchy side. She was particular about having her authority questioned. (Then there were the times I didn’t question it, only to be met with “you, of all people, should have questioned this.” Sigh.)

    That said, if it aligns with OP’s interests and career path, maybe consider a career where asking “why” is part of the job. I went to work for my industry’s regulator as an auditor. I spend my whole day asking “why” …. and also because that is what we do, our managers/supervisors are not as threatened when we ask those questions of them. It’s in our nature and its why they hired us. They understand and don’t take it as an adversarial question.

    Reply
  15. glitter writer

    I learned several jobs ago that the best way to ask “why” is to form it hard about context.

    So not, “why do you want me to make a document that convoluted and pointless,” but, “sure, happy to help with that project! What’s our end goal?”

    But lord, did I have a whole bunch of jobs who NEEDED someone asking “why.” Managed to streamline and fix a whole bunch of terrible little processes over the years.

    Reply
    1. Seriously?

      Yes! I think enthusiastic agreement to the task before the question will make it seem less like a challenge. “Of course I will make that document for you. Is there a particular reason we are using yellow font on white paper?”

      Reply
    2. NotAnotherManager!

      Same. My boss jokes that about 50% of my job is telling people, “You’re doing this process totally wrong, let me fix it.” but it a much nicer, more collaborative manner. “What’s our end goal?” is the perfect question for that! (In my head, it sounds more like, “Oh, my god, WHY would you do that?!?!?”)

      Reply
  16. Greg NY

    There are two types of “why” questions. There are those that are a genuine question, meant to figure out more information on something, and there are those that are a complaint in disguise.

    You have to know your workplace and your manager. But you have a bad manager if they bristle at the genuine questions. To be clear, even genuine questions need to be asked at an opportune time, it’s very possible that a big part of the problem is the time necessary to answer the questions and the manager is very busy at that particular point in time. But genuine questions SHOULD be asked. The job of a manager (and I have used that word exclusively to describe someone one reports to, I do NOT feel that anyone should be a “boss” and actually boss people around in a workplace) is to facilitate the work product of the entire team. They need to do what’s best for the team, and that includes being aware that others on their team may have ideas on how to do something better than the way they as the manager is currently advocating. A manager or an organization that doesn’t welcome those types of questions is in all likelihood going to be a pain to work for.

    To make it transparent to your manager, you should be more upfront with your questioning style. If you are going to ask why, follow it up immediately after the question with a desire to change something.

    Example:

    Manager: I’d like you to do this the way I asked you to.

    You: Why? I feel my way is better. By doing it my way, it will be more effective than if it was done your way because of .

    The key here is to provide concrete information about why a change is a good idea. The common goal is to produce the best work product, and if your way is better, a good manager will see that.

    If the “why?” question is a complaint in disguise, it’s better to just be upfront there as well.

    Example:

    You: I really don’t think your way of doing this is very good. It is negatively affecting the process by . I think it should be changed and done my way instead.

    In either case, part of the job as the manager is to make the call. The manager is the one that has to sink or swim with their decision, and if your manager consistently disregards your input, it’s a sign that your relationship is a bad fit and you might want to look into going elsewhere.

    I’ll add one final thing: “bosses” are the ones concerned with authority. A true manager will not feel you are undermining their authority provided that you do something their way once you gave your input.

    Reply
    1. Greg NY

      I just realized that part of what I wrote got cut out when I cut and pasted it from Word, where I was composing it. In both examples of what “you” should say, it should include “X and Y reasons”.

      Reply
    2. Hey Karma, Over here.

      I’ve had this experience, too. And that’s why my manager is great. We have multi page procedures for everything. Follow these start to finish. If I read through a new one and determine that the steps don’t flow with my order of doing things my manager is open to me saying, “I’d like to start at page 4, go to 10 and swing back to page 2.” Three outcomes: One: knock yourself out, just don’t miss a step. Two: You know what, let’s rewrite the procedure and three: Nope, if you do X first, the option to do the stuff on page two goes away.
      And that’s why I stay here.

      Reply
    3. Observer

      Presenting it this way is quite likely to end poorly for the OP, especially if they are new in the job. Telling your boss that they are wrong is rarely a good idea.

      Reply
      1. Seriously?

        Yeah. If your manager tells you to do it a certain way, saying “Why? My way is better.” is in fact a challenge to their authority. It is better to take a very soft approach to that type of thing unless you have a very good relationship already and know that they will take it well.

        Manager: I’d like you to do this the way I asked you to.
        You: I can do that. Do you mind explaining why X is better than Y in this instance? I would have thought Y would be more efficient.

        Acknowledge their authority to determine how it is done and agree. Then ask for clarification in a way that assumes that they are correct. Or if there is a concrete reason you can’t do it the way asked, explain that.

        Reply
      2. NotAnotherManager!

        I generally try to avoid “my way is better than your way” phrasing, regardless of audience. “Have we considered…” and “What about [better way]” phrasing coupled with the benefit (cost savings, reduction of risk, etc.) tends to work better than directly questioning whether someone’s way is the right one. Goes back to the idea of trying to lead with yes (or yes, and) rather than no.

        Reply
    4. Lucille2

      I think this is a great way to illustrate the “why” question. I would add that if you are presenting a better way to produce the work product, keep an open mind about what it means to implement your idea. A manager may have information you’re not privy to, and a good manager will make that clear. Perhaps that information is that changes are on the horizon and it’s best to wait it out at this point. You are not always entitled to know details about those changes, and that may be reasonable. It’s time to trust your manager on this one.

      Or, your great idea may be a bit naive which turns into a learning opportunity. I’ve received a lot of great ideas from direct reports pointing out the obvious. Why don’t we just do X instead of Y. It’s so much simpler! Often this is because the asker has not really thought out the pitfalls of X and why we would never do it that way. The why question sparks a good discussion and learning opportunity. But as their manager, I would never bristle at the question being asked unless I feel they are pointing out the obvious too often and not really learning anything from the discussions.

      3rd, manager may just shut down your idea because it’s in their authority to do so. I’ve worked under the manager who’s response to everyone’s “why” or “can we try this instead” questions is always “because this is how we do things.” In those cases, you now know what kind of manager you report to, but it’s still important to know when it’s time to back down. Take a look at your environment in those cases. Are you the only one asking “why?” Why do you think that is? It might indicate your culture is not a safe place to question the status quo.

      Reply
      1. Guacamole Bob

        The older I get, the warier I am of any question that uses the word “just”. It’s virtually never as simple as the questioner thinks.

        Reply
    5. smoke tree

      I think there are two potential pitfalls of “why” questions: the ones that are actually just complaints in disguise, as you say, and the ones that are just asked reflexively without much consideration for whether it’s really worth the manager’s time to explain. I think the first one is going to be immediately annoying to any manager, but the second will also wear on them over time. And another possibility is that the LW isn’t doing either of these, but enough of her coworkers are that she needs to make sure it’s obvious to the boss that her questions are worth asking.

      Reply
  17. Dust Bunny

    I agree with all of the above advice about reevaluating your tone, wording, timing, and frequency, and I would also encourage you to consider if you’re seeking the answer yourself enough before you ask. How much of this could you discern without asking? If you’re actively seeking patterns of connectivity, surely at some point you’ll start to find them and then use them to extrapolate, which should reduce the need to ask.

    If your first reaction is to just ask why, you’ve offloaded the work of providing the answer to your manager/whomever you’ve asked. You might get better results if you do what you’ve been asked to do first, think about how it resembles other tasks, and approach your manager for an explanation later when a) she’s less busy and b) you’ve put effort into it already and are in a position to demonstrate that you’ve given it some thought.

    Reply
    1. Dust Bunny

      I do what are basically research interviews as a normal part of my job (academic library). If somebody calls me seeking information on Institution X and I respond with “Why?”, neither of us is going to get much out of this. It’s a whole lot more productive if I ask them what the underlying project is and more about the outcome they want. It might turn out that I need to look in other collections, as well, or somewhere else entirely. Phrasing is pretty much everything.

      Reply
  18. boo bot

    1. I think the “how” of asking why is really important, not only because “Why?” by itself can seem like a challenge to the decision, but because from the manager’s side, it can be hard to intuit what part of your reasoning someone else isn’t following, or what information they don’t have.

    “Why should I do X?” is a really broad question that probably has a really broad answer, and it also can suggest that you lack some fundamental understanding about the job, depending on what X is.

    “I had the sense that X and Y were both potential solutions to the problem, can you tell me why we decided to go with X?” makes it clearer what you are asking (and that you understand what X is).

    2. I have known and worked around some people who react to any and all questions as either insubordination or admissions of fatal weakness (including, like, “Hi, I just started two days ago. Can someone tell me where the staplers are?”) This is terrible.

    Reply
    1. Dust Bunny

      This, exactly. “Why” is far too broad, and not providing a comparative example suggests that you’ve jumped the gun with the question.

      Reply
  19. Artemesia

    I control anxiety with my big brain i.e. knowing and understanding feel like being in control and it is important to me to understand how my piece of the operation fits and what our goals our etc etc. But ‘why’ reads as ‘justify your authority to me’ to lots of managers, so a person like I am needs to manage that interaction so as not to provoke this response. I found that actually explaining that to the boss worked usually (not with one guy, but he was monstrous to work with across the board and I developed other skills to manage up with him). Early on I would explain when a complex project was assigned that it helped me be efficient if I understood how everything fit together — what are we trying to accomplish and why are we doing it this way and so that was why I was asking big picture questions. This helped frame my curiosity so that it was about me understanding and not challenging them. It mostly worked.

    Reply
    1. Rusty Shackelford

      Yes, but the comments above yours demonstrate that some types of “why” questions are an attempt to do things better.

      Reply
    2. Guacamole Bob

      My job has many situations where someone will ask a question like “what would happen to teapot sales if we added coffeepots to our lineup at the new store?” and my job is to come up with a projection. There’s often an approximate version of the answer that will take me an hour and a version that will take me a week but be much more thorough and detailed and accurate. I need to be able to engage with the person asking, either directly or through my boss, to know what type of response to give to a particular question. Who’s likely to see the answer? Is this off the cuff after a brainstorming session or part of a budgeting or business planning process? Do you also need the impact on tea sales, or just teapots?

      The initial request is reasonable and I’ll do it whatever the answers are, but when I’m more informed it’s better for my end product, my work flow, etc.

      Reply
      1. Kelly L.

        Yeah, I have to “manage up” one of my bosses like this. He’ll say, “just offhand, about how many people are in X group?”, and since he said “just offhand,” I used to just estimate for him. “Oh, I think about 20.” Next thing he’s putting 20 in some kind of official paperwork as a real figure. So now I’ve trained myself to ask what it’s for, because “just offhand” is sometimes a lie.

        Reply
  20. Liet-Kinda (nee Snark)

    I posted this a while ago:

    I totally agree that asking for more information, or clarifying how changes will ramify, is the prerogative of anybody implementing a new directive. Nobody should scoff at that, or give it any sideye.

    But I feel like I’ve also seen it happen where questions are less “Can you give me more information to do my job better and make this work” and more “I think you’ve probably failed to think this all the way through, so let me probe your decisionmaking process for weaknesses.” And that’s the kind of questioning that can burn capital at an alarming rate, so one needs to really interrogate whether one is doing it because they a) truly believe their boss might have missed something important or didn’t consider some potential wrinkle or b) whether one doing it because they’re a smug know-it-all who thinks they’re entitled to a full justification of the entire decisionmaking process before they’ll move ahead.

    And if it’s b) then I think that’s a temptation to be avoided, because at some point, second-guessing everything your boss decides is a great way to annoy the hell out of them.

    And another thought:

    I generally take the approach, myself, of taking serious concerns or questions to email after the fact. Even if it’s a good question about an aspect they truly didn’t think through, I don’t want to put my boss on the spot by grilling them in person, with an audience of their subordinates. And it lets me articulate my question in a more thoughtful and considered manner than tossing things off verbally. It generally ends up feeling more productive and less like a pretentious know it all demanding that the boss justify and defend their decisions.

    Reply
    1. Tardigrade

      I really like the idea of asking questions in an email after the fact. This would also give OP time to start working on the task and troubleshoot the “why” on their own, as suggested above. “I’ve started doing this and am curious about how…” will probably be a lot better received.

      Reply
    2. AMPG

      I like the email after the fact approach, because it gives you some cover to approach it as, “Now that I’m thinking it over, I realize I may not have understood these points. Can you give me some insight about them?”

      Reply
      1. Liet-Kinda (nee Snark)

        I generally find that almost never am I satisfied with how I ask a question or raise an issue in the moment, and that I inevitably come off better asking about it after the fact.

        Reply
  21. VioletDaffodil

    You might be interested in looking into Gretchen Rubin’s four tendencies habit framework. It is an interesting way to think about how we approach tasks in our lives. Basically, she indicates that there are four types of behaviors that people display when deciding to work on a task/develop a habit; these are:

    1. Upholders
    2. Obligers
    3. Questioners
    4. Rebels

    Upholders are able to easily meet all expectations; so, in a work context, if a boss tells them to do something they get it done. Obligers are good at meeting tasks that are important to others, and have a tendency to sacrifice their own goals to support someone else. Rebels will only do what they feel inspired to do in the moment; anything else feels like a limitation that they must resist, even if it comes from themselves.

    Questioners are able to do any task, but it has to make sense to them first. They like to research, see the bigger picture, and understand a task or goal in a larger context. If it doesn’t make sense to them, they have a hard time doing it.

    It sounds to me like you fall into that last category (and I do too!), so in addition to Allison’s advice about changing the framing, some strategies shared for these Questioner type folks might help you too.

    Reply
    1. Not My Regular Username

      There are Questioners and there are Questioners, though. There are Questioners who lob a lot of “why” questions upfront, possibly like the OP. I’m probably a Questioner, but I do a fair bit of legwork on my own to see the bigger picture rather than creating extra labour for the person who’s requested something of me. If I can’t get those answers on my own, then I ask someone more specific and context-driven questions to avoid putting them on the defensive. The way I see it is that it’s largely my responsibility to make something make sense to me – it makes me seem a lot less oppositional than Questioners that place that responsibility primarily on the other party.

      Reply
      1. Lil Fidget

        Also even if OP is this way as a default, it sounds like she needs to adapt her approach / learn a new skill in order to work well with this manager. It can be helpful to have the self awareness but the next step is still action.

        Reply
  22. Riley

    I have definitely had bosses who were of the opinion that me asking anything about the big picture stuff was insubordinate and undermined their authority because it was their job to know, not mine. In one case, I had my job under a director who encouraged asking questions and generally believed that our team operated better if more people understood the principles behind why decisions were being made. That director left for another job and the new director just wanted me to do what she said and didn’t appreciate me asking questions beyond “I don’t understand what you mean”. So a lot can depend on the particular boss, their personality and expectations, and how your personalities and working styles function together.

    Another tip though: if there are other people in your organization who could answer your questions, ask them rather than asking your boss!

    Reply
  23. Dr. Pepper

    I am also a “why” person. I *need* to know why I’m doing a thing or I simply don’t care. I also know that it can come off as defensive or insolent when I ask “why”. So I try to rephrase the question to be about a specific thing, as per Alison’s example. It’s not always easy, especially because “why?” is such a short, sweet word and it’s tedious to formulate complete sentences that ask “why” while being properly respectful and deferential every time. As a manager, I LOVE explaining why I want a thing done or done a certain way (unless it’s a mundane thing, like dropping off something at someone’s desk because seriously?), and I probably give people more information than they want or care about. If you asked me why, I would tell you quite happily, and also probably at greater length than you wanted. But that’s me. I love knowing “why” and I love explaining “why”.

    Some people don’t like to be questioned at all. Period. They expect you to carry out orders like in the military. They say do the thing, you say “yes, ma’am/sir”, and you do the thing with no further comment. For these people, no way of wording the question will be acceptable, so be prepared for that and decide how much you want (or can afford) to push back. Personally, these types of people get a lot less effort from me, and my usual perfectionism and drive to do the thing to the best of my ability turns into “eh, good enough”. You want above and beyond? You tell me why I’m doing the thing. You just want to give me orders? It’ll get done, but it’ll be merely satisfactory.

    Reply
    1. Undine

      “it’s tedious to formulate complete sentences that ask “why” while being properly respectful and deferential every time”

      I would argue that if you find it tedious to phrase your questions, that explains it right there why people get frustrated with the frequency. Because in order to answer you, they have to dredge up the why from their memory or put it together from the angle you are asking, mentally reorganize it to be appropriate to your level, and then formulate the answer in understandable terms. That is more work for them than phrasing the question for you.

      I also wonder if you and the OP are timing this badly. If you are interrupting workflow, or pushing back when the boss assigns it to you, then you may be interrupting the boss’s workflow and stopping them from getting other things done. Like, if the boss wants you to get started on XYZ because it’s important, but they also need to get their ducks in a row for a big meeting they have on the topic in an hour (and maybe they want to be able to say, “oh, I’ve put Fergus on the project” in that meeting), then the timing is terrible. If you can batch your questions in a weekly meeting, or say, “I’d like to know more about the context, is there a time we can discuss that later?”, then at least they don’t dread asking you for something.

      And for some tasks, “good enough & not having to spend time on explanations” is a much better outcome for them than “perfect according to this person and a lot of explanations.”

      Reply
    2. Liet-Kinda (nee Snark)

      “I am also a “why” person. I *need* to know why I’m doing a thing or I simply don’t care.”

      I’m curious why you frame this as a need. I’m also this way, but I tend to think of it more as an area of improvement than either an immutable fact of my psyche or as a strength in how I work. It’s not really a hugely positive attribute.

      Reply
      1. Liet-Kinda (nee Snark)

        And, to expand: I find that a lot of the time I get into the whys and wherefores, if I think on it for a beat before I ask, I often arrive at one or both of two conclusions:

        a) The answer can be inferred from context sufficiently to satisfy my curiosity, and/or

        b) The answer is fundamentally banal, like “it’s a legal requirement” or “we need to document this in case we’re inspected” or “the effort required to get all the stakeholders together to agree on a different workflow exceeds the notional benefit of changing it” or whatever.

        Very often, you don’t actually need to know why to do it, and if you did know why it would not clarify much, and as long as you’re doing it anyway I generally take the attitude that it should be done as well as possible. Maybe I work with too many serious persons whose clothing blends into woodland areas, but there’s a certain value to being able to just go and do what you’re asked, and have others go and do what you ask of them, without everyone engaging in a lot of tiresome emotional labor to make the case that we should go and do the Thing with a spring in our step.

        Reply
        1. Dr. Pepper

          I suppose my context was unclear. Very often yes, the “why” is obvious from the context and a moment spent thinking about it, and even more often it’s some legal or bureaucratic requirement that you have to follow because you have to. This is not what I have issue with. I can follow rules and unless the rule is egregiously stupid I can follow them quite happily. Most of the time I can figure out the why on my own and don’t need to ask about it. For what I do though, why I’m doing it matters very much. It doesn’t need to an emotional burden, and I don’t require long explanations, but knowing the motivation behind a request helps me determine what to do if the request cannot be fulfilled exactly as directed. Since this is very common and often not something my boss wants to be bothered about, I need explanations. If I don’t get them, it’s difficult to do my job. It becomes difficult to care about doing a good job if I’m not given the tools to do it properly.

          Reply
      2. Dr. Pepper

        It’s something I have discovered about myself over a long period of time. I don’t know if I’d say it’s positive or negative, it just is. If I don’t know “why” and can’t figure it out (which I often can), I have a very hard time making myself care about whatever the task is. The flip side is that if I know why I’m doing something, I care very much about doing it well and will put in effort to do a good job. So it’s both a strength and a weakness, like everything else. I’ve heard it described as “the other side of the hand”, as in your strengths are also your weaknesses and vice versa.

        Reply
        1. Dust Bunny

          Why do you have to care? It’s your job. Just do it because it’s your job. A HUGE percentage of my job is tedious and repetitive and it’s likely the results will never see the light of day again, but I do it well because it’s my job.

          Reply
          1. Dr. Pepper

            Because it’s essential. Good outcomes of my work hinge on my full understanding of the project. If I’m doing tedious and repetitive things, or things that just need to be done, no I don’t need explanations. I’ll just do it. Unless something strikes me as very inefficient or stupid with no real reason for doing it a certain way. Then I’ll ask questions, diplomatically phrased, to determine if anything is open to reevaluation and change.

            Reply
    3. Amtelope

      I think tasks vary widely in how much context is needed to do them. If you’re building a prototype for a client, you need to know what it will be used for. If you’re proofreading a spreadsheet, you generally don’t need to know what the spreadsheet will be used for. “Why are we building this?”/”So that the client can choose a spout for their chocolate teapots.”/”OK, great, we will make sure we provide a range of spout types, but not bother including different flavors” is a useful conversation. “Why do I have to proofread this?”/”Because we can’t have any errors.”/”Yes, but what is it for?”/”It’s for the XYZ event, and I just need you to proofread it” probably isn’t.

      Sometimes it’s not possible to do great work if you’re missing truly necessary context. But I don’t think it’s ever acceptable to deliberately do less than your best work because you don’t know why a task needs to be done.

      Reply
      1. Dr. Pepper

        If I’m doing mundane tasks by all means just give me instructions and I’ll carry them out to reasonably high standards. However, my work is very much impacted by why I’m doing it, which is probably why I went into my field. In what I do I often need to make daily adjustments and decisions where the why is critical to getting good results. My job is often to make seemingly low-level calls on things that over time have a big impact on the outcome of the project. If I don’t know “why” I can’t make those decisions effectively and the end result is compromised. I’ve worked for supervisors who don’t understand that, and it was beyond frustrating. One would shut down all my attempts to understand why they wanted what they wanted, then would get upset when I gave them quite literally what they asked for and nothing more.

        Reply
    4. TootsNYC

      “why?” is such a short, sweet word and it’s tedious to formulate complete sentences that ask “why” while being properly respectful and deferential every time.

      This actually pissed me off a little.

      “why” is WAY too open ended. Someone above you mentioned “putting the burden on the answerer.” That’s what this does.

      You ask me “why,” and I have to figure out which PART of “why” you want to know. The part about what we’re trying to accomplish? The part about which executive weighed in? The part about which laws are applicable? The part about which computer program is balky?

      That’s a lot of mental work that you’re dumping on me!

      You need to do the work of defining your question before you ask.

      Reply
      1. Dust Bunny

        Amen. “Why” is useless and lazy. It says you haven’t taken the time to consider and refine the question and are going to dump the whole thing and its endless possible answers in somebody else’s lap.

        Reply
      2. Dr. Pepper

        I don’t recall saying that’s what I actually do in real life, it’s just what I’m thinking. I wish I could just ask “why?” and then be given a well reasoned explanation, but that’s not how it works. Just because I wish I could do something a certain way doesn’t mean that’s how I do it. My questions are always practically formulated and not open ended in the way (I think) you mean. What I find tedious is having to make sure I’m wording everything in a way that doesn’t ruffle feathers. Some people hate being questioned and very often I have to question them. It’s the nature of my work, and it bothers me that I have to make sure I’m being properly deferential while getting critical information to do my job well.

        Reply
    5. boo bot

      “As a manager, I LOVE explaining why I want a thing done or done a certain way”

      I know, right? Not a manager, but I, too, pretty much have to know exactly why I’m doing what I’m doing in order to do it effectively, and I get SO excited on the rare occasions when someone asks. Ask me why and I will tell you ALL THE REASONS.

      Reply
  24. Bea

    This can be a personality thing as well. I always explained the “why” when I’m asking for something, I then found out some people hate it. “I don’t need to know the why.” and another even stated it was rude to give that extra info. So I’ve changed how I speak with those people. Perhaps your boss sees your questioning as demanding and not respectful that she, the boss, just told you to do something. Kind of like when a parent assumes a child is talking back.

    Thankfully I leave any boss who is rigid and difficult like that as quickly as possible. Once I know the “why”, I am more aware of the entire scope of a responsibility. Heck, I learned entire operations simply by all my “hey what is this exactly?” “What does this even do?”

    Reply
  25. Minty

    I’ve been on the other side of this- getting asked “why” too much, with a definite subtext of “I don’t agree with this”. The advice to expand past “why” is really good- there were some parts that merited examination and tweaking but they got lost in all the other “why”s.

    OP, I’d also take a look back at the answers you’ve been getting in the past. If there’s a lot of “because that’s the way it is” maybe step back? Especially in some jobs (hi fellow government workers!) there’s a lot of “because the owner of this process wants it done like this”.

    And the times I’ve wanted my own “why” answered, I’ve also found some success in gently reaching out to people connected to it/ who used to do it for background, or a sense of how set in stone things are.

    Reply
  26. sheworkshardforthemoney

    Why is a very open-ended question. A co-worker once asked why? in response to a simple directive and our manager responded with “Because the sky is blue.” If your question advances what the manager said, then it’s good. Maybe ask a co-worker or someone with more institutional knowledge why first. Otherwise why questions can be time wasters.

    Reply
    1. Liet-Kinda (nee Snark)

      Yeah. Ask focused questions. “Why” can be irritating from a four year old; it doesn’t improve with multiples of years.

      Reply
  27. Kms1025

    I can tell you that I’ve never felt my authority being challenged, at least not outright. But I have been driven crazy by “why” questions. Those usually come across to me as someone either covertly registering their displeasure about an assignment or just trying to use up their daily allotment of words. Truly well thought out questions with a desire for knowledge seem to be rarely posed as simple “whys”.

    Reply
    1. Let's Talk About Splett

      Yeah, I would need to know context as well to assume this is about the boss not wanting their authority questioned.

      Reply
    1. Let's Talk About Splett

      I’ve mentioned this here before, but my boss likes to ask, “What’s the question behind the question?”

      Reply
  28. DEJ

    Oh my gosh this is me and my boss exactly. No additional advise but sometimes it’s so hard. We’ve worked together for over 11 years and still have moments where we struggle with this.

    Reply
  29. CupcakeCounter

    Why questions are good but it absolutely needs to be more than just “Why?”. Alison’s example is a good one – it softens the question and explains that you are asking for learning reasons not questioning authority reasons. Timing is also important. If possible send you manager an email with your questions and why you are asking so they can answer at a convenient time.
    I would bring this up at your next 1:1 (if you have them) and explain to your boss that you realize you are asking a lot of these questions and let her know that it might not be coming across as you intended it. Bring an example of when knowing the “why” of something resulted in a better outcome for your project. I.e. how you were able to tailor the report for a certain group since you knew in advance that operations people were reading it vs finance people or you knew exactly who to go to with questions because you had a bigger picture view of the whole project vs just your portion. Then ask her the best way to get this extra information – private chat vs staff meeting, email, etc…

    Reply
    1. Not a Blossom

      I like this. And related, if you can’t think of an example when asking why resulted in a better outcome, it’s a sign that you need to re-evaluate when and how often you’re asking.

      Reply
  30. Sara without an H

    Hi, OP: There’s a lot of good advice upstream about timing, tone, and context. To these I would add that you need to be sensitive to indications of urgency. If your manager is running about with her hair on fire, saying “Quick! Quick! I need all of last year’s sales data on the Chromium Cocktail Shaker account!” that is NOT a good time to ask her why she wants it. Just get it for her and stand out of the way.

    Do you have one on one meetings with your manager? Maybe you could save up some of your requests for context and work it into your meeting. “Now that we’ve launched the new product line, I wonder if you could give me some background on why the marketing campaign relied so heavily on late night television ads? I really want to do a good job on the next roll-out, and it would help to understand our thinking on this.”

    My other suggestion is that you look for a mentor other than your manager to answer these questions. If what you’re interested is the context of how your work fits in with the larger organization, there may be a senior person in your work group who can fill you in on this. And we Olds love it when young people ask us for advice.

    Reply
  31. Let's Talk About Splett

    Keep in mind that your manager may not be in a position to tell you why or tell you at this time, either, because it needs to be on the down-low right now, and it’s really a bad look to press for a “Why do you want this?” when you can’t or should not be privy to the answer.

    Two examples from my work life:

    I was asked to create a spreadsheet with outstanding balances owed to vendors. The Why is that we were up for sale, which wasn’t ready to be announced.

    My boss asks me to send him a list of all client meetings my coworker had scheduled . . . because my boss was planning to terminate & coworker & wanted his ducks in a row. (I’m an admin)

    Reply
    1. Bea

      My bosses always told me why when I was an EA. But I never asked them, they volunteered the information and I was in a weird position where they always viewed me as the a absolute inner circle. It’s way different in larger work setup.

      Reply
  32. gecko

    When you say, “why,” or “how come,” or some equally bare variation in phrasing, I think it’s not actually clear to your boss why it’s relevant for you to ask. So she has to figure out why you’re asking, and something either internally (worry about her authority) or externally (a vibe you’re giving off) is signalling that you’re asking as a challenge.

    Giving additional context, ie, “why did they delay the newsletter? I’m asking so I can think if there’s anything I need to tweak next time,” means that there isn’t a need to try and detect why you’re asking, so there’s less risk there. Think of it like you’re trying to be less vague and help the conversation along.

    And, to be clear, if you are kind of trying to argue a little bit maybe when you ask her “why” questions, cut it out, because it’s pretty detectable.

    Reply
  33. Dragoning

    My boss and I have had a version of this conversation, actually—I’m new-ish to the company, but also hungry and semi-ambitious and I feel the need to know things and how they work and whyt they matter and how they fit into the larger company.

    So my boss put it into my development plan career goals and makes appointments for me to job shadow other people, even if it’s unlikely I will ever do their job.

    OP, you might want to bring this up in a general way instead of as individual questions–address the root of the problem.

    Reply
    1. TootsNYC

      A person can also say, “Sometime when you’ve got a minute, I’d love to here more about how they react to the newsletter, and what sort of stuff gets sent back, and what you think their standards and goals are.”

      Reply
  34. Anononon

    From the other side of it, I’m very much not a “why” person. I’m pretty intuitive so I tend to pick up the why and the big picture in time.

    This can be a bad thing because I can get impatient when training a why person. It does help, though, when the questions aren’t just why but are more in-depth.

    Reply
  35. Baby Fishmouth

    My manager is usually great about explaining new policies/processes so I rarely have an issue with her, but man does the finance department hate me.

    I constantly have to ask them why because they decide to institute new policies, or begin enforcing old ones, or just make new decisions. I’ll get a claim returned because they’ve decided that Amazon receipts don’t count as receipts, or that driving to a nearby city is no longer allowed and everyone must take the train or fly instead, or that flights can’t be reimbursed without hard copy boarding passes. I have to ask them Why all the time, because nothing will ever go through unless I point out how convoluted and inconsistent their policies are!

    Reply
  36. CastIrony

    *cries because I can’t read a room (or people) that well due to social anxiety and ineptitude*
    I too, like to know what is going on and why. I find that communicating with whoever you report to, while important and hard to do, is better than doing things and not communicating at all. However, asking specific questions and why you are asking does help. It’s also good to apologize or say, “Excuse me, (question)?”

    The following example is in the context in which I work in a cafeteria, and this has happened to me.

    Example: (Sees on a food label that a raspberry cake has dairy in it, but a customer asks if it has soy in it because they’re allergic, and I don’t know because it isn’t on the label.)

    Me: (asks the cook I report to) “Excuse me, but does the raspberry cake have soy in it?”
    Cook: (frustrated/annoyed) “Every allergen it contains should be on the label.”
    Me: “I’m sorry; I just want to make extra sure.”

    tl;dr: I find that it is better to communicate and ask specific questions with an “excuse me” and/or an apology. That being said, I agree that it is best to ask your manager (or whoever you report to) to ask how to communicate with them if you are brave enough to (I am not).

    Reply
    1. Baby Fishmouth

      I don’t see anything wrong with questions like that as long as you are learning from the answer. In your example, you’ve now learned that all allergens are on the label. You shouldn’t have to ask the cook ever again – if you asked EVERY time someone asked you, that would probably start to be a problem.

      Also, don’t apologize for asking questions – questions are good! Prefacing a question with an ‘excuse me’ or a ‘sorry to bother you’ is very different than ‘sorry to ask this question’

      Reply
    2. Sam.

      In situations where I’m asking about something I know I should know, I will preface the question with that. I’m fairly new at my job, so I’m asking things like, “I’m pretty sure I know this, but just to be completely sure – we need X form for Y process, right?” (As someone who traditionally fields lots of questions at work, “Please confirm I understand this correctly” were by far my preferred kind!)

      Reply
  37. Observer

    OP, I sympathize with you. My job requires a lot of “why” to do effectively. And I also like to understand the bog picture and how what I do fits in even when it’s not strictly necessary. I also enjoy sharing that kind of background (sometimes, too much.)

    You’ve gotten a lot of good advice. But you may also just need to dial back your “need to know in order to do the task.” There are times when your boss is going to decide that giving you that information is just too much work for the payoff to your ability to do the required task. Especially when the reasons are convoluted, inflexible (eg that’s what the government requires), or apparently unreasonable this is likely to happen.

    For example, if your boss asks you to run the government mandated paper clips utilization report, and you ask “why do we need this report?” your boss is probably thinking “I do NOT have the time to get into the political insanity and institutional incompetence that lead to this report, thank you very much!”

    Also, think about how you respond to the answers you do get. Do you follow up with MORE whys? Or do you accept the answers you get? That can make a huge difference in how this is received.

    Reply
    1. Dr. Pepper

      Mine does too. Often to a greater extent than many people who do not do my job think it should.

      I think that the OP would benefit from taking some time for thought on this. Perhaps some of their questions would be answered by taking a minute to think about it. Or let them realize that maybe the “why” isn’t as necessary in certain contexts. And when it is necessary, think about how you’re asking the questions and what sort of follow up questions would be useful. Think about the questions as guiding the conversation where you want it to go instead of being interrogating.

      Reply
  38. McWhadden

    I think this can be frustrating for some managers because they just don’t have a good answer. As they say sh!t runs downhill. And a lot of organizations (especially government but many large organizations) just don’t give out information before issuing what amount to orders. So, middle managers may just not have enough information to answer the why.

    That is probably not a good way to do business (outside of security clearance reasons and such) but it’s the way a lot of places with a complex bureaucracy work.

    Or some bosses are just jerks.

    Reply
  39. That Would be a Good Band Name

    I haven’t read all the comments, so forgive me if this is a repeat of someone else. I had to learn to hold off on my “why”s. I am a person who needs the big picture to understand my task. It’s hard to explain, but my brain needs the whole picture. If I try to just do the steps I’m told I’ll forever need a checklist and not really “get” what I’m doing. But if I know that I do X because X makes Y happen and that allows Z to occur then it just makes more sense to me and I’ll really absorb the process and be able to do it better.

    I try to wait until 1x1s if it’s a “why” that I don’t actually need to know to finish the task. It’s a great time to say something like, “So on the project we just finished, could you help me understand how that relates to (whatever makes sense here). I’d really like to understand that process better”. I’ve found it really frames it in a way that even the most defensive manager doesn’t think you are just being difficult. It’s hard to ask why when the task is being assigned without coming across that you are pushing back on doing it.

    Reply
    1. Dust Bunny

      This is why consideration and phrasing are important. The goal should be to balance the information you need with the expediency your boss needs.

      If my boss asks me to, say, move all the books from location X to location Y, I’ll ask, once, what the end goal is here, and part of that is so I can avoid asking him any more questions if we run into an obstacle–I’ll have enough information to solve the problem on my own.

      However, if the reason is, “We’re moving Other Collection of Books” into location X, I’ll let it go, because I more than likely do not need to know immediately why we’re doing that. If it becomes apparent later that this is going to be a big project with lots of book-shifting, I’ll ask a follow-up.

      Reply
  40. JellyBean

    At my previous job, when I was new, I sometimes asked my boss questions about work she was giving me because I wanted to understand what I was doing and the context better (and sometimes her instructions were different than things teammates had said, so I was confused). Her response was to ignore the question and repeat the last thing she said, so I quickly stopped asking questions. There were a few times where she gave me instructions to do something and I noticed that she may have made a mistake or missed something, but I wasn’t comfortable asking questions so I just did as she asked and then would have to deal with it being wrong.

    I definitely appreciate working with people who don’t mind some questions!

    Reply
  41. Not All

    And for the love of all you find holy, PLEASE look at how many questions your coworkers ask to see just how many questions you are asking in comparison. If your manager has reached the point of having to say something to you, I would bet very good money that you are way waaaaaaaaaaaaay outside the norms.

    I felt my teeth grinding just reading your question with flashbacks to That Coworker (who seems to exist in every office over a certain size) who just will not stop asking questions during meetings. The one that as soon as we see their name on the attendee list, we immediately mentally double the amount of time the meeting will take. The one that (good) facilitators/trainers/managers inevitably end up cutting off at some point to say “why don’t we pick this up during break one-on-one” or “let’s see if your questions get answered later on”. PLEASE stop being that coworker. For your own sake as well as everyone else’s (after awhile, That Coworker is not a popular person no matter how nice they are otherwise).

    Every time you start to ask why, stop for 30 seconds and really really think about do you NEED to know the answer? Is there a way you can find the answer yourself? Can you guess the answer and then watch how things play out to see if you were right as a way to actually learn yourself rather than relying on your manager/coworkers to figure it out for you?

    Reply
  42. Thus Spake Zaso

    Pro tips from clinical psychology:
    1. “How come?” tends to provoke less defensiveness than “Why?”
    2. Leading a sentence with “why” is most likely to provoke defensiveness.
    3. Explaining the “why” behind your own question can be helpful in defusing potential defensiveness, e.g., “I’m trying to figure out…” or “I want to understand this better…”

    Reply
    1. Brownie

      #3 has been a fabulous thing for me. My relationship with my boss has greatly improved once I started rephrasing like that since he has a fundamental personal need/drive to make people understand what his thought process was. He no longer acts like I’m questioning him or undermining his authority because that phrasing makes it about me instead of coming across as being an accusation towards him.

      Reply
  43. CM

    Before you ask “why,” it’s also useful to think about your purpose — in other words, WHY are you asking?

    1. Asking out of curiosity
    Save up these questions for a time, place, and person who has the patience to answer.

    2. Asking because you think additional context will generally help you in your job
    3. Asking for clarification/details that you need to perform a task
    For both of these, say why you’re asking, and ask a specific question. For example, “Could you tell me who receives these reports and what they use them for? That will help me understand what to write in them.”

    4. Asking to raise a concern / question a decision
    Think about whether it’s really your place to question this. Are you being helpful, or getting in the way? Is your question actually going to change things? If you think you’re actually being helpful, consider making a statement rather than asking a question, like: “I’m concerned that this plan makes it harder to serve customers with complaints.”

    Reply
  44. Amtelope

    A bare “Why?” is easy to read as questioning the value of a task, even if that’s not how it meant. I think it’s often more palatable to ask a more specific question with a built-in explanation of why you need to know. “What will this be used for? That will help us ensure it fits the user’s needs.” “This isn’t how we typically paint teapots; was this a specific client request or is this a change that should be incorporated into the rest of our teapots from now on?” “Can you explain to me how you decided to use mango flavoring for the teapot, so that I can learn more about how we choose the right teapot flavor?” Etc.

    Reply
  45. LGC

    OK, here’s my take:

    1) Yeah, it can be primarily a question of tone, if we’re taking the title of this letter literally. Definitely expand as possible – and also choose your battles! If you’re asking for justification a lot, maybe go with the flow more often on lower stakes issues.

    2) But also, I feel like some managers just don’t like having to justify themselves. I think they’re bad – because if you’re asking your team to do things and you can’t explain why, then you shouldn’t be asking your team to do those things! (And further, I believe that employees SHOULD ask for clarification and explanation on some things.)

    2a) this is also a scale. There are times where I’m tired of litigating something, and while I understand my team’s concerns, I’ve probably already considered it and made what I think is the best decision. Basically I think that employees are entitled to ask for clarification on occasion and managers need to be okay with that, but it can’t be on the majority of issues, and you can only really debate rarely.

    I’m not sure where your manager falls on the scale, but I can go off my own experience.

    Also, I would totally not be surprised if my boss sent me this letter and asked me if I saw myself in this!

    Reply
    1. Dr. Pepper

      I didn’t take the letter literally and now I’m wondering if I should have. Meaning, I thought that the OP was asking fully formulated questions, like, “Why are we doing project X instead of project Y when Y has an earlier deadline?” type questions instead of literally asking “Why?” Not that the first question is the best, but at least it has a little context. Perhaps I was in error there.

      Reply
  46. Rachael

    I used to work with someone who asked “why” and said “I don’t understand” frequently during conversations. She had no idea how annoying it was to be trying to train her or tell her something and have to stop my train of thought to explain the background of something or try to say something in a different way. OP, maybe it would help if you started keeping track of when you asked your “why”. Is it in the middle of an explanation and then the speaker has to backtrack to their original thought to finish what they were saying? My coworker was very understanding when I told her that sometimes the derailment of what is being said to “explain why” throws everyone off track and it takes a minutes to get back to the actual task at hand. She started waiting until I was finished talking or after a task was completed to get the information she was seeking and I, admittedly someone who loses train of thoughts easily, was able to make sure that she understood why something was done in order to process it the way she needed.

    Reply
    1. Grumpy

      I was trying to find a way to eloquently post what you just did. Nicely done. Also, the worst case of the “whys” i’ve encountered was from someone in their mid-fifties, but the generational context is helpful.

      Reply
    2. TootsNYC

      also, if you don’t ask “why” right away, in 2 minutes, you may hear the answer from your trainer! People can’t speak as fast as a brain can move.

      Reply
      1. LizB

        Very very true. I doubt the OP is butting in with “WHY?!” halfway through the boss’s sentence, but this is something I very intentionally train into the kids I teach: let me give you ALL the instructions before you ask me questions. 95% of the time, the question you just blurted out will be answered by a later part of the instructions.

        Reply
  47. Critical

    Questions can be as burdensome as ideas/suggestions if they aren’t well-thought out.

    Before you ask a question of your manager, ask it of yourself.

    Is it something you can figure out on your own? Then do that. Would a co-worker know the answer? Ask them instead of your manager.

    Is it something that has a few different possible answers? Incorporate those into your question to show your manager you are putting thought into the question and not expecting to be handheld through it.

    Do you need to know the answer immediately? Is your manager pressed for time? Can it wait and be put in an email to be answered at their convenience?

    Do this and you’ll find you don’t have quite as many important questions as you think.

    Reply
    1. Critical

      Especially since the letter comes across as she’s not even trying to think of reasons why her manager might feel that way – her first instinct is to ask someone else. If this is how she’s asking ‘why’ at work, I can see why her manager is frustrated.

      Reply
  48. JSPA

    see whether “how does that process work” (varied with, “what’s the history of X” and “I really like how Y worked out, is there some trick to getting that result reliably” and “is there documentation I could read on how Z works” etc) help to detach the “I’m curious about this thing” from “I’m questioning this thing.”

    But first, remember the “does this question need to be asked? Need to be asked now? Need to be asked by me?” triad.

    Your boss is there primarily to do a job, and you’re there primarily to support your boss in doing so. She’s not there to entertain you, and she’s only minimally there to educate you.

    I’m curious about basically everything. How the A/C works, etymology, cultural variations in the norms of interpersonal dynamics, what causes paint to peel. None of which is the least bit relevant to my job. Those questions are easy to avoid, because they’re clearly an indulgence.

    I’m also curious in things closer to my job. But really, truth be told, getting an answer to those questions is just as much a distraction as chatting about the completely unrelated stuff. If you’re asking any of those–back way the hell off. You’re not actually getting job-relevant training by asking them, and you’re distracting others, and wasting on-clock time. (You’re allowed to waste your own time…on your own time.)

    Finally, there are all sorts of things that are a bit more relevant to the job, but that are not the boss’ job to teach you, at your demand, at the time of your choice.

    If it’s not something both relevant and pressing, do the google search / check the documentation / pay attention to the repeated patterns yourself, and see if you can find your own answer. Failing that, make a list of “things I wonder about,” write it up ON YOUR OWN TIME, and include your best guess of the best person to ask (likely not your boss). Then offer to spot those people to a coffee–outside work–and get your answers off the clock.

    Reply
    1. TootsNYC

      “Need to be asked by me?”

      I’ve started applying this question to myself. The chances are very high that someone else in the meeting will have the same question and will ask it.
      Now I’ll write down a note about the question and wait to see if it gets answered–either by the person speaking, or in response to someone else’s quesiton.

      Reply
  49. Bubble Gum Top

    As some commenters have already pointed out, asking after completing the task can help A LOT (when it’s possible to do so): first you get to do the task and might understand while doing it why it had to be done, or why this particular point was critical. And second, it will not seem defensive, if that is part of the issue here. I know that I would respond well to it, as I got what I needed done, the person tried to figure out by themselves and is showing commitment and interest for next time.

    I had a similar issue with an intern last year: he was full of initiatives, which seemed great at first, but it quickly became very annoying ! He would offer “better” ways of doing before actually trying to follow our usual way of doing (in this case a question on the “why” we do it this way would have been better received than an unsolicited and often irrelevant suggestion !), our suggesting things that didn’t make much sense (no we will not invest a lot of money to control better this parameter that has very little impact on what we do…). In his case, his suggestions clearly showed a lack of understanding and little effort to understand and it came off as overly confident.

    Reply
  50. Archie Goodwin

    I would just like to note, for the record, that there’s a Russian word for someone who asks “why” all the time – “pochemuchka” (literally “why-er”). Perhaps it’s not germane, but it’s a great word, and I’m determined to drag it kicking and screaming into the English lexicon.

    Reply
  51. Agent Diane

    I don’t think this has been covered yet, OP, but do you have a clear picture of how your role supports the bigger picture? If you need to see the wider context in order to see how the task you are being given fits in, perhaps what you really need is a sense of your role and purpose. You can then reduce the number of task-specific “why”s to something like “Could you clarify why I’m doing this rather than Bob in teapot handles, as I don’t quite understand how it fits with my role proving teapot spouts?”.

    Reply
  52. AMPG

    This sounds a little like the difference between “process” workers and “outcome” workers. Some people work best when they have (or create) specific steps to follow, while some people need to understand what the end result is supposed to be so they can reverse engineer the process for themselves. Both types have their advantages and drawbacks, but the biggest issue is that it’s really hard for one type to communicate work instructions to the other type. I suspect the OP is an “outcome” worker and her boss is a “process” worker. So the boss’s instructions don’t contain enough contextual information to be useful to the OP, while the boss doesn’t understand that the OP is missing information that will help her do her job correctly.

    Reply
    1. Brownie

      Oh, this clarifies quite a bit of some interactions between me and a few of my coworkers. I’m an “outcome” worker, tell me what the end product is so I can figure out if I have all the knowledge/instructions to get there. “Process” workers drive me up the wall since I can’t tell if “Step 1: Gather clay” will actually lead me to a teapot versus a brick in the end, especially if the steps/process isn’t explicit enough to eliminate all other possible results. If I know it’ll be a small glazed teapot at the end then I can figure out how much clay of what type to gather in step 1 without having to ask “Why” questions during the process.

      Reply
  53. Drama Llama

    Frequency of the “why?” matters, too. If you’re asking occasionally for a manager to explain her instructions to you for better context, that’s fine. But it’s frustrating to justify instructions frequently when you just need stuff done. Asking “why” too many times comes across as demanding your manager to convince you that a job is worth doing.

    Reply
  54. Utoh!

    Yeah, my face betrays me every time when my manager or anyone on the team decides something (without ANY context behind it). That’s the main reason why I ask questions so I can better understand the thinking behind a decision, or a question I am asked. My boss always calls me on the phone to ask for a quick answer, but rarely do I have one for her because her questions usually involve me needing to do some research. I like having the whole picture so I can provide a cohesive response, but I’ve learned that so many people just want to shoot from the hip and deal with any fallout after the fact. I’m by no means a slouch, and am extremely responsive, when I get all the necessary information. I won’t EVER stop asking why, it’s part of the fabric of my DNA.

    Reply
    1. Cheryl Blossom

      I don’t know exactly what you do, but I think it’s definitely worth considering that there’s times when stopping to gather ALL the information is just slowing the process down– it might be more important to make a decision quickly with some information rather than stopping and getting all the information possible. Or your coworkers might be making decisions with information you don’t have, but that doesn’t mean the decisions aren’t being made without any context at all.

      Reply
      1. Utoh!

        I work in IT, so often changes we make could have unintended after effects if we don’t plan, discuss and yes, ask a lot of questions. I can see your point, and perhaps should include that I am also constantly making decisions around issues and requests I am presented with and acting on those decisions. I often go home with decision-fatigue and have to rely on my husband to decide what we are having for dinner! :)

        Reply
  55. Bibiddy

    So much depends on the phrasing, frequency, and overall attitude of the person asking. In general, I’m happy to explain the reasoning behind things, but sometimes I just need things done and do not have the time to give more detail than “this is the process that 12 people have agreed will work after months of conversation.” If the person doesn’t question everything and is generally amiable, it’s not a big deal. However, I have one staff member who is abrasive and aggressive and who thinks she should be in charge (and I can’t do anything about her because of upper management… it sucks), and the way she asks always seems like a confrontation. I now understand why parents yell, “Because I said so, that’s why!” I haven’t done it at work, but I’ve certainly been tempted.

    Reply
    1. Observer

      Sometimes that’s not an entirely unreasonable response, to be honest. If you’re doing that a lot then something is wrong – either you are not managing right or you have a particularity problematic employee. But sometimes you just need to shut the conversation down.

      ONE time, I told someone I managed “OK. I’m pulling rank. We’re doing it my way.” To heir credit, they backed down right away, and also learned a lesson going forward. As long as they worked for us, they never pushed an argument that far again.

      Reply
  56. whistle

    OP, are you literally just asking “why”? If so, that is putting a lot of mental labor on the person you are asking, especially if that person genuinely wants to give you a satisfactory answer. Since this is a pretty open-ended question, the listener has to try to figure out what type of information you are looking for and then deliver that information to you. This can be exhausting. I would recommend asking more specific questions to clearly identify for the listener the type of information you are looking to obtain.

    In brief, you should be doing the mental labor of figuring out what information you need and asking for it instead of asking a broad question and leaving the listener to do the mental labor of figuring out what information you need.

    Reply
  57. LQ

    I normally love it when someone asks why questions, and I try to preemptively explain why on a lot of stuff too.

    But I have a project right now and the person (WHO IS AMAZING) keeps asking why because she knows she hasn’t gotten to the real root cause, which would normally be great. But the problem is the root cause on this one is her boss, and her boss’s boss, and her boss’s boss’s boss are incapable of doing the other thing we really need done so we’ve created something that will let us work around that problem to get to the goal we want. I can’t say what I want to say which is, “While you are one of the best people I’ve worked with in a long time your leadership stinks and won’t get anything done so that’s why this project looks like this, because it’s the only thing I can get them to do.”

    All this to say, there may be a reason that is unspeakable. And sometimes that means you have to lay off asking because they can’t answer in a way that will be satisfying. I’d say this is especially true if someone is normally open.

    I’ve been successful at getting answers to questions of why coming at it from the side or being willing to wait for the answers too. I had a why I was really curious about, though it wasn’t super pressing, and I kept just sort of coming back to it with different people from different angles occasionally. 3 years later the pieces all came together and I’m super glad I didn’t relent entirely.

    Reply
    1. JSPA

      Eh, there are ways to say “you’re great, it’s funky, stop pushing.”

      e.g. “that’s a great question in the abstract, but for various reasons the constraints we’re working with are not up for discussion. Not, now, nor for the foreseeable future. So let’s tighten the focus down to what we can do here and now.”

      Reply
  58. Jenna Maroney

    Agreed with other commenters that it’s generational. Hope that makes taking it a little easier, OP :/

    Reply
    1. Not All

      Could’t disagree more. The worst “but why why why” toddler of a coworker I’ve ever had was in her mid 60s

      Reply
      1. Not All

        Sorry, that came out really nasty.

        I don’t think people who ask ‘why’ a lot are necessarily acting like toddlers…this particular coworker was exceptionally problematic on many fronts & still gives me nightmares

        Reply
  59. Kella

    I had a manager that I used to butt heads with because I would question why we were doing things a certain way (and sometimes asserting that my way was better or that the way she was asking me to didn’t make sense). She would get angry and I would get frustrated that I had to do a task in a way that was less efficient, etc.

    It took me time to understand that because she’s a small, soft-spoken woman, she has her authority undermined ALL THE TIME. Customers would make faces at her and go, “*You’re* the manager?” when she’d arrive to assist them. Our job is also pretty fast paced so explaining why she wants something would take up valuable time and stress her out.

    I learned that it was best to do as she asked in the moment, and then when things had calmed down and the task was already done, ask her about why we had done things that way, and maybe even suggest an alternate way to do it next time. When I approached it this way, she was much more receiving and we eventually developed a great relationship.

    Reply
  60. Cat mom

    I’ve found the softer versions to be quite successful:
    “I’d love to know more about this – is there a web page or SOP I could review?”
    “Do you have time to give me a little more background about this approach?”
    “This is new to me, so I would appreciate a little more of the backstory if you have time. Or perhaps you can point me to a colleague who has already been involved and knows more.”
    “Yes, of course, I will do [—]. Can you please say a little more about your goal here?”
    In general, indicate your willingness to cooperate and support the effort and then be spacious about timing.
    Good luck

    Reply
  61. Former Retail Manager

    Apologies if this has already been suggested by another commenter(s), but it sounds like OP is asking “why” pretty frequently because they are new, either to the org or the role. I’d suggest buddying up with someone who has been around a while with whom you have a good rapport, and maybe asking them your why questions shortly after the meeting, if that’s feasible, unless the why is something that you believe only your manager would know.

    We recently completed training for our most recent batch of new hires. You are considered to be in training for your first 2 years in the position and there are various phases of training. During the training process, the new hires were assigned a trainer and were told not to ask their manager “why” questions, if at all possible, and to instead to direct those questions to their trainer, which worked out pretty well. The org is large and encumbered by a multitude of processes whose existence/reason for existence is not intuitive in the least. You really have to learn by eavesdropping/overhearing other folks talking about stuff or by someone telling you that System A does not communicate with System B and therefore, report X will be incorrect if you do not fill out Form Y correctly by Z date. Now that all of the newbies are finished with training, each one has formed relationships with various folks around the office and will still ask “why” type questions from time to time.

    Also, it’s all in the delivery, as Alison’s response indicates. There’s always a way to soften the “why” request.

    Reply
  62. Yourskrewely

    Wow, I am super surprised that no one has mentioned that you are a Questioner under the four tendencies! Check out the book by Gretchen Rubin with the title The Four Tendencies.

    Reply
  63. Tipcat

    I want to emphasize the importance of reading the situation. I once had a job where the Friday version of Murphy’s Law was in effect–Anything that can go wrong will do so at 4:45 on Friday afternoon. The non-exempt people would go home at 5:00, but we exempt people had to stay until it was fixed. So when the boss was giving out tasks as quickly as possible to get the situation under control enough that we could eat supper at home, we did not ask for explanations of the orders. But one clerk never seemed to get this. When she was given a task, she kept asking ‘why’ and pestering us with motivational-poster platitudes about the importance of explanations for her professional development. She was usually told ‘Because that’s what you have to do if you want to keep your job.’ She For this and other similar reasons, she was not seen as a team player and was widely disliked.

    Tl;dr You gotta read the room.

    Reply
  64. Observer

    OP, in re-reading your question I realized something. If the framing of your question is similar to how you frame the questions you ask your boss, then there is a very simple reason your boss sees it as questioning her authority. You totally sound like you are questioning your boss’ judgement and the appropriateness of their reaction. I do understand where it’s coming from in this situation, but probably not what you want your boss to be hearing.

    Reply
  65. Properlike

    Has anyone brought up Gretchen Rubin and The Four Tendencies yet? Basically, most people fall into one of four categories, including Obliger, Upholder, Rebel, and… Questioner. People who are natural questioners (raises hand) tend to drive other people batty simply because, if you’re not a questioner, you see questioning as challenge. Questioners see questioning as “I need this information in order to understand” or “I’m curious about how this works.”

    Knowing that about myself, and that it’s a temperament style, helps me manage it in the workplace where I can come off as obstinate when really, I’m trying to drill down into an explanation that will help me be the most efficient at the task.

    Reply
    1. Not My Regular Username

      I mentioned this somewhere else upthread, but I’m a Questioner myself, and I get pretty fed up with Questioners who don’t seem to seek answers to their own questions without creating more labour for someone else. It’s not about being defensive or seeing questions as a challenge – it’s more a matter of feeling that satisfying one’s curiousity doesn’t necessarily entitle them to creating a derail for others. I’ve enjoyed managing the more effective kinds of Questioners because they have a good eye for process improvement and know how to read the room to help build their knowledge.

      Reply
  66. Anat

    I know that’s not a useful addition to the discussion, but I just couldn’t resist:

    By Rudyard Kipling:

    I KEEP six honest serving-men
    (They taught me all I knew);
    Their names are What and Why and When
    And How and Where and Who.
    I send them over land and sea,
    I send them east and west;
    But after they have worked for me,
    I give them all a rest.

    I let them rest from nine till five,
    For I am busy then,
    As well as breakfast, lunch, and tea,
    For they are hungry men.
    But different folk have different views;
    I know a person small—
    She keeps ten million serving-men,
    Who get no rest at all!

    She sends’em abroad on her own affairs,
    From the second she opens her eyes—
    One million Hows, two million Wheres,
    And seven million Whys!

    Reply
  67. Scrappy

    As someone who is irked by folks who are frequent “Why?”-ers, here are some reasons it bothers me (any or all could apply):
    1) It’s near-zero-effort on the asker’s part and demands effort from the asked. It often comes off as if the asker hasn’t put any effort into understanding what has just been discussed.
    2) It often signals that the asker hasn’t been paying attention.
    3) It’s overly simplistic and vague. It doesn’t explain what the asker doesn’t understand or needs clarification on. It makes the asked play guessing games and/or causes them to go off on irrelevant explanations because they don’t know what’s really being asked about. The question should be fleshed-out past a single syllable.
    4) Depending on the demeanor/attitude/methods of the asker, it’s not really a “Why?,” but a “Justify it!” demand.
    5) “Why?” is a substandard question for nearly all scenarios. If you’re an adult, formulate a better question.

    Consider this scenario based on events from my last weekend. I’m an event chairman for a large car club and discussed the happenings of the event at a board meeting earlier this week. Contrast the first hypothetical discussion with the second (a playwright I ain’t — apologies):

    Me: “We were unable to get the truck from the track infield until 45 minutes after the contract time, so I decided to delay the event start by 30 minutes.”
    President: “Why?”
    Me: “Well, we were already down the number of setup crew, so we could probably not make up the entire 45 minutes in the remaining hour and a half.”
    President: “But why?”
    Me: “One was on a business trip, one was at a funeral…”
    President (getting frustrated): “Never mind all that — it’s not what I’m asking. Why did it take you an extra 45 minutes to get the truck?”

    … now without the “Why?”…

    Me: “We were unable to get the truck from the track infield until 45 minutes after the contract time, so I decided to delay the event start by 30 minutes.”
    President: “What was the cause of the 45 minute delay?”
    Me: “The track had not properly scheduled their workers, so no one was there to open the gate.”
    President: “Oh, then that was not an issue from our end that we need to correct.”

    There are much better questions than “Why?” Try to never use it.

    – Scrappy (long-time lurker, first-time poster)

    Reply
  68. CM

    This is one of those things where it’s hard to say what’s going on without knowing the personalities of the people involved. FWIW, when I was a manager, I didn’t see it as a challenge to my authority when people asked why we were doing something or if they straight-out told me they didn’t agree with what we were doing. A challenge to my authority is saying “You don’t have the right to make this decision” or disregarding my decision and doing something else. Discussing the decision, or questioning whether it’s the right decision, is totally normal and fine and what I actively wanted people to do. I don’t WANT to make a mistake, so it would be awesome if my team would tell me when they think that’s what I’m doing.

    I do think some of the other commenters have a point that there are some offices where nothing anybody does is ever going to make sense, so trying to understand why is an exercise in futility, but, even in those situations I find it hard to see myself getting annoyed because people want to understand what’s going on. But I also find it hard to imagine myself just accepting that nothing makes sense instead of pushing back on it. So, again… personalities.

    Reply
  69. DSoc

    Comming from organization with very open culture that genuinly encourage asking questions and searching for meaning; being a person who hates doing things without knowing why … I do get annoyed when someone asks (too many) questions. I am more than happy to explain meaning or inner workings, but one of my reports has habbit of asking why and how questions without even going through the assignement first or trying to figure them out for themselves, or when we already discussed them before (several times).
    OP, I wonder how your coworkers deal with this – do they all ask so many questions? If not, and you know that they also are those people who needs to understand, what they do differently to get it?

    Reply
  70. Liz

    We don’t know the gender of OP here, but I also want to throw it out there that this can be related to gender bias. Men often don’t have to think about their tone or positioning of the questions they ask, even “why?” questions.

    Reply
  71. WillyNilly

    I feel like agreeing (assuming its a reasonable task) first is the key. Boss asks you do something, reply “sure, no problem I get that done by X. So I can be sure to take it the right direction, can I ask the reason it needs to be done?” Bam, non confrontational because you have already agreed; Why away. Its exactly what Allison’s example does – agrees to the boss’s directive first while still asking why.

    Reply
  72. Safetykats

    So – if the question repeated over and over is simply “Why?” part of the problem is that you sound annoyingly like a 2-year old. Alison’s second question is much better, mostly because it show some thought on the part of the questioner, as well as a desire to use the information to improve.

    I don’t know that you can make this a generational thing. I’ve got a lot of people on staff (of all ages) who have a good questioning attitude. The difference between the best of them and the rest isn’t the questions – it’s the level of maturity and thought in the questions. When staff ask good questions, it’s often an opportunity for me to learn also.

    It’s also worth thinking simply about how much of your manager’s time you’re taking, and whether you could learn what you’re asking from peers or senior staff not in a management position. It’s never a good idea to consistently make more work for your manager, or to take more of her time than you’re fairly owed. If your questions do both, finding a working-level mentor is a better idea.

    Reply
  73. Lamb

    LW, you write that your manager perceives your “why”s as undermining her, and your response to that is to wonder why she feels this way. There’s literally a reason why she wants you to ask fewer questions right in the explanation, and you still want to question it.

    Based on your letter I have several points of feedback:

    If “why do you feel that way?” is in your regular rotation of questions, cut it out immediately. Theoretically someone somewhere might benefit from a sympathetic person helping them examine the source of their feelings, but that is NOT the point in reality that you occupy. Based on the reaction you are getting, you do not come across to your boss as asking your questions in a sympathetic or supportive way, so any question that requires the assumption that you are trying to help in order to come across right IS GOING TO LAND BADLY.
    In particular, saying “why do you feel like I’m undermining you?” comes across as an attempt to invalidate that perception (which is an additional form of undermining someone, FYI). (Side note: “why do you feel that way” is also generally irrelevant in most work contexts)

    Are you asking “why?” in response to the answer to your previous “why?”, because that is exhausting to deal with (I ask because that’s what you do in your letter). People will dread you asking even one question because they expect one to turn into a cascade of questions with no way out. It makes you seem impossible to satisfy, which makes you difficult to work with. It’s also a time honored method of wasting time, so even if your interest is sincere, some people will see it as intentional procrastination.

    You admit your questions are about “how everything fits together”, and sometimes your boss won’t know, either because she didn’t ask about aspects not relevant to what her team would be doing, or because she’s not high enough in the hierarchy to be looped in on the aspects you are asking about. Pointing out either of those things would reasonably be seen as an attempt to undermine her, including if you point them out by asking questions.

    Sometimes questions shouldn’t be answered to everyone. Someone above mentioned situations where the answer is confidential such as someone getting fired or the company possibly being sold, but there are also the situations where the answer brings up a problem that has already been dealt with and looping you in has no benefit (and might adversely effect business relationships)
    Q: why does this client have an unusually favorable contract?
    A: Because Doug made a mistake in the paperwork
    Q2: but why is Doug still here?

    Or
    Q: why does accounting always call to verify dates and delivery counts from this vendor?
    A: We are Teal Pots Inc. and sometimes they accidentally switch our invoices with those for Tea Pots Etc.
    Q2: then why do we still buy from them?

    Notice how in both examples the answer leads to a new question? But neither the original questions nor the follow-ups would lead to the questioning employee to do their job better, they are all just satisfying their curiosity. It’s not a good use of your or your manager’s time to rehash this stuff.

    For the first example, maybe Doug successfully completed a PIP, or maybe they let it slide because Doug is generally a superstar- neither is your business, either could effect your perception of him, and management is already dealing with him as they see fit.

    In the second example, the powers that be have decided that it is worth it to do business with this vendor. Maybe this vendor is 60% cheaper than the competitor, maybe your company doesn’t make a fuss because their accountant is the owner’s kid, maybe a million things that you don’t need to know in order to say “yes, 7 cases came in on the 21st”.

    My last point is an important one. You need to repair your relationship with your boss. She thinks you’ve been habitually undermining her, so even if you were able to completely change the way you act overnight, things aren’t going to suddenly be golden. You need to let her know you finally understand about the questioning and actually stop, but you also need to make clear with your words and actions that you have her back. If you want her to believe you hadn’t been trying to undermine her before, you need to make sure you’re not undermining her going forward. You have used up all your goodwill here and you really need to build it back up.

    Reply

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