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Why You Need to Ask More Questions


why you should ask questions

I had an important project at work a few weeks ago. One that I knew my boss would comb through once I sent it to her. Sometimes it feels as if no matter how hard I work, there will always be something that needs to be fixed, changed, altered.

Over the time we’ve worked together, I’ve tried my best to get inside her head when approaching what she assigns me. I try to anticipate what changes she’ll make, what she’ll look for, and what her feedback will be. I hate seeing edits in red or getting emails with a bullet list of follow up items. I want my work to be perfect the first time. Who doesn’t?

So I spent hours working on this project. Hours reviewing spreadsheets, making sure the information was accurate and organized in an easy to read fashion. I spent so much time on it that my eyes blurred and my head ached from repeated reviews. And usually when this happens, it means I’ve done the best I can do.

I sent the project along, expecting her to just say thanks and great job; but when I opened my email, I saw something else:

This just isn’t up to par. I need you to revisit this for the following reasons:

Queue six issues she found that I hadn’t thought of or anticipated.

Initially, I was upset. I even ranted to myself with a bunch of rhetorical questions.

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Does she know how much time I spent on this? I did exactly what was asked, am I supposed to be a mind reader? I’m told to be more independent, but then when I am, this happens. What could I have done differently?

And it was the last question that sparked my introspection. It turns out there was nothing I could’ve done while working on the project. Yeah, I could’ve checked in during, but even then would’ve been too late. Everything I could’ve done needed to be done before I even started. I was so focused on being perfect, so focused on being independent, that I opted not to ask additional questions when she said “do you have any questions?”

“No. I’ve got it. I’ll get this taken care of.”

I got it taken care of, but I didn’t get it taken care of to the expectations that were unbeknownst to me. It would’ve been easy for me to say “Well, you didn’t tell me all that.” But the truth is I didn’t seize the opportunity to talk through specifications to make sure the product was delivered exactly as she wanted. Yes, it would’ve been an additional five to ten minute conversation up front. It may have required more guidance than she wanted to provide, but it would’ve saved us both time and frustration.

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The definition of quality varies from person to person. What you see as excellent work may very well be considered lackluster in the next person’s eyes — maybe even in your significant other’s eyes. And when it comes to work, which is a synonym for relationships, you can’t deliver on expectations when you’re not clear what they are. You can’t not ask questions because of how you think you’ll look to the other person — whether than means inexperienced or clueless. You should be willing to admit to both; because once you address it, that issue is no longer on the table.

Ask questions. Eliminate the issues.

slim jackson


Twitter: slimjackson


  1. My boss sounds like your boss, except worse. I actually DO ask questions ahead of time to get a clear understanding of exactly what she wants. I'll even repeat back what she's asked for to make sure we're on the same page. But, lo and behold she'll STILL come back with changes and corrections.

    To continue your work/relationship analogy… Sometimes our S/O's have no idea what the hell they want, and we just have to realize that we can't always make them happy no matter how hard we try or how many questions we ask.

    1. Dude, you two need to get out of my head. I ask questions as well, but somehow when I get the proposal back, it has tracked changes for BS that wasn't even in the original concept. Seriously? This is really getting on my damn nerves.

      Let me give you one better. How about when you make suggested changes and turn it in, then the document is returned yet again with changes made to the suggested changes. WTF? You just changed your own changes fool. Okay. I need to calm down and sip some water.

  2. Good article.

    I think people get the wrong idea when you don't ask questions right away. I don't because I don't know what I will run into that I will have questions on, once I run into something I have a question on, I will ask it. But I have learned to ask 2 or 3 questions just for perception's sake.

  3. Yeah..I used to be of the "some things are worthless if you have to ask for them" school of thought. Now I am ALLLLL about the "closed mouth doesn't get fed"!! I assume you don't know something about me unless I tell you, and I would like the same, as I can't read minds (that well, hehe).
    And Slim, don't feel so bad. I had a boss that just assumed I would know., and would get volcanic if I asked for clarification. THEN would send stuff back completely red marked. THEN when I did it exactly to their specifications I was berated for not "being original and having independent thought." After a while I just gave up and sent anything. Fun times.

  4. I think we can all relate to the work/expectations struggle. That’s why I’m working my way up the corporate ladder, not because I care per say but because I need as few people above me as possible. Feels like Office Space over here sometimes.

    And when it comes to work, which is a synonym for relationships, you can’t deliver on expectations when you’re not clear what they are.

    Also, I like this line and hear it often but I’m not sure I agree. I actually had this exact debate on Twitter last week. I know relationships take work but I def don’t want my relationship to feel like work. IMO it really shouldn’t be that complicated but maybe I’m just wishfully thinking.

    1. I see the counter. Putting it back in the job context, you can basically automate a good amount of your job so that fire drills turn into bathroom breaks. But when something new comes up, you address as much. I think relationships are much of the same. Work doesn't have to mean arduous or struggle.
      My recent post slimjackson: RT @OG_Humble_One: I've watched too many qualified ppl get passed over for not having a degree. I think this one reason why a college ed …

  5. Speaking to the relationship side of this post, I admit that in the past I have continued on doing the work and not asking questions, then wondering later why things turned out so poorly. I was afraid to ask them or he would think I was pushing. I didn't want to be perceived in a bad light. That experience taught me that if I am really invested in it, I should ask questions that pertain to our future. I shouldn't wait until we have both passed the point of no return to then broach the topic.

    In my last relationship, I did all these things, but I think he was on the other side of this conversation. I asked questions and got answers. He asked questions too, but disregarded the answers. He knew how I felt about certain issues but continued pressing on because he felt that even though he was of a different mindset, I would just tough it out to be with him regardless. You can do everything the "right" way and still end up on the losing end. It all just depends.

  6. I don't know…seems to me as if some may be taking this scenario a little too personal. Maybe the changes came about once they reviewed the project, they realized there was something they left out that should be added. Maybe the changes are not a direct attack on your hard work, but an attempt to collaborate with you and create a great project.

    At times it is hard to articulate every expectation. Personally I would much rather see your position and meet you half way. I am not sure why the "not up to par" reference was made. That was not good supervisor speak, it does not motivate only alienate. Even if you had any questions, you STILL may not cover everything, because the project was obviously a work in progress as you complete it (as is a relationship).

  7. I was feeling like this last week as I resubmitted a few guest articles to someone. After I originally submitted the articles, they were sent back and I was basically told the premise is good, but the work is trash. The kicker? The person was absolutely right. I asked what I could change, made the changes, and got one of the articles posted.

    The takeaway from that situation, and this article, is to gather as much information from people as necessary before you begin any undertaking.

  8. It's not simply asking questions up front, but asking the right questions, and those typically have nothing to do with the file. Find out who the target audience is, what is her role in presenting the material, are there other examples you can base your work on, what are the political impact will this document have.

    By knowing a bit more than the technical details, you can craft whatever it is to suit someone tastes, and definitely checking in mid-point for feedback is crucial and can avoid redoing major work.

    I said it before and I say it again, communication is key.

  9. It's funny because there is an editing function to my job, so I'm usually the one returning my boss's work to HIM telling him what needs to change and how my changes make his briefs sound btr. It's pretty cool, but when he does give me a project, I try to ask questions so that I fully understand what he is asking of me. What's even more interesting is that although has been a practicing attorney for 30+ years and I am an aspiring one, he trusts that I am a better writer than he is as far as mechanics go.

    In keeping with your relationship analogy, I think many relationships would fare better if each person understood their strengths and weaknesses and what the y bring to the table, and be able to fall back when dealing in an area that's not their strongest.

    A relationship shouldn't necessarily FEEL like work, but it is essentially work that comes with its own set of frustrations. Great post.
    My recent post Why I Didn’t Bother Watching “Life Is But A Dream”

  10. "You can’t not ask questions because of how you think you’ll look to the other person "

    Excellent point. I'm guilty of this myself, as I presume many people are. Sometimes some of us tend to get so concerned with how we will appear should we ask questions or a certain question, that we pay for it on the back end. Valuable time gets wasted and incorrect work gets submitted. In the end, the very fear of appearing inexperienced has now become a reality simply because the questions weren't asked.
    At this point in my life, I will ask as many questions as I need to shamelessly for full comprehension of direction and expectation. In the end, if the work doesn't come out right, I know who to throw under the bus.
    But seriously, the person providing instruction will have no choice but to hold themselves partially, if not completely accountable for not providing proper direction.

    Mr. SoBo

    My recent post ‘Django’ Unchained, Republicans Unchanged: Politics as Usual

  11. I agree.

    I've always found it very helpful (especially at work, but in life in general) to have dialogue as I'm doing things, especially when I'm trying to do them to someone else's standards. I see it as an important technique of active listening. So whenever I'm given a new "assignment", I try to figure out what they said, what they meant to say, and what they should have said. And this often leads to back and forth dialogue where I find out that what they're asking for is a rudimentary version of what's possible (like just asking for a basic web page instead of saying "blog" or "social media'" or "wiki page" etc.).

    And think this goes in work and in life in general. I'm always talking to people who tend to over or under exaggerate. So a lot of times, especially when they're making a request of me, I just ask questions to make sure we're on the same page. Like I said, I don't think listening is just sitting there quietly. I think part of it is asking the relevant questions to make sure that I understand cause if I don't said person will blame me.
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