Questions You Should Ask Your Boss

8 Questions You Should Ask Your Boss

The manager-subordinate relationship is unnatural by design. We exchange our power for money. We look to a person we have not chosen (whom we may or may not respect) for affirmation, evaluation, and reward. In order to “succeed,” we strive to figure out what will make this guy like us, and adjust our style accordingly. We take every criticism to heart even when we don’t believe it. And yet it can be scary to ask your boss what’s really on our mind.

Elizabeth’s Ask Your Boss Story

Every time “Elizabeth” asks her boss, Carol for feedback, Carol tells her she’s “doing great.” But this is Elizabeth’s 5th year in the same job and she’s starting to wonder. She’s watched peers who don’t seem any more qualified get promoted or selected for special assignments.

Her performance reviews are always solid, but never outstanding. She likes her job and the people she works with, but she’s beginning to feel like she’s treading water. Her mentor tells her, “just ask your boss,” but every time Elizabeth’s tried to approach the subject, she’s chickened out.

Elizabeth needs to set up a meeting with her boss just on this topic, rather than trying to squeeze it in as a footnote to some other meeting. She should also do it outside the context of a formal performance review. Let this be its own event. Here is an approach, I’ve developed to help Elizabeth– maybe you will find it helpful too.

Questions You Should Ask Your Boss

Start by sharing how interested you are in her insights. A little flattery can never hurt in this arena 😉 Express your desire for deeper feedback that will help you be more effective for the company. Ask for specifics that will help you identify some new behaviors to increase your effectiveness.

Take it all in and step back and consider the possibilities from the conversation. You don’t have to agree with it all, but if you want to open the door for richer insights, it’s important that you respond well.

Of course, you don’t want to bombard your boss with all of the these in one sitting, but here are some options to get the conversation started. It matters less what you ask, then just getting the dialogue started.

  1. What’s the most important priority for our team this year?
  2. What do your peers say about me?
  3. If your boss were to give me one piece of advice, what would it be?
  4. Who should I be working with more closely?
  5. What could I be doing to make your job easier?
  6. To what do you attribute your own career success?
  7. How can I be more effective in that area?
  8. Which parts of my style concern you the most?
  9. Specifically, what do I need to work on to be ready for ___________ (insert the job or assignment you are most interested in here).

You have more power in your career than you may think.  Take the time to invest in yourself by starting a good dialogue with your boss.

You can download our FREE MIT Huddle Planner here to help. 

For more career advice, see also 10 Common Excuses That Silently Damage Manager’s Careers 

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Posted in Career & Learning, Communication and tagged , , , , , .

Karin Hurt

Karin Hurt helps human-centered leaders resolve workplace ambiguity and chaos, so that they can drive innovation, productivity and revenue without burning out employees. She’s the founder and CEO of Let’s Grow Leaders, an international leadership development and training firm known for practical tools and leadership development programs that stick. She’s the award-winning author of four books including Courageous Cultures: How to Build Teams of Micro-Innovators, Problem Solvers, and Customer Advocates and Winning Well: A Manager's Guide to Getting Results-Without Losing Your Soul and a hosts the popular Asking For a Friend Vlog on LinkedIn. A former Verizon Wireless executive, Karin was named to Inc. Magazine’s list of great leadership speakers. Karin and her husband and business partner, David Dye, are committed to their philanthropic initiative, Winning Wells - building clean water wells for the people of Cambodia.


  1. Karin,

    One to add could be: “Looking out 12 to 24 months, what challenges do you see ahead?” Identifying what is “keeping them awake” may lead to finding new ways to jump in and take a lead in solving what lies ahead. I appreciate the ways you outline to better engage in more fruitful conversations.



  2. Karin- first, if we don’t ask we don’t get answers. It is fulfilling that you started your post to encourage asking questions.
    Creative questions may remove many hurdles. I wrote a presentation on how to ask one question to reveal the profile of an employee to some extent.

    The question I would add here: What achievements counted in promoting star performers in this company so that we may learn from them?

  3. Karin- just kind of firing back at you, I have a question for you. What was the most moving comment you had from your commenter and why? This is to learn how to write better comments and to tell you that you are the “boss” here.

  4. Ali, Thanks so much for sharing your terrific presentation. I love it when our LGL community expands the conversation by sharing their creative work.

    Now, you know I can pick just one comment. The truth is, I am so grateful for all engagement, because I believe that’s what makes this community strong. I’m delighted when folks in the community share their experiences and link to their own work, and it’s fantastic when the conversation starts happening amongst our crew.

    • Thanks, Karin. Having done your word cloud I know you better and I knew you would answer the way you did. I extract the following from your response to me:
      love it,
      so grateful,

      Excuse me, Karin as I don’t feel much attached to the word boss. I prefer leader. The extractions from your response to me shows your leadership style and your consistency. Your word cloud hasn’t changed.

    • Ali, Thanks again for diving in so deeply. I hate the word “boss” too….and I try never to be the “boss.” With that said, there is a power dynamic in most organizations… so every now and then I use that word deliberately to help folks working to navigate in that environment. I actually just finished my first “book” it’s actually an interactive guide for people to help build a better relationship with their boss. It’s call Overcoming an Imperfect Boss: A Practical Guide to Building a Better Relationship with Your Boss. I just sent it off to an artist this am. I’m quite excited to be nearing completion of one of my 1Q goals.

    • Steve, I agree with you about creating those outside of work connections. Sharing common interests draws people together… and yet, I see so many folks shy away from these discussions… trying to keep things more “formal.”

    • Steve,

      I was just about to post your’s “How can I help you?” It’s so powerful to get into the issues of the other person in the conversation…


  5. When talkign to a boss i also like to ask teh questions: 1. How do you prefer to communicate, and how often? That way there is no confusion and I clearly understand the boundaries in which we will operate. 2. Do you consider me a team player in accomplishign team goals? I liek to ask this because it typically leads to examples of where you have done a great job in accomplishing this goal. It provides insight in to the projects or tasks you have worked on and keeps it at the forefront of your bosses mind.

    • Shayne,, Wonderful adds… Communication preferences really vary. Nailing your communication is a great way to look brilliant without much additional effort 😉 Thanks for extending the conversation.

  6. This weekend, I started reading, “Its Your Ship” by Captain Michael Abrashoff. It’s a wonderful leadership book filled with valuable lessons – one of which fits nicely with this conversation.

    As leaders, we need to get down to the grassroots level of those who follow us and truly get to know them. Abrashoff made it his mission to learn the name and a little bit about ever crewman aboard his ship by contacting five or more personal interviews each day. By doing so, he made a safe environment for those to come to him directly.

    If an officer in the Navy can buck the traditional system of command and control, and be a transformational leader, it’s certainly within the reach of all of us working in private industry.

    Love the thoughts, Karin!

  7. Karin, we all get those doubts and voices that decide we aren’t good enough (especially women). Asking questions and getting curious about what you can do to advance improves communication with your boss and shows initiative and interest. In addition to the fact finding mission with the boss, what if someone also asked those peers that advanced what they did to get there? An additional question for the boss though, might be, “I’d like to increase my skills/critical thinking. Who would you recommend as a mentor beside yourself?”

    Sue Bock

    • Sue, You raise an important point… why do so few shy away from this conversations? Is it that we fear what we will hear, or that we some how deserve our current state. Thank you for adding that.

  8. I love all the questions, but the first one seems to hit the nail right on the head: what excites you about your work and is the most fulfilling?

    If we can answer that question, we’ve done most of the work ourselves. The rest is finding out how to put that energy to work.

    Great list of questions, Karin.

  9. Love the idea of initiating this dialogue with one’s boss! It is so helpful to get into the habit of doing the reaching out and asking for honest feedback. That’s what we learn the most from.

    Last week I approached one of my clients about how she felt my program went and what she would change. She offered some incredible ideas which I am incorporating into my future presentations. I guess we also have to be open minded to receiving answers that may throw us.

    Enjoyed the post, Karin!

  10. Ray’s questions are fantastic! No wonder it weeds people out – they’re tough too!

    As for Elizabeth, you’ve outlined some great questions. I was in a similar circumstance many years ago. While I was steadily promoted, I could tell that my new boss didn’t like me (or at least that was what I thought) When I finally found the courage to ask for time to meet with him not to talk about the work at hand but about my performance and our perceptions of each other, everything changed for the better.

    I would add that finding the courage to ask for the time and step into a tough conversation is infinitely better than suffering for months (or years) on end.

  11. Great questions Karin! I’d add two questions for a boss asking their employees: first how can I help you, second what are your passions and dreams. This shows your followers or employees that you care about them.

  12. Hello..I am an army officer..we know that a leader in army/armforces is different..a leader in an army organisation is a commander..a leader is not a manager..some parts or roles are same..but some parts are question is, what is your opinion on how to ask a senior commander on leadership..I mean the question I should ask on to the civilian organization.

    • Haiqal, That’s a tough one, given that I’ve never served in the military, maybe some others may chime in. With that said, even within appropriate boundaries, I would chose to ask questions about how I’m doing and how I can improve, as well as how I am perceived… those work well across any context. I think most on this list would still work. And I would imagine as you get to know the person, even some of htthe more personal ones woud be appropriate some where along the line.

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