8 Questions You Should Ask Your Boss

8 Questions You Should Ask Your Boss

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’s an approach and a menu I’ve developed for Elizabeth.

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’s some options to get the conversation started. It matters less what you ask, then just getting the dialogue started.

  1.  What specifically can I do to better support our team’s mission?
  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 arena?
  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).

Questions Your Boss May Ask You

One of the best bosses I’ve ever had, Ray, mentors hundreds of people in our company. He’s a very busy Sr. Vice President, but he’ll meet with anyone… on one condition. First they have to answer his questions. He finds this intimidating enough to weed out the casual employees looking for a quick fix, and leads to rich conversations with those who take the process seriously. We haven’t worked together in years, but when our paths crossed recently, he eagerly sent me his updated list to share with the LGL community.

  1. What are the things that excite and energize you about your work here? What are the things that drain or frustrate you about your work here? What have you done to reduce this frustration?
  2. If you were a super hero, what powers would you have? How would your powers help our company?
  3. How is your work/family balance? If not satisfied, what are you doing to change it for the better?
  4. How many people on your networking list would leave their position (or company) to join your leadership in a new department or company?
  5. What is your “sound”? How are you perceived by others. For example, a Harley Davidson has a unique sound that differentiates itself from other motorcycles. What is your business? How would others describe you? Would they know this the first time you met?
  6. What are some of your outside interests? What are the skills you are leveraging in these outside interests?
  7. What is your marketing or sales approach?
  8. We are at your retirement celebration. What position do you hold that you are retiring from at this time?

* Thank you Ali Anani for contributing a word cloud of this post.

If you like this post, you will enjoy my new book, Overcoming an Imperfect Boss, Available on Amazon.  Download a free chapter by clicking here.

Your turn: What questions should you ask your boss? What would you add to this list?
Filed Under:   Career & Learning, Communication
Karin Hurt
Karin Hurt
Karin Hurt, is CEO of Let’s Grow Leaders and a former Verizon Wireless executive. Karin was named on Inc.’s list of 100 Great Leadership Speakers for Your Next Conference, the American Management Association List of 50 Leaders to Watch, and as a Trust Across America Top Thought Leader in Trust. She’s the award-winning author of two books, Winning Well: A Manager’s Guide to Getting Results— Without Losing Your Soul, and Overcoming an Imperfect Boss. She’s regularly featured in business publications including Fast Company, Entrepreneur, and Inc.

Join The Conversation

What People Are Saying

Jon Mertz   |   03 February 2014   |   Reply


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.



letsgrowleaders   |   03 February 2014   |   Reply

Jon, Thanks so much. Yes! That’s a terrific addition.

Ali Anani (@alianani15)   |   03 February 2014   |   Reply

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?

Ali Anani (@alianani15)   |   03 February 2014   |   Reply

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.

letsgrowleaders   |   03 February 2014   |   Reply

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.

Ali Anani (@alianani15)   |   03 February 2014   |   Reply

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.

letsgrowleaders   |   03 February 2014   |  

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.

Ali Anani (@alianani15)   |   03 February 2014   |  

I want to buy the book as soon as it is published, Karin.

Steve Borek   |   03 February 2014   |   Reply

What’s the most important thing on your plate?
What can I do to help?

In general, get to know your boss outside of work. Ask questions about what they like to do.

letsgrowleaders   |   03 February 2014   |   Reply

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.”

Vlasta   |   03 February 2014   |   Reply


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…


Karin Hurt   |   04 February 2014   |  

Vista, Agreed. How can someone not like that question.

Shayne Farrell   |   03 February 2014   |   Reply

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.

Karin Hurt   |   04 February 2014   |   Reply

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.

Bill Benoist   |   03 February 2014   |   Reply

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!

Karin Hurt   |   04 February 2014   |   Reply

Bill, Love that book. And I heard him speak. So inspiring.

Sue Bock   |   03 February 2014   |   Reply

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

Karin Hurt   |   04 February 2014   |   Reply

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.

LaRae Quy   |   03 February 2014   |   Reply

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.

Karin Hurt   |   04 February 2014   |   Reply

LaRae, Thats what I found when that VP first gave me his list. It caused so much introspection.

Terri Klass   |   03 February 2014   |   Reply

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!

Karin Hurt   |   04 February 2014   |   Reply

Terri, Yes! It can work across so many contexts… we just need to ask!

Alli Polin   |   04 February 2014   |   Reply

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.

letsgrowleaders   |   12 February 2014   |   Reply

Alli, Thanks so much. Great story. It’s amazing what comes after courage.

Dan Black   |   11 February 2014   |   Reply

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.

letsgrowleaders   |   12 February 2014   |   Reply

Dan, Terrific adds. Great ones. Thank you.

Dan Black   |   13 February 2014   |  

Thank you:) Keep writing great content!

haiqal   |   19 October 2014   |   Reply

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.

Karin Hurt   |   20 October 2014   |   Reply

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.

Mike Ssempa Mulindwa   |   09 December 2014   |   Reply

Great ideas

Karin Hurt   |   09 December 2014   |   Reply

Thanks so much.

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Karin Hurt   |   09 April 2017   |   Reply

Thank you so much!

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Karin Hurt   |   07 June 2017   |   Reply

Thank you. You can always start with a free platform and write consistently and then migrate from there. The key is writing to add value for your targeted audience and fostering interaction.