Guest Post by Karin Hurt

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!

The “8 Questions You Should Ask Your Boss” will 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? How can I be more effective in that arena?
  7. Which parts of my style concern you the most?
  8. 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 “Let’s Grow Leaders” 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… e.g. 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?

Your turn. What questions should you ask your boss? What would you add to this list?



Karin Hurt is an Experienced executive and leadership zealot with a diverse background of executive leadership experience in sales, customer service, human resources, merger integration, training and leadership development.  Her favorite work is to ask questions and inspire others to look deeply within themselves as they grow as leaders.  You can connect with Karin on her blog:  Lets Grow Leaders

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