Questions You Should Ask Your Mentor

Mentors can be a major influence on not only your career, but also your life. Think about people who have had a great effect on your life (hopefully in a positive aspect). These people can come in a variety of different roles: parent, coach, teacher, boss, etc. Regardless of where and whom you draw inspiration from (if you haven’t found someone yet check out these tips!), these people can be considered mentors.

If you have a mentor, hopefully you have taken the opportunity to pick their brain for career or life advice. After a few meetings, it may seem that the conversations have gone rather stale and possibly even repetitive. Need some conversation points for you next meeting? In an article for Forbes, Jo Miller breaks down four different types of questions to ask your mentor. You can read the full article here.


The great thing about mentors is that they were once in your shoes, after all the very definition of a mentor is “an experienced and trusted adviser.” If you are unsure of your career progression or an aspect of your job, ask your mentor about a similar time in his or her career. Some questions you can ask, according to Miller are:

  • Was there a time you messed up and felt like you’d failed? How did you bounce back?
  • Which leadership skills were the most difficult to develop?
  • Think back to five years ago. Did you envision your career as it is today?

If you are unsure of where your career is heading, these questions are great conversation starters with your mentor. He or she might have had a similar feeling when they were in your position, so hearing how they handled the situation can benefit your career and life in general.


Situational questions are when you can start getting more specific in your conversation. Is there a specific component of your career that you need help navigating? Maybe you are in a position that you aren’t sure how to handle, so this is a time when you can ask your mentor. Some of these questions are:

  • My boss said I need to be more strategic. What does that mean?
  • I have two very different career path options available to me. Can you weigh in to help me make a final decision?
  • I’m considering a career transition. What are some other areas of the business that might be a good fit for me?

These are great questions when you are stressed out at work and unsure of how to deal with it. Although it might not be the exact same situation as you, chances are your mentor has endured something similar so can impart some wisdom.


According to Miller, “one of the greatest gifts you can give yourself is the gift of self-awareness, meaning the ability to see yourself as others view you.” By understanding what your colleagues think of you, whether positive or negative, you can either continue doing what you’re doing or figure out how to rectify your image. Some questions are:

  • How am I viewed? In other words, what’s my personal brand in our organization?
  • Where do you see my strengths?
  • Do I come across as strategic or tactical in my day-to-day communication?

Sometimes it helps having another set of eyes or opinions when it comes to assessing your presence within the organization. Your mentor is someone you respect and will provide constructive criticism, so although it might not be exactly what you want to hear, it is better to hear it from someone you trust. After all, your mentor is there to provide guidance and help you improve as a professional.


Let’s face it. Sometimes we all doubt our abilities. While it is easy to sit around and wallow in self-pity that others might be more skilled at something, it is better to realize that you have areas of improvement and take action. If you are unsure about how to improve upon certain areas of your job, these are some good questions to ask your mentor:

  • Can you recommend a book or resource for dealing with difficult conversations?
  • What practices can you recommend for dealing with nervousness when speaking to groups?
  • What new skills do I need to move ahead?

There are a variety of resources available to continue educating yourself, including, but not limited to: HubSpot and Lynda. Beyond those, your mentor might have some books to consider reading or people to introduce you to.

With these types of questions, your next meeting with your mentor will be more beneficial. To read all 40 questions that Jo Miller provides, read her full article here.

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