Questions to ask your mentor

Most mentors have years of experience. While it can seem difficult to discover ways you can harness that wisdom, asking them direct and open-ended questions is the best way to learn.

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Although it is usually thought of as a way to enhance an employee’s career path, mentoring can have benefits for the company too. Workplace mentorship is one of the most popular initiatives that an organization can take with regards to improving employee engagement and reducing turnover. Mentoring is also an important element to skill development and succession strategy. In fact, over 70 percent of Fortune 500 companies have workplace mentoring programs

However, to get the most out of a mentorship, mentees need to be clear, focused and may even need to encourage a mentor in their role. The easiest way to accomplish this is by asking questions. 

Tips on types of questions to ask 

Most mentors have years of experience. While it can seem difficult to discover ways you can harness that wisdom, asking them direct and open-ended questions is the best way to learn.  

Some of the questions that you can ask to get more from your mentorship include:

  • Why are you in this job/position/company? This helps you understand where your mentor is coming from and may also give you some insight into the reasons you will want to be in their position one day.

  • What advice do you have for career planning and advancement? This is the most obvious type of question for a mentor but you can also make it more specific by asking them what would you do if you were me? Getting a direct answer is usually the best thing. 

  • Does your mentor have a mentor? What was that experience like for them? Ask them what they learned. 

  • What is your biggest weakness? What have you learned about yourself over the past couple of years? These types of questions can help you discern whether your mentor has the gift of  which is an important quality in a leader and a mentor. 

  • When did you run into a situation that you did not handle well? Alternatively, you can ask ‘what is one thing you would have done differently?’ This helps you see not only that everyone makes mistakes but also gives you a chance to learn from them. When your mentor reflects on what they may have done wrong and how they would have handled the situation differently it can add to your wisdom in case you face a similar situation.

  • What factors do you weigh when thinking about your future? The answer to this question can help you develop your own system of future planning.

  • How do you balance work and life? Mentors have usually been in the workforce longer and have had time to build up skills that newer employees don't have yet. This can include finding a work-life balance. Ask your mentor How they balance their work and private lives. How do they avoid conflict in these areas and enjoy them both?

  • Do you know anyone else that I could connect with? Networking is one of the top benefits for mentees. Mentors who have been in the industry for a while often have access to another top talent you can learn from. However, this may be a question best left for a later meeting. Once you and your mentor have gotten to know each other a little they will be in a better position to answer this one. 

  • Are there any professional organizations or groups I should be a part of? Similar to the networking question, this one is designed to expand your network. Your mentor may be able to direct you to organizations that will help you grow your skills and connect you with others in the industry. 

  • Is there a question you wish you had asked earlier? Essentially, you don’t know what it is that you don’t know. However, your mentor has insight into the industry and company that you don’t. The answer to this question can help you see things you may have missed or overlooked. 

Asking good questions is essential to building a successful mentoring relationship. If you're looking for event more questions to ask your mentor here are 29 more questions to ask your mentor in your next meeting.

Tips for great mentoring sessions

Before you head into any meeting with your mentor, get prepared. Mentors are usually quite busy people so make the most of the time they offer you. Have a goal for your meeting. What issue are you looking to discuss? Write down a list of questions related to this issue. This helps you get the most from your mentor’s time and also allows you to focus.

In addition to asking for their advice, take the time to get to know your mentor as a person. What do they like to do with their spare time? Look for some ways that you can help them. Mentor relationships do not have to be one-sided. 

Serial entrepreneur Neal Taparia, who runs FreeCell Challenge, explains,

“I’ve often benefited from those I mentor through introductions to prospective employees, or new ideas on what games to develop or new technologies to try. It further enriched my relationship with mentees.”

After the meeting, reflect on what you learned. Write down any additional questions that have come up as a result of the discussion. 

Send a thank you message to your mentor so they can see you appreciate their time and advice. 

Sometimes the answers to these questions will unveil problems with your mentor. If you feel your mentor might not be the best match for you it is okay to get in touch with the manager of your workplace mentoring program to request changing your mentor


The old adage is true that you only get out what you put in, even when it comes to mentoring. The more effort you put in to get to know your mentor, to learn as much as you can and to show your appreciation the more you will connect with your mentor, learn and earn respect. One of the best ways to do this is by asking questions, particularly the right ones. 

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