Questions to Ask a Mentor: 20 Examples

Sam Cook
Question mark in a tunnel for mentor questions.

Finding the right type of mentor can catapult your career, but you also need to ask the right questions. The best questions to ask your mentor are those that help you better understand yourself and extract the best insights from your mentor. Because mentoring relationships are mentee-driven, effective mentees should have a list of questions to ask a mentor that drives the conversation and get results.

If that makes you a bit nervous, we get why. There are good questions for mentors, and there are questions that don’t get any results at all. Not everyone is good at probing their mentor for answers. The following 20 questions should give you a good starting point for improving communication with your mentor and achieving your mentoring goals.

20 Questions to Ask Your Mentor

Mentorship relationships work when mentees ask the right questions for their professional development and career path. However, it is easy to get caught in the moment and be in awe of the brilliance of your mentor. To help you stay on track, here are some of the best questions you can ask your mentor.

Some of the following questions may be open-ended, but you can tailor them to align with your specific interests and goals.

Questions on mentorship itself

1. Why did you want to become a mentor?

2. What do you want to get out of this mentor relationship?

3. How often do you want to meet?

4. How do you want to communicate?

5. How can I come more ready for our scheduled meetings?

Questions on personal experience

6. Where do you find your inspiration?

7. What values do you find most important in a person? How do you commit to these values?

8. What are your strong and weak traits?

9. How do you get a better work-life balance?

10. What are your interests, hobbies, and/or things you do outside business hours? How did you get interested in those things?

Questions on professional experience

11. What are the biggest challenges and most important lessons you learned in your career?

12. What life skills have been most beneficial in your career?

13. What are the things I need to learn and develop to help me advance in my career?

14. What is one lesson you can teach your younger self?

15. What gives your job meaning?

Questions on your personal and professional growth and career development

16. What are the most important skills you think I need to work on?

17. What areas in my career do you think I need improvements on?

18. Did you have professional development courses? What do you recommend I should get?

19. What do you think is popular entrepreneurial advice most people don’t understand?

20. How can I stay positive in my current position, career, and chosen field?

Bonus: Questions on career transition

Things may not always go your way, and there are times when you need to change careers or transition in a new direction within your current one. When working with a mentor, there is a good chance your mentor went through similar dilemmas. Don’t be afraid to ask about how they overcame those challenges.

21. How do you know it is time to change careers? What are the first steps you need to take?

22. How do you find meaning and purpose in your career?

23. How do you find a job that fits your interest and passion?

24. How can I be more proactive in carving my own career path and future?

25. Will changing my career hurt my professional reputation?

Why You Need to Find a Good Mentor

These questions to ask a mentor will come in handy, but that’s only if you have a mentor at all. Finding a good mentor is often not easy, but it’s important.

Here’s an unpopular opinion — there is no such thing as being self-made. As the great American columnist George Matthew Adams once said:

Questions to ask a mentor in a group working together.

You are made up of thousands of others. Everyone who has ever done a kind deed for us, or spoken one word of encouragement to us, has entered into the makeup of our character and of our thoughts, as well as our success.”

Indeed, you are the by-product of your environment. Yes, you have to work hard, be smart, and be persistent to achieve your goals. But you also have to network and introduce yourself to the right people and make the right connections.

A huge part of your success is the result of contributions from your immediate circle, be it your family, friends, and of course, mentors. Whether you are looking to join the Olympic wrestling team, or become a world-renowned author, chef, startup CEO, or restauranteur, you will need the help of others. Everything in life is a team sport.

But like most things in life, finding the right mentor requires forethought, hard work, and in the workplace, a lift from matching tools that can help you find a mentor that matches your personality, interests, and needs. You have to find someone you look up to and want to be like. Then, you have to work with that person, commit to the mentorship relationship, evaluate your progress, and trust the process.

Moreover, to get the most out of your mentoring relationship, you need to know how, what, and when to ask the right questions.

First Steps to Prepare for Meeting a Mentor

The first step in the process is to find a good mentor. There are several ways to do that. There are two real ways to do this:

  • Asking someone who’s succeeded in areas you want to grow in to be your mentor
  • Joining a workplace mentoring program

The first of these might be a bit hard to do if you don’t know anyone who fits that criteria or you’re shy and unsure of how to approach that individual. A possible solution to that is to join a group mentoring program instead of a 1:1 mentoring program. That way, you can still get mentoring from someone who has the experience you need, but under much less pressure.

Other types of workplace mentoring programs are ideal, as well. Typically, you’ll get matched into the program by the program administrator. When mentoring software is involved, that process includes filling out a personality and interest survey that will match you up with someone using modern matching algorithms that are proven to produce higher-quality matches.

Once you have found someone who you believe may be a good fit for you, it is time to prepare for your meetings. It doesn’t matter whether it is your first or subsequent encounters; you need to establish your goals ahead of your meetings, seek consistent and continuous engagement, and hold yourself accountable.

1. Establish your career objectives

Mentors are often leaders in their field. In the corporate world, they usually hold executive and managerial positions. They manage different people and deal with multiple various tasks in a day. Executives even mentor each other, so you’re not alone in seeking a mentor among the company leadership.

Computer with notes to prepare to ask questions of mentor.

Because their time is limited, do the following before you go into your mentor meeting with a handful of questions:

  • Consider what you need out of the mentoring relationship
  • Write down important questions related to that goal
  • Identify possible milestones to achieving that goal
  • Outline how a mentoring relationship will help you through the process.

Are you looking for career guidance in your current position and role in your company? Do you want to climb higher on the corporate ladder and want your mentor to show you the way? What aspects and qualities of your mentor’s leadership and expertise do you want to achieve for yourself?

The idea is to learn as much as possible from your mentor and to develop certain expertise and skill. That way, once the time comes, you can step easily and confidently into the roles you want for yourself in the future.

Whatever it is you are looking for in a mentoring relationship, you need to establish your short-term and long-term goals to determine exactly what you want to achieve from your time together with your mentor.

2. Seek engagement opportunities

You need your mentors more than they need you, thus, it is your responsibility to seek consistent and continuous engagement and drive the relationship forward.

Take care of all of these engagement needs:

  • Schedule meetings that meet their schedule and organize the agenda for each meeting
  • Determine a good meeting cadence
  • Decide on a meeting length that works for both you and your mentor
  • Commit to your meeting schedule

Also, it is important to ask your mentor for his/her preferred communication method. Obviously, you cannot email or text your mentor over the weekend, holidays, or late at night, unless they specifically told you that you can.

3. Hold yourself accountable

Take notes (if not mental notes) after each meeting; write down everything there is to learn in. Use AI note-taking software if your mentor will allow you to, or learn a shorthand note-taking method.

Also, many times your mentor will give you assignments or engage you in mentoring activities and tasks to accomplish in between meetings. This is often the case with structured mentoring programs, such as onboarding mentoring or functional mentoring. Make sure to complete these assignments and be prepared to present them to your mentor in your next meeting.

Did you know: Accountability means taking the time to measure whether your mentoring is successful? Take a moment to watch this Mentoring Soundbites video with your mentor so you both know how to measure success.

There will be times when you cannot complete the tasks or commitments. If that’s the case, tell your mentor in advance so they won’t waste their time waiting for you.

How to Ask Your Mentor Questions

The best way to get answers and career advice is to ask the right questions, and for you to do that, you need to know how to formulate a good question in the first place. Here are some tips on how to make the right questions to ask a mentor.

1. Make your questions specific, not vague

Keep the questions clear and relevant to your current topic and specific to the situation or lesson. People seek guidance from their mentors to solve specific problems in their professional careers. Mentors love that, as it gives them a chance to share their experience, specifically on how they handled and solved challenges in the past. It’s why mentoring tends to increase job satisfaction for both mentors and mentees alike.

Say you have a mentor to address your fear of public speaking. Here are a couple of questions you might ask:

  • “How can I develop my public speaking skills?
  • “How do you manage you handle nerves when speaking in public?”

While the first question may be relevant to your goal, it is a vague question that may require a much longer long conversation to answer. The second question, on the other hand, is more direct and to the point. It allows the mentor to answer quickly and completely, without spending hours trying to explain everything.

Your mentor may share tips on how they psyche themselves up to face a huge crowd and how they prepare their speech or presentation.

2. Focus on topics that aid in career advancement

Know how to ask questions that lead to meaningful conversations.

Here are a few examples:

  • Should you want to learn more about your mentor’s expertise then, ask for specific advice on how they developed and continue to refine their skills.
  • Ask them to share stories about how they networked with industry leaders and leaders within your company to advance their career.
  • For people looking to build a startup, you can ask your mentor how they took huge risks and how things panned out. This question gives a really good insight into how they manage risks, foresee challenges, and solve those obstacles.
  • Ask questions specific to the situation.
  • Don’t be afraid to ask for clarifications and circle back to your conversation to make sure you understand and follow your mentor’s advice.
  • Have a sense of accountability as a mentee. Ask your mentor how you can improve as a mentee and make your mentorship work for both of you.
  • If you are starting a business, then you need to ask your mentor how to become a better leader. This involves knowing how to handle multiple people with different personalities and egos and resolve conflicts within your team. Moreover, ask your mentor on how to handle different aspects of your business better, and the habits needed to build to become a successful entrepreneur.

3. Seek meaningful advice, but connect with small talk

Keep the conversation meaningful, but don’t avoid small talk. Making connections with your mentor is important. Multiple studies show that small talk builds rapport and will lead into larger and more important conversations. It’s also a healthy and effective way to establish and sustain relationships at the surface level that then move into deeper engagements.

4. Always come prepared

As said earlier, your mentor’s time is extremely valuable. Thus, respect their time by coming in prepared. Also, this is the best way to get the most out of your mentoring program. Ready your questions and listen intently so you can make your follow-up questions.

5. Use questions as a conversation starter

Identify the different ways you can build your career by asking questions that lead to actionable advice. Seek networking advice, ask how you can improve your leadership qualities, speaking, and presentation skills, etc.

The Bottom Line: Ask Your Mentor Questions, Then Take Action

If you want to be successful in whatever you choose to do, you need to connect with the right people. People who can guide you through the intricacies of your chosen field, the ins-and-outs of your chosen career, and help you develop and grow to be a better version of yourself.

This is what a mentorship program is about. It helps you carve your career paths, develop the key skills you need, find the meaningful answers to your most important questions, and ultimately, achieve success.

Once you’ve landed a great mentoring relationship, started meeting, and begun asking the hard questions, don’t forget to take everything to heart and take action. After all, there’s no point in spending time with a mentor if you don’t plan to be actionable.

Sam Cook