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What are the most valuable questions to ask a mentor about career path? First off, congratulations on finding a mentor. Mentorship is a scarce resource that not all have access to.

That means when you find a mentor, you have to ask engaging questions. After all, the mentor-mentee relationship is just that: a relationship. Every question you ask, ideally, creates value on both sides. Otherwise, it becomes a one-sided relationship quickly. That’s one of the biggest mistakes entrepreneurs with make mentors and advisors.

So how do you ask engaging questions? On the surface, it may not seem like any questions to ask a mentor about career path will land as mutually beneficial. But like in every relationship, there’s psychology on both sides. Understand that, and you’ll craft highly personal questions (e.g., “What skills should I master to reach the C-suite?”) that also make your mentor feel fulfilled.

Need help getting started? We asked 12 entrepreneurs for good questions to ask a mentor. Their recommendations are based on years of investing in their own career and leadership growth. Use them verbatim, or as inspiration to think up new questions to ask your mentor.

12 of the Most Powerful Questions to Ask a Mentor About Career Path

1. How Would You Like Me to Follow Up?

“A lot of mentors want to know they made a difference. They want to know what you did as a result of the conversation you had with them—even if you didn’t take the mentors’ best advice. They want to know that their time was well-spent and they are making a difference.”

Reid Carr, Red Door Interactive

2. Why Do You Do What You Do?

“Ask your mentor why he or she does what they do. Successful people often have very strong reasons for why they do what they do. If you can identify why you want to do something, the ‘what to do’ and ‘how to get there’ will often come much more naturally.”

Kristopher Jones, ReferLocal.com

3. What Mistakes Have You Made?

“Everyone makes mistakes. The mentor who willingly owns up to these mistakes and helps you to avoid making the same ones is a valuable resource and ally. The openness to share mistakes is a good sign that your mentor is candid, will look out for your best interests, and is invested in your future success.”

David Ehrenberg, Early Growth Financial Services

4. What Factors Do You Consider Most Often When Planning for the Future?

“This can be situated as a short- or long-term question, but it gives you the opportunity to discuss everything from his core beliefs to problems that need solving to what to learn. While your mentor isn’t a fortune teller, this discussion serves as a catalyst for many ways for you to develop.”

Emily Eldridge Holdman, Adventur.es

5. How Do You Spend Your Time?

“Time is, in a way, the most precious commodity. Understanding how to make the most effective use of time is crucial. Often, the most successful people have figured this out, and it’s worth asking them where they spend their time and how they feel it benefits them.”

Divya Dhar, Seratis (acquired by HudlHealth)

6. What One Thing Do You Still Struggle With?

“What is the one mistake, habit, or pattern that you still haven’t overcome after years of business?”

Parker Powers, Blackwell SGP

7. What’s One Thing You Would’ve Done Differently?

“I think most people say, ‘I have no regrets,’ but really, there are things they would certainly do differently if they had a time machine. I like hearing what my mentors wish they did differently and what mistakes held them back so that I can learn from those.”

Natalie MacNeil, She Takes on the World

8. What Do You Mean?

“Mentors usually don’t want to be revered; they want to help. So, pretending you know everything they’re talking about is a big mistake. Often, you genuinely don’t, so don’t be afraid to ask. They’ll respect you more, and, of course, you’ll probably learn something, too.”

Derek Flanzraich, Greatist

9. What Are You Trying to Accomplish This Quarter?

“This question invites a wealth of short-term and long-term opportunities for you to learn and do a few things. It helps you understand how your mentor tends to problem solve, enables your mentor to see you in a new light as a resource to help, and gives you a chance to deepen your experience in an industry of interest. Consider any questions to ask a mentor about career path a two-way street of opportunity.”

Mary Ray, MyHealthTeams

10. What Would You Do if You Were Me?

“The biggest question to ask a career mentor is what they think you should do. Explain what position you are in, and leave out all the fluff about how awesome you are. Make sure they have a true understanding of your business and look them dead in the eyes with open ears. If they think you’re serious and actually looking to act on their advice, they will usually give you the best advice.”

Robert De Los Santos, Sky High Party Rentals

11. What’s One Question You Wish You Asked Earlier?

“Peak Performance coach Tony Robbins once told me that the difference between success and failure is much smaller than most people think. The key is to uncover the subtle distinctions that separate those who have from those who don’t. So, I’d ask the question, ‘What’s one question you wish you asked someone but didn’t?’ This may help expose what your mentor felt was most important to him or her.”

Charles Gaudet, Predictable Profits

12. What Can I Do Better?

“Too often, people rely on their mentors for specific situations or how to handle a particular issue. Mentors are there to help guide you as a person and help you grow bigger and better than you currently are. Ask the hard questions such as, ‘How can I improve?’ or ‘What do I do now that I can and should do better?’ Use them to guide you all the time—not simply when an issue arises.”

– Aron Schoenfeld, Do It In Person LLC

Editor’s note: This is an updated version of a blog originally published on April 16, 2014. 


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