The 10 Best Questions to Ask Your Mentors

10 Best Questions to Ask Your MentorsYou finally gathered up enough courage to ask a mentor, or potential mentor, for a cup of coffee. The pressure is mounting. You’re sweating, a lot; there aren’t enough Starbucks napkins in the world to dry your palms.

And just when you think you have enough time to hit the restroom again, she strolls up to your table holding an Americano with two pumps of hazelnut in one hand – and years of experience in the other.

That’s okay. You got this. Because you know the 10 best questions to ask a mentor:

How Do You Spend Most of Your Time?

Ask this question for one reason only — making a connection while showing you care. Does your mentor have children, a favorite charity she supports, or an addiction to a particular Mediterranean cuisine?

Most people who ask for advice never take the time to build an authentic connection. Gathering these answers will allow you to follow up with relevant articles, magazine clippings for passion projects, or even recipes for your mentor, who will appreciate hearing from you. Givers gain.

What Would You Do if You Were Me?

Don’t waste your time looking to impress your mentor with how smart you are. Tell them about your specific challenges, and ask for their recommendations. And then listen, and take action… in that order.

How Can I Help You?

This is a killer question that catches most mentors off guard. Most mentees are only concerned about what they can take, not give. When you communicate that you are genuinely willing to give, you will set yourself miles apart from everyone else.

Is This Where You Thought You Would End Up?

This question usually draws out a hearty laugh, as few people shoot from point A to point B exactly as planned. Most experienced professionals, in fact, take the scenic route to get where they are now in their career. How they got there is usually an interesting tale with mistakes and revelations. Learn from them.

What Used to Be Your Biggest Weaknesses?

This whopper will tell you right away if someone will make a good mentor. A good answer reveals the number one trait of a great mentor — self-awareness. Feel this question is too direct? Try softening it by asking, “What did you learn about yourself in the last six months?”

What Are You Most Proud Of?

Give your mentor a chance to shine. He/she will love you for it.

What Professional Organizations Are You Associated With?

No one becomes a rising star in any industry without going to the right conferences and trade associations. A good mentor can help you filter out the best ones, and if you’re lucky, get you access to coveted “invite only” insider groups.

Anything FORM

FORM is an acronym that represents the four universal rapport-builders: family, occupation, recreation and motivation. For example, you might find out that you have a location-based connection with your mentor after asking about his family or birthplace. Or that you interned for the same company or share a common goal. Connection made!

If a Specific Question Comes Up, Can I Follow Up with You?

Have you ever met someone who has mastered the dating scene? You’ll notice they never leave the first date without the promise of a second one — ever.

Never leave a mentor meeting without the promise of a future encounter. You are also communicating that respect their time and will only reach out with a relevant and specific question, which most mentors appreciate.

Who Else Would You Recommend I Connect With?

Save this question for later in meetings when more trust has been developed and the mentor has a better understanding of your goals. Delivered at the right time, it can exponentially expand your network; after all, sometimes the best source for other mentors is your existing one. Delivered too soon, and the person on the other side of the table will think you suffer from premature expectations.

What questions would you add to this list? Be sure to let us know, in the comments below!


For this post, YouTern thanks our friends at Startup Collective!


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Bert GervaisAbout the Author: Bert Gervais, aka “The Mentor Guy,” is one of America’s most in-demand professional speakers. He is an author, speaker and award-winning entrepreneur. Bert speaks on menteeship, mentorship and leadership and is the Amazon best-selling author of “Who’s In Your Top Hive? Your Guide to Finding Your Success Mentors.” Follow Bert on Facebook and Linkedin — and look out for the April 26, 2011 launch of his new blog “momentee” on tumblr!



The Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world’s most promising young entrepreneurs. In partnership with Citi, YEC recently launched StartupCollective, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses.


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