Invite a Mentor for Coffee and Ask These 10 Questions

Here are ten questions you can ask her to take the pressure off and make the most of your meeting.

Congratulations! You finally mustered the nerve to ask a mentor out for a cup of coffee. When you arrive you realize that you are sweating. You can feel the pressure mounting. Then she strolls through the coffee shop holding an Americano with two pumps of hazelnut in one hand and years of experience in the other. Here are ten questions you can ask her to take the pressure off and make the most of your meeting:


  1. How do you spend most of your time?

    Ask this question for one reason only — to build a closer connection. 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. These types of conversations will allow you to follow up with relevant articles, magazine clippings for passion projects, or recipes for your mentor, who will appreciate hearing from you. Remember: givers gain.

  2. What would you do if you were me?

    Don’t waste your time looking to impress your mentor with how smart you are and what you’ve accomplished. Tell them about your specific business challenges, and ask for their recommendations.

  3. How can I help you?

    This is a game changer question that catches most mentors off guard. Most mentees are only concerned about what they can take from a mentor. When you communicate that you are genuinely willing to give, you will set yourself miles apart from everyone else. Who doesn’t like a win/win relationship?

  4. Did you think you’d end up here?

    This question usually draws out a hearty laugh, as few people shoot from point A to point B. Most experienced and successful people take the scenic route in their professional lives. How they got there is usually an interesting tale with many small business mistakes and revelations. Learn from them.

  5. What used to be your biggest weakness?

    This whopper of a question 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. If you feel this question is too intense, try softening it by asking, “What did you learn about yourself in the last six months?”

  6. Who else would you recommend I connect with?

    This question might be better served for later meetings when there is more trust. It can exponentially expand your network. Sometimes the best source for other mentors is your existing one.

  7. What are you most proud of?

    Give your mentor a chance to shine. She will love you for it.

  8. What professional organizations are you associated with and in what ways?

    No one becomes a rising star in any industry without speaking at, or attending, 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.

  9. Ask the anything ‘FORM’.

    Form is an acronym for family, occupation, recreation and motivation, and it represents four universal rapport-builders. For example, you might find out that you have a location-based connection with your mentor after asking about his family or birthplace. Connection made!

  10. If a specific question comes up, can I follow up with you?

    This is your Holy Grail question. 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 you will only reach out with a relevant and specific question. Most people will agree to that. When the time does come up, simply refer back to the email chain.

This article has been edited and condensed.

Bert Gervais, a.k.a. “The Mentor Guy”, is the founder of Success Mentor Education. He is a national best selling author, speaker, and award-winning entrepreneur. Connect with @BertGervais on Twitter.


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