The Top 10 Questions to Ask Your Startup Mentor



So you finally mustered the nerve to ask a mentor for a cup of coffee. You’re sweating. You can feel pressure mounting. She strolls through the Starbucks door holding an Americano with two pumps of hazelnut in one hand and years of experience in the other.

Here are 10 questions you can ask her to take the pressure off you and make the most of your meeting:

  1. How do you spend most of your time? Ask this question for one reason only — digging. 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 recipes for your mentor, who will appreciate hearing from you. 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. Tell them about your specific challenges, and ask for their recommendations.
  3. 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 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. 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. Most experienced professionals take the scenic route in their career. How they got there is usually an interesting tale with mistakes and revelations. Learn from them.
  5. What used to be your biggest weaknesses? 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. He/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 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.
  9. 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.


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.

Image Credit: CC by Gvahim

About the author: Bert Gervais

Bert Gervais, a.k.a. “The Mentor Guy”, is the founder of Success Mentor Education. He is a national bestselling author, speaker, and award-winning entrepreneur.

  • PeterJ42

    Most of these were quite clever and unambiguously put across.
    But one is a question I would ask, but for a different reason.

    When knowledge was expensive and rare, professional organisations were a valuable way to form a community of experts and to share the high cost of journals, learning experiences etc.

    But over time, they evolved into something else – a badge to say “I have passed the entry standards for this group”. That sounds sensible too – you wouldn’t want a plumber who hadn’t passed his exams or a doctor who hadn’t got his degree.

    But the good people don’t need the qualification. They have proof of their capability – the projects they’ve done, the people who recommend them etc.

    The people who have to wrap themselves in this cloak of respectability are the ones who aren’t so good at their job. You’ll find them in every professional association or trade guild – they are often the ones who embrace the medals, gowns and trappings of office, they are the ones who have the letters after their name on their business car, they are the ones who turn up to every meeting.

    Now you don’t want these people as mentors. They will mire you in “this is how it has always been done” or this is “best practice” or “this is what the institute recommends”. Any disruptive ideas will be squashed and you will be cajoled to run your startup like a major corporation with procedures for this, governance for that.

    But they wrap themselves in the jargon of the day. They talk about innovation. Throw words like Lean, Agile or Iterative into the mix. Only when you dig deeper it becomes apparent that this are just words they picked up from the association newsletter – one I uncovered thought Lean and Lean Startup are the same thing.

    So ask the question. It tells you a wealth about the person. Run a mile from the ones who wrap themselves in the association as if it were a badge of proof.

    In the modern, connected world, the good people rise to the top without associations. They are obvious. Seek them out and leave the association pushers behind.

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