Questions You Should Always Ask a Potential Mentor

1. “What Do You Wish You Knew at My Stage?”

I always try to balance my mentor relationships between updating them on my goals and my background, and getting a strong sense of who they are and most importantly, who they were at my stage. What did they wish they knew? What obstacles did they not expect? How did they manage to get over them? These are all crucial for your development as an entrepreneur. – Rob Fulton, Exponential Black

2. “What Motivates You?”

You can get great technical advice, connections and encouragement from many sources, but understanding someone’s internal motivations will help you align your values before you begin a mentor relationship. – Kelly Azevedo, She’s Got Systems

3. “What Do You Expect From Me?”

Especially since formal entrepreneurial education is hard to come by, finding the right mentor can be an invaluable learning experience. Mentors tend to not only be knowledgable, but to have an understanding of how to best foster growth and uncover potential. If you trust your mentor, then ask what they feel you should be doing, and make doing that your goal. – Brian Honigman,

4. “What Has Been Difficult?”

Ask about failures instead of only focusing on how he or she has been successful. Find out which hurdle or setback was the hardest to overcome, and how it was dealt with. – Simon Casuto, eLearning Mind

5. “How Can I Make Your Life Easier?”

It’s true of managers and mentors, you have to manage up. The best mentoring relationships are a two-way street. If you’re seeking a mentor, the relationship should benefit you in some way, but don’t stop there. See if there is anything you can contribute that will make your mentor’s life easier. It can be as simple as determining a preferred method of communication, a skill, a connection, etc. – Sydney Owen Williams, 3Ring Media

6. “What Used to Be Your Biggest Weakness?”

If your potential mentor laughs and answers this question honestly, that’s a great sign that she or he is self-aware and willing to be honest with you — key qualities for a potential mentor. Also, if you can tell that your mentor has overcome those former weaknesses, that’s a sign of personal growth that fueled their entrepreneurship. – Dave Nevogt,

7. “What’s in It for You?”

I don’t believe in altruism — everyone has a self-interested motive, even if it is not apparently obvious either to you or to your potential mentor. I would be curious to know why they want to be your mentor and what truly motivates them. The sooner you get to the heart of the relationship and what motivates each of you, the sooner your relationship can grow. – Joseph DiTomaso, AllTheRooms

8. “What Should I Get Rid Of?”

To have hindsight is a blessing. It’s very important to learn the positives from mentors, but it is as important to learn about what you shouldn’t do. Think of every minute of the day as an investment. If mentors can teach you what you should ignore, outsource, etc., youwill be able to maximize your efficiency and productivity. – Adam Stillman, SparkReel

9. “What Do You Think Is the Biggest Mistake We Are Making Today?”

This gives great insight into how deeply a mentor has thought about your business. How well can they talk about the major parts of the business and how do they defend their argument? This question provides a lot of information about a mentor. – Randy Rayess, VenturePact

10. “What Are Your Guiding Principles?”

Every good mentor I’ve had has passed along a nugget of wisdom that has stuck with me and shaped me into the businessman I am today. – Eric Schaumburg,

11. “What Would You Do Differently?”

The relationship with a potential mentor is new, so solution-based questions can be more comfortable and respectful. The answer tells you if their feedback will help — the goal being to find a mentor that teaches and inspires you to think differently. It also allows you to see if they know about your business, your industry, your challenges and your opportunities. – Mona Patel, Motivate Design

12. “What Is Your One Major Success?”

A mentor should provide know-how and help you avoid repeating the same mistakes. In order to succeed, this type of focused advice is crucial. Perhaps you need to learn how to grow internationally, create a great team or perfect your business etiquette. You should always ensure your mentor is able to address the exact area you need to focus on in order to achieve maximum success. – David Tomas, Cyberclick

13. “How Can I Work Smarter?”

It’s a great sign when a mentor can answer this question well by condensing general tips on efficiency into a short conversation. Your mentor’s experience on specific sectors or wins will never be 100 percent identical to yours, but efficiency is a universal good that applies across all sectors of business. Plus, you gain insight into whether their work style and personality are similar to yours. – Jared Brown, Hubstaff


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