The One Question You Should Ask Your Small Business Mentor

Having a mentor is like having an EZ-pass on the road to retail success. Your company may be able to avoid many of the typical road bumps faced by startups by having an invaluable champion and advisor. From making introductions to advising on pricing strategies, mentors can offer a quick and insightful response.

[Related: 5 Things to Consider When Securing a Mentor]

The best way to find a mentor for your small business or startup is to access your alumni network or reach out to industry experts at conferences. What one question should you always ask a potential mentor? This is the question posed to members of the Young Entrepreneur Council (YEC), an invite-only organization comprised of the world’s most promising young entrepreneurs. In partnership with Citi, YEC recently launched BusinessCollective, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses.

Here are their top inquiries for a mentor:

“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, AudioLumin

“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

“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

“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 Williams, Planet Green Socks

“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,

“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

“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,

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