8 Questions You Must Ask a Potential Mentor

Mentor word cloud written on a chalkboard

Your networking has led you to an influencer… an expert in your field… a potential mentor.

You invite her to coffee, hoping to start a mutually-beneficial relationship. You know there’s a lot to learn from her… but where do you start?

To help you launch the conversation in the best way possible — with an amazing ice-breaker question — we asked established young entrepreneurs this question:

What one question should you ALWAYS ask a potential mentor?

Here are some of their best answers…


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

Rob-Fulton“I 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 FultonAudioLumin


“How Can I Make Your Life Easier?”

Sydney-Williams“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 WilliamsPlanet Green Socks


“What Used to Be Your Biggest Weakness?”

Dave-Nevogt“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 NevogtHubstaff.com


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

Randy-Rayess“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 not only provides a lot of information about where your biggest obstacle may lie, it tells you a lot about the mentor”

Randy RayessVenturePact


“What Would You Do Differently?”

Mona-Patel“The relationship with a potential mentor is new, so solution-based questions can be more comfortable. 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, industry, challenges and opportunities.”

Mona PatelMotivate Design


“What Is Your One Major Success?”

David_Tomas“In order to succeed, success focused advice is crucial. Perhaps you need to learn how to grow professionally, create a great team or perfect your business etiquette. Or maybe build your own business. 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 TomasCyberclick


“How Can I Work Smarter?”

Jared Brown“It’s a great sign when a mentor can answer this question 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 their work style and personality.”

Jared Brown Hubstaff


“What Has Been Difficult?”

Simon-Casuto“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



For this post, YouTern would like to thank our friends at Business Collective!


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