9 Questions Every Mentor Should Ask Entrepreneurs (If They Don’t, Ask Yourself)


Guest author Scott Gerber is the founder of the Young Entrepreneur Council.

In a mentorship relationships, questions are usually more important than answers. After all, how can you help prepare someone if you don’t know exactly what they want to accomplish?

That said, not all mentors are created equal, which is why we polled nine entrepreneurs from Young Entrepreneur Council (YEC) regarding what they wish their mentors would have asked when they first approached them. Their answers are below.

Are You Ready?

I wasn’t ready at the time for the journey ahead; physically and most importantly, mentally. He could have guided me a little differently and helped me in ways that took him years to realize.

Two years after I met my mentor he asked me this and really started helping me become ready for the journey I’m on right now. To become the best mentor, you have to really know everything about the person. Know how they work and how you can best help them to become the person they are meant to be.

John Rampton, Host

Why Do You Want This?

My mentor has been invaluable for my career thus far and has generously given me lots of great advice, but one question I wish he’d have asked was why I wanted to achieve the goals I had set for myself. He encouraged me to pursue my own venture, but never really asked me why I had made that choice.

Through a good amount of soul-searching I feel that I was able to come to this answer on my own. However, having an understanding of my motivations before I embarked on this journey would have curbed a lot of my initial anxiety and might have led me to make better decisions.

Also, having that conversation might have prompted him to share the reasons why he pursued entrepreneurship. Maybe the reason he never brought it up was because he felt I needed to reach those conclusions on my own.

Brian Honigman, BrianHonigman.com

How Much Time Are You Ready to Devote to This Relationship?

Setting expectations for any relationship is a good idea. Mentors are often strapped for time more than others, and now I ask potential mentors what amount of time they are willing to give, as well as what amount of time they expect from me. Are we going to give each other an hour a quarter with brief updates or can I expect us to meet on the weekend for five hours once a month to review some critical planning? Big difference.

Beck Bamberger, BAM Communications

Are You in It for the Long Haul?

Fast forward 10, 15, 20 years after starting the business. Are you going to be content to still be driving the company? I think building something for the long haul that’s sustainable is much more rewarding than trying to do a quick short-term flip. I’ve been running my business for over 12 years and I’m still loving it every single day.

Luke Skurman, Niche.com

What Are You Most Passionate About?

It’s essential that you are not in your professional sector for the wrong reasons, otherwise you will end up unhappy. That being said, I wish that my mentor had initially asked me: “What are you really passionate about and what do you find easiest to master?”

Passion and ease tend to be connected. This is not always because your passion comes naturally, but because you have spent hours upon hours doing research and self-teaching on the subject. As soon as you can answer this double-edged sword of a question, you will begin to find other questions about the future and your vision will not be as scary and impossible to answer.

Ranan Lachman, Pley

What Wakes You Up in the Morning?

For some, waking up and feeling motivated to do anything other than rest can be a struggle. If my mentor had asked me what got me going in the morning, what fueled my passion to pursue my long-term goals or what motivated me to do what I did every day, I would have been able to disclose my yearning to break free from a traditional career and work environment. By revealing my true inclinations, I would have developed the courage to become an entrepreneur sooner rather than later.

Firas Kittaneh, Amerisleep

What Can You Do That Will Most Impact Your Business Today?

I think many times early on we get so caught up in operations that we lose sight of the big picture and what matters most to our business. Mentors help you reassess some of the core assumptions that you make by asking smart questions like, “what will most impact your business?” This gives you a sense of how to prioritize the long list of tasks that you are constantly struggling to complete.

Randy Rayess, VenturePact

How Big Should This Company Be?

It is important to have a realistic view of the industry your company is in. Not every company is Uber, which is solving a fairly ubiquitous problem. If you are creating a company of a niche industry, it will limit your size. This isn’t an inherent issue, but you must make sure to fundraise and scale appropriately.

Adam Stillman, SparkReel

What’s Preventing You from Accomplishing Your Goals?

This question forces you to dig deep and get past the excuses. The follow-up question is “why?” It forces you to dig into specific reasons why you failed or made mistakes. This level of introspection allows you to learn from those mistakes and gives you a higher probability for reaching your current goals. I hire a mentor for two main reasons: clarity and accountability.

Joshua Lee, Standout Authority

Lead image courtesy of Shutterstock

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