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12 Questions You Should Ask Your Mentor ASAP

Don't waste your mentor's time--or yours. Get better advice by asking the right questions.
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Every entrepreneur can benefit from the advice of a mentor (or two), especially one who has seen some success already and can offer needed perspective. The problem is, we often waste their time--and our own--with meaningless questions that don't get to the heart of the issues we face. So we asked 12 young founders from YEC to share the top questions they ask their mentors when they're looking for advice that sticks. Their best answers are below.

1. "What do you wish you knew at my stage?"

I love to ask mentors what they wish they knew when they were at my stage of life and business. It's eye-opening to hear about the experiences they had and the recommendations they'd make so that I don't make the same missteps.
- Darrah Brustein, Network Under 40 / Finance Whiz Kids

2. "Who else would you recommend I connect with?"

Making the most of your mentorship is extremely important, and expanding your network is as well. So when you have time with your mentor, ask them who else you should contact to help you with your beginning experiences. Most likely they'll refer you to one or two people--but that's more than you had before, and they'll appreciate you taking initiative in asking.
- Rob Fulton, Automation Heroes

3. "How can I work smarter?"

Your mentor is there to help you improve your overall business and well-being. If they can help you learn how to work smarter and not always harder this will help you from both a productivity standard and increase your potential to be successful. At the same time this will allow you to enjoy your friends and family more and realize the fruits of your labor.
- Jason Grill, JGrill Media | Sock 101

4. "If you could do it all again, what would you do differently?"

You want to put yourself in your mentor's shoes and your mentor into yours. This will open lines for sharing a number of relevant stories and give you an opportunity to learn valuable lessons from their experiences.
- Ashley Mady, Brandberry

5. "What are you trying to accomplish this quarter?"

This question invites a wealth of short-term and long-term opportunities for you to learn and do a few things. It helps you understand how your mentor tends to problem solve, enables your mentor to see you in a new light as a resource to help, and gives you a chance to deepen your experience in an industry of interest.
- Mary Ray, MyHealthTeams

6. "What would you do if you were me?"

Try to get the mentor in your shoes and see where it leads. They'll see the business in a completely different light and they'll be able to lead you places that you didn't even think about. The majority of this will be about focus (and where you should focus your time), but also about customer segments that you may not have considered or a different way to sell your product.
- Dave Nevogt, Hubstaff.com

7. "Am I being crazy?"

Entrepreneurs tend to get stuck in their own bubbles full of problems, obstacles, and ideas. Sometimes when coming up for air you need to ask a trusted mentor if you are in fact being crazy or irrational. Whether it is a situation or an idea, a fresh pair of eyes that are not connected to the situation directly will tell you whether you on the right path or if you are headed off course.
- Kim Kaupe, ZinePak

8. "What should keep me up at night?"

This is one of the best questions an entrepreneur can ask. It's an effective way of saying, "What's the thing that worries you most about my business?", but does so in a way that leaves the mentor feeling open to giving you genuine feedback. There's nothing more valuable than hearing the one thing a mentor believes can sink your company. Give them the right space to honestly answer the question.
- Mitch Gordon, Go Overseas

9. "What were your biggest failures?"

So many times people like asking their mentors what has made them successful. I have found that by asking your mentor what mistakes they have made or what have they learned from their failures is a better gauge on their success. You get a more real answer and can have a honest and open conversation with your mentor.
- Alex Chamberlain, EZFingerPrints

10. "How would you handle this scenario?"

Mentors are very busy. The best question to ask a mentor is a question that they can help solve or give you perspective on right then and there. You don't want to give them a task or a question that they won't be able to solve on the spot. In general, the best approach is to ask them, "How would you handle this scenario?" and then lay out the issues and why it's troubling you.
- Luke Skurman, Niche.com

11. "What has been your most rewarding accomplishment?"

Find out what successes were the most meaningful to them. You can glean sage advice from learning what's important to your mentor on a personal level.
- Daniel Wesley, DebtConsolidation.com

12. "What am I doing wrong?"

Then listen without being defensive. Many times when meeting with my mentor I would try to justify why I was doing something, when I should have just been listening. I found the above question, along with asking how I could do it better, was a great way to begin a dialogue of how to become the best version of myself.
- Adam Root, Hiplogiq

IMAGE: Getty Images
Last updated: Jul 16, 2014




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