Five Key Questions to Ask your Mentor

You’re excited you’ve connected with a mentor who is committing to help you.

However, is this individual the right fit for you? Has the connection come through a trusted recommendation, a mentor introduction website or at a local bar?

However you connect, it’s prudent to ask your potential mentor a few questions to clarify things from the very beginning. This clarification can minimize stress and a great deal of time-waste down the road.

If the investor in your business or startup is mentoring you, you will have done due diligence on each other (we sincerely hope), as at this point you may not have the choice to opt out of the mentoring relationship!

Keep in mind, these FIVE KEY questions are to clarify and learn about your mentor, not to put him or her on the spot!

1. What is your mentoring style?

If you only were able to ask one question, this would be it! Find out if your mentor-to-be asks questions and expects you to find the answers and create an actionable plan based on the answers. Ask your mentor if he is interested in sharing his experiences; both his successes and failures. Find out how much your mentor will advise vs. tell you what to do? How much will be direction, how much collaboration? Does your mentor-to-be expect you to become a clone of him/her?

This question is to discover the mentors methods and expectations, not to find the mentor with the easiest approach. An effective mentor will give you the confidence to do things that you thought you could never do…so it may not be easy, and you may need to stretch and adjust your horizons upward. Select a mentor who will inspire you to go your limit, and then beyond!

2. How much time will you be dedicating to the mentoring?

Will this be a regularly scheduled time and place, as in once a week, twice a month for an hour or so? Will we meet at your office, my office, a neutral location, or will we be meeting virtually via Skype, Hangout or phone? Leaving this arrangement “up in the air” to “when we feel like it” or “as needed” is a recipe for the mentoring relationship to be ineffective for both parties. Busy people may need to reschedule established meetings; however if it’s firmly in place it can be rescheduled!  At least when the mentoring relationship starts, structure can equal commitment, later it can evolve to what works best for both of you.

Find out if your mentor-to-be will accept being contacted by email and IM between sessions, understanding however that reaching out for insignificant requests, ranting or complaining will get old fast. However, a mentor who has your interests at heart will be receptive to short, focused communications between scheduled sessions, when their input can make a difference.

3. Have you mentored others’ successfully?

Of course the answers to this will be subjective, unless you are lucky enough to talk to someone who has received mentoring from your mentor-to be.

However, you should be able to gauge his or her interest and commitment from these answers; most mentors I know will be pleased to share their mentoring experiences, especially what they learned from them! You will also learn more about the mentor and style of mentoring from these answers, so listen closely to hear why something was or was not successful!

4. What commitment (time & focus) do you expect from me?

This is an important question, so you will clearly understand what is expected of you the mentee, in terms of time, commitment and focus. Being a mentee has it’s own mindset.

When you lay the cards on the table during the initial meeting with your mentor-to be, make sure you ask what he/she expects and be sure you really understand what is said or implied; failing to meet “fuzzy” expectations is one of the reasons mentoring most often fails.

Expectations on both sides need to be fully discussed and clarified. Remember that mentoring is most often a process that takes time and is not a one-shot deal. Mentors don’t solve your problems….they mentor you to solve them!

5.What do you expect in return for your time and expertise?

Most mentors I have had and know, work as I do, voluntarily. My pay-back is your success, whether it is realization of goals, overcoming challenges, or financial reward for the person I mentor. However, working hard, getting smarter, doing good are all different but quite equal ways of paying me back for my time and expertise.

Not all mentors work for this kind of payback, so it’s important to clarify expectations of specific payments / stock options / work trades, at the very beginning. I once got a bill for 12K from someone whom I thought was doing it gratis, as payback had never been discussed!

Summary: Those preliminary discussions, asking the right questions of your mentor-to-be can be very important to set the stage for a hassle free relationship, especially as there necessarily may be plenty of “Sturm und Drang” as you evolve and grow, solving challenges and accomplishing goals together! And trust me, expect your mentor to ask you some of the same questions!

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