Mentoring Means Asking Tough Questions

The management of the company that employs a friend of a friend asked all employees to find a mentor. Interesting in and of itself. But the story starts when my friend, asked by his friend to be his mentor largely out of respect for his technical knowledge, turned to me to ask what it meant to be a mentor. Here was my response:

Thanks for the compliment and for keeping me in mind.

I find the best thing I can do for a protégé is to ask questions that inspire them/wake them up to the need to ask themselves what they really think or why they are doing something or what they really want. While your friend may be asking for technical help, I find that most people do not need much help in technology (external) issues, but internal (thinking) issues. So while he is asking for a mentor because his work is telling him that is a good thing to have, he is trying to apply it to his work knowledge, and that is not what mentoring is good for. He needs a teacher or a coach for that. Send him to Google and YouTube with a plan for what to search on and how often to check back in with you on what he has learned and that piece is done.

The best gift you can give him is to help him think through his current circumstances from the start: why are you in that job? What do you really want to do with your life? What tells you that this job will get you there? When you sit silent in the mornings (I recommend a meditation routine for all my protégés) do you feel good about the people you work with and the work you do – or not? If you could do anything you wanted, regardless if whether or not you could live off it, what would that be?

Do you see where I am going here? The biggest value you can offer to your friend is to facilitate a discussion he has to have with himself. In the end he will have learned more about how to administer a network, but he will also know—for now—why administering a network is the right thing for him to be doing. Even more important, he will have gone through a process he should do routinely in order to be sure that what he is doing is right for him.

Remember this: a mentor may not take their protégés to fun places. That’s someone else’s job (friends, spouses, etc.). You as his mentor are there to ask the tough questions and keep making him dig deeper. Use the law of five whys – keep asking why until you really arrive at the essence of the issue. (“Why are you doing this job?” “Because it’s all I could find” “Why?” “Because I tried for 3 months and this was the only offer.” “Why did you stop there?” “Because I had bills to pay.” “And why did you stop looking after you found this job?” and on and on until you finally hear something deeply personal, e.g. “Because I don’t think I am that smart!” NOW you have something you can address and work on fixing!)

Is this making sense? Is this something you want to do? If not, it’s best to suggest your friend find a life coach, someone who does this for a living. On the up side, it’s a good thing to do for others and for yourself. I ask myself the same questions that I ask those who come to me for counsel. I’m not quite as tough on myself as I am on them, but it does force me to evaluate my own circumstances routinely to make sure I am on track.

I am sure there are good books and blogs on the myriad of questions that you can ask someone in a role as mentor. Let me know what you find. Let me know what you decide to do, will you?

Thanks again for the trust and value assessment!

John Maxwell on Leadership and MentoringI trace my own developing understanding of mentoring back to books my mentors gave to me, both to understand their approach to me, as well as to leave to a third party the training of the fine points of mentoring. The definition of mentorship talks about “an ongoing relationship of learning, dialog, and challenge.” Since many of my mentors lived a great distance, books became a good way to provide progress between interactions. Among the more memorable was John Maxwell, a prolific author on the topics of leadership, teamwork, and mentoring. His books came to me in a period of my life when I aspired to own and manage companies, a focus that has since passed I might add. Knowing that such a role was not going to be successful based solely on my limited experience as a paperboy and lawn service, I looked to other successful business leaders and asked them to share their time and experience.

Regardless of your occupation, level of community involvement, or interest in being relatable to others, I found great value in reading up on leadership, teamwork, collaboration, and mentorship. Have you done such reading and found it of value? I’d be interested in hearing your stories. Maxwell tells a short story about the inspiration behind creating the Big Brother movement. Even in something as simple as counseling a child wise enough to ask for help, great things can be done to help them, and through them many others. Witness the impact of Salman Khan and his Khan Academy, all sprouting from an attempt to help his young cousin understand challenging math concepts from a distance.

Who have you been mentored by? Who have you mentored? I would appreciate hearing from you!


2 Replies to “Mentoring Means Asking Tough Questions”

  1. I’ve been fortunate to have mentors at many different steps in my life, be it through Scouts, my limited sports activities, communities I’ve joined and work. I think you made an important point in this post, the mentors who have been most effective and made the most impact on me don’t care about being my “friend,” yet I’ve always maintained an understanding of mutual respect.

    As I have started to mentor some of the people I’ve worked with in the past, I realize I am pulling on advice many of my mentors have given to me, bits of wisdom that have become part of my personal philosophies. “Be on time,” “work on the things you care about,” “It’s ok to fail sometimes,” and “Cut distractions from your life” all seem like no-brainers, but are crucial bits of advice that finally sunk into my head after often long and difficult conversations with my mentors.

    Ultimately, my mentors have always helped me re-frame my failures and shortcomings to make them productive experiences. I think this is the most important role a mentor plays that sets these relationships apart from any other types of relationships I’ve had. A mentor is someone you feel comfortable dissecting an otherwise bad situation with, identifying why that situation happened, and evaluate the response.


  2. You bring up an interesting aspect of mentoring that I only implied, Neal: the need for trust and candor between both parties. How a mentor is found often dictates the relationship, and with it – the trust. Long-time friendships that evolve into mentor/protégé arrangements benefit from known history. But third-party introductions force a “cold-start scenario” that amplifies the burden of trust on the protégé.

    Mentoring among women support groups would be an interesting study to see how these rapid pairings affect process and outcomes. One such group is mentioned in this post by Connie Chow:

    Has anyone had a mentoring experience with no prior knowledge of your mentor?


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