5 Questions Every Mentor Must Ask

An effective diagnostic tool that can provide better guidance to mentees, employees, or generally anyone with whom you are playing the role of a counselor.

Jan 11, 2016 | BLOG POST

As the celebration of National Mentoring Month continues this January, this post highlights what mentors should do in order to create the optimal mentoring foundation for their mentees. The right mentor not only provides guidance and encouragement, but also brings out the best in their mentees in helping them achieve their goals. The Harvard Business Review’s Guide to Getting the Mentoring You Need, introduces a mentorship framework comprised of five critical questions that every mentor must ask to help optimize the mentoring relationship. As highlighted and discussed below by Anthony Tjan, CEO and founder of the venture capital firm Cue Ball, he notes, “These five questions, when asked in the order presented, form an effective diagnostic tool that can provide better guidance to mentees, employees, or generally anyone with whom you are playing the role of a counselor.”

1. What is it that you really want to be and do? This question is about aspiration and purpose. The reason why someone is doing what they are doing should come out here. The question is also meant to get at the business goals and broader aspirations of an individual – someone wishing to be successful in business so that they can do more to help others, for example. The answer to question one should surface the driving passion of individuals – what is it they do or wish they could be great at doing?

2. What are you doing really well that is helping you get there? This question helps spotlight a core strength and the person’s ability to execute towards his/her goal. What is someone naturally good at doing? Detailed and standardized operations? Leading and motivating staff? Numbers? What is it that someone does better than the average person that can help her achieve her aspiration?

3. What are you not doing well that is preventing you from getting there? This is about facilitating an honest and critical assessment of the roadblocks, challenges or weaknesses in a person or company that is slowing their ability to win the game; to meet the goal from question one.

4. What will you do different tomorrow to meet those challenges? Questions two and three help determine whether people are spending the right time on the right things. Progress cannot be measured just by hard work. Someone may have a great work ethic, but if he is not focused on the right priorities, then “you’re making good time, but you’re lost,” as another one of my partners likes to say. People also have a tendency to practice and repeat what they are already good at doing. It is human nature to show off your best side and hide weaknesses. As a kid playing racquet sports, I remember being asked once why I kept practicing my forehand when my backhand sucked. Use this question to probe whether the person has the aptitude to change behavior. Will the person practice start practicing his backhand?

5. How can I help / where do you need the most help? The answers to the first four questions matched against areas where you as a mentor have particular strengths, relationships, or learning resources – should help determine how you can best help someone achieve the goal.

Learn more about how you can get involved with mentoring and contribute to ICMA’s National Mentoring Month conversation using #ICMAmentors.



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