Questions In Mentoring

Why are you reading our blog?...

…Wait! Don’t leave us yet. Odds are you want to, given the question we asked at the head of this post. We asked the wrong question and asked it in the wrong way. Ours was an intentional error, designed to capture a reader’s curiosity and spur a discussion about questions in mentoring.

Who asks the questions in mentoring?

To satisfy curiosity about good questions in mentoring, we first must answer this one: who is the questioner? Most advice on questions in mentoring is aimed at the mentoree. This post and this one are typical.

This advice is good as far as it goes, but at Leadership Design Group we believe it comes from a flawed view of mentoring. It assumes that the mentor is a wise guide who must be mined for valuable wisdom to be transferred to the mentoree. Thus, the mentoree’s task is to ask questions designed to release that wisdom.

Our view of mentoring is far different. Because the best of mentoring is designed to help those we mentor explore and discover how to thrive in all of their life, the mentor is the best questioner in a mentoring relationship. For that reason, the following thoughts are directed at those who seek to attain to the best in mentoring, though we believe them broadly applicable to any student of questions.

Four guidelines for the best of questions in mentoring

The best of mentors will ask questions in a way that invites mentorees to explore their own soul and discover key pathways to becoming all they are designed to be. Here are four guidelines to good questions in mentoring:

  1. Only ask a “yes or no” question if you are intentional about wanting a “yes” or “no” answer. “Yes” or “no”, like other one-word answers to poorly designed questions inhibit introspection and exploration. They will not get mentorees to the level of discovery we seek in the best of mentoring.
  2. Avoid “Why” questions. This is our intentional error at the top of this post. Though “why” is a valid question and can get to a deeper level of introspection, it can also obscure the point of a question or be interpreted as accusatory or in other ways put mentorees on the defensive, with a felt need to justify or explain. This will interfere with a mentor’s goal of helping mentorees explore and discover.
  3. Ask questions that are intentional in design to elicit an answer from the depth of mentoree’s souls. We find the technique of asking mentorees to describe something as one of the five senses to be very helpful at reaching the deep level of introspection necessary for healthy exploration and discovery.
  4. To reach an even deeper level, ask this question: “Is there anything else?” Mentorees, particularly when we are probing an uncomfortable topic at depth, almost always are holding back some key piece of information that will prevent both the mentor and mentoree from reaching real discovery. This one question, if accompanied by a mentor’s willingness to sit in silence as long as it takes to hear an honest answer, very often will allow us to reach real levels discovery that result in deep change necessary for mentorees to thrive in all of their lives.

Beyond “Why”

Let’s return to our intentional error at the top of this post. The “why” in the question made it obtuse. Did we want to know what you were seeking when you came to our blog site? Or maybe we wanted to know how you were drawn to the post, what method or forum that attracted you to us. Though no writer we know of would do it, it may have been designed to chase you away: “What are you doing here? Shouldn’t you be somewhere else?”

Whatever else the question did, it no doubt inclined you to the defensive. Here’s one way to discover how much we put you on the defensive: describe your reaction to our initial question as a sound. Go ahead. Do it right now. Better yet, tell us in the comments section below what your initial reaction was and describe it as a sound. What did you learn from the exercise?

Our intent in asking the question was to discover what makes you curious about questions in mentoring. There are myriad ways of changing the question that makes its purpose clearer and elicits a deeper and more introspective answer. Here are three:

  • “What 2-3 curiosities about questions in mentoring brought you to this blog post?”
  • “How would knowing more about asking good questions help you in a current or anticipated mentoring relationship?”
  • “Who asks the bulk of the questions in your mentoring relationship? How does their use (or non-use) of questions deepen (or weaken) the outcomes of your mentoring?”

Any of these approaches would invite some real thought in the answer. A mentor who listens to the answers will find a rich trove of possible follow-on questions that will take them ever closer to answers that lead to true discovery and transformational change in those they mentor.

Is there anything else?

How might we be of additional help to you becoming among the best of questioners? Let us know in the comments section.

Free Resource

LDG_ebook_coverFor more information on designing leaders through Intentional, Deep-Change, Whole-Life, Transformational Mentoring, download our free eBook.

Written by

Tim is uniquely designed to think strategically into the future and build plans to move an organization from the present to that future. He has a passion for developing young business and military professionals. In his role as CEO for LDG, Tim exercises his unique personality to serve, help form and co-lead LDG’s new initiatives. He has the creative responsibility for delivering world-class leadership design through mentoring to a variety of business, educational, government, arts, sports and non-profit organizations. Tim also helps to oversee the selection, training and management of a network of Leadership Master Mentors for Leadership Design Associates.

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