All About Mentoring and Asking Good Questions

by Lois Zachary

Ever been asked a really good question that gets the wheels turningEvolving as a mentor or coach and asking really good questions in your head about your future? If you’re young, that question could be about whether you want to head up a company one day and what your plan is to decide whether that’s the path you want to take.

The power of mentoring happens when the mentor asks thought-provoking questions to stimulate the mentee to reflect about creating his/her own future.  Here’s an example of the Before and After lessons of a mentor. In this case, Kathy Button Bell,a CMO who was interviewed by Adam Bryant of the New York Times.


“I was probably not as good a manager when I was younger because you’re so worried about what you’re doing, as opposed to developing people… I love mentoring people, but I think when I was younger and mentored people I was trying to get them to the next level, not get them to the C.E.O.’s office.”


“I’d say I’ve shifted from shallow to deep in terms of mentoring.  Now we talk a lot more about looking at the end of the story, of where you envision yourself.  Do you see yourself as an operation’s leader?  As a president of one of our companies? Or do you want to be in my job someday?  And then asking: What do you need to do to make up your mind about that?  What should you try along the way to give yourself a better sense? It’s like playing as many sports as you can to figure out which one you’re good at.

I think the shallow-versus-deep issue is about asking those bigger, richer questions about who they want to be.  I think you want to ask them about being delighted in life and what would make them incredibly happy.  And what would make them proud?  I think it’s easier to look at that instead of saying, ‘O.K., you need to dress better for work or take less vacation.'”

I’ve re-read this column numerous times. Although Bryant titled his interview, “Endurance on the Field and at Work,” the way I see it, it could just have easily been called “All About Mentoring”. It is a testimony to the power of mentoring, the centrality of learning in a mentoring relationship for both the mentor and mentee and the importance of a mentor who asks thought-provoking questions.

Mentoring is something I know a little bit about having written and read extensively about the topic for the last twenty years.  What I appreciate most about Kathy Button Bell is that she is obviously a continuous learner. She is self-aware, willing to learn about herself and is committed to her own growth and development as a mentor.

You see, I believe that a mentor’s good intention to mentor is insufficient to do a good job. Mentoring isn’t something you do out of your back pocket. It is a leadership competency and that means that you can get better if you work at it. It takes time, willingness and experience. I also believe that there is a standard of practice to which one can aspire. I call that mentoring excellence. Bryant gives us a glimpse of it in his interview: a continuously learning mentor, a reflective mentor, a mentor who is growing in the role.

Lois Zachary is the President of Leadership Development Services, LLC. and an international expert on mentoring and leadership development. She has written several books on mentoring. The newest one is The Mentor’s Guide: Facilitating Effective Learning Relationships. Other books include Creating a Mentoring Culture: The Organization’s Guide, and The Mentee’s Guide: Making Mentoring Work for You.

About Lois Zachary

Since The Mentor's Guide was first published in 2000, it has become the primary resource for organizations interested in promoting mentoring for leadership and learning and for mentors seeking to deepen their mentoring practices. Zachary is president of Leadership Development Services, LLC, a Phoenix-based consulting firm that specializes in leadership and mentoring, and director of its Center for Mentoring Excellence™.
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