The Quality of Your Questions

The best mentor-mentee relationships thrive on curiosity and powerful questions. Mentors should resist the urge to “fix” problems and avoid prescribing specific actions. Mentees should focus less on being who they think their mentor wants and more on approaching interactions with a willingness to learn, grow, and discover how to think.

I am always seeking great questions to facilitate these interactions. Recently, I discovered three excellent questions while listening to the audiobook Clear Thinking* by Shane Parrish. Parrish suggests that when seeking advice, your goal should be to understand how the other person thinks, not just what they think. Although his book is not specifically about mentoring, the questions he proposes can be highly beneficial for both mentees and mentors.

Questions Mentees can ask their Mentors
Mentees might ask….

1. What variables would you consider if you were in my shoes?
How do these variables relate to one another?

2. What do you know about this problem that I don’t?
What can you see based on your experience that someone without it cannot?
What do you know that most people don’t?

3. What would your process be for making this decision if you were in my shoes?

Questions Mentors can ask their Mentees
These questions are also valuable for mentors. Instead of offering solutions or suggestions, mentors can prompt their mentees to reflect by asking:

1. What variables in this decision are important to you?
Who else or what else does this decision impact?

2. What are you most worried about in making this decision?
What possibility excites you the most?

3. What have you tried so far?
What do you think is the best process for this decision?

These questions encourage reflection and empower mentees to solve both the current problem they are facing and future problems. They also enable mentees to develop authentic solutions that fit their unique needs, values, and learning styles.

What questions have you used to encourage clear thinking in your mentoring relationships?

*Clear Thinking by Shane Parrish: (Farnam Street, 2023, ISBN: 0593086112)

The quality of your questions
Top Ten Reasons to Buy The Mentor’s Guide, Third Edition

Top Ten Reasons to Buy The Mentor’s Guide, Third Edition

Major Changes to the 3rd Edition

Major Changes to the Third Edition

Since the first edition appeared in 2000, interest in and knowledge about adult learning and development has grown exponentially. We now recognize that adult learning is more than a cognitive process; it is a multidimensional phenomenon. The uniqueness of the adult learner has been accentuated over the last decade as we continue to learn about more the complexities of the brain, multiple types of intelligence, and our emotional selves. All of this has meant fundamental changes for mentoring, and for this guide. Among the major changes:

  1. A full two chapters are now devoted to the importance of context and connecting in mentoring, including an exploration of the context of difference and the context of how people come together to connect with one another in the relationship.
  2. Conversation between mentors and mentees are drawn from actual mentoring experiences in a variety of situations, including business, government, nonprofit, and higher education, and reflect the diversity of the global workplace.
  3. There is more discussion and emphasis on mentoring relationships embedded in  context including a consideration of the context of other differences—sexual orientation, gender, and race—in the mentoring relationship, with many examples 
  4. The chapter on the context of connection has been expanded to include physical, virtual, and personal context, with special attention to how virtual mentoring connections  offer new ways to create and enhance positive mentoring relationships.
  5. The section on mentoring matches addresses seeking, selecting and evaluating a potential mentoring relationship.
  6. Additional examples have been included along with an enhanced mentor skills list and updated approaches for starting your mentoring relationship.
  7. The goal setting process has been expanded from SMART goals to SMARTer goals, adding to the specificity and measurability of the process.
  8. There is an enhanced conversation guide to help mentors evaluate mentee learning goals, full consideration of emotional triggers that impact mentoring and guidance for co-creating your mentoring partnership 
  9.  Includes more emphasis on trust, including the dynamics of self-trust and interpersonal trust
  10.  Includes updated and enhanced content on feedback including how to get back on track when stumbling blocks get in the way. Explores the dynamics of the feedback process with many more examples and a feedback checklist for mentors.
3 Fun Resources (About Mentoring)

3 Fun Resources (About Mentoring)

For a change of pace, here are a few resources (2 that are unlikely) related to mentoring.

#1 – A great Ted X talk

Check out this great TEDx Talk by University of Maryland professor Dr. Kimberly Griffin. There are great references to Marvel comics and reality TV, as well as three critical takeaways:

  • Remember mentoring is about relationship.
  • Don’t seek one mentor to provide answers to all your questions. Instead, create a group of mentors who can provide a variety of guidance.
  • Be mindful of the rule of reciprocity — Think about what you have to give to your mentors, not just what you have to get.



screenshot from her TEDx Talk via YouTube.

Dr. Kimberly Griffin during her TEDx talk

You can find Dr. Kimberly Griffin on Twitter: @doctorkag

screenshot from her TEDx Talk via YouTube.

Find Cara Allwill Leyba on IG: @thechampagnediet

#3 – A Classic film

I first saw Cinema Paradiso when I was a teenager, and I remember getting goosebumps then.  I still love this film, which reminds us how a mentor’s voice can shape us, stay in our heads, and guide our decisions long after the mentoring period has passed.



    #2 – A Poem

    This poem reminds us that we are constantly evolving the importance of taking ownership of our learning and growth.

    Worthy by Cara Alwill Leyba (from the book, Stripped),

    You must aggressively
    detox yourself
    from negative thoughts,
    poisonous people,
    and disempowering beliefs.
    You must believe
    with every thread of your heart
    that you are worthy.
    You must make your personal evolution
    a full-time job.



    Learn together, but don’t get stuck on the escalator

    Learn together, but don’t get stuck on the escalator

    One way to harness the power of mentoring is for mentor and mentee to study something together. I employ this practice in one of my current mentoring relationships. My mentee and I choose a topic and find a book or article related to the topic to read between our monthly sessions It’s been an excellent way for both of us to learn and to guide our discussions.   

     Here are some tips to make this work for you:

    Agree on the mechanics.

    Decide who will choose the reading and how much of it you will discuss at the next meeting.

    Keep it relevant.

    Make sure that the topic is related to the mentee’s goals. In mentoring, learning is always for the sake of development, and it should be tailored to the mentee’s learning objectives. 

    Right-size the homework.

    Nothing kills follow-through like being overwhelmed. If you choose a book, break it into chapters and agree to read a few chapters, The idea is to generate enthusiasm for learning together, not to slog through the material.

    Come prepared to discuss.

    Remember that this reading is just for enlightenment; it is an opportunity to learn together. Mentors, resist the temptation to teach or lecture. Plan on discussing what you learned and how you think this might relate to your mentoring objectives.

    Create an implementation plan.

    I used to live in Washington, DC, where there are crazy long escalators that go down to the metro stations. There are times I would feel like the ride on the escalator was as long as the rest of my commute. Some people hate those escalators, and even have nightmares about getting stuck on one and never making it home! Like many fears, there is no explaining this one. Even if the escalator abruptly broke down, you wouldn’t be stuck on it. You could always walk up-or down the escalator to get to your next destination. 

    The reliance on reading to create change is a little like waiting for someone to fix the escalator. At some point, you may have to use the skills you have to get the results you want. Knowledge will only get you so far. After you discuss your learning, create an action plan to bring that learning to life. 


    Why can’t my manager be my mentor too?

    There are some really great managers in our workplaces today. These managers understand the importance of focusing on the development of their employees.  They take the time to build relationships with the people whom they manage.  They create a safe space for learning, inquiry, and even for making mistakes.  They are great role models, advisors, and coaches.   

    So why do I discourage mentees from choosing their supervisor as a mentor?    

    Before I answer, here is an important distinction.  I DO believe that good managers should develop the competency of mentoring.  I DO believe that when managers mentor others, it helps them become even better managers. But while it is important for managers to be mentors,  I DO NOT think that managers should mentor people who work for them.

    Here’s why:

    There are two characteristics of a supervisor/employee relationship that make it less than ideal for a mentoring relationship:

    A manager’s primary accountability is to the business’s success, not the employee’s career.

    Ultimately, a manager is responsible for their team’s performance and must put the organization’s interest first, even when it conflicts with the employee’s interest.  Managers are hired to perform a specific job and to make sure their team’s performance is in service to the outcome they are hired to achieve.  Sometimes, an employee’s interests might be at odds with that responsibility.  Perhaps the employee’s best career path would take them out of that team, out of that company, or in a different role.   A manager’s allegiance to the organization compromises their impartiality when they mentor their own employee.

    A mentor’s primary accountability is to the development of the mentee. Since a mentor is not tethered to performance metrics, they can provide an additional unbiased perspective that can help a mentee develop in a way that is authentic to their own needs.

    A manager is responsible for evaluating their employee’s performance and job security, which includes determining their compensation and career trajectory.

    No matter how good the manager, ultimately, they have a say in their employee’s compensation.   For mentoring to be effective, a mentee must feel safe sharing their challenges and shortcomings.  It isn’t easy to build that safety when one’s job or livelihood is at stake.

    There are some essential roles a manager can play in mentoring, however. 

    Mentees:  Enlist your manager in your mentoring by:

    • Asking for help in finding a mentor. Share what you want to learn.  Ask them who they know who might be a good learning fit.
    • Helping you identify learning goals. Ask your manager what skills, competencies, or knowledge they think you can strengthen or amplify.  If those recommendations resonate with you, use them as a basis for setting goals in your mentoring relationship
    • Giving you feedback on your progress. Share your mentoring goals with your manager.  Ask what improvements they have observed.