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

Your Mentoring Year, Recap

You’ve come so far in your mentor/mentee relationship! Take a breath and take a look at all you’ve accomplished over the past 12 months.

Do you remember where you began a year ago? What was the quality and tone of that relationship then? What were your goals and visions?

Where are you now…and even more exciting, Where are you headed for the next 12 months?

Next month we begin a whole new series of tips! So, dream, journal and wonder at your next level…and stay tuned for more.

A Clear Message To Mentors About the Importance of Listening

In a recent survey conducted through our Center for Mentoring Excellence, listening emerged as the top mentoring best practice. Readers of our monthly e-letter, Mentoring Matters, also identified listening as the #1 attribute of a good mentor.

Here’s what they told us about listening:

  • Listening at all levels is the most important thing that I do.
  • Listening to others and helping them find their own way.
  • Listen with an open mind without being judgmental.
  • Truly listen so assumptions are not being made.
  • Listen fully and carefully before offering your advice or opinion.
  • Spend more time listening than talking.
  • Listening and questioning to help my mentee reach their solutions.
  • Be authentic, be warm, be honest and be an engaged listener.
  • Mentors should know themselves well enough to know when their personal strengths or biases cloud the way they listen to and encourage/advise their mentee.
  • Hear what is said in between the message, not just listening to what is said.
  • Read, observe, listen and ask lots of questions

There is a clear message here about the importance of listening.

Listening serves many purposes in addition to letting mentees know that you care. Listening builds mentee confidence. It lets mentees know they have something meaningful to contribute. Listening encourages them to work out their thinking. Invariably, they arrive at a solution on their own. Mentors often discover that the listening skills they develop through mentoring transfers to other functions, boosting their effectiveness in their other leadership roles.


What can you do to improve your skill at listening?

  • Identify the good listeners you know.
  • What do they do that shows they are listening?
    Make a list of those behaviors and then gauge how you measure up.
  • What do you need to do more of?
  • What do you need to do less of?
  • What is one thing you can work on right now that will help you develop and hone your listening skills?
Conversation: The Key to Building Trust and Facilitating Learning in a Mentoring Relationship

Conversation: The Key to Building Trust and Facilitating Learning in a Mentoring Relationship


Can you recall the last time when you were engaged openly and respectfully in two-way, free-flowing really great and meaningful conversation? If you are like most people you can probably recall one or two such occasions even though you may be engaging in real conversation less and less these days.

It is ironic that in the very process of connecting with each other, we are actually becoming more and more disconnected. Technology has made connecting more expedient but, at the same time, it has affected how we interact and engage with each other.

Mentoring relationships run the risk of becoming a series of sound bites (text and IM) instead of real conversations. Engaging in conversation increases trust and facilitates learning in a mentoring relationship.

We developed the Levels of Conversation model to illustrate how trust and learning expand relative to the level of conversation that takes place in a mentoring relationship.

Monologue is essentially a non-conversation. It shuts down, rather than invites, conversation. It doesn’t build trust or promote learning. One or the other party claims all the airspace for storytelling, lecturing or expounding.

Most people engage in transaction when they mean to be in conversation. The conversation goes back and forth and remains on the surface. I.e., “Would you do me a favor? Yes. Did you read that article? Good.”

Interactions are useful information exchanges and approximate conversation but still skim the surface. Your mentee asks you how to get something done and you respond by suggesting different ways to get the job done.

Good conversation lives above the dotted line. With the move to collaborative engagement the quality of the interaction shifts. This is where deeper insight and reflection take place. There is more trust and therefore mentor and mentee are both willing to be vulnerable. The conversation and relationship deepen and learning accelerates to a new level.

When conversation becomes dialogue, shared understanding emerges from the mutual learning that is taking place. Because trust is high there is no defensiveness. Conversation is open. As different perspectives emerge, the thinking of mentor and mentee expand.

The further along the continuum you are the more trusting your relationship becomes and the more learning takes place.

Leadership Questions: Good conversation is the key to building trust and facilitating learning in a mentoring relationship. Where are you and your mentee spending most of your time along this continuum? What do you need to do more of? What do you need to do less of?

This just might be the time to have a conversation about conversation and find out!