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Mentoring and Beautiful Questions

Listening is an essential skill in mentoring. It provides a safe space and the attention needed to convey validation and worth.  Oftentimes mentors also have the opportunity to problem-solve with their mentee. To be successful we must be prepared to ask the right questions not only to our mentee, but first to ourselves.  This is important work and must be entered into intentionally.  

In a new book entitled The Book of Beautiful Questions, author and proclaimed “questionoligist” Warren Berger delves into the research on the power of inquiry.  It is written for individuals who wish to make changes in their work and relationships.  There are valuable takeaways for mentors as well. By using Berger’s thoughtfully crafted questions, and replacing judgement with curiosity, mentors can help themselves and their mentees sort through the fog. 

It is human nature to see others’ problems and situations through our own life’s lens.  Our experiences, beliefs, fears, and hopes can cloud our perspective.  Well-intentioned advice can easily fall flat and not help at all.  

To ensure you are looking and listening from a fresh angle before you begin problem solving with your mentee,

Ask these four questions to check your biases and beliefs

  1. What am I inclined to believe on this particular issue?  Start by trying to articulate your beliefs and biases.
  2. Why do I believe what I believe? This question per Nobel prize winning physicist Arno Penzias, forces you to consider the basis of those beliefs.
  3. What would I like to be true? A desirability bias may lead you to think something is true because you want it to be true.
  4. What if the opposite is true?

To see the world differently, ask...

  • What might I notice if I were encountering this for the first time?  Apply this fresh eye approach to your job, the people around you, your everyday path to work.
  • What if I stand on my desk?  Not necessarily to be taken literally, but try changing the angle from which you view things.
  • What is in the background?  Try to focus on that which is usually obscured or ignored.
  • What here would fascinate a five-year-old or a ninety-year-old?  What would Seinfeld be amused by?  Use a comic observer’s eye to look for inconsistencies.
  • What would Steve Jobs be frustrated by?  Use an innovator’s eye to notice inadequacies.

Now that you are ready, skip giving advice and ask these seven questions to help your mentee figure it out

  1. What is the challenge that you are facing?
  2. What have you tried already?
  3. If you could try anything to solve this, what would you try?
  4. And what else?  Repeat this two or three times, as needed to surface additional ideas.
  5. Which of these options interests you most?
  6. What might stand in the way of this idea, and what could be done about that?
  7. What is one step you could take to begin acting on this, right away?

The most important thing to remember in asking questions is avoid asking “why.” 


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