Curated Questions: Conversations Celebrating the Power of Questions! When Every Conversation Holds Possibility | Jeff Wetzler #36
"That is the question. What can I learn from this person?" - Jeff Wetzler
Jeff is a learner and teacher. Blending a unique set of leadership experiences in business and education, he has pursued this quest as a management consultant to the world’s top corporations, as a learning facilitator for leaders around the world, as Chief Learning Officer at Teach For America, and most recently, as co-CEO of Transcend, a nationally recognized education innovation organization. Jeff earned a Doctorate in Adult Learning and Leadership from Columbia University and a Bachelor’s in Psychology from Brown University. He is a member of the Aspen Global Leadership Network and is an Edmund Hillary Fellow.
In May of 2024, Jeff published his first book, Ask: Tap Into the Hidden Wisdom of People Around You, For Unexpected Breakthroughs in Leadership and Life. In this new work, he presents The Ask Approach™, based on a simple premise: tapping into what other people truly think, know, and feel is a game-changing superpower. In 2025 Jeff and his co-creator Emily Irving established the training and consulting firm ASK to promote the principles found in the book. Details can be found at askapproach.com, which includes a helpful assessment and an ever-expanding trove of resources for questioners.
Additionally, Jeff recently presented his TEDx Berkshires Talk entitled, "How to Learn Something from Anyone... (and Why To Try)," which is both entertaining and includes actionable takeaways.
In this episode of Curated Questions, host Ken Woodward welcomes Jeff Wetzler, a distinguished leader in business and education, to discuss the profound impact of asking quality questions. Jeff introduces his 'Ask' approach and elucidates how curiosity can transform leadership and personal growth. The conversation delves into various strategies for designing impactful questions, leveraging curiosity in conflict situations, and the importance of reflective listening.
Jeff also shares practical methods to expand one's natural curiosity, highlighting the role of intentional lifestyle choices in fostering this growth. Together, they explore how fostering genuine curiosity can lead to deeper connections and richer life experiences..
Episode Notes
[00:00] Introduction: The Power of Questions
[01:24] Meet Jeff Wetzler
[03:14] The Power of Questions in Childhood
[04:38] Encouraging Questions in Families
[05:57] The Sacred Invitation of Questions
[08:01] Quality vs. Crummy Questions
[09:11] Designing Effective Questions
[14:08] Listening to Learn
[14:43] The Three Languages of Listening
[16:07] Practical Exercises for Better Listening
[19:02] Question Strategies
[23:38] Rediscovering Natural Curiosity
[24:00] Breaking Through the Shell of Suppressed Curiosity
[24:28] Injecting Curiosity Sparks
[25:26] Heart-Centered Curiosity
[26:22] Living a Life of Curiosity
[27:09] The Importance of Scheduling Space for Curiosity
[27:51] Balancing Busyness and Productivity
[31:07] Broadening Perspectives Through Diverse Interactions
[32:54] Building Bridges Through Empathy
[35:15] Living the Questions
[36:12] The Overlooked Importance of Reflection
[37:51] The Right Now Question
[40:14] The Energy of Curiosity
[44:20] Awe and Wonder in the Other
[46:02] Final Thoughts and Takeaways
Resources Mentioned
Ask: Tap Into the Hidden Wisdom of People Around You, For Unexpected Breakthroughs in Leadership and Life by Jeff Wetzler
How to Learn Something from Anyone... (and Why To Try) Jeff's TEDx Talk
Jeff Wetzler on LinkedIn
Questions Asked
When did you first understand the power of questions?
Why does this happen?
How does this work?
Why is this going on?
Did your parents encourage that, or is that just who you were at that point?
When you were growing up, how welcome were questions for you?
Were you encouraged or discouraged as a kid?
Did she indicate that she's overcome that at all?
Can you say some more about how the second Amazing power of questions is they are Relationship Builders a sacred invitation?
What are your thoughts on working through and drafting questions for something that you can prepare for?
Are you trying to ask a question because you wanna prove a point or look smart or get someone to do something?
Are you really asking it because you wanna learn?
Does that make sense?
Does the other person agree?
Is it clear to them?
Do I understand what you're saying?
Do I agree with what you're saying?
What's your reaction to that?
How does that land with you?
How does that sit with you?
What does that make you think?
How much richer would life be?
How are you?
What are some elements of listening to learn?
What are you listening for?
What's the person saying?
What are the feelings that they're displaying?
What are the feelings that they're expressing?
What behaviors are they taking in the conversation?
What did I hear the first time around?
What might you be missing?
How can you start to train yourself to listen for the others?
What did the person say?
What was the information?
What was the content?
What were the emotions that were being expressed or displayed?
What were the behaviors or actions that they were taking?
How could that possibly be demoralizing to him or anybody?
How long does it take to get good at this?
What are recommendations or ideas for cracking that hard shell that may have grown over our curiosity?
What might I be missing?
What else could be going on in the situation?
How else might someone look at the situation?
Can we actually use empathy as a gateway in?
Do we surround ourselves with people who think just like us, or do we surround ourselves with people who think differently?
Do we surround ourselves with people who have the same general patterns of life experiences, or can we surround ourselves with people who have different life experiences?
How do we use our time?
What do we read?
What do we look at on social media?
What movies and TV shows do we watch?
Can we use all of that to kind of stretch our imagination of what's true in the world?
What's out there in the world, what's possible in the world?
How do we use our time in the sense of, are we packing our schedule so tightly that we're just doing, doing, doing, moving on from one thing to the next to the next?
Are we making space to just get bored, just to wander, to let our mind make connections?
How does one muster the courage to be curious about others?
How do we get that courage to really learn to listen?
What can I learn here?
What can I learn from this person?
How do they work?
What makes them tick?
What do they believe?
How is their behavior rational from their worldview?
What does that look like for you?
How do you live the questions?
How do I challenge my thinking?
Has there been a section of the book that maybe you think doesn't get as much attention as you thought that it might?
What is your right now question?
How can I and all of us access curiosity more deeply, more often?
Is that fair?
How would you define that?
What is going on here?
Do you have any thoughts or encouragement about questions that we haven't explored yet?
Where are the best places for folks to track you down and to learn more about what you're doing?