The Art & Science of Asking Better Questions: Unlock Trust, Learning & Leadership with Jeff Wetzler.

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“Your desire to know cultivates their willingness to tell.” – Jeff Wetzler

In this episode of It's an Inside Job, I sit down with Jeff Wetzler, author of Ask: Tap Into the Hidden Wisdom of People Around You, to explore the transformative power of asking the right questions. Jeff shares how curiosity, psychological safety, and deep listening are essential for meaningful conversations and effective leadership. 

Why You Should Listen: If you've ever left a conversation feeling like something was left unsaid, this episode will equip you with practical tools to ask better questions, listen more deeply, and build stronger relationships. Whether you're a leader, coach, or simply someone who wants to communicate more effectively, Jeff’s insights will transform the way you approach conversations.

Key Takeaways:

1. Curiosity is a Choice, Not a Trait – Jeff emphasizes that curiosity isn't something you either have or don’t. Instead, it’s a mindset shift that we can intentionally cultivate, especially in emotionally charged moments. By choosing to be curious, we invite deeper understanding and create a foundation for trust and learning.
2. The Art of Psychological Safety – People often hold back valuable insights due to fear or discomfort. Jeff breaks down practical ways to make it safer for others to share their true thoughts—whether it's through choosing the right setting, exposing our own agenda transparently, or demonstrating resilience in handling difficult truths.
3. The Quality of Our Questions Determines the Quality of Our Learning – Many of us unknowingly ask ‘clumsy,’ ‘sneaky,’ or ‘attack’ questions that shut down dialogue rather than open it up. Jeff walks us through his five-step Ask Approach, offering specific strategies for crafting open-ended, neutral questions that foster honest and insightful conversations.
4. Deep Listening is More Than Just Hearing – Too often, we listen to respond rather than to understand. Jeff introduces techniques like ‘pulling the thread’ and ‘echoing’ to actively engage in conversations, ensuring we fully grasp both the words and emotions behind what someone is saying.
5. Turning Insights into Action – Learning doesn’t stop at hearing—it requires reflection and follow-through. Jeff shares his ‘Sift It and Turn It’ method, a structured approach to processing information, extracting key insights, and translating them into meaningful change.

Bio

​Jeff Wetzler is a co-founder and co-CEO of Transcend, a nonprofit organization dedicated to supporting school communities in creating extraordinary, equitable learning environments.  Prior to co-founding Transcend, Jeff served as Executive Vice President of Teacher Preparation, Support, and Development, and Chief Learning Officer at Teach For America, where he focused on optimising the training and ongoing support of thousands of corps members nationally.

In 2024, Jeff authored the book "Ask: Tap Into the Hidden Wisdom of People Around You for Unexpected Breakthroughs in Leadership and Life," which explores the power of asking questions to uncover insights and foster breakthroughs in leadership and personal development.  

Contact

Website:  https://www.askapproach.com/

LinkedIn: 

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