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Why Asking Better Questions Changes Everything

with Dr. J.R. Briggs
  • Interviews

Why Asking Better Questions Changes Everything

with Dr. J.R. Briggs
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Better questions deepen relationships, strengthen our faith, and help us see what God is forming in us. Learn to ask like Jesus.

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Summary:

We study Jesus’ teachings, miracles, and parables, but how often do we study His questions? In this episode of Michael Easley in Context, Michael sits down with J.R. Briggs, author of The Art of Asking Better Questions, to explore how better questions can transform our relationships with God, ourselves, and others.

J.R. explains that the quality of our lives is deeply connected to the quality of the questions we ask. Thoughtful questions communicate genuine curiosity, create space for others, and turn ordinary conversations into opportunities for connection. Instead of shifting conversations back toward ourselves, we can practice keeping the “arrows pointing out” by listening, following up, and showing genuine interest in another person’s story.

The conversation also explores four essential qualities of good question-askers: curiosity, wisdom, humility, and courage. J.R. challenges believers to consider not only what questions they ask others, but what questions they ask during seasons of pain. Rather than remaining stuck at “Why did this happen?”, mature faith can begin asking, “What is God forming in me through this?”

Jesus modeled this beautifully. He asked more than 300 questions, inviting people to participate, reflect, and encounter truth. Learning to ask better questions may be one of the simplest—and most powerful—ways we can love God and love others well.

 

Takeaways:

  • The quality of our questions shapes the quality of our relationships with God, ourselves, and others.
  • Thoughtful questions keep our “arrows pointing out” by communicating genuine interest instead of shifting conversations back toward ourselves.
  • Good question-askers cultivate four qualities: curiosity, wisdom, humility, and courage.
  • Asking good questions requires listening well enough to allow silence and give people room to think and respond.
  • In seasons of suffering, maturity can move us from asking only “Why?” toward asking what God may be forming in us.
  • Jesus modeled the power of questions, using them to invite participation, expose the heart, challenge assumptions, and lead people toward truth.

 

ABOUT DR. J.R. BRIGGS

For more than 15 years, J.R. served in pastoral roles in mega-churches, church plants, and house church networks. Since starting Kairos Partnerships, he has coached a wide variety of leaders, including business owners, pastors, college presidents, non-profit directors, school superintendents, entrepreneurs, Chick-fil-A Operators, Blackhawk helicopter operators, and Division I college coaches.

In addition to coaching leaders and consulting with businesses, non-profit organizations, churches, colleges, denominations, and businesses, he also speaks and teaches regularly at conferences, retreats, and other leadership events.

J.R. also serves as the Director of Leadership & Congregational Formation for The Ecclesia Network. 

He has written, co-written, and contributed to 15 books on a wide variety of topics and published over 50 published articles, both online and in print, with Christianity Today, Huffington Post, Preaching Today, American Bible Society, N.T. Wright Online, Missio Alliance, Boundless.org and Relevant Magazine, and several others. His most recent book, The Art of Asking Questions (InterVarsity Press, 2025) is his passion project, as he is driven to help leaders grow to become better question askers. 

He hosts the Resilient Leaders podcast, a weekly podcast equipping leaders in a wide variety of backgrounds to grow in their health and effectiveness. 

 In addition to being passionate about serving and equipping leaders, J.R. loves swimming, kayaking, skiing, hiking, reading, traveling, eating sushi and Thai food, and passionately following the Philadelphia Phillies, Philadelphia Eagles and the Michigan Wolverines.

He and his wife Megan have been married for over 24 years and have two teenage sons, Carter and Bennett. They live in Lansdale, PA in the greater Philadelphia area.

Links Mentioned:

The Art of Asking Better Questions by Dr. J.R. Briggs

Dr. Briggs’ website

Watch the highlights and full version of this interview on our Youtube channel.

For more inContext interviews, click here.

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Topics

  • Discipleship, Personal Growth, Relationships, Wisdom

References

Tags

  • communication, curiosity, Discipleship, humility, leadership, listening, personal development, questions, spiritual growth, wisdom
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