Barriers to Asking Questions

In this conversation, host Dave Ripper welcomes Dr. J.R. Briggs to explore how asking better questions can transform our lives, leadership, and walk with God. Drawing from J.R.'s book The Art of Asking Better Questions: Pursuing Stronger Relationships, Healthier Leadership, and Deeper Faith, they discuss the power of questions to connect, discern, heal, and draw out what God is already doing in us and others. The episode weaves personal stories, biblical insights (including Jesus as the ultimate question-asker), the concept of kairos moments, mentorship influences like Eugene Peterson and Gordon MacDonald, and practical ways to ask life-giving questions of God, ourselves, and others. Includes a guided reflective practice using the "inner compass" to notice God's presence and invitations.

Guest Bio

Dr. J.R. Briggs is the founder of Kairos Partnerships, an organization dedicated to serving hungry kingdom leaders through coaching, consulting, speaking, and teaching. He serves as Director of Leadership and Congregational Formation for the Ecclesia Network and teaches on leadership and spiritual formation at institutions including Friends University and Taylor University. J.R. is a prolific author of books such as Fail, The Sacred Overlap, and The Art of Asking Better Questions. He hosts the Resilient Leaders Podcast and lives in the greater Philadelphia area with his wife and sons.

Key Topics & Highlights

• Kairos Moments: Understanding kairos (opportune, God-invaded time) vs. chronos (sequential time). How leaders steward unexpected invitations—whether joyful or painful—and why faithful response benefits everyone.
• The Power of Questions: Questions hijack the brain, foster connection, build trust, spark creativity, and reveal worldview. The quality of our lives and relationships often depends on the quality of our questions.
• Personal Influences: J.R. shares his father's modeling of question-asking, studying Jesus' questions in the Gospels, and a 12-year mentorship with Eugene Peterson (sparked by bold questions at a thank-you event).
• Mentorship & Formation: Stories of Eugene Peterson's key question ("What is God doing in your congregation right now?") and Gordon MacDonald's decade-based questions (e.g., "What kind of old man/woman do I want to be?").
• Growing Fruit on Others' Trees: Shifting from self-focus to educe (draw out) what the Holy Spirit is doing in others through curious, motive-checked questions.
• Questions to God: Guests share honest questions they'd ask if God guaranteed an answer (e.g., Why is grace so hard to receive? Why mosquitoes? How to make sense of trauma?). Dave reflects on questions like "Lord, what is this time for?" and "What's Your unexpected invitation in my unwanted suffering?"
• Questions We Ask Ourselves & God: Moving from statement-heavy prayers to question-filled ones (as in the Psalms); reminders that God not only loves us but likes us.

Reflective Practice: The Inner Compass

J.R. leads a guided prayer using a compass rose for noticing God's presence:

• North (North Star / Faith deepening): Where does my trust in Christ need to grow? Who/where is Jesus guiding me deeper?
• South (Southern Light / Longings): What do I long to become or do? Where do I need joy and delight in this season?
• West (Setting Sun / Release): What must I let go of (fear, resentment, despair, false certainty)?
• East (Rising Sun / Welcome): What new opportunity, relationship, or kairos moment do I need to embrace?

Listeners are invited to sit with these questions prayerfully, even while multitasking.

Resources Mentioned

• The Art of Asking Better Questions: Pursuing Stronger Relationships, Healthier Leadership, and Deeper Faith by J.R. Briggs
• Kairos Partnerships: kairospartnerships.org
• J.R.'s website: jrbriggs.com
• Resilient Leaders Podcast
• Books by Eugene Peterson (e.g., pastoral theology works beyond The Message)
• Gordon MacDonald’s A Resilient Life (chapter on decade-specific questions)

Connect & Next Steps

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Find more episodes and show notes at podcast.daveripper.com.
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Grace and peace to you as you pursue deeper life with God through the simple, powerful practice of better questions.