The Art of Asking Better Questions with J.R. Briggs

Great leaders don’t just give answers. They ask better questions. J.R. Briggs joins Alan to unpack how curiosity, coaching questions, and practical reflection rhythms build trust, unlock growth, and transform teams.

Episode Summary:
If you’ve ever left a conversation wishing you’d asked a better question, this episode is for you. J.R. Briggs shares the mindsets and mechanics behind powerful questions at work, at home, in faith, and why leaders who cultivate curiosity build healthier, higher-impact teams. We explore obstacles like expertise traps, speed, and “question deserts,” then get tactical with preparation prompts, in-the-moment practices, and post-conversation reflection.

You’ll Learn:
• The difference between clarity questions and connection questions
• Practical coaching prompts: trade-offs, the capital-C Challenge, and “what do you really want?”
• How one courageous question (Darryl Davis) can disarm hostility
• A repeatable rhythm to prepare, participate, and reflect after conversations
• How asking better questions reduces decision fatigue and builds trust

Key Quote:
“Questions are pre-made decisions that make the moment simple.”

Giveaway:
Ask J.R. your question and enter to win his new book. Email hello@h2leadership.com with subject line “Question for JR.”

Links:

• H2 Leadership: h2leadership.com
• Email your question: hello@h2leadership.com
• The Art of Asking Better Questions