Saturday, June 27, 2026

The Art of Asking Better Questions (J.R. Briggs)

"We live in a world that has conditioned us toward answers . . . asking good questions is a lost art." So begins J.R. Briggs in his book The Art of Asking Better Questions. An outline follows.

"Asking better questions is a mindset. It is a posture. A way of life." And when we ask more (and better) questions with genuine interest in, and love for, others, everyone wins. "Asking great questions has the power and potential to improve the quality of every single area of life—your relationships, your career, your faith, and your future." And so this book is "about questioning-asking, where we wseek to ask questions that emphasize honor, care, discovery, and growth."

Why do we ask questions? For clarity and engagement. To cultivate connection and intimacy. To "scrutinize our presuppositions and help to dismantle assumptions." The questions we ask reveal our values and shape our thoughts. Asking genuine questions means giving others attention, which is a gift and form of generosity; questions "make conversations go deeper and last longer."

The author's four essentials to asking great questions:
- Curiosity. "Curiosity shines a spotlight, brings awreness to our assumptions and blind spots, and opens doors."
- Wisdom. We must ask questions wisely. "The questions we ask, how we ask them, and why we ask them at all reveal a great deal about who we are at our very core."
- Humility. "Great question-askers are fully aware of and quite comfortable with their ignorance."
- Courage. We have "to be confident in our lack of knowing, to willfully admit we are ignorant about a particular topic."

And he provides the Four Levels of Good Questions:
- Level One: Questions for information (simple facts).
- Level Two: Questions for interaction (thoughts and emotions).
- Level Three: Questions for understanding (feelings and desires).
- Level Four: Questions for transformation (vulnerability and intimacy).

He then looks at various things, including:
- The questions we ask ourselves. What does that reveal? Do we assume others are asking the same questions?
- Why does God ask questions? What does that reveal about His heart? 
- Why does Jesus ask questions? Here, he looks at the centrality of questions in Jesus' life, the six reasons He asked lots of questions, the types of questions he asked, and more.
- What questions do we ask God? How does question-asking help spiritual formation?

He concludes with practical ways to ask better questions: nine ways to prepare, 20 practices you can do while asking questions, and how to look back and reflect.

He offers several resources in the back of the book, including a discussion guide, lists of questions to ask yourself, discussion questions for faith communities, and fascinating facts about the questions Jesus asked.
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I liked a lot of things in this book. I need to ask better/higher-level questions, and this gave me the tools to help. It reminded me of the importance of good questions and how they cultivate connection and community. It was valuable to study how God asks questions. This is a good resource.

At the same time, the book got repetitive; he spends a lot of time across several chapters convincing us of the need for and benefit of questions. I was sold early, so that got old and muddled the distinctiveness of each chapter. This could have been shorter.

I did like that he offered lots of questions throughout the book; here are my three favorite:
How can I be helpful?
Do you want to be helped, hugged, or heard?
Why am I bothered right now? 

Rating: B

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