What If Asking Better Questions Changed Your Whole Life?

Blog by the Unhurried Living Team

When was the last time someone asked you a question that stopped you in your tracks — not because it was difficult, but because it was so good it opened something in you?

Most of us have been trained to value answers. We want clarity, solutions, the next step. And there's nothing wrong with that. But somewhere along the way, many of us stopped asking the kinds of questions that actually lead to wisdom, connection, and a life with God that feels spacious instead of squeezed. Asking better questions is not a technique or a trick. It's a quiet, countercultural practice — one that Jesus himself modeled — and it may be more transformative than any answer you've been chasing.

In a recent conversation on the Unhurried Living podcast, Alan Fadling sat down with author J.R. Briggs to talk about his new book, The Art of Asking Better Questions. What emerged was a rich, honest exploration of how questions can shape our faith, our leadership, and even our closest relationships. 

Curiosity and Humility: The Heart of Spiritual Formation

There's a reason young children ask tens of thousands of questions before they turn five. Everything is new. Everything is worth wondering about. But as we grow older, something shifts. We start valuing expertise over curiosity. We'd rather look competent than admit we don't know.

J.R. Briggs names this tension honestly: asking a question means giving up control. In a culture that prizes efficiency and productivity, pausing to ask — rather than rushing to answer — can feel deeply uncomfortable. But that discomfort might be exactly where growth begins.

Briggs identifies four essential postures for asking better questions: curiosity, wisdom, humility, and courage. These aren't communication skills you can pick up in a weekend seminar. They are spiritual virtues, the kind that are formed slowly over time in the soil of an unhurried life with God. Curiosity opens us up. Wisdom helps us discern what to ask and when. Humility reminds us that we don't already have it all figured out. And courage gives us the willingness to ask even when the answer might unsettle us.

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This is why asking better questions isn't just a relational technique — it's a formational practice. It shapes us. It makes us the kind of people who listen more carefully, who sit with uncertainty a little longer, and who create room for the Holy Spirit to do what only he can do.

As Briggs puts it, if we want deeper relationships — with God, with the people we love, with the communities we serve — we simply cannot get there without learning to ask meaningful questions. And the posture required to ask them well? That is formation in itself.

What Jesus Knew About Questions

If anyone had a reason to just give answers, it was Jesus. He is, after all, the Way, the Truth, and the Life. And yet the Gospels record roughly 300 questions that Jesus asked — questions that healed, challenged, revealed, and invited.

One of Briggs's favorite examples is the story of Bartimaeus. A blind man cries out to Jesus, and Jesus responds with what seems like an almost absurd question: What do you want me to do for you? It's obvious, isn't it? The man is blind. But Jesus doesn't skip the question. He invites Bartimaeus to name his longing, to speak his desire out loud, to participate in his own healing. And after Bartimaeus receives his sight, the text says he followed Jesus on the road. The question didn't just lead to a miracle — it led to discipleship.

This pattern shows up again and again in Jesus' ministry. He asked questions not because he lacked information but because he valued relationship. He wanted people to engage, to think, to come alive. His questions were never hurried. They created space — the kind of space where real transformation happens. 

For those of us who feel stuck in our prayer lives, Briggs offers a beautiful invitation: imagine Jesus asking you the same question he asked Bartimaeus. What do you want me to do for you? Sometimes the answer comes quickly. And sometimes, as Briggs shared, it takes months to reach the very bottom of what we actually desire. But the question itself — the willingness to sit with it — can uncork something that has long been blocked.

Alan Fadling added his own companion question, one he often invites people in spiritual direction to pray: God, how would you like to be with me? Where the Bartimaeus question says God cares about what's on your heart, this one says God might actually want to be present with you in ways you haven't imagined. Both questions are invitations to a more spacious, unhurried life with God.

Why Quick Answers Keep Us Small

There's a moment in the conversation where Briggs says something that's worth sitting with: being answer-oriented is often about needing to feel indispensable. When we always have the answer, people keep coming back to us. It feeds something in us. But it also keeps others from growing — and it keeps us from the kind of humble, curious leadership that actually bears lasting fruit.

Briggs names it directly: when a leader always tells rather than asks, it shortcuts the other person's growth, discovery, and maturity. Yes, it's more efficient in the short term. But Jesus' ministry, by modern metrics, was wildly inefficient — and yet wildly effective across millennia.

The late Peter Drucker once wrote that the leader of the future would be the person who knows how to ask, not just how to tell. Briggs builds on this, describing the best leaders he knows as "curious amplifiers" — people who don't need to be the smartest one in the room but who help others think, grow, and succeed through the quality of their questions.

This is a profoundly countercultural way to lead. In a world that rewards certainty and speed, choosing to ask instead of tell is an act of faith. It says, I trust that the Holy Spirit is at work in the person in front of me. I don't have to be their savior. I can be their companion.

For pastors, ministry leaders, and anyone carrying the weight of leadership, this is more than good advice. It's an invitation to lead from rest rather than striving — to trust that God is already at work, and that our job is often not to provide the answer but to ask the question that helps someone discover what God is already doing in them.

Four Ways to Start Asking Better Questions This Week

Growing as a question-asker doesn't require a degree or a personality change. Here are four practical starting points drawn from the conversation:

Start a questions journal. Keep a running list of good questions you hear — from a podcast, a conversation, a book, even a billboard. You don't have to come up with them all yourself. Write them down before you forget.

Replace one lazy question each day. Instead of "How are you?" try "What's the most interesting thing that's happened to you today?" or "Where are you experiencing joy these days?" A question that's even ten percent more thoughtful will open a completely different kind of conversation.

Pray with a question. Take the Bartimaeus question into your prayer time: Jesus, what do you want to do for me? Or try Alan's question: God, how would you like to be with me? Let the question sit. Don't rush toward an answer.

Practice with Scripture. Choose a familiar passage and try to generate ten to fifteen questions about it before reaching for any answers. You'll be surprised at what you see when you approach the text with curiosity instead of certainty.

An Invitation to Slow Down and Wonder

The heart of this conversation — and of J.R. Briggs's book — is an invitation. Not to master a skill but to recover a posture: the childlike wonder that Jesus said was essential to the kingdom of God. Children are natural question-askers. They haven't yet learned to pretend they already know. And Jesus said that unless we become like them, we miss something essential.

Asking better questions is not about being clever. It is about being present — to God, to the people around us, and to the stirrings of our own souls. It's an unhurried way of living, and it just might change everything.

If this resonated with you, we'd love for you to listen to the full conversation between Alan Fadling and J.R. Briggs on the Unhurried Living podcast. And if you know a fellow leader or friend who could use a slower, more spacious way of engaging with God and others, share this post with them. We're all learning together.