CNLP 773 | How To Hijack the Brain of Your Audience: J.R. Briggs on Why the Best Leaders Are the Best Question Askers

Summary

Podcast Summary

The Carey Nieuwhof Leadership Podcast – Episode 773
Title: How To Hijack the Brain of Your Audience: J.R. Briggs on Why the Best Leaders Are the Best Question Askers
Date: December 16, 2025
Host: Carey Nieuwhof
Guest: J.R. Briggs

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Episode Overview

This episode dives deep into the art, science, and spiritual impact of asking better questions—personally, in leadership, and from the pulpit. Carey interviews J.R. Briggs, founder of Kairos Partnerships and author of "The Art of Asking Better Questions," about why skilled question-asking is an underestimated tool for connection, change, and leadership excellence. They explore how question-asking transforms relationships, brains, sermons, and organizations, offering hands-on strategies and memorable stories. The conversation also flips in the final third, with J.R. putting Carey in the interviewee seat, modeling real-world question-asking in action.

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Key Discussion Points & Insights

1. Why Question-Asking Matters in Leadership and Life

• J.R. developed a passion for questions from his upbringing, mentors, and a deep dive into Jesus’ questions in the Bible (03:33–05:04).
• Quality and frequency of questions directly shape connection, depth, learning, and personal growth.
• J.R. asserts:
  "I can't think of a single area of our lives where improving the quality of our questions will not improve the quality of our lives and the lives of the people around us." (04:40)

2. Questions and Emotional Intelligence (EQ)

• EQ is closely tied to the self-diagnostic questions we ask ourselves (05:25–06:36).
• Asking “How am I being read in this room?” or “Am I adding value?” builds self-awareness and empathy.

3. Is the Art of Conversation Dying?

• Social media and digital communication have shifted interactions to status updates instead of dialogues, leading to "conversational narcissism" (06:36–11:00).
• The “waitress rule”: If you finish your meal before your conversation partner has eaten, you might not be asking enough questions (08:31).
• J.R.: "The cultural headwinds push us to rush to judgment, not curiosity ... conversational narcissists where the arrows are pointing in." (08:31)

4. What’s at Stake? Loss of Connection

• Loss of question-asking diminishes connection, creativity, and healthy relationships (11:58–13:12).
• Even God, omniscient, asks questions to foster connection and intimacy.

5. Pandemic Impact and Exhaustion

• COVID-19 increased exhaustion and acedia (spiritual apathy), making basic connection and question-asking feel exhausting for many leaders (13:50–15:31).
• Downstream fatigue affects curiosity, motivation to reach out.

6. The Leader as “Answer Person” vs. Chief Question Asker

• Organizational culture expects leaders to have answers, but true influence and learning come from asking (19:45–21:14).
• Peter Drucker’s insight:
  “The leader of the past may have been the person who knew how to tell, but the leader of the future will be the one who knows how to ask.” (20:00)
• Younger generations value a “guide on the side, not a sage on the stage.”

7. The Value & Power of “Dumb” Questions

• Being willing to ask “dumb” or basic questions often opens up deeper understanding and connection (24:18–26:16).
• Larry King’s style: ask what the average, uninformed listener would ask.

J.R.: "The moment you ask a question, you're admitting I don't know the answer. And that's really hard for a lot of people in our culture today." (25:41)

8. Obstacles to Asking Good Questions

• Barriers include the desire to look smart, fear of awkwardness, living in a “question desert,” and disincentives in efficiency-driven cultures (28:03–31:02).
• "In some cases, asking questions in boardrooms is penalized ... Questions can be perceived as inefficient in our efficiency-oriented world." (29:25)

9. Jesus as the Master Question-Asker

• Jesus asked over 300 questions, was asked about 180, and directly answered only 5 (31:15–31:54).
• Life change often followed Jesus’ questions, not answers.

10. How Questions “Hijack” the Brain

• Neuroscience shows questions stimulate the entire brain—literally “hijacking” attention and focus (33:18–34:31).
• "When you ask someone a question, you can temporarily hijack someone's brain ... the brain is wired automatically to say, 'How would I answer that?'" (33:44)

11. Using Questions in Preaching and Public Communication

• Jesus’ teaching style included physical, emotional, and mental “field trips,” heavily involving questions (36:58–39:43).
• Rhetorical questions in sermons invite engagement and self-discovery, rather than passive consumption.
• Try opening or closing a message with a jarring, thoughtful question.

12. Practical Advice for Leaders and Young People

• Be aware: monitor your content, quality, frequency, and direction of questions (41:32–43:05).
• Predictable, superficial questions (e.g., “How are you?”) rarely yield rich answers; tweak language for specificity and depth.

13. Better Questions in Everyday Life

• Move past yes/no and leading questions; ask open-ended, thought-provoking queries.
• For kids: "What did you learn today you didn’t know this morning?" instead of “How was your day?” (45:10–45:56)
• In sports interviews: “Who’s the first person you’ll call after this win?” or “What did you learn from your slump?” (48:14–49:41)

14. How to Engage with Influential People

• Ask permission before jumping into questions with high-profile individuals (50:20–51:57).
• Prepare a few thoughtful questions in advance, aiming for questions your hero has never heard before.

J.R.: "If you show interest and ask some thoughtful questions, it is like water for a parched soul." (53:11)

15. Flipping the Mic: J.R. Interviews Carey

- The final segment showcases skillful question-asking in action as J.R. explores Carey’s motivation, growth, and podcast philosophy.
- Carey identifies curiosity as an antidote to cynicism, shares practical “meal test” hacks for checking question balance, and discusses how great interviewers build trust through vulnerability (59:03–68:03).
- Both reflect on their growth and impact through question-driven conversations.

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Notable Quotes & Memorable Moments

• On Connection:
  "I can't name a single healthy relationship that I have in my life that has not been cultivated without questions and vulnerability and intimacy. All that happens. And those kids are greased by the questions that we ask one another." – J.R. (12:00)

• On Leadership Shift:
  "The leader of the future will be the one who knows how to ask." – (20:00, paraphrasing Peter Drucker)

• On Jesus’ Questions:
  "We study his miracles, his parables, his healings, his teachings. We don't study his questions. And yet that's where the bulk of life change happened." – J.R. (32:49)

• Hijacking the Brain:
  "When people were given answers, their brain lit up. When they were asked questions, their brains lit up like fireworks ... you can temporarily hijack someone’s brain." – J.R. (33:18)

• On “Dumb” Questions:
  "The moment you ask a question, you're admitting I don't know the answer. And that's really hard for a lot of people in our culture today." – J.R. (25:41)

• Practical Example:
  “What color are your shoes right now?” – J.R. (34:06)

• On Interviewing:
  "If you get the guest to say, ‘Huh, that's a good question. I've never been asked that before. Can you give me a minute?’, you're giving them a gift." – J.R. (53:11)

• On Preaching:
  "Hijack people and they're locked in and ready to go. ... From ‘listen to me’ to ‘what did you bring to this?’" – Carey & J.R. (39:15–39:27)

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Essential Timestamps

• 03:33 – How J.R. became obsessed with questions
• 05:04–06:36 – Self-questioning and emotional intelligence
• 08:31–11:00 – Cultural shift: “conversational narcissism” & code word “waitress”
• 11:58–13:12 – What we lose: connection
• 13:50–15:31 – Pandemic exhaustion & acedia
• 19:45–21:14 – The leader as the answer person vs. the lead question-asker
• 24:18–26:16 – “Dumb” questions: Larry King & purpose
• 29:25–31:02 – Obstacles: curiosity deserts, fear, efficiency bias
• 31:15–31:54 – Jesus: 300+ questions, 5 direct answers
• 33:18–34:31 – Neurological impact: “hijacking the brain”
• 36:58–39:43 – How to use questions in preaching
• 41:32–43:05 – How young leaders can improve questions
• 45:10–45:56 – Everyday upgrades: parenting and better questions
• 48:14–49:41 – Better athlete interview questions
• 50:20–53:11 – Approaching high-profile people; “gifts” in thoughtful questioning
• 59:03–81:18 – J.R. “flips the mic” and interviews Carey

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Actionable Takeaways

• Audit your question habits: Check your content, quality, frequency, and direction.
• Upgrade everyday questions: Go beyond “How are you?” to something more specific or creative.
• Practice curiosity: Curiosity is a discipline—prepare questions even for casual interactions.
• Lead with questions: Fight the urge to be the “answer person;” model inquiry and invite participation.
• Hijack attention with questions: Use questions deliberately in preaching, teaching, and team meetings to engage minds.
• In interviews/meetings, prepare the questions only you can ask: Aim to make guests/colleagues say, “No one’s ever asked me that before.”
• Recognize obstacles: Name and address your fear of looking “dumb,” your drive for efficiency, or your instinct to control conversations for your own status.

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Podcast Tone & Style

Engaging, conversational, practical, and vulnerable—both Carey and J.R. blend research, scriptural insight, personal stories, and hands-on advice in a style that is authentic, thoughtful, and often humorous.

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Conclusion

This episode is a must-listen (and re-listen) for anyone who communicates, leads, or simply wants deeper connection in a distracted, answer-obsessed age. J.R. and Carey offer both rationale and practical hacks for leveraging questions to open up minds, hearts, and deeper learning.

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Recommended Resource:
Pick up J.R. Briggs’ "The Art of Asking Better Questions" (contains an appendix of great questions) and start experimenting—your leadership, relationships, and spiritual life will all benefit.

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For more show notes and resources, visit careynieuwhof.com or The Art of Leadership Academy.

Transcript

[A]

The Art of Leadership Network.

[B]

It has made us what Charles Durber calls conversational narcissists. And the cultural headwinds push us to rush to judgment, not curiosity. I don't mean to sound like Ted Lasso here, but there's so much media and government leaders, you know, social media, but that conversational narcissism where the arrows are pointing in and the joke is, you know, enough about me. What do you think about me?

[A]

Welcome to the Carrie Newhoff Leadership Podcast. It's Carrie here, and I hope our time together today helps you thrive in life and leadership. Well, today we are talking about the art of asking better questions. I think this is a huge neglected leadership area. Nobody really asks questions anymore. And I talked to a guy. This is the best conversation I've ever had about asking questions. You're going to learn some really practical hacks. You're going to learn why it's important, and this is going to improve your eq. Everybody talks about, you know, how am I more emotionally intelligent? Well, better questions. It really, really helps. Hey, I want you to know, too. I'd love to for you to follow along with my travels. And you can do that best on Instagram. We spent about a month in Franklin, Tennessee, Nashville this fall. And everywhere I looked, I was like, just running into friends from this podcast. John Acuff, Noah Heron, a lot of other people. I track all that kind of stuff on Instagram and would love to have you follow me there. I'm just Carrie Newhoff on Instagram, by the way, preachers, if you want to hijack the brain of your audience, JR Briggs tells you exactly how to do it. And we also discuss why leaders are the best question askers. He is the founder of Kairos Partnerships, an organization committed to serving hungry leaders through coaching, consulting, and speaking. He serves on staff with the Eklassia Network and and Fresh Expressions and as a guest for Friends University in the Masters of Spiritual Formation and Leadership program. He's written numerous books, including the Art of Asking Better Questions. And now my conversation with JR Briggs. Well, jr, welcome. Really good to have you.

[B]

Thanks so much, Carrie. It's a joy to be here on the show.

[A]

You've done an impossible feat. You wrote a book on questions that was fascinating from start to finish. So congratulations. I told you I went out and got my own copy because I want it in my library. It's like, normally you read the PDF. Okay, I'm ready for the interview. But like, man, great job.

[B]

Thanks so much. I really appreciate that.

[A]

How did you become interested in asking Questions, because this has been a 10 year project.

[B]

Yeah, several factors. I was fortunate enough to grow up in a home where this was modeled. Well, I know not everybody has that opportunity. Both my parents, but especially my father and I just watched the way he would interact with my brother and me and with neighbors and people in the narthex at church. And I just found myself saying, wow, he's really involved in a lot of interesting conversations. And so that was modeled really well. I also began to see it as a powerful tool by watching my father and others utilize that and what you could learn and the amount of depth and connection that was happening because of it. And then I began to notice a pattern. The people that I admired, that their lives were inspiring. I was drawn to them. I wanted to be like them. I realized they asked great questions. And the people that lived somewhat small and uninspiring lives where I wasn't drawn to spend a lot of time with them, I've found that they weren't asking many questions. And I realized that everyone asked questions, but the difference was the quality and the frequency of the questions. And so I began a social experiment several years ago and said, you know, I'm going to try this out myself in informal conversations and just see if I were to stretch myself just a little bit more by asking some more thoughtful and engaging questions, could I interact with people and find it to be richer and more interesting and enjoyable and connecting? And it absolutely was. And then the last element, Carrie, was I just did a deep dive in trying to learn the questions of Jesus and began to realize that, my goodness, here's the way, the truth and the life. If anybody had the right to never ask a question again, it would be Jesus. And yet he asked over 300 of them. And the amount of change and transformation that occurred when a question was asked by him. I began to say, I need to pay attention to this. There's some power here. We need to wake up this latent giant of this tool that God created called questions. And so I just realized that asking great questions has the power and the potential to improve the quality of every single area of our lives. In fact, I can't think of a single area of our lives where improving the quality of our questions will not improve the quality of our lives and the lives of the people around us. And so those factors were the driving force behind really realizing we've got to pay attention to questions. They're there. I'm just not sure we realize how powerful they are and what a tool they can be.

[A]

Is Question asking somehow connected to EQ emotional intelligence? And if so, how so?

[B]

I have wondered this many times. I've not seen any studies on this directly. I do think the questions we ask ourselves has a huge influence on our eq. The questions say more about that.

[A]

What do you mean?

[B]

Yeah, the questions we may not verbalize out of our mouth, but the questions we're asking, like, how am I being read in this room? How are others perceiving me? Right. Those are some of the key elements of high eq. And so being able to see myself in someone else's shoes requires me to ask some of those questions. Where am I adding to the conversation? Where am I adding value? Where am I getting in the way? Am I being too loud? Am I talking too much? I mean, these are all self diagnostic questions that we have to ask ourselves first. And I think there is an element to that. I have been around those who've struggled with EQ and sometimes they, and I'm coaching some of them, they say, I want to get better at that. I actually start with questions and say we've got to think about the frequency and the types of questions we ask ourselves before we act or before we open our mouths. And so seeing some change on that has started with those. But I've not seen some studies. I'd love to see some studies if they're available because I think that's a very important research project. If it's not, well, that's good to know.

[A]

You actually did your research. This is not just musings on questions. It's like it's an accessible scholarly work, which I really appreciated. But you know, my wife and I, this has been like a theme that we probably dug out at least a decade ago. Maybe this goes back 15 years. It's come up from time to time on this podcast. I remember having a meaningful conversation with Gordon MacDonald on one of the episodes he was on. And it's a pet peeve of him and his wife too. Like sometimes you can go out and you can spend two or three hours at a dinner, you know, on a trip, you know, in some kind of interaction and nobody asks you a single question. So I want to break that down a little bit. Is the art of conversation dying? And I want to give you my theory and I want you to have blow it apart. I'm thinking, and maybe this is like a superficial analysis, but like since social media came along, the pattern I've noticed is that we give each other status updates. Like, you may not ask me a question, but I'M going to volunteer information whether you asked it or not. And then unrelated to what I just said, you're going to give me a status update on what you did or what you're thinking and then I'm going to return not the volley, but I might start a whole other subject. Or we just like it's weird because it's not cause and effect. And you know, I'm old enough to have a long pre digital memory conversation was a lot of cause and effect, like, oh, how about this? Or oh yeah, that's interesting. Oh well, you know, that made me think about and that seems to have died and like my wife spent three or four hours just very recently before we recorded this episode out with Someone who shall Be nameless. She made three or four hours of conversation, not one question back at her. And I wish I could tell you this was a isolated incident. So please feel free to disagree, comment. But are you seeing that? Like what's going on?

[B]

Yes. And unfortunately that is common. My wife and I actually have a code word for this. If I'm meeting someone for lunch sometimes this happens more frequently than I would enjoy. But when I come home, she said, how was your lunch today? And I said waitress. And that's our code word meaning I ate my meal, the waitress took my plate away before the other person took a bite or two. And even giving pauses, it's not like I'm just rapid fire, but of just allowing spaces for them to ask. And it still wasn't returned. And we know that feeling. It's a very lonely feeling. I say that not for pity points, but of just saying, yes, this is a major issue. And I think this is an issue just in the last couple decades actually because and I actually think your theory, I think you're right on the ubiquity of screens now. In fact, you just look around at gate when you're waiting to catch your next flight. The screens have already won. So because of that, it has made us what Charles Durber calls conversational narcissists. And the cultural headwinds push us to rush to judgment, not curiosity. I don't mean to sound like TED Lasso here, but there's so much media and government leaders, social media, but that conversational narcissism, where the arrows are pointing in and the joke is enough about me. What do you think about me? And that's sort of the world in which we live in. But the definition even of leadership has been buttressed by the idea of an expert thought leader. I'm trying to Imagine what would it be like if we were able to platform people who are question leaders instead of just thought leaders. And so there's a countercultural side to it. And is it a lot of work? Yes, but it is so worth it if we're willing to do that. And then I think the pandemic, we're still seeing downstream consequences of the pandemic and screens and that mixture together, I really believe is an issue. Former US Surgeon General Vivek Murthy, I mean, he, his book together came out just like two months before the pandemic hit, and he's called it an epidemic of loneliness. And of course, it just got worse when the pandemic went on. So I think your theory, I think you're right on when it comes to screens and volunteering, whether people want to hear it or not, I'm just going to blast it out and you're going to hear what I'm, what my update is on my life.

[A]

So, you know, oh, boy, there's so many places I want to go here. J.R. you know, one argument, I mean, increasingly those of us with pre digital memories are going extinct, right? Like, you know, digital natives are now in their 30s. You know, they got smartphones when they were in high school, et cetera, et cetera. And I mean, Gen Z, Gen Alpha, totally immersed in the digital universe from the time they were born. You know, iPads as babysitters, the whole deal. So you can make an argument that culture changes, right? That, okay, you're old, this is how you do conversation. This is not how the world today does conversation. Get with the program. So I'm open to the fact that that might be an argument, but my question is, if that becomes the norm, right, where it's conversational narcissism and status updates flung at each other, what are we losing, J.R. like what, what is at stake here?

[B]

Yeah, one word. I think we're at risk of losing connection. And that is connection could be new ideas, could be creativity, new perspective, but especially in relationship. So here's the God of the universe who knows everything, and yet he still asks tons of questions in the Old Testament. And I would say that if God could ask that and those questions still ring true and teach us new things millennia later. I think questions don't have a shelf life. They may look different, they may be valued different generations. But when I look at this and say, man, if they're, you know, God knows everything and yet he continues to ask questions, but it's not for information. We, as finite beings, we need Questions for information. We have our limits, of course, but here's a God who has no limits, and yet he still asks question after question after question. Why? For connection. To connect with his own creation. And I can't name a single healthy relationship that I have in my life that has not been cultivated without questions and vulnerability and intimacy. All that happens. And those kids are greased by the questions that we ask one another.

[A]

Questions as connection. That's a really interesting framing because you mentioned downstream impact of the pandemic, which is now, for all intents and purposes, six years ago, it kind of went away. And then in mid-2025, I started hearing a lot of leaders. I'm talking to, talking about, still recovering from. And we're not talking about church attendance anymore. We're not talking about staffing, but they're saying, man, this seems to be lingering. So what happened to question asking or to the way we communicate during the pandemic?

[B]

I think exhaustion really set in and is still set in. As I work with a lot of leaders like you do as well. Those kingdom leaders are saying, I think my adrenal glands are shot. I could go on adrenaline for a while, but because my adrenal glands are shot, I just don't know if I have the effort. I mean, I could ask questions, I could reach out for connection, but sometimes I just want to veg on the couch and just watch Netflix and Doom scroll. And sometimes that becomes our escape. And so I'm not. We do need those down times, and I'm not saying we should do away with those entirely, but there is that exhaustion that's beyond just getting a long nap. And I'm concerned for leaders. Even though, yeah, we think really, we've moved on from COVID I still think that those effects are lingering. When it comes to trauma, we talk about the body keeps the score. I think exhaustion. The body keeps the score as well. And when our adrenal glands are shot, you know, and I know you've, you know, you had your own season of burnout, as a lot of leaders have. Oh, my gosh, you know, adrenaline. Your adrenal glands are shot, and there's just nothing left in the tank. So I do think that's a factor. I'm not sure it's all burnout. I just think it's, you know, lowercase, a acedia that sets in that just says, you know, I'm just too tired to care anymore. You know, we sort of one of the seven deadly sins, we call it sloth, but it really. The word is acedia of just a spiritual torture. Just eh. I just don't know if I've got it anymore and so I just am too tired to care. So that concerns me a little bit. That's bigger than questions, but I do think that has connected to questions significantly as well.

[A]

This episode is brought to you by glu. So ministry leaders, you know you're called to serve, to connect, and to change the world. But doing that often means fighting technology that wasn't designed for your mission. And that's why GLUE is here, to build a trusted technology platform that serves the faith ecosystem. So Glue is transforming how you lead by providing a complete platform of values aligned tools and technology that help churches understand and connect with congregants, reach new people and help engage them in compelling ways. So with solutions like Glue Workspace, where ministry leaders get work done, and partners like Igniter Media, Barna Visitor Reach and Outreach, Glue is providing the digital backbone for the faith ecosystem, equipping your church, your ministry and people to thrive in the digital age. You can learn more about how GLUE can help you to do what you're called to do by texting my name Carrie C A r e y to 46816. That's Carrie to 46816. This episode is brought to you by my 2026 Church Trends. Hey, as you head into 2026, watch Cultural Shifts, do you need to keep an eye on as a church leader? I mean, it's a really big question, right? You got your head down trying to do the work from day to day, but there's some big stuff happening, right? You and I both know how easy it is to get caught up into the week to week of ministry, sermons, meetings, you know, Sunday after Sunday grind. And you just miss what's really going on in the culture. That's why every year I release my annual Church Trends report. And it's to help you see what what's next and to lead with clarity. So for 2026, I've identified seven disruptive trends that are shaping the future of the church. And we're seeing Gen Z's surprising surge in church attendance. They're kind of leading it, something very few people expected two years ago. There's a new boldness in evangelism I'm going to be talking about, and maybe the most concerning of all. Most churches still aren't ready for the AI revolution that's already reshaping ministry and leadership. So those are just a few of the trends that we'll be unpacking this year. The trends are backed by data, and I share my thoughts on why it's important and what you can do about it. So this year I'm doing something new. All the trends are premiering live inside the Art of Leadership Academy. You'll not only get the full 2026 Church Trends Report and the Leader Guide, but also a live interactive Q and A and podcast series. All of that is launching in January. So if you want to be the first to access it, head on over to 2026ChurchTrends.com for free. Free access. Once you've signed up, you'll be in the loop for everything related to my 2026 church trends report. Again, it's all free, so just click the link in the description of this episode or visit 2026churchtrends.com the future of the church is still bright, especially for leaders who see it clearly and who respond wisely. One of the stresses that or one of the positions leaders have, right? We've talked before on this show many times about when you get to a certain position on the org chart, you stop hearing the truth. Truth is the first casualty. First casualty of war, first casualty of leadership. Right. Like, if I have the power to hire and fire you, why would you give me 100% of the truth? But I think one of the other things that happens that we haven't talked about or explored as much, junior, is that when you become a leader, you are seen to be the answer person. Right? Like you are the one who has got it all figured out. And of course, if you sat in the chair for 20 minutes, you know that we're all making this up as we go along. But I am anyway. I definitely am. But it's one of those things where I found myself. Cause I've been in senior leadership for three decades now. I've only been the lead pastor or the CEO now for 30 years. And the occupational hazard of that is that people always come to me with questions and I am tempted to just give answers. So I've had to really cultivate staying curious. How much is that a factor for leaders when you stop asking questions or when you're always the, quote, answer person?

[B]

Yeah, there's a cultural expectation that exists. I mean, the expectation is to have that intelligent, confident, articulate, charismatic, and let's just be honest, male leader up front giving all the answers. Right. And so what? I love this quote from Peter Drucker, you know, the organizational guru. I mean, he said this, I don't know, few decades ago, but he said the leader of the past may have been the person who knew how to tell, but the leader of the future will be the one who knows how to ask. And I think that's more true now than it was a few decades ago when he said that. And so that fundamental shift from leader as answer giver to leader as lead question asker is. It takes some courage because it is countercultural. And younger generations have expressed that they would rather have a guide on the side than a sage on the stage. Right. And so we need to pay attention to that. That. Because I think there is a possibility, even though faces are in screens, maybe more with younger generations, they really do desire a guide on the side a lot more than a sage on the stage. Doesn't mean it goes away, but they want that person shoulder to shoulder, walking alongside of them, asking questions, because they haven't always had that in their lives. And so I think that that's going to be a key factor moving forward in reaching younger generations. Even how we think about evangelism, it's going to have to be more question oriented, at least from the start, than it is just giving answers.

[A]

So I take it you weren't buddy buddy with Drucker. There was a generational overlap there as well. So you might say, I have no idea. But I'm curious, even from a reasonable speculative standpoint, what do you think Drucker saw several decades ago when he wrote that or when he flagged that? What do you think he was sensing?

[B]

There's another story with Drucker that was fascinating. When people asked him, so what is your job? He said, I'm hired. I was hired to ask dumb questions. And people went, ha, ha. And then they laughed like we just did. And he said, no, I'm serious. I'm hired to ask dumb questions. And they pressed him, what do you mean? He said, I'm going to ask the question that seems so obvious. You're going to think I'm crazy until I ask you to answer it. And you go, hmm, I've never thought about that. I don't know. And so he was constantly pushing on assumptions. And I found that to be fascinating. Here's this brilliant guy, you know, the guru, the founder of the organizational leadership movement, and he says, I'm hired to ask dumb questions. I think he was so comfortable and had enough courage and his own identity to not be wrapped up in. I need to be seen as the expert answer giver. I think that's why he stood out. He asked the questions no one else was asking.

[A]

Interesting. So I'm an amateur student of the art of the interview. I say amateur because I've done some research, but not enough for sure. And there's a couple of schools. One is definitely journalism question asking. JR Is it true that you knew the secret before the. That's not a question, that's an accusation. Okay, so let's. A lot of people play that game. I don't wanna play that game. There's another school of thought, though, that says you have to be so incredibly well researched, you have to be the expert and you show off your intelligence by the questions you're asking right now. You wrote a great book. I'm gonna highly recommend it. No offense to you. This is true of James Clear, another podcast alumnus. 99.9% of Planet Earth has never read Atomic Habits. They haven't read the Art of Asking Better Questions. So part of me is like, yeah, that's just a bad idea, even if you're talking to James Clear, because half or three quarters of my audience probably hasn't read his book. The other approach is what I call the Larry King approach, because I've listened to Larry King on interviewing, and he didn't do a lot of prep. I do prep, but he didn't do a lot of prep. And he's like, no, I want to be dumb. He said, I want to ask the question that the average person on Larry King Live, watching that at night on CNN back in the day, would want to ask because they barely know who Barack Obama is, or they don't know that he was an attorney beforehand. And so he's like, I want to be dumb. And I think when I do this job, well, I'm dumb. Do you want to talk about what dumb questions are and why they're so valuable? Or maybe also what the shadow side of trying to be the expert and how smart your questions are could be?

[B]

Yes, absolutely. And you're hitting on something. And Larry King was one of those question mentors that I had. Didn't know him, but just would watch him. I'd print out. Even in high school, I would print out the transcript, which CNN.com always had the next day. And I would just notice the questions that he would why did he lean in? Why did he lean back? Why was he smiling? Why was he not? And even his body language often told us the kind of questions that he was asking. So I totally agree with you on that. I do think that because questions are so powerful, we always have to ask ourselves, what is our motive? What is my motive in wanting to ask this Is it to look brilliant or funny or intelligent? Am I trying to put someone in their place? Am I trying to ask a zinger, kind of a gotcha question? Or am I really trying to learn? Am I trying to ask? Am I trying to care? I think questions with the right motive are an extension and expression of hospitality and, of course, the word hospital in the word hospitality that I can actually ask questions that bring healing. In fact, I think of Jesus's questions. Some of them were so personal, they drew blood, but not with a sword, but with a scalpel. And that scalpel of a surgeon's scalpel, of cutting open, yes, it hurts. There's pain, there's blood. But the intent is to heal. Not always. But I think a lot of Jesus's questions brought about healing and redemption. And so I think if we can be the kinds of people that see questions as hospitality, and sometimes that means being dumb, right? We elevate the guest over ourselves, which means that we take the posture of a servant even as we ask the question to other people. So, yeah, I think you're with. I think you're right on being dumb. But it requires a ton of courage and a ton of inner work, because the moment you ask a question, you're admitting I don't know the answer. And that's really hard for a lot of people in our culture today.

[A]

Yeah, I mean, I struggle with that sometimes, too. I'm a huge fan of Stephen Bartlett. He's 33, one of the biggest podcasts in the world. One of the things I've noticed, I've been listening to him for a couple of years now, is he has gotten, and I say this with the highest respect, dumber in his question asking. So if there. As his podcast has grown and it's like hockey stick growth, he has gotten better. If there's a technical term, he'll just interrupt the guest and go, what does that mean? And he probably knows half the time or three quarters of the time, but I wonder if he's asking on behalf of his audience. Because what I try to do, I have a very smart audience. They're great, but not everybody knows everything. And so if I'm willing to be dumb, if I'm willing to ask the question that everybody else is afraid to ask, I think it was a Jim Collins story. Maybe not, But Jim was, or whoever this was, was executive consultant, highly paid, got into a boardroom. Maybe it was Les McKeown. It was Jim Collins or Les McEwen or somebody in the comments will correct me. So goes into this boardroom. And like there's this fancy, you know, PowerPoint that's presented with the quarterly plan and everything. He goes, excuse me, I don't really understand it. Well, you know, as you see, da da, da, da, da. No, I'm still not getting it. No, no, no. Seven questions in everyone in the room is like, yeah, we have no idea what this means either. It was a whole bunch of just jumbled garb, you know, garbled jumbo that they threw together on a PowerPoint slide. And I think often questions are a gateway to real understanding or through cutting through the noise. I don't know, I'm kind of rambling here, so go rescue me with this.

[B]

No, no. There are so many obstacles, and one of them is the trap of expertise. It's thinking. We already know, so why would we ask any questions? But it's also on the other side of the fear of looking dumb, the fear of awkward interactions. What if I ask a question and people look at me and say, what, are you crazy? What's wrong with you? You shouldn' that by now. So there are lots of assumptions and you've just hit on a few of those that keep us culturally from asking more questions. And so, you know, I spent some time just naming those obstacles in the beginning of the book. Because if, you know, naming things as a way of taming things, naming things as a way of changing things, we just have to name what those obstacles are up front before we can get there. So that doesn't surprise me. And I bet that happens to a lot of consultants who are secure in themselves to say doesn't make any sense. Can you explain that to me? Yeah, I don't get it. And because no one else in the room has been courageous enough to ask it, it takes an outsider sometimes to come in. It's almost the. What's the fable of the kid that says the king has no clothes on?

[A]

I mean, it's, oh, yeah, the emperor's new clothes.

[B]

The emperor's new clothes. Just being able to just name, hey, I just don't get it. And everyone else is saying, well, if I can raise my hand and say, yeah, the emperor's naked.

[A]

What are some other obstacles that we would have within ourselves to asking questions?

[B]

Yeah, well, I mentioned already just living in an attention seeking age, number one. But we live in question deserts because it's not modeled well. It's also not appreciated and sometimes we're penalized. There are a lot of boardrooms where it's penalized to ask questions in our efficiency Oriented world, we celebrate efficiency and progress. Questions can be perceived as inefficient. And so why are you slowing things down? We were making so much progress here, and so that's one that can be tough to push up against. But I just think there's a general lack of curiosity. Sometimes we say, I don't really care what other people think. And the last one, I think there's a fear. There's a fear of awkwardness. Awkwardness of what the question might reveal, especially the questions we might ask of God or ourselves. There are some times I don't ask myself a question because I'm not sure I want to hear the answer. And sometimes with other people. But I also, you and I have enough emotional intelligence to know when questions might be out of bounds, might be so awkward. But when we're truly honest with ourselves, the inner work that's required takes a ton of courage to ask those questions that the answer may scare us. And so oftentimes we just push those away. But I think that's the difference in wisdom, right? I mean, the wisdom literature that exists in the Bible, that's where the most questions are. The most of the questions of the New Testament are found there. And there's a connection between wisdom and questions.

[A]

Yeah, I think you have this in the book, and if not, we can move on. But there was like Jesus only answered a very small number of questions, but he asked like lots. Do you know the math on that offhand?

[B]

Yeah. Jesus asked over 300 questions. He was asked over 180 and he only directly answered five of them.

[A]

He semi 180 to five and 300 and some odd to five.

[B]

Yeah, yeah. And sometimes people throw out 307, 325. You can't tell on going between Hebrew and Greek and English. Sometimes in our translation, some will be an exclamation point, some will be a question mark. It's often hard to tell the cultural.

[A]

For those who don't know, that wasn't there in the original. There were no punctuation marks in the original Greek. We've added this.

[B]

But what we can say is confidently. There are more than 300 that Jesus asks. He's asked over 180 directly, answers 5 indirectly. It seems he only answers 4. The rest he deflects, ignores, tells a story. And fascinating, you would think, the way the truth and the life people are asking questions. This is my chance to give answers. And a lot of it was rabbinical training of someone asks a question, you ask a question back. But wow, that blew my mind and the brilliance of Jesus's questions. We study his miracles, we study his parables, we study his healings, we study his teachings. We don't study his questions. And yet that's where the bulk of life change happened, when it was preceded by one of his questions. That's what set me on fire.

[A]

Everything from who do you say I am? Which we will preach, right? But there were so many other questions that Jesus asked. I'm curious, from an analysis standpoint, when Jesus asked a question, if I ask a good question, if you ask a good question, what does that actually do in terms of learning? What does that shift or what does it accomplish?

[B]

One of the most fascinating things that I found in my research were neuroscientists of studying the brain and brain scans. When people were given answers versus when they were asked questions. When they were given answers, their brain lit up. When they were asked questions, their brains lit up like fireworks were going off. It just totally lit up the whole brain. And one of the ways that researchers describe what happens when you ask someone a question is they said, you can temporarily hijack someone's brain. That the brain is wired automatically to say, how would I answer that? No wonder Jesus says so many times, what about you? What do you think? Right. What do you think? Is a very common question Jesus asks, and what do I think?

[A]

Right.

[B]

So it immediately makes us listeners, participants, to want to respond. And so, I mean, just to give an example of this in terms of hijacking someone's brain, you know, very temporarily, but you can do this, is if I were to ask your listeners, what color are your shoes right now, everybody, they couldn't help it. They thought, what are the color of my shoes? Some of them maybe even had to look down.

[A]

Yeah, I just did that, right?

[B]

Because I just hijacked Carrie's brain. I just hijacked the listener's brain. Because that is how our brains have been wired. Rather than me just telling you what the color of your shoes are, which would light your brain up asking you, it sends off this whole fireworks effect throughout your brain. And that idea, this is what Neil Postman says. The most important thing that we could teach kids in school how to ask better questions, we don't teach them. And he said, the best teachers are those that are constantly not just asking students questions, but giving permission in a classroom where students can ask questions of teachers and students can ask questions of other students. That's the next level of education.

[A]

Today's episode is brought to you by the Art of Leadership Academy. Hey, if this Podcast is part of your leadership rhythm. I've got something I think you're going to love. Inside the Art of Leadership Academy. You'll get exclusive access to show notes for every single episode, plus a private space to discuss each one with other church leaders. And with me, you're not going to find a whole lot of like, negative jumping in or like, hey, I can't believe you said that. Right? It's not like social media. It's social media, but better. Okay. It's like your own behind the scenes breakdown of every episode with real time conversations on how to put into practice what you're learning. And here's what makes it even better. It's completely free to join. You'll also get first access to the upcoming seven disruptive church trends that will rule 2026 team leader guide. I do that every year. You'll be the first to see it, along with interactive live streams and a podcast series that goes with it. So getting started takes less than 60 seconds. And when you're in, you'll instantly be part of a life giving community. No noise, no spam, just a group of church leaders helping you grow faster and lead more effectively. So click the link in the description of this episode or go to theartofleadershipacademy.com just a few clicks and you'll be in. Look forward to seeing you inside. You know, it makes me think about preaching too, because we love to tell people what to think. This is exactly what you should think on this issue because these guys have it wrong and these guys have it wrong, but I've got it right. And here it is. Here's the truth served up for you. Easy to go. How would you weave better question asking into your public communication? Into your preaching, for example?

[B]

Yeah, I'll back up a little bit here and say one of the things I did as I was studying Jesus questions was the pedagogy of Jesus too. How did Jesus teach? And I realized he took his listeners on three different field trips. He took them on physical field trips where he, you know, peripatetic. You know, he's walking around, look at the birds of the air. Look at the lilies of the field. Look at the woman putting two mites in the temple treasury and turns it into trips.

[A]

Yeah, that wasn't, that was like, we think of it as like academic, but he was like, see the birds? Like they're right there, right there. And the widow, she's right there.

[B]

Yes. Almost like as if he's pointing or nodding or gesturing. So literal field Trips, number one. Number two, emotional field trips using stories and parables. Right. And then, of course, mental field trips by employing questions to provoke thought and participation. And so what do we do? Oftentimes in preaching, we sit people in the same room. We have them sit in a seat passively. We don't tell stories. We often just give abstract ideas. And instead of asking questions, we give information. And then we sit around and wonder, why is no one changing? Well, maybe we should try to teach like Jesus did. Now there, of course, we need answers. And Jesus didn't just use questions. I mean, he gave answers, of course. But that has shaped the way I think about preaching. I also think about Paul. I mean, look at the book of Romans, how he utilized questions. He was constantly asking these rhetorical questions as a way of setting it up. So he'd say, should we sin so that grace shall abound even more? Absolutely not. And then he answers it. So I think good preachers. Tim Keller did this really well. And I know you had Matt Smethurst on to talk about Tim Keller recently. Tim would often ask a question and then he would let it hang in the air for a little bit because he was hijacking their brains. What do I think about this? And then he would give an answer to that. I think Paul did that beautifully in the book of Romans, many of his letters, but especially Romans, and for that rhetorical effect. So I think that is a great tool as an opener. One of my favorite things when I'm preaching is just to ask one of those questions that's thoughtful, engaging, jolting, just grabs someone right around the neck and won't let go. Right from the start, not, hi, good morning. Just launch into a question and then just put it boldly up on the slide on the screen.

[A]

That's funny. Last time I preached, I did exactly that. I opened with a question. Interesting.

[B]

Yeah. Because what does it do? It hijacks people and they're locked in and ready to go. And I think we can utilize that from.

[A]

Listen to me to what did you bring to this? Like, what is going on in your life? I am actually very interested in you. And once you establish your set point, we're going to go on a journey together. And hopefully it's a little bit better at the end. Yes, interesting.

[B]

Again, it can depend also on the size of the congregation. This would be harder in a several thousand member church, but for smaller churches, the opportunity for some interaction and dialogue. I've seen smaller churches do this really well of a leaving five or 10 minutes at the End. And this can be risky in terms of open mic sometimes, but of saying, where do you sense you've heard from the Holy Spirit? And how might you respond to the teaching this morning? And it's led to some beautiful times. You could even do that with, you know, sort of some, some pastors do that during the Sunday school hour of, hey, we're going to have a talk back time to just allow some time for conversation and questions. You can do that with small group questions. I think there are a lot of ways we can utilize that. I think pastors utilize it. I think we can take it to the next level or two as a way of engaging with our congregation. I've seen some pastors even switch it to say, hey, we're going to be preaching on this topic next week. So between now and Wednesday at noon, I want to encourage you to read the passage and submit any questions you have about the passage and for the pastor to go, huh, I never thought about that. Maybe I need to address that. So it's actually asking them to participate before the sermon by submitting their questions.

[A]

One of the things I love about this podcast is a lot of the listenership is young. A lot of young leaders, Gen Z, younger millennials, Millennials who are stepping into leadership or getting ready for it. And my interaction with them is they are decent. A lot of them are decent at asking questions. If you had to give advice to the next generation of leaders about the questions they should be asking, how to ask questions, where would you start? What would you tell them?

[B]

The most important thing I would say in two words, be aware. I think the first thing, we just have to be aware of several things when it comes to our questions, like just being aware. How many questions am I asking? Am I asking questions first of all? If so, what were they? Were they thoughtless questions? Were they thoughtful? There is a principle, a universal principle of question asking that goes like this. If I ask a generic, unthoughtful question, I will often get a generic, unthoughtful answer. How you doing? Fine. How was your day? Good. But if I can ask a thoughtful, engaging question, more often than not, I will get a thoughtful, engaging answer. It's as predictable as a communist election. I mean, it is just so interesting when you are just more specific and more thoughtful, how the conversation becomes richer. So I would just encourage folks to think about being aware in four areas. Number one is content. Right. What am I asking? Number two is quality. Just because I asked it doesn't mean it's good. Three is frequency. How often am I asking questions? And then direction. Are the directional arrows pointing inward? They're about me, or are they pointing outward toward other people? And I think just a quick evaluation of that, you know, content quality, frequency and direction of my questions can really help, of just that awareness. That's a great place to start. You can't change what you aren't aware of and what you can't name first. So that's what I'd encourage anybody, young or old, is just be aware.

[A]

Can you give us a set of examples of some bad questions and then some better questions, like questions that kind of go nowhere or get asked all the time that aren't particularly helpful versus questions that are actually helpful.

[B]

Let's name the obvious ones, the ones that are hurtful, vindictive. Who are you?

[A]

Who do you think you are?

[B]

What's wrong with you? And there are a lot of counselors, couches full of people who years ago had a loved one, asked them either once or repeatedly, a question that was incredibly hurtful. So let's just get that out of the way. Let's avoid those at all costs. But I think that we can ask what I'll call benevolent but useless questions. They would be like, what's up? How are you? How are you doing? Now, I know sometimes those are just greetings. Like when you say two dudes pass each other, what's up? You know, that's kind of a howdy. Yeah, yeah. But if we can go to the next level, instead of how's your day? What if we just tweaked it just a little bit? 10 or 15%, more intentionality, like, so what's been the most interesting part of your day so far? Or instead of where do you live? What's the most interesting part of where you live? Yeah, what. What are two or three adjectives you'd use to describe how your day is going so far or this season, or how your family's doing? It's a little bit more thoughtful, a little bit more specific on that. One of my favorites, my dad likes to ask, he'll say, today, are you winning or losing? And people go by what metric? You tell me. It's just a fascinating way to see how are people evaluating their day? And so if there's any way to. I'm not going to say that all closed questions are bad, but when it comes to connecting with people to say, how can I make this as impossible, nearly impossible to ask a question where they can only give me one word answers. So I do this with my kids Picking them up at school, you know, when they were younger, instead of saying, what do parents say? How was your day?

[A]

How was your day? It was good.

[B]

It was fine.

[A]

I have boys.

[B]

Yeah, right. Yeah. We have two sons as well. And so. But instead I would say, so what did you learn today? You didn't know when you woke up this morning? It's just another way of asking, or, where did you find joy? Where did you laugh today? Did you have fun with your friends? Or what was the most interesting part of your day? It could be lunch, it could be recess, could be practice after school, or it could be, well, we learned something really interesting in history I didn't know about. Well, that's way better than how was your day? Good. And then we're just trying to pull teeth as parents. So I'm trying to play that game without my boys knowing it when they were younger. Can I ask a question that it is impossible for them to answer with just one word?

[A]

So that's been a rule that I've had for myself for this podcast, I think, pretty much since the outset. And I made mistakes, you know, but it would be like, so was writing the book Easy jr, Right. Would that. That set you up for yes or no?

[B]

Right, right. That's leading questions.

[A]

Or do you enjoy leadership? Yes or no. Right, right. What is the problem with that? And then you've given us some examples. But, like, I just want people to understand what's at stake when you ask a question that can be answered yes, no, or, you know, that kind of binary short answer.

[B]

Yeah, yeah. The binary short answer of yes, no, or the aperture sometimes is so small, we're boxing people in. We don't really know it, but we're doing them a disservice by, you know, sometimes it's maybe they say, well, leadership is good and bad. Well, what do you mean? Well, I haven't given them that option to be able to talk about that. So I want to open up the aperture and let them decide which direction they take it. Do they want to take it real personal? Do they want to take it on a. On a macro level? But if I just corner them into sort of a yes, no answer, that can be difficult. You mentioned leading questions, I think, and there's a differentiation. Sometimes we need to differentiate between leading questions and guiding questions. I think guiding questions are great of leading, you know, guiding people in a direction to be able to have them expound upon something we may know about them. But a leading question is, if you disagree with me, then you're you're ostracized a little bit. So. Yeah, yeah, exactly. And so that we see that often with athletes, you know, who are being interviewed at the locker room, you know, at their locker after a game. Right. You know, like, oh, I want.

[A]

That's one of my secret jobs, wasn't it?

[B]

You know?

[A]

Yeah, that's right. How did, how did it feel when you hit the grand slam, walk off home run? Well, yeah. What do you think it felt? What do you. What do you mean? Like, I want to. I want to. Actually, I was watch. I'm watching the World Series right now, so this dates it. Okay. It's going to air a couple months later, but I'm like, can I, can I do those on the field interviews? Because I bet you I can come up with better questions.

[B]

You know what? My father and I have talked about that many times and have actually come up with a list of questions that we would love to see asked of both. Okay, let's go there.

[A]

What's a couple of those questions? Because everyone's seen it and I'm like, you know, so what are they?

[B]

Yeah, well, I mean, I don't think the ncaa, this is college football or college basketball. I don't think they would allow it. But to say you're called a. A student athlete, what did you learn this week in your classes that was exciting? Now, I don't think they would allow.

[A]

That because you're going to bust the whole system, junior.

[B]

That's one. But also saying you're obviously at the height right now after that winning touchdown or that home run you hit. What were some lies you were tempted to believe during that 0 for 21 stretch that you had a couple months ago?

[A]

Ooh, that's a good question.

[B]

You've gone through some low points in your life and in your career. What does that feel like? The juxtaposition when it was so low you wondered if you would continue if you might retire early, and then now this. What does that gap feel like? When were you tempted to quit? And how does what you feel now, does it make it all worth it? Those are the kind of questions, not just the successes, but reflecting on the successes, but thinking back to when this wasn't happening, what was that like? So the human side of it, even things like, who's the first person you're going to call when you get back to your locker?

[A]

That's great.

[B]

I just would love to know, who are they going to call to celebrate that with? Their dad, their wife, their girlfriend, their friends? I think the human Side of interviewing athletes, I think we could do a little bit of better job.

[A]

So lots of young leaders are getting around, people that they have respected, whether that's someone who wrote a book, a favorite preacher. They're at a conference, they meet their hero in the hallway, and they get three minutes with said hero. What are some do's and don'ts in terms of question asking in a moment like that?

[B]

Yeah, great question. If you've got three minutes. I think the first thing is to ask for permission. I think sometimes we just assume I've got them and I can ask a question. I think just right, I've got them now.

[A]

We can't go anywhere.

[B]

If we teach or preach or speak somewhere and we get off a stage, sometimes we just need a break. We're not trying to be mean, we just, we're depleted. And so just to have somebody say, would it be okay if I asked you a question or two for the next two or three minutes? Questions I've been wanting to ask you for a while. I just appreciate it when people have extended that courtesy to me and I think others have appreciated it when I have extended it to them. I also would encourage, whether it's their hero or just anyone else, any meeting, any situation they're going into, any conversation, always come prepared to ask two or three questions. You may not ever ask them. But just the exercise and the practice of forcing yourself to think through just a few engaging questions before you get there is a wonderful exercise. But there are times where I've met with some people that said, I've got 10 minutes, I can give you 10 minutes. And I played a game with myself to say, can I ask them questions that they would say? I've never been asked that before. Ooh, that's really good. I remember meeting with a college president once. I had 10 minutes with him and the knock at the door came at the 10 minute mark from his assistant. And his assistant poked her head in and said, you know, I'm sorry, time's up. And he waved her off and said, you know, it's fine, it worked.

[A]

Those are the best.

[B]

I know. And I had another hour with this person simply because I was asking better questions. But I came in prepared. I spent a lot of time thinking ahead of time. So I would encourage anybody, especially young leaders. And I like to ask this question, sort of a party conversation, you know, who would you like to have dinner with? We sort of ask that. But the follow up is, when you're at dinner, what are the two or three or five Questions or topics you'd want to talk to that person about if you had the chance, that becomes an even more interesting conversation at that point.

[A]

So take that university president, college president or hero. And you're not the first person on this show guest to say that they have prepared a list of questions. And I've done the same thing. There are dream guests I've got for the show. Some of them I have files started of if I ever get a chance to talk to, I am going to ask him or her xyz, how do you go about formulating interesting, provocative questions that make college presidents wave off his assistant and say, no, it's okay, I don't need to limit this because we.

[B]

Live in spaces and in time where there are conversation and question deserts. If you show interest and ask some thoughtful questions, it is like water for a parched soul. I mean, people love being asked questions. And if you can ask questions that aren't predictable or vanilla or worn out. And I try to play a game with myself and I talk about this at the end of the book. I try to play a game with myself that says, can I get them to say, huh? That's a really good question. Huh. I've never been asked that before. Huh. Can you give me a minute? I need to think about that. I think if you can get a few people responding that way, that's where people say, wow. They wouldn't necessarily articulate this, but they'll say, you're giving me a gift. Oh, you really know. I'm really thinking in some new ways. Wow, I feel seen. And so it'd be less about the types of questions and more about wanting them to feel loved, cared for, seen, thinking in a new way. One of my favorite questions to ask people is what is the question that people either don't ask you or don't ask you very often that you wish they did. It'll tell you a lot about who they are.

[A]

I've gotten into a habit of asking that question from time to time on this show, particularly if it's a well known guest. Right. I'll give you an example of and let's just do this and then I'm going to flip the mic because you had said this when we were setting up this interview. It's like, hey, if I get a chance to ask you some questions, I'm like, okay. And then you mention it again today. But like James Clear, who I mentioned already, very hard to get an interview. He only does a few a year and we got him on the show. Same with Jim Collins. And yeah, I'll use those two as a case study. So with Jim Collins, it was a year. Took us a year to get a yes. And it was very gentle connections and his whole team was amazing. But one of the things that happened was I happened to be interested in something that he was really interested in but never gets asked about. And that just happened to be his favorite book, which is how the Mighty Fall. So they were like, okay, Jim might be open to this. If you were to get an interview with him, what would you want to ask him about? And I'm like, okay, I'm going to go for Bro Cure. Because everyone's going to say good to great. Everyone's going to say built to last. I'm going to tell him what I really think. I really like how the Mighty Fall. So I put that in the email to his team and I'm like, okay, this could be it. This is the nail in the coffin. But they're like, turns out that's Jim's favorite book. He never gets a chance to talk about it and wishes it saw more daylight. So that really helped with James Clear. And I bumped into him once at an event after I interviewed him, and he remembered the interview. But when we hung up the mic, you can listen to it, we'll link to it in the show notes. He said, that was fascinating. He says, everybody asked me about habit making. Nobody asked me about the making of James Clear, the blog, building an email list, how I wrote the book, how I marketed the book. He said, that was just refreshing. And what I'm getting from a lot of these well known people is they're doing the FAQs over and over and over again. Right? It's the same 10 questions. And so when I've had a moment like that, it makes me feel like I won as an interviewer. Like, all right, I did something that was interesting to the guest as opposed to, oh, yeah, this is interview number 75 on this book. And same question. So any comments on that or learnings that you have and feel free to dissect the case study and suggest other ways that might be better.

[B]

No, I love that, Carrie, because what you're doing is you're giving people a gift to go in new directions, especially those two guests. I listened to both of those interviews that you had. They were both fantastic. And you could tell by their tone of voice that they were really enjoying that. That's true.

[A]

If the guest is bored, you pick.

[B]

It up, you pick it up. You can hear it in their voice. And so you do a really good job with that in terms of the preparation and asking things that they want to be asked, like James Clear told you. And that's a beautiful gift. You gave both of them a gift. But I know you do that in numerous ways, even when not on a podcast, just when you're with people. I'm sure that's who you are. And so, yeah, that's if, you know, it's the whole, like, Carnegie, you know, don't try to be interesting. Try to be interested. If we can learn to be interested in other people, it's amazing what can happen. And we get waved off, you know, by the university president to have more.

[A]

Time, how to win friends and influence people. I resisted that book for most of my life. I think I read it in my 40s. Maybe it was my early 50s. And I'm like, no wonder this thing is selling 100 years. Yeah, it's so good. And same with. He's got a story about the CEO that the sales guy could never get in to see. And after a year of hammering down the door with the assistant, he finally got a minute. He got one minute with the CEO, and he walked in and he saw this trophy fish on the wall. And he goes, you like fishing? And that was it. Because his whole family was sick to death of hearing all of his fishing stories, and his staff didn't want to hear him. Suddenly, he had two hours for this guy to tell him all these fishing stories and then said, oh, yeah, why were you here in the first place? Yeah, I'll take a hundred of those, right?

[B]

Absolutely.

[A]

Because he was interested. It's like such a classic thing that we have forgotten.

[B]

Yep. And that's the arrows out versus the arrows in. You know, like, can we really focus on what other people are doing? Can we serve them? Can we do them a favor and bless them by saying, tell me more. Tell me your story, your hopes, your dreams, your passions, your fears. It's amazing what happens.

[A]

So are you ready to flip the mic?

[B]

Let's do it.

[A]

I don't know why I'm a little apprehensive. Because you wrote a book on question asking. Now I'm going to be interrogated.

[B]

Okay, let's slap the reverse uno card down on the table here. All right. Okay, so let me start by saying, like, as I mentioned, a longtime podcast listener, you really do ask great questions. So the first one is. And I think it's because of your preparation, your curiosity, but what are the other. How did you get so good at asking Great questions.

[A]

You know, it probably goes back to my burnout, which you referenced. And one of the learnings out of that season was I found myself getting really cynical. And it was a problem. Like, I think burnout and cynicism are almost like they coexist. And I thought, gosh, like I was in my. I was 41 when I burned out. And I thought, if this is the rest of life, this is drudgery. And so I started researching, how do you combat cynicism? And there's not a whole lot of books on cynicism. I'm gonna write one one day. But when I was doing the research for my second to last book, didn't see it coming. I really puzzled through it and I thought, you know, what's interesting and correlative is you never see cynical people who are curious. They always have the answers. They're like, here's why this doesn't work. Or let me tell you, when I was young, blah, blah, blah, blah, blah. But people who are curious are never cynical. And I thought, okay, the good news is I can't change my disposition, but curiosity is a skill that can be learned. And so I'm like, I am gonna be the question answer asker. And it was one of those things, I think I wrote about this as at some point, but it was like I was flipping through the channels one day I came across PBS. I see this 80 year old professor, he's got the tweed jacket, the bow tie, sitting up straight, being interviewed. And I think I was recovering from burnout at the time. And all I remember from the interview is he said, well, what we are now learning is. And it just hit me, it's like, dude, you're 80, what are you doing? Still learning. And then I thought, that's, that's the key. And so I've made it a discipline for almost 20 years to be the asker, to stay curious. And there are seasons where I'm good at it, seasons where I'm not good at it. You have a bad day, you're kind of like, bleh. But on my good days and when I'm disciplined and prepped, it's like the. Well, your book is called the Art of Asking Better Questions. But I want to learn what is the art of asking a good question. So staying curious honestly is a personal discipline for me that keeps cynicism at bay. Because even if you kind of roll your eyes, it's like, well, okay, but if I ask some questions, I would learn that that person has a perfectly good reason for Believing what they're believing and they're not stupid. Even though in my head I think they're stupid, they're probably not. And maybe if I got a little more curious, I would understand. So that's where it comes from.

[B]

Yeah. Yeah, that's great. So let me follow up with that and say if you. And you're great at questions, if you were to grow in your ability to ask questions by like 10 or 15%, how might you go about growing in that ability?

[A]

Ooh, that is a good question. See, you did it. Congratulations. I think I would have to become a deeper student of the art of asking questions because I think your natural aptitude and curiosity gets you so far. So some of what I do is I listen to different podcasts often. Not outside. I hope this isn't heresy. I don't listen to a ton of Christian podcasts because I find that Christians are not the best question askers. We are answer givers. And I really love the curiosity on a lot of other podcasts. One of the reasons I bought your book is it's got an appendix of excellent, excellent questions in it. And so I wanted to have that handy so that I kind of go through and have a resource for questions. And I think, you know, it's okay. It's something else you mentioned early on that I was going to flag, and I didn't. But you mentioned your code word with your wife about waitress, and you said something that's really interesting. That is a test that I have used now probably for 20 years or longer, which is what I call the meal test. I don't think I've ever written about it or talked about it, but I became aware because I'm married to a wonderful woman that I can talk forever. And she'd be like, you dominated that conversation. And she's not wrong. And so what I do. How quickly people eat at a social dinner is an indicator of how much they've talked and how much you've talked. And if I'm at a place where I've eaten the entire meal and the other person hasn't taken a bite of their salad, chances are they've done all the talking and I haven't. And so what I try to do is I will actually pace my eating and look around, and if I see.

[B]

That.

[A]

I haven't touched anything and they're almost done, I have dominated the conversation. So I use little tests like that, try to listen widely, and I would become a better student of the art of the interview. Oprah Winfrey, by the way is a.

[B]

Great interview, amazing interview. What do you think she does? What is it that she's doing that makes people say, I've never told anybody this? And there are millions of people listening, hearing something for the first time. What is she doing that makes her brilliant?

[A]

I don't know for sure. I listened to there's a great podcast, I think it's still out there called the Making of Oprah that I listened to years and years ago, which is amazing. I think people trust her. And I hear a very I'm kind of importing my experience on Oprah. So if there's any Oprah students out there, feel free to correct me. But one of the reasons, because I hear that quite a bit, I'll have well known people on here who have said, I've never talked about this before or are even wondering, wow, should we let that air? Like, that was very vulnerable. And I think the reason is they trust me and they know I'm not out to get them. I'm not the journalist person who wants to see them canceled. And I think Oprah's been very vulnerable about her life as well. Very open, everything from her relationships to her weight loss battle to all the things she struggled with. And people admire your strengths, but they identify your weaknesses, identify with your weaknesses. Like, they really empathize with them. So I think I've been pretty transparent. I think people know, like, I want guests to want to come back, and the moment that I do a gotcha interview, they don't want to come back. And I think Oprah's the same way, that she'll have some really candid moments. But it's one thing. There's a Larry King story that's fascinating. I may have told this before on the podcast. I'll give the abbreviated version and you might know it. J.R. where he was starting in radio, I think it was in Miami when he was really young and he got a show and he had somehow gotten to know Jackie Gleason and did something good for Jackie Gleason. Do you know this story?

[B]

I don't, but oh, yeah.

[A]

So he got to know Jackie Gleason, and Gleason owed him a favor of some kind. So he's trying to make his name in radio before he was the Larry King that we all know, and he was just at a local radio station and Frank Sinatra was in town, and he knew that Gleason and Sinatra were best friends. So he called up Gleason and said, I need Frank Sinatra on my program. And Gleason said, done well, Frank Sinatra's PR guys were like, really livid. Who's this stupid kid nobody's ever heard of? Frank Sinatra doesn't have time for this. But Sinatra showed up at the radio station and was willing to give him two hours for the interview. Wow. So Larry King starts doing the. As he's preparing for the interview, Sinatra's guy comes up to him and says, hey, whatever you do, don't talk to him about his child. You are not allowed to do that. And Sinatra apparently had a child who was kidnapped and very sensitive topic, not allowed to talk about it. So Larry King's like, okay, that's fine. So they're about an hour, hour and a half into the interview, and Larry knows he can't ask the question, so instead he just asked him, Frank. Mr. Sinatra, have you ever felt like the press gave you a really bum rap? And he goes, actually, yeah. For example, when my son was kidnapped. And then he goes on and tells the story, right? Had he framed it? And I've thought about that because I have some very high profile people. I'll just ask him questions like, how did that make you feel? Or do you ever get emotional or you ever feel like quitting? And it's not a loaded question, but they will then open up if you have that trust. And I think Oprah has that gift.

[B]

Yeah, I think you're right. I think you're right. I'm curious too. If you're willing to go there and if you aren't, it's okay. But what do you sense people get wrong about you? Like, where are you often misunderstood?

[A]

One area I hear about regularly is I don't use much scripture in my work and in my writing. And I mean, back in the day when blogs had comments, we'd get trounced on that all the time. And I'm sure they're on YouTube. I don't spend a lot of time in the comments these days. I think the reason I don't do that, it's not that I'm not a Christian. It's not that I don't care about scripture. I care about scripture very much. But most of the things that I'm commenting on on this podcast, on my YouTube channel, on my other stuff, is the stuff that isn't specifically in the scripture. The business card of what I do these days is I went to law school, but nobody taught me how to run a law firm, and I went to seminary and nobody taught me how to run a church. So I'm trying to fill in the gaps of what leaders have to learn on their own the hard way, try to give them the cheat code. And the other thing I'm very, very sensitive to is people have misused and abused scripture so often that if I have an opinion about, you know, your church governance, or I have an opinion on how you should hire fire staff, or I have an opinion on how to reach unchurched people, but that's all it is, an opinion. I don't want to use scripture as a muscle flex about an opinion that honestly could be wrong. And so that's one thing I hear. Another thing, probably criticism I hear, is that I won't weigh in on politics expressly. I do. I just do it in a way that doesn't use the trigger words that either are things that the right or the left want to hear or things that they despise. So I'm working really hard on making a contribution in certain areas, sometimes by not making a contribution, sometimes by just trying to say things in a way that avoids stepping on the landmines that blow up a lot of our feeds these days. And yeah, those are two. I mean, do you see anything that you would say, I think people think this about you, but I'm not sure.

[B]

It'S true about me personally.

[A]

Well. Or about you, whatever.

[B]

Yeah, I don't. But I really appreciate your vulnerability to be able to share where you're at with that. And I think it shows some good self awareness as well. I'm curious, you know, you just had a recently put out a preaching course. I'm curious, as we talk about preaching and question asking, if we took Jesus's posture and priority of how he asked questions, how do you think that would impact preaching and how people would receive preaching Very positively.

[A]

I did an interview with Adam Grant where we talked about sort of the approach of preaching that I try to have. And basically because I had the, you know, good fortune to be trained in cross examination at law school, all cross examination is really is anticipating the questions and objections of everybody at play. What is the other side going to say? What does a judge need? What is a judge going to ask? What does a case law require? And I approach a talk or a sermon very similarly, where I'm, I'm trying very hard to think, okay, I'm going to say this is what the Bible says, this is what Jesus taught, this is what Paul argued in Romans. But what are the real world questions and objections that are going to come up? And then I'll try to list those questions and objections. And sometimes, and Keller did This masterfully, too. You'll raise them. You'll say, I'm just trying to pick an issue. Romans 7, classic text about, I don't know why I do what I do. Paul, we get a. You know, it's almost like a page from his diary just got dropped into the scriptures. Of course, that isn't what happened, but, you know, it's like you could ask questions. You ever feel like you're a fraud? You ever feel like you have imposter syndrome? Not so much at work, but in terms of, like, your Christian faith, Like, you're like, okay, I'm never going to do that again. And then you do it. Well, you know what? You're not alone. And so there's a series of questions that draws people in. And then the surprise is, oh, the guy who wrote two thirds in the New Testament also struggled with the same stuff. And this appears to be in the present tense. This isn't pre conversion, from what we can tell.

[B]

Huh?

[A]

What do we do with that? Right? So it's a series of questions where you're almost looking at the text and then you're like, oh, if that's Paul, what does that mean? Is this whole thing a fraud? I love that. That's a technique. Fred Craddock, Emory University, used to teach this. He'd say, state the problem and then make the problem worse. And if you're doing that really well, through a series of questions and assertions, you can get yourself into a place where everyone says, oh, now you're screwed. You've deconstructed your faith in the pulpit and there's no getting out of this. And then, of course, boom, you turn the corner and you get out of it by sharing, well, what's really going on. But at that point, you've got people engaged with a series of questions. Another thing Andy Stanley does very, very well, it's sort of, pardon the metaphor, but a bit of a shotgun approach. So you got to think, what is this like for the single mom, for the married person, for the divorced person, for the empty nester, for the new parent, for the single person, right? And so you'll go through a number of scenarios, either by question asking or by just saying, and if you're single, maybe this feels like this. I don't know, does it feel like that? And if you're divorced, maybe it feels like this. And so you end up in a place where you've kind of gone through who's There and you're thinking about that. Similarly, with this podcast, I think about the pastor, 85% of churches are 200 people or less. So I try to, if we're, you know, talking to a megachurch pastor, try to make sure that we figure this out so it works for everybody. But I also realize that a lot of the most influential pastors who lead the largest churches in America listen to the show as well. So I'm trying to do both and trying to ask questions on behalf of my audience of that. So I just love questions. And I think if we did more of that, rather than put our glasses at the end of the nose and say, well, I'm gonna tell you today exactly what you should believe on an issue, we would have more engagement. And as you say, I love that phrase, questions hijack the brain. So if we ask more. And it's very effective to finish a sermon with a question, too. The way I wrapped up on Sunday was. So I want to finish with the question that I started with. How are you really? And I hope the next time we.

[B]

Meet, from the beginning to the end.

[A]

Yeah, yeah. It's like an inclusio, right? That literary device. So how are you really? For real? Real, real. And I hope the next time we talk, it's a different answer.

[B]

Yeah. That's wonderful, Carrie. Jonah is my favorite book of the Old Testament. Right.

[A]

Just 48 verses.

[B]

Right. Everybody changes in the book of Jonah except one person, Jonah. Right. But what we miss oftentimes is the last verse is a question. It's a cliffhanger. Right. So should I not care? These people that don't know their left hand from their right, should I not care? And then it says in some translations, and even the cattle, boom, it's over. And what I love about how that's structured is that wasn't just God to Jonah. We, as listeners, our brains have been hijacked at the end of the book going, ooh, should God not be gracious to people that I don't think deserve grace? All of a sudden, it's a cliffhanger. Yeah. How will we respond? Right. And in some ways, that's Jesus's model, like the prodigal son. Right. We don't know what the son did. Did he stay outside, or did the older brother go inside? You know, did he? And so I think those cliffhanger events, we can use those well with questions in our preaching as well. So can I ask you two more questions? Would that be okay? I don't want to take too much time, but I'm loving hearing about this, so I'm curious. So the podcast, what's your dream for it five years from now?

[A]

You know, that's a great question. It's exceeded every expectation I ever had of it. My dream is to. And this is like, I love Seth Godin's definition of money in a company. And this is true for a church, right? Because we can idolize it or we can villainize it. He says profit is just permission to do this again tomorrow. And I love that definition. It's like if you have a positive bank balance, it's just permission to do this again tomorrow. And I would love to continue to curate conversations with the most interesting people that I can find or that I know, because I know that conversation's been life giving. One of the reasons I started this is 30 years ago. I didn't have access to any of these guests really. And I was always interested. If you could really sit down and have a candid conversation with this person, what would they say? And then I started speaking at conferences and events and I would meet people in the green room and I'd actually have a conversation. And sometimes they'd be great conversations. I'm like, I wish everybody could hear it. So that MO. That modus operandi hasn't changed in 11 years. I don't see it changing. Like, as long as there are people, I think conversations are going to be interesting. And as long as they're interesting people. And so I want to bring, on behalf of the church and on behalf of my audience, the best conversations I possibly can. And this never gets old. I don't know why it hasn't gotten old in 11 years. Lots of things have gotten old in my life. This has not gotten old. So I'm probably gonna keep doing it indefinitely. And I would love to interview really interesting people, some well known, some unknown, and bring that to my audience. So it's kind of like an infinite game. It's like there's no finish line, there's no win, there's no, like, oh, great, you know, maybe we can level up. But it's an infinite game.

[B]

Yeah, great. Fantastic. Last one for you here. So you've been doing this podcast for 11 years. How are you different? And you touched on this a little bit, but how are you different because of the guests you've interacted with? And are there a few guests that have impacted you maybe more than others or formed you in who you are, how you think over the last 11 years?

[A]

Well, a good number have become friends. And that's like a wonderful, wonderful thing. Like people that you thought, oh, wonderful ever land this person have become friends. So I've developed some really good, close personal friendships out of this. And not everybody. We've had, like, hundreds and hundreds of guests, but there's been a handful of really meaningful friendships and a lot of people that are just friendly whenever we see each other. You know, Craig Groeschel often, he's pretty much on this podcast every year, has become a really good friend. We text or voice chat pretty much every week, see each other a few times a year, and that's been really good. He's been very influential on my life just because I think his judgment is so solid. I think he's wise beyond what people even understand from the public platform. Seth Godin, Very, very influential in my thinking. I mean, he just dropped stuff that something he had in his last couple of books about status and affiliation. Just everything's about status, Everything's about affiliation. And when you put that filter on everything, including Church World, it's terrifying and fascinating at the same time. So those are a couple. And I've just really enjoyed the friendship, the connection, the ideas. You know, I wrote to another guest, I don't want to name it, but he came on and I think it was. He's got like, four podcasts going, and one of the top thinkers in the world. I happen to have his personal email. We haven't connected since he was on the show, but it was an easy ask to say, hey, do you want to come back? And, you know, we had a really meaningful personal interaction. So that kind of, like, that's still a dream to me. Like, how did this become my life? How do I get to do this? And I'm really blown away. Like, it's kind of cool. And by naming two, I'm excluding 20 or 30 others, but that would be an example of what it's brought. And I'm just really grateful for that. So selfishly, that is good for my life, but I hope it's also good for my audience and being able to have that kind of access to some of the top thinkers in the world today.

[B]

Yeah. Well, thanks for sharing and thank you for letting me switch the table or turn the tables here and slap down that reverse uno card. So, yeah, I learned a lot, and I'm sure your listeners did as well, so.

[A]

Well, I gotta tell you, I get accused of breaking book budgets all the time, so I want to apologize one more time to my audience. Highly recommend you pick up a copy. Maybe, you know, it's almost the new year, so you can get it in next year's budget. Okay. But it's called the Art of Asking Better Questions, Pursuing stronger relationships, healthier leadership, and deeper faith. J.R. briggs is the author. It's available everywhere. I've got a copy from my library. And the reason I'm kind of harping on this, not to break people's book budget, but just to say I think we would be better human beings. And I think in this age of AI, which is my latest project, human connections are more important than ever. And asking questions, great questions, that really elicit the image of God, and God's activity in other people's lives is going to become even more important. And it is in danger of being a lost art. You could have called it the lost art of asking better questions. Did you think we toyed with that? There's a yes, no answer. Okay, so bad question.

[B]

No, we toyed with that, and it was a little harder than we thought. Originally we thought questionable influence, but then we thought maybe people wouldn't understand the double entendre there. So, yeah, if we decided to just keep it with what it is, the Art of Asking Better Questions. Well, what does.

[A]

Leaders who refuse to ask questions will end up doing questionable things.

[B]

Yes. Yes.

[A]

Sorry, John, if I mangled. That's another guy, too, that I've really gotten to know very, very well over the last 10 years, and so grateful for that. So this is a real joy for me, and it's been a joy. Thanks for the book, thanks for your work, and thanks for the conversations today.

[B]

J.R. well, thanks so much, and you've been very kind and, yeah, really grateful for this opportunity. Thanks, Gary.

[A]

Hope you enjoyed that conversation about questions. And you know what? I always want to get better at asking questions, and a lot of it is silence, but it's also curiosity, and it's coming up with better questions than the standard questions. So that was a lot of fun. I would highly recommend you get his book, because I've got it now and it's got an appendix full of questions you can ask. So let's all get better at that. We'll just have more fun in life. Hey, next episode, I've got Dominic Russo coming up. And a lot of you, Dominic will be new to you, but we're talking about what happens when you're not yet ready for revival, what happens if you're in a very secular area, and I know a lot of you are as leaders. So new kind of secularism reaching unreachable people and more. That's coming up on the podcast, Show Notes and Everything Podcast, the new home for that. This year is the Art of Leadership Academy. Join over 14,000 [e-mail] you can join for free today. Also coming up on the podcast Sharon Hoddie Miller, David Ashcraft, David Kinnaman, Luke LeFever and Daniel McLeod, John Mark Comer, Les McEwen, Henry Cloud, John Crist, Pat Lencioni, and a whole lot more. If this conversation was helpful, leave a review or comment wherever you're listening and don't forget to share it with a friend. I hope our time together today helped you identify and break a growth barrier you're facing. Hey leaders, before we go today, if you want to expand your thinking, grow your leadership, and get some really relevant, fascinating, curious content about ministry, the future, church, and other random topics I find helpful as a church leader, check out my newsletter, on the Rise. It's my once per week Friday newsletter that gets sent directly to your inbox every single week and it's totally free. If you want to start receiving on the Rise along with over 100,000 other leaders every single week, visit ontherisenewsletter.com for free. You can sign up today. So when you sign up, I'll send you a sample newsletter right away. You can get an instant taste of what it's like. If it isn't for you, you can unsubscribe at any time. That's ontherisenewsletter.com to get curated content about ministry, culture, the future, and more. One of my favorite things to do every week. I don't want you to miss it.