Dr. J.R. Briggs has spent years in various pastoral roles in churches of all different sizes. Yet his entire career can be summed up in one clear calling: to guide, equip and come alongside Christian leaders who desperately desire to build up God’s kingdom. He founded Kairos Partnerships for this purpose, strengthening leaders through one-on-one and team coaching, consulting and speaking. His favorite thing to teach is how to ask better, more insightful questions, which he believes can radically alter the trajectory of a person’s life. His latest book, The Art of Asking Better Questions, explores this topic in depth, offering readers practical advice for cultivating wisdom and connection.

In today’s interview, J.R. shares how his favorite Philadelphia cafe takes him back to his childhood home in Puerto Rico, how swimming unlocks his creativity, and the top three books that have transformed his leadership style and relationship with Jesus.

QUESTION #1: ACQUAINT

Food is always about more than food; it’s also about home and people and love. So how does a go-to meal at your favorite hometown restaurant reveal the true you behind your web bio?

In my early years, my family lived in Puerto Rico, where my father ran a plant for General Electric. When I walk into Amarilis, a cafe that serves Latin American food in my community on the outskirts of Philadelphia, I hear the familiar music of the island and get a whiff of garlic. I feel like I’m stepping back into my childhood.

I almost always order beef and yellow rice smothered in beans, with hot tostones (fried plantains) sprinkled with warm garlic and salt. It always reminds me of those early formative years. The atmosphere of the restaurant is somewhat forgettable, but the food is fantastic; I can taste the memories of 12-month tropical weather with every bite. I love taking friends there who’ve never experienced Cuban, Puerto Rican or Dominican food and seeing how much they enjoy the experience. And when my parents are in town, my father and I always visit and intentionally order too much food so we can eat leftovers every day for the next week.

The truth is, I could eat at Amarilis every day of the week for the rest of my life. But I also enjoy going there to be reminded through my senses of where I come from.

QUESTION #2: REVEAL

What “nonspiritual” activity have you found to be quite spiritual, after all? What quirky proclivity, out-of-the-way interest or unexpected pursuit refreshes your soul?

I grew up playing team sports — basketball, baseball and soccer — but about 10 years ago, I completed two sprint triathlons. As I trained, I found that I hated running and tolerated biking but fell in love with swimming. After the triathlons were over, I continued swimming — and I never stopped. Three mornings a week, I swim at the local YMCA. I always dread getting out of bed early in the morning (especially in the dead of winter), but once I start swimming my laps, I’m so glad I’m there.

Trust me: I won’t be breaking any Olympic records. But I’ve found it to be immensely relaxing and helpful for focusing. I knew it would benefit me physically, but it’s been more important for my spiritual, emotional and mental stamina than I ever thought. My prayer life is very active while I swim, and I feel connected to God in the pool. Not only am I praying to God for oxygen, but I’m also using each lap as an opportunity to intercede for my family, friends, neighbors, church, the leaders I have the privilege of investing in and larger issues around the globe.

It also allows me to think through ideas and dynamics — and oftentimes I come up with solutions. It’s amazing how many issues get solved and how many creative ideas I generate between flip-turns. It’s physically exhausting, but I feel completely alive at the same time. Even when I’m on the road speaking and teaching, I bring my suit and goggles and find a pool.

QUESTION #3: CONFESS

Every superhero has a weakness; every human, too. We’re just good at faking it. But who are we kidding? We’re all broken and in this thing together. So what’s your kryptonite and how do you confront its power?

One of my favorite questions I like to ask leaders is, “Where is it you need to get out of your own way?” For me, it’s my harsh inner critic. As an Enneagram One, my inner voice is always driving me toward progress and ultimately perfection. Sometimes that’s a good thing — and I love pushing myself toward continual improvement — but many days, it can be exhausting and brutal. I’m constantly asking, “What’s wrong with me? Will I ever be good enough? Will I ever fully measure up?” Nobody is harder or harsher on myself than I am. I’d never speak to anyone else with the same harshness I use with myself. Sadly, because of this, contentment, peace, joy and self-compassion are all too rare experiences for me.

I serve as a leadership coach to a wide variety of kingdom leaders. I love walking alongside leaders, encouraging, serving, supporting and helping them. But I’m still learning to live in right relationship with that intense leadership coach that resides in my own head. The leaders I work with can fire me, but I can’t fire my inner coach, so I am slowly learning to come into healthy relationship with it. I am growing in this area but still have a long way to go. I know all the right answers, but I am trying to have it move from my head to letting it run wild through my bloodstream. Learning to truly experience God’s grace in my everyday life is a lifelong process.

QUESTION #4: FIRE UP

Tell us about your toil. How are you investing your professional time right now? What’s your current obsession? And why should it be ours?

I love growing fruit on other leaders’ trees. That’s why, in 2011, I founded Kairos Partnerships, an organization that helps leaders overcome their unique challenges by equipping them to lead with clarity, confidence and consistency. Our team serves leaders through coaching, consulting and spiritual direction, and I participate in a large amount of teaching, speaking, and training of leaders, as well. I wake up deeply grateful that I get to do what I do.

One of the practical ways I most often help grow fruit on others’ trees is by asking incisive, thoughtful, caring questions. I’ve long believed that the quality of your life is determined by the quality of the questions you ask God, yourself and others.

For the past decade, I’ve researched the questions found in Scripture. Additionally, I’ve explored how and why asking questions is so powerful, and yet also massively underutilized. I ended up writing my doctoral dissertation on equipping kingdom leaders to ask better questions to lead more effectively. I sometimes refer to this as “questionable influence.”

My research led me to write a book called “The Art of Asking Better Questions.” Through it, my goal is to help everyday people (not scholars!) see the immense power that questions hold and equip them in ridiculously practical ways to ask better questions in every area of their lives. Teaching others the passion for and the skills of question-asking is one of the great joys of my life.

By the way, I must say: you ask great questions in this interview. Well done!

QUESTION #5: BOOST

Whether we’re cashiers or CEOs, contractors or customer service reps, we all need God’s love flowing into us and back out into the world. How does the Holy Spirit invigorate your work? And how do you know it’s God when it happens?

Several years ago, a mentor shared with me that when we are engaged in stewarding our spiritual gifts, we will feel both exhilarated and exhausted at the same time. I feel this dual reality when I teach, speak and coach leaders. This also includes writing, because for me, writing is teaching on paper.

To bring myself fully to a room of leaders, a book project or to an individual coaching session, I seek to be fully present. I heard Simon Sinek say years ago that before he walks onstage and communicates with people, he whispers to himself, “I am here to give.” I have adopted that practice in my own life as well.

When I give myself, pouring out what the Lord has given to me, to a roomful of hungry kingdom leaders, I feel completely alive. It’s not simply because I am adding value to them; it’s also because I’m learning and receiving from other leaders. Even when the teaching preparation is arduous or the particular issue we’re addressing with a leader may be complicated and gut-wrenching, there remains an immense joy and affirmation I sense from the Lord in the work I am doing. I may be mentally and physically tired at the end of a workday, but I’m also emotionally and spiritually invigorated. I’m grateful that the Lord has invited me to partner with him to serve, care for, encourage and equip hungry leaders. There’s just nothing like that kind of partnership.

QUESTION #6: inspire

Scripture and tradition beckon us into the rich and varied habits that open our hearts to the presence of God. So let us in. Which spiritual practice is working best for you in this season?

I’ve always loved journaling for as long as I can remember. My parents tell me I would write in notebooks and record thoughts and ideas in journals at a very young age. I write in one journal first thing in the morning and another journal right before going to bed. I’ve done this for years, as it slows me down, centers and anchors me. I like to tell those I serve that an effective leader is a reflective leader.

I’ve also spent the past few years hand-copying the New Testament, which I’m about 80% complete with right now. Recently, our church went through a 40-day reading plan together. A few artists in the church decided they would sketch something each day from the daily reading passage and then share their work with others. To be clear, I am not an artist, nor do I pretend to be one, but I decided to take a bit of a personal and creative risk and join them. Doing so has engaged a different part of my brain — and my soul — by entering into the passage and connecting with God in a fresh way. My sketches won’t be hung in a museum or sold at an art show, but they don’t need to be; the practice is connecting me to God in ways that are new to me — and I’ve loved it. In fact, when the 40-day communal reading plan is over, I’ll probably continue doing this on my own. I’m being stretched to connect with God through images, not just words.

QUESTION #7: FOCUS

Looking backward, considering the full sweep of your unique faith journey and all you encountered along the way, what top three resources stand out to you? What changed reality and changed your heart?

Wow, this is a tough question! It’s much easier for me to name authors who have had a significant impact on my faith journey: Eugene Peterson, Dallas Willard, Henri Nouwen, C.S. Lewis, Wendell Berry, N.T. Wright, Mary Oliver and Malcolm Guite, among others.

But if I had to narrow it down to three resources, it would be:

1) “In the Name of Jesus,” by Henri Nouwen, helped me understand that leadership in the posture of Christ is about love and servanthood, not power, prestige or title.

2) “The Divine Conspiracy,” by Dallas Willard, opened my eyes to the importance and the centrality of the kingdom of God — and that Jesus has invited us to live in that kingdom reality each and every day, even right now.

3) “Essentialism” by Greg McKeown. This book changed the way I think about and plan my weeks and months. It continues to help me focus on exactly what God has entrusted me to steward well, especially my time. I reread this book about four times a year to remind, reorient and refocus my priorities: what I am called to do well, while letting go of the rest. It’s helped me to be a more faithful and focused steward of my time, energy and attention — and I have no doubt my life would be in a very different place without this book.

Certain things can be godsends, helping us survive, even thrive, in our fast-paced world. Does technology ever help you this way? Has an app ever boosted your spiritual growth? If so, how?

While our family has cellphones, laptops and tablets filled with podcast episodes, Spotify and YouTube TV, I also work proactively and intentionally to be as analog as possible. My wife and I committed to not having a television for the first 17 years of our marriage. We have one now, but that was a formative decision for us in our early years.

But while screens now seem ubiquitous, I have a handful of specific practices that have helped me immensely. First, I deleted all social media apps from my phone. I use them on my laptop, but I needed freedom from it when on my phone. Second, I love reading physical books — the ones I can actually hold in my hands and flip through the pages — and I read every day for at least 30 minutes. Third, as I mentioned earlier, I journal every morning and evening. I am very tactile. Sitting on the back porch on a nice evening and reading a book is one of the great joys in life. And lastly, I often intentionally “forget” my phone at home when I go for walks in our neighborhood. I’m too easily distracted, so I try to eliminate that distraction and be as fully present to my environment as I possibly can.

I don’t do these because I am the exemplar of focus and discipline; I do these because I need help eliminating distraction because I can’t do it by sheer willpower.

QUESTION #8: dream

God’s continually stirring new things in each of us. So give us the scoop! What’s beginning to stir in you but not yet fully awakened? What can we expect from you in the future?

I often tell the leaders I coach to dream bigger than they are at the current moment — so I’d be a hypocrite if I didn’t do the same. So thanks for this question!

I’m grateful to have written several books over the past 20 years. But my new book about asking better questions is the topic I’m most passionate about. I didn’t just want to write a book; I want to see people changed by it. I desire to see this message start a movement. I want to see our culture recognize the immense power of asking great questions — and then see that take root and provide real cultural change. Less division and more connection. More curiosity, less judgment (thanks, Ted Lasso!). More bridge-building than wall-building.

There are plans coming together in this next season where our team is creating more places and spaces to teach, train and equip people in various fields and sectors to learn to harness the power of asking better questions. Whether you’re a stay-at-home mom, a bread truck delivery driver, an attorney, a teacher, a student or a grandparent, all of us can significantly improve our lives and the lives of those around us by asking better questions. The quality of your life is determined by the questions you ask God, yourself and others.

I just can’t ignore it: questions are important in all areas of our lives. And I want to spend the next 20 years honing the skill, deepening the passion and equipping people — specifically leaders — in this invaluable area of our lives.

Earlier, J.R. shared his passion for asking the right questions — because he knows that questions have the power to help us or hurt us. Take the first two questions recorded in the Bible as an example.

The first was posed by the serpent, who asked Eve, “Did God actually say, ‘You shall not eat of any tree in the garden’?” (Gen 3:1, ESV). This question still haunts the human race today. When we ask ourselves, “Did God actually say …?”, we entertain doubts about him, his Word and even his love for us. In turn, we move further away from God, sinking deeper into sin and misery.

But then God asks his question, one that is far more powerful than the serpent’s. “Where are you?” he asks Adam and Eve, who had just eaten the forbidden fruit and were hiding in the garden (see Gen 3:9). This question is just as relevant today as it was back then. Where are we? What are we hiding? What are we ashamed of and longing for? The answer, when we’re truly honest with ourselves, will always reveal our deep need for relationship with God.

What questions are you asking, reader? Are they helping you or hurting you? What questions can you ask that will help you better understand your need for Jesus and his love for you?

🎉 Easter Egg Activated!

J.R. Briggs