Leadership in Question
J.R. Briggs
November 23, 2023

For People’s Lives to Change We Must Change Our Questions

Who do you know who asks great questions?
What do they do to cultivate those good questions?
What is it about the power of a question?

Have you ever wondered why we don’t ask thoughtful and significant questions in our culture more often?
Is it that we don’t know how? Are we too impatient, prideful, uninterested, or unaware? Or are we fearful – afraid of what we might find out about others – or ourselves?

What might it say about a leader who doesn’t ask questions?
What might questions provide in leadership roles that answers simply cannot?
What if the current paradigm of leader-as-expert was replaced with the paradigm of leader-as-lead-questioner?

. . .

The late organizational guru Peter Drucker said, “The leader of the past may have been the person who knew how to tell, but certainly the leader of the future will be a person who knows how to ask.” With the heavy use of the internet and the pervasive presence of smartphones and other devices, availability of information is, quite literally, at our fingertips. With our advancing technology – now even with A.I. – we don’t even need our fingers. With a voice command, we are capable of retrieving information faster and more easily than at any time in human history. With the ubiquity of Google, do we really need leaders who need to know all the right answers? And if we are looking for better answers, should we not start by asking better questions?

In its least common denominator, leadership is about trust and connection. It’s ultimately not about charisma, education, or brilliance. It’s not about gravitas or title or prestige. In this cultural moment, with too much information, fraught with cynicism and too little trust and connection, we don’t need smarter or more eloquent or more efficient leaders; instead, we need wiser, deeper, more engaged leaders.

Wisdom is developed and depth is cultivated not by knowing all the answers, but by cultivating humility to learn, insatiable curiosity to observe, patience to listen, compassion to see and hear others, and the courage to wonder. Few things create the foundation of connection and relationship more than humility. Wisdom is gained in the quality and the frequency of the questions we ask of ourselves, of God, and others. Wise leaders ask questions. I’m convinced that what the world so desperately needs right now are leaders who ask the right questions at the right time to the right people for the right reason. The challenge and invitation for us as leaders in our current age is this: can we see the importance and significance of asking honest, compassionate, incisive, courageous questions of God, ourselves, and others?

Questions are a gift we offer to others. When people ask you questions – and truly care to know you and your story, it’s a gift – a valuable gift – isn’t it? Asking great questions gives hope, opens up new possibilities, adds value, cultivates opportunities for deeper connection, and provides meaning to others and ourselves. Like a surgeon uses a scalpel to make an incision on a patient in the operating room to provide healing, leaders can deftly use questions like a scalpel on people’s hearts. I’ve found that the greatest questions asked are personal – so personal that they draw blood, not to hurt or cause damage, but to bring healing.

. . .

The Greek philosopher Socrates (469 to 399 BC) is considered one of the founders of Western philosophy. His method of question-asking, the Socratic method, placed a high value on inquiry-based dialogue that led to learning. He used questions to draw out conclusions from others that could not have occurred through mere answers. Socrates died at the age of 71 because people, specifically three men, Anytus, Meletus, and Lycon, viewed him as a threat. He stood trial and was found guilty, ultimately forced to drink poisonous hemlock. Why? Because he asked questions. People believed that Socrates’ questions, not his answers , poisoned the minds of the youth of Athens.

Socrates often used two metaphors to describe the role of questions. The first was a horsefly, intended to sting people to get their attention – and to get them moving. The second was that of a midwife. Socrates’ mode of inquiry-based dialogue, a method that draws ideas and perspectives out of someone, is called the maieutic (may–oo-dek) method. Maieutic comes from the Greek word which means midwife. Socrates’ mother was a midwife. He, too, believed that through his questions, he was a midwife, drawing out new life with others. The best questions are so powerful they either sting or bring new life – and sometimes both.

. . .

In our Christian faith, Jesus is identified as many things: savior, Lord, redeemer, rescuer, master teacher – even leader. And many in our culture are quick to revere him as the Answer Man. Even our bumper stickers claim Jesus is the answer to all of our questions. But few, if any, see Him as the Man of Questions. As Christians, we study Jesus’ miracles, stories, parables, teachings, healings, and interactions with others. But how many of us have devoted significant time to exploring Jesus’ questions? There is rich learning to be had by exploring the questions Jesus asked, as well as the way He asked them and the impact those questions had on His listeners.

If we are to follow Jesus and lead others to follow Him as well, wouldn’t it be wise to learn to emulate His question-asking posture? Answers, most certainly, continue to play an important role in our world. We need answers. But Jesus – the savior of the world – was full of questions. Consider some of the questions He asked: Which of you by worrying can add a single hour to your life? Why are you so afraid? What do you want me to do for you? Do you want to get well? But what about you? Who do you say that I am? What are you looking for? Do you love me?

There is hardly a page in the Gospels where Jesus wasn’t asking at least one question. The Gospels record that Jesus asked over 300 questions. It also records that He was asked over 180 questions – yet He only directly answered 5 . Roughly 1% of the time Jesus answered a question directed toward him. And yet he was quick to ask hundreds of questions of others.

May we be the kinds of humble and wise leaders who ask questions – questions the way Jesus asked them – for when we do our lives will change, as will the lives of those we interact with.
By Bob Hyatt • October 7, 2026
“When God works in us nothing is useless, and nothing is spared.” - Jeannine Brown, Carla Dahl and Wendy Corbin Reuschling, Becoming Whole and Holy “There is no circumstance, no trouble, no testing, that can ever touch me until, first of all, it has gone past God and past Christ, right through to me. If it has come that far, it has come with great purpose, which I may not understand at the moment.” - Alan Redpath Here's something I've noticed about people as they get older: they tend to go one of two ways. They either get sweeter with age or they get crankier. They grow wiser and more like Jesus, or they grow bitter and more like the worst version of themselves. That's because life is formation. Everything we do and everything we go through shapes us one way or the other, mostly depending on how we respond to what happens to us, whether it's extraordinary or completely ordinary. Ministry works the same way. I've watched leaders come out of nearly identical trials in completely different shape. Some come out stronger. Others come out deeply wounded, discouraged, and ready to quit. The difference usually comes down to where they see God in the middle of the struggle, absent or present, and what questions they ask about it. Some ask, "God, why is this happening to me?" Others ask, "God, what could you want to form in me through this?" Both views of God will shape us, and so will both questions. They just shape us in very different directions. In my experience, the most common sin in church leadership is an obsession with numbers and results, paired with neglect of our own souls. On top of that, we rarely stop to notice how those numbers and results, and how ministry itself, are shaping us. So here's my suggestion: stop working so hard to develop your ministry and start noticing that your ministry is developing you. How you handle the realities of church leadership will determine not only what your church becomes but what you become. Leadership and ministry will form you. The only question is: into what? One tool God uses: the fishbowl Some people hesitate to become a pastor because it opens them up to scrutiny, and now and then to outright criticism. When I was a young leader, I hated the "fishbowl effect" of ministry. Everyone was watching me, and my mistakes seemed to count for a lot more than anyone else's. It felt deeply unfair that flaws that wouldn't even register at most people's jobs could cost me my job, my reputation, and my community. Never mind that maybe it bothered me so much because I had such a generous supply of those flaws. After years of living under the steady gaze of critics and cranks, I see the fishbowl differently. These days I actually welcome it. Richard Baxter, a Puritan pastor in the 1600s, put it this way: “While you are as lights set upon a hill, think not to lie hid... do your work as those that remember that the world looks on them... ready to make the worst of all... and to make faults where they cannot find them.”[1] Baxter understood that anyone who calls others to live like Jesus is going to get called out when they don't. His advice? Live like the world is watching, because it is. Some people in your life are ready to yell "Hypocrite!" at the first opportunity, to point out failings they share themselves, and, as Baxter says, even to invent faults when they can't find real ones. And Baxter's fishbowl had a few neighbors peering over the fence. Ours has a livestream, a comment section, and someone screenshotting the announcements. But Baxter goes further. He says we should be glad about it: “As you take yourselves for the lights of the churches, you may expect that men's eyes will be upon you. If other men may sin without observation, so cannot you. And you should thankfully consider how great a mercy this is, that you have so many eyes to watch over you, and so many ready to tell you of your faults; and thus have greater helps than others, at least for restraining you from sin. Though they may do it with a malicious mind, yet you have the advantage of it.” As a Pastor, you have more eyes on you and more people paying attention to how you live. That means you have more help than most in living well and avoiding sin. What some people mean for evil, God means for your good (Genesis 50:20). What looks like a downside of ministry turns out to be a path to maturity, to formation. In practical terms, living your life in front of others pushes you to do what you already know you should do. And it often keeps you out of things you might slide into if nobody were watching. One important caveat: embracing accountability isn't the same as tolerating abuse. Healthy scrutiny sharpens you. A congregant who attacks your spouse or treats your kids like church property is a different problem, and it calls for boundaries, not gratitude. Let's be clear, though: the fishbowl isn't enough on its own. What we're really after is internal: character, a changed heart. But knowing we're living out loud in front of a watching church and a watching world gives us structure, and that structure can help us build the habits and rhythms of holiness we want. As we try to let the heart and character of Christ take deeper root in us, we have the advantage of lots of eyes around us "encouraging" us to stay on the straight and narrow. My sense is that people who embrace this find that, over time, what starts on the outside moves more and more to the inside. Slowly, the choices we make because others are watching become, through habit, real character. Because I know people are watching, I think twice about what I say in public, what I scroll past on my phone, and how I talk to my kids at church or out on the sidewalk in front of the neighbors. More and more, those choices, first made because of an audience, become part of who I am. That's especially true when I treat those moments as kairos [2] moments: times when God breaks in and uses my awareness of a watching world to show me the character He wants to form in me and the choices He'd like me to make. But what if we don't embrace it? What about those who get shipwrecked by moral failure, character flaws, and private sins gone public? People who resent the fishbowl of ministry and the Christian life often end up living one way in public and another in private. It's as if their anger at being scrutinized pushes them into a divided life: they'll play by the rules in public but insist on their own rules in private. Frustrated with the audience around them, so eager to find fault, they forget the true Audience they live before. And as we've all seen from too many spectacular crash-and-burns, the fallout is often devastating. Families, churches, and the reputation of the whole Church take serious damage. Pastors, recognize that your formation is happening, one way or another… and make peace with the fishbowl. It's going to be there whether you like it or not. If you embrace it, you may find it spurring you on toward love and good deeds (Hebrews 10:24) and keeping you clear of the sins that have taken down so many in ministry before you. “You should thankfully consider how great a mercy this is, that you have so many eyes to watch over you.” Let the Holy Spirit use your public life, and every eye watching it, to shape and form you. The fishbowl and the formation of a life in ministry are coming either way. Let them help answer the question: into what? To further explore your own formation through ministry, join us at the Multiply Summit with special guest Rich Villodas this coming February in the Washington, D.C. area! Adapted from Eldership and the Mission of God by Bob Hyatt and J.R. Briggs. [1] Richard Baxter, The Reformed Pastor, London, 1657, p. 21. [2] Kairos is one of the Greek words for time, but it's different from chronos. Chronos is linear, calendar time. Kairos refers to significant moments full of possibility. Here, it means those times when God steps into chronos.
By Bob Hyatt • April 13, 2026
Here's a message from Ecclesia Pastor Aaron Graham