How to Grow in Leadership by Asking Questions

Letting questions lead the way

Part 1: This is the first of a three-part series on how leaders can grow into living a question-led life.

When Jesus teaches, he uses three primary tools that assist his followers in their transformation: experiential learning opportunities (“field trips”), storytelling, and question-asking. Jesus is the master of question-asking. Because of the nuances of translation between Aramaic and Greek and English, it’s difficult to pinpoint exactly how many questions Jesus asks, but more than 300 are recorded in the Gospels (and one in Acts).

Jesus is also on the receiving end of 183 questions in the Gospels. Intriguingly, he answers only five of these directly and three semi-directly.

Given this, it seems appropriate to ask a question of ourselves: We study the miracles of Jesus. We study his parables. We study his teachings. We study his interactions with the disciples. But if Jesus asked so many questions, why don’t we spend more time studying those?

Jesus the Great Question-Asker

As we think about Jesus and his questions, we will find it worthwhile to see not only what questions he asked, but also how he asked them, who he was asking, where he asked them, and then why he asked them at all. By asking a good question at the right time of the right person for the right reason, he was often able to have an unexpected impact. Yes, he taught and preached and told stories, but it was arguably his questions that were most gripping, engaging, and life-altering.

If we could choose one adjective to describe the kinds of questions Jesus asked, we might be wise to land on incisive. In Matthew 16, Jesus asks, “Who do people say that I am?” in order to ask a more significant (and more personal) question of the disciples: “What about you? Who do you say that I am?” (Matthew 16:13-20). That’s as incisive as it can get, cutting through to the heart of their faith in him. Like a surgeon with scalpel in hand, Jesus asks questions that create little incisions in people’s hearts—not to hurt, but to heal. Jesus asks questions not out of ignorance, but out of a desire for relationship.

Leading by Asking Questions

In our culture, leaders are often looked to as the answer-givers. Leaders are expected to be in control, to know all the answers, to be brave and strong and well-informed. They are to disseminate information. But what if leaders thought of themselves first as lead question-askers? Could this make for more effective leadership? Don’t we need leaders who are curious and courageous, who don’t always supply all the answers, but instead create an environment for others to discover answers on their own? Could people lead better with their ears than with their mouths?

Questions invite the listener into deeper levels of thinking. They stir the imagination, encouraging—even forcing—people to participate in a story, teaching, or conversation. Perhaps this is why Jesus asked so many questions: to draw people in to a new way of understanding.

Learning from Jesus’s Questions

Leaders today can learn to ask questions like Jesus did. Let’s start by learning to recognize the questions of Jesus. As you read through the Gospels, watch for questions. Then consider these four factors:

  • Situation: Where does Jesus ask this and who is present?
  • Purpose: Why does he ask this? What is his purpose in asking rather than telling?
  • Response: How do people respond to his question (or not)?
  • Impact: What impact does it have? How does the question bring about change?

Let’s consider those four factors in relation to the questions in Matthew 16:13-20.


Jesus and his disciples are on a field trip to Caesarea Philippi in the northern region of Israel, a few days’ journey on foot from their home turf in Galilee. This village, also known as Banias (or Panias), was dedicated to the god Pan. Even today, one can see many niches cut into the side of a large rock scarp there, with idols carved in the niches.


Did Jesus simply want to know what folks were saying about him? Maybe, but the situation suggests he intended this as a moment of challenge. Jesus could have asked these questions back in the temple in Jerusalem, but instead Jesus takes the disciples to a specific location filled with hundreds of idols. It’s as if he is asking, “So, in the midst of all of these so-called gods, where do I fit in? Am I just another idol, or am I more than that?”


We don’t know if or how the other disciples responded, but Peter’s response—“You are the Christ”—is powerful. He acknowledges—some scholars believe for the first time—that Jesus is the Messiah.


Jesus uses this teachable moment to speak into Peter’s life and tell him about his future. He will be the rock on which Jesus will build his church, so strong and stable that even the gates of Hades can’t overcome it. With many of the questions of Jesus, we don’t see immediate impact, but this could be viewed as a step in Peter’s long journey toward church leadership.

The Leadership Context

Now imagine putting this passage into our context as leaders.

What do people in our culture think about Jesus? You might ask the people you lead to give you a cultural report. What are they hearing from those they work and play with? But then you could turn the question toward them, just as Jesus did. What about you? Who do you say Jesus is?

Those questions might create a teachable moment, but maybe more so if we consider situation, purpose, response, and impact.


Where could we take people today that would have some of the character of Caesarea Philippi with its flagrant idolatry? Maybe a sports arena, a concert venue, an ad agency, a high-rise building in the financial district, or a college lecture hall? Where are the specific locations where worship is occurring in our culture, and how would a “field trip” make the questions more powerful?


Why is it important for people—and especially for the people you lead—to answer this question today? Do they need to be more aware ofthe opinions of people around them, or do they need to decide their own opinion of Jesus? Further, how might their beliefs about Jesus affect the way they deal with the gods of our world—sports, entertainment, money, power, or beauty?


Understanding that we respond not only with our words but also with our lives, how might the people in your group acknowledge who Christ is and then act accordingly this coming week?


We could ask the group how being “on location” might be more impactful than looking at this passage in someone’s living room or in a Sunday school classroom. We could follow up by asking what it’s like to have our idols identified, called out, and compared to Jesus. How does this make us think and feel moving forward?

Our curiosity about the questions of Jesus can stir our imaginations, but also help us dig deeper and explore Scripture more expansively. As we seek to follow Jesus, we can emulate his question-asking as well. And, in doing so, we can grow in our own ability to lead others with equal measures of wisdom, courage, and compassion.

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J.R. Briggs
J.R. Briggs

J.R. Briggs started Kairos Partnerships in 2011 where his role is expressed through coaching, consulting, speaking, teaching, equipping and writing to serve a wide variety of leaders, pastors, churches, non-profits, ministries, companies and denominations. Over the past several years, he has invested in kingdom leaders in over 23 states from over 40 different denominations. In addition to starting Kairos Partnerships, he planted The Renew Community, received a master’s degree in Missional Theology at Biblical Theological Seminary, and is currently working on a Doctor of Ministry degree at Biblical. His doctoral thesis focuses on how question-asking in leadership can advance God’s mission. He is an author, co-author and contributed to nine books that seek to equip and care for kingdom leaders. J.R. and his wife Megan have been married for over 16 years and have two sons, Carter and Bennett.

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