Engaging Through Asking: 5 Ways Jesus Asked Questions

Jesus is the Master of questions. He expertly digs down into reality to produce both self- and God-awareness in others. If we are going to be on mission with Him, we must become careful and wise in asking good questions of our culture as well. The Rev. Matt Tebbe of Gravity Leadership explores 5 crucial qualities of the questions Jesus asked in the Gospels—and how we can learn from them.

by Matt Tebbe

Karl Marx famously said that “religion…is the opiate of the masses.” While we may quibble with his idea when it comes to true Christian spirituality, Marx actually has a prophetic edge here: Many continue to use their spiritual life as an escape from reality; to numb their pain and remain disconnected from their hurt.

But genuine Christian spirituality is a rigorous commitment to reality. It is a deeper rootedness in the world, as Jesus himself prays for us (John 17.15).

Truth is: God is so real that he most fully meets us where we really are.

A beautiful picture of God meeting us where we really are occurs in John 4 with Jesus’ encounter with the woman at the well. Jesus reveals who the woman is to herself – he deals with what REALLY IS – and then – he reveals himself to her. We see here, in a distilled, distinct way that when the woman comes to reckon with who she really is, she is able to see God as he really is.

God, and we, are revealed in reckoning with reality.

Questions: How Jesus Digs Down Into Reality

There is a deep tradition in Christian spirituality that knowledge of God is connected to self-knowledge, and knowing self is connecting to knowing God.

John Calvin wrote in 1530: “Our wisdom…consists almost entirely of two parts: the knowledge of God and of ourselves. But as these are connected together by many ties, it is not easy to determine which of the two precedes and gives birth to the other.”

Self-awareness and God-awareness go hand-in-hand. If we are going to meet God in our actual life – and not in the “opiates” of our pretensions, religious fantasies, or theological abstractions (much of which passes for authentic spirituality today) – we need to become more acquainted with the depths of who we are.

Jesus was ruthless about getting to the heart of people. We see Jesus do this when he engaged with others – he not only revealed the Father to them, but he also revealed who they were through questions. Here are a few potent examples:

“Why do you call me good?” (Luke 18.19).

“What do you want me to do for you?…Can you drink the cup I drink and be baptized with the baptism I am baptized with?” (Mark 10.35-38)

“What do you want me to do for you?” (Luke 18.35-41)

“What do you want?” (John 1.35-37)

“Will you give me a drink?” (John 4.7)

“Do you want to get well?” (John 5.6)

The Difference Between Our Questions and Jesus’ Questions

Jesus asks 307 questions in the Gospels. He’s a master at asking questions. If we are going to become more like Jesus and do what He did, we must become careful and wise in asking good questions as well. But: Jesus uses questions differently than we commonly do today.

We ask questions for information; Jesus asks questions to provoke transformation.

We ask questions for answers; Jesus asks questions for awareness.

Jesus asks questions to confront the listener with their own thought process, preconceptions, assumptions, and beliefs.

And this makes sense, doesn’t it? Jesus is after repentance as you recall (see Mark 1.15). He wants us to reckon with our own conception of reality and examine it in light of what God has to say. In order for us to do this, we have to reckon with what we actually think!

If we want to follow in the footsteps of Jesus, we have to learn to ask questions the way Jesus does: to reveal hearts, to open up hidden reality for others.

If we want to follow in the footsteps of Jesus, we have to learn to ask questions the way Jesus does: to reveal hearts, to open up hidden reality for others.

5 Qualities of Jesus’ Questions

I notice a pattern in Jesus’ interactions with others, 5 qualities in his questions that enable him to reckon with reality in a transformational way:

  1. Concrete – Jesus asked a lot of “what” and “why” questions. He showed little patience for abstract theological conversations (see Matt 22.23-34, for instance). If he had a blog today, his comment section would most undoubtedly be “closed.” Jesus drives down into particulars, specifics, details. He wants to deal in the granularities of actual life. The more particular, specific and detailed we can get with our questions the better.
  2. Connection – The religious leaders interrogated Jesus with questions. Their questions weren’t sincere: they were traps set to win power and approval from others. But Jesus posed questions to connect with others. Questions are a personal encounter for him. His questions communicate through body language, speech, eye contact, and touch that he is present and with and for the one who is sharing. Jesus did this quite often: – Eye contact: (“Jesus looked at him and loved him” – Mark 10.21; “The Lord turned and looked straight at Peter”- Luke 22.61) – Jesus would remove people from crowds so he could personally connect and touch them while healing them. (Matt 8.1-3; Mark 7.33-35; 8.22-26) – He used first names to communicate intimacy (“Martha” – Luke 10.38-42) or questioned women in public, a demonstration of intimacy that was outside the bounds of Jewish culture. (John 4.7; 8.10) – And Peter and John imitated him well. (see Acts 3.3-7)
  3. Compassion – Connection is a part of compassion, but compassion runs deeper in that we bring some gentle tenderness to whatever someone shares. Jesus had incredible presence, able to bear with another in whatever they were dealing with so that they could experience the grace of the Father (see John 21.15-17 for this sort of compassionate questioning). It is the kindness of the Lord that leads us to repentance (see Romans 2.1-4; Matt 7.1-5). For many, asking and listening in compassion is difficult because we cannot bear another’s badness or anxiety without wanting to solve or fix it. We’re a better judge and accuser than advocate and friend.
  4. Curiosity – Jesus models curiosity, asking open ended questions so that people could discover the Kingdom in their midst. This genuine curiosity holds open a space of safety for discovery, to meet God in our depths vulnerably and authentically. This is not something we are accustomed to: most of us have many ways to avoid vulnerability. Or we turn question asking into an interrogation where others are triggered into defensive, rationalizing postures.
  5. Courage – Finally, to ask questions like Jesus takes courage. Looking at ourselves with God can be a terrifying experience (see Job 42.6; Isaiah 6.5; Luke 5.8). Perhaps this is why the most repeated phrase from God to humans is “Do not be afraid!” We’d much rather ignore, justify, rationalize, avoid, or medicate the truth about ourselves. We come by these evasive moves honestly (Gen 3.8-13) but they have never done good work for us. It takes courage to stand before God just as we are and name what really is.

Of course, learning to ask good questions is only the beginning. But until we reckon with where we really are, we cannot begin to know God. And Jesus used questions to help people excavate where they really were at.

Until we reckon with where we really are, we cannot begin to know God.

In a world where pastors are called on to be expert advisors and “tell it like it is,” we have a greater need than ever to learn from Jesus how to ask transformational questions, helping people be at home with where they are (really), so that they can meet God right there.

Need more on this topic? The Telos Collective partners with Matt and his team at Gravity Leadership to offer coaching for Anglican leaders in all areas of engaging culture.  

Matt Tebbe has been a coach, communicator and consultant with churches in North America since 2011. Matt has experience as a youth pastor, a bi-vocational church planter, and working on a team at a large church to transition it from a Sunday-centric worship service to a discipleship and mission paradigm. He co-founded Gravity Leadership, and is planting a church (The Table) in the northeast suburbs of Indianapolis, where he and his wife Sharon live with their children Deacon and Celeste.