Jesus' Master Class in Questions

Once people have started to chat more meaningfully, the next step is to press into the art of asking good questions.

We aren’t trying to win arguments or prove a point - that’s such a short term vision! Instead, our goal is to build authentic relationships and create space for deeper connection.

In the Old Testament we often see God asking questions. Remember: God doesn’t ask humans questions in order to gain information! Instead, He might be stirring us to think, or to press deeper into His heart, or to repent of certain behavior, or to change our beliefs, or to recognize His beautiful presence and hand at work.

• “Where are you?” to Adam (Genesis 3:9, NIV), when he and Eve thought they could hide from God. This is perhaps the saddest and most devastating question in all of Scripture.
• "What is that in your hand?" to Moses (Exodus 4:3, NIV), as his everyday staff became a powerful spiritual weapon (via the amusing moment in the next verse when Moses was freaked out - “Moses threw it on the ground and it became a snake, and he ran from it”!
• “What are you doing here?” to Elijah (1 Kings 19:9b, and 13b, NIV), before recommissioning him with instructions that led to the most impactful phase of his life and ministry.
• “Whom shall I send? And who will go for us?” to which Isaiah boldly responds, “Here am I. Send me!” (Isaiah 6:8, NIV).

These questions start with curiosity, reaching beneath the surface to draw people deeper into their own stories and calling, within the greater story that God was weaving.

In Jewish rabbinic tradition, teaching wasn’t just about giving information, but also about asking questions that invited reflection, dialogue, and discovery. This was already well-developed in the centuries leading up to Jesus, and you see it everywhere in the New Testament.

In fact, Jesus frequently taught this way. The Gospels record Him asking over 300 questions, often answering a question with a question. His aim wasn’t to confuse, but to engage, not to shut down, but to open up.

Think about the way Jesus asked these questions:

• “What do you want?” to the two disciples who first sought him out (John 1:38, NIV). His questions invited them to take their next step on their faith journey.
• “Why do you call me, ‘Lord, Lord,’ and do not do what I say?” to the crowd as He wrapped up Luke’s account of the Sermon on the Mount (Luke 6:46, NIV). This question called them to not just be hearers, but doers of His words.
• “What do you want me to do for you?” to blind Bartimaeus and his cry for mercy (Mark 10:51, NIV). This seems strange, until we realize that Jesus was creating space for Bartimaeus to express and grow in his own faith.
• “What are you discussing together as you walk along?” to Cleopas and his companion as they walked despondently to Emmaus (Luke 24:17, NIV). Jesus then used this as the gateway to perhaps the greatest Bible study in history (v.27)!

Asking good questions shows respect for the other person, creates dialogue, and draws out deeper truths. They can unlock honesty, reveal motives and desires, and create space for divine revelation.

When we’re with people and have engaged in some casual chit chat, we can start to ask questions which move the conversation into things that are more meaningful.

Practically, when we’re in a conversation, don’t stop at the first answer. If someone says they’re “fine,” you could gently ask, “Just fine?” If they say “good,” follow with “Why good?”

Here are a few other examples:

• “What’s going well in life right now, and what’s not so good?”
• “How are you feeling about [that situation]?”
• “What in your life gives you meaning?”
• “What do you think about…?”

Sometimes, the best question is simply, “Can you tell me more?”

Don’t forget that listening to the Holy Spirit is part of this too. Quietly pray, “Father, give me Your heart for this person. Show me what to ask.” Often, the Spirit will highlight just the right question at just the right time.

You don’t have to have all the answers. In fact, sometimes you build the most connection by asking for advice. If someone has a vibrant marriage, or is great at saving money, or is skillful in a sport or hobby, say, “I’d love to learn from you! What’s worked well?” That kind of humility builds bridges.

Friends of ours put it like this: "Come with a posture of curiosity rather than certainty". You can’t influence someone you’re judging!

If we come with the same attitude as Jesus, then we don’t need to know everything. It’s how we engage in the conversation that counts. And doors will open!

Your Next Steps

1. Review your recent conversations. Were you mostly giving information or asking good questions?
2. Choose one or two sample questions to practice several times this week.
3. In your next conversation, silently ask, “Holy Spirit, what’s the right question here?”

Prayer

Father, thank You for the way You ask questions that draw me out and help me see myself more clearly. Teach me to do the same with others. Give me humility, curiosity, and Spirit-led wisdom. Help me to ask questions that open hearts, build trust, and point people toward You. Amen.