Lots of evangelism resources advocate asking questions as a way of initiating spiritual conversations. That is really good. I like asking questions (ad nauseum). But, no matter how good the questions, they do not replace my own need for answers. Let me explain.
When we talk about the importance of questions in spiritual conversations, we often cite how many times Jesus asked questions. The Scripture witness has Jesus’ scorecard as topping 300 questions. Some will push this scorecard idea further to maintain that: Jesus asked 307 questions; there are 183 questions asked of Jesus; but He only gave 3 direct answers.
Regardless of the scorecard metrics, the foundation is laid that we have a model of demonstrating love through authentic curiosity, asking leading questions that move the conversation deeper, and engaging in active listening to make the conversation real communication. A quick question here . . . do you think that Jesus knew the answers to His own questions?
Our rush to questions does not get us off the hook from wrestling with our own discipleship process. Questions are not license to be smug about our sophisticated conversation skills so the other person does not even know that we are leading them into a spiritual conversation. Questions necessarily move us, as in we, you and I, into authentic reflection.
Let’s use the example of when Jesus asked the disciples, “Who do you say I am?” (Matthew 16:15). I am going to posit that Jesus was looking for an answer to this question from His disciples. He was not just modeling a good question, or how to use good questions, He was calling the disciples to respond with an answer. Jesus’ questions are not just for others. He is calling to you and I to respond.
Questions are great, and I welcome the approaches to evangelism that utilize leading questions. Rather than just rushing forward with questions though, I would advocate that we spend some more time thinking and praying through our own answers. This is an activity that is not just a Lone Ranger Christian activity. Wrestling through these questions in the community of our church family is critical as we seek to be disciple-makers.
Let’s ask great questions. But, I think we will ask better questions if we work on answering the questions that Jesus is asking us. In the community of our church family.
 A few examples of the question approach or documentation: Schaller, Mary and John Crilly. 2016. The 9 Arts of Spiritual Conversations: Walking alongside People Who Believe Differently. Carol Stream, Ill: Tyndale.
 Copenhaver, Martin B. 2014. Jesus Is the Question: The 307 Questions Jesus Asked and the 3 He Answered. Nashville: Abingdon.