Christians know that we are to gather others to Jesus or we will scatter (Matthew 12:30). The mission of the church is to make disciples of all the nations baptizing them and teaching them all that Jesus commanded (Matthew 28:18–20). An effective approach to evangelizing is to ask questions to get others thinking especially in a restrictive environment or in a difficult circumstance. This post draws wisdom from Jesus in asking questions to encourage thought, defend against attacks, and open the door for sharing the gospel. The apostle Paul encouraged the faithful, “Walk in wisdom toward outsiders, making the best use of the time. Let your speech always be gracious, seasoned with salt, so that you may know how you ought to answer each person” (Colossians 4:5–6 ESV).
Asking Questions
When Christians think of sharing the gospel with others, we often reflect on Jesus’s parable of sowing the seed and the types of soil. Some ground was hard, rocky, or thorny and so not ready to receive the seed that is God’s Word. Jesus taught, “As for that in the good soil, they are those who, hearing the word, hold it fast in an honest and good heart, and bear fruit with patience” (Luke 8:15). However, we are often surrounded by hard hearts and limited by social expectations. We are wise to take a less direct approach to learn first what others think. Jesus commanded His disciples in sending them out, “Behold, I send you out as sheep in the midst of wolves; so be shrewd as serpents and innocent as doves” (Matthew 10:16).
Throughout the Gospels, Jesus asks questions. “And behold, a man came up to him, saying, ‘Teacher, what good deed must I do to have eternal life?’ And he said to him, ‘Why do you ask me about what is good? There is only one who is good. If you would enter life, keep the commandments.'” (Matthew 19:16–17). Jesus’s questions are still affecting people today. Christians are wise to use these questions in the right way rather than ask questions today like the Pharisees did in an accusative way. This post is intended to help us ask questions in the way that Jesus did to expose the responsibility of faith upon the hard-hearted.
Jesus’s Responses to Encourage New Thinking
When someone comments on a current event whether you agree or not, you can ask, “What do you think about…?” and encourage them to think out loud about the state of a sinful world in need of a Savior.
The next level includes carrying the conversation by asking other questions like “How did you arrive at that conclusion?” For instance, if someone says that she does not believe in talking about religion, you can ask her, “Why do you avoid talking about religion?” or “How do you avoid talking about religion?” The question that Christians should constantly ask those who differ is “Why?” and “How?” to draw out the person’s thinking and reasoning (if they have thought about why they believe what they believe). Then you can encourage a conversation by asking her how she defines “religion.” Ironically, that will often lead to a friendly discussion about religion, faith, and the gospel of Christ.
Immediately after Jesus fed the 4,000, some Pharisees came to test Jesus by asking for a sign from heaven. Jesus replied, “Why does this generation seek a sign? Truly, I say to you, no sign will be given to this generation.” What fruit would come from Jesus asking “Why”? The Pharisees did not understand that they just missed a sign from God and they revealed how they would have responded to the sign.
After Jesus responded to the Pharisees asking for a sign, Jesus’s disciples were discussing not having bread other than one loaf while traveling across the Sea of Galilee (Mark 8:14–16). To get them to think, Jesus asked, “Why are you discussing the fact that you have no bread? Do you not yet perceive or understand? Are your hearts hardened? Having eyes do you not see, and having ears do you not hear? And do you not remember? When I broke the five loaves for the five thousand, how many baskets full of broken pieces did you take up?” (Mark 8:17–19). Jesus’s goal was simply to get others to think about the obvious works of God so that they wonder, seek, and find.
Questions for Defense
Jesus also used “why” questions in defense to challenge antagonists:
- In the Sermon on the Mount, Jesus challenged listeners, “Why do you see the speck that is in your brother’s eye, but do not notice the log that is in your own eye?” (Matthew 7:3).
- When Jesus knew that some were questioning His ability to forgive sins, Jesus knew their thoughts and challenged them, “Why do you think evil in your hearts?” (Matthew 9:4).
- When some of the disciples were skeptical of the woman who anointed Jesus’s head, He replied to them, “Why do you trouble the woman? For she has done a beautiful thing to me” (Matthew 26:10).
Jesus was always asking challenging questions and so turning the tables over on those challenging God’s authority. Likewise, Christians should follow Jesus’s example and ask others to account for their beliefs.
Challenging Questions
Another question to challenge others to consider is to ask: “How can you say that?” There are certainly other ways to ask this. Jesus asked this question with an addendum of “when…” so that He asked, “How can you say to your brother, ‘Let me take the speck out of your eye,’ when there is the log in your own eye?” (Matthew 7:4).
There are various ways that this question can be used:
- In evangelism, Jesus taught Nicodemus, “If I have told you earthly things and you do not believe, how can you believe if I tell you heavenly things?” (John 3:12).
- When antagonists challenged Jesus, He responded, “How can you believe, when you receive glory from one another and do not seek the glory that comes from the only God?” (John 5:44).
- Jesus responded to unbelievers, “For if you believed Moses, you would believe me; for he wrote of me. But if you do not believe his writings, how will you believe my words?” (John 5:46–47; cf. John 8:43; 14:9).
- When challenged by Pharisees, Jesus replied, “You brood of vipers! How can you speak good, when you are evil? For out of the abundance of the heart the mouth speaks” (Matthew 12:34).
Scenario of Application
Christians can apply this question in many settings to challenge others to think about likely contradictions in their thinking. When the chief priests demanded an account of authority for Jesus cleansing the temple, Jesus responded, “I also will ask you a question. Now tell me, was the baptism of John from heaven or from man?” (Luke 20:3–4).
For instance, when someone challenges Jesus’s command for baptism to become a follower of Christ, you can ask, “How can you say that you became a Christian by saying the sinner’s prayer when Jesus taught to make disciples starting with baptism?” You can further respond with: “I did not become a Christian that way” and then reveal how baptism is the start of the Christian life. Then you can tell them how God raised you from burial in baptism to walk in the newness of life (Romans 6:3–5). If someone claims that baptism is not essential in becoming a Christian and starting the Christian life, then we can return to the question, “Why do you say that?” or “How can you say that when every convert in the Book of Acts was baptized immediately?” They may assert that baptism is a work. Again, we can ask, “How can you say that baptism is a work when the Bible does not say it is work, Jesus commanded it, and no one baptizes oneself?” The Christian can eventually ask an ultimatum like: “How can you say that baptism is not essential to starting the Christian life when Jesus and His apostles taught Christians to submit to baptism by faith and repentance?” A question as an ultimatum is a good conclusion to leave someone with a challenging thought.
Open the Door for Evangelism
In teaching, Jesus asked the most essential and challenging questions. All Christians should answer these questions and ask others the same. After Jesus asked His disciples about who the people thought He was, Jesus asked, “Who do you say that I am?” Peter responded, “You are the Christ, the Son of the living God” (Matthew 16:16; cf. Luke 9:20). Christ encouraged the right answer, “Blessed are you, Simon Bar-Jonah! For flesh and blood has not revealed this to you, but my Father who is in heaven” (Matthew 16:17).
As the church of Christ, we should imitate Jesus by asking “why?” and “how?” questions that will draw out the thinking of others or cause them to pause and reconsider. These questions lead everyone to ask the greatest question: “Who do you say that Jesus is?” All of these questions open the door for others to think about God and Christ and even lead to telling the message, the hope, and the enacting of Jesus’s death, burial, and resurrection. Remember the apostle Paul’s words: “Walk in wisdom toward outsiders, making the best use of the time. Let your speech always be gracious, seasoned with salt, so that you may know how you ought to answer each person” (Colossians 4:5–6).

Let’s join hands to evangelize the true Gospel here in Kenya, it’s highly needed to escape Denominationalism.
Excellent advice. This should be in church bulletins everywhere. It’s easy to get into Bible studies if you ask questions. When I talk with someone whose family has experienced a terrible tragedy, I ask, “How’s your faith?” They always say, “Not good.” Then I tell them they don’t have to blame God because Satan is out there. There are so relieved; they forget Satan exists. Anyway, just one example, but not as good as yours.