Developing Deeper Friendships Through the Art of Asking Questions 

by Evangelist John David Hicks © Faith Encounter, Inc. 1997

“The purposes of a man’s heart are deep waters, but a man of understanding draws them out.” (Prov. 20:5)

“The pleasantness of one’s friend springs from his earnest counsel.” (Prov.27:9)

“A man finds joy in giving an apt reply–and how good is a timely word.” (Prov. 15:23)

“The tongue has the power of life and death, and those who love it will eat its fruit.” (Prov. 18:21)

The great philosophers of history are regarded as wise, not because they knew all the right answers but because they could ask the right questions. Good questions will give you entrance into another person’s world. It’s easier to state the facts or give your opinion than to probe deeper and know the real person. To ask the right question requires you to listen and show an interest in what the other person has to say.

Jesus was good at asking questions. When the Pharisees were on his case for healing on the Sabbath, he asked, “Which is lawful on the Sabbath: to do good or to do evil, to save a life or to kill?” The question set many free and exposed the hard hearts of others. To his disciples he asked, “Who do people say I am?” As he probed their hearts, he goes deeper, “But what about you?”

To the blind Bartimaeus he asked, “What do you want me to do for you?” Not only was he healed–he followed Jesus. By his concern, Jesus made people feel accepted and they opened their true selves to face truth they would not admit before. Good questions go right to the heart of a matter.

In conversation, your thoughts and feelings are important because they represent you and the other person. To be an interesting conversationalist:

  • See the worth and value of that person who is made in the image of God. This is first conveyed by remembering his or her name.
  • Think before you speak, by considering their interest.
  • Your eyes and your enthusiasm will attract and hold attention, even when you differ in opinion.
  • Listen intently, being aware that in every encounter there are emotions involved, maybe even some sense of threat from you. Notice what is said and what is implied. Your openness and acceptance will reduce threat.
  • Knowing what you want to talk about gives opportunity for sharing your vision and purpose before God. The key to good interpersonal relationships is the ability to ask fitting questions that reflect your genuine interest. To be effective, ask your questions without a hint of a judgmental attitude or the impression you might misuse the information. Good questions meet a person’s need for attention and establish rapport as you learn something new about the person. Good questions also give you the right to be heard. Begin with questions for information that are easily answered. Learn the names of family members up front. Then move to questions that draw out their thought. Avoid questions requiring only a yes or no answer. Instead of asking, “Do you like your job?” ask “What do you like or dislike about your job?” Most people want you to inquire about their interests, background, and achievements.
  • Becoming Involved:  Icebreaker Questions. Create opportunities for informal conversation in a comfortable setting by letting the person know you want to be with them. “How about a cup of coffee?” “Let’s go for a walk.” Once the conversation is underway, ask: “Tell me more about it.” “I would like to hear what you think.” “Go on, I’m listening.” “This seems to be something you feel quite strongly about.” “I see.” “What then?” Eye contact, nods, and smiles convey your interest. Occasionally repeat what you hear: “Let me see if I’m hearing you correctly. Are you saying…?” or “So what you are saying is…?” Feedback demonstrates your interest.

Here are some questions from The Book of Questions by Gregory Stock:

1. If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?

2. You discover that because of a mix-up at the hospital, your wonderful one-year-old child is not yours. Would you want to exchange the child to try to correct the mistake?

3. If you could use a voodoo doll to hurt anyone you chose, would you like to?

4. Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash and save any one item. What would it be?

5. While parking late at night, you slightly scrape the side of a Porsche. You are certain no one else is aware of what happened. The damage is minor and would be covered by insurance. Would you leave a note?

6. If you learned that a good friend has AIDS, would you avoid him? What if your brother or sister had AIDS?

7. If you were at a friend’s house for Thanksgiving dinner and you found a dead cockroach in the salad, what would you do? Going Deeper * Opinion and Feeling Questions When you become vulnerable, admitting to others your weakness, struggles, needs and fears, your openness will move you into a deeper level of communication. In Scripture, David, Paul, and Jesus were genuinely transparent, which made them more appealing and credible to others. You might list several questions you wish people would ask you, then ask others those questions. Remember, in intimate conversation, timing is important.

Use these questions as an opportunity to create closeness.

  1. What makes you happy?
  2. What do you feel anxious about?
  3. When do you feel most secure?
  4. When do you feel most alone?
  5. If you could chose any type of job you wanted, what would it be?
  6. Whom do you admire the most?
  7. If you could travel anywhere, where would you like to go?
  8. What one achievement do you hope your children will make?
  9. If someone gave you a million dollars, what would you do with it?
  10. Why are you in business?
  11. What keeps you at it?
  12. What is most interesting about your work?
  13. What in life is most importantto you?
  14. If you were sure you could not fail, what would you attempt to do?
  15. What do you think is the most critical problem in our relationship?
  16. What gives you a feeling of hope?
  17. What would it take to make you feel really fulfilled?
  18. What can I do to help you reach your goals?
  19. If you had one month to live, how would you choose to spend your time?
  20. What is your happiest childhood memory?
  21. What do you feel is the most important factor in having a happy marriage?

Discipleship Questions

These questions develop character by helping a person think through what they are saying and doing.

  1. What are you struggling with?
  2. What are the problems you face down at the office?
  3. If you could live your life over, how would you choose to make it different?
  4. If you could be any person you know or have read about, who would that be? Why?
  5. If someone were to write an epitaph on your gravestone, what do you think it would be?
  6. How would you like to be remembered?
  7. What would you like to do or achieve in the next five years?
  8. What is your philosophy of life?
  9. If you could live your life over, how would you chose to make it
  10. different?
  11. What qualities do you look for in a friend?
  12. What do you think Jesus looks for in choosing a disciple?
  13. What has the Lord been teaching you?
  14. What do you think was God’s purpose in making you?
  15. What were the events that led to your becoming a Christian?
  16. What do you see as the biggest difficulty in living the Christian life?
  17. If you could have one wish right now, what would it be?

When working with a small group or church board, you want to create unity and friendship. Here are some good questions:

  1. As you look over the past year, what significant thing happened in your church or your life (name only one)?
  2. In what area is your Christian life growing right now?
  3. What kind of person are you (argumentative, passive, for example), and what kind of person would like to be?
  4. Who has helped you the most to grow spiritually, and how did he or she do it?
  5. What suffering have you known, and what benefit has it brought you?
  6. Finish Paul’s words, in your words, but do not use Jesus or Christ. “For me to live is…” and “to die is….”

These questions can be used as an icebreaker when you are entertaining a group:

  1. People will think of me as….
  2. Nothing is so frustrating as….
  3. The teacher I liked best was a person who….
  4. The thing I like about myself is….
  5. Tell your life story to another person in one minute. Then reverse it for one minute. Have each person tell his or her friend’s life story to the group.

Witnessing Questions

If you are not sure where a friend is spiritually, ask, “How’s your fellowship with the Lord?” or “How are you doing spiritually?”

These questions are good for anyone:

  1. Do you ever think about spiritual things? Are you interested in spiritual things?
  2. What would you say is a person’s greatest spiritual need?
  3. Has there ever been a time in your life when you thought you needed eternal life?
  4. Suppose someone were to ask you, “What is a Christian?” What would you say?

Some people think they are Christians, but you believe they have never received Christ as their Savior.

Here are questions to ask them:

1. In your opinion, what would you say a person has to do to be a Christian (or get to heaven)?

2. Have you ever thought of becoming a Christian?

3. Have you come to the place in your spiritual life where you know for certain you would go to heaven if you were to die today? Or, if you died tonight, do you have the assurance you would go to heaven?

4. Would you like for me to share with you how I made that discovery and how you can too?

5. Suppose you were to die tonight and, standing before God he said to you, “Why should I let you into my heaven?” What would you say? At the judgment, if God ask you why he should let you in, what would you say?

6. Have you ever heard of the “Four Spiritual Laws”? These spiritual laws govern our life and eternal destiny.

7. I’d like to tell you about a great experience I had.

8. Have you trusted Christ as your Savior or are you still on the way? How far along the way? Would you like to receive Christ as your Savior right now?

9. Could I show you three or four verses of Scripture, to see exactly what God’s Word says about this?

Presenting the Gospel

Here are some closing questions:

  1. Does this make sense to you?
  2. Do you want to receive Christ and the gift of eternal life?
  3. Would you like to repent of your sins and follow Jesus as your Lord and Savior?
  4. The Lord is here right now. Will you pray with me to receive Jesus as your Savior right now? In Romans 10:9-13, God tells us how to be saved. Verse 9: Do you believe that Jesus died for your sins and that God raised Him from the dead? Verse 10-11: When God saves you, will you be ashamed of Him? Would you be willing to tell others you are a Christian? Will you make Jesus Lord and Master of your life and do what God wants, forsaking and turning from your sins? Verse 12: There is no difference–God will save anyone. If he saved one who called on him, he must save all who call upon him. Verse 13: Doesn’t it say, “If you (his or her name) calls upon the name of the Lord… God will save you”? Pray the sinners prayer, then ask the question, “What did God say he would do if you called on him to be saved? “Save me.” “Let’s thank him.” Pray, “Thank you for saving me, Lord. Help me serve you and not be ashamed of you. Thank you for coming into my heart and giving me eternal life. Amen.”


Good questions will help you discover strong points, so you can encourage a person’s hopes and desires. When genuine friendship develops, each person will be more willing to talk freely and listen more deeply. As intimate communication is taking place in a marriage, friendship, or church, the possibility for trust, unity, vitality, and love will also take place.

Approach each conversation as an opportunity to create closeness. God will bless you with genuine friends.


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