The things [contacts] share reveal something personal about them: encourage this to blossom into a discipling relationship by praying, sharing and asking good questions.

Remember: questions they can answer with a word or two reveal little about them and are not ideal. (This doesn't mean they're "bad" - just that, by themselves, they close off communication instead of opening it up. So they should be followed with something else.)

Some examples: 

  • Let me know if I can pray for you
  • Write me back if you have any questions.
  • Have you been reading your bible?
  • Do you have a good church?

Get them to express thoughts or feelings in addition, or instead.

Here are some diagnostic questions: 

  • If God would do a miracle for you today, what would you ask Him for?
  • For you, what is hard about following Jesus?
  • What has God been showing you in the Bible lately?
  • What is your church like?

Some open-ended evangelistic questions: 

  • In your spiritual belief, is it possible to be sure you have eternal life?
  • Do you have this confidence?
  • Why or why not?
  • To you, who is Jesus Christ?
  • If you suddenly appeared before God and He asked you, "Why should I let you into My heaven?" What would you say to Him?
  • What is the most important thing in life?
  • What is love?
  • Is it possible to know and relate to God in a personal way?
  • What is the thought that brings you the most peace?

Some open-ended questions for discipleship:

  • What do you want the most out of life?
  • What do you spend the most time thinking about?
  • How do you usually use your money?
  • How do you usually spend your leisure time?
  • Whose company do you most enjoy?
  • Who and what do you admire?
  • What makes you laugh?

This message was summarized in an "OM Quick Tips" video:

OM Quick Tips: Asking Compelling Questions

Update, May 2020:

Example questions :

  • What was the best part of your week?
  • What was the worst part of your week?
  • What’s been on your mind most recently?
  • When was the happiest time of your life and why?
  • What are you good at?
  • What are your dreams for the future?
  • If money wasn’t an issue, and you could do anything you wanted to do, what would you do?
  • What were you like as a child- do you think you’re different now?
  • Who in your family are you most alike, and from whom are you most different? In what ways?
  • Who in your family are you closest to, and are you close to your other family members?
  • Who is your best friend, and what is the best thing about them?
  • How would your close friends describe you?
  • Who has had the most significant influence in your life?
  • What would you change about yourself if you could change one thing?
  • What is the most frustrating thing about religion to you?
  • If there was one law you could make, what would it be? If there was one law you could break, what would it be?
  • What causes 80% of your stress?

Some of Vince Vitale’s favorite questions

  • Have you had experiences in your life that made you think there might be a God?
  • Did you grow up in a religious home?
  • (If they express themselves as Christians) Did you come to the faith at an early age, or did you come to it kicking and screaming later on?

Testimony themes

  • Forgiveness
  • Family
  • Suffering
  • Relationship
  • Intellect
  • Dreams
  • Purpose
  • Loneliness
  • Guilt
  • Death
  • Shame
  • Freedom
  • Pride
  • Worry and anxiety
  • Frustrations with the church
  • Decisions about the future
  • Image
  • Identity