Wondering questions tend to come in sets of three. Our belief is we are never more than three good questions away from a breakthrough conversation with someone we are trying to build a bridge toward. The key to all good wondering questions is the context they are asked in. We need to pray for a great opening door in order for our questions to touch the hearts of those we seek to connect with. With the right attitude and atmosphere, any of these 99 questions can be powerful tools. The best questions always come from the wondering that the Holy Spirit is stirring inside of you.
Group 1 Life Lessons
A. I’ve made it my life-long goal to learn from others; what’s the greatest lesson you feel you’ve learned thus far in your journey?
B. Tell me about your greatest success and your greatest failure along the way.
C. Would you mind sharing with me the greatest piece of wisdom ever passed on to you?
Group 2 Life Goals
A. What prompted you to pursue your career in _______________?
B. What do you like most about what you do; how about the least?
C. Do you see this as a lifetime career or a stepping stone to something else?
Group 3 Talking About God
A. If someone wanted to talk to you about God, how would you like to be approached?
B. Have you ever had anyone approach you and try to talk to you about God?
C. What kinds of feelings were you left with after the encounter was over?
Group 4 Talking About Evangelism
A. What kind of images or words come to your mind when you hear the word evangelism?
B. The word evangelism means to proclaim good news; why do you think so many people view this word so negatively?
C. Do you know what the good news is that evangelists are supposed to be sharing with people?
Group 5 Talking Career
A. What is your ultimate vocational dream?
B. What stands in your way from achieving it?
C. What advice would you give to a young person just entering the work force today?
Group 6 Religious Experiences
A. What kind of exposure did you have to religion growing up?
B. Why do you think there are so many different religions?
C. Do you think it’s possible for each one to be right?
Group 7 Eternity
A. What conclusions have you come to concerning an after life?
B. Do you think it’s possible to have a degree of certainty about where you will spend eternity?
C. Have you ever taken the time to explore what the Bible has to say concerning eternity?
Group 8 A Good Life
A. Have you ever been able to get a handle on what you think your purpose in life is?
B. Everyone seems to agree that money by itself can not buy happiness; what in your opinion does guarantee a happy life?
C. Where do you feel like you are really winning in life, losing at life?
Group 9 Becoming a Christian
A. In your opinion how does someone become a Christian?
B. Do you think it’s possible to know God personally?
C. Has anyone ever shown you from the bible how to begin a personal relationship with Him?
Group 10 World Events
A. How did 9/11 affect your view of God and the world?
B. When you watch or read the news what conclusions have you drawn about the nature of man?
C. Is there a solution to the social problems like rape, murder, famine, war, racism, divorce, etc?
Group 11 Good vs. Evil
A. Have you ever had an experience where you felt or experienced the presence of evil?
B. Have you ever had an experience where you felt or experienced the presence of God?
C. Have you had any major turning points in life?
Group 12 Barriers to Belief
A. What do you find the most difficult pill to swallow concerning belief in God?
B. It’s been said by the media that Christians are like bulldogs; they have big teeth, a loud bark, but no brains; have you found this stereotype to be true?
C. Would it be fair to say that your disbelief in God is due more to your experience with Christians or with God Himself?
Group 13 Relative Truth
A. It sounds like you value open mindedness, do you ever find yourself closing your mind to certain things, ideas, or people?
B. What criteria do you use when determining something is true or not?
C. Does your world view allow for any absolutes?
Group 14 Marriage
A. How did you meet your husband/wife?
B. What have you learned about yourself through marriage?
C. What do you enjoy the most about marriage/the least?
Group 15 Love
A. Has your understanding of the word “love” changed any over the years?
B. Why do you think so many couples end up falling out of love?
C. If you could pass one secret on to the world about how to keep a relationship going and growing what would it be?
Group 16 Finding God
A. Why do you think so many people prefer to live as if God does not exist?
B. What would you want God to do to validate His existence and bring you to belief?
C. It’s been said that many people never find God for the same reason a robber can’t find the policeman standing on the corner; what does this saying mean to you?
Group 17 Right and Wrong
A. Many have suggested that we are the product of a random evolution. If this is true, why do you think our culture still talks of right and wrong.
B. How do you teach your kids right from wrong?
C. What authority do you appeal to for such teaching in a world that should has no meaning other than what we make it?
Group 18 Dreams
A. What did you see yourself doing career wise when you were 18?
B. What dreams have you let go of?
C. What dreams are you still hanging on to?
Group 19 The Future
A. Are you optimistic or pessimistic about the future of our world?
B. Do you think it’s easier or harder to raise kids in today’s world?
C. What concerns you most as you think about your future?
Group 20 Major Influences
A. Who is the most impressive person you have ever met?
B. Has there been one book/movie that has greatly influenced you?
C. Besides your parents is there anyone person who stands out as having had a major influence in your life?
Group 21 Change
A. God has begun to change my life, have you ever considered letting Him change yours?
B. If God had His way with you what do you think He would change first?
C. What scares you the most about letting God change your life?
Group 22 Taking Stock
A. What 3 principles of life have benefited you the most thus far in your life’s journey?
B. What if anything causes you to be hopeful about your future?
C. Is there anything left undone in your life that would cause you great sadness if you only had 24 more hours to live?
Group 23 Getting to Know You
A. As people get to know you what do they enjoy most?
B. As people get to know you what do they enjoy least?
C. As people get to know you in what area do you feel most misunderstood?
Group 24 Leadership
A. How would you describe your leadership style?
B. What leadership style do you respond best to?
C. Jesus was described as a servant leader what kind of images does that stir up inside you?
Group 25 Direction
A. Why do you do what you do?
B. What life experiences have molded you and motivated you to pursue this path?
C. Would you choose this same path over again?
Group 26 Questions for God
A. If you could ask God any 3 questions what would they be?
B. If God were to ask this one question; are you for me, or against me; what would you say?
C. How would you defend yourself if your response was put on trial?
Group 27 Sex
A. Which sex do you think has the tougher path in life?
B. What do you enjoy most about the opposite sex?
C. What do you enjoy most about being male/female?
Group 28 Hate
A. Have you ever hated anyone?
B. Has anyone ever hated you?
C. Do you think there is a solution for this emotion?
Group 29 Death
A. If you could choose the manner of your death how would you like to go?
B. What would you like written on your tombstone, spoken at your funeral?
C. Does the thought of death scare you?
Group 30 Control
A. It’s been said that life is largely out of our control; if that’s true why do so many people try and control the life they live?
B. Do you struggle with that?
C. What kinds of things do you think can be controlled in life?
Group 31 Habits
A. What kinds of habits do you struggle with most?
B. Do you ever find yourself wondering why you do the things you don’t want to do, and end up doing the things you don’t want to do?
C. Do you think there is anything out there that can set you free from this cycle?
Group 32 Childhood
A. How would you change the way you were raised?
B. What things are you going to do/are you doing as you raise your kids?
C. What values from your childhood do you want to pass on to your kids?
Group 33 Questions for Jesus
A. If Jesus were here right now, what would you ask him for?
B. How do you think he would answer?
C. How would you feel if that happened?