What are some spiritual conversation questions that might lead to deep spiritual discussions in your personal evangelism?
Here are 5 as written out in Organic Outreach for Ordinary People: Sharing Good News Naturally.
The following is directly quoted from page 190.

Here are some questions that could move your conversations with nonbelievers to deeper levels of spiritual interaction:
1. What are some joys you are experiencing in this season of your life?
Most people would love to share about the good things in their lives, but they are afraid that others won’t care. Just by asking and listening, you open the door for great interaction. Also, if there are clear signs that God is blessing their life, you could open the door for conversation about the source of all good things.
2. What challenges and struggles are you facing?
People will share their pains and hurts with someone who truly cares about them and takes the time to listen. As they share, you may find that it becomes an opportunity to minister the grace of Jesus. Sharing struggles can also create space for you to pray for or with them.
3. What is your personal history when it comes to faith and God?
This question is not so much about what people believe as it is about their personal histories.
A person might say, “I have no history when it comes to religion,” or “I grew up going to Mass every week and my parents are quite devout,” or “I have always been very spiritual and I still read my horoscope daily and do a lot of meditation.”
No matter what answer they give, you end up learning something about their journey that may allow you to move the conversation to a deeper level.
4. What do you believe about God?
With this question, we move into more personal convictions and beliefs.
Again, no matter how they answer, remember that you are learning and already going deeper than a typical conversation.
Some Christians feel pressured to correct “wrong thinking” or “errant theology” in their conversations with nonbelievers. Try not to do this.
Just listen and learn where they are; then you’ll gain a sense of where they still need to go on their journey toward Jesus.
5. What is your perception of Christians?
Or put a different way, “What is your perception of Christianity or of the Christian church?” It takes courage to ask this question, listen, and not get defensive. But I have found that it can be an open door to deeper conversations.
Taken from Harney, Kevin G. (2009-09-29). Organic Outreach for Ordinary People: Sharing Good News Naturally (pp. 191-192). Order your copy from Amazon by clicking the affiliate link and Amazon will pitch me a few pennies.
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