1. How would you rate yourself as a conversationalist? How would you rate yourself as a listener? How would you rate yourself as someone able to ask good questions?
2. Describe an encounter in which someone truly listened to you in an unhurried way. How did the encounter affect you? What did the person do to encourage you to speak freely?
3. Do you remember a question that someone asked you that still sticks in your memory as memorable and helpful?
4. What is the difference between using something like “100 Questions: A Toolkit for Conversations” to help you learn to ask better questions, and turning the whole thing into some sort of technique?
5. To what extent do you feel the need to control the direction of conversations? Where does this need in you originate? What does control, or the addition of an agenda on the part of one of the participants change a conversation?
6. A true conversation is open ended and free, an interaction between two (or more) people created in God’s image. To what extent are you comfortable in this situation? Where does your discomfort originate?
7. In conversations, do you tend to be primarily listening as the other person speaks, or do you tend to be thinking of what you should say next? What difference does it make?
8. If the person to whom we speak is to feel free to open up honestly in the conversation they must feel safe with us. Of what does such safety consist? How is it communicated? To what extent is such safety rare—and why?
9. Though I’ve never been able to trace the source, the philosopher Mortimer Adler said, “Love without conversation is impossible.” Do you agree? Why or why not? To what extent does this resonate with a biblical perception of life and reality? If this is true, to what extent do we demonstrate love for the non-Christians—and the Christians—around us?
10. What are the greatest hindrances to real conversation? Are there any hindrances that seem to be particularly present among Christians? Why might that be?
11. Begin your own list of “100 Questions.” Which questions might you keep from the list posted on the website of The School of Life? Which questions might you toss, or edit? Why? Which might you add?