Discernment / Exercises

Discernment Exercise: A Toolkit for Conversations

The School of Life (www.theschooloflife.com), headquartered in London and founded by philosopher and author Alain de Botton, offers in their shop an attractive little packet of cards for sale designed to help us be better conversationalists.

“100 Questions: A Toolkit for Conversations”
It isn’t easy to get into a good conversation. Many of our best ones seem to have happened by chance. Far from it—we believe a great conversation always starts with someone asking a great question.
In this set of beautiful cards, you’ll find laid out a hundred of the very best questions around, carefully designed to get a group of people into exceptionally entertaining and meaningful conversations.
100 question cards with box | 150 x 115 x 50mm
Topics include:
Personality & Emotions
Sex & Relationships
Family & Friendship
Work & Money
Travel, Culture & Taste
Life & Death

The School of Life website provides some sample questions from the packet:
What are the best features of middle age?
Do you think other people regard you as a good listener?
Are you where you wanted to be at this stage in your life?
What makes a person a good travelling companion?
What plausible government action would make you leave the country?
What do you imagine people say when they gossip about you?
Have you ever had a religious experience?
If you had married your first boy/girlfriend, what might your life be like now?
What work were you doing the last time you forgot time altogether?

I haven’t ordered the toolkit, but since meaningful and unhurried conversation is a topic of real interest to me, I’ve been thinking about it ever since I noticed the ad.

As readers of mine will know, I have a great deal of respect for Alain de Botton. A committed atheist, he has refused the aggressive fundamentalism of the New Atheists and has instead sought to make common cause with all who seek the common good in society. Instead of trying to score points, he wants to help human beings flourish, and believes his secularism has the necessary resources to make that possible. As a Christian I have doubts about that, but I wish him well—and pray for him regularly.

Certainly the thinking behind “100 Questions: A Toolkit for Conversations” resonates with me. Meaningful conversation is essential to our humanness, and without trying to track down data to back up this claim, unhurried conversation that touches on the deepest issues of the human heart seems to be lacking. Like so much of what is important in life, conversation is not simply natural—at least it isn’t for most of us. Learning to ask questions that are open ended but still authentic, probing but not intrusive is part of growing in wisdom. Learning to listen and being comfortable with silence isn’t easy. Conversation isn’t just an event, but a skill to be learned, an ability essential to community that is vital enough to intentionally nourish over a lifetime.


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?


Source: www.theschooloflife.com/shop/100questions/