What makes a good conversation

A few years ago, during a retreat with my team, I took part in an experiment I haven’t quite been able to get out of my head ever since. 

We sat in pairs and were given a menu with a few options for starters, mains and desserts. Not a single edible item was found on the piece of paper however. 

Instead, each “course” consisted of a series of questions:  

  • What have you learned about the different varieties of love during the course of your lifetime? 

  • Which parts of your life have been a waste of time? 

  • What have you discovered through travels?

  • How have your priorities changed over the years? 

  • When have you felt isolated or alone and what are your remedies?

We’d make our way through the menu by picking and choosing a question for each course and then discuss it.  

The room immediately started buzzing with animated exchanges. I was learning things about my colleagues I would have never been able to access via daily work chats.

I was enchanted by this method originally developed by Theodore Zeldin. It was a radically different experience of conversation. The questions seemed to hold some sort of magical power, unlocking deep exploration and bonding. What was it about them that made them so good? Knowing surely would be the key to what makes a good conversation. 

The answer, I posit, is simply that these questions interrogate three universal dimensions of the human condition: 

  • What we learn from the past: Life is a succession of experiences. They sit inside us shaping our view of the world. Seldom do we have opportunities to reflect about how we’ve made sense of them, the lessons we’ve drawn. A conversation that enables experiences to rise to the surface is a rare opportunity to tap into each other’s wisdom.  

  • How we cope with the present: From the way we organize our finances to how we decide what to eat for dinner, we all have a system to keep our life on tracks. While it may appear trivial at first to ask someone how they go about organizing their closet, these questions are a fertile terrain for comparing mental models and learning new problem-solving techniques.  

  • How we imagine the future: There’s nothing quite as powerful as our aspirations. The envisaged future is why we do what we do, whether it’s a career breakthrough, a change of destination or the house we will one day build with our own two hands. Questions about our imagined futures are like doors to this magical place where the laws of the present don’t apply. 

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My struggle to answer a simple question

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What I Learned from Parkour