How to spark a conversation everyone wants to be a part of

A simple practice for helping more people join in

Jun 21, 2026

By now, you’ve heard me talk about The Art of Middling. Middling is the ability to spark a group conversation that everyone wants to be a part of. Larry David calls it point guarding. Knicks fans call it Jalen Brunson-ing it. I think of it as everyday (even if largely invisible) facilitating, and it is one of the most useful tools I know for holding a group.

You do not always have to middle. In some situations, you absolutely should not. But we are here to expand your range. If you want to widen a conversation and bring more people in, middling is a useful skill to have in your toolkit.

So this week in our Group Life gym, we practiced the art of middling.

The first was learning how to find a Magical Question inside a story someone is already telling. A Magical Question is a question that everyone in your group is interested in answering, and everyone is interested in hearing each other’s answers.

We practiced crafting Magical Questions through real-life scenarios: imagine your friend shares that they were in New York during the Knicks’ championship win, even though they’re not a basketball fan or a New Yorker. The challenge: find the question hidden inside the story that could invite the whole group in.

You flooded the chat with brilliant Magical Questions: “What’s a moment when you felt really in love with the place you were living?” “When was the last time you high-fived a stranger?” “When was the last time you cheered so loudly you lost your voice?”

These questions don’t change the subject; they widen it. They take a story that belongs to one person and turn it into a conversation that belongs to the group.

Come practice with us.

Group Lifers can watch the full replay below. If you’re not yet a Group Lifer, you can become one here for about the cost of a sandwich each month.