I’ve recorded a lot of conversations over the past decade — and started my Open + Curious project to explicitly write down what I think I’ve learned. The advice everyone gets about conversation — be warm, follow up, build rapport — doesn’t fully describe what I’ve actually seen happen in the conversations that worked.
This thread is a path through pieces I’ve written and conversations I’ve distilled, sequenced for someone who’s wondering why so many attempts at meaningful conversation fall flat. As usual for my writing, none of them answer the question. Instead, they name some of the gaps between what we usually mean by good conversation and what’s happening when a conversation is actually good.
Listening
constantine.name — March 2021
As opposed to listening to refute, or listening to respond. I keep coming back to this distinction — most of what passes for listening in conversation is one of those two, and neither produces the third thing. Start here, because the rest of the path assumes the distinction.
Be the hornet?
constantine.name — March 2021
The fly on the wall versus the hornet in the room. I started recording conversations trying to be the fly. After enough of them I realized that the conversations I most enjoyed — and that listeners responded to — required me to be the hornet: actively leading, even just suggesting by my presence that a sting might be imminent.
The Conversation Before the Conversation
Open + Curious Field Note — with Matthew Word Bain
Matthew names something I’ve felt for years and never had words for: the body’s conversation runs underneath the mouth’s. It’s the channel that determines whether the other person actually opens up. And it’s the channel we have the least conscious control over.
The Conversations You Can’t Reconstruct
Open + Curious Field Note — with Julie Angel
Julie has one test for whether a conversation was good: how did it feel? The conversations I remember as best are the ones I can’t actually reconstruct afterward. Depth, it turns out, isn’t a property of content — it’s a property of experience, and the same conversation can be deep for one person and ordinary for the other.
Generating great questions in real-time
constantine.name — March 2021
The single move I lean on most often: pick two ideas, presume they’re connected, present that connection as a question. Most people focus on finding a question; it’s far easier to make a question out of something interesting. The piece walks through the move and the many complications I’ve tried on top of it.
Conversation as a spectrum
constantine.name — March 2022
I sometimes try to characterize what’s actually varying when conversations differ — direction of flow, tension, durability, privacy, and more. The piece sketches the multi-dimensional analysis I keep returning to. The interesting move isn’t the analysis itself; it’s using our awareness of the dimensions in real time to consciously create the conversation you want.
Self less
constantine.name — September 2024
And go into a conversation purely to serve the other person. Not to demonstrate you care — but rather to actually care, with nothing in it for you. It’s totally amazing. It alters your own life.
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