How to Have a Great Conversation With Anyone, Anywhere
When I let small talk with strangers spiral into something deeper, it became a book about memorable interactions. Here’s what I learned.
The best conversations crack us open. They leave us tender and reeling, alive again with possibility, mesmerized by the uncanny nature of things. When you really “get there” with someone, you reach what my friend once referred to as the wilderness. You may not know where you are anymore, but you know it’s a place of mystery and beauty. You know you want to keep going. I felt this most acutely a few years ago when I kept having unexpected interactions with strangers. I wrote a book about those experiences — No One You Know, which is very much a chronicle of surprising conversations. There may not ever be an exact map, but thinking back on them now offers a few clues at how to reach that wilderness.
Subdue your chauffeur
Conversation is such a fundamental part of everyday life that we all rely on highly skilled autopilots, or “chauffeurs,” as Christopher Isherwood called them, to tow us through situations. That’s the part of you that kicks in to engage without having to think or really pay attention. The chauffeur can offer up your most well-worn stories and get a laugh by telling a favorite joke but when they’re driving, you’re not really present. While an element of repetition and disengagement is necessary for us to get through some conversations (and maybe even an essential part of being a person), it can be problematic when you’re seeking something deeper or different. Step one is to start noticing that you do in fact have a chauffeur. How often do you let them drive? Is it happening more and more? Perhaps it’s time to confront your chauffeur and hurl them out of the car. Take the wheel.
When you talk about the things you always talk about, you’re going to end up with a conversation you’ve had before. The same old terrain. Instead, seek the side roads. Give voice to a random thought or theory you’ve been turning over recently (ex: “I’ve been noticing that I produce different types of writing when I write longhand as opposed to typing”). Bring up something noteworthy…