The art of conversation

At work the other day, I ended up talking to some people whom I don’t usually talk to that much, and I was struck by just how good some people are at turning small talk with a stranger into a nice conversation.

I normally tense up in these situations as workplace conversations often probe places I don’t want to go, expect me to overshare, or are simply vapid — I don’t care about some TikTok influencer or Emily in Paris.

Part of having great conversations is natural talent, much like charisma. But I suspect most of us can at least get better at conversation.

A good start is this guide to better conversations:

I used to think that the way towards more genuine conversation was advancing the schedule of intimacy instantly by plunging into difficult, weird, or controversial topics, usually by asking some intense question, like, what are you most afraid of.” I think lots of aspiring conversationalists—especially men—do this when they’re new to intentionally cultivating human connection. Essentially, this approach treats people’s barriers as a problem to solve. This is stupid.

Some people get frustrated with small talk because the words themselves are not enlightening. But they’re focusing on the wrong thing. The spoken content of small talk is, it’s true, mostly vapid. However, the relevant information underneath the spoken content is fascinating if you learn to care about it. What you’re doing is mutually establishing tone and finding boundaries. You’re getting a sense of the person’s mood, energy level, vibe, willingness to talk to you, style of talking, and so on, and they’re getting the same from you. Also, it’s a basic sanity check.

This exploration of topics and boundaries, while monitoring feedback from your interlocutor is so critically important. There are a few people in particular that I often have to talk to, who simply don’t do this. I get the feeling they’ve listened to a podcast about how to have conversations”, go through their invasive questions like a checklist, all while ignoring any feedback from the person they’re talking to.

The best invitations are usually casual and vague, if you’re at the stage of a conversation where you’re establishing a connection, which can be anywhere between 2-15 minutes in. Say more” and care to elaborate” are magical phrases. You can also repeat what they said. Work has been crazy lately.” Work has been crazy lately?” That can do a lot. The question why is that important to you,” while more intense, can get you really far, really fast, if you sense a mood of openness, especially if you learn to ask it casually.

One catch here is that you have to actually want to know. If you’re saying these phrases idly, your invitations will come across as robotic and false. Sometimes I don’t want to know, sometimes I find myself at a party and am too tired to absorb the joys and sorrows of other people. So then I go home instead of doing any of this, or maybe dance instead.

That true curiosity is often lacking. All too often, conversations go through a 30-second phase of is this more interesting than my whatever’s on my phone” and then it’s over.

That whole article is worth the read.