Most conversations between people who’ve just met, or loose acquaintances, are pretty shitty. And it’s not for lack of desire. The majority of people, I think, want to connect with people and open up about something. Almost everyone is full of some vital matter they’d like to express but that exceeds the capacity of the average conversational venue.

Personally, I try to assume that I can make conversations much better and that everyone I speak to could be a friend I haven’t met yet, or, at least, someone who’d like to be seen and understood.

Note that I hold this assumption lightly and am ready to discard it at a moment’s notice. Some people don’t want to talk to you at all and that’s fine. Sometimes people are genial but have no interest in connecting with you on a deeper level, and that’s fine. Sometimes people are so devoted to playing status games that all they want to do is undermine you, or rattle off their accomplishments, and that’s annoying, but there’s not much you can do. The most graceful thing you can do is excuse yourself in any of these situations.

But many conversations can be nudged in the direction of openness, spontaneous complexity, and shared emotionality. And a surprising number of conversations, thus encouraged, can become quite connective. These are the conversations where you’re likely to find yourself laughing, rambling excitedly, engaging in extended weird riffs, crystallizing old knowledge in new patterns, feeling comprehended, feeling loved, and, generally, having the sensation that you’ve temporarily stepped outside the walls around your being.

Good conversations can heal you effortlessly sometimes, too. I think this is at least 50% of the mechanism of action of talk therapy. So you can go around doing that whenever.

I’ve tried hard to figure out how this can be cultivated. It took effort since I’m naturally untalented in this respect. The method of conversation I had for a bunch of my life was babbling about whatever I was interested in until my interlocutor wandered away. That’s how I did things, until I noticed, after a decade, that people don’t like this, and, what’s more, I didn’t like it. When, occasionally, I met people who managed to induce me to have a more connective conversation, I enjoyed myself much more than I would have if I’d set the tone.

Eventually I realized that human connection is one of my favorite things, and thus I’ve tried really hard to override my prior instincts. And I think I’ve done a reasonably good job. I think I’ve gone from “terrible” to “at least better than average,” and my job depends on being able to induce conversational depth with reliability.

Here are some notes from the overriding process. Everything that I’m writing here, I’ve had to learn the hard way. Many emotionally intelligent people will read this and feel like 90% of it is hopelessly basic, and that is okay with me.

Small Talk Is Vital

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. The person you’re talking to, implicitly, is assessing whether you can do basic social norms—in this case, small talk. If you can’t pull it off, it’s probably not safe for them to share anything beyond their feelings about the weather.

You can do this with any small talk question asked with the right attitude. What do you do, how’s life lately, how do you know the host, etc. The initial topic is immaterial.

If you’re in a state of mind where you can’t stand small talk, you might be fixated on your own expression or agenda, rather than being in a state where you’re willing to spend some time on being curious about another person. This is fine, but in this state, you probably want to talk to an established friend who’s already receptive to whatever, rather than making conversation with someone new.

You cannot force good conversations to happen. You have to allow and invite them, and small talk is where you get to the point of extending the invitation.

Extending the Invitation

If small talk is going well, you might be able to increase the depth of the conversation. When I want to do that, what I’m looking for is dormant energy—a sense that we’re near something emotionally important, whether the emotion is positive or negative, whether it’s hovering around an intellectual or personal preoccupation. This isn’t too hard, it just takes a little more observation than is the default.

80% of the time, what you’re looking for is non-verbal, or barely verbal. “I’ve been okay lately,” spoken briskly, could mean nothing. With a pregnant pause, or a little facial tension, this could mean that they’re either totally not okay, or they’re happy and excited but want to downplay it. “Work has been insane lately,” said emphatically, could mean “I’m thrilled about my new startup” or “I’m reevaluating my priorities in life because I’m miserable.”

It’s not necessarily the case that there’s more to be unearthed, or that the person wants to go there. Sometimes people are leaky but don’t want to disclose—the thing on their mind is spilling out, but they don’t want to explore it. So you have to probe gently, and I hesitate to even use the word probe. It’s more like signaling openness. If you signal openness to someone, and they want to open up in return, it’ll happen, you won’t have to try too hard.

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.

This kind of opportunity usually presents itself, since people who are still talking to you will tend to unintentionally fall towards what’s on their mind. However, if this doesn’t happen, you can also try to lead by disclosing your own deeper thing—maybe mention something that’s concerning or captivating you lately, going into slightly more depth. Your conversation partner will either go there with you, or look at you funny and/or offer a shallow response. If the latter, they don’t care to venture onwards with you. Be alright with this.

Right Attention

People love attention, almost more than anything. Part of what makes people open up, conversationally, is the sense that someone is paying them more attention than normal. This is usually conveyed by shared body language, shared speech patterns, and granular responses—like, for an incredibly banal example, if someone tells you they used to live in Paris, you can say “I hear it’s beautiful, do you miss it” rather than, “oh cool.” Generally, treat people as if they’re important, and, if you can hack it, feel that they are important.

But there’s a balance here. Too much attention, that’s too focused, especially early in a conversation, feels weird. It feels like you’re being put on the spot, or like your conversational partner has made themselves subservient to you, or like they’re trying to dominate your mind. I occasionally experience this—it’s not often, but it happens—when I meet someone who’s a fan of my work and thinks the point of a conversation is to impress me, or, worse, to overcome the insecurity they feel when talking to someone whose work they value.

So you want to communicate, to your interlocutor, that you’re sensitive to what they’re saying, paying them close attention and perceiving their nuances, but that you’re not sucking on their every word like a remora. This is signaled in a lot of non-verbal or semi-verbal ways, not limited to:

—Eye contact that’s strong but not mono-focused, modulated, to some degree, to match what they’re doing.

—Your body being directed towards them but not crowding them.

—Inclining towards their cadence of speech but not matching it like you’re trying to become them.

It’s a balance that you feel out, and it’s a mutually created balance: ideally, both people will be engineering a shared attentional space.

Also, read this Ben Kuhn post about being a good listener, and watch this Michael Ashcroft video, which is purportedly about being natural on camera with Alexander Technique, but which is actually about varieties of attention.

When you arrive at a mutually significant subject, and you establish the right attentional space, this funny thing usually happens—the conversation starts driving itself.

Good Silence Is Powerful

A common conversational anxiety is the feeling that you need to fill every moment with sound, otherwise the person is going to get bored and walk away. But good, deep conversations usually contain silences where you can reorganize your thoughts or simply occupy the flow of time together.

You can signal that this is permissible, and thus that your interlocutor has space to relax into, by leaving good silence in a conversation: friendly silence where there’s some degree of maintained eye contact, receptive body language, and so on. Interestingly, I find that it’s often after these brief silences that conversations get profound.

Talk About the Conversation in the Conversation

Something that not a lot of people do, but that seems to work well for me, is noting properties of the conversation within the conversation. This creates a sense of shared space and mutual understanding. “It’s really nice talking to you,” works, or, “I didn’t expect this to get so intense,” or, “it’s great to connect about this,” or “okay here’s a funny question.” You’re pointing out that you’re another human being, feeling similar to how your interlocutor is feeling, which is not always obvious. It’s a dimension of affirmative language that’s one step beyond “I hear you” or “I see that.”

Avoid and End Autopilot

Good conversations often contain moments that, on paper, look like monologues, which is to say, one person divulging something for a period of time, or telling a story. But the key thing is that they can’t feel like monologues.

There’s a marked difference between someone sharing something of emotional importance in a resonant way, and someone talking at you. The difference is attention: whether they’re weighing your reactions and modulating (consciously or subconsciously) their pace and tone to match where you’re at, whether they’re noticing if you’d like to interrupt with a question or comment, etcetera.

It’s pretty easy for cerebral, verbal people to lapse into monologue mode, myself included. The only real solution is awareness. Be aware of the potential and let it go when you’re doing it. That’s all you can do. When I find myself there, I tend to say something like “okay wow I’m talking a lot, what is your reaction to all of this,” and that lightens the mood and brings it back to the present.

You can’t control whether someone else goes on autopilot. But you can make it less likely. Much of the time, people go on autopilot because they feel nervous: they think that to impress you, or earn a place in the conversation, they have to spit out a pre-written cached response, or dwell on the one subject they know something about.

To remedy this, beyond creating a connective environment as described above, you can signal that they’ve already earned your attention. A lot of the time, this looks like prosocial interruption—breaking the flow but in a kind way that makes them feel good (or, you could say, a way that raises their status). If they mention, on autopilot, that they like tactical shooting, you could say, “oh so you’re basically an action hero,” or ask them a question about that, or whatever. This indicates that you’re still interested in them if they go off-script or if the cadence is interrupted: they don’t need to do their song and dance.

Some people are on autopilot most of the time. They talk a lot and it has nothing to do with you, ever. These are pretty much the only people I can’t stand talking to. This often stems from externalized self-suspicion—the ongoing need to defend one’s identity by hurling boilerplate at anyone who will listen. This used to be me, a lot of the time. Most people grow out of it.

Let Yourself Surprise and Be Surprised

Typically, the best conversations are ones that possess some degree of spontaneity. And you can encourage spontaneity. If something floats across your mind that’s unexpected, like a conversational tangent jogs a memory or idea you didn’t foresee appearing, make it part of the conversation. “For some reason, this makes me think of [x]” is fine. Similarly, if your interlocutor says something that seems tangential or off-topic, ask them about it, encourage them to follow that path.

50/50 Is Good

You should be talking about 50% of the time. Not always, and that’s not a minute-to-minute figure, it’s a, say, 2-5m figure. But if the number is way off, there should probably be a good reason.

Some reasons are good, like, the conversation has explicitly become about one person sharing an experience and the other listening. Also, there are some people who are genuinely happier occupying a majority listening role, but this is a very, very small number of people—many conversationalists who are stuck in a listening mode are just getting steamrolled.

Also, if someone is disclosing intimate stuff, matching their level of disclosure, if you’re comfortable with that, if appropriate, is a nice thing to do.

Don’t Leave the Silly Out of the Serious, or the Serious out of the Silly

One thing I think I’m good at, specifically, is talking to people who are depressed or have been through a shitty time recently. And the reason I’m good at this, I think, is that I don’t adopt grave listening face when people are talking about serious stuff, or get falsely reverent. I stay more or less as silly and lighthearted as I usually am. It’s not like I’m flippant about what they’re going through, I just don’t lapse into a false eulogistic mode—I try to meet people halfway.

This comes from experience. During the sad years of my life, when I dealt with varying levels of suicidal ideation for extended periods, I thoroughly appreciated when people kept things light and funny, and didn’t treat me like a leper. It pissed me off when I detected that my comforters were engaging in a rote form of empathy signaling, which is a common mode.

Generalizing this: if your local social code allows, I would recommend gently inclining your current mood towards the mood of the conversation, rather than trying to completely wallpaper over yourself with whatever mood you think might be demanded. The latter tends to come off as condescending and stiff.

Most People Don’t Want to Debate, Usually

That’s about all I have to say about this topic.

Don’t Always Bring Everything Around to Your Story Instantly

Self-explanatory.

Good Conversations Don’t Have to Go On Forever

Sometimes you can feel a conversation ‘click shut,’ like the energy that propels it has been exhausted. When you do, you can just end it, rather than trying to wring more out of it. “It was great talking to you, I’m going to go [perform some action]” is almost never an inappropriate thing to say at this point.

These Guidelines Can Only Go So Far

In a way, this is a slightly silly post, in that I’m flailing at an ocean here. Conversation is a deep and wide endeavor that features a million little micro-skills. A lot of it can’t be abstracted: the non-verbal tacit knowledge, little micro-moves that need to be deployed contextually, qualities of attention that can be gestured at but not fully described, and moves that work for you but not others because of your specific vibe.

So if any of this has been useful to you, understand that this is impoverished conceptual scaffolding, designed to get you closer. You will, of course, have to experiment. The most important thing to understand is that if you apply a smidge more intentionality to conversation than is the default, and you assume that potentially great conversations are everywhere, the human world will open up to you in ways that are hard to imagine or overvalue.

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