How to Have Great Conversations

Hint: it's about taste

Photo courtesy of Gareth Ellis

Deep, eager conversation is one of the treasures of human life. It’s impossible to have too much of it. It’s like water. Except water can kill you, and conversation can’t.

I’m endlessly fascinated by good conversations. Not just the content of them, but how and why they happen.

Adam Mastroianni said that good conversations have lots of doorknobs. Lots of different doors you can open to see what’s inside. Lots of pivot points.

If you watch someone who struggles with conversation, you’ll probably notice the following tendencies:

• They ask very simple questions.

• They only ask questions, without offering much in return.

• They only answer questions very directly, without providing further stories or commentary or anything else to grab onto.

Some people just aren’t good at creating or using doorknobs in conversation; they’ve never been trained in this particular art. They don’t know how to keep the natural give-and-take, the natural exploratory nature of conversation going.

For one example, a lot of men’s biggest complaint about dating apps is that the women they keep matching with are insanely boring. All they do is answer questions — they make no actual effort to form a connection.

Hey how are you doing?

good hbu

Pretty good, I just got off work. Gonna get a shower and then play guitar. What are you getting into tonight?

not much tbh

puke

And of course this also happens to women on dating apps, or anywhere else where there are boring men. Which is everywhere.

There are boring people everywhere.

This is one of the 60 reasons I gave up on dating sites, years ago. The entire process was hideously demoralizing. Not only is it impossible to have a real conversation through text messages, but this process taught me that most people just aren’t good at conversation to begin with.

Which is weird, because if there's one place you should be trying extra hard, it's on a dating site. But I regress.

Beyond the simple, everyday level of conversation, of flirting or getting to know someone, there’s a level of conversation that has the potential to get extremely interesting. This is the level of conversation you get on great podcasts, or in late-night talks with a loved one, or those first few times you got unbelievably high as a teenager. The kinds of conversations where you actually come up with new ideas (or new levels of intimacy, or new emotions) that you didn’t have before.

Many people are not capable of thinking up new perspectives and coming up with new ideas as they speak, in real time. At least, not on any sort of consistent basis.

But some people are. The mark of a good podcaster, for instance, is that they're not just asking run-of-the-mill questions that any high schooler could ask.

If you're a rookie interviewer, you might ask questions like, “How can I make money investing?” And let's just be honest, that question sucks. It just absolutely sucks. It's not interesting, it's not fun to answer, it's not specific, it doesn't push you into new territory. It's been answered probably a billion times, with a B.

A good podcast host is engaged in novel conversation with a person where they challenge the guest in new ways. They get the guest to say strings of words they've never said before.

That’s a good litmus test for a podcast host: they are great at what they do if and only if their guest keeps saying things they’ve never said before. Or, better yet, that no one has ever said before.

So what’s the hidden ingredient? What does an excellent podcaster, or an excellent conversation partner, have that a mediocre one doesn’t have? Well, you could just say “interviewing skills,” but that’s too vague to be useful. That could include skills like “prompting certain kinds of responses,” “getting out of the way and letting them have the floor,” or “asking very personal questions.” Pretty vague.

Or it could include a skill like “knowing where to go next — knowing what will be interesting.” And another word for that is taste.

What does taste mean, on your tongue? To discern, to distinguish. That’s what it means in conversation. It means using your knowledge, experience, and values to decide what you do and don’t like. That's also what Rick Rubin does in the recording studio, and he's been obscenely successful as a music producer.

So take a 24-year-old for instance: he probably doesn't have much taste compared to someone much older. A 24-year-old, generally, will have more trouble asking interesting questions or provoking interesting answers in an interview setting. And he probably won’t put together many new, fresh ideas in real time.

Why? Because he hasn’t had time to develop taste across many areas of life. He doesn’t have the combination of knowledge, lived experience, and cultural understanding to be able to go new directions with what’s on the table. And, a lot of the time, he doesn’t have sufficiently developed taste to even like or dislike something. He waits for cues from others — especially if he’s interviewing somebody he admires.

When I was 12, 14, 17 years old, I would sit around the table at family gatherings trying to participate in after-dinner chat. The adult conversation was what I aspired to — it was where I wanted to spend the evening, sipping coffee and telling stories and discussing the world.

It seemed so sophisticated to me. And, for the most part, it is. I was right about that.

It wasn’t often I’d have something to add. Because I didn’t have much in the way of taste to be able to take the conversation a certain direction. I had to earn my chops very slowly over time. Most of what we do, when we’re kids, is learn what is or isn’t good from the adults we listen to. It isn’t until later that we learn enough to decide for ourselves whether we retroactively agree, or we’d like to change our minds.

Young interviewers, star-struck as they usually are, have a habit of deferring to the judgment of their subject. They auto-agree with everything the subject says and act like it’s not only interesting but that it must be correct. After all, this person is an expert. Right? The problem here isn’t people-pleasing; it’s a lack of taste. If an interviewer fails to push back against questionable or confusing ideas, it’s often not because he doesn’t want to be confrontational; it’s because he doesn’t have the knowledge or the value judgments to push back. He literally can’t.

For instance, if a random college student tries to interview a nuclear physicist about progress in his field and about how he determines which projects to work on, the student probably won’t be able to say anything in response other than “oh, cool.”

And then he’ll ask the next question. That makes for very dry interviews. Which is why interviewing, as a profession, is only remotely interesting if you’re really good at it. Like Dick Cavett or Nardwuar. If you know a ton about a ton, and you can make decisions about where to go next.

In contrast, a 65-year-old has a higher chance of having developed taste. Of having unique things to say and being able to make judgments. Even if not about nuclear physics, about more things in general — and hopefully plenty of things in particular.

As you age, you naturally develop taste. And it’s exponentially increased, the more life you live per unit of time. The more of the world you absorb.

In between these two extremes, the 24-year-old and the 65-year-old, are the questions, How many books have you read? How many research articles have you read? How much have you experienced in life? How many interesting people have you spoken to? How many risks have you taken? What kind of art have you absorbed in your life? What kinds of love and pain have you felt?

And as you develop yourself in these ways, you develop an ability to pull from that huge pile of stuff in your head and run tiny experiments in real time with new thoughts. You can evaluate the quality of new ideas you stumble across together, and you can quickly make decisions about which doors to open next. When you’re young and uneducated, everything you encounter is brand new. You can’t make value judgments when basically everything in your head is brand new. It hasn’t had the chance to stand the test of time yet.

But as all those bits of information and knowledge and culture in your head do stand the test of time, you become able to use them. To run tiny experiments with them. To evaluate quality.

A good conversation, therefore, doesn't just have lots of doorknobs — although it definitely does have that. It also has tons of places where the participants can get very specific with what they agree or disagree with, what they like or dislike. It has tons of places to get specific.

And that you can't fake. You can't fake getting specific. That has to be earned.

As a side note, this is also why I think anybody who takes himself seriously should avoid using generative AI. If you build art or a reputation using the input of AI, eventually you're going to have to talk about your work. And at that point it's going to become painfully, humiliatingly obvious that you don't actually know what you're talking about — that you didn't arrive at your own conclusions, you arrived at someone else's. Art and reputation, like wisdom, must be earned.

When two people sit down and they each have a developed sense of taste, there is virtually no limit on the places they can go. The only limits are a) time, and b) the fact that you have to choose one thing to talk about.

And great conversation is not just choosing what to talk about, or creating unique insights about those topics. It's not just answering questions. It's also a sense of what’s important and what to focus on, within those topics and questions. Even choosing a different angle to approach a subject from, because you know what’s important and you know how to highlight what’s important in a compelling way.

For example, a great conversationalist has a lot of stories. Because stories highlight what’s important. And this doesn’t mean a great conversationalist has necessarily fought with the soldiers of Sparta; it just means he knows the story. And he knows what matters in the story.

Or for another example, if you're interviewing somebody about writing, you might ask “what does it mean to you to have writer's block?” The person might then say,

Well, let me reframe that by answering the opposite question. What does it mean to not have writer's block? What are the things that are going well when I'm writing a lot?

1. I'm dedicating time to it. I'm doing the work.

2. I'm ingesting a healthy diet of art and information — I'm feeding myself ideas.

3. I'm taking a lot of walks.

4. I'm making time to sit quietly without any stress.

5. I'm taking risks with ideas — I'm not sticking to what's safe and comfortable.

So to answer your question, writer's block to me means that one of those things isn't working or I'm not doing one of them.

In this way, a great conversationalist doesn't just have good answers to questions — he actually has the ability to actively re-frame things. To turn a good question into a great question, and answer that instead.

And then, beyond the 24-year-old and the 65-year-old, you have polymaths and world travelers. With these people, you will not likely ever run out of things to talk about.

Whether you're talking about modern theories in physics, or the history of music, or meditation, or current events, they will immediately have places to go with any of these ideas based on what they do and don't like. What they do and don't value, where they do and don’t think culture should push next.

That’s an interesting person to talk to. Even if you don’t agree with them. That’s a much more exciting conversation than asking and answering questions.

An illusion you might have about conversations, is that asking tons of questions and letting the other person do all the talking is a good thing. Well, yes and no. Will that make other people appreciate you? Yes. Will it make them feel seen? Yes. Will it make them feel like they're special to you and like you value them? Yes.

That’s the How To Win Friends and Influence People strategy. It’s a validation of the other person: sort of being manipulative to gain people’s favor.

But will it make for interesting conversation? Probably not. Those are two very different things. And, frankly, if you're talking to truly interesting people, they probably just see “talking about themselves” as a waste of time. They'd rather be having an interesting chat and learning something new; short of that, they'd rather just stand up and go work on something interesting.

It’s not enough to be smart. Knowledge and intelligence don’t make for great conversation. A smart person who sits in his house all day long is not very likely to have depth of taste. Because all he’s done with life is thought about it. You have to go live it — then you can talk about it. And you should, as often as possible, forever.

Drink some water (but not so much that you die).

JR

“Big ideas come from the unconscious. This is true in art, in science, and in advertising. But your unconscious has to be well-informed, or your idea will be irrelevant.” - David Ogilvy