How to Become a Better Conversationalist

To be interesting, be interested

Midjourney/prompt: “two friends having a really good conversation, watercolor”

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There are certain questions that demand direct answers. When your boss asks how long a project will take, they want you to set a hard deadline. Only a specific date will suffice. 

But sometimes when someone asks you a question, they don’t really care about the answer. What they actually want is for you to tell them something interesting. They are fishing for your best material, each question a line cast in hope of hooking whatever lurks in your secret depths.

So, instead of answering their question directly, tell them the most interesting thing the question makes you think. Surprisingly often, they will respond in kind, and your conversation will spiral into fascinating new territory.

Reel them in, that they may reel you in.

Why should you care about getting good at conversation? I’m a novelist, so I tell stories for a living. But what you might not realize is that whether you’re a founder or an engineer or a marketer or an investor, you also tell stories for a living. To persuade anyone of anything—that they should invest in your startup, join your team, buy your product—you have to earn their attention and their trust. Your influence scales with your storytelling ability—with how interesting you choose to be.

Remember that one high school teacher who cared so much about what you thought was going to be a boring subject that they made you care about it, too? One way to be interesting is to be interested, so when telling someone something you think is interesting, make sure to show them why you find it so compelling, and your enthusiasm will become contagious.

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Marketing executive Noah Brier is something of an expert on finding the most interesting angle about a news event, a cultural trend or artifact, a study, or a place to visit (just to name a few), as documented in Why is this interesting?, the daily newsletter he co-publishes. “Interesting people are also interested people,” he says. “They’re curious about the world, open to new ideas and connections, and fun to be around and talk to.”

I’ve given and attended a lot of talks at a lot of conferences, and one experience stands out—better than anything I’ve seen or participated in at major venues like SXSW or Comic Con. It was a four-person panel that the organizers had hidden away in a basement theater. My expectations were low. But one of the panelists was a professional oral storyteller, and by a stroke of luck or genius, the moderator addressed the first question to her.

Instead of answering the question directly, she told a story that explored the question’s theme. The audience was riveted. Then the moderator asked me a question, and I realized I needed to respond with a deeply felt anecdote of my own. The other panelists followed suit, and instead of debating theses or talking points, we shared stories, each narrative sparking the next. By the end of the panel, people were in tears. I’ve never heard better audience questions, or been so moved by what strangers shared when the event ended and they crowded the stage.

That experience revealed another way to be interesting: package ideas in stories. Skipping straight to the punch line ruins the joke, and morals don’t stick without parables. Wrapping your idea in narrative enables others to engage with it more deeply, understand it more fully, and remember it later. So instead of diving into a direct explanation, tell a story that embodies the truth you want to communicate. Like enthusiasm, storytelling is contagious, and soon you’ll be trading insight-laden tales.

Conversely, when you ask a question, rather than seeking an explicit answer, challenge yourself to use the question as a prompt to elicit the most interesting possible response from your interlocutor.

The most interesting response should surprise you, so there’s no way to know what you’re looking for in advance. Because you can’t plan ahead, you need to bring your full attention to bear in pursuit of anomalies, stray threads in their psychological tapestry. Conversations with Tyler provides an instructive example. What distinguishes it from the thousands of other interview podcasts is the raw potency of curiosity that Tyler Cowen focuses on his guests—his enthusiasm for learning stokes yours.

Beware canned responses. People with media training are the worst offenders, but everyone has ruts they fall into, anecdotes worn smooth by many tellings. Autopilot is great for taking you to familiar places, but not at bringing you somewhere new together. Good conversationalists are like paleontologists digging for each others’ fossils, revealing their hidden worlds to each other.

It’s not enough to care—you also need to show that you care. In 2020, scientists recorded 1,656 conversations between strangers. The volunteers rated their partner’s conversational acumen. As researcher Saloni Dattani summarized the findings, “People who were rated higher by their conversational partners tended to speak fairly quickly, and with more emotional intensity. Also, they tended to use more head movement (nodding for yes and shaking for no) while listening, and showed more facial signs of happiness.”

Conversation is a skill, and fabulous rewards await those who cultivate it. You’ll learn faster, and empower others to do the same. Everyone will want to introduce you to their friends, so you’ll increase your exposure to serendipity. And anyone who finds you sufficiently interesting will look you up to find out what else you’re doing and how they can get involved.

You don’t need to host a podcast to get good at conversation. Each of us is forging our own path through the vast expanse of the unknown, so each of us has a unique vantage. Sharing your discoveries enriches everyone, and helping others share their discoveries enriches everyone further, catalyzing new growth.

If growth is the natural outcome of good conversation, and good conversations consist of telling each other interesting things, then interestingness is the key to bringing out the best in yourself and others. Therein lies its power. So follow your curiosity. Teach what you learn. Aid and abet fellow travelers on the path to progress.

Now, tell me something interesting.


Eliot Peper is the author of 11 novels, including Bandwidth, Cumulus, and, most recently, Foundry. He also works on special projects helping founders tell stories that empower the people they seek to serve. The best way to follow his writing is to subscribe to his newsletter.

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@emilysinsight 10 months ago

I am expert at all of this.

@1greenlaw1951 10 months ago

What is the quickest way to find out what the person your talking to cares about?

@vnmukund 9 months ago

Sometimes, conversations become a one-way traffic. People are eager to share stories, but unwilling to listen to others' stories. Patience and empathy are the key to create enriching conversations.

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