How to Become a Better Conversationalist

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.

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.