Skip to main content
Pre-order my book, Think Like a Rocket Scientist, and get amazing bonuses worth 10x the cost of a single copy
Tell me more

3 counterintuitive ways to excel in conversation

Posted in the following categories: Life Lessons, Personal Development

In last week’s article, 3 Ways to be Insufferable in Conversation, we met a fictional character named Jack.

Jack is a master at turning conversations into a one-person show where he always sits in the spotlight. I put Jack together—like Frankenstein’s monster—from various people I’ve encountered in life (including my own conversational blunders). Many of you wrote back saying you recognized your uncle, your mother-in-law, and yes, yourself, in Jack.

It’s one thing to be aware of these conversational flaws. But it’s something else entirely to change them.

It wasn’t until I launched my podcast over a year ago that I seriously started to invest in improving my ability to hold a conversation. My early episodes make me cringe. I still have plenty of room for improvement.

But over the past 50+ episodes with world-class athletes, authors, and entrepreneurs, I’ve discovered three principles that can help anyone excel in the dying art of conversation.

Here they are.

1. Listen with this one goal in mind. 

Last year, I attended a party where a celebrity—who shall remain unnamed—was present. I mustered the courage to walk up to him and introduce myself. He took an interest in my academic work and asked me about my recent publications.

I explained to him the central argument in an academic book I had published the year before. I was a bit starstruck, so I started to ramble and felt his eyes glazing over. I assumed he was feigning interest and being polite. When someone approached us to say hello, I heaved a sigh of relief.

But instead of steering the conversation into non-academic territory, the celebrity said, “Meet Ozan. He wrote a book on . . .” and proceeded to describe the book.

But he didn’t just describe the book.

He pitched the book. He tantalized the other person with the book. He took my dry description of the book and made it fascinating.

I was blown away.

When I walked away from the conversation seriously questioning my copywriting abilities, a few things stood out to me.

The celebrity didn’t say anything about himself.

He didn’t tell any jokes.

He didn’t make a witty remark.

Yet he blew me away. With a simple 30-second summary of my book, he seemed to say: I see you. I hear you. I understand you. I find you interesting.

After that encounter, one thing became clear to me: We don’t have a conversation problem.

We have a listening problem.

Conversations feel like a “competitive sport,” as one Inner Circle member put it during our discussion on last week’s article on the private forum. In conversations, we try to one-up each other with the better story, the better example, and the better “woe is me” anecdote about our lives. We spend too much mental energy thinking about the next clever thing to say.

Put differently, most of us wait to talk. But the best conversationalists listen.

And they don’t just listen. They act as the celebrity did and listen with the goal of summarizing and highlighting what the other person said.

There’s so much noise in the world. We’re all pining to be heard. If you can make your conversation partner feel heard, you’ll foster a deep connection that will persist long after the conversation is over.

2. Say these three magic words.

When I first started my podcast, I ignored all the advice I’m shelling out here.

I would pose questions to my interviewees, but once I got an answer, I would bring the conversation back to me so that I could “contribute” and feel significant.

Now, when I’m tempted to interject with my own seemingly brilliant contribution, I tell myself to shut up. Instead of talking, I say these three magic words:

Tell me more.

Here’s the thing: The first response we get from our conversation partner is often the most obvious one. As the author William Deresiewicz explains, “my first thought is never my best thought. My first thought is always someone else’s; it’s always what I’ve already heard about the subject, always the conventional wisdom.”

To dig deeper, you just need three words: Tell me more. Or if you’re into brevity, these two will also do: What else?

A far more interesting, and far less superficial, answer is guaranteed to follow.

When I first started using this approach, I wasn’t sure if it would work. I feared that if I didn’t share my own brilliant ideas—if I simply asked questions and dug deeper into the other person’s answer—the other person would think I was a dud.

It’s the opposite. When I let the other person shine, instead of trying to grab the spotlight, they come away with the impression that I’m an amazing conversationalist.

The first time I tried those three magic words in a podcast interview, my guest took a minute to thank me after we stopped recording.

“That was a riveting conversation,” she said.

Beyond asking questions, I barely said a word,” I thought.

3. Ignorance is bliss.

If you study world-class journalists and news anchors, you’ll notice that they ask lots of seemingly dumb questions.

Consider the approach of Bob Woodward, the legendary journalist who helped expose the Watergate break-in. Woodward would ask “others almost embarrassingly fundamental questions, which made him sound completely uninformed.” But there was an upside: “Because Woodward hadn’t signaled any clear line of inquiry, people were more likely to reveal something he didn’t know he was looking for.”

Many of us already feel inadequate in life, and admitting ignorance seems to confirm that fact publicly. Instead of acknowledging that we don’t know, we pretend to know. We smile, nod, and bluff our way through a makeshift answer.

Yet the uninformed questions are often the best ones. These questions give other people a chance to showcase their expertise. And they give you a chance to learn something that you didn’t know.

Malcolm Gladwell traces his conversation skills to his father’s inclination to ask dumb questions: “My father has zero intellectual insecurities. . . . It has never crossed his mind to be concerned that the world thinks he’s an idiot. He’s not in that game. So if he doesn’t understand something, he just asks you. He doesn’t care if he sounds foolish.”

The secret of the best conversationalists isn’t conviction.

It’s curiosity.

The Contrarian Handbook
Reimagine
The Status Quo.

Get a free copy of The Contrarian Handbook (PDF and audio) and weekly strategies to innovate your thinking.

We hate SPAM and promise to keep your email address safe.

Add a Comment

Development Alchemy + Aim