Socially anxious? Socially awkward? Always putting your foot in your mouth?

Four tips for conversational success

You’d think that after years of being a journalist, I would have mastered the art of conversation. And yet, I’ve been accused—more than once—of interrogating people. Not on the job, but in regular life. I’ll get curious, start firing off questions, and eventually comes the inevitable: “I feel like I’m being interviewed.” Not meant as a compliment.

Like most people, I also have moments of being socially awkward, or saying the wrong thing, or feeling utterly trapped in a tedious conversation about lawncare or the weather.

We assume good conversation should come naturally. That if we’re smart or curious or socially competent, it’ll just flow. But according to Harvard Business School professor and behavioral research scientist Alison Wood Brooks, that’s a myth. What looks effortless often isn’t. Conversation is a skill—one you can practice.

On today’s episode of the pod, I talk to Alison—who’s analyzed thousands of conversations— about what makes them tick, and why so many of us get them wrong.

Here are four of her most useful tips for making your next conversation go better:

• Prep a few topics ahead of time. It sounds simple, but even 30 seconds of prep—e.g., What might this person find interesting? What’s happening in their world?—can dramatically improve your confidence and reduce awkward lulls.

• Small talk isn’t the problem. Staying stuck in it is. Alison’s research shows people really do hate small talk—but the issue isn’t the topic, it’s getting stranded there. Talking about someone’s lawn might feel like conversational purgatory, but if you follow up with something a little more personal—“Are you happy with where you live?” or “Did you grow up with a yard like this?”—you’re climbing what she calls the “topic pyramid.” The further up you go, the more interesting it gets.

• Don’t “boomerask.” That’s when you pretend to ask a question but really just want to circle back to yourself. You’re better off owning the monologue. People can smell fake curiosity.

• Handle hard moments by softening your stance—not your spine. If things get tense, Alison suggests hedging (“I wonder if…”) or speaking from multiple perspectives to balance both empathy and advice (“As your friend, I get it… But if I were your coach, here’s what I’d try…”). This can help you stay connected without turning it into a showdown.

Just take a minute to contemplate how valuable it would be to improve your conversational chops. It won’t just help you survive holiday parties or awkward encounters with your neighbors. It will help you at work, in your romantic life, in parenting, and on and on. Conversation is the principal unit of exchange in human affairs. And we know from the scientific research that the quality of your relationships dictates the quality of your life. So give this shit a try!

Paid subscribers get a companion meditation to this episode from our August Teacher of the Month, Kaira Jewel Lingo. Today’s is called “How to Be a Good Listener” and is designed to help you show up to your conversations with more presence and curiosity—even when things get tricky.

A reminder: Starting in September, paid subscribers can join us for weekly live sessions. Up until now, we’ve gone live once or twice a month. Now, every Tuesday at 4:00 p.m. ET, you can join a live meditation and Q&A with our meditation Teacher of the Month and/or me. First up: Tuesday, September 2 at 4:00 p.m. ET, I’ll be joined by our September Teacher of the Month, Vinny Ferraro.

Paid subscribers get the 10% Happier podcast ad-free, as well as:

• A cheatsheet for each episode — with key takeaways, time-coded highlights, and a transcript

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Episode Cheatsheet

The big takeaway

Alison Wood Brooks joins Dan Harris to unveil the surprisingly trainable science of conversation. Alison reveals that good conversation isn’t just an inborn gift—it's a skill built by awareness, practice, and strategic choices. From mastering small talk to balancing kindness with self-disclosure, she shares how being intentional in conversation can transform relationships, careers, and everyday happiness.

The science & tactics of meaningful conversation

Key takeaways:

• Conversations are skills, not just talents: Anyone can improve their conversational chops—it’s not just for “naturals.”

• AI-proof your future: In an era where “hard skills” can be automated, “soft” skills like conversation and empathy are more valuable than ever.

• Great conversationalists mix focusing on others and sharing about themselves: It’s about ping-ponging between curiosity and authenticity, not just people-pleasing.

• Small talk isn’t evil—it’s a launchpad: The problem is staying there too long. Move quickly to real, personal topics for deeper connection.

6 practical tips to level up your conversation game: