23 Apr I Saw a NY Times Bestselling Author Live

Here’s What Charles Duhigg Said That Stopped Me Cold.

by Kalika Yap

A few weeks ago I told you I was going to an Entrepreneurs’ Organization event to see Charles Duhigg speak live.

I want to tell you what happened!

About 10 years ago, I met Charles at a gallery event at the Bergamot Station in Santa Monica, right when his first book, The Power of Habit, came out. That evening changed how I thought about behavior, business, and what’s actually possible when we understand why we do what we do.

Walking into this event, I was curious to see how he’d evolved. He looks exactly the same, honestly. A little thinner. But that same energy, that same warmth, that same ability to make a roomful of entrepreneurs feel like he’s talking only to you.

First, How The Power of Habit Was Born

Before Charles got into his latest book: Supercommunicators, he shared the story of his first book. I’d heard pieces of it before, but hearing it again in his own words reminded me why I love this man’s brain.

He graduated from Yale. Then Harvard Business School. And then, to the bewilderment of almost everyone in his MBA class, he decided to become a journalist.

He laughed telling this part. He said Harvard sends out annual surveys asking graduates how much they’re earning. For the next seven years, he landed at the very bottom of that list.

When the New York Times came calling, he made the move. His wife was pregnant with their first child. And he quickly realized a New York Times reporter’s salary was not going to sustain a growing family in one of the most expensive cities in the country.

So he sat down and asked himself a very entrepreneur-style question: what book could I write that people will actually buy?

The answer came from an unlikely source. He had spent time embedded as a reporter in Iraq during the war. There he met a military officer, a compact, intense man who explained his job this way:

“My job is to take a bunch of soldiers and teach them new habits. Because your instinct, when someone is shooting at you, is to run away. But I want to teach you to shoot back.” — Charles Duhigg, recounting a conversation from Iraq

That officer also talked about communication habits. In a war zone, soldiers could call home every night. If they didn’t have healthy communication habits, the emotional strain would spiral out of control. He said the military had taught him everything about changing his patterns, and that discipline had changed his life.

That conversation planted the seed. Charles went home, thought about his own habits, and The Power of Habit was born.

And Then Came Supercommunicators

After sharing that backstory, Charles moved into the work that brought us all into that room: Supercommunicators: How to Unlock the Secret Language of Connection.

He didn’t start with slides or a list of tips. He started with a question.

The Question That Opened Everything

He asked everyone in the room to think about this:

If you were having a tough day and you wanted to call someone, because just talking to them would make you feel better… who comes to mind right now?

Someone popped into almost every person’s head immediately.

Charles smiled and said:

“That person is a supercommunicator.”

And here’s what I love about that. You already know how to connect with that person. You know exactly what questions to ask them. You know when they need encouragement and when they need a harder truth. You are supercommunicating right back to them without even thinking about it.

His point landed quietly and completely. We are all natural communicators. The capacity is already inside us.

“Communication is what has set our species apart from every other species. And the reason it evolved wasn’t to share information. It evolved because it makes us feel connected to each other.” — Charles Duhigg

Think about the conversations you had today. Maybe 10 or 15 percent of them were genuinely about information exchange. The rest? Someone wanted to know how you were doing. Someone wanted to feel less alone. Someone needed to be heard.

What Actually Happens in Our Bodies When We Connect

This is the part of the evening that stopped me cold. I actually put my pen down.

Charles explained that when two people are in genuine conversation, something remarkable happens physiologically.

Your heart rate begins to match the other person’s. Your breathing patterns sync. Even on a Zoom call, the dilation of your pupils starts to mirror each other’s.

And then it goes deeper.

If you looked at two people’s brains during a real conversation, you’d see their thoughts becoming more and more similar as the conversation continues. At a certain point, they become almost simultaneous. One person mentions a concept and the other experiences it in nearly the same way, at nearly the same moment.

He called this neural entrainment. When we’re truly connected in conversation, we begin to think alike. And that shared thinking is what makes us feel genuinely close to another person.

“Neural entrainment is how connection occurs. When we are entrained with each other, we start to think alike, and that thinking makes us feel closer.” — Charles Duhigg

This is why communication evolved. Not just to move information from one brain to another. To create the feeling of being understood.

The Telephone Story, and What It Means for Us Right Now

Here is something Charles said that I haven’t stopped thinking about.

When the telephone was first invented, researchers and journalists published seriously concerned articles.

Their argument: real conversations could never happen over a phone. You can’t see someone’s face. You can’t read their gestures. You can’t hear the full texture of their voice.

And for the first several years, they were exactly right.

People used phones like telegraphs.

They’d call, give a grocery order, and hang up.

Nobody knew how to have a real conversation that way.

But then something shifted. We learned the rules of telephone conversation. Without even realizing it, people began to over-enunciate by about 20 percent and to put 15 to 25 percent more emotion into their voices. Some part of the brain understood: this person can’t see my face, so I have to show them what I’m feeling through my words and my tone.

Now all of us have had real, deep, life-changing conversations on the phone. The technology didn’t change. We learned how to use it.

Charles made the same point about today’s teenagers. If you’ve ever peeked at your teenager’s text threads, you know they contain almost no words. Strings of images. Emojis. Reactions. They are learning an entirely new language for emotional communication, and they are doing it fast.

The problem isn’t the technology.

The problem, he said, is that devices cut down on how much practice we get.

Real connection requires practice. It requires sitting through the awkward first thirty seconds of a conversation. It requires getting comfortable with the unknown. When we spend more time scrolling than actually talking, we lose that practice. And the skill quietly fades.

“Getting practice is everything. If you pick up the phone and make it through those first thirty seconds, you’re going to have a great conversation.” — Charles Duhigg

The Part About Vulnerability That Made the Room Go Quiet

This was the moment I was most grateful to be in that room.

We tend to think vulnerability means crying or sharing our deepest traumas. Charles offered a very different, very specific definition.

In neuroscience, vulnerability is a neural cascade that occurs when you say something another person could judge.

You might not even care if they judge you. You might mention something small. Something personal. Something that reveals a little of who you are. But the act of saying something that could be judged causes you to pay very close attention to how the other person reacts.

And if instead of judgment, they withhold their judgment… or better yet, share something of their own that you could judge in return… something shifts between you. Trust builds. You actually can’t help trusting each other more. That’s how our brains are wired.

“When I say something to you that you could judge, and instead you tell me something about yourself that I could judge, then suddenly we will trust each other more.” — Charles Duhigg

To demonstrate this, Charles did an experiment with the room. He asked everyone to turn to the person next to them and ask this one question:

When was the last time you cried in front of another person?

Most people groaned. This seemed like the worst possible idea. A two-minute therapy session with a stranger, in a room full of entrepreneurs?

And then he timed them.

When he called time, the room was buzzing. People were laughing. Many had teared up. Almost everyone had discovered something unexpected in common with the person sitting next to them.

He asked how many people felt the conversation went better than they expected. Almost every hand went up.

This is what a deep question does. It invites the other person to say something real. And when you receive that with curiosity instead of judgment, and reflect something real back, you achieve neural entrainment. Your brains begin to sync. You feel close to someone you met twenty minutes ago.

That is not magic. That is biology working the way it was always meant to.

The Question Wendy Jaffe Asked That Every Woman Needed to Hear

I have to give a special thank you to Entrepreneur Wendy Jaffe, our Learning Chair for the Entrepreneurs’ Organization Los Angeles chapter. Wendy is the one who made this entire evening happen. She brought Charles to our chapter, and I am so grateful she did. That is exactly the kind of leadership that makes EO LA so special.

Near the close of the evening, Wendy asked Charles something that I thought was one of the sharpest questions of the night.

She asked about the fine line in vulnerability. Specifically: what do you do when you share something personal and vulnerable, and the other person just uses it as a springboard to talk about themselves?

We’ve all been there. You open up, and suddenly the conversation is entirely about them.

Charles said the key question to ask yourself in that moment is this:

Am I sharing this to steal the spotlight?

Or to make the spotlight bigger for both of us?

That one reframe is something I’m carrying with me.

He also said something that I think every woman in that room needed to hear directly.

Research shows that when a man shows emotion in the workplace, he’s frequently seen as passionate and committed. When a woman does the same thing, she’s often seen as weak or incapable.

His response was direct: it isn’t the woman’s job to fix that dynamic. It’s the job of the men around her.

Good communicators create space for the other person to reflect emotions back. That’s not just kindness. That’s what real communication looks like. And the men in our lives, our coworkers, our partners, our sons, need to hear that clearly.

One More Thing: What He Said About AI and Human Connection

Someone in the audience asked Charles about artificial intelligence and whether people can truly connect with AI.

He’d read the studies. Many people have formed what feel like genuine relationships with AI chatbots. Some of those relationships have lasted longer than you might expect.

But here’s what the follow-up research found:

“The relationship lasts at most nine months. It’s not a friendship. It’s not a marriage.” — Charles Duhigg

The reason, he said, is that at some point people stop believing their words have any real impact. In a human conversation, I see the effect of my words on you. I feel the back-and-forth. I feel something when you smile. I feel something when you look away. That exchange is what makes connection real.

With AI, our words don’t truly land anywhere. And eventually, people sense that. Even when it isn’t obvious at first, it becomes obvious over time. The relationship dissolves because one side of it was never really there.

Real connection requires real reciprocity. That’s not a technology problem. That’s just what it means to be human.

What I’m Taking Home

I left that evening the same way I left the Bergamot Station 10 years ago. Full heart. Notebook full of ideas. A renewed sense of why I do this work.

What Charles teaches isn’t complicated. It’s actually something we already know. The person you’d call on a hard day? You already know how to connect with them. You do it naturally.

The invitation is to bring that same quality of presence into every conversation. With your clients. Your team. Your family. The stranger sitting next to you.

That’s what a supercommunicator does.

And you’re already one. You just have to practice.

Your Step-by-Step Guide: Start Practicing This Week

You don’t need to wait for a big event or a perfect moment. Here’s how to take what Charles shared and put it into action starting right now.

Step 1: Identify Your Supercommunicator

Think of the person you’d call on a hard day. Study how they communicate. What do they ask? How do they listen? How do they make you feel? Write their name down and note one thing they do that you want to bring into your own conversations.

Step 2: Ask One Deep Question Per Day

A deep question invites the other person to share something real about their values, their experiences, or who they are. It doesn’t need to be dramatic. It just needs to go one layer deeper.

Instead of “How’s business?” try “What’s been the most surprising part of building your business this year?”

One deeper question per day. That’s it. Notice what opens up.

Step 3: Match the Conversation Type

Before you respond, pause for two seconds. Ask yourself: is this person in a practical moment, an emotional moment, or a social moment? Match where they are first. Then move together.

Step 4: Practice the Looping Technique

After someone shares something with you, try this before responding. Listen fully. Then say: “What I’m hearing is… Is that right?” Let them correct you or go deeper. This one habit makes people feel genuinely heard, and it’s more powerful than almost anything else you can do.

Step 5: Share Something Real

Vulnerability isn’t weakness. It’s the fastest path to trust. In your next conversation, offer one honest thing about yourself. Something small. Something true. Notice what the other person offers back. That exchange is the beginning of real connection.

Step 6: Get Off Your Phone and Practice

Set aside 15 minutes this week to call someone you haven’t spoken to in a while. Push through the awkward first 30 seconds. The conversation waiting on the other side will be worth it. Connection is a skill, and skills need practice.

Ready to Go Deeper?

If this connected with you, I’d love to meet one-on-one. In my entrepreneur coaching work, communication is one of the areas where I see the biggest shifts. How you show up in a conversation, how you listen, how you make the people around you feel, that shapes everything in your business.

If you’re a visionary woman building a business and you’re ready to lead with more confidence, clarity, and connection, I invite you to book a discovery call with me.

Let’s explore what becomes possible for you.

Schedule Your Discovery Call

I hold space for entrepreneurs who are ready to grow, not just in revenue, but in the fullness of who they are becoming. I’d be honored to meet you there.