The Case for Curiosity

Genuine curiosity might be the most underrated skill in business—and in life.

Not curiosity as a tactic. Not the kind you dust off when you're trying to make a sale, get hired, or impress a room.

I’m talking about the kind of curiosity that lives in your gut. The kind that makes you lean in when someone mentions a job you’ve never heard of, a problem you’ve never thought about, or a passion you don’t yet understand.

The kind that says, “Tell me more.”

I’ve always had it. And I’ve always been a little surprised when others don’t.

Through most of my career, I’ve had a hard time explaining what I do. Whether I’m at a party, a family dinner, or a first-time intro, I’ll start to describe my work—and I can see the moment the glaze hits. A polite nod, a weak follow-up, and then… we’re talking about the weather.

It used to throw me. Still does, sometimes.

Because when I meet someone who’s into something unfamiliar—professionally or personally—I can’t help myself. I want to know how it works. What it means to them. What I’m missing.

There’s that online shorthand, TIL—“Today I Learned.” It’s often used for trivia. For me, it’s a way of life. I love podcasts, books, blogs, videos. But most of all, I love conversations. Especially the kind that change how I see the world.

And that’s the kind of curiosity I want to talk about today. The kind that rewires your perspective. That connects people. That sparks growth—not just for you, but for the people around you. Here's how it showed up in my life.

Soccer Is So Boring

Years ago, I wrote a blog post called Why Is Soccer So Boring? The short version: I used to think it was painfully slow and uneventful.

(I say this as a baseball fan, so… glass houses.)

But something shifted. I started asking friends who loved the game what they saw in it. I listened more closely. Watched with fresh eyes. Learned what to pay attention to.

Turns out, the problem wasn’t soccer. The problem was that I didn’t know how to watch it.

That’s curiosity at work—not the kind you outsource to Google, but the kind that nudges you to slow down and see differently. The kind that says, “Maybe I’m missing something.”

Now I find the rhythm and structure of soccer fascinating. The movement without the ball. The tension between possession and pressure. The elegance of the long game.

It didn’t happen all at once. It took curiosity. And a willingness to admit I might be wrong.

Curiosity That Grows People

I’ve said it before: I’m attracted to “growing” people. Not necessarily the hyper-optimized self-help types. Just people who are open. Who say, “Tell me more.” Who are willing to try something new. Who ask follow-up questions because they actuallywant to know.

You can spot these people pretty easily. They’re the ones who make others feel heard. Who find connections between ideas. Who are comfortable with not knowing and curious enough to do something about it.

That kind of curiosity isn’t loud. It’s not flashy. But it’s powerful—and contagious.

And when people who grow start leading others? That’s when curiosity really scales.

Curiosity as a Leadership Trait

Leaders who model curiosity create teams that ask better questions, spot risk sooner, and build smarter strategies. It’s not about pretending not to know—it’s about signaling that growth is a shared endeavor.

Curiosity isn’t soft. It’s the start of sensemaking, strategic thinking, and strong narrative alignment.

The best founders I’ve worked with—whether they were first-timers or serial entrepreneurs—weren’t just selling. They were learning, listening, adjusting. 

They were curious about their customers, their team, and their blind spots.

Curiosity kept them in motion. Without it, momentum stalls.

Curious People Build Stronger Communities

There’s also a communal benefit to curiosity. When you show genuine interest in someone else’s world, you create space for connection. You make people feel seen. You invite stories, not just sound bites.

That’s how communities are built—not just through shared interests, but through shared curiosity.

When I was at Freshworks, I developed something I called the “cup of coffee.” As the company grew and new key hires joined, I’d reach out—usually on Slack or whatever we were using at the time—and say, “Hey, welcome to Freshworks. Mind if I put some time on your calendar for a cup of coffee? No agenda. Just to chat.” I sent hundreds of those messages. No one ever said no.

Part of the goal was to ease their onboarding—answer questions, connect them with people or teams they might not otherwise encounter. But mostly, I wanted to learn. Why did they join? What were they hoping to accomplish? What else lit them up—hobbies, passions, side quests? The conversations were always rich, and they always gave me a new TIL. More importantly, they helped me build relationships across the org in ways that no meeting invite or job title ever could.

And it all started with a simple, innocuous question: “Do you want to grab a coffee?”

The Case for Staying Curious

I’m not pitching curiosity as some secret weapon or mindset hack. I just think it’s underrated and far too scarce.

We spend a lot of time trying to look smart, have answers, stay on message. But most of the real progress I’ve seen—in business, in leadership, in life—starts with someone asking a better question. Or admitting they don’t know. Or saying, “Help me understand.”

That’s curiosity. Not performative. Not strategic. Just human.

It’s what builds trust. It’s what makes teams stronger. It’s what makes conversations worth having.

And when you make it a habit—when you start to see it as the work, not a distraction from it—curiosity has a way of paying you back.

So this week, don’t try to be the expert. Try to be the person who asks the question no one else thought to ask.

That’s where the good stuff lives.

Berkson's Bits

“The problem isn’t the tool. It’s what you think it replaces.”

Tools can be great—until you expect them to do your thinking for you.

Slack won’t create alignment.
Notion won’t fix chaos.
AI won’t save your strategy.

Start with the wrong assumptions, and the tool just helps you do the wrong work—faster.

What I'm Watching...

As the parent of creators and having many friends who are creators, I've been watching how GenAI plays out in terms of IP and the role of creators going forward in an AI-powered world. My old friend Danny Jose (who was the inspiration for this issue of the newsletter) put together this video presenting the two sides of the creative ecosystem: Team A, who hires them, and Team B, who are the artists.

Check out:: Ghiblification - A post-mortem of the evolution of AI "art".

It's time to let go of "curiosity killed the cat." Genuine curiosity sparks conversations, brings people closer together, and drives innovation and progress. So next time you're at a party, a business event, or even hanging out in line at the grocery store, take a leap and show some curiosity. You will learn something and may even make a new friend or business connection.

Or start with "Can I put some time on your calendar for a cup of coffee? No agenda. Just to chat." And please let me know how that works out for you. Put some time on MY calendar.

Looking forward to continuing the conversation...

Alan