I've been thinking about this a lot lately.
Not because I read it in a book or heard it at a conference. But because my kids have been teaching me the same lesson on repeat.
It starts innocently. My daughter says something about her day. A sentence, maybe two. And instead of nodding and moving on (which, if I'm honest, is the path of least resistance after a long day), I ask: "Tell me more."
And then something happens.
What started as a one-liner becomes a storyline. A character appears. There's a plot twist. There's conflict, resolution, and usually an ending I didn't see coming. She's four and a half. And yet, given the space and the invitation, she will spin a narrative that holds the room.
Over the past year or so, I've found the same thing happening in a very different context. I've been lucky enough to spend a lot of time with some genuinely fascinating builders and entrepreneurs—people at the earliest stages of trying to solve real problems in the world. And somewhere along the way, I realized I'd developed a natural pull toward the same instinct: ask more, talk less. Not to be polite, but because their perception of the problem they're solving—and the insights they've accumulated along the way—is almost always more interesting than whatever I was about to say next.
The lesson isn't about kids. And it isn't really about founders either. It's about what happens when you make the conversation genuinely about the other person—when you check your own agenda at the door and just follow the thread.
The Art of the Next Question
Most conversations are really just two people waiting for their turn to talk.
We listen enough to respond. We absorb the headline and start formulating our reply. We're present in body but already somewhere else in mind—preparing our anecdote, our rebuttal, our advice, our pivot to what we want to say next.
"Tell me more" breaks that pattern entirely.
It's not a technique. It's a genuine act of curiosity. It signals: I'm not done with your story. I want to go deeper. And for the person on the receiving end, that signal lands differently than almost anything else you can offer in a conversation.
The follow-up question—"what happened next?" or "how did that make you feel?" or simply "tell me more"—is an invitation. And most people, when genuinely invited, have far more to say than they expected to share.
Everyone Has a Plot Twist
Here's what I've noticed: most people who've been on this planet for any reasonable amount of time have a genuinely interesting story. Usually more than one.
But stories don't surface automatically. They surface in response to curiosity. They come out when someone asks the next question instead of filling the silence with their own voice.
The quiet person at the dinner party who seems like they have nothing to say? Ask them one honest follow-up question and give them space. You'll often find decades of experience, a career pivot that changed everything, a loss that reframed their worldview, a passion project that doesn't match their job title at all.
The founder who gives you the two-line elevator pitch? Ask "tell me more about why you specifically are building this"—and suddenly you're in a different conversation. One that has weight and origin and real skin in the game.
People are walking plot twists. They just need an invitation to unfold.
What This Has to Do with Building
I bring this up in the context of founders and builders because "tell me more" might be the most underrated tool in your entire GTM arsenal.
We spend enormous energy crafting what we say—the pitch, the deck, the positioning, the messaging hierarchy. We rehearse our answers. We prepare for objections.
But the founders and builders who tend to find product-market fit faster? In my experience, they're the ones who've asked "tell me more" often enough—and genuinely listened to the answers—that they've built a map of the market's real pain from the inside out.
Not what the survey said. Not what the focus group agreed on. What the customer actually said when someone gave them the space to go deeper than the headline.
A customer says "we've tried similar things before." Most people nod and move on. The right response is: "Tell me more about that—what did you try, and what happened?"
A prospect says "the timing isn't right." Most people accept it and schedule a follow-up. The right response is: "Tell me more—what would need to be different for the timing to work?"
These aren't tricks. They're invitations. And the answers almost always contain the real information—the thing that doesn't show up in your CRM notes, the thing your competitor hasn't heard yet, the thing that actually tells you what it would take to earn trust.
The Practice
The good news is that "tell me more" is a muscle. You can build it anywhere—at the dinner table, in a taxi, in the five minutes before a meeting starts.
The practice is simple but not easy:
Lead with curiosity, not agenda. Walk into the conversation with one goal: to understand this person better than you did before you sat down.
Resist the pivot to yourself. When their story triggers one of yours, note it and let it go. Stay in their narrative.
Ask one more question than feels natural. Most people stop one question too early. The second or third "tell me more" is where the interesting part usually lives.
Get comfortable in the silence. The pause after a question isn't awkward—it's the person deciding how honest to be. Give it room.
Follow the energy, not the script. When their voice changes, when they lean in, when they laugh or pause unexpectedly—follow that thread. That's where the story lives.
The Compounding Return
Here's the thing nobody tells you about "tell me more": it compounds.
The more genuinely curious you are with people, the more they open up over time. Relationships deepen faster. Trust builds in a fraction of the usual time. People remember how you made them feel—which is heard, seen, and interesting—long after the specifics of the conversation have faded.
For founders, this is how you build a network that actually opens doors. Not by broadcasting your brilliance, but by becoming the person who makes everyone else feel like theirs is the conversation worth having.
My daughter doesn't know she's teaching me this. She just knows that when I ask "tell me more," she gets to keep going—and that makes the story better.
It works exactly the same way with adults. With customers. With investors. With the person across the table who you've mentally written off as having nothing interesting to say.
The next conversation you're in—try it. Ask one more question than you normally would. Follow the thread. See where it goes.
You might be surprised by the plot twist.