(Because Apparently We Forgot)
Let’s be clear up front: this is not the last time I’ll be talking about talking. The Art of Conversation is going to be a recurring topic around here. Why? Because it’s layered, nuanced, increasingly rare, and—if we’re being honest—quietly falling apart. Not dramatically. Not all at once. But gradually, like a building you assume is stable until one day the roof gives in and you realize no one’s maintained it in decades.
This is Layer One: speaking and listening. Which sounds obvious, because it is. But lately, even the basics feel like a lost art.
Case in point: a recent evening with a handful of good people in a living room that felt a little too small for the size of our opinions. Conversations everywhere. All overlapping. It was like standing courtside at a pickleball tournament—if everyone had taken a double espresso and decided civility was optional. (Side note: I played tennis competitively. Pickleball isn’t a sport. It’s paddle drama for people who talk during your backswing.)
Anyway, one conversation caught my attention. Two friends—both excited, both loud—talking about a city they had each recently visited. Same place. Different itineraries. Seemed like it could be interesting.
It wasn’t.
What followed was the conversational version of parallel play. Each person listing off their experiences like travel agents with no commission. One would say, “We stayed in the old district, near the temple,” and before the sentence was done, the other would launch into, “Oh yeah, we had the best ramen, the place was on this corner—” and off they’d go. Not dialogue. Not discussion. Just two people performing memory recitals on different stages, hoping for applause.
At one point, they tossed out a random fact about the city—something historical and mildly inaccurate. Ironically, I’d just finished a book that explored that exact topic. I had real insight. I could’ve contributed something useful, maybe even sparked an actual conversation. But I didn’t. I stayed quiet. Nodded when appropriate. Laughed on cue. Offered a positive comment here and there to signal “I’m still alive and vaguely supportive.”
And while this wasn’t a crisis-level situation (no one’s losing sleep over it), it left me thinking about how often we do this—talk at each other, not with each other. We fill the air with words but leave no space for response. Everyone’s performing; no one’s connecting.
I thought of that Rollo May quote—“Real freedom is the ability to pause between stimulus and response, and in that pause, choose.” In leadership, that pause creates clarity. In conversation, it creates connection. Or, it used to.
These days, the pause is endangered.
We Talk Too Much. And We Listen Too Little.
It’s not that we don’t hear each other. We do. But hearing isn’t listening. Listening takes effort. Presence. Restraint. It’s the willingness to let someone else finish their thought before you start forming yours. It’s choosing not to win the exchange, but to understand it.
And this isn’t just me being sensitive because I’ve hit the age where dinner parties feel like better concerts than actual concerts. There’s research for this. Active listening—the kind where you actually absorb, interpret, and respond thoughtfully—is linked to stronger personal relationships, better team performance, and increased empathy. You know, things we could use more of.
But instead of asking questions, we ask “Is it my turn yet?”
Instead of drawing someone out, we draw lines in the air to redirect the spotlight.
The art of conversation has been flattened into a carousel of soundbites. Every interaction is a potential TikTok moment. Every story trimmed to its most shocking or digestible version. And in the race to be interesting, we forget to be interested.
Tell Me Something Real
Good storytelling—real storytelling—requires vulnerability. Not oversharing, not trauma-dumping, just a little openness. You tell me something personal. I listen. I look for what you didn’t say. I notice what lit you up. And when you’re done, I ask about that.
That’s the hinge. That’s where connection starts.
It’s not always 50/50. Sometimes one person talks more. Sometimes one person listens more. That’s fine. Conversation is not a spreadsheet. But it has to move. It has to give. If two people are just waiting to talk again, you’re not talking—you’re scheduling monologues.
The real flex? Asking a question that makes someone pause, then answer with something they didn’t expect to say. That’s what I’m chasing. That’s the kind of dialogue I want more of.
Where I’m At With It
I’ll admit it: I’m still learning this. I get impatient. I sometimes listen just enough to prep my response. I catch myself halfway into a story thinking, “This would be a great segue to tell my version.” I’ve interrupted when I shouldn’t have. I’ve held back when I could’ve gone deeper. But I’m trying.
Not because I want to be some over-polished conversational Jedi. But because I want to be more present. More grounded. More aware that people are letting me in, even if it’s just for a sentence or two. That deserves my attention, not just my approval.
There’s a certain elegance in being able to hold a room—not by dominating it, but by creating space inside it. That’s the kind of presence I’m working on. The kind that doesn’t need the spotlight because the spotlight usually finds it anyway.
And no—I don’t need a deck of icebreaker cards or an app that simulates vulnerability through curated prompts. I just want to be able to sit across from someone, or next to them, and connect. Like really connect. Not out of nostalgia or performance, but because it’s one of the last free things that still holds meaning.
One Layer Down, More to Come
This is just the beginning. The art of conversation has depth, and I plan on exploring every layer—storytelling, silence, group dynamics, knowing when to step in and when to shut up. Because there’s an entire world of meaning hidden in how we talk to one another.
But for now? Start with this: next time you find yourself in a room, listen. Really listen. Find the thread. Ask the question. Don’t rush to reply. Let the pause stretch just a second longer than you’re comfortable with.
You might be surprised what comes out of it.
Let’s talk.
What’s the best conversation you’ve had lately—and what made it stick?
Ever catch yourself just waiting to talk? Ever tried doing the opposite?
Drop a comment. No rush. I’ll wait my turn.
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