On Great Conversation

Achieving Conversational "Flow"

There's a curious relationship between time and conversation quality. Most great conversations are long ones; they unfold over hours, meandering through topics with the leisurely pace of a river finding its course. Yet duration alone doesn't create greatness. We've all endured endless conversations that felt like watching paint dry, where minutes stretched like hours and we found ourselves calculating escape routes. The mystery isn't that great conversations take time, but why some long conversations achieve transcendence while others become endurance tests. Think of it this way: you can spend three hours trapped in someone's monologue about their home renovation project, checking your phone surreptitiously and wondering if this qualifies as a form of torture. Or you can spend three hours with a friend exploring the nature of friendship itself, completely losing track of time until you realize the restaurant staff is stacking chairs around you.

The answer lies in understanding conversation as something closer to tennis than to lecturing. In tennis, a great rally isn't about one player dominating with an unreturnable serve—it's about both players keeping the ball in play, each shot building on the last, creating something neither could achieve alone. The rally becomes beautiful precisely because it requires mutual skill and attention. A 6-0, 6-0 victory might demonstrate superiority, but it doesn't create the mesmerizing back-and-forth that makes tennis worth watching. The same dynamic governs great conversation. It's not about intellectual aces or conversational winners. It's about sustaining a rally where each participant's contribution makes the next move possible and more interesting.

Most conversations, however, don't even achieve the level of failed tennis rallies. Instead, we encounter what might be called parallel monologues—two people taking turns talking to themselves while appearing to engage in dialogue. Sarah shares a story about her challenging day at work, describing the complex dynamics with her boss and her uncertainty about how to handle the situation. Instead of asking follow-up questions or exploring Sarah's dilemma, her friend Mike immediately launches into his own work story: "That reminds me of what happened to me last week..." Sarah's ball has been ignored entirely while Mike serves from his own court. This kind of conversational narcissism is so common we barely notice it anymore. But it differs crucially from the healthy self-reference that actually fuels good dialogue. When someone shares a personal experience that genuinely connects to and advances what you've said, they're not being narcissistic; they're offering their experience as material for the shared construction of meaning. The difference lies in whether the personal reference builds on what came before or simply replaces it.

There's an even more subtle failure mode than obvious narcissism: what the philosopher Martin Heidegger called "Gerede"—idle chatter that fills time without creating meaning. You know this kind of conversation. Two people can talk for hours about nothing in particular, cycling through familiar topics with the practiced ease of actors performing a well-rehearsed play. The weather, work complaints, mutual acquaintances, television shows—all perfectly pleasant, but ultimately forgettable. The conversation has duration but no development, length without depth.

The rabbinical tradition had a term for speech that diminishes rather than nourishes: "lashon hara." While often translated as gossip, the concept encompasses any speech that's ultimately harmful. Idle chatter can be understood as a form of lashon hara because it keeps us trapped in patterns that don't challenge or nourish us. We come away from such conversations feeling vaguely depleted rather than energized.

The antidote to idle chatter lies in what psychologist Mihaly Csikszentmihalyi described as “flow,” that state of optimal experience where challenge and skill are perfectly matched. Great conversations create a kind of interpersonal flow state. They require enough intellectual or emotional challenge to keep participants engaged, but not so much as to overwhelm. Like a tennis rally between well-matched players, each exchange should push the other person slightly beyond their comfort zone while remaining within their capacity to respond meaningfully.

This is why conversations need onboarding time. Just as tennis players need a few practice shots to find their rhythm, conversations usually require several exchanges before participants discover their shared wavelength. The opening moves are often tentative, testing the waters. Can this person handle abstract ideas, or do they prefer concrete examples? Are they comfortable with disagreement, or do they need consensus to feel safe? Do they think by talking, or do they prefer to formulate thoughts before speaking? Great conversationalists are masters of this initial calibration. They quickly sense what kind of rally their partner is capable of sustaining. They might start with safer topics and gradually introduce more complex or personal themes as trust builds. They adjust their conversational style in real time, like a tennis player who notices their opponent is stronger on the backhand and begins feeding them more forehand shots to create better rallies.

Once properly calibrated, great conversations develop their own momentum. Ideas build upon each other in ways that surprise both participants. You find yourself saying things you didn't know you thought, making connections you hadn't seen before. Neither person fully controls the direction; instead, you're co-creating something neither could have planned. This collaborative emergence is what distinguishes great conversation from even the most skilled monologue. Watch this dynamic in action and you'll notice something interesting: the best conversationalists often seem to disappear into the conversation itself. They're not performing their intelligence or trying to impress. Instead, they're genuinely curious about where the dialogue might lead. They ask questions not to show how smart they are, but because they want to know the answers. They share personal experiences not to center attention on themselves, but because those experiences illuminate the topic at hand.

Mark Zuckerberg recently claimed that the average person wants about fifteen friends. Whether you agree it or not, Zuckerberg’s point raises challenging questions: How many truly great conversations do you have in a week? How many people in your life can consistently engage you in the kind of dialogue that creates flow, where you lose track of time because you're fully absorbed in the collaborative exploration of ideas?

Most of us, if we're honest, would have to admit the number is surprisingly small. We might have dozens of people we can chat with pleasantly, scores of acquaintances who can fill time agreeably. But how many can reliably engage us in conversation that feels genuinely nourishing? How many leave us feeling more alive and interesting than when we started talking? This scarcity isn't necessarily a problem. You wouldn't expect to encounter great music or great literature constantly; why should great conversation be different? But the rarity does suggest we might benefit from being more intentional about both cultivating our capacity for such conversations and recognizing them when they occur.