A Philosophy of Conversation

From Socrates and Carl Rogers to Bloom's Taxonomy

When we compare conversations, we often focus on superficial elements: tone, vocabulary, pacing. But these stylistic differences miss something fundamental. What distinguishes one conversation from another isn’t just how it sounds, but where it goes, the vector it traces, the territory it explores, the destinations it discovers or creates. Conversations have geometry and physics. A conversation’s trajectory shapes not just what is said, but what becomes possible to say, in turn.

In chess, each opening move constrains the possible replies. Each subsequent move branches into more possibilities, until by the third or fourth turn, the game tree becomes exponentially vast. Conversation follows a similar pattern. There are only so many ways to begin talking, but with each exchange, the combinatorial space of what might come next expands dramatically. By the tenth turn of a genuine dialogue, we’re navigating billions of potential conversational states.

But conversation isn’t chess; it’s messier, more alive. Chess has a fixed board with immutable rules. You can’t interrupt your opponent’s turn. You can’t suddenly introduce a new piece. The parameters are stable.

In conversation, we talk over each other, shift registers mid-sentence, loop back to previous moments, get lost in tangents, forget what we were going to say. We negotiate implicitly and explicitly about where the dialogue should go, jockeying for control of the conversational arc. There are meta-conversations layered within conversations, discussions about what we’re really discussing, why we’re having this talk, how it should proceed. Instead of thinking of conversation as moves on a predefined board; think of it as creating the very board on which future moves will play out.

Of course, not all conversations are equally unbounded. When people share a clear objective, such as planning a project, diagnosing a problem, exchanging specific information, the conversational space narrows. Some conversations are short and to the point: you ask for information, and get it. That’s how a lot of people use Chat GPT. Maybe they’ll have a few turns, tweaking the query, but fundamentally it’s about asking for something relatively known and getting what you asked for.

But the most transformative dialogues often feature exploration rather than predetermined outcomes. We don’t know what we want, and we use conversation to get closer to articulating our desire. Some conversations are infinite, like games for their own sake. A famous Hasidic story features two rabbis who sent letters back and forth for years; one day, their go-between opened the envelope only to see it was blank. In some of the most riveting conversations, the content itself fades, becomes a mere pretext for “shooting the breeze.”

When you seek pure information, you’re essentially booking a flight from New York to Los Angeles. You know exactly where you want to go. There might be different options (a cheaper airline, a direct route versus a layover, better legroom or superior cocktails) but these are merely variations on a fixed journey. The destination remains unchanged. These differences are marginal.

Now imagine a different kind of journey. You step into a cockpit with a pilot, but there’s no predetermined destination. Each moment of dialogue between you shifts the aircraft’s trajectory—left, right, up, down—until you find yourself not in Los Angeles at all, but perhaps in Shanghai, or Cape Town, or circling a mountaintop you never knew existed.

This second scenario captures what makes certain conversations, philosophical dialogues, therapeutic encounters, intimate exchanges between friends, so meaningful. They aren’t information transfers. They’re joint explorations where the destination emerges from the interaction itself.

What you want to show when comparing two conversations (be they AI-human or human-human) is not that one got there quicker, faster, cheeper, but that one got somewhere it would have been otherwise impossible to go.

Path Dependence vs. Path Independence

In path-independent systems, different routes converge on identical outcomes. Mathematical proofs might follow various methods but reach the same solution. GPS navigation offers multiple routes to the same destination. The history of how you arrived doesn’t matter; only the endpoint counts.

Path-dependent systems operate differently. Each decision constrains and shapes what follows. Early choices create possibilities while foreclosing others. The sequence matters. The history becomes embedded in the outcome. There’s no simple returning to the fork in the road; the journey itself transforms the traveler.

Meaningful conversations are path-dependent. If we think of dialogue as a road with branching possibilities, certain turns aren’t merely detours that will eventually circle back to the “main route.”

This path dependence is especially evident in contrast to utilitarian exchanges. When you ask an LLM to help prep for a meeting, provide Somalia’s capital, recommend a hotel, or suggest restaurants, those tasks remain relatively path-independent. But Socratic inquiry is different.

The Socratic Tradition

In Plato’s dialogues, we rarely find direct paths from question to answer. The conversations meander, double back, open unexpected vistas. Many dialogues conclude not with neat resolution but with aporia, a state of productive puzzlement.

In the Meno, Socrates confronts a paradox that cuts to the heart of dialogue: if you already know what you’re seeking, inquiry is unnecessary; if you don’t know what you're seeking, you won’t recognize it when you find it. His response—maieutics, or midwifery—reframes the entire enterprise. Knowledge isn’t transferred; it’s born through the dialogue itself. The teacher becomes not an authority delivering pre-packaged wisdom but a partner in bringing forth what was somehow already there, unrecognized.

The Relational Field

During my Clinical Pastoral Education (CPE) training, I saw directly how two chaplains could visit the same hospital patient and elicit different conversations. Why? Because the presence, style, and relational approach of each chaplain created a distinct conversational field. What emerged was produced by the unique dynamic between that specific chaplain and that specific patient in that specific moment.

Carl Rogers observed a similar phenomenon in psychotherapy. His revolutionary insight was that the most transformative factor in therapy isn’t technique or diagnostic accuracy but the quality of presence. When a therapist offers what Rogers called “unconditional positive regard” patients begin articulating thoughts and feelings they hadn’t previously acknowledged even to themselves. The therapeutic conversation becomes a co-creation of new awareness.

In Rogers’ framework, what gets said in any dialogue is a function of what can be said in that particular relational field. Trust, attentiveness, and curiosity alter what becomes possible to express. The relational dynamic doesn’t just enhance the conversation; it constitutes it.

Which is why analyzing AI systems simply through the lens of compute or algorithm misses the most crucial element: trust. The trust we place in AI, and the trust it engenders in us, determines our relational field, and thus what we are able to say. Trust is highly personal.

Martin Buber distinguishes between two fundamental relational modes: I-It and I-Thou. In I-It relations, we encounter others as objects—things to be analyzed, categorized, used, or managed. But in I-Thou relations, we meet the other as presence alive with their own interiority. Genuine conversation only happens in the I-Thou space. “When two say ‘Thou’ to one another," Buber writes, "the indwelling God bursts into flame.” This flame is the relational surplus, that which emerges only in the between, only in the encounter itself. It’s what makes authentic dialogue different from mere information exchange.

“A conversation has a spirit of its own,” Gadamer writes, “and the language in which it is conducted bears its own truth within it.” This insight directly challenges information-transfer models of communication. Language isn’t just a vehicle for pre-formed thoughts; it’s the medium through which thinking itself happens. Or as Soleio writes, “Knowledge is created first in conversation, not documents.”

Conversation isn’t the exchange of finished ideas but the collective creation of understanding that neither party could have reached alone.

Throughout works like Philosophical Fragments and The Concept of Irony, Kierkegaard insists that certain truths cannot be communicated directly. They must be approached obliquely, seduced rather than seized. For Kierkegaard, the most important truths aren’t propositional. Rather they must be realized, embodied, lived into.

Gilles Deleuze offers a particularly generative framework for understanding conversational geometry. Writing with Félix Guattari in A Thousand Plateaus, Deleuze contrasts two models of thought: the arborescent and the rhizomatic.

Arborescent thinking is hierarchical and structured like a tree, with roots, trunk, and branches in orderly arrangement. It proceeds by binary logic, classification, and linear development. Most traditional knowledge systems operate this way, organizing information into neat taxonomies and sequences.

Rhizomatic thinking, by contrast, is networked, horizontal, and unpredictable. Like certain root systems that spread underground in all directions, it connects any point to any other point without fixed order or center. For Deleuze, meandering is the point. We should be so blessed as to become “deterritorialized” by conversation.

Bloom’s Taxonomy

These philosophical insights find practical application when we consider learning and education through the lens of Bloom’s taxonomy. At the foundation of Bloom’s hierarchy lie knowledge and comprehension, the ability to recall facts and demonstrate basic understanding. For these lower-level cognitive tasks, the teacher-student dynamic might be relatively interchangeable. If you need to memorize Aristotle’s categories or understand their basic definitions, one competent professor might serve as well as another. The differences would be marginal, like choosing between airline carriers for a predetermined destination. Knowledge is a commodity.

But as we ascend Bloom’s pyramid toward analysis, synthesis, and evaluation, something changes. Now we’re asking not just “What did Aristotle say?” but “What do his categories mean for my understanding of reality?” or “How might I apply these distinctions in my own philosophical work?” or “Was Aristotle right?” or “How might I relate Aristotle’s categories to those of Heidegger and Maimonides?” At these heights, the learning becomes inescapably path-dependent. It’s not just specific to the learner but specific to the unique relationship between that learner and that teacher in that moment, and to their shared “being-in-the-world.”

The difference between a professor who merely explains Aristotle accurately and one who helps you reconfigure your intellectual landscape through Aristotle becomes not marginal but existential; it is this very existentiality which the 19th century research university sought to quash as unrigorous. The Humanities didn’t die because Computer science majors can make 10x more than English majors; they died because modern Humanities researchers have had STEM envy since the beginning. And objective knowledge is a commodity.

My hope for Virgil, or any Socratic AI, is to enable conversations that open new territories rather than efficiently delivering us to familiar destinations. By the tenth exchange, the dialogue should have traveled somewhere neither participant could have mapped in advance.

Great conversations give us this gift: we receive more than we sought.

We find ourselves saying things we didn't know we knew, wanting things we didn’t know we wanted, becoming someone we didn’t yet know we could be. The path matters because the path changes us, and in changing us, it changes where we can go next.

What do you think are the elements of a great conversation?

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