What makes a conversation "good"?
thoughts on the qualities of enjoyable (and productive) dialogue
Happy Sunday -
I find myself lately wrestling with the question:
what makes a conversation good?
I wrestle with this question within two primary contexts:
professional: conversations are a substantive ingredient toward building teamwork, output, and business outcomes
personal: conversations are a meaningful way to connect and spend time with quality people in our lives
In both the professional and personal contexts most of us seem to instinctually recognize a good conversation when we’re actively participating in one:
Professionally:
“we’re making progress”
“you’re making great points”
“this is great teamwork”
“this is a productive meeting”
Personally:
“we covered a lot of ground”
“we got deep”
“it was great talking with you”
“I’m really enjoying this conversation”
“what a lovely time”
We effortlessly articulate verbal tips of the cap to great conversations in everyday moments of our daily lives. We easily recognize a good conversation when we’re in one. Recognition of the presence of quality is easy.
But definition/description of this quality? Harder, at least for me. What substance and structure make a conversation good/engaging/enjoyable? Inversely, what makes a conversation bad/boring/unenjoyable?
When I first posed this question to myself I swirled the drain without a succinct answer. When words fail, sometimes drawing is our saving grace. So I took to sketching out some ideas:
Start (A) to Finish (B):
I remember a quote in the context of a sales training I heard during my first job out of school that I think could seemingly apply to most conversations in life: “buyers will buy from you if you can lead them to a place that they cannot get to by themselves”. Whether it’s a buyer in a professional sense (customer), a romantic sense (a date/partner), a personal sense (friend), when we engage in a conversation, we’re investing our valuable time and finite attention, both of which carry opportunity costs. To justify the commitment of time and attention in the face of opportunity costs, we expect (implicitly or explicitly) a return on our time and attention. For a customer, this return is perhaps information or knowledge that better helps them solve their business problems. For a romantic interest, perhaps it’s a boost of self-esteem and/or a stronger feeling of chemistry, connection, or desire. For a friend, perhaps it’s wisdom, clarity, knowledge, connection, or the intrinsic dopamine benefits of time well spent. ROI implies if we invest something now, we get something in return later (or throughout). So within the logic of ROI there is an expectation of sequencing, an expectation of moving from a current state (start) to future state (finish).
Thinking back on mediocre or bad conversations (boring, unenjoyable, convoluted), many lack a coherent direction or understanding of what the benefit of the conversation is. This seems especially true in a professional setting where efficiency, clarity, and mutual value creation are of paramount importance to participating parties. If we consider professional conversations where are unclear of the end goal and/or the reason for meeting, we find ourselves usually asking some flavor of “where are we going with this?”
Direction brings us an understanding of how the conversation will progress, understanding provides clarity to quantify ROI on time, clarity yields stability, stability drives presence and attention, and presence and attention drive a heightened sense of enjoyment. So direction thus seems to drive enjoyment.
Tangents (C) and Counterfactuals (D):
But conversations that move linearly from start (A) to finish (B) without digression and variance can often feel rushed, formulaic, overly regimented, and bland. I think here is where our penchant for adventure and variety comes in. Along the progression of a narrative arc from A to B, conversationalists can together go “off the beaten path” and explore tangents that are connected (via varying degrees of strength, sometimes none at all) to the primary narrative arc.
Conversational tangents are features that psychologists might call affordances: “features of the environment that allow you to do something”:
“Physical affordances are things like stairs and handles and benches. Conversational affordances are things like digressions and confessions and bold claims that beg for a rejoinder. Talking to another person is like rock climbing, except you are my rock wall and I am yours. If you reach up, I can grab onto your hand, and we can both hoist ourselves skyward. Maybe that’s why a really good conversation feels a little bit like floating.”
So to carry forward the rock climbing analogy, if the narrative arc beginning to end (A to B) is the vertical progression of a climber up a wall, perhaps tangents are the rocks on the wall we grab onto.
I think often here about the excitement tangents can often create between or among participants. “Forgive me for going on a tangent” often follows a passionate monologue. “I have no idea how we got on that topic” can often be a source of after-the-fact amusement or laughter between parties. “Ok, rant over,” says a heated friend. There seems to be charged energy created via tangents. Perhaps this is because of the variance, adventure, and unexpectedness of the tangential topics. Does a contrast between the primary narrative arc and its digressing tangents create a pleasant sense of variance between primary and alternate, yin and yang?
Tangents also seem to be stronger when both (or all) conversation participants can walk out on the tangent limb together (building a mutual & shared sense of adventure) versus only being participated in by one/some of the participants. Consider the many times when a participant in a conversation will be on a solo tangent that we and/or the rest of the group have no interest in being on it with them. It can be painful to be dragged through someone else’s monologue when we feel wholly disconnected from its contents, spirit, or purpose. Like adventure, conversational tangents seem good alone, and great together.
If conversational tangents are veins of emotion and adventure away from the primary narrative arc, counterfactuals are a grounding and opposing force that guide us back to the primary arc of the dialogue. counterfactuals are the dingy boat motoring us back to the mother ship when we’ve wandered too far away. Especially in conversations where knowledge, learnings and/or wisdom are components of the implied ROI, counterfactuals are the opposing view, the logical objectivity, the counterargument, the strawman argument. If I and a friend are together co-creating a passionate bit about the cultural merits of life in New York City, a grounding counterfactual is one of us bringing us back to earth by presenting the opportunity costs of life in New York—suburbs, crickets, driving, living closer to the ocean, fewer heaps of trash, etc. While 1-way tangents untethered to counterfactuals may make us feel good emotionally, and potentially more connected to the person we’re on the tangent with, counterfactuals seemingly produce balanced knowledge, more well-rounded points of view, and likely a sense of comfort with this more nuanced thinking (versus the incompleteness of a tilted point of view).
Velocity (E) and Acceleration (F):
Just as it seems that conversational tangents and their counterfactual ballasts create a pleasant heterogeneity to a conversation, it also seems that the conversational pace (velocity) and changes in velocity (acceleration) are directionally correlated with the enjoyment of a conversation. If the human brain is evolutionarily wired to process stories as a means of survival and knowledge accrual (stories are the building blocks of societal torch passing), and stories are ripe with variance, uncertainty, and change, it would be sensible to think we are evolutionarily programmed to respond well to conversations that contain variance and uncertainty. Our never-ending demand for movies, TV shows, books, and character development throughout our culture is a strong proof point supporting this.
In 2022 the National Academy of Science, via researchers at Princeton, published an interesting paper citing evidence that faster response times in a conversation create a heightened social connection between participants. Heightened social connection = more enjoyment of a conversation, per the charts below:
If we trust the results above, a higher overall conversational velocity directionally translates to more enjoyable conversations.
But if the velocity is high the entire time, can the monotony of the fast-paced dialogue bore us, overwhelm us, etc? On this one, I am admittedly drawing more from personal anecdotes than I am on science to suppose that variance to the conversational velocity (acceleration) creates heightened sense of enjoyment. Thinking back to conversations when the other participant(s) engaged with an unchanged speaking velocity, eventually the monotony tires us out a bit. Whereas in a dialogue of changing pace, there are narrative sub-arcs within the the narrative arc, variance that provides a sense of pleasure when the dialogue speeds up to slow down to speed-back-up-at-a-breakneck-pace-once-again-when-things-get-thrilling-and-the-caffeine-hits-and-all-parties-are-firing-on-all-cylinders only to then give way to a long and slow and lei-sure-ly saun-ter.
I am sure these will evolve and change as more conversations happen in life. I wanted to get these down on paper as a v1 to build on over time. If you have any thoughts big or small on what makes good conversation for you, including any notable examples, I’d love to hear them.
Have a good week (full of good conversations!).
Here are citations to the links I enjoyed on this topic and included in this writing:
Adam Mastroianni (Experimental History): Good conversations have lots of doorknobs
Chris Williamson & Cameron Hanes: What makes an elite communicator? (watch 1:21:15)
National Academy of Science: fast response times signal social connection in conversation