In the last post, I said that serious conversation allows us to deepen and broaden our understanding of the wisdom contained int he greatest books and artworks. What is serious conversation? And how does it enhance our reading?

Let’s begin with what it is not, since many people seem to be put off by the very notion of discussions that go deeply into any subject.

• Serious conversation is not tedious, dry, self-important, humorless talk among effete intellectuals (or pseudo-intellectuals) and poseurs.
• It is not a phony discussion or a disguised lecture led by an expert who allows a certain mount of input before delivering an authoritative judgment.
• It is not a bull session, a round-robin of participants venting their “feelings.”
• It is not a series of monologues, like the prepared speeches of experts at a panel session.

In contrast to all this, serious conversation resembles talk at a cocktail party. Participants ask questions, listen to one another, consider what is said, reply with their own confirming observations or challenge with some disconfirming observations, ask more questions, and continue on in this way.

On the other hand, serious conversation differs from cocktail conversation in that the topic under discussion is a great book or artwork. The talk centers on that book or artwork and keeps returning to it. The aim of the discussion is two-fold. First, we want to discover what the author or artist is trying to communicate. And second, we want, if possible, to extract valuable wisdom from the book or artwork—although what counts as valuable may differ for different participants.

Those who have never engaged in such discussions may find it hard to imagine that much enlightenment could arise without the expert direction of specialists.

But those who have experience with serious conversation know that highly unexpected insights and realizations can emerge from such discussions, so long as the participants are diligent in the pursuit of understanding, helpful to the group, and generous toward the work being considered and toward one another.

What does a serious conversation look like? It begins with a concise and pointed question about the work under consideration. Some care must be taken with this opening question. It should not be easily answerable, like a question of fact. “When was this book written?” is not a good conversation-starter. The conversation is over as soon as the fact is ascertained. Moreover, the opening question should not be peripheral, like a question about the creator’s biography or about social or historical context or about scholarship surrounding the creator or the work. Questions like these immediately wrest the focus away from the work at hand.

Good opening questions usually try to get at something perplexing in the work being discussed. Questions of interpretation often work very well. “What is meant by the term X?” or “Does this passage contradict that passage or is their some way to understand them together?” or “Why does this image keep recurring?” or “What is the effect of this semicircular patch of green in the upper right corner?” are the sorts of questions that move participants into the work rather than away from it.

After the opening question, the participants make initial attempts to respond, which lead to other questions and further responses, which in turn lead to other questions and further responses, and so on until the time is up.

Along the way, there can be detours, dead ends, silences, and frustrations. All of these are overcome by returning to a question about the work.

But there can also be discoveries, illuminations, even life-changing epiphanies. In one sense, serious conversation is just like life itself—a condensed version of the ups and downs experienced by an attentive and inquisitive seeker on the journey through this existence.

What is more, though, is that serious conversation can bring new meaning to life and intensify the living of it.

In her wonderful book Becoming Wise: An Inquiry into the Mystery and Art of Living, Krista Tippett recognizes the importance of good questions and serious conversation in leading a meaningful life. She explains why this sort of engagement is sorely needed in today’s fractious society:

The art of starting new kinds of conversations, of creating new departure points and new outcomes in our common grappling, is not rocket science. But it does require that we nuance or retire some habits so ingrained that they feel like the only way it can be done. We’ve all been trained to be advocates for what we care about. This has its place and its value in civil society, but it can get in the way of the axial move of deciding to care about each other.

In order to have better conversations, we have to unlearn bad habits. We have to learn to listen generously:

Generous listening is powered by curiosity, a virtue we can invite and nurture in ourselves to render it instinctive. It involves a kind of vulnerability—a willingness to be surprised, to let go of assumptions and take in ambiguity. The listener wants to understand the humanity behind the words of the other, and patiently summons one’s own best self and one’s own best words and questions.

We cannot summon our best thoughts in conversation without paying close attention to what other participants are saying and trying to interpret their thoughts in the best possible light. This requires more of us than just waiting for the chance to say what’s on our mind. It requires more of us than just wanting to shine or be admired or be right.

We want others to acknowledge that our answers are right. We call the debate or get on the same page or take a vote and move on. The alternative involves a different orientation to the point of conversing in the first place: to invite searching—not on who is right and who is wrong and the arguments on every side; not on whether we can agree; but on what is at stake in human terms for us all. There is value in learning to speak together honestly and relate to each other with dignity, without rushing to common ground that would leave all the hard questions hanging.

This is serious conversation. And when its attention is turned on a great book or artwork, we get the benefit of learning to acknowledge others in their full humanity together with the treasure of the wisdom contained in the work before us.

Serious conversation seriously conducted fortifies both our humanity and our understanding.

It is a shame that there are not more opportunities to participate in it. And it’s even more of a shame that there are not more people who have the inclination to participate in it.