Talking Well

31st of May, 2025

Talking to other people is worth doing well. Even when there is no ultimate goal, especially when conversation itself is the goal, it pays off to put in effort. Talking is sometimes compared to dance, or to jūjitsu; in both the need for deliberate practice is more obvious. Here we address the painful inability to have our words cut through to our partner, in order to someday be able to tell a Musashi-style story of having, verbally, slain.

The most critical part of a conversation is already over when we open our mouth. We first need to make sure that we are receptive to what the other person is saying, which sounds a lot easier than it is. A psychoanalyst friend described it spatially; in the average conversation, the two participants occupy an equal amount of physical volume with their speech. Think of Voronoi cells. To deviate from this default, the psychoanalyst needs to retract their volume and let the patient inflate.

So we want to give our conversation partner space to express themselves. To be successful, we will have to notice and ignore our urges to make them behave a certain way. To address the most common pattern: We have to quit trying to impress them, even though we are of course desperately craving validation the whole time. When we can assure the other person that we do not want them to respond in any particular way, it can have a profound effect. Communicating this stance quickly is the most important skill in conversation.

A useful tool can be our voice and posture. Attending to our own voice will usually reveal large differences depending on the conversation partner. We want to shift more towards the voice we adopt when we are at ease, and naturally curious about our conversation partner. The same goes for body language. We will want face our partner at all times. Not only introverts could benefit from looking much more at their interlocutor. In a beginners' social dance class for instance, where the fear of judgment is particularly strong, most everybody instinctively stares at the floor.

But acting like an all-ears-counselor, while already a tremendous improvement on the default style (try it!), is still a poor strategy of making conversation. Why is that?

Not properly listening has another guise. In polite chat, it often happens that two parties claim the exact opposite of each other, while at the same time acquiescing to the other's view so aggressively as if they have a personal vendetta against the law of excluded middle. The pattern often plays out especially awkwardly when someone retracts their clearly false statement after their partner has already instinctively answered "yes, yes". If the constant affirmation is on purpose, it is a Death by Carnegie. To avoid it, the listener has to scrutinize and put everyone's ego aside, not just their own.

The follower in tango leans forward and applies pressure to their partner in order to read the next step. We, too, give some verbal resistance, perhaps pointing out inconsistencies. Thinking maieutically (from gr: μαιευτική) helps: We draw out the most consistent version of their ideas through setting their statements in relation to each other. At the risk of being annoying, the idea is to be a little bit dangerous to our conversation partner, in that they should sense the potential to be changed in the course of the conversation.

Speaking of, now it is finally time for us to give some input to the dialogue. Starting slow, we pose a question first. But what should we ask?

An often cited piece of prior art on good topics for "deep" conversation is "The experimental generation of interpersonal closeness: A procedure and some preliminary findings" by Aron et al. (1997), which has pairs of participants go through 36 increasingly "intense" conversation prompts. Inquirers like ourselves keep coming back to the better ones, like "Do you have a secret hunch about how you will die?".

However, some other questions on the list feel more forced, like Dr. Freud's favorite "What is your relationship with your mother?". Having tried some of these, we ultimately realize that there is no substitute for an unending curiosity about how the other person sees the world, and that an array like this should supply only the entry point. Still, the paradigm is useful because it teaches not to bust out our own hobby horses whenever given the chance.

A handy source of questions is a domain where our partner knows more than we do. Good questions cannot be answered in absence of the conversation partner, and can be answered both quickly and slowly. Because we are not interviewing anybody, yes-no-questions are actually just fine. Loaded questions are even better. The most important component of steering an interesting conversation is plainly to surprise your partner.

This is why playing the active part is more difficult. You have to meet the vital prerequisite of actually being interesting, not just curious. One strategy to become interesting is being in the habit of thinking or feeling things once in a while, or at least read up on what people have thought or felt so far. If the current conversation partner feels like they would enjoy talking to a past one, it can be fun to bring up ideas from the previous chat.

A more vicious problem is gaining the courage to be able to talk about any subject we want to, if the situation calls for it. It is very difficult to talk about how we have wronged people, for example, because we are afraid that the listener will start hating us. When attempted, though, it has unexpected benefits. We rarely speak honestly of what we envy, what we dread, what we are proud of, and what we worship. These concepts are often expressed vicariously in art, which can help to bring them up without building up expectations. It is impossible to overshare to a master of conversation.

When talking to people works out really nicely, it can produce an outsized benefit. This means that there is no need to make every conversation turn out great, just a few outliers are enough to pay off the lot. As we incur these outliers, we will have great friendships to show for it, and be glad that we cared about talking well.