Going Deeper

Better conversations for only ten minutes of introspection.

Many conversations that are allegedly about interesting subjects fail to actually be interesting. Having worked at an academic-adjacent institution for the last five years, I’ve been a part of a lot of really dumb conversations on topics that I really care about. Like virtue ethics or the value of poetry/art in the age of AI.

These kinds of conversations should go somewhere interesting. When they do not, it is because one or more of the participants fail in very predictable ways. The good news is that these failure modes are easily avoidable, if one is aware of them. So here’s how you can have better conversations for maybe ten minutes of introspection.

Failure 1: Lack of Responsiveness

This is a failure to let other perspectives change your train of thought. A conversation can only be a conversation if there is tension, but there can only be tension if you listen and respond. When you’re in a conversation with someone who is failing in this way, it feels like no matter what you say they will respond with whatever they already had in mind.

This could be because they aren’t paying attention (i.e. they are distracted by their own thoughts), or because they aren’t trying to understand, or because they aren’t letting your proposition really run in their mind (they are only superficially considering it and not seriously considering it). Each of these has slightly different cures. If you find yourself guilty of doing this, the best cure is to slow down. Don’t respond right away, give yourself a second to process, then respond.

Failure 2: Not Getting Confused

An inability to let oneself be confused. This is the more insidious failure. Very often we want to agree with others for social reasons. But agreeing with others doesn’t lead to inquiry, it leads to restating the same position which is the fastest way to stall a conversation.

It’s really important to let yourself be confused and say as much when you are actually confused. This generates tension. It also involves an element of risk. You might look stupid, or perhaps make your conversation partner look stupid. This should be okay, but there is very frequently intellectual insecurities at play which is a damn shame.

“But what if I’m never confused or what if I and my partner have articulated ourselves with perfect clarity and precision?” This is a lie from the devil. Reject it immediately. There is always room to be confused, though sometimes you may need to get creative. If there is no room to be confused, then the terms of the conversation have been set at too general a level to be interesting and it must become more particular, more granular.

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I am guilty of both of these failures on a regular basis. Both of these failure modes stem from a lack of attention, which is the baseline for having a good conversation. It is genuinely hard to approach every conversation with the proper attention that is due, and I deeply respect people who always seem to have it.

I also really really respect people who are able to guide others in avoiding these traps, as that also plays a huge role in helping conversations go deep. And of course not every conversation needs to be deep. Plenty of conversations should be shallow and that is good too.