Judge a man by his questions rather than by his answers. – Voltaire

I am an introvert by nature, but I come alive for a good conversation. I was reflecting on this after a recent international flight, where I was sitting next to a friendly man who turned out to be a late-career civil engineer. I have a close friend who is a civil engineer, and so as this conversation unfolded I was able to inject pieces of information I’d learned from her – the differences between various civil CAD tools, stormwater management challenges, and so on.

In a conversation that’s going well there are ample opportunities to ask perceptive questions where you can learn interesting pieces of information. That information can then sit in your back pocket, to be carefully deployed the next time you run into a similar conversational vein. This can be absolutely delightful when it works.

I’ve loosely been referring to this as “Collecting Shibboleths” in my inner dialect. “Shibboleth” here is used loosely. It typically denotes language that separates an in-group from an out-group. However, I’m using it more in the sense of language that indicates a certain level of knowledge about a topic, used as a bid for establishing rapport. It’s a “hey, I’ve walked some of these mental paths before, not as deeply as you, but I’m curious to learn more”. And it’s “Collecting Shibboleths” out of recognition that each conversation you have contains an opportunity to learn something interesting or useful. You are building a lifelong repertoire, and you do so by asking engaging questions.

There is a huge difference between “Oh, you do low temperature physics, that’s cool” and getting to “Oh, your lab synthesizes Bose-Einstein Condensates? That’s fascinating – evaporative cooling, right? How long are you able to stabilize it for?”. Usually it doesn’t take much knowledge to bootstrap this. A little knowledge and a lot of curiosity goes a long way.

Using a shibboleth is distinct from pretending to know more about something than I actually do. You aren’t trying to “impress”. Rather, the goal is to add more conversational hooks for the other person to respond to. More interesting paths for the conversation to wander down. More doorknobs that are asking to be turned. You’re looking for a spark of recognition in the other person – the interplay of “Hey! Here’s an opening” and “Yes! I’ll run with it”.

Better questions lead to better answers. Better answers enrich your mental models. And better mental models, in turn, sharpen the questions you ask next time. This leads to a wondrously virtuous cycle in that becoming a better conversationalist is self-reinforcing.