Something I’ve never been that great at is spontaneous conversation. I’m more than capable of public speaking if I’ve prepared something in advance. But if someone asks me something out of the blue, I really struggle to engage in deep conversation. Afterwards I’ll think to myself damn, why didn’t I bring up X or Y?
Half the time I don’t know what to add and I struggle to think of what to say. Sometimes words feel like they’re on the tip of my tongue and I can’t get them out, especially when I’m under pressure. And in group conversations, I find it hard to interject when I do think of a point. By the time a natural break comes along, the conversation has moved on.
I’d love to get better at this. What can I do to improve?
The thing that cracked it open for me was Dale Carnegie "How to Make Friends and Influence People". It is very old fashioned but the core message is evergreen. People aren't interested in you. They are interested in themselves. The more you are interested in them the more interested they will be in you. They will eventually want to know what's on your mind but only because it's a mind that shares interest.
This sounds kind of manipulative because we are only doing it for attention. But the thing is people can smell that from a mile away. You actually have to BE interested and remember the things. You can't just pretend to listen or you will get the opposite effect.
10/10 would recommend
I make new friends constantly just by being genuinely interested in them. I ask a question and while they talk I think of the next question and so on. Eventually, they show genuine interest in return.
It really works when used appropriately.
Newer editions do update the cultural references (which the book has always made heavy use of, and relies on heavily to hammer home it's points). The newer editions might be an easier read for this reason.