John_Maxwell_IV comments on How to always have interesting conversations - Less Wrong
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I do this by running conversations with other people in my head. (Of course, this wasn't my conscious intent, but it probably does make me a better conversationalist.) In general, I'm far more conscious of signaling considerations during my head-conversations, and they frequently feature me being far more bold, frank, and controversial than I would be in normal everyday speech. Also, I typically imagine myself conversing with people I perceive as being less intelligent than me that I'd like to impress.