Comment by Lou Nowell (lou-nowell) on You're never wrong injecting complexity, but rarely you're right · 2018-10-03T15:01:36.129Z · LW · GW

From a purely pragmatic perspective; conversation is a tool for getting what you want. There exists a spectrum from simplicity to complexity; and favouring one over the other is really just a case of the grass seeming greener on the other side of the fence, imo.

There are situations where it pays to simplify your point, and situations where it pays to get deep and dirty. I wouldn't hesitate to guess which type of situation is more commonly encountered, so it seems to me that there's no readily applicable heuristic for this problem - you just have to take each conversation as it comes.