My current approach is to take calculated risks in conversions, given that I go through a catalog in my head "what if I say this, or that, or that?", the temptation being ruling every single one out until eternity and holding the silence. Also, it helps to be ok with not having a lot to talk about, eventually flowing and natural conversations become easy over time with the same person; but for casual encounters where impressions aren't too important (like working with a client at work but not sales job), I take risks here and there like I said, but if I strictly stick to the matter at hand (strictly business) and said nothing in between, I would be fine with that too, even if the other person would prefer to talk more.