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Turgurth comments on "Stupid" questions thread - Less Wrong Discussion
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The standard reference for this is "How to Win Friends and Influence People" by Dale Carnegie. I have not read it myself.
Much of it boils down to gothgirl420666's advice, except with more technical help on how. (I think the book is well worth reading, but it basically outlines "these are places where you can expend effort to make other people happier.")
One of the tips from Carnegie that gothgirl420666 doesn't mention is using people names.
Learn them and use them a lot in coversation. Great them with their name.
Say thing like: "I agree with you, John." or "There I disagree with you, John."
This is a piece of advice that most people disagree with, and so I am reluctant to endorse it. Knowing people's names is important, and it's useful to use them when appropriate, but inserting them into conversations where they do not belong is a known influence technique that will make other people cautious.
(While we're on the subject of recommendations I disagree with, Carnegie recommends recording people's birthdays, and sending them a note or a call. This used to be a lot more impressive before systems to automatically do that existed, and in an age of Facebook I don't think it's worth putting effort into. Those are the only two from the book that I remember thinking were unwise.)
Be judicious, and name drop with one level of indirection. "That's sort of what like John was saying earlier I believe yada yada."
It probably depends on the context. If you in a context like a sales conversation people might get cautious. In other context you might like a person trying to be nice to you.
But you are right that there the issue of artificialness. It can be strange if things don't flow naturally. I think that's more a matter of how you do it rather than how much or when.
At the beginning, just starting to greet people with their name can be a step forward. I think in most cultures that's an appropriate thing to do, even if not everyone does it.
I would also add that I'm from Germany, so my cultural background is a bit different than the American one.
This is how to sound like a smarmy salesperson who's read Dale Carnegie.