Fun fact: Linguists talk about this in the context of the Gricean maxims, http://en.wikipedia.org/wiki/Cooperative_principle
Maxim of Quality[edit] Do not say what you believe to be false. Do not say that for which you lack adequate evidence.
Maxim of Quantity[edit] Make your contribution as informative as is required (for the current purposes of the exchange). Do not make your contribution more informative than is required.
Maxim of Relation[edit] Be relevant. With respect to this maxim, Grice writes, "Though the maxim itself is terse, its formulation conceals a number of problems that exercise me a good deal: questions about what different kinds and focuses of relevance there may be, how these shift in the course of a talk exchange, how to allow for the fact that subjects of conversations are legitimately changed, and so on. I find the treatment of such questions exceedingly difficult, and I hope to revert to them in later work."[1]
Maxim of Manner[edit] Avoid obscurity of expression. Avoid ambiguity. Be brief (avoid unnecessary prolixity). Be orderly.
Relying on the other's inference is critical in a lot of communication, along many dimensions, and people manage to do it all the time by following these rules (most are learned through typical social interaction, but execution can always be improved).
If you want to be super-direct, go for it, but if you earnestly keep in mind the other person's state of mind, and the above maxims, you'll usually have no problem navigating guess culture (unless you're making a transition between countries or something similar).
Followup to: Ask and Guess
Ask culture: "I'll be in town this weekend for a business trip. Is it cool if I crash at your place?" Response: “Yes“ or “no”.
Guess culture: "Hey, great news! I'll be in town this weekend for a business trip!" Response: Infer that they might be telling you this because they want something from you, conclude that they might want a place to stay, and offer your hospitality only if you want to. Otherwise, pretend you didn’t infer that.
The two basic rules of Ask Culture: 1) Ask when you want something. 2) Interpret things as requests and feel free to say "no".
The two basic rules of Guess Culture: 1) Ask for things if, and *only* if, you're confident the person will say "yes". 2) Interpret requests as expectations of "yes", and, when possible, avoid saying "no".
Both approaches come with costs and benefits. In the end, I feel pretty strongly that Ask is superior.
But these are not the only two possibilities!
"I'll be in town this weekend for a business trip. I would like to stay at your place, since it would save me the cost of a hotel, plus I would enjoy seeing you and expect we’d have some fun. I'm looking for other options, though, and would rather stay elsewhere than inconvenience you." Response: “I think I need some space this weekend. But I’d love to get a beer or something while you’re in town!” or “You should totally stay with me. I’m looking forward to it.”
There is a third alternative, and I think it's probably what rationalist communities ought to strive for. I call it "Tell Culture".
The two basic rules of Tell Culture: 1) Tell the other person what's going on in your own mind whenever you suspect you'd both benefit from them knowing. (Do NOT assume others will accurately model your mind without your help, or that it will even occur to them to ask you questions to eliminate their ignorance.) 2) Interpret things people tell you as attempts to create common knowledge for shared benefit, rather than as requests or as presumptions of compliance.
Suppose you’re in a conversation that you’re finding aversive, and you can’t figure out why. Your goal is to procure a rain check.
Here are more examples from my own life:
The burden of honesty is even greater in Tell culture than in Ask culture. To a Guess culture person, I imagine much of the above sounds passive aggressive or manipulative, much worse than the rude bluntness of mere Ask. It’s because Guess people aren’t expecting relentless truth-telling, which is exactly what’s necessary here.
If you’re occasionally dishonest and tell people you want things you don't actually care about--like their comfort or convenience--they’ll learn not to trust you, and the inherent freedom of the system will be lost. They’ll learn that you only pretend to care about them to take advantage of their reciprocity instincts, when in fact you’ll count them as having defected if they respond by stating a preference for protecting their own interests.
Tell culture is cooperation with open source codes.
This kind of trust does not develop overnight. Here is the most useful Tell tactic I know of for developing that trust with a native Ask or Guess. It’s saved me sooooo much time and trouble, and I wish I’d thought of it earlier.
"I'm not asking because I expect you to say ‘yes’. I'm asking because I'm having trouble imagining the inside of your head, and I want to understand better. You are completely free to say ‘no’, or to tell me what you’re thinking right now, and I promise it will be fine." It is amazing how often people quickly stop looking shifty and say 'no' after this, or better yet begin to discuss further details.