There is a famous phrase in the literature of linguistic pragmatics that illustrates just how complex and context-dependent the act of communication is. On reflection it also tells you a great deal about how insanely sophisticated the human brain is to decode the meaning of conversational implicatures without much effort, a feat that is beyond current artificial intelligence. As far as I know even the infamous Watson can’t do it. What are conversational implicatures you ask? Let’s turn to that famous phrase for insight:
Q: How are you doing in your new position at San Andreas Fault University?
Pamela: Well, I haven’t been fired yet.
How much information can you infer about Pamela’s current state of being from the simple proposition she offers to encode that information? Probably a lot more than the fact that she is still employed. Probably even a more direct and satisfying answer to the question. Pamela is not doing well. How do I know? She offered a conversational implicature by not answering the question directly.
Communication could be described as a game where the participants try to transmit as much information as possible with as little effort as they can get away with in order to engage in a meaningful exchange. Every piece of information that is introduced to the conversation is evaluated against the background of the knowledge of the participants and what they know about each others knowledge and how relevant the information is to the information that was previously introduced and how new the information is compared to the pieces that are available on the table of our short term memory in this jigsaw puzzle of a conversation. Sounds confusing in theory? Thankfully this information game is not a battle of wits to the death with a Sicilian.
As long as all participants in a conversation are aiming to have a meaningful conversation the WIFOM dilemma (Wine In Front Of Me) will be resolved by the willingness of all to not have it escalate ad infinitum. At some point everybody just agrees that they understand each other well enough not to try and engage in mind reading any further. Evolutionary game theory (sic!) is your friend here if you are a stickler for details.
The will to communicate meaningfully is the key determining factor for the game to work, by the way. Only if I assume that you mean to tell me something will I try to decode what you are saying, even if I don’t understand it completely at first. A lot of logical operations in the game are contingent upon this assumption of mutual cooperation. Cool Hand Luke, the pop culture hero of defiant communication, knows what to make of the seemingly counterfactual proposition the Captain is conveying to the chain gang. There is no failure to communicate. There’s just a Captain telling his subjects to submit themselves to his world view, or else…
Thus the key to not fail at communicating when you are trying to get your message across is to think ahead in the game. Think about what the recipients try to infer from the pieces of information that your message contains by learning what they already know and how the puzzle looks from their point of view. The same holds true if you are receiving information and try to decode it. Especially in intercultural communication the same propositional content can have very different meanings to each party in a conversation because the background knowledge of the participants differs greatly. Even when they both speak English, as this little piece of advice from The Economist will tell you: “Euphemistically Speaking”