It is important to note that these are not the only two options. The toxic part of Guessing is that they judge others for Asking. It is possible to be a "Friendly Guesser" who tries to Guess other people's intentions but also allows others to Ask.
The Secret of Our Success by Joseph Henrich talks about that, but it was published in 2015, after your comment, so that is probably not the one you were thinking of...
There are some things which it's impolite to say, in any words, because the sentiment is impolite--for example, "I don't want you to come to my party." Guess culture, applied well, allows you to avoid having to say those things or cause the attendant hurt feelings. (Guess culture applied poorly avoids the hurt feelings but puts you in the awkward position where they're at the party anyway because you felt compelled to invite them.) The same situation in ask culture requires you come out with it.
How would "guess culture applied well" look like in this situation?
Could you please elaborate on this with some examples? I would love to hear more about it.
There's a conflict which features lying, but it's a coalition of founders and investors against regulators and customers.
In that case it is important to shout from the rooftops that, while it may be rational for the players, this game is malicious. It is played with evil intent.
What examples of flaws do you have in mind here?
People with autism spectrum disorders may be less aware of the social web and react awkwardly when the web tries to pull them into place...
- Spend thousands of dollars on therapists but would never do a half-hour debugging session with a friend because "that would be weird".
This suggests that this kind of debugging is a well-established rationalist self-improvement practice. Could you please tell me where I can read more about this kind of practice? :)
The original of the shoggoth meme and its relation to H.P. Lovecraft's shoggoth
This link is broken. It contains several different URLs mashed together. Was it meant to be a footnote instead?
What examples do you have in mind here?