Entropy suggests that we gain the most insight on a question when we take it to the friend, colleague, or mentor of whose reaction and response we're least certain.
And it suggests, perhaps, reversing the equation, that if we want to gain the most insight into a person, we should ask the question of whose answer we're least certain...
Pleasantries are low entropy, biased so far that they stop being an earnest inquiry and become ritual. Ritual has its virtues, of course, and I don't quibble with them in the slightest.
But if we really want to start fathoming someone,
we need to get them speaking in
sentences we can't finish.”
― Brian Christian