“Just learn the callouts” is less helpful than people think

Trying to learn a map with people who already know it has shown me a problem: they use callouts to explain the callouts.

“Go past the thing near the other thing” is not information if both things have nicknames you have never heard. I do not need somebody to stop the whole game for me, but a landmark and a direction would help more than repeating the same unfamiliar word louder.

If you are teaching someone, what actually works? And if you are the new person, how much asking feels reasonable before you start worrying you are annoying everyone?