"Relearning the Art of Asking Questions"

"Because expectations for decision-making have gone from “get it done soon” to “get it done now” to “it should have been done yesterday,” we tend to jump to conclusions instead of asking more questions. And the unfortunate side effect of not asking enough questions is poor decision-making. That’s why it’s imperative that we slow down and take the time to ask more — and better — questions. At best, we’ll arrive at better conclusions. At worst, we’ll avoid a lot of rework later on.

Aside from not speaking up enough, many professionals don’t think about how different types of questions can lead to different outcomes. You should steer a conversation by asking the right kinds of questions, based on the problem you’re trying to solve. In some cases, you’ll want to expand your view of the problem, rather than keeping it narrowly focused. In others, you may want to challenge basic assumptions or affirm your understanding in order to feel more confident in your conclusions"
https://hbr.org/2015/03/relearning-the-art-of-asking-questions?utm_source=pocket&utm_medium=email&utm_campaign=pockethits

I think the problem is also that some workplaces don't trust questions, that people are implicitly socially punished when they ask for help or contextual information.
Frustratingly, I have often founs that people will say 'let me know if you have any questions!' but then deeply overreact to actually being asked a question. Like, they will assume that my question is an indication that I fundamentally don't understand and need to hear the entire explanation of the project again (in a way that typically, again, doesn't directly address my question). Or, that my asking a question means that I am not equipped to complete the task and I want someone to come do it for me.
So, there is also training needed in listening and supporting question-askers.