I understand what you say; you want people to solve problems, not to execute tasks. But, there're some points that I figured out myself during my career that may be useful:
> I want them to figure it out
Can they actually figure it out without someone explaining some oddly specific detail related to the company/domain/country?
If you have some very precise requirement that you absolutely want to be satisfied, are you telling them, or do you expect them to "figure it out" because "it's the only right way to do it"?
If they cannot figure it out, and they cannot REALIZE they should have until too late, will they be punished for their mistakes, or are they allowed to make mistakes while learning by themselves?
I find that many people, especially bosses/managers/CEOs/whoever has/thinks having the power, think that their view is the Only One View; who does things differently is Just Wrong (as you say yourself about your past bosses), but they DO NOT CARE about explaining their wishes to whoever is working with them. Since this is quite a prevalent attitude, people tend to ask details about their jobs. This isn't bad, and most people, once they feel safe and properly valued, just stop, in my own experience.
You're right, but it's not even really an "attitude", and it's not necessarily malicious or even stemming from a power relationship.
It's just a fundamental cognitive blind spot that humans have about assuming that what's obvious to ourselves is obvious to everyone else. Every one of us who's jumped into a question about something they're working on and had the other person say "I don't understand the context" has done this.
The opposite is what makes great teachers, authors, and other communicators great: they recognize what the other person doesn't understand.
You can't just go around recognizing what people don't understand. That's what got Socrates killed. You've gotta make them understand what they don't understand without making them want to kill you. That's what makes a great teacher / leader / etc.
I have found the Socratic Method[0] brings out the best outcomes because it forces everyone to show what they think they know, have their assumptions tested and hear about things they might not have considered or even know about. From my experience, everyone is ultimately able to reach a higher level of understanding for the topic or problem which allows for better decision making. The more diverse the participants' backgrounds the larger the network of knowledge one is able to tap into.
Unfortunately, you are right that there are people who are extremely threatened by the Socratic Method. In Plato's Cave[1], Socrates talks about how some people strive to explore and learn while others have no desire to broaden their knowledge as "they know no better life."
Requirements or the asks need to be clealy documented before someone goes for a solution. The problem usually is they discover more use case while reasearching the solution.
> Every one of us who's jumped into a question about something they're working on and had the other person say "I don't understand the context" has done this.
Sometimes. Not always. I think everybody holds ideas in a spectrum from "absolute truth" to "totally my biased opinion". The problem arises if I hold an opinion as an absolute truth and I ask other people to work for me. I won't bother about telling them absolute truths, won't I?
Doing things differently is not only wrong, its also often perceived as a power-play challenge. For if the captain does not steer the ship, what good for is a captain? So the creative worker, is perceived as a challenge by lots of management, that thinks it has to defeat this with micro management.
I think that some commenters kind of misinterpreted my message. I think that just any of us has wishes and ways "to do it".
If I ask somebody to cook for me, I expect the food to be palatable _to me_. But since I'm Italian, I'm probably picky about food, and I may not like some kind of exotic tastes. That's totally ok.
What is not ok is to say to somebody "cook for me", then classify the food as shit because "I don't like it". I should probably investigate a bit with the other person about my tastes (and the other person should, rightfully, ask questions!). They will still have plenty of opportunities to exercise their creativity, without pushing too many boundaries. Mind you: I think that boundaries should be pushed, but it's unwise to push them too hardly at first.
> I want them to figure it out
Can they actually figure it out without someone explaining some oddly specific detail related to the company/domain/country?
If you have some very precise requirement that you absolutely want to be satisfied, are you telling them, or do you expect them to "figure it out" because "it's the only right way to do it"?
If they cannot figure it out, and they cannot REALIZE they should have until too late, will they be punished for their mistakes, or are they allowed to make mistakes while learning by themselves?
I find that many people, especially bosses/managers/CEOs/whoever has/thinks having the power, think that their view is the Only One View; who does things differently is Just Wrong (as you say yourself about your past bosses), but they DO NOT CARE about explaining their wishes to whoever is working with them. Since this is quite a prevalent attitude, people tend to ask details about their jobs. This isn't bad, and most people, once they feel safe and properly valued, just stop, in my own experience.