Whenever I ask questions, I tend to go to the very bottom of it. And I am not satisfied as long as I get a very intuitive and fundamental understanding of the topic. I have seen, however, that this can be tiring. Unless you are having the conversation with someone who has the time, willingness, and the knowledge to satisfy my curiosity, it is pointless to keep probing. People would often be exasperated or would be unable to provide me the intuition.
Therefore, these days, I pretty much probe very little and if it seems that my questions won't really be answered, I leave it at that, mentally noting to do some independent research on the internet.
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This is especially tough because of how much skill it takes for you the questioner to not make the other person feel stupid when they realize they can't answer your questions.
Yeah, I think the other thing that's made me shy away from it more as I've gotten older is asking the "stupid" question, getting a jargon-laden response, and realizing: this person isn't equipped to communicate the concept. It can be pretty exhausting to be the questioner in that case.
Sometimes there are details one doesn't need to know to make a good decision. All of mathematics is built on this.
However this only works when there is enough knowledge to know why the unimportant details won't matter.