I think if you have a good mentor or guide in a space where there might be a proprietary system, it’s a lot easier to start being able to do those deep dives.
I found that when people were able to explain the larger context for the question I was asking, I would be able to move along faster and deep dive, but with brief answers that didn’t really go beyond my surface level questions, I ended up having to ask a lot more questions, sometimes finding certain information was never documented.