I've found that the most useful discussions I've had are around how the people up the ladder think about the junior persons area/projects and how it fits into the bigger picture.
The junior person knows more about the details and the senior person should understand more about the strategy so both have a chance to learn from each other and to each walk away with a better overall perspective.
As a skip level manager myself it's also seems like a better use of everyones time than me answering generic questions.
That's helpful as it gives me a sense of how I can also try to bring value to the meeting. What kind of questions have you found useful/practical from these meetings? I always want to be careful not to ask something that comes off too basic or uninformed.
The junior person knows more about the details and the senior person should understand more about the strategy so both have a chance to learn from each other and to each walk away with a better overall perspective.
As a skip level manager myself it's also seems like a better use of everyones time than me answering generic questions.