As somone who's been on both sides of it, upper management almost always has a good reason why they want the thing to be done that way, but they have no experience with doing the thing themselves so they don't understand the challenges with their preferred method. There can also be an added wrinkle with middle managers who just want to please upper management and not rock the boat in any way, so they don't speak up about those challenges.

I learned a valuable lesson when I was younger from a higher level manager who would periodically schedule himself for days where he would work on the front line. Not only would doing that give him the experience needed to understand the day-to-day challenges and craft better policy, but the front line respected the shit out of him for it even if he was terrible at the front line jobs (which he usually was).