The bill does come due. I've seen it happen over and over. But management fails to connect current problems to past mistakes, especially when they happen over the course of years. Thats setting aside when they insist that the correct decision was made, but have no real evidence that this is the case, other than the fact that "things worked out" even though maybe it would have been better had a different decision was made.

People do get a pass on this -- you can't rigorously examine every decision and counter-factual or you'd never make forward progress. And I don't really have any great ideas on how to bridge this gap. It'd be nice if there were better ways to measure this but there aren't, so it really comes down to who is more convincing, which is often orthogonal to facts and correctness.