(retracted, see below)
Incentives explain a lot. Add to that incomplete information and intellectual and emotional biases. There are reasons that large organizations are often such hell holes.
Another help is evolutionary theory. If an organization actually solves a problem, it will cease to exist. But if it makes the problem worse, it will be eternal and grow without bounds.
Just giving a short table-summary of an article by James Shanteau on which areas and tasks experts developed a good intuition - and which ones they didn't. Though the article is old, the results seem to be in agreement with more recent summaries, such as Kahneman and Klein's. The heart of the article was a decomposition of characteristics (for professions and for tasks within those professions) where we would expert experts to develop good performance:
Static stimuli
Decisions about things
Experts agree on stimuli
More predictable problems
Some errors expected
Repetitive tasks
Feedback available
Objective analysis available
Problem decomposable
Decision aids common
Dynamic (changeable) stimuli
Decisions about behavior
Experts disagree on stimuli
Less predictable problems
Few errors expected
Unique tasks
Feedback unavailable
Subjective analysis only
Problem not decomposable
Decision aids rare
I do feel that this may go some way to explaining the expert's performance here.