I work in medical and there the top guys often make decisions that are really hard to implement in software. If they understood only a little of the consequences of their decisions have they would probably think a little more about the rules they are creating.

I see the same in product development. Marketing comes up with something that has words like "most of the time", "sometime" or "somehow" in the description. Really hard to impossible to implement. When I ask them what they really want to achieve we usually end up with something simpler and straightforward that fulfills the needs, is well understood and easy to implement.

I think in government with most of the work being outsourcend this feedback loop doesn't exist. A committee comes up with something and the contractor implements it without questions asked. The more complex the work, the more money for the contractor.