As a manager the way I approach rules with my reports is I always tell them to understand the "chesterton's fence" behind any rule. I looks at rules like business logic in code, the "logic" was added there for a reason but there are often edge cases where that logic does not apply. I don't tell my reports to either break or follow any particular rule, but to understand why that rule is there before they decide if they need to either follow or break it.

And from personal experience i find that when you give people that level of autonomy, they will almost always approach what I told them about rule breaking in good faith.