Supervisors often prefer rule breakers, up to a point

Fundamentally, rules almost always come with compromises — for the sake of making rules understandable by humans, they have to be relatively simple. Simple rules for complex situations will always forbid some amount of good behaviour, and allow some bad behaviour. Many of society's parasites live in the space of "allowable bad behaviour", but there is a lot of value to knowing how to exploit the "forbidden good behaviour" space.

Example?

Going 10mph over the speed limit on a highway, especially because you’re a little late, isn’t a big deal.

Going 5mph UNDER in a neighborhood with kids playing around on the street is too fast.