Supervisors often prefer rule breakers, up to a point

A more palatable phrasing, "supervisors prefer people that engage with the rules with purpose." That is, choosing to break a rule because you are making a cost call based on what you were able to achieve is not, necessarily, a bad thing.

The "point" where this fails, of course, is where the "cost" call above is such that the supervisor can't agree.

You sound like a supervisor there ;)

“They didn’t break the rule! They engaged in the rules with purpose unlike those rule followers.”

Though I’m not advocating your approach is incorrect.

Someone who follows the rule even when it produces a terrible outcome is a painful liability. Just like someone who breaks the rule to do the same thing.

Worse, I'm a parent! :D

Sometimes, the goal is to create an environment where people must break certain rules to get anything done, which everyone (including supervisors) understands, but by way of imposing those rules responsibility and liability is transferred to subordinates.

The use of private internet access for work is denied. Doing so, shifts all responsibility from the IT-department on the private citizen. The WiFi is currently out of service.

I think those environments are bad, most likely? Why would it be a goal to make it so that people break rules?

Making people think about the rules? That is fine and good. Setting them to be broken, though? That just sounds broken.

Like anything it's a balance.

On one extreme you have crap like the gig economy where workers have all of the responsibility and none of the control.

On the other extreme you have perverse workplaces where there would otherwise be no individual responsibility for work if people were not taking on that responsibility by working outside the rules.

I do think that having the system and the rules support the way the organization actually runs in reality is better than even a good implementation of systematic rule breaking.

> Someone who follows the rule even when it produces a terrible outcome is a painful liability.

It is called malicious compliance for a reason.

It gives the rule setters leverage over the masses. “Show me the man and I’ll show you the crime”