Rules That Were Supposed to Help But Ended up a Big Fail

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Bring the Glazed Peace Offering!
The rule at my workplace was that if you were late, you had to bring donuts for everyone.
People quickly figured out that the cost of being 4 hours late was to bring donuts. As a result, if you were running late, you just had a slow, easy morning and stopped by to pick up donuts on your way in.
Our boss, who had put the rule into place, thought it was funny and just let it continue. He was an easygoing guy and REALLY good at motivating people. Letting them get away with this sort of thing meant they stayed late or showed up after hours for emergencies.