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I recall one particularly vivid experience with a customer who seemed to be dumb as a post. But he kept getting what he wanted, and it took some time to realize I'd underestimated him.

His superpower wasn't his wit, it was getting things he didn't really deserve. His bosses saw that, which is why he was in charge. He would ask for things that sounded very reasonable, and every time we said yes our profit margins went down.

Every boss who has loyal employees that make 10% less than they deserve gets recognition from the organization for getting things they aren't really entitled to. That's why your 'nice' boss often seems to get stuck. They only succeed if you go out of your way to make them look good.



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