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[Literally] "[Pointy Haired Boss]" as featured in the long running Dilbert cartoons by Scot Adams. The phrase suggests an office manager with above average [incompetance], general cluelessness and an ability to prevent anyone else in the office from doing any useful work. Actual pointy hair is not a requirement for PHBs, but there is strong annecdotal evidence that they will rapidly develop the distinctive hairstyle.
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