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Pointy-haired is a term that is applied to a type of business professional who is different from normal computer professionals. Pointy-haired people are known for their extreme qualities that set them apart from computer professionals, and are often seen as out of touch with technology. The term came into use owing to the popularity of the extremely strict and eccentric boss character in the Dilbert comic strip.
Pointy-haired is an adjective and is applied only to people and never to ideas. The term was made popular by a character from the Dilbert comic strip. The character behind the term is a pointy-haired boss known for his eccentric behaviors, micromanagement and incompetence, yet somehow retaining his power in the workplace. This term is hence applied to people in the computing profession who are not hackers and are more similar to the suits and marketroids of the computing world.
Suits are non-hackers who wear uncomfortable business clothing. Marketroids are people from the marketing department who are specialized in convincing the customers that a specific difficult or impossible-to-implement functionality or service will be delivered to them. These buzzwords along with the adjective pointy-haired are often used to denote people who are incompetent yet somehow able to survive in the corporation.
Pointy-haired is often used in conversations among techies and often denotes incompetent yet powerful middle managers. A typical example usage of the term is given below:
"The pointy-haired ordered me to use Windows OS, but I set up a Linux server with Samba instead."