1. (adj.) An esp. stupid person who may or may not be your boss. Often associated with managers and stupid bosses, the phrase was coined in the daily comic strip "Dilbert" by Scott Adams, in which Dilbert's boss (Pointy-Haired Boss happened to be his name) had a pointy, devil-horn-like haircut and was especially stupid and over-promoted.
1. Our new mission statement is "We envision to authoritatively foster quality intellectual capital while maintaining the highest standards." Whoever made that up must have been pointy-haired.