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2.
Refer's to Dilbert's boss, but also by association to all other mindbogglingly stupid bosses lacking foresight, technical knowledge, leadership skills, morality or tact.
"I'll get next weekend off, but I'll have to work on the PHB."

"My new job's ok, except there's a classic Pointy Haired Boss in my department."
by master_gopher June 30, 2006
 
1.
Etymology: A character in Scott Adams' Dilbert comic strip

(n) a clueless boss, esp. one that has been over-promoted and uses a lot of meaningless corporate buzzwords
My pointy-haired boss just told me I need to make a paradigm of strategizing my primary action items, just because I forgot to use the new cover sheet on the TPS reports.
by BeardedFatass January 11, 2004
 
3.
A sociopathic boss that is also the most inept, stupid human being alive.
Dilbert is managed by a Pointy Haired Boss.
by Colin Ritter August 06, 2003