I've never been a huge fan of Dilbert. I do admire Scott Adams' ability to get decades of mileage and merchandising royalties out of essentially one joke, and there are times that the corporate ennui of the strip provides some laughs. But Dilbert's arrogant perception of his own worth never appealed to me, and the Dogbert stuff is forgettable. I will say this - I love the Pointy-Haired Boss (PHB). I love his ability to navigate the choppy seas of middle management with practiced indifference to the woes of his subordinates and the deft avoidance of true culpability for his department's failures. He is the pinnacle of bureaucratic evolution, the boss who has no idea what he's doing but manages to spread buzzword bullshit both up and down the ladder so effectively that he not only endures in his sinecure but thrives.
Anyone who has worked in an office environment is intimately familiar with the Bill Lundberg archetype. Ass-kissing, buck-passing, empire-building, soul-crumbling, time-wasting, self-promoting narcissists with an eye only on their own career and the next rung in the ladder. The rank and file employees who actually do the work exist only as grist for these dime-store business-school supervisors to grind in the mill, peons whose successes are readily appropriated and whose failures are swiftly condemned. It's a tough job, taking credit for other people's work and blaming them for your shortcomings, but it's a living.
The best part about the PHB is that while he's relatively stupid (at least compared to the technologically bright but socially impaired engineers of his division), he exhibits a masterful cunning in his native environment. He has mastered the art of screwing his fellow managers, protecting his budget, and avoiding any consequences for his incompetence. He's risen to the middle because his corporate masters value what he brings to the laminate conference table - blind obedience to higher-ups and blase disregard for subordinates.