Ask HN: What do Microsoft employees think about the new Scroogled campaign?
See http://www.scroogled.com/
My suspicion is that Microsoft's current spate of negative advertising can be traced directly back to the Mac vs PC ads of a few years ago. These happened to coincide with a remarkable rampup in the popularity of Apple's PCs, and that cannot have gone unnoticed at the C-levels. Whether or not the ads were actually a driving factor in the change is, of course, hard to say -- but they certainly didn't seem to discourage anyone from buying Apple.
What the decision-makers seem to have missed, though, was that 1) the ads themselves were gentle and somewhat charming (or at least John Hodgman helped make them that way) and 2) although these things were largely exaggerated for comic effect, they often targeted real pain points that consumers actually had with Windows.
Of course, in implicitly painting Microsoft as buffoonish and perhaps even incompetent, I think these ads generated more rage in the boardroom than they would have if they'd been merely full-on attack ads in the style of "Scroogled".