Most of what's being written is wrong.
Penn's job will not be to design products, or look into the future. He's being brought in to use his knowledge of polling and lobbying to advise Microsoft on its messaging.
Penn is at the end of his career, and was close to both President Bill Clinton and former presidential candidate Hillary Clinton. A Democratic operative, he was being sidelined, marginalized, and even ridiculed by the party's new liberal base, and by people around President Obama.
He needed an exit. Microsoft offered him one.
Penn's calling card is as author of a recent book called "Microtrends: The Small Forces Behind Tomorrow's Big Changes," which argued that the broader market is increasingly divided into small niches, and that companies can profit by focusing on each niche separately. What that might point to is more differentiation among Microsoft products, and more targeted marketing at small groups within the population. If Penn can focus Microsoft's marketing in this way, it will be worth the money. If Microsoft chooses to ignore him, as it does most consultants, at least he'll get a paycheck.
Microsoft needs to shake things up badly, as its image as a leader has faded steadily ever since Steve Ballmer became its CEO. Ballmer, just a year younger than co-founder Bill Gates, comes across as crass and oafish, a used-car salesman rather than a slick technologist. Microsoft's marketing has taken on a bull-in-a-china-shop appearance that badly needs updating.
If Penn can help with that, he's a bargain. If he can't, it's no big loss. Microsoft continues to do well in the general business market. Bigger profits on the consumer side would be a bonus.
Disclosure: I am long MSFT.