I think this person says it all.
"But here’s my problem. The idea of the campaign seems to be to show people how great Microsoft products are. The “real people” as they keep calling them are being reached out to so they can understand and grow to love these products.
But…If Bill (and therefore Microsoft) is not already in touch with real people, then their products may not be, either. By spending time with real people, the logic flow suggests they’ll be able to build better products.
In other words, Microsoft is highlighting the fact that they are out of touch. But instead of saying they’ll mingle with real people to build better products, the message seems to be that the real people need to get with the program.
In other words, I’m confused. Perhaps I’m just over thinking the whole thing, but it seems like exactly the opposite message that Microsoft needs to be sending."