While Microsoft may often come across as a monolithic corporation, it's sometimes good to remember that behind the company are individuals and personalities. So it's always nice to see them have a little fun, which is what you see above.
The video is taken from MGX FY12 and like Long Zheng who found this vid, while we don't know the context, we still find it funny nonetheless. The four unlucky carpoolers are Kurt DelBene (President of Office), Qi Lu (President of Online Services), Chris Capossela (Senior VP of consumer marketing) and Andrew Lees (President of Windows Phone) who we briefly spoke with in Barcelona. Yeah, that Andy Lees, which is what makes the Windows Phone comment that much more funny.