What I learned at Microsoft
This is the start of a new category - "What I learned [while employed] at Microsoft". Nothing here will be NDA material, but it'll give you an insight into the non-Borg nature of the company.
Oh - and the non-Borg-ness? That I learned well before going to work at Microsoft - there are so many people there, it'd be impossible for there to be a hive-mind. This explains why stuff that "Microsoft should know" is actually not known by all at Microsoft.
The first one's easy.
The most common reason given for missing meetings, or arriving late?
"Sorry, Outlook ate my invite."
If Microsoft (or, rather, the Outlook team) wants to improve Outlook, a little inward-look would help them discover some of its more obvious pain-points. After that, the Outlook team should look outward to the people who use functionality that Outlook is supposed to support, but which isn't core to the way Outlook is used at Microsoft. For instance, people who use Outlook with a generic POP or IMAP server, rather than with Exchange. There are things that Outlook can't do now, that POP clients of a decade or two ago handled without complaint.
My favourite example is that of downloading the same message twice, the second time being after a connection interruption. Truly frustrating if you're faced with a few hundred email messages to download from a hotel room with dodgy dialup.