This won't end well. Microsoft is a bubble with an echo-chamber internally. Their employees are in the 1990s era, which is making DVD application software (Word, etc.). The problem is that they still think that way. Senior managers are from the 1990s. Or they hired from colleges and sheep dipped people in the same thinking. People from startups and industry don't last long there, and definitely don't rise in management.

The reason startup or industry people don't rise in Microsoft is that they are rejected as not matching the 1990s way of doing things.

Examples: Their UI innovation was in WPF because someone forgot to tell them that UI dev now happens on web pages and iPhone. Hotmail is a joke. MSN is a joke. Web hosted office 365 is a joke. Exchange web UI and client main usage is for 1990s customers and not 2010 customers. C# is charging in the opposite direction of the entire webapp industry's development platforms. (aka, they were late to MVC, Hadoop, Linux server hosting, etc.) They push Windows OS lock-in to win (but that fails).

The right leader comes from Silicon Valley in a startup gone big. That right leader will then replace many of the other leaders in MSFT with Silicon Valley highly strategic leaders. When the CEO is a Microsoft person, they will keep the same Microsoft 1990s style internal leaders and nothing will change in the category of what needs to change.