4. Windows 7 is a solid, compelling upgrade over Windows XP.
Windows XP support and security updates are drying up very soon. Many enterprises, knowing where they are in the Microsoft published support lifecycle, have Windows 7 hardware and software refresh programs underway. Having skipped Vista, these companies are standardizing on Windows 7, and they won't be in the market for another desktop upgrade for at least three to four years. ( Going from Windows XP to Windows 8 is not recommended.) Furthermore, few companies will consider hybrid deployments of Windows 7 and Windows 8, since that's a support nightmare. In short, enterprises will probably pass on Windows 8.
There's very little compelling reason to upgrade to Windows 8 from Windows 7. There are a few nice new features in Windows 8-including Windows To Go, a faster boot sequence and better BitLocker support-but even in the aggregate they simply don't justify a deployment effort, and the attendant retraining, to thousands of employees.
When it comes to Windows 8, Microsoft has stopped telling you that Windows 7 is simply good enough-but it's true. Waiting for Windows 8 doesn't buy you a lot. It's a painful reality for the software giant, but a very real one indeed.
5. Microsoft's Roadmap Is Fuzzy.
Even if the company had a solid vision going forward, you wouldn't get to see it. This very clear move to mimic Apple aims to do two things- drive consumer product demand and keep Microsoft's moves very secret, thereby building a monumental buzz when the products are unleash onto the world all at once.
The end result is an almost-total reduction in the amount of disclosure Microsoft makes to its customers about products and services in its pipeline. Whereas customers were along for the ride on every milestone and delay for Windows XP, Windows Vista, Windows Server and so on, now we have very little idea when Windows 8 is coming except "this year."
Commentary: Is Microsoft too old and too big to survive?
Also consider the state of Windows 8 and Visual Studio 2012. Windows 8 is now going to have a brand new UI outside of the Metro-style desktop, but that won't even be made public until the product is released to manufacturing. Why make such large changes to of all things the user interface-not just the usual big fixes-this late in the game? It speaks to disorganization.
Couple this with some of the changes that have been made to the next version of Visual Studio. Customers are screaming to reverse many of the UI changes that the company keeps making to its product even at these hypercritical junctures very close to scheduled releases.
Looking at these five points, you can't help but think that Microsoft faces myriad problems, ranging from too many cooks in the soup to driving individuality in the face of corporate control to simply lacking a grand plan other than "the cloud." Only time will tell if these problems can be solved-but the tea leaves are there for you to read.
Jonathan Hassell runs 82 Ventures, a consulting firm based out of Charlotte. He's also an editor with Apress Media LLC. Reach him via email and on Twitter. Follow everything from CIO.com on Twitter @CIOonline, on Facebook, and on Google +.
Read more about Windows 7 in CIO's Windows 7 Drilldown.