4. "Dear Helpdesk, how do I turn off my computer?" - User training and acceptance is a massive consideration. I only listed it fourth because if you don't have a device to install an OS, stable drivers to run it properly, and apps to run on the OS, you wouldn't put it in front of people. Unlike the move from Windows 95 to XP to Vista to 7, Windows 8 is not just a different looking start menu: there is no start menu. You no longer access the start menu to shut down. In fact, there is no default shut down option displayed on the UI when the user is logged in. These seemingly very small things can be a huge disruption for even tech savvy end users. The better bet is to let users educate themselves through a few years of use on their own at home and then capitalize on this user-funded training to introduce the device at work.
5. Consumerization security, and the network edge - On the surface Windows 8 looks and behaves like a consumer product and you better believe the early success of Windows 8 will be with consumers. Everyone has taken their iPads to work and Microsoft expects you to do the same with a very capable Windows 8 slate device. This is tricky because individuals' decision to work from a Windows 8 slate is out of a CIO's control. The upside is that since it is a Windows device, it is much more manageable than non-Windows devices. At a minimum, any consumerization or de-perimeterization initiatives need to be driven by carefully conceived IT policy.
6. Tick-tock but not of the clock - There are releases of Windows that overhaul the entire code base (the so-called "tick" such as Windows 95 and Windows Vista) and there are releases that build off of or extend an existing core code base (the "tock" like Windows XP and Windows 7). Technically, Windows 8 is a tick release, which most organizations wait until at least the first Service Pack to implement, if they implement it at all.
7. Migration, again - Since it took so incredibly long to get to Windows 7, what is the organization's tolerance to undertake another migration? Is IT prepared to jump into it? Have you evaluated all of the facets and ramifications? What projects are waiting and will be postponed if you move to Windows 8? Do you have the resources for another migration? Will you see an ROI with yet another migration so soon? Most organizations are suffering from "migration fatigue" and don't have the energy, and ultimately lack the cumulative political will to undertake the entire process again.
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