In the first part of this two-part article, I discussed the challenges many organizations that stuck with Windows XP are facing. XP is getting rather long in the tooth from a technology perspective, and while there’s rarely a compelling reason to upgrade for an upgrade’s sake, XP is struggling to support modern hardware, and slowly being abandoned by the software development community. Furthermore, Microsoft itself (after a couple of reschedules) is ending support of XP in two years. Windows XP is also no longer the computing standard, where anyone who used a mainstream PC in university or at a prior job is more likely to have used Windows 7 than XP.

So, where do we go from here?

With Windows XP nearing the end of its life, enterprises are faced with a difficult question: upgrade to Windows 7 and essentially be a release behind from day one, or make the move to Windows 8, a relatively untested commodity that also represents a dramatic change in the OS. Like most technology questions, the tools you use depend largely on your organization, although I would bias my choice toward Windows 7 rather than Windows 8.

What a difference a number makes

Many commentators have suggested that Windows 7 is what Windows Vista “should have been,” and I would tend to agree with that sentiment. Appearance and feature-wise, the two operating systems are nearly identical, yet Windows 7 has ironed out the notorious early-release kinks that plagued Windows Vista. The migration from Windows XP to Windows 7 is fairly smooth and largely beneficial: users should be familiar with the OS from first boot, and it gets your company relatively current in terms of hardware, software, and vendor support.

Windows 8, on the other hand, has two big question marks: how well will the new Metro interface work in an enterprise environment, and how will the OS perform out of the gate? Metro is a significant departure from the Start button and interface elements we’re used to, and while an optional, more traditional desktop lurks behind the Metro interface, an XP user will likely be lost on first boot. Furthermore, this release could go the way of Vista, with technical glitches plaguing the OS until the first service pack, or it could be smooth sailing like Windows 7. In any event, combining a very different user interface with questions around how well MS delivers on its promises represents quite a few unknowns.

If your organization delays upgrading until the first service pack release for Windows 8, a fairly standard and reasonable practice, you’re looking at a migration that’s awfully close to the XP end of life. I see Windows 7 as representing a perfect interim or longer-term solution. It’s a well-supported OS at this point, one that doesn’t present your users with learning a completely new user interface, while still getting your technology more current. While your users learn the nuances of the Aero interface and the additional capabilities brought by the new OS, you can comfortably wait to see how Windows 8 fares in the marketplace.

Unless your company requires Microsoft’s latest and greatest (in which case you’re likely already running Windows 7), there’s little reason to be the first aboard the Window 8 bandwagon in the enterprise space for your entire fleet of end-user computers. Where mainstream companies should be watching Windows 8 is in the tablet space. The greatest promise I see for the U.S. is the ability to deliver a “split personality” computing experience-where a finger-driven, data consumption model is presented for tablet use, and the same device can quickly deliver a desktop-centric experience when needed, all running on the same hardware and with familiar software.

Rebuilding the upgrade muscle

OS upgrades are like a muscle, and for many companies still on XP that muscle hasn’t been exercised in years. Whichever OS ends up being in your company’s future, start exercising the “upgrade muscle” immediately. Upgrading small groups of users makes a great deal of sense, and I’ve seen several corporate IT departments ask for volunteers to upgrade to a test image of a new OS. This gets you a volunteer pool that’s likely interested in technology and more willing to put up with any growing pains the new OS presents, especially since they volunteered for the technology in the first place. If you can get a good cross section of users in this pool, you can cover applications and usage scenarios you may have otherwise missed, and also build some good PR for IT since you’re providing what this user pool would consider a perk. There are myriad other ways to identify small groups of willing candidates for an OS upgrade to work out all the kinks before rolling out massive waves of upgrades that are beyond the scope of this article, but in all cases, be aware that an OS migration may be technically trivial, but is a high-stakes challenge for IT since an imperfect OS may block access to critical computing functions on a large scale.

While I’d recommend waiting for Windows 8, making a move to 7 sooner rather than later is looking like an increasingly safe bet to get users, application, and technology support current after a decade-long run with Windows XP.