Once upon a time, Microsoft introduced Windows Vista, assuming Windows XP users would upgrade to the new operating system as a matter of course. We all know how that turned out.

This past October, Microsoft tried again, with the release of its newest operating system, Windows 7. This time around the new operating system is gathering kudos from users and reviewers, who praise the features and performance, and the fact that Windows 7 does not demand as much computing power as Windows Vista did. Oddly, experts also all note that Windows 7… really isn't all that different from Vista after all.

'I look at Windows 7 as new service pack for Windows Vista,' says Christopher Blake, workstation administrator, The Benchmark Group, an architectural and engineering firm. Still, he says, the new name made it easier for Benchmark to opt for the upgrade. 'In my opinion, Vista was a good operating system for the enterprise, but the problem was really psychological. People hated the word ‘Vista,' and we would have been martyrs if we'd tried to roll it out.'

Like The Benchmark Group, the majority of companies that stuck with Windows XP in the face of Vista's real or reputed problems now face an additional challenge as they plan their move to Windows 7. While upgrading from Windows Vista to Windows 7 is merely a matter of installing the new disk, an upgrade from Windows XP means reinstalling all the applications on the computer as well. 'I don't know if the intent was to reward the people who upgraded to Vista or punish the people who stayed with XP, but they did not include a user-friendly tool for migrating from Windows XP to Windows 7 -- and they knew that was what most of their customer base would be doing,' Blake says.

Still, the new features in Windows 7 make it appealing to both end users and IT staff. Most smart phones and mobile devices are recognized instantly when they are plugged in, and mobile workers can now have laptops that recognize their location and sent print jobs to the nearest printer, while the IT team gains the ability to install software remotely and handle power management more efficiently. 'Now is the right time for us to move to Windows 7, because we're seeing that we can benefit from the new technology and new features,' Blake says.

Time to switch

With Microsoft committed to security support for Windows XP (with Service Pack 3) until at least 2014, is now the right time to move to Windows 7 for your company?

Yes, if you want Windows 7's new features, if your users do a lot of mobile computing, and if you use mostly standard business applications such as QuickBooks and Microsoft Office. Also if you are buying new desktop computers, since the new machines will likely come with Windows 7 preloaded.

No, if you don't want to buy any new hardware, since moving to Windows 7 will probably require new video cards for some computers at the very least. You should also wait if your company uses large numbers of unusual or custom applications. 'Our accountant clients use a huge number of different applications, and I wouldn't even consider upgrading them right now because too many of those applications won't run on Windows 7 yet,' notes Byron Patrick, CEO of Simplified Innovations, a managed IT provider that supplies both IT services and leased equipment to small business clients.

Windows 7 does come with Windows XP Mode, which creates a virtual XP environment within a Windows 7 computer, for the purpose of running any applications that don't run on Windows 7. But managing a virtual personal computer inside of a physical personal computer may be a bit much for some users. 'Like any computer, it has to have network access set up, be connected to a printer, and to the Internet,' Patrick says. 'Expecting corporate users to handle all this may be unrealistic.'

Ready or not

To its credit, Microsoft has provided some tools this time around to help you determine both whether the hardware you have will be adequate to run Windows 7, and whether the applications you have are compatible with it yet. 'We have a compatibility wizard built into Windows 7 that will scan the hard drive and let you know if your hardware and software are Windows 7 compatible,' says Lee Sabow, marketing manager in the Windows Client Organization at Microsoft.

Or, if you want to find out before investing in the new operating system whether your applications will work with it, you can find out at Microsoft's Compatibility Center, he says.

If you do decide to go ahead, Patrick recommends copying the data off the computer to be upgraded, and then formatting its hard drive before installing Windows 7. 'On any system, when you have the opportunity to wipe the slate clean, it's great,' he says. 'And by doing it now, you avoid any anomalies that might occur because of the upgrade.'

As for installing the new operating system itself, he says, it's easier than with any previous Windows installation. 'With Windows XP, halfway through there were things we had to click to continue the process. With Windows 7, we have it loaded on a USB drive. We plug it in, set it to install, and half an hour later, it's done.'

For small group upgrades, it may make sense to reinstall applications manually, but Blake advises using an automated software deployment tool if you're upgrading more than 50 users, especially if you only have one or two IT staff members to handle the job.

'Most tools won't deploy the operating system itself, but they will deploy the applications,' he says. 'He advises choosing a tool with reporting capabilities, so you can see what upgrades have been successfully completed and which users have which software installed. 'You have to know what's going on in your environment before you can manage your environment,' he explains. The Benchmark Group uses a KBOX appliance from KACE for software deployment, he adds.

However you do it, make sure to build in enough time for testing the new operating system with your company's applications, and also for training on how to use it. 'Don't get into a situation where the upgrade will become a pain point for people,' Blake says. 'We have time, so take it slow, and do it right.'