Tips for Planning a Microsoft OS Upgrade

Updated: April 30, 2009

Whether IT managers are reacting to Microsoft Corp . issuing its latest XP service-pack upgrade last May, scrambling to usher in new applications or scurrying to meet regulatory requirements, the rush for Microsoft OS upgrades is on.

If you manage your OS move carefully, your entire organization will reap the rewards. Rushing into this massive change or failing to prepare your IT staff and users properly will invite disaster.

Use the following tips from experts to ensure that your OS upgrade is successful.

Avoid a Nasty Rash

"Of the biggest challenges facing a company going through a major OS upgrade or change is the rash of incompatibility issues that will arise during and after the upgrade process," noted Dennis Powell, senior product manager with StackSafe Inc ., an infrastructure testing company in Vienna, Va. "The operating system, Microsoft or otherwise, underpins an organization's IT infrastructure, so it's almost a guarantee that some applications will not work or will behave strangely with the upgrade."

Because of the high potential for problems, Powell suggested that IT staff stand ready and do more than simply cross their fingers. "Entering an upgrade cycle blindly or by ‘patching and praying' will only result in more downtime and more disappointed users," he said. "Make certain that all shareholders have early and complete understanding of the extent and the timing of a change that is of the magnitude of a Microsoft system upgrade."

For Powell, the shareholders that should be consulted regularly during the upgrade include not only system, database and network administrators, but also application business owners, project managers, application development groups, application support groups and end users.

Powell also warned that you shouldn't forget to alert business partners, suppliers and other third parties about the big change.

Slow Down, for Goodness Sake

Many organizations run into trouble after plunging headlong into a major OS move, observed Rajesh Rajamani, project manager at Solidcore Systems Inc . in Cupertino, Calif. "Even if organizations have a good change-management process, they might face resource constraints. They often rush their teams, for example, to quickly deploy newer releases without giving them enough time to finalize implementation and testing," he said.

A mad dash can prove disastrous on many fronts, Rajamani added. "These rush jobs often short-circuit either the testing or the validation of the change, which can then result in unforeseen outages."

To avoid racing into trouble, Rajamani suggested that IT staffs convince business leaders that making a move as big as an OS upgrade deserves forethought and time. "There is often a lack of visibility into change and to complicate matters, outage triages are notoriously prone to finger-pointing. Application, database and OS upgrades are often performed by a variety of teams within the company. Over 80 percent of the time that it takes to resolve a problem is spent in trying to identify the root cause of the outage," he noted.

Consider using change-control software to mitigate fallout from the blame game that ensues when an an OS upgrade hits unavoidable bumps, Rajamani added. "Change control ensures comprehensive visibility of all change and helps ensure each change or upgrade happens as it is supposed to."

Think Twice

While slowing down is a good idea for any company pondering an upgrade, some organizations may want to revisit the idea entirely. "From a spend-management perspective, there are a few reasons related to cost reduction when deciding to leap into OS upgrade to say, Vista," said Jon Winsett, managing partner at NPI Financial in Atlanta.

Walk through payment scenarios that will include extra resources for additional processor speeds, RAM and storage solutions. Additionally, organizations may have to upgrade all or most of their existing bases of desktops and laptops.

Further, it is wise to realize costs in their entirety before signing on the dotted line. "Microsoft will really push for an enterprise agreement [EA] to help spread the costs of an upgrade out over three years. But you will also pay a premium for software assurance, support and blanket licensing. An argument can be made for an enterprise experiencing lower costs when managing internal license compliance with an EA due to the true-up feature. But overall, EA's are a luxurious way to license Microsoft products in a normal three- to five-year upgrade cycle that most enterprises find themselves in," Winsett said.

Change Is Inevitable

Although organizations with tight belts may want to do a little more research and budgeting before dashing headlong into an OS upgrade, the time for change is likely approaching. "While it might seem far too early for organizations to begin the upgrade process, the cycle, especially for large enterprises, is fairly lengthy and is best undertaken sooner rather than later," said StackSafe's Powell.

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