If you're a CIO, you've been down this road before. You experienced the growing pains in making a transition from Windows NT 4.0 to Windows 2000, and then from Windows 2000 to Windows XP. So you know what it takes to shift an enterprise to a new operating system, whether on the desktop or the back end.

Yet, even with all of your experience, Windows Vista represents a monumental change for an organization. You have to plan PC purchase cycles and custom application upgrades carefully. Managers have to make sure the team is prepared for the migration on every level, from testing and implementation to help desk and training. And when all is said and done, as your company weathers the inevitable storm of early implementation, you have to justify the business value of the change and its associated costs.

Just another day at the office.

The new operating system offers the enterprise many advantages over Windows XP, including better image management, far greater desktop control, improved security and granular control of devices such as USB drives. However, it also presents users with a vastly different user experience, causing them to leave the familiar for the new and unknown. Before you head down the implementation path, learn from the experiences of early adopters. Here are the steps in a Vista migration to tackle before you add dates to a rollout schedule.

For guidance in deciding if you should be an early adopter or whether your company should wait for the initial bugs to be worked out, see When Is the Right Time to Move to Vista?

Planning for Change
Like any large-scale software migration project, Vista requires planning. Start by taking a long look at your current environment, says Shanen Boettcher, general manager of Windows client product management at Microsoft. Microsoft has created a whole set of tools, including the Application Compatibility Toolkit and Business Desktop Deployment 2007 (BDD) to help you in this regard. "Companies need to...assess the current environment and get their arms around devices and applications they have in their company. One of the things we did differently with Windows Vista is that we have a set of tools that target these tasks," Boettcher says. The Application Compatibility Toolkit, he says, gives technicians a soup-to-nuts view of the compatibility state of your environment, while the BDD provides a complete cookbook for implementing Vista in the enterprise.

Al Gillen, an analyst at IDC who covers operating systems, says the Vista implementation should have all of the familiar OS-implementation touchstones. "Typically, when a new OS comes along, the enterprise looks at the product and goes through a several-step process including evaluation, compatibility testing and implementation in a select group, usually in the IT department. You get some experience with it and you see how it fits," Gillen says.