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.\n\nYet, 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. \nJust another day at the office. \nThe 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?\n\nPlanning for Change\nLike 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.\nAl 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. \nTony Thomas, senior network engineer and product manager at Numara Software in Tampa, Fla., breaks it down even more simply. According to Thomas, any plan should include pre-migration planning, facilitation during migration and finally, post-migration assessment. "The pre-migration phase is the most pivotal aspect," he says, "because it will determine the success of your facilitation phase, and even the post-migration phase as far as customer satisfaction is concerned." Thomas estimates that manual pre-migration due diligence can take a few months, depending on the size of your organization. However, he says, automation tools that can find and correlate data for you can cut the pre-migration phase in half. \nThe facilitation phase is the most cumbersome to predict, according to Thomas. It helps if you can identify the computers in-house and which ones are remote, so you can schedule the latter to be present during migration. Another thing that can affect this cycle is the amount of work necessary to remediate issues discovered during the pre-migration phase, such as incompatibility with mission-critical software or internal hardware, he says. Thomas estimates one to two weeks to complete this phase.\nThe post-migration phase is the easiest, according to Thomas, because you have the ability to catch all the reported issues and begin to reconcile them. "It usually takes a couple of weeks to work out all the kinks and handling the spike in calls," he says. Count on a six-month monitoring period to judge the success of your migration and to determine ROI for the entire migration process.\n\nIs Your Hardware Ready?\nWindows Vista has some heavy-duty hardware requirements, so one primary to-do item is to assess your current hardware inventory. Jay Lendl, VP of the Microsoft Practice at Fujitsu Consulting of Edison, N.J., a company that is working with organizations to make the transition to Vista, suggests several ways to tackle the hardware issue. You could start by assessing the current hardware and begin planning the upgrade cycle based on your hardware refresh plan, whatever that is; then, says Lendl, move desktops to Vista only on the planned upgrade cycle. In that approach, you assume that no existing hardware is compatible.\nThe second approach for IT managers is to examine the current hardware inventory and make decisions device by device, according to Lendl. "If an organization has bought hardware in the past six months, it probably is compatible," he says.\nThe third approach is to retrofit existing hardware to make it compatible by installing additional memory and a better video card. Lendl says not many large organizations are considering this method; it's not very cost-effective when you factor the cost of the parts along with tying up IT staff (or consultants) to handle the upgrades.\nSome CIOs have taken the long view and built a refresh plan to accommodate Vista. Cameron Cosgrove, VP-CIO of the Life Division at Pacific Life Insurance, based in Newport Beach, Calif., began planning for Vista long ago. "It was delayed, after all. You knew, as a senior leader in IT, this operating system was coming," Cosgrove says.\nNew operating systems do more things and require more hardware. With that in mind, Cosgrove says, "I looked at my inventory a year or so ago and recognized that I had choices to make about timing on my refresh cycle." He told the company's business units that he was going to defer refreshing for a couple of cycles. "When we deploy Vista, we will time the refresh of our hardware with deployment of the operating system," he says.\nBut not all senior IT executives are taking this approach. Richard Casselberry, director of IT at Enterasys Networks in Andover, Mass., thinks his existing hardware will work fineso long as he stays away from graphics-intensive operations, such as Vista's Aero interface. "Our requirement is we have to use existing hardware. We're currently on a five-year rotation," Casselberry says. He recommends kicking up the memory to 1GB if you intend to keep older inventory.\n\nChecking Application Compatibility\nIn addition to getting the hardware in order, you need to test every application in your desktop catalog for compatibility: off-the-shelf programs, custom applications and utilities. For a large organization, this can be a huge undertaking.\nCosgrove's organization had more than 350 applications to test. He describes moving to a new OS much like moving to a new house: You find a lot of stuff you no longer need. Take the opportunity to assess your application inventory, he suggests.\nWhen customers approach Lendl's company, application compatibility is usually their biggest concern. "There are a variety of potential issues. Probably the biggest takeaway is that the cost of making applications Vista-compatible can vary from a small change to a sizeable change, as in the hundreds of thousands of dollars." He recommends using tools (like the aforementioned Microsoft Application Compatibility Toolkit) to understand the level of compatibility issues and then prioritize them.\nIt's often the little things that get you, points out Casselberry. Most of his organization's custom applications worked fine under Vista, but one Windows XP legacy application didn't work in Vista. He worked around this problem by running the application in Vista's legacy mode. \nAt AMD, the Sunnyvale, Calif., chipmaker, most of the company's applications are Web-based so they weren't affected by Vista, according to Jerry Meeker, senior manager of IT strategy and architecture. However, for some problems, Meeker also had to find workarounds. For example, AMD is an SAP shop, and SAP does not yet support Internet Explorer 7. "There are a couple of instances where an SAP script developed for Internet Explorer does not work in IE7, so we have a workaround for those scenarios," explains Meeker. If Vista users encounter a known compatibility problem, they launch a browser window and sign onto a secondary server running Office 2003 and Internet Explorer 6, where they can perform that function in the legacy environment. Meeker sees this as an early-adopter problem, one that will go away as software companies upgrade products to make them Vista-compatible.\nWhen it needs to work around problems, Pacific Life has been using "shims," small pieces of code that identify the current OS as though it's another version. For instance, when an application loads, it may check for operating system compatibility; if it does not get the expected answer for "which OS are you?" the software chokes. "So we put in a shim to tell it that we are running an acceptable version of Windows," says Cosgrove. The idea, he says, is to keep the application moving forward; don't get stuck on one line of code.\n\nPreparing the Help Desk and Training\nAny time you make a major infrastructure change such as a migration to Vista, you need to get the help desk and training resources in order prior to launch. The training and help desk departments will experience pressure (and overwork) until employees get comfortable with the new operating system. \nNumara Software's Thomas says it's important to get your help desk and training staff up to speed on Vista long before you begin the implementation cycle. "Run people who are supporting Vista through an overview or 'boot camp' type class, to educate them on what to expect. ...Long before they start supporting the migration, support pros should be using it on a day-to-day basis from a training perspective," he recommends. As an added bonus, by having support staff playing with the OS early in the process, Thomas says, they act as testers. They'll be the first to encounter the issues the end users will encounter when the migration begins in earnest.\nCosgrove's company took advantage of free training resources available from Microsoft, called the Enterprise Learning Foundation, which he feels offered an immense benefit. "They have put together Web-based training, and you can redeploy it in your environment with your e-learning system. We have an in-house training department grabbing bits and pieces that apply to us, and not doing any new work, other than wrapping it in our company message," Cosgrove says.\nAMD outsources its Windows help desk support to India, and Meeker anticipates this will present more of a challenge. But the in-house support resources are working in Vista already. "Our intention is to have help desk support in place by the end of Q2. We've done quite a bit of work on that. Our initial step in that direction is that the desktop support team have all upgraded to Vista so they are actually running Vista themselves. And by running it yourself, you develop skills to support end users," Meeker says.\n\nRollout Strategies\nThe consensus on rollout strategies is to take your time. Make sure everything worksstarting in IT, then rolling out to power users, then moving one department at a time. Thomas recommends starting with a single machine. "First and foremost, we have been recommending that companies run a pilot. Find out what software is out there. Create a donor machine, run a QA test and record what you find," he says.\nAs an early adopter, Pacific Life has moved beyond the initial testing phase and has already begun piloting Vista to select power users and departments. Cosgrove is deliberately going slowly. "My deployment process is...we're going department by department and doing pilots to give end users experience. We're learning from their experience, how they are trying to use [Vista] and what we need to tweak in the actual rollout."\nAs Pacific Life rolls out Vista in each department, it has users sign off throughout the stages of the pilot. That involves each user in the changeover and gets buy-in. Cosgrove admits this has slowed him down, but he believes it has created a much better user experience. He hopes to be fully deployed by summertime.\nHowever you plan to make the move, you have to start somewhere. Use the deployment as an opportunity to take stock of your hardware and application inventory. Take a deliberate approach, and make sure your training and help desk resources are in placeand then go for it. You've been through this before. It won't be an easy transition, but if you plan ahead, you'll be ready to brave the eventual change.\n\nMore Help: Microsoft Vista Migration Resources \nMicrosoft has a variety of resources available for enterprises to help assist in the migration to Windows Vista, including:\n\n\nApplication Compatibility Tools\n\nMicrosoft Solution Accelerator for Business Desktop Deployment 2007\n\nEnterprise Learning Framework Home\nRon Miller has been a freelance technology writer since 1988. He writes regularly for publications such as eWeek, EContent, CMP Tech Web, Business Week Small Biz, and Federal Computer Week. In addition, he has developed documentation, online help and training for a variety of companies.