While a few early adopters already have installed the newest versions of Microsoft's Windows operating system, the vast majority of enterprises today are just getting started. As they evaluate the enormity of the upgrade task, many enterprises are asking a simple question: should I bring in some outsourcing assistance?Unfortunately, the answer to this question is not so simple. The process of operating system migration in a large enterprise is often long and arduous, and there are a variety of approaches to it. Before the enterprise can decide whether it needs outsourcing help, it must decide on its migration strategy; this strategy, in turn, will help determine whether outside services are required.To develop an\u00a0operating system\u00a0migration strategy, the enterprise and its IT organization must ask several key questions:*How quickly must the migration be achieved?Many enterprises prefer a slow upgrade, migrating individual departments or groups of users one at a time. However, many enterprise applications today work better if all users are on a common operating system, so it may be necessary to do a "flash cut" migration that brings the majority of users up on the new\u00a0operating system\u00a0at the same time.*What will be the process for the migration?In order to complete the upgrade, the IT organization must develop a structured process for imaging and backing up the data on each desktop, customizing the operating system configuration appropriately for the user, and automating the deployment of the operating system\u00a0software.*How many more migrations will the enterprise be doing in the future?This question is key to the outsourcing decision, yet it is often overlooked in the heat of the immediate migration problem. Microsoft is already developing several successors to the new Windows XP - enterprises must ask themselves how quickly they will want to deploy the next generation of operating systems.The question of migration speed is important in evaluating the need for third-party assistance. If the upgrade will take place slowly, on a workgroup-by-workgroup basis, the task can often be divided up among the internal IT staff without delaying other projects. Migration automation tools such as those made by Marimba, LANDesk and PowerQuest can help lighten the load. However, if a flash cut is required, then the enterprise will likely need both automation tools and professional services, if only to prevent the internal IT staff from being overwhelmed.The "process" question may give the enterprise some hints as to what type of outsourcing help it needs. If the migration process already has been established and tested internally, then the enterprise may only need some additional IT bodies to help keep systems up and running while other IT staffers are working on the migration. However, if the enterprise does not have a structured migration process, then it may need the help of an outsourcing company with expertise on migration - a systems integrator, perhaps, or the professional services arm of one of the migration automation tool vendors.The most important question, however, is frequency of migration. Microsoft has promised to deliver a new version of Windows at least once every three to four years. With this in mind, it no longer makes sense to view migration as a single "project" that requires outsourcing help for a short, limited time.Enterprises must establish a structure for handling migration that is architected for coming versions of the operating system as well as XP. With this in mind, enterprises that choose to outsource should take care to select a provider that can build and maintain processes for migration over time. This consideration tends to favor the migration automation tool vendors, which usually offer professional services and obviously have a vested interest in developing best practices for migration over time.