Training your technical staff on Windows 2000 involves more than sending a few technicians to a five-day course. Involve your technical support staff in the Windows 2000 deployment design phase so that they become aware of exactly what it is they'll be expected to support. You may find their input useful in designing a deployment that can be most effectively supported by the staff you have. It will be beneficial for key technical support engineers to attend some of the Microsoft training courses currently available. If your technical support staff has no experience with Windows 2000, these courses can help provide them with an overview of the new technologies introduced with Windows 2000, and what's required to support them. But this is really just a foundation from which their knowledge and expertise must grow. Consider selecting a training organization that can provide you with custom training, tailored to your organization's specific needs.
Look for a company that can offer training not only to your support engineers but also to your end users. Show candidates your Windows 2000 deployment design, and work with them to identify which technologies are covered by existing courses and which technologies may require a custom focus. As the training company designs these custom courses for your support engineers, work with them to determine not only what it takes to implement and support these technologies, but what it means to use them.