Plan and document everything; it makes everyone less anxious. Write both rollout and rollback plans. Give timelines with plenty of time. Include a pilot phase. Select one or two keen users to trial the desktop migration on first. Provide primer training for these people. Solicit feedback from them. Pass this on to management. Discuss this feedback with the next target-group users to assuage any fears. Plan for granular phased migration; rather than change the users' whole desktop, change some of the main applications to products that run on both Windows and Linux, ie, keep their Windows desktop intact, but shift them to Mozilla (Web, e-mail) first, then three months later, to OpenOffice.org then three months later, when there have been no insurmountable complaints, switch the underlying desktop to Linux, ensuring that the icons are all in the same place as with Windows.
As with any change which directly impacts end users, there is resistance. Here are a few coping strategies which may help ameliorate this resistance. If an inter-departmental billing system operates, offer the department/group a yearly cost discount once they move to Linux. Offer users training and “certification” on this new platform. (Users love such accreditation.) Determine how much money you would save per desktop in the first year post-migration, and offer half of it to each and every user involved. “If you agree to an upgrade, we will give you a $500 bonus” or “Once your system has been upgraded, you will get two days off as a holiday for your help in this exercise”.