All good things must come to an end, and the reign of Windows 7 as an actively supported, good-enough operating system is no exception. While it may feel like you just finished the heavy lifting of migrating your Windows XP machines to Windows 7, it turns out that Windows 7 is now more than ten years old, at least two and a half versions behind Windows 10 (depending on whether you consider Windows 8.1 to be a version of Windows all its own), and quickly approaching end of Microsoft support in January 2020.
All of this is to say that you need a plan. Except in some edge cases, it makes little sense to spend the time and money to migrate from Windows 7 to Windows 8.1, since that only buys you a couple more years of supportability. The smart money is on moving to Windows 10, buying everyone expensive Macs, or (gasp!) deploying Linux on the desktop. And while small businesses might be able to buy everyone MacBooks or move to Linux, large companies with lots of software investments in the Microsoft stack will continue running Windows, thus leaving Windows 10 as the only option.
NOTE: If you absolutely have to stay on Windows 7 for any meaningful length of time after the end of support, then you should seriously consider subscribing to extended support for Windows 7, which is available to companies of all sizes and offers security updates through January 2023 — for a fee, of course.
Of course, moving any large quantity of users from one operating system to another, especially one with as many differences, shiny new objects and moved cheese as Windows 10, is no small feat. That’s where this guide comes in. I want to help shine light on the considerations and actions you need to take in order to make your migration successful.