[AnthonyMouse]

This is why you do what Munich did. Step one, before you install your first Linux machine in production, require all your software to run on both systems. That also trains the users to use LibreOffice and Firefox and so on, even though they're still using Windows, and you can do one application at a time over however long it takes. No new software is permitted that won't run on Linux, even while you're still on Windows, and any existing software gets phased out.

Step two, you change out the underlying OS and people barely notice because all the applications are the same.