From what I know, the biggest blocker for the switch is that they're afraid they can't do all the stuff they're used to. While there are valid cases, it's mostly FUD.
I think you can start by introducing popular FOSS tools that are available in Windows. With LibreOffice amping up on compatibility with MS Office, now would be good time to tell people they can try it out on Windows
If you use domain-specific tools like Krita, Darktable, Kdenlive, VSCode, Android Studio, KiCAD, or whatever, you can also go thru those. They don't have to be FOSS as long as they're available on Linux (e.g. Steam, Postman, Spotify, etc).