Bob has been dubbed the family tech support guy and he has to upgrade all of his family member's computers. Leo says that Microsoft is going to soon force all Windows 7 and above users to upgrade to Windows 10. Bob has effectively done that with his family, pushing them to upgrade to the latest versions of Windows 7 and Windows 8 to prepare for it.
Leo says that there is a tool called the GWX Control Panel which is one user's response to prevent the forced upgrade until they're ready. It disables the upgrade to Windows 10 utility.
But in the long run, it's to everyone's advantage to upgrade to Windows 10, especially for Security. One thing Bob can do is run the Windows 10 compatibility checker beforehand. But mostly, tell everyone that upgrading is for their own good.