Sometimes, some of the Chromebooks will prompt with a message asking for the user to enter an old password. It is safe to select "Forgot your old password?" and then click "Proceed Anyway". The Chromebook will say all local data will be lost, but it will not remove any data from that specific user's account. This has happened several times before and this method is the easiest way to bypass that message so the user can continue using their Chromebook.