My Passport will not automatically back up files that I manually transferred. .Help Please!

Some one told me that I could transfer files to My Passport. . .however these files will not automatically back up to the external hard drive.  This is very new to me. . .I need to find out how do I delete these files (empty hard drive) and start over?  Can I back up by file so I can look at the list and see what is backed up?  Thank you so much for help.

If you want to automatically backup your files, you can use smartwear, check the link below to use it. To delete the files just right click and select the option to delete.