Dr. Scott helped us find a problem and its solution. She was having trouble sending things like faculty meeting agendas to the faculty. It turns out that if you try to send a document from within Microsoft Word (and presumably Excel or Powerpoint) by clicking on "File", "Send", "Email", it will fail to actually send the message unless you have already logged into Microsoft Outlook/Google Apps Sync. If Word launches Outlook for you, it will fail to start up the Google Apps Sync program.
If you want to send Microsoft Office files to others from within those programs, be sure you have already started Outlook/Google Apps Sync on your computer.