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There are a few options:
1. If your boss has a licensed Tableau Desktop then he can refresh the workbook himself.
2. You place the packaged workbook on a network drive that he can access. Behind the scenes, you're manually refreshing that workbook and replacing it on a schedule. I did this at a previous job on a weekly basis for three important reports.
3. If you had Tableau Server then he wouldn't need the Reader nor Desktop as he could go to the web page and view the report, which you would have the server update using a schedule.
2. Is there a way to schedule automatic updates to a packaged workbook that is located on a network share?
It may be possible through tabcmd - which requires Server - which would probably render your question moot...