I know that I can set the option to request for a Read Receipt for all messages or to set it on a per-message basis. However, I only want to set it when sending to certain people.

For instance, I only want to request a Read Receipt when sending to my boss, the HR department and some project managers.

Is there a way to have Outlook automatically ask for a Read Receipt if an email is sent to a specific email address rather than needing to set this manually?