A new system and method have been invented to allow a sender/author/user who wishes to send e-mail or a calendar meeting document to someone and make it available to her or his assistant or manager without the need of the sender/author/user finding out who the assistant or manager is. That is, the system and method of the present invention allows the sender/author/user to choose a select number of recipients or even the role who are able to decrypt the email/attached document. Further, the new system and method provides a sender/author/user to choose which level of authority each user or userrole.