This is going to sound weird, but out of the half-dozen or so methods that I've tried to do this, the one that seems to work best is to reply to the meeting in your calendar and then address that reply to your boss.

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Sue Mosher, Outlook MVP
Author of Configuring Microsoft Outlook 2003
http://www.turtleflock.com/olconfig/index.htm
and Microsoft Outlook Programming - Jumpstart for
Administrators, Power Users, and Developers
http://www.outlookcode.com/jumpstart.aspx
>I want to schedule a meeting on my calendar and automatically notifiy my
> supervisor by email. I could do this in Groupwise. Can it be done in
> Outlook 2003?