G'Day Gbrew,
You can not readily do this with Outlook - however, please
see:
http://www.cs.umd.edu/hcil/datelens/.
I urge you to watch the streaming video (link on that page) -
it's the ONLY "User Guide" you will get.
Datelens is a PDA product that offers a very cool view
into the Outlook Calendar, and for the PDA you must buy it.
Two variants of the Desktop version are FREE, though
unsupported:
An addin version that pops a button onto the Outlook
Toolbar. I have this working well - Outlook minimised
and a small Datelens Window onscreen.
A standalone version that fires up a hidden instance of
Outlook and therefore (to me) has no advantage over
the Addin (though it also works well).
Either may occasionally crash - although the latest version
does seem very stable.
Make sure that Outlook is NOT running when you install
either.