Hi Jeff,
The top level of the Office 2003 diagramming tool
only allows one 'top level' entry. You could turn
off the autolayout choices, create two assistants or subordinates,
use no line/no fill on the top level box through
Format Autoshape and manipulate the location of the
two assistant/subordinate connection lines by dragging
but it's probably going to be like a poorly built house
of cards.
If you have complex org charts you may want to look
at using MS Office Visio,
http://microsoft.com/office/visio ,
or Orgcharts Plus (
http://orgplus.com), among others.
These can create the chart from either your typing/placement
or from a database/spreadsheet file.
You can also download and use the older MS Office org chart
tool (the older version of Orgplus) from the MS Office 2003
Resource Kit downloads
http://microsoft.com/office/ork/2003
as a way to achieve the shared top level result.
You can also use a blank Drawing Canvas (Insert=>Picture=>New Drawing)
in Word and place shapes and connectors that you wish to
use manually.
=========
I am using Office 2003 and have setup a complex org chart in a Word document.
Now I need to go back and add a new supervisor at the top of the chart. How
can I add a supervisor? I can only get the program to add subordinates.
Thanks.>>
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Let us know if this helped you,
Bob Buckland ?

MS Office System Products MVP
*Courtesy is not expensive and can pay big dividends*
Office 2003 Editions explained
http://www.microsoft.com/uk/office/editions.mspx