I think you're probably best off using whiteboard features built into teleconferencing suites like Webex or Google Hangouts or whatnot, and then using a smartboard or tablet for your boss's end to control the cursor. That's probably less clunky (and more interactive from multiple sources on the collaborative side) than trying to use a smartboard's integrated software to just draw on his screen and share it via teleconferencing tools.
_________________ "Aaaah! Emotions are weird!" - Amdee "... Mirrorshades prevent the forces of normalcy from realizing that one is crazed and possibly dangerous. They are the symbol of the sun-staring visionary, the biker, the rocker, the policeman, and similar outlaws." - Bruce Sterling, preface to Mirrorshades
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