If you go to the CD-Media section, papers, and use the word Chairman in the search field, you will find lots of previous entries and some tips.
It is too late, but for future reference some Kickoffs - such as the one in Upper Darby PA - have seminars on how to submit a Chariman's Award entry, given by previous winners.
Here is presentation given in 2008 at Kickoff - it doesn't discuss the video **(which wasn't required then) but can still be useful. I'll see if they can post this year's slides.
http://moe365.org/moeu/chairmans_awa...ation_2008.ppt
And for the past three years (and most likely again this year) there is a conference/panel discussion presented at Championships entitled "Chairman's Award Chat - Talk with Championship Chairman's Award Teams" which can be very useful.
(
http://firstd7.browndesignclients.co...eAbstracts.pdf)
**I personally think the essay and presentation to the judges are more important than the video. The essay is the first thing the judges read and you can go into more detail there. And the presentation is a make or break - you can either wow the judges or ruin all your chances face-to-face. But I don't know for sure; this is just my guess.