I just came across this luncheon webcast of Michael Slaby at the Berkman Center for Internet and Society: http://cyber.law.harvard.edu/interactive/events/luncheon/2010/03/slaby
I highly recommend watching this in its entirety because the conversation is so tangible to so many different kinds of organizations and situations.
Slaby dives into his experiences on the Obama campaign team and then follows up with various discussions regarding the Obama campaign technology to Web 2.0 and how online strategy can turn into offline movement.
My personal favorite discussion was about maintaining the campaign narrative through the online channel and how web 2.0 applications were used as a tool for people to tell the story instead of web 2.0 trying to tell the story.
This was a very engaging discussion that definitely sparked my interest and brought forth many questions for me. Hopefully it will do the same for you. And if you happen to come across other webcasts that are similar in nature, please send them my way!