If you're a computer programmer, working with non-programmers is tough. Apparently, folks don't come much more non-programmerish than politicos. Only… it's not that they weren't programmers. They are generally mired in the past.
Early on, our hero jokes about why the programmers used post-its on a wall to schedule their work: it's not that they didn't know more sophisticated tools. But they needed to get politicos involved with prioritizing/scheduling—and those folks don't do planning, issue tracking, none of that, nope. Post-it-based schedule on a wall was longer-term thinking than they were used to. At first it seems like a throwaway anecdote illustrating the difficulty of nerds getting along with non-nerds.
But then you hear about how political campaigns have operated historically. If politicians had ever tried to gather opinions from the electorate by anything more sophisticated than a multiple-choice poll, they would have been overwhelmed with the data. They didn't really have tools to gather it, measure it, make sense of it. It's 2013, the world has figured out something about how to conduct useful surveys, but these folks are still living in the 80s. They rely on hierarchy, rely on news bubbling up through the ranks. If most voters in the nation disagree with you on the economy, you might figure that out… but you might not. Obama's software made more things measurable; not that many more. From an outsider's perspective, it still sounds like they were stumbling around kind of blind. But the campaign was getting a lot more feedback than it was used to. (Well, probably the same amount of feedback; but maybe more signal and less noise in the mix; less distorted by games of telephone.)
Who knows? Maybe in another 20 years, politicians will listen to the people.
Yeah, I know, be careful what you wish for, right?