It’s always good to feel like you have the upper hand, especially when you have the upper hand. Garrett Graff, author of The First Campaign, argues convincingly that the Democrats are ahead of the Republicans by more than a nose when it comes to the Web 2.0. Why? I couldn’t do justice to Graff’s work if I tried to recite the many reasons here – you should read the book – but it highlights one of the core difference between the two parties: some versus many.

The Democrats have made a choice to define the party in terms of a greater audience. Graff makes the point at the end the book, noting that leadership is critical as we find ourselves, as a group, poised to make a choice between the ordinary and the extraordinary.

Graff is right that we need leaders who are willing to drive the discussion of the future of America. Yes, we need it now! But, can politicians really change the game?

I recently had lunch with a senior Republican Senator who was talking about how hard it is today to be in the U.S. Senate. He talked a lot about raising money “from the same pool, over and over,” but he couldn’t avoid questions about how his schedule has changed over the past 12 years.

Does he wake up at the same time? No. Earlier. Does he have the same number of meetings per day? No. Four times as many. Does he travel home as much? No. He travels to other States to try and help colleagues keep their Senate seats. Does he have a bigger staff? No. Pretty much the same size, yet very “potent.” Spend the same amount of time on policy? What’s that? No. In all seriousness, he said no. His attention is drawn to other things. Is he trying to change any of this? No. Not at all.

I give him credit for being honest, particularly because I don’t think there is anything unique about his view. If you could poll the U.S. Senate, many would agree that things have changed regardless of party affiliation.

But, as Graff points out, sometimes one group can harness energy and force change better than the other because they have both the skill and the will to do so. If he’s right, the Democrats are poised to lead the charge to change the country.

I can’t tell from our class how many people “experienced” Howard Dean’s run for President and how many people view our conversation about his successful Internet strategy as a case study. Again, I show my age, but I remember first hand how news of the Dean campaign’s approach to Internet outreach flooded Washington circles over night.

What had they figured out that no one else figured out? And, was there any possible end to what they could do? My old boss worked for former Speaker of the House Tom Foley and was completely engrossed in Democratic politics at the federal level. He read every article he could find about the Dean campaign and told us his children were helping him to see the success for himself on the Internet. He didn’t care much about the work going on in our office. He trusted us to get it done and kept his sights on what he thought was the most important technological advance Washington had seen in years.

Was it a technological advance or did emotional intelligence prevail over cautious thinking? Years ago, when we talked about the success of the Dean campaign, we talked about the team’s ability to control the message. But, maybe it was the opposite. Maybe the success of the team lies in the fact that there were willing to take risks and allow people from outside the campaign into the campaign in a significant way. “Control,” as we think of it in politics had, for the most part, left the room.

Now, with a better understanding of how things developed behind the closed doors of the Dean campaign, I am even more impressed and encouraged by the power of the Web 2.0 and the people who see its strength. However, I am curious as to how long it will take MOST people, particularly business people, to truly embrace it.

Control plays a large role in corporate America. I had a friend who lost a job once because she sat her CEO next to a liberal member of Congress when he was a staunch Republican. Her boss told her the CEO complained about “not being able to control the conversation” and that was with just one person, albeit an important person. But, how could that same company embrace Social Media in this type of corporate culture?

I plan to spend some time this summer delving in to the corporate sites we have discussed to learn more about how they strike the right balance or if they attempt to go beyond balance in search of conversation. I still believe Social Media will distinguish the good, the bad and the ugly in years to come. And, with the Dean Team as an example, I hope to identify the enormous upside potential for those that are willing to take a deep breadth and welcome people in …