From Startup to the White House: 3 Key Campaign Trail Lessons for Entrepreneurs

President Barack Obama's 2008 campaign chief shares what made the operation a resounding success.

learn more about Henry De Sio

By Henry De Sio


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Everything I know about the physics of winning and success I learned from the campaign trail.

There is always a winner and a loser. It's a highly competitive environment, and with every election season, a new crop of startups emerge. In that sense, the campaign trail is an entrepreneurial showcase, a laboratory for understanding the principles that separate the successful from the aspiring.

My last campaign was a scrappy startup that approached the scale of a Fortune 1000 company. While I have left the business of winning behind for the world of entrepreneurship, there are enduring lessons from my experience as the 2008 chief operating officer at Obama for America that continue to serve me off the campaign trail. Here are a few:

1. Claim your frame.

The first job of any campaign is to define the candidate -- yours and theirs. This is the basis for the endless messaging battles that unfold on television, in print, online and in person during public appearances and debates.

Related: 5 Secrets to Crafting the Perfect Startup Story

But claiming your frame is equally important off the campaign trail. That's because we, too, are defined by others. We are defined by our actions, our transactions, our interactions -- even our inaction. It is important then to overcome the forces that make us small.

Define thyself lest you be defined.

This was my golden rule on the campaign trail and it is the true north on my leadership compass. The frame around you can box you in or set you free to do powerful things. That's why claiming your frame is the first step to stepping into your bigness.

I tell candidates and entrepreneurs alike to start by creating a personal bumper sticker. Say who you are in seven words or less. But make it authentic -- your bumper sticker should be an ethos, and not a slogan.

2. Position your leadership.

Leadership is a position game. As a candidate, who you stand with and the issues you champion are part of that calculation. But actively managing one's leadership is a consideration off the campaign trail too.

CEOs must continually calibrate their leadership as their organization matures or the mission evolves in the marketplace. Entrepreneurs must also actively reposition their leadership in the face of the shifting strategic landscape they navigate.

I skate to where the puck is going to be; not where it has been. -- Hockey legend Wayne Gretsky

During our 2008 run, my role never changed. Where I positioned my leadership did.

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In the messy startup period, I was the quarterback bringing order to the chaos around me and helping our incoming staff command the new game. As the competition intensified and speed became the imperative, I knew to step aside to let others lead. Much like the coach positioned alongside the field of play, I could provide direct input to my teams but I was now reliant on the performance of others for our success.

In the final months, as we mushroomed in size, my management moved to a higher, more strategic level. From the sky box, I could view the larger picture more clearly and offer counsel from above, but I was now overseeing a sprawling system more than managing a set of activities or functions.

3. Be a team maker.

Assembling and running the organization that moves ideas forward is as important as the ideas themselves. That's why I coach candidates to take their role as the CEO seriously. Constructing a winning campaign is ultimately as much a team-building process as it is a vote-getting operation.

When walls come down between two sides that don't normally interact, innovation happens.

A key management lesson from my 2008 experience was the importance of actively tearing down barriers that inhibit cross-cutting teamwork. This made it possible for people in our organization to form fluid, shifting and evolving teams across the system to solve problems and seize opportunities -- teams of teams. The true value add in any moment was when a new team was introduced to an existing one to meet the ever-changing nature of problems and opportunities.

The ability to tear down walls and bring teams together is a fundamental leadership skill. Combined with the qualities of the change maker -- innovative mind, service heart, entrepreneurial spirit, collaborative outlook -- this is the new premium.

Henry De Sio

Author, Public Speaker

Henry F. De Sio, Jr. is the author of the new book Campaign Inc.: How Leadership and Organization Propelled Barack Obama to the White House from University of Iowa Press. He was the 2008 chief operating officer at Obama for America and was appointed deputy assistant to President Barack Obama during his first term in office. A resident of Alexandria, Va., De Sio currently promotes the principles of personal and organizational leadership through his writings and public speaking engagements.

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