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Leadership in a Changemaker World: Lessons from the COO of Barack Obama’s Presidential Campaign

Henry De Sio ran former President Barack Obama’s campaign like a start-up

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BY Tricia V. Morente - 28 Dec 2017

Leadership in a Changemaker World: Lessons from the COO of Barack Obama’s Presidential Campaign

PHOTO CREDIT: Getty Images

As history itself would attest, there’s no doubting the fact that the team who managed U.S. President Barack Obama’s 2008 “Obama for America” Presidential Campaign ran it like a well-oiled machine.

Interestingly enough, as an exclusive Inc. Southeast Asia interview with its Chief Operating Officer Henry de Sio would reveal, the Obama campaign actually had its roots as a start-up.

When then-Senator Obama announced on February 10 that he was running for president, De Sio reveals that they didn’t start building the organization until six weeks later on April 7.

De Sio, now the Global Chair for Framework Change of Ashoka, the first and largest organization of social innovators in the world, paints us a picture of how the successful campaign started in utter chaos: “We were getting computers out of boxes and still getting final touches on our servers, we’ve got checks coming in and opening our bank accounts to receive them…We’ve got phone calls ringing into the reception desk and teams of volunteers that change everyday. People didn’t know where to send the calls to because we didn’t even know each other’s names yet. It was like coming into a blank space where there are no rules, no norms, and no cultural history.”

As with nascent start-ups, the first thing De Sio needed to figure out was “how to build an organization that would last--in that moment when you’re also still trying to figure out how to get the things you need to do in your job.”

Guided by a three-part ethos from Obama—“Build it from the bottom up; respect everyone; no drama”—and a direction to “run it like a business,” the campaign grew explosively.

“From month one to month 16, we grew from zero to 2,000 employees, and from a $7 million/month budget to $40 million/month. In the last 16 weeks of the campaign, we went from 2,000 to 6,000 employees; and budget went from $40 million/month to $100 million/month. You can imagine how much change we were swallowing up all the time and people could go rogue and anything could happen,” shares De Sio.  

Fast forward to today, and it’s safe to say the team experienced resounding success. De Sio, who later on worked with President Obama as Deputy Assistant to the President for Management and Administration, and authored the book Campaign Inc.: How Leadership and Organization Propelled Barack Obama to the White House, shares leadership principles he picked up along the way.

Listen up, start-up founders:

1. Everyone must step into their ‘bigness’

According to De Sio, the world has moved from a siloed and hierarchical world, to a world where leadership has become democratized.

“We moved from a ‘one leader at a time’ system to an ‘everyone is a leader’ system. We moved from the siloed world where we’d have jobs of repetition to a changemaker world. Everyone leads and people work across old boundaries to solve problems and pursue opportunities. If in the old game, it was ‘for every problem, a department’; in the new game, it’s ‘for every problem, a team.’ We no longer attack things based on old labels, so everyone needs to step into their bigness,” he shares.

2. When walls come down and teams come together, that’s innovation. And it is a very human thing

If anything, the Obama for America campaign stood out for its technology supremacy and use of social media. But even with their ability to leverage disruptive technology, De Sio insists that it wasn’t the newest or hottest piece of tech that made the campaign innovative. It was the ability for people to tear down walls and bring two or more sides around a problem or opportunity.

“Technology helps to tear down that wall, but it is the result of people coming together that made us successful. Innovation is a very human thing, and I like to say that the requisite theme of the future is the ability to tear down a wall and bring a team together,” he says.

3. When everyone leads, everyone makes change. And change is more explosive.

If one looks at change in relation to the old “one leader at a time” world and to the new “changemaker” world, the nature of change is different. It’s not linear, but faster, explosive and everywhere. “You need to be able to see that today’s world is fluid and dynamic and disruptive—and you need a team that can actually work into that system,” shares De Sio.

Given how change is as explosive as it is today, De Sio points out three key skills today’s entrepreneurs and leaders need to arm themselves with:

Empathy. “Because the world is interactional, and no longer transactional. Because the pace of change is so great, empathy-based ethics is now the cornerstone for how we live and work together. Rules can’t keep up with this kind of explosive change.”

Co-creative Teamwork. “This is different from the old teamwork we used to know, which was a team of functional players—people with functional skills who repeated those skills together faster and faster, harmoniously. Today, it should be teamwork where people come together and collaborate around the problem or opportunity.”

Redefinition of leadership. “What does leadership mean in an ‘everyone leads’ system? We used to think of leadership as one leader at a time, one person big and everyone small in any moment. In this new system of leadership, no one can be passive. Everyone has to step into their bigness and play and be a full contributor.