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Obama's Campaign Chief is Looking for Inspirational Pinoy Leaders

Meet Henry De Sio, Jr., former COO for the Obama campaign, who is now looking for groundbreaking, inspirational leaders through the Ashoka Foundation.
IMAGE Ashoka Foundation
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For a skeptic who’s spent time falling into Google deep dives and reading about the absolute worst of humanity, the term “changemaker” feels like buzzword straight off the assembly line of concepts made for a certain group of people to feel important. But for Henry De Sio, Jr., who served as the 2008 Chief Operating Officer of Barack Obama’s presidential campaign, the term “changemaker” has become a lens through which the rest of the world and our uncertain future can be viewed.

Back in 2008, it was during the campaign that a dramatic shift occurred, and with it, a turning point for Mr. De Sio in particular. In particular, the traditional hierarchies proved too rigid for the fast-paced world we now live in. “We’ve been in repetition for millennia, but in the last thirty or forty years, we’ve moved out of repetition and seen the rise of individual agency,” says Mr. De Sio. “We have the tools available at our fingertips, that were once only available to a few—I’ve got a printing press now, I can take a video and put it on YouTube, I can be a first responder, I can conduct a business—tools that help us act on our agency. Now we also have the democratization of leadership. That’s causing explosive change, because we’ve moved from a ‘one-leader-at-a-time’ world to an ‘everyone leads’ world.”

The “everyone leads” concept can be extremely intimidating on first glance, but it does not call for  the eradication of traditional leadership altogether; rather, it is the expansion of the concept to recognize the value of everyone’s contributions. The format we’ve been accustomed to is one that stresses the value of permission—knowing one’s place, staying well within the limits of their job description, accessing information within their pay grade, everything being on a need-to-know basis. This newer framework places a greater emphasis on trust—forming teams around capacities and abilities, keeping information free-flowing, and giving people the space to see their contribution as something of commensurate value to everyone else’s.

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It’s the idea that’s been floating around in several institutions in varying industries for decades now—that if those in an organization are made to feel like stakeholders rather than cogs in a machine, a world of accomplishment awaits. “Contrary to what people think about the Obama campaign, that we were about social media and technology, but it was literally a people thing,” says Mr. De Sio. “When people ask me what the secret was to the Obama campaign, I always say it’s not what we aspired to; it’s what we tapped. What we saw was the new DNA: an innovative mind, service heart, entrepreneurial spirit, and collaborative outlook. I see it everywhere.” 

Mr. De Sio, in a newer capacity, serves as the Global Chair for Framework Change at Ashoka, a network present in 90 countries that defines itself as ‘a global organization that identifies and invests in leading social entrepreneurs—individuals with innovative and practical ideas for solving social problems.’ Prior to Mr. De Sio’s arrival onboard the Ashoka train, the organization was already being built on the concept of “teams of teams,” which is breaking through the heirarchal silos and making for a more open, fluid, efficient, and inclusive manner of leadership. It was by observing a few Ashoka fellows that Mr. De Sio came to the fold, so to speak, and realized he had found a new home.

"Now we also have the democratization of leadership. That’s causing explosive change, because we’ve moved from a ‘one-leader-at-a-time’ world to an ‘everyone leads’ world.”

The first was Molly Barker, a recovering alcoholic who became a Ironman triathlete. In 1996, she founded Girls On The Run in Charlotte, North Carolina. She took thirteen girls and taught them to run a 5k over the course of several weeks, in an effort to break through stereotypes that attempt to cage girls from a young age. Through training alongside peers, creating a supportive community, harnessing youthful energy and passion, presenting the idea of a goal and reaching it with hard work, and giving the space for young girls to nourish their self-respect, Ms. Barker taught these girls the idea of defining oneself before society could put them in a convenient little box. Girls On The Run reached its millionth girl in 2015, and they’re still running.

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The other was Ana Bella Estevez of the Anna Bella Foundation in Spain. Ms. Estevez survived an 11-year abusive relationship, and after having escaped, raised four children on her own. The foundation gives women who have been abused concrete footing into starting a life outside of their current circumstances, by way of peer-to-peer networks, as well as working with the government to provide transitional housing and work placement for survivors. Ms. Estevez even works with media to ensure that the portrayal of domestic violence survivors is not that of weakness or violation, but of the ability to overcome adversity, start fresh, and become contributing members of society. This shows women who are in the midst of abuse that it is possible to break away, while removing existing stigmas that may hinder them from taking full advantage of any opportunities once they do.

I have been in 3 relationships in my life. The first was absolutely beautiful. The only time I was truly in love with someone. But I was unstable with my depression and my hatred for myself. It happened while I was growing up and needing to focus on myself, I was hanging out with the wrong crowd, and I needed to instead learn how to be a better person. One of the best decisions I have ever made was finally giving up and walking away. Because he deserved more. He deserved better. And I was lost. The summer after I had began a relationship with another. He came into my life when I was at rock bottom and gave me what I thought I had deserved for being so horrible in the past. Or, what I thought was horrible, anyway. He took me in just as she explained. I truly felt like a princess. But then things changed and I felt like there was no where else for me to go. No options. The ones that l loved would feel his wrath and my friends would be affected by his forcefulness, by his jealously. Abuse after abuse until my body and mind couldn't take anymore and I finally gained enough courage to leave and never return, no matter the threats. But I was tired and I was weak and I allowed myself to fall into the same situation again. Only this time, it wasn't always physical. It was screaming at the top of his lungs when he'd been found out. It was punching walls to scare me, manipulating to the point of walking over the cliff, or me waking up after having been passed out, doing things I didn't consent to. It was also, "Baby I love you I'll never do it again, I promise - stay with me" after having spent nights alone in a hospital bed thinking I was losing my baby. My power had dwindled down to absolutely nothing. I felt like I was nothing. I felt like I wasn't even a person anymore. *Continuation in the comment section... #repost #anabellafoundation #domesticviolenceneedstostop #survivor

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Our local Ashoka fellows are just as compelling: there is Girlie Lorenzo of Kythe Foundation, Inc., which provides psychosocial support for children in hospitals. Ines Fernandez founded Arugaan, a mother-led movement where mothers teach other mothers about proper breastfeeding practices as well as healthy indigenous food options. It was her solution to the further problems young children face after natural disasters left them without nutrition or access to clean water.

There is also JP Maunes of the Philippine Accessible Deaf Services, Inc. (PADS), which has successfully trained others to become capable Filipino Sign Language (FSL) translators, encouraging an atmosphere of non-discrimination and inclusivity. Mr. Maunes also started the Break The Silence project after encountering an especially high rate of sexual abuse among deaf women—as many as 70%—by someone they know. The project aims to detect and prevent abuse; they also work on the legal side, providing  lawyers with PWD sensitivity training and courtroom interpreters with FSL training.

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IMAGE Courtesy of PADS, Inc.

Ashoka Fellow JP Maunes works with Disability Advocacy groups to train FSL interpreters and campaign for inclusive services.

The list goes on, and what Mr. De Sio does with Ashoka is provide the framework in which these organizations can function at their highest capacity. Because these are organizations that target uniquely complex problems with equally singular solutions, the former framework of repetition would probably not be ideal, Ashoka comes in with aid in several forms. Ashoka, in its own annual reports. discloses that it is funded by individuals, foundations, and business entrepreneurs worldwide, and does not accept funding from government entitites. It uses that funding to sometimes lend stipend support, or to create activities that generate other manner of support necessary for Ashoka’s Fellows to get their projects off the ground.

But to be able to get to a place of action, someone first needs to present the vision of where the world is as it is, who are the brave souls making distinct moves to address newer issues, and how we can fit into those solutions. That person is Mr. De Sio, and it is the very reason why he considers himself, titles aside, a storyteller. “In a traditional campaign, it’s about telling the voter your plans and what you’re going to do. What I found to be interesting in the Obama campaign was that it was about storytelling—not just Barack Obama telling his story, but me telling my story, and others telling their stories that relate to hope and change, and investing in that, sometimes even more than in the candidate himself,” Mr. De Sio says. “We’re seeing this new DNA and we now have to accommodate it. We have to rethink everything about this new world that we’re stepping into.”

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“What we saw was the new DNA: an innovative mind, service heart, entrepreneurial spirit, and collaborative outlook. I see it everywhere.” 

He talks about his children, ages 10 and 8, and says that they aren’t on an assembly line to a standard vocation. The system as we know it has been calibrated to accommodate a way of life that no longer exists in the same pattern—go to school, get a job, start a family. But the global economy isn’t what it used to be, where a 25 year-old with a 9 to 5 desk job could eventually afford a house and provide for a family of four. The creation of job titles is consistently on the rise (who, even as far as 5 years ago, would’ve seen an Uber driver as an actual profession), and according to the World Economic Forum, 65% of the job types De Sio’s children could assume once they’re done with their studies have yet to exist. “We gave millennials the same playbook we grew up with, but they’re the pioneers in this new world. This is where I think our attention should be, in seeing how we can affect change in this new world, and in making this new world make sense.” Mr. De Sio adds, “The world is getting so big that no one can afford to stay in a small place. It’s exciting what we’re about to come into but it’s going to require that everyone play at their biggest, and that everyone step into their biggest place. There’s room for everybody.”

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