Henry DeSio, the Global Chair for Framework Change at Ashoka, Joins Denver Frederick

The following is a conversation between Henry DeSio, the Global Chair for Framework Change at Ashoka, and Denver Frederick, host of The Business of Giving on AM 970 The Answer in New York City. This transcript has been lightly edited for clarity.


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Denver: The presidential campaign trail–no matter what side of the aisle you may be on– can be a microcosm of changes that will eventually take hold in the broader society. For instance: rapid response to events–never letting a news cycle pass without responding to a charge– started with political campaigns, and is now embedded in the DNA of most every corporation and organization. My next guest served as the Chief Operating Officer of Obama for America in 2008, did a stint in the White House as Deputy Assistant to the President, and is now helping young people navigate the new strategic landscape driven by rapid change. He is Henry DeSio, the Global Chair for Framework Change at Ashoka. Good evening, Henry, and welcome to The Business of Giving!

Henry: Thank you, Denver. It’s a pleasure to be with you.

I see social entrepreneurs as everyday citizens who are essentially society’s corrective force. They’re the people who see the gaps in our communities and work to position their leadership, bring their talents, and bring others around those problems… or potential opportunities that can have such a great impact in the world. They are everyday citizens who apply their leadership and their talent to make the world a better place.

Denver: One of my very first interviews on The Business of Giving was with Bill Drayton, the founder of Ashoka. He is, to many, the father of social entrepreneurship. So, let’s start by having you tell our listeners about Ashoka and its work.

Henry: Ashoka is best known for defining and building the field of social entrepreneurship over the last 40 years. Some people don’t know what a social entrepreneur is, so I’ll just very quickly explain. I see social entrepreneurs as everyday citizens who are essentially society’s corrective force. They’re the people who see the gaps in our communities and work to position their leadership, bring their talents, and bring others around those problems… or potential opportunities that can have such a great impact in the world. They are everyday citizens who apply their leadership and their talent to make the world a better place.

Denver: Before we get to your current work at Ashoka, let’s start with your career in politics. You got the bug, Henry, for politics by watching the Watergate hearings. So tell us how you went from watching Sam Ervin and Howard Baker to becoming the Chief Operating Officer of the Obama for America presidential campaign.

Henry: Well, I grew up in a very rural part of California in the foothills of Sequoia National Park, so you had everything available to you – tennis, baseball, hiking, all kinds of different activities. But in the middle of the day—this is, I guess, 1974—I remember coming in from the hot sun to watch my first reality TV show, and it was the Watergate hearings. And in those days, and particularly where I lived, you had a small black-and-white TV, and the White House just seemed so far away.

And in that moment, I saw  a government and a leadership fail in action, but I also saw a good result for the country. We worked through this; we got through this challenge. But it was in that moment, two of my passions came together. One was leadership, which my dad I think drilled into me, and the other was politics– and later, the political campaign.

I think those two passions seemed to stay with me throughout my life. I was always interested in citizen candidates. I wanted to see everyday citizens break into politics, so I started working on helping everyday people get the skills to build that startup organization that could lead to real change… and could actually unseat the other person. Eventually, that flowed into politics on a national scale… and eventually to joining the Obama campaign

Self-definition: giving yourself permission to solve problems; pursue opportunities; go after the things you’re passionate about; and then delivering on those things — those are all things that are at work in our daily lives.

Denver: Well, because of the nature of politics– the speed, the urgency, the constant feedback you get from the polls, and that looming deadline of Election Day– there are some principles that you take from the campaign trail that you believe, Henry, can apply to life off the campaign trail as well. What are some of those things?

Henry: Well I look at the campaign trail even now, and I’m constantly looking at what are the lessons we can glean from our politics that we can take into real life. One is self-definition. If you’re a candidate and you can’t define yourself, you will be defined by the other person. So, a golden rule obviously is “Define thyself, lest you be defined.” The second thing is: positioning your leadership. Once you define yourself, make sure that you’re positioning yourself for the greatest impact. And on the campaign trail, you position yourself… you take a stand based on issues.  It’s the people you stand with;  it’s how you approach problems. So, people are constantly, in the back of their minds, dialing in how you’re positioning your leadership.  Does your deed match your creed?  Are you actually doing what you say? And then finally, you have to deliver on what you say you’re going to deliver on. So competence is hugely important.  Whether running for dog catcher or for President of the United States, your ability to build an organization around your ideas and to competently execute on those ideas– that’s hugely important in the success equation on the campaign trail.

These things are also at work in our lives off the campaign trail. Self-definition: giving yourself permission to solve problems;  pursue opportunities;  go after the things you’re passionate about; and then delivering on those things — those are all things that are at work in our daily lives.

When people in the lower and middle rungs of the organization are free to lead, they form fluid, shifting teams across those old boundaries of those silos to solve problems and pursue opportunities.

Denver: Yeah, whether it’s right or not, the perception is that if you can’t run your campaign, you’re not going to be able to run the country… or the county… or whatever position you’re running for.

You talked a moment ago about leadership.  Having spent time on the campaign trail, and then in the White House, you were taken by the idea of how the physics of leadership has changed. Share with us those insights.

Henry: The defining moment for me in the campaign was the shift when we went from a traditionally siloed, hierarchical organization to an organization that was open and fluid, and leadership was distributed. So let me take you back to the very earliest days. I like to describe those days of the campaign as the “days of hope and chaos.” Because, imagine  the candidate has announced mid-February; you’re opening your headquarters in maybe the first week of April. When you come into this environment, you have no signage on the walls. You have computers coming out of boxes, but you’re still getting your servers up. You have checks coming in, and you’re still opening your bank accounts. You have phone calls coming into the reception desk, but you don’t know where to send them. You have this very blank environment. You don’t even have an employee manual.

So, there are no rules, no norms, no culture, and you’re bringing this community together from scratch.  You’re building the airplane in mid-flight. And when you do that, you put people in their lanes. You hire your department heads; they build out their departments.  Suddenly you have a system that is siloed and hierarchical, and people are executing on jobs. We could pull the organization together that way.  But eventually, change was coming at us so fast as we got going… the systems are in place… you’re talking about the dynamic of the campaign… at a certain point, we had to tear down those walls in those silos. We had to allow everyone to lead because we couldn’t keep up with the pace of change.

When we did that, I made an interesting discovery. When people in the lower and middle rungs of the organization are free to lead, they form fluid, shifting teams across those old boundaries of those silos to solve problems and pursue opportunities. For example, in the old way of working: For every problem–a department.  In this new way of working:  For every problem– a different team. Between these two models of the:  “one leader at a time” model and “everyone leading” model, I discovered the physics. In the old model, one person is big; everyone else is small. In the new model, everyone steps into their bigness. In the old model, information given out is just enough to do your job.  In the new model, everyone has to have all the information to form a team and execute on those ideas. And so, as you go along, you find a whole different set of physics at work in the old game versus the new game.

Denver: Well, those lessons were certainly opportune for the role you have right now. So, tell us, how did you go from the campaign, and then serving as Deputy Assistant to the President in the White House, to where you find yourself now at Ashoka?

Henry: Well, when I left the White House, I was still really consumed by this experience of these two models, side by side. I left the White House because I was really compelled. I thought it was the moment that I wanted to write about that experience in 2008. As I was doing that, I was uncovering this different physics for new leadership. Having always tried to understand leadership and organization, I was compelled by the notion that I had a new leadership paradigm that I really wanted to bring to the world.

And as I came out of the bubble of four-and-a-half years between the campaign and the White House, I started to look at the world very differently. I started to realize that the world looked more like the Obama 2.0– that second model– than the first “one leader at a time” model. And that ultimately brought me to meet Bill Drayton, the CEO and the founder of Ashoka. And that led to a whole conversation about social entrepreneurship– how social entrepreneurs lead.  It helped me see even more clearly that the world had gone through the very same shift that I had seen in the Obama experience. I knew how to do this. I knew how to help people play in this new game, and Ashoka was moving to play in this new game.  So, there was a happy marriage there.

And that’s where I think in society we’ve had a game-changing moment. We’ve gone from a history… millennia… of jobs, people, technology– serving repetition. Think assembly line. And now we are moving into a world where everyone makes change.

Denver: Well, the game has changed indeed. How do you find people respond to this fundamental change? Is there a spectrum of responses that you have observed from people?

Henry: I think the key is we don’t really understand. We know that change is happening, and we know it’s faster, but we really don’t understand the nature of change. And so the first step is trying to really get under the hood of what’s going on in society, and how people really come to terms with the nature of change.

I’ll give you an example of how I see this. I think it’s a complete paradigm shift, not an evolutionary journey that we’re on. So, imagine you’re a football player in a locker room. You’re putting on your shoulder pads; you’re getting ready for the big game, and you’re in the final stages now. You slip those shoulder pads over your neck, and you tie them into place.  Then you take your big jersey, and you throw it on over your bulky armor. Now you’re putting on your helmet. So, this is a gladiator sport.

You prepared your whole life for this moment. You strap on your helmet.  You start charging through the tunnel; you’re going to go out to the field, and you’re going to meet your teammates. So, you get out; you blow onto the field.  You see the deep green field awash in the glow of spotlight. You’re so psyched. This is, again, the moment you’ve prepared for your whole life. And you run toward the field, and what you see is something has changed. Your pace slows.  You realize those goal posts on each side are down, and there are two nets up. You see people wearing different uniforms. They’re not wearing the same heavy gear that you’re wearing. They have flowing hair and light clothing, and they’re chasing a different football that spins out a black-and-white pattern. And in that moment, there are three choices – and this gets to your question – What do you do when the game you’ve prepared for your whole life has changed? One is: you’ll stand frozen in place. You don’t know what to do. You’ll be moved to the sidelines for good.

The second is: you might double down on what you’ve prepared for your whole life.  In this case, that means lowering your helmet and slamming into those unsuspecting players in their light clothing– which will make you dangerous and worrisome, and will also move you to the sidelines.

The third is: to see the new game–which requires new skills, working new muscles, new rules. You need a whole new playbook. You have to see the new game to recalibrate, to play in  this new game. And that’s where I think in society we’ve had a game-changing moment. We’ve gone from a history… millennia…of jobs, people, technology– serving repetition. Think assembly line. And now we are moving into a world where everyone makes change. We have all the tools available to us to do that now at our fingertips, right? We have our printing presses, our broadcast channels. And so this game of change making… which begets change,and then omni- directional change, is very different from the game of repetition–which begets efficiency and repetition.

Sometimes stepping back is an act of leadership. Sometimes knowing when to step forward is an act of leadership. Sometimes recruiting somebody who has better skills than you have in a particular situation is an act of leadership…

How do you position your leadership for the most impact? Sometimes, that’s being supportive of somebody else that needs to step up and step into their bigness. Sometimes, that’s stepping in where you know you can add something to that moment.

Denver: In this game where everybody is a changemaker then, everybody is a leader. It’s not  “one leader at a time.” Henry, in this world, do we need some followers too– people who see other people’s dreams and are dedicated to making those happen? What happens if everybody becomes a leader, and we have no followers?

Henry: So in our everyday lives, I think what’s happening is that we have shifted to:  there’s a rise in individual agency, coupled with these tools we carry with us. We’re commanding our leadership one way or the other. Sometimes stepping back is an act of leadership. Sometimes knowing when to step forward is an act of leadership. Sometimes recruiting somebody who has better skills than you have in a particular situation is an act of leadership.

So, now, it’s a matter of how you position your leadership. Going back to my campaign example: How do you position your leadership for the most impact? Sometimes, that’s being supportive of somebody else that needs to step up and step into their bigness. Sometimes, that’s stepping in when you know you can add something to that moment. But now, in the new way of leading, everyone has to be an initiator. Everyone has to see the whole picture, and then have to respond with solutions and act accordingly.

Empathy is hugely important in a world where interaction is key to success and contribution–to play on this new team of teams.

Denver: In order to be able to succeed in this new game, you need empathy. And I know that Bill Drayton, the founder of Ashoka as we mentioned before, has said:  “Empathy is the one indispensable characteristic that we all must have in the 21st century world.” But people today really seem more self-absorbed than ever, and I think a testimony of that is Facebook– where people put a picture of every meal they consume on their homepage. So, let me ask you this, how do you instill or teach empathy to people?

Henry: One of the things I think is important to understand is why empathy really matters in this new game. Because in the old game, as we were climbing our ladder, there was a question about how much empathy did you have to have before it started to work against you, right? In this new world, now we’ve moved from a world of transactions to a world of interactions. So, empathy is hugely important in a world where interaction is key to success and contribution— to play on this new team of teams. The second thing is: you have to have empathy-based ethics that work in our everyday dealings because of the pace of change; we’re all making change. Rules can’t keep up with the pace of change. That makes empathy-based ethics the cornerstone of everything that we’re doing today. How do we help people build that?

I think it’s as simple as understanding that it’s important in this new game.  Every interaction we have with a young person in our lives should go toward helping them build that empathy chip, that empathy muscle. There are very small things that you can do. It might be helping your child, who’s five or six, walk in someone else’s shoes–  to understand what they said might hurt someone else’s feelings. As you get older, it might be leaving your zip code and  your neighborhood to have  an experience in understanding what’s going on in the world outside of your own. There are so many small interventions you can do. It’s literally just a matter of awareness.

Young people have to experience developing their self-definition, acting on their self-permission, and finding problems or opportunities that can change their world. That means learning to bring others around a problem or opportunity as a team of teams in any moment, and practicing that in your teens. Learning to change your world will actually help you learn to thrive in this new environment of ongoing, disruptive change, and it will also help you change the world when you become an adult.

Denver: Along with empathy is collaboration. I know that you believe that it’s critical that young teens have a truly collaborative experience by the time they’re age 15. What does Ashoka do along these lines to make that happen?

Henry: Sure. This goes back to a really critical point. Again, I’ll just take you back to the Obama campaign. What I found in this new world of fluid, open teams of teams working across the organization–distributed leadership– was that the key to working in that environment was the ability to tear down walls and bring people together.

A lot of people thought the Obama campaign was innovative for its use of technology or social media.  But, in fact, it was this act of tearing down walls and bringing people together to form a team around a problem or opportunity in any moment– that was innovation. Now, sometimes technology took down those walls; sometimes it was the result of people coming together afterwards.  But the new requisite leadership skill of the future is the ability to tear down walls and bring two sides together.

Young people have to  experience developing their self-definition, acting on their self-permission, and finding problems or opportunities that can change their world. That means learning to bring others around a problem or opportunity as a team of teams in any moment, and practicing that in your teens. Learning to change your world will actually help you learn to thrive in this new environment of ongoing, disruptive change, and it will also help you change the world when you become an adult.

Denver: We’re going to change the pace here a little bit and go to a lightning round. We call it “Take Five.” Are you ready?

Henry: Sure.

Denver: What is today’s most under-reported story?

Henry: The changemaker effect.

Denver: What idea in philanthropy is ready for retirement?

Henry: The notion that we have to empower others.

Denver: What should we be worried about?

Henry: We should see the gap between where a society is heading in dynamic change and the frameworks that we’re using that we inherited from the old game.

Denver: Henry, what have you changed your mind about in the last 10 years, and why?

Henry: We all carry a ”one leader at a time” framework in our heads that we inherited from our youth, but this has become an “everyone leads” world, and we need to respond that way.

Denver: Name some organization, person, or thing that you have a tremendous amount of admiration for?

Henry: Bobby Kennedy.

It depends on who can recognize that we have a new social self-ideal of an innovative mind, a service heart, an entrepreneurial spirit, and a collaborative outlook. The candidates of the future have to capture that.

Denver: Will there be a viable third party by 2020?

Henry: It depends on who can recognize that we have a new social self-ideal of an innovative mind, a service heart, an entrepreneurial spirit, and a collaborative outlook. The candidates of the future have to capture that.

Denver: So, Henry, in looking to scale up your efforts to make everyone a changemaker, and recognizing the critical importance of doing this fairly early in one’s life, Ashoka has started a network of changemaker schools. Tell us about that initiative.

Henry: To help people see the new landscape, and to respond and redesign into this new landscape, we look for the few who are the curious, the courageous, and the credible– who can speak to the changes that are happening in the world. We started looking at leading educators in schools across the globe who could articulate the change and show how they are teaching to the change… and building their cultures to that change. And so we have now about 250 changemaker schools—

Denver: Oh, that’s impressive.

Henry: Yeah, just in the last three to four years, we can point to where leaders are showing the change and helping people see differently– so they can do differently.

There’s a culture and a learning framework that is based on empathy, this new co-creative teamwork helping children lead in an “everyone leads” environment, and putting changemaker skills and capacities to work for the good of all.

Denver: How do they differ from other schools in terms of the way they go about their business?

Henry: There’s a culture and a learning framework that is based on empathy, this new co-creative teamwork helping children lead in an “everyone leads” environment, and putting changemaker skills and capacities to work for the good of all. That seems to be a through line that we’ve seen in our social entrepreneur community, but we also see it active in this community of changemaker schools.

Denver: Are there some changemaking institutions that you are particularly impressed by, where they have created a climate and an ecosystem where everyone can be a changemaker?

Henry: I think we’re still very early in the awareness stage, so I think there might be some who are evolving into this. But I think it’s really hard to find organizations or communities or states or regions right now where people see the new game… and then are proactively designing into that new game. And so I think as we see an awareness tipping, I think we’re going to be able to point to that more clearly.

And I think of the new global youth apprenticeship as children mastering empathy in their childhood, pre-teens stepping into their self-definition, and adults helping preteens learn around their passion.

At all ages, we have to be able to get out of the bubble of our lives… and the routine of our lives… and step into other situations. As a child, that might be travelling to another town or another area of the town. As a teen, that might be a gap year of some sort.  But I think we have to rethink the growing up experience in a markedly different way.

Denver: Fantastic. Let me close with this, Henry. How do you see the educational system changing at its core to really create a generation of changemakers?

Henry: I think one of the challenges we have is that our institutions were built for the game of repetition, and all of our jobs and human capital and technology were built to serve repetition. We’re moving into a world of change and changemaking, which is a whole new game. It’s going to require rethinking, reimagining the youth experience–not just in our schools, but the whole growing up. And I think of the new global youth apprenticeship as children mastering empathy in their childhood, pre-teens stepping into their self-definition, and adults helping preteens learn around their passion.

And then young people moving into their teens: helping them to practice changemaking, forming a team around any problem or opportunity.  I think a fourth element would be learning outside of your zip code. At all ages, we have to be able to get out of the bubble of our lives… and the routine of our lives… and step into other situations. As a child, that might be travelling to another town or another area of the town. As a teen, that might be a gap year of some sort. But I think we have to rethink the growing up experience in a markedly different way.

Denver: Great advice. Well, Henry DeSio, the Global Chair for Framework Change at Ashoka, thanks so much for being here this evening. Tell us about your website and what people might be able to find there– about some of these transformational changes that are coming.

Henry: Sure.  Come to Ashoka.org. In fact, we have a way for people to come to our website and look at our community of social entrepreneurs who are at work changing and closing those gaps in society. We also have information about our changemaker schools and the growing up experience. And there’s lot of information I think everyone can use that can enhance their daily lives.

Denver: Well, thanks so much, Henry. It was a great pleasure having you on this show.

Henry: Thank you, Denver.

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Henry De Sio of Ashoka with Denver Frederick of the Business of Giving

The Business of Giving can be heard every Sunday evening between 6 and 7 PM Eastern on AM 970 The Answer in New York and on I Heart Radio. You can follow us at bizofgive on twitter and at facebook.com/businessofgiving.

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