The Changemaker Playbook: Making Change Global With The Hon. Henry F. De Sio, Jr.

Known as the global ambassador for changemakersthe Honorable Henry De Sio, Jr. is a leadership advisor, campaign strategistand keynote speaker who was the 2008 Chief Operating Officer (COO) of Barack Obama’s presidential campaign. Serving as Deputy Assistant to the President in the Obama White House, he became intimately acquainted with a new emerging pattern of societal change. On today’s show, he joins Dr. Diane Hamilton to share how he has since followed his campaign-driven passion for hope and change to make changemaking a global phenomenon. He also talks about his workservant leadershipand what inspired him to write the Changemaker Playbook. 

TTL 815 Hon. Henry F. De Sio, Jr. | Making Change Global


I’m glad you joined us because we have the Honorable Henry De Sio here. He is a changemaker. He wrote the Changemaker Playbook. He also served as the Chief Operating Officer of the Barack Obama presidential campaign, and then served as the Deputy Assistant to the President at the Obama White House. This is going to be fascinating. 

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The Changemaker Playbook: Making Change Global With The Hon. Henry F. De Sio, Jr. 

I am here with Henry De Sio who is known as the global ambassador for changemakers. He’s a leadership advisor, campaign strategist, and keynote speaker. He served as the executive of both startups and large complex organizations. As the 2008 Chief Operating Officer of Barack Obama’s presidential campaign and then serving as Deputy Assistant to the President in Obama White House, he came to be intimately acquainted with a new emerging pattern of societal change. He is a New York Times bestseller. Changemaker Playbook: The New Physics of Leadership in a World of Explosive Change is the name of his latest book and I’m excited to have him here. Welcome. 

Thank you for having me. 

I’m excited to talk to you about your work and all the things you’ve done. I know you’re the Honorable Henry. I want to know about that and I want to know more about your background before we get into your book. 

I grew up in a small town in California, in the foothills near Sequoia National Park. Having this journey that led me to the White House is always exciting to tell. The Honorable title is essentially the title that we receive, in my case, for serving as senior staff in the White House. If you’re an assistant or deputy assistant to the president, it’s an honor that’s bestowed on you by the secretary of state. That would have been by Hillary Clinton. 

That’s quite an honor. To get to this level, you must have an interesting backstory. I’m curious, did you ever think you’d be working with a presidential campaign or in the White House? 

I probably should clarify that. The secretary of state signed off on our commission along with the president of the United States. At the end of that 2008 wild campaign, I had two signatures from the two rival candidates on my commission. 

I’m curious if you even expected to end up in the White House or working with presidential campaigns when you were younger? 

In my small town, we had three channels on my television set. White House would come on our television set every night. I always remember seeing the White House whatever I was doing or games I was playing. That would come on and it seemed like such a faraway world for me. I do remember thinking, “Someday, I’m going to be there. I’m going to be in that place.” I had that dream or that seeding of an idea from a young age, but my path was not toward politics in the way you might think.  

TTL 815 Hon. Henry F. De Sio, Jr. | Making Change Global
Making Change Global: The game has changed from repetition to everyone leading in every moment. This means that change is happening, not linear and faster, but explosive and omnidirectional.


I was a community organizer for fifteen years after I came out of college in states like Texas, Oklahoma, and Missouri. I couldn’t have been further from the White House. In 2000, I made a pivot toward politics and running campaigns. I went to the Kennedy School at Harvard and I participated in a mid-career master’s program. I came out on that path of running political campaigns. At some point, I saw myself heading in that direction, but it was never an aspiration. It was something that I felt I was being pulled toward. 

It’s probably taught you many lessons and it’s continuing to teach you lessons as we’re looking at what’s going on in politics. I don’t even cover politics on this show. Your book is more about leadership and that’s why this is so important. Whether I’ve had people on from baseball or football or people who have given TED Talks and different things, what we’ve learned applies to leadership in many ways. You say everyone has the potential to lead in every aspect of life and I totally understand what you mean by that. When you were writing this book, was this meant to appeal to people who are interested in politics since it’s your background or just anybody who wants to be in leadership? Who’s your target audience for this? 

It was motivated by an experience I had as a manager. Politics is the backdrop. I was a manager of the Obama campaign in 2007 and 2008, and then in the White House, but the lessons on leadership were management lessons. With the book, I don’t have a political point at all. Even the first book I wrote was about the lessons from the campaign trail. The second book is about once you’ve got these lessons. I was just curious about the new physics of leadership in the world of explosive change. Where can I go to find the people who show these lessons? I was working with the world’s leading changemakers in business, media, education, government, all across the spectrum of society. It’s easy to put this book in a political box. It was meant as more of a leadership, even a business book, but also there are lessons for parenting and education. It runs the gamut. 

I can see that there are many aspects to it. You said there are all the people who have shown you certain lessons. You’ve got to probably have learned a lot of lessons from Obama himself. Let’s start there. What did you learn in terms of leadership from what you saw that he did? 

If I stick to organizational lessons, I think about those early days of the campaign. You can imagine, he announced for president and six weeks later, we were opening the doors to headquarters for the first time. He announced without an organization. We took the eleventh floor of the Chicago Downtown high-rise building. We couldn’t fill it with the 100 staff that were spilling out of the elevators into this space. When we come into this space, just imagine there’s nothing on the walls. You have computers being ripped out of boxes, but we’re still putting those finishing touches on the servers and trying to get our servers up. We’ve got checks coming in the mail. We’re still opening up bank accounts to receive them. We’ve got calls coming into our reception desk with volunteers who don’t know where to send these calls because we don’t know each other’s names yet.  

You grew up in this environment of hoping chaos, I call it at the time but also, we don’t know each other’s names. We don’t have an employee management manual. We don’t have any cultural history together. To pull this sort of Wild West environment together, there were three core principles that he laid out for staff that served us through all of the changes of the campaign and frankly, as we went into the White House as well. Those three principles are one, build it from the bottom-up. The second is respect for everyone, and the third more famous one, no drama. For those of us in campaign management, it was win it like a business.  

[bctt tweet=”You have to be in touch with your own change and how your change affects others. ” via=”no”]

You have the core tenets of how we grew up as an organization. Build it from the bottom up would later fuel this notion toward everyone is a leader inside the organization. Everyone is leading in every moment. Respect to everyone brings a culture of empathy and checking your agenda at the door. It’s the same with no drama. No drama means we’re focused on the work at hand. Everybody rolls up their sleeves. As we started to grow as an organization into all the changes we went through from this mom-and-pop shop to scaling to the dimensions of Walmart in 21 months, we had that as our cultural basis. Also, we hired people with that kind of mindset and those kinds of skillsets instead of the normal expertise that you might hire into a functionally based organization. 

That’s interesting because I wrote my dissertation on emotional intelligence and you talked about empathy. Empathy is such a big part of that. As you’re talking about no drama, checking it at the door, and all that, politics is a tough thing for people if they’re passionate about it. How do you get those kinds of people to not have drama? Those are the passionate people showing up to do this. 

It’s a great point. In a campaign, you often will find that there’s a win at all cost outlook. What happens is you have an organization that can have a lot of rogue behavior. People playing by their own rules to get their own way. In those early days, he wasn’t the day-to-day manager of this organization. He left that to folks like David Plouffe and others like us, but he did show that he was asserting his CEOness from the beginning. Setting that cultural norm and boundaries right away was important. There’s a big organizational shift during the life of our campaign that is important to understand.  

When you’re building that airplane in mid-flight, you get people into their functional jobs right away. You put a team on the fuselage, on the wheels, the cockpit and so forth. What happened is that we got some normalcy and we got caught up to the crush of demand on our organization in those early days. What started to happen was as we went further into the campaign in the first year, we started to see that the pace of change was moving faster than solutions. That one leader at a time system that we all know, hierarchical, execute your skills inside a siloed system faster repetitively, that started to not serve us well.  

As the pace of change was getting faster, we had to open up the organization and allow everyone to step into their bigness. God created two different models side by side over those 21 months. The early days of one leader at a time to later everyone leading in every moment. To your point, if you have everyone leading in every moment, you have to make sure that everyone is using their leadership responsibly. This isn’t that we went flat as an organization or anything like that, but we were relying on people to be assertive in their roles. Not passive, which is what that one leader at a time system encourages. 

I’ve had many people on the show like chefs from the White House. Martin has been on. Steve Forbes has been on. He ran for president. Yang ran for president. All these people have been on the show. I’m thinking of their roles. I’ve seen Michelle Obama speak. Everybody leads in these unique ways and you’re giving a playbook for how to be a changemaker. In all the business courses I teach, it’s hard to have a one-size-fits-all approach. Are you taking different stories so you can say, “This part will work for me and that part will work for others?” People can mold it around their own personalities. Do you think that there’s a one-size-fits-all approach? 

The challenge is that we’ve had a one-size-fits-all approach for generations now. If you think about the world of repetition, from the early farm of the George Washington days to the craft of Ben Franklin’s days to the entrepreneur of Abraham Lincoln’s days, which is you get an idea, you copy, and it will make you rich. You’ve got the assembly line of Henry Ford, and then the days of Mad Men, the 1950s construction first, which helped us squeeze that last bit of efficiency in repetition out of each organization. We’ve had this shift in society now. That mirrored what I saw on the campaign. Moving from one leader at a time, that type of lane system, get that skill and take that skill inside four walls for life into this world now where we live in a world of explosive change. We are not in lanes anymore. We have all the tools at our fingertips to allow us to lead in every aspect of life now.  

That playbook of the old game doesn’t work anymore. We’re still playing with that old playbook that’s been handed to us for generations. The reality is now that we have moved, the physics of leadership has completely flipped. What I saw in my campaign experience, if you think about this, the first system is one person is big and everyone else is small at any momentIn the second system, everyone’s a leader, everyone’s leading at every moment. The first system is teams arranged by functional jobs. The second system is teams pulled across those old silos based on your talents and possibilities, and not necessarily your job title and responsibilities. For example, in the old system, for every problem, the department, and the new system, for every challenge or opportunity, a team.  

In the old system, information doled out on a need-to-know basis. In the new system, everyone has to play. Everyone has to see the full landscape. Transparency is the premium in the new system. If you go point by point, authoritative voice in the old game or more of a coaching voice in the new game, storytelling is more of a premium. If you look at these two playbooks, they are polar opposite. It’s not just a one-size-fits-all. It’s more like here are the new principles for the new game. How do you adapt those into your own parenting, management, schooling, and all those different things? Thinking differently about the world we’re in and the new physics of leadership, and how you apply those in your direct situation. 

TTL 815 Hon. Henry F. De Sio, Jr. | Making Change Global
Making Change Global: Millennials and Gen Z are wired for change and have grown up in this new world, but the reality is they’ve also been given the old playbook.


You brought up a lot of good points. I’m thinking about the silo effect and some other great books that have been out there and how people have tried to get out of them. My son-in-law works for Apple and I know that they do a lot of things where they don’t necessarily report to the next level and that type of thing. They can work in different groups. As I work with different companies around the world to develop curiosity, I am curious how that played a role in the leaders that you researched or that you’ve thought about for your writing? For me, I’ve had a lot of curiosity experts on the show since that’s what I look into. It seems to be the spark to everything. If you have motivation or engagement or any of the things that are trying to figure out in leadership, where do you think curiosity plays a role? Do you think that that’s important? 

Absolutely. Sometimes, it’s even more natural or secondhand to another factor. One of the things from the campaign that I thought was interesting was that we tapped something in the electorate that naturally existed. It wasn’t a Republican or Democrat thing, left or right, blue or red, or anything like that. It was this identity that existed in the electorate. A new DNA I would describe as innovative mind, service heart, entrepreneurial spirit, and collaborative outlook. For me, in some ways, that’s partly what I described as a changemaker.  

What I see in the leaders of these different organizations, including mine from the campaign and all these other leaders that I talked to, is that when they look at the universe around them, the people, stakeholders, and people they’re working with, they see changemakers. They see that innovative mind, service heart, entrepreneurial spirit, and collaborative outlook. Therefore, there’s a certain respect that goes with it and then a real desire to listen to those changemaker voices around you. I always say that if you’re a teacher and you see children coming into your class, you see changemakers coming into your classroom rather than students.  

If you’re a civil servant and you see changemakers versus taxpayers, or you’re in business and you see changemakers coming through your doors and not consumers. In that whole gamut of possibilities, how would you build your organization differently to receive changemakers versus the different other labels we put on people? I find that the common thread through all the leaders that I work with is that when they see changemakers, it changes their leadership, interactions, how they design their organizations, and their whole outlook on how they pursue their different endeavors. 

It is interesting to see some of these big successful leaders and people who maybe are successful financially, but maybe not personally. You’re talking about some emotional intelligence things like empathy. Daniel Goleman has been on the show. We talked about Steve Jobs and some of the things that maybe he could have done better in terms of emotional intelligence. Sometimes, he was great at it. I teach a lot of that in the courses on leadership and we get into ethics a lot. I know you look at this book as empathy-based ethics of co-creative teamwork and all that playbook. When you’re teaching somebody ethics-based leadership, since ethics is subjective, how challenging is that to decide when you’re leading in multiple countries? Maybe it’s okay to bribe somebody in one country, but it’s not here kind of thing. I try to tell my students, “Look at this situation from different perspectives.” Our perception of what we think is the correct thing for us may not be what others see. How do you lead in that setting? 

You’ve hit on the right point, which in the old playbook would say one person leads and everyone else follows in any moment. You point the way and everyone else follows. In this new way of working, you have to be in touch with your own change and how your change affects others. From that point of view then, you’re starting to say, “When we interact together with different other viewpoints, how are we understanding what their viewpoint is as we’re stepping into our own bigness?” In the old way of working, it was always about one person big. You climb on that other person and get as big as you can and maybe step on a person on the way. In this system, it’s about how we let everyone step into their bigness. Your leadership then is based on lifting others up and your success is based on how well you’re lifting others up. This is a mindset shift from the beginning. The other part of this is helping people see the new world we’re in and how interconnected we are now 

I always tell this story about the football player who gets ready for the big game and he’s prepared his whole life for the game. He’s going to meet the other players out on the field. He throws on those shoulder pads, that helmet, and all the big gear that he needs. He runs out onto the field, he sees the other players, and they’re not wearing any of the gear he has. They have shorts. They have flowing hair and they’re chasing after a different football. What do you do when the game for which you prepared your whole life is changed? If you see this new game, then there are probably three reactions. Either one, you’re going to be frozen when you don’t know what to do. The second is you’ll double down on what you’ve always known because that’s how you get things done. That means you’re tackling these guys in the flowing hair and light clothing, or you take off those heavy pads and that heavy helmet. You change the team around you or help the players on your team get into the new game, even as you need to bring new players in. You need to work new muscles.  

The key thing now for people is to see the game that has changed from repetition to everyone leading in every moment, which means that change is happening not linear and faster but explosive and omnidirectional. Your old team will lose the new game. Your old mindset will keep your team out of the new game. You’ve got to be able to see all the things that are happening on that field of play and how your change affects other people. It used to be a game for a few and now, it’s a game for all of us. To your point, if we don’t get in touch with how our change is affecting other people, we will be dangerous and moved to the sidelines. It is about awareness of what the new changes are and the new game is and how you adapt your leadership differently into the new environment that we’re in versus what it was in the past. 

That ties into what I found with my research in perception. There’s a process you go through. You evaluate, predict, interpret, and then you correlate to come up with this process of our reality. Our perception was our reality, but we don’t recognize sometimes until you’re thrown into this football game with the wrong clothes that you’re like, “Oops.” It’s fascinating as you’re saying that because I hear what you’re saying. I’m curious how much servant leadership has played a role in what you’ve researched and how is this different? 

There is a service component to this. If I go into a room of people and I say, “Innovative mind, service heart, entrepreneurial spirit, and collaborative outlook, how many of you does this not apply to?” There’s never going to be any hands up because people do see that’s who they are in the world. A starting point that I take into this is that we are changemakers. We do see ourselves ready to playfully in every aspect of our lives and in society. Here’s where the challenge is. Our world built for repetition was about exclusion. Our world built for repetition was about, “Stay in your lane and get your job done.”  

[bctt tweet=”In a world of explosive change, we all have to be innovating into solutions and possibilities. ” via=”no”]

Whereas in this new world, it’s about, “If you stay inside the lines, it’s going to be a problem for your team because we need innovation.” The old game was about exclusion. The new game is about radical inclusion. One of the big lessons from my shift in the campaign from one leader at a time to everyone leading is that innovation is not about technology or about the few. It’s about bringing teams together that wouldn’t otherwise connect. That’s when innovation happens. In a world of explosive change, we all have to be innovating into solutions and possibilities.  

What I find is that we still have the playbook that tells us to play the old game. We have to push that aside and get into the mindset shift of what does this new game requires and learn radical inclusion. Learn about what does it take for others to help them get into the game and how are our systems keeping changemakers out of the game. I often find Millennials and Gen Z who are grown up wired for change with all the tools for change at their fingertips. They then go into the workplace or even into the classroom where they’re put into a box and it doesn’t make any sense for them. Getting in touch with the change and the mindset shift needed and the new playbook makes a big difference in how people can contribute. 

You’re saying some important things. Going back to what Obama had for one of his to respect everyone, we know people leave bosses and not companies so much. If you’re not respected, for me, that’s one that will make me leave. I have left jobs because of that. How do you teach people who don’t even recognize they’re not respecting others to be respectful? 

First of all, it requires a lot of tools. We go back to the old game. A lot of the tools, systems, and incentives are built for the old game of authority, command and control, hierarchy, and all of those things. I found with the changemakers I’ve worked with that they’re constantly looking at ways to have open, transparent conversations inside the workplace about how do we promote innovation? How do we look at our promotion systems differently? They’re constantly looking at open dialog. They’re looking at more 360 feedback, for example, than one-to-one feedback.  

It goes back to your initial comment, which is they’re learning and growing curious organizations that understand that there’s going to be a failure, and that failure can contribute to success versus our old thinking, which is you can never fail, so only succeed. A lot of it has to do with the cultural norms that are put in place. Once you identify as a changemaker, the biggest challenge then is the system that you’re working in, because for a changemaker to go into a siloed hierarchical system is like being a caged tiger. It just doesn’t work. There are two parts to this. One is you self-identifying as a changemaker, which most of us do, and then building the systems where everyone can be full contributors. This is much of what’s helping fuel Black Lives Matter, #MeToo, and some of the movements that we’re seeing. It is a response on some level to the fact that our systems are not welcoming all voices and therefore, we have to make some adjustments to the culture around us to be able to be fully contributing changemakers. 

Some people might be thinking, “Can there be too many cooks?” They ask me that sometimes with the curiosity teachings that I do. They’ll ask me, “If people keep asking questions, we might get off track.” There’s always the concern that they’re going to lose control, don’t you think? 

TTL 815 Hon. Henry F. De Sio, Jr. | Making Change Global
Making Change Global: If you don’t see this new game clearly, then your workplace is not going to accommodate this.


Maybe a manager is always going to be concerned about losing control. That is part of the process, I’ll go back to my laboratory in the campaign, where during the first sixteen months, we grew from 0 to 2,000 people and we have gone from about a $0 to a $40 million a month budget. That’s in the first sixteen months. In the last sixteen weeks, we went from 2,000 to 6,000 staff. We went from $40 million a month to $100 million in revenues in the final months.  

That scale of change, if my instinct as a manager was to control that, how many more rules can I put in place? How can I control people in this system where people seem to have a lot of agency? I could not afford for an organization to go off the rails and my candidate to lose because our organization completely collapsed. My instinct as a manager was to control. Once I realized that that was going to be impossible, that rules could not keep up with that kind of change, which by the way is what’s happening in society as wellthen I had to position my leadership and the leadership of my team so that everybody coming in would know the norms and the boundaries. I had to count on those people through the existing system we already had to modify and regulate their own leadership so that they were playing within the proper boundaries.  

We had moved essentially from a permission-based system over 21 months to a trust-based system. When everyone is a leader, everyone is a stakeholder. When everyone is a stakeholder, everyone is a steward. My big discovery is that we never went off the rails and we counted on each other to make sure that we modified our own leadership accordingly. We didn’t go flat. We still had managers and we had hierarchy still on some level, but our relationship to each other in that system changed. The key is to understand that you have to create trust and safety, but also people have to understand that their leadership has to be used wisely on a person-to-person basis. That’s why I put so much emphasis on empathy-based leadership as the cornerstone for how you live and work in this new game. 

I’ve worked with a lot of people who’ve worked with old styles of leadership. One of my last bosses worked for Jack Welch. Jack was not exactly the kind of guy that wanted everybody to have that leadership mentality, but he was successful. We get rid of 10% of the no matter how good you are if you’re at the bottom mentality where people don’t feel a sense of trust. It worked and they were super successful. Does that work with Millennials? Do Boomers who were still trying to lead have to reconsider everything? Since we’re talking about change, is it just the Boomers who need to change or is it the Millennials and everybody? 

Millennials and Gen Z are wired for change and have grown up in this new world of change, but the reality is they’ve also been given the old playbook, so it’s a challenge for them as well. That’s why I tried to emphasize that this isn’t a better flavor of leadership or management. We do have to see the new game. When I went from my world of one leader at a time to everyone leading in every moment, the most important lesson for me was what I now call the Changemaker Effect and that is this. When you go from one leader at a time to everyone leads, then you’re moving from a system of everyone making change because that’s what leaders do.  

If everything you change changes everything and everyone is doing it, you’re in everyone’s a changemaker system, and that is the polar opposite of everyone’s repeating their skills system. Change is no longer linear and faster. It’s explosive and omnidirectional. When I came out of the White House 5 or 6 years after I’d gone into the campaign and I looked around me, everyone saw the one leader at a time world, but we were living with these tools at our fingertips that allowed us to be in the change game at every moment, “I have a printing press. I can be a retail seller. I can buy directly. I don’t have to go to the store.” All the things that go with being an opinionator, somebody who can produce content. Now, everybody is in the leadership game. That means that change is no longer linear and faster in the world. It’s explosive and omnidirectional. I’m not talking about a more palatable type of leadership. I’m talking about an imperative for a new kind of leadership that all of us have to understand and deploy to play successfully in this whole new game. 

[bctt tweet=”When everyone is a leader, everyone is a stakeholder. When everyone is a stakeholder, everyone is a steward. ” via=”no”]

As we’re talking about success, you gave different examples. We’ve talked about Obama and your work with him. Is there another example that resonated with you as you were writing this book that you think is important for people to see? 

I love to tell the story of a North Carolina mom in the late 1990s. This was before the internet age and all that social media age. She was concerned about young women getting messaging that define them into society’s girl box before they had the tools to define themselves. She took twelve girls in her community for a run and then built that into a program. It’s a mentorship program where they can get emotional skills and talk together about what it’s like to grow up pre-teen in today’s world, and alongside training for a 5K run. That organization now is Girls on the Run, which is now more than two million women who have learned to define themselves and live happily outside that girl box since 1998.  

How that organization grew up and how it was able to penetrate the school walls that were big fortresses at the time to allow this to be citizens and young women interacting in the community as an after-school program partly. It was acting on that empathy-based leadership, forming unusual teams, adults in the community, official people in the schools, students in the schools, and parents. Also, everyone asserting themselves as leaders, and then putting their changemaking for the good of all. That is the roadmap I see in leaders everywhere. It’s not just an organizational roadmap. It is how you create an impact in your community today.  

When I look at the stories in the book, it’s all about these changemakers who have acted on that leadership and created something around them that was valuable to society. The way they work is empathy-based leadership, a new kind of teams, more fluid teams forming around challenges and opportunities, new leadership where no one can be passive and everyone is a contributor, and changemaking for the good of all. You’re now starting to see businesses say, “This is how we need to work.” Institutions that are built for repetition are the last to come into this new game. 

It’s got to be challenging to be in this timeframe. Not just because of technology, Moore’s Law, and everything that’s magnifying the change in terms of that type of thing technology-wise. The impact of social media, the impact of politics, and how everybody is on opposite sides of different discussions, how much is that filtering into the workplace? How can a leader deal with these passions? You talk about having empathy, which is important. A lot of people have passionate ideas like, “I’m right. You’re wrong,” kind of thinking. How is that impacting leadership, especially when politics and things like that come into the office? 

You’re right. We don’t check our changemaking at the door. That is where one of the big shifts has to be. If you’re playing in the new world but seeing the old game and using the old playbook, this is particularly a challenge. Imagine that you’re a CEO in a company. You have 30,000 employees or something and you hire a communications leader who’s going to help you message better. That communications manager in the 1980s learned how to create a message and put that message on the channels of our time then and now. There are so many more channels. Now you’ve got to be skilled at getting that message on all these channels. If you imagine now that you’re sharing your values based on the CEOs megaphone or whatever that is, and you’re not seeing the other thousands of employees have their own megaphones. They’re on Glassdoor. They’re on LinkedIn. They are contributors to the workplace environment. They’re no longer bit players. The communications manager who’s been schooled to put a message on many channels is missing the fact that in a changemaker world, everyone is a communicator.  

Workplaces do have to accommodate this. If you don’t see this new game clearly, then your workplace is not going to accommodate this. Therefore, people don’t want to just mouthpiece messages. They want to make sure their values are being represented. It’s changing everything about how we live and work in the world now. The skillful manager is going to have to be able to accommodate tearing down walls and bringing people together around all the challenges and opportunities of the organization. That is a different mindset than we’ve ever had before and it does make it more of a challenge. If you’re a football player running out on the field, it’s a lot easier to see that new game than it is for the rest of us in the world now. 

The world now is a little different than it was when you were running the campaign in 2008. I’m thinking when you watch the campaigns and things that have gone on since then, would you change anything of how you did it then? What kinds of things would you do differently if so? 

If I was to come into a campaign now, I came into my campaign experience confident and I felt like I had all the tools. The big discovery for me was that our campaign tapped something that existed. I don’t think we knew this so much at the time, that DNA of the innovative mind, service heart, entrepreneurial spirit, and collaborative outlook. We built our organization to accommodate that. The organization around us, our platforms, and the tools we use accommodated people as stakeholders and not as voting consumers or what you might think. That would be the one change that I see.  

Everything I do now, even as a parent and all the other aspects of my life, is if you see changemakers, how do you build it differently? That’s one place I look at. Having said that, every campaign is different. Every campaign takes on the persona of the person who is the candidate, so they grow up differently. In our case, Barack Obama was a community organizer. He was quite comfortable with 6,000 staff as we got bigger. With the wide universe of stakeholders, he was comfortable in that environment. Others build it differently. Joe Biden’s organization grew up in a pandemic. Jen O’Malley Dillon, the campaign manager came in and on the first day, they had to lockdown. She didn’t even see her staff face-to-face. The principles are still the same. How do I build it to accommodate everyone as a stakeholder and everyone involved instead of thinking of it in an old way as a transactional process? 

How much do you think it impacts us as a society as a whole to go from one president to another in terms of the overall leadership impacting how leaders lead in the world? There’s a big difference, from Obama to Trump to Biden. What impact do you think that has in the business world if any? 

In the business world, it’s one more factor in the dynamic change in the strategic landscape for sure. On some level, it’s not even president to president now. We’re in this world where we’re all in each other’s business. The Changemaker Effect is alive and well in society. We have rising individual agency combined with the tools at our fingertips that allow us all to make a change like never before. The falling of walls and society silos so that we have a democratization of leadership. We’re going to have to learn to play this new game differently.  

I go right to young people. How do we prepare our youngest learners to be contributors to this world of dynamic change? When I look at the changemakers I worked with, what I find is a common story. One is you learn around you. You certainly start building empathy for the youth playbook at a very young age. How can we help young people actively develop their empathic muscles at a young age? The second thing I see is particular before kids are seven or from 7 to 11. When they start to get their passions, how do we help young people develop those passions and learn about those passions? Rather than to say, “No, you shouldn’t be passionate about that. Don’t be a bug exterminator, be a doctor.” Instead, let them learn around what they’re passionate about at a young age.  

As they go into their teens, how do we help young people put a team around an idea so that they’re co-creating that idea and letting that surface through their own experiences? As they take those skills into their adult years, they’ve now learned empathy, how to stay curious and engaged around their passions, and how to play in a team of teams’ environment where everyone leads and no one is excluded. As we build that workforce, that’s going to strengthen us in all aspects of society, including the business environment. If you have a business and you have kids failing at changemaking in their youth, you should care about those kids in your neighborhood because they’re ten years away from being your workers. 

TTL 815 Hon. Henry F. De Sio, Jr. | Making Change Global
Changemaker Playbook: The New Physics of Leadership in a World of Explosive Change

I serve on LeaderKid Academy, which one of my students created to work on soft skills like emotional intelligence to kids on high school level, but all the way down through kindergarten. We don’t see enough of that. In my research on curiosity, you mentioned some of the things that I found that inhibit curiosity, which is the environment. The four things that inhibit curiosity are fear, assumptions, technology, and environment. If you have somebody telling you, “You should be a doctor. You should be this. You should be that,” it inhibits that curiosity to go in the area that you want to explore.  

I love that you brought all that up because it ties right in to everything that I talk about when I go to organizations and speak. What you’re talking about is important. We’re all more alike than we are different. Each generation brings with it unique and wonderful things. I was looking forward to seeing what you had to say about leadership in general because change is such a huge part of it. I can’t tell you how many courses I’ve taught where we talk about these topics. This is something that I share with my students and you’ve covered many important things. I’m sure a lot of people would want to follow you, get your book, and find out more. Do you have a site or some way they could find your book or follow you? 

You can go to Amazon to buy the book. My book’s website is My Twitter handle is @HenryDeSio. I certainly welcome people who follow me also on LinkedIn. I’m excited to engage with people around these ideas and hear what people are thinking about these ideas as well. It’s a time for exchange. 

Now that you’re not doing your job at the White House and different things, what is that like for you? What’s that change like? Do you ever want to return to that? Is that another presidential campaign or capacity? Is that just one experience and now you’re up for a different change of what you’d like to go through? 

I find that I move quickly to where my leadership can have the most impact. My leadership, where it was during those five years, had a lot of impacts. I don’t know if I would have the same impact now going back to that. I take 6 or 7 months sabbatical every seven years. I try to get that map out and reposition my leadership. When I did that in 2018, it brought me to this book, which I wrote. It’s brought me to the idea that I want to position my leadership to tackle the thorniest issues in society. That’s where I’m directing my energy. It’s more toward social impact and how people can have an impact in the world now to solve those complex problems. 

We definitely have a lot of those and there’s a lot of work to be done. I appreciate everything that you’ve done. Thank you for sharing what you learned from this book. It’s an amazing compilation of all your experience and what people can learn. Changemaker Playbook: The New Physics of Leadership in a World of Explosive Change written by Henry De Sio. Thank you, Henry, for being on the show. 

Thank you. 

You’re welcome. 

I’d like to thank Henry for being my guest. We get so many great guests on the show. If you’ve missed any past episodes, you can catch them at We also list all the radio stations where the show airs and wherever podcasts play. We’re much on all of those. You can catch us just about everywhere. We also have tweetable moments. If you find something that stands out in your mind from it, please share it with the rest of the world. We love to hear from you and hear what you think. If you’re looking for more information on Cracking the Curiosity Code book or The Power of Perception book, those are all there, as well as the Perception Power Index and the Curiosity Code Index. You can take a lot of the different assessments by dropping down the menus at the top of the screen or you go to the bottom where it says Assessments and you can take more. There are other assessments as well. There is a lot of great information on the site. If you have any questions you can contact me through the site. I’d love to hear from you. Also, if you could follow me @DrDianeHamilton on all the social media stations. I hope you enjoyed this episode and I hope you join us for the next episode. 


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About Hon. Henry F. De Sio, Jr.

TTL 815 Hon. Henry F. De Sio, Jr. | Making Change GlobalHon. Henry F. De Sio, Jr., is known as the global ambassador for changemakers. A leadership advisor, campaign strategist, and keynote speaker, he has served as the executive of both startups and large, complex organizations. As the 2008 Chief Operating Officer (COO) of Barack Obama’s presidential campaign, and then serving as Deputy Assistant to the President in the Obama White House, De Sio came to be intimately acquainted with a new emerging pattern of societal change. He has since followed his campaign-driven passion for hope and change to make change making a global phenomenon.


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