Given the increasing penetration of technology into the lives of billions of people around the world, context for how we think about intersection of diplomacy and civil society is shifting. No one has been more central to that discussion than Alec J. Ross, the senior advisor for innovation to Secretary of State Hillary Clinton, who in many ways defined the practice of “digital diplomacy” in the 21st century. Almost three years ago, I talked with Ross about his role and goals, like supporting “Internet freedom” through funding technology.

He told me then that technology was changing and challenging the hierarchical, traditional authority structures that dominated the 21st century, disrupting the ability of governments, companies and powerful people to control information about themselves or their societies. In many interviews and speaking appearances since, he said that “the 21st century is a terrible time to be a control freak. That’s an observation one could easily applies to the institutions and officials of the United States government.

While the the outcomes of revolutions across North Africa and the Middle East are far from certain, what is clear is that the world has seen historic changes that can be in part attributed to so-called connection technologies. After Ross announced on Twitter and Facebook that he would be leaving the State Department this month, we connected to discuss about his plans and reflections on his tenure. Our unedited interview follows. For more on what’s next for Ross and his thoughts on his work, make sure to read Sarah Lai Stirland’s interview with Ross on 21st century statecraft at TechPresident.

First, what’s next for you?

Ross: I will be returning to private life with an initial focus on three things: writing, learning and advising.

I will be hunkered down on several writing projects. Nothing autobiographical. I’m going to write a book and write for the screen.

I will also be immersing myself in new learning opportunities. After 1 million miles of travel over the last five years, I have seen a lot of the world. I’m eager to explore those remaining parts of the world where I have not yet traveled. I also plan to dig deep and explore areas of emerging opportunity in the innovation space. There are products that only live today in peoples’ imaginations that will help us live happier, healthier, more productive lives while unleashing the next stage of value creation and economic growth. I will be spending a lot of time engaged with the thinkers and entrepreneurs imagining and inventing the future.

Finally, I will spend time as an advisor. I will actively mentor a group of young entrepreneurs and government officials. There is nothing I find more rewarding than investing in emerging talents. I will also start a company that will advise investors, corporations, institutions and government leaders to help them understand the implication of macro factors emerging at the intersection of geopolitics, markets and increasingly disruptive network technologies.

Is there going to be someone who replaces you or that will serve as an analogue to your role?

Ross: I have always focused on trying to have innovation at State become something that is institutional as opposed to individual. A study by Brookings identified 155 full-time practitioners of 21st Century Statecraft at State. So while yes, there will be people (multiple people) coming in to take on the role that I have played, the more important development is the institutionalization of this work beyond the Office of the Secretary of the Secretary of State.

How much did the State Department change while you were there, in terms of its use of technology to accomplish its mission? Where was the status quo when you arrived? Where do you stand as you leave?

Ross: First, I wouldn’t define my mission just in terms of technology. I think the three things in my mission were the technologies, networks and demographics of the 21st century. In terms of how much we changed, I’d say that we went a very, very long way.

When I went to State, most people thought I was crazy. They said that State was the most innovation-averse segment of the federal government. I think we turned that around. In fact, last year, Deloitte & Touche and the Partnership for Public Service ranked State as having the most innovation-friendly culture in the friendly government.

While we produced a tall stack of measurable outcomes, perhaps the biggest impact was on the culture of a sprawling 60,000 bureaucracy spread over 190+ countries. I would
never take the credit for this. State is a very hierarchical organization and the women at the top of the hierarchy deserve the credit.

Hillary Clinton, her Chief of Staff Cheryl Mills, and my thought-partner Anne-Marie Slaughter, State’s Director of Policy planning, were the ones that made this possible, in part by promoting and protecting an agenda from the top-down that could then produce
results from bottom up.

How much does “digital diplomacy” matter, in terms of offline effects? What examples of policy changes have resulted from tweets or other expressions from diplomats or national leaders online?

Ross: I wince when I hear a question framed in terms of the impact of tweets. Twitter and Facebook are important social networks, but they are only two of a large family of platforms and tools that our diplomats use.

I could share 30 examples of offline effects but let me focus on just one: listening Historically, the traditional counterpart of a diplomat abroad is a government minister, a general or a CEO. What social networks like Twitter and Facebook enabled was an ability for our diplomats to listen and learn from the perspective of citizens that aren’t sipping tea with them over a mahogany table, flag flying in the background.

Social media has made our diplomats much better listeners. They understand foreign publics better. I always tell our ambassadors when they start using social media, “remember, you only have one mouth but two ears.”

What have you learned about what doesn’t work?

Ross: You can’t hack a solution to sexual violence in the Congo. As I leave government, the one thing that has most disappointed me is my failure to make an impact in the eastern part of the Democratic Republic of Congo. We came up with a couple good hacks, one focused on creating a mobile alert system and another focused on mobile payments to try and fight corrupt, cash-based systems in the military, but they ultimately failed because of local corruption and bureaucracy. Some solutions require more than code.

How did you and your team learn from or adjust to mistakes or failures? How does relate to “innovation?”

We learned that you cannot force solutions on people. There has to be demand for your supply. You have to create the right incentives, even for piece-of-crap corrupt Congolese generals, if you want them to cooperate with your programs. I think we learned to be more ruthless and less wrapped up in the kumbaya of some of the tech-for-development
crowd.

I think we also learned to embrace risk and not freak out over failure. There were times that it appeared that what we did failed, only to learn, 6 months down the road, that we we built produced some totally unexpected off-the-charts result.

Those who have heard me speak have heard me quote Theodore Roosevelt. I have quoted him 1,000 times and I’m going to quote him 1,000 more because I think it is important. He said that “It is far better is it to dare mighty things, to win glorious triumphs, even though checkered by failure… than to rank with those poor spirits who neither enjoy nor suffer much, because they live in a gray twilight that knows not victory nor defeat.”

People who fear failure will never innovate. A real innovator embraces risk and tunes out haters. One of the things I dislike about social media is that it amplifies the voices of snarky people who live to take people down. They LOVE to identify failure and create a stir about it. There is a special class of social media superstar who comes up with the most erudite take-downs. It is necessary to learn from one’s critics, but to tune out unproductive haters who only want to celebrate failure and paint a dystopian picture of the future.

How did you see foreign leaders and diplomats shift their communications strategies during your tenure? How did the U.S. adjust?

Ross: I think the USA got out there the fastest and the furthest. I think most other foreign ministries have figured out that social media is a powerful tool that they need to account for. Some are doing it well, some are still unnerved by it being an inherently individual versus institutional platform.

You’ve talked before about empowering digital diplomacy at the edge of the network. Some embassy staff have made independent choices that has created diplomatic challenges, as in Egypt. Will that perspective endure? Or will we see retrenchment and increased need to clear messages?

Ross: We’ve sent more than 100,000 tweets in the last 4 years. Fewer than 15 caused problems. The screw-up in Egypt was a result of bad judgment. That happens. The only reason it got attention is because it was using Twitter. People make mistakes on TV and radio all the time, but if they make a mistake on social media it’s “news.” I think that is
decreasingly the case, as people get increasingly accustomed to social media as part of the mainstream.

Under Secretary Clinton, you advanced an “Internet freedom” policy. Internet freedom can mean different things to people, depending upon your politics. After 4 years, what does it mean to you and the U.S.?

Ross: Internet Freedom is the freedom to connect to the Internet, to the websites of one’s choosing and to each other. When people attempt to broaden that already broad definition, it is to serve their personal politics.

We’ve seen that social media or other electronic communications can be used to target activists or journalists, often with deadly outcomes. After 4 years of seeing “connection technologies” enter societies around the world, are you still fundamentally optimistic about their effects?

Ross: I am. These technologies can be used against citizens and they frequently are, to deadly effect. However, this does not reverse the irreversible dynamic of connection technologies putting power in the hands of citizens and networks of citizens at the expense of hierarchies, including the state.

Western tech companies have been publicly identified as sources of surveillance, filtering or other censorship software or hardware to autocratic regimes. What actions did the U.S. take to address those sales? What stances did you take at State?

Ross: We have taken a hard line publicly and privately against companies that certain technologies to authoritarian governments. My own history on this is well-known, from publicly going after the Wiretappers Ball to privately engaging in a way that has significantly curtailed the sale of these technologies.

I have to say, though, that while this has reduced the sale of American technologies to dictatorships, companies from other countries including China and Russia are only too happy to help fill the gap. I may have helped slow the sale of technology from American companies to dictatorships, but I don’t think that necessarily kept authoritarian governments from getting the surveillance technologies that they wanted. This depresses the heck out of me.

Can the U.S. be credible, in terms of restrictions to such technology, if we deploy it ourselves?

Ross: There are certain communities of people who will never view us as credible, but the truth of the matter is that there are laws and due process in the United States that protect our liberties to a degree that simply do not exist in 99% of the rest of the world. That doesn’t
mean we are above scrutiny or criticism, but we remain a country with the clear rule of law.

How much does what the U.S. do at home, with respect to our companies, states and cities, affect our credibility or ability to influence policies abroad?

Ross: It has a very big impact. This is why the Obama Administration’s opposition to SOPA and PIPA was so very, very important.

As you know, the U.S. has developed offensive capabilities online, in terms of the DoD, and, as reported by the New York Times, and deployed code that affected Iran’s capabilities. Our intelligence agencies are ingesting massive amounts of electronic communications. How did that reality affect your ability to advocate for “Internet freedom” and engage in digital diplomacy around the world?

Ross: Without commenting specifically on any alleged cases of America’s use of malware, I will say that “Internet Freedom” and cyber conflict are viewed as separate domains by most intellectually mature audiences.

We’ve talked about a number of different digital projects you’ve worked on or at least been involved in. Where do we stand on “mesh networks” or “Internet in a box?”

Ross: So far, so good. I can’t get into operational details but these projects are out there and we’re seeing good data. They work.

What about digital circumvention technologies or hosting to protect sites against DDoS attacks?

Ross: Circumvention technologies are being used by huge numbers of people abroad. Most of them can thank the State Department for their support of their ability to access an open internet. Re: hosting to protect against DDoS, that is tough and getting tougher. It is getting easier and easier to conduct offensive cyber operations. DDoS attacks are but one example. The power of states and ad-hoc networks of hackers-for-hire to engage in DDoS and other forms of cyber attacks is only going to grow.

What came of the project to use mobile phones along the U.S.-Mexico border?

Ross: Big success. It’s entirely run by Mexican government entities now. These “denuncia anonimas” are now a key part of the fight against the cartels in northern Mexico.

You’ve talked a lot about the dynamic between being “open and closed.” “Cablegate,” where Wikileaks published many diplomatic communiques, dominated a lot of discussion about the State Department and technology for years. What are the limits to “openness,” in the context of government, society or diplomacy? How do you strike the right balance?

Ross: It only dominated discussion about the State Department within the small community of open government advocates. I bet 80% of American diplomats haven’t given an ounce of thought to Wikileaks in a year. Wikileaks had its 15 minutes and not a minute more. This is an area where my views differ from many in the progressive technology community.

28 months after the release of the State Dept cables, here is the headline: “Wikileaks reveals massive rightdoing by American diplomats.” They showed our private actions matched our public policies. They showed our diplomats are very, very good at their jobs.

Wikileaks set the open government movement backward. It wasn’t whistle-blowing because whistle-blowing reveals acts of official wrong doing. What the cables revealed was rightdoing. 28 months later, the State Department looks good and Assange and Wikileaks look silly. Their view, that there should not be secret information of any sort, is beyond naïve.

I think the default setting for government information should be open instead of closed. However, that does not mean that no information should be closed. I think I’ve been a strong advocate for open government going back to the drafting of the Obama’s campaign’s first policy in the spring of 2007, but that doesn’t mean I believe in hypertransparency. I don’t. And I don’t know anybody who has fought in big dogfights in the foreign policy realm who thinks otherwise.

What did you learn from that experience? How did it affect internal operations, practices or your work on innovation? How did it affect American diplomacy? Did we lose key assets or relationships as a result?

Ross: I didn’t learn anything from the experience.

If anything, it increased the resolve of the State Department to be “Internet smart” because it helped prove the power of networks. Certain relationships were strained and certain were damaged beyond the point of repair by the release of the cables. Our outstanding Ambassador to Mexico had to leave his post because the President of Mexico could not get past what he read in the cables.

I think most of the storm has passed, but it undermined our ability to have confidential communications with our interlocutors. No good was served by the release of those cables, other than demonstrating that our diplomats are really good at their jobs.

Are you going to continue to be engaged with these issues at @AlecJRoss? What are the most important issues to you, as you transition, that we should be focusing on as a nation or as individuals concerned about a global polity?

Ross: I am going to stay at it. The single most important issue for me is the creation of an innovation-friendly marketplace at home and abroad. This means immigration reform. It means smarter IP policies. It means data sovereignty and privacy policies that are market-friendly but put more power in the hands of individuals — and no more power in the hands of regulators. I am obsessed about what it will take to unleash the next generation of value creation and economic growth in America.

Look for that and my continued push against the attempts of dictators to take control of the internet.