How I Got My Career in Foreign Policy: Stephen Sestanovich

Here’s how Stephen Sestanovich got his career in foreign policy. If you’re interested in this series, check out more editions here.

What did you want to be when you were little?

Well, my boyhood heroes were Willie Mays, Harmon Killebrew, and John F. Kennedy. So I suppose you could say my aim was to be either a big league slugger or president of the United States.

Good options.

At any rate, that was my eleven-year-old ambition. I suspect it probably dropped away by the time I was twelve, but I can’t really tell you what replaced it.

When did you become really interested in foreign policy?

Probably the most relevant thing to say here is that my father was in the foreign service, so by the time I went to college, I had only lived in the United States for three-and-a-half years.

Oh, wow!

That didn’t mean I wanted to be a foreign service officer—to the contrary—but it did mean that I acquired more of an up-close familiarity with other countries, cultures, conflicts, and the United States’ place in the world. Living in Singapore, for example, it was hard to miss differences between how Brits and Americans were perceived and received. The Brits were the retreating colonialists. The Americans were something different, something advancing—a little ominous, maybe, but also attractive. That meant that when I went to college, I was more interested in studying international relations, particularly in understanding the major conflict of the time, which was the Cold War and competition between the United States and the Soviet Union.

Where did you live as a kid, other than Singapore? I’m so fascinated.

Italy, Thailand, Finland, and Venezuela.

Amazing.

My father was a generalist, shall we say, not an area specialist.

That’s so cool, and what a great through line you could take into your career. Diving into that—I know one of your first jobs was as a legislative assistant to Senator Daniel Patrick Moynihan. How did you land that job, and what did working with him teach you about the legislative process?

I confess this was in part a matter of who you know, not just what you know.

Moynihan was looking for a new foreign policy advisor, and being a former Harvard professor himself, he called up Sam Huntington for a recommendation. He wanted a newly minted Harvard PhD, and I was one of Sam’s recommendations. Now, why was I interested? Probably I was a little bored by doing the postdoc work in Sam’s center at Harvard. But beyond that, it  was a time of unusual ferment in the American foreign policy debate, and becoming an in-and-outer in Washington seemed attractive. I didn’t think I was making any irrevocable choice to be in. My model was people who could go in for a time and then come out and do something else.

Now about what I learned in Congress, about how Congress works—the answer is both very negative and very positive things. The negative part: so much of what members and staff do seemed kind of frivolous, self-promoting, designed to position themselves for reelection or to generate news coverage that would help with fundraising. Too little about actual legislating.

But there was also the positive side. Congress was, and is of course supposed to be, the ultimate source of Washington power, both of resources and of legitimacy. I’ve found subsequently that in Washington, a little knowledge of how Congress works can enable you to seem like a savvy operator. If you know the difference between an appropriation and an authorization, or have some inkling as to how an initiative or policy proposal will be received in Congress, that’s useful knowledge. I used to talk up the advantages of working in Congress to anybody considering a career in Washington. Needless to say, I’m a little less sure of those advantages today.

That makes sense, the gridlock today is just so much greater. You then pivot into the State Department, before later going to the National Security Council (NSC). We have to condense a bit to cover everything. Having grown up around U.S. foreign policy, what was it like pivoting into the executive branch and seeing it from the inside? Did that change your understanding of it?

One reason for making the move was to escape the downsides of working in Congress. But as I said, this was a time of unusual ferment in American policy, and the executive branch seemed likely to be the place where critical decisions about American strategy would be made.

What did I learn about how it gets made? We tend to have a somewhat caricatured picture—not entirely false—of bureaucratic paralysis, personal feuding, gang warfare, media hypersensitivity. And there’s plenty of that. But in the government, I was also witness to the ability of individuals with an idea, with persistence, with institutional opportunities that they helped to create, to get things done. I saw that in the Reagan administration among people at the Pentagon who did most to shape our arms control positions. I saw it in the State Department among people who developed and enhanced our aid to the Afghan guerrillas. As a junior NSC staffer, I even saw a little of it in the president himself. I had a bit of a ringside seat for watching Reagan wear down [Soviet Union President Mikhail] Gorbachev. All of those were pretty interesting lessons for how political figures and policymakers actually achieve their goals.

You’ve also spent time in the think tank world—at CFR, at CSIS, and also at Carnegie. I’m curious what the benefit was for you of moving out of government and coming into this sector.

For someone coming out of the executive branch, the big advantage of working in a think tank is you get to say what you want. The big disadvantage or challenge is getting anyone to listen to you.

But in the late 1980s and early 1990s, this problem hardly existed for anyone working on the Soviet Union. Something truly weird and historic was clearly going on there. The media, members of Congress, senior people in the executive branch, my former colleagues, local ambassadors, big donors—all wanted to hear about and support new ideas. At CSIS, we had money for—this was before the internet—a project to create a computer network linking up Soviet experts worldwide to share their knowledge and breathless assessments in a daily way. At the Carnegie Endowment, we had support for setting up a multinational research center in Moscow, which survived until the invasion of Ukraine four years ago.

More important than funding, we also had an audience. The Washington Post, the New York Times op-ed pages were always asking for quick takes. The MacNeil/Lehrer NewsHour, as it used to be called, was always ready to debate what the hell Gorbachev or [Russian President Boris] Yeltsin was doing. I’m not saying the world isn’t interested now in making sense of what’s going on in Russia, but the collapse of the Soviet Union was a super unusual period that gave think tankers an automatic audience and encouraged big-picture interpretations of what was happening in the world. 

I want to get to one of the biggest roles in your career—you became the State Department’s ambassador-at-large for the Soviet Union from 1997 to 2001. First, how do you get that job? Does the president call you?

Well, I was approached at the start of the second Clinton administration by the guy who held the position during the first term. Then Deputy Secretary of State Strobe Talbott was, on behalf of the soon-to-be-appointed Secretary of State Madeleine Albright, looking for someone to do his job. This was already 1997, but the dust of the Soviet collapse in 1991 was far from settling, nor was the enormity of the policy challenge in any way diminished. We had to think about—and this is what the job meant—how to navigate a period of transformation, not only with our former adversary, but with all the new states that had appeared on Russia’s periphery. The job that I took was to coordinate within the State Department, but also across government departments, our interactions with all of these new players.

That meant working out a common approach with the Defense Department, the Treasury, the NSC, the U.S. Agency for International Development, and our own in-house aid managers—not to mention Congress, the private sector, and, of course, other governments as well. With so many hands on the wheel, needless to say, we didn’t always agree. I ran into a former Treasury colleague recently who started our conversation by saying he wanted to apologize for how difficult he’d been to deal with in those years.

Better late than never! I’m curious to drill more into those early years of Vladimir Putin’s rise to power.

Did I say I had a ringside seat for Reagan and Gorbachev? That didn’t mean I was in their meetings. But I was at Clinton’s first meeting with Putin in 1999.

I was going to ask if you met him at the time. It’s crazy to think about, but was there an inkling of what he would become or how much he would reshape the country?

We knew Putin had set himself an ambitious agenda, as any successor to Yeltsin would have done—completing the adjustment to post-Soviet existence. We didn’t know exactly where that was going to take him or how well it would mesh with our own hopes, expectations, and interests. But I think we framed the problem pretty well. At the end of the administration, I published an article in The National Interest—which I should confess I did not clear with the White House—on what we should expect from or fear in Putin’s approach. My bottom line then was that neo-authoritarianism and neo-imperialism were two very real possibilities. I thought neo-authoritarianism was the bigger risk than neo-imperialism. Unfortunately, we’ve ended up with both.

Both of them were prescient predictions. In 2001, you took on two new roles—you leave government and join CFR, and you also join the School of International and Public Affairs at Columbia. How do those two roles balance each other, since they both involve writing and thinking about foreign policy questions?

I should say something about CFR at that time, which attracted me to it in a way that it would not have twenty years earlier. CFR had simply become a much more interesting place in that time. I hope I won’t offend anyone who reads this, but I recall a conversation I had in the mid-eighties with a good friend of mine—while I was at the NSC—in which I mentioned the possibility of going to CFR after the government. He was utterly scornful of the idea. He saw CFR at that time as a kind of tedious center of establishment conventional wisdom. And that wasn’t totally wrong. But by 2001, the place had changed a lot. Under [former President] Les Gelb’s leadership, it had become both genuinely new and very lively. That process has continued under Richard Haass and Mike Froman. The change has been equally pronounced in the way Foreign Affairs looks today compared to thirty or forty years ago. So that made it an attractive think tank destination, but I did manage to pair it with a university appointment, and that had some real benefits too.

In a think tank, you have a portfolio or a beat. In a university, you can follow your interests as they change. I got to pursue a wider range of topics in U.S. foreign policy—the subject of a seminar that I was asked to teach—and that ended up becoming my book Maximalist.

There’s a second advantage to a university setting and to teaching: it’s a fierce testing ground for ideas. There’s nothing like a student audience in a weekly seminar to tell you whether your ideas make sense or not. The students who are wide awake or who are falling asleep or who drop out after two weeks tell you a lot about how you’re doing.

Speaking of students, this series is very much geared toward young people who are starting out. Do you have any advice for those who are kickstarting their careers today?

Three bits of advice come to mind. First, master some subject. Learn things about it that most people don’t know. Early in my time at the State Department, when I was just starting out myself, I heard the head of another bureau describe how in hiring, he looked for those who had acquired what he called an analytical edge—from deep digging into some subject or problem—that set them apart from other applicants.

A second thing: give yourself a paper trail. In Washington, many people are in-and-outers, and in making these transitions, it’s good if people on the outside know who you are and what you have to say. In my first years in government, I managed to publish—just as a junior staffer—in the Washington Post, Foreign Affairs, and The New Republic. Getting approval for these pieces was not always the easiest thing to do. One colleague, while reluctantly clearing a piece I wanted to write, told me—only half in jest—that he didn’t think it was a good idea to let people know how the U.S. government thought. But being able to reach an audience outside the government made the in-and-outer life less precarious.

Finally, many of the people in your series have said things like “be ready for new opportunities, go with the flow, seize the moment.” Without disagreeing, I would add: know when to say no. One of my best decisions—which I won’t describe in detail—was to turn down an offer that seemed like a big promotion but would have been a complete disaster. And in fact, it was for the guy who ended up taking it. So know what you’re going to be asked to do, know whom you’re working for, know who is working for you. If that doesn’t feel right, say no and move along.

That’s great advice, actually. Steve, we’ve come to the last question, which is always a fun one. Over the years, you’ve had many interesting work trips and dinners. Is there a most memorable one you could describe for us?

I’ll describe something memorable, but it wasn’t exactly fun. In October of 1999, a group of us from the U.S. government were in Armenia, meeting in the president’s office, with the prime minister and foreign minister sitting in as well. We had been discussing a possible agreement between Armenia and Azerbaijan—something rather like what is being discussed today. As our meeting was breaking up, the prime minister said to us, “Why not walk across the street with me and meet some members of parliament, members of my own party? Have a drink, get acquainted.” He said the foreign minister was going to be coming along with him as well.

We said, unfortunately, we had to decline this wonderful offer because our plane had to take off in time to land in Turkey before dark. But because our meeting was breaking up a little earlier than expected, we invited the foreign minister to come along with us to the airport to continue our conversation, and then he could go back to parliament afterward.

By the time we took off, we learned that the prime minister, the speaker of parliament, and six others had been shot and killed by a group of nationalist assassins. Every time after that I saw the foreign minister, the first thing he’d say to me was that by taking him with us to the airport, we had unwittingly saved his life. And in sticking to our flight plans, we saved our own, too.

That’s incredible. I have chills.

This interview has been edited for length and clarity. It represents the views and opinions solely of the interviewee. The Council on Foreign Relations is an independent, nonpartisan membership organization, think tank, and publisher, and takes no institutional positions on matters of policy.