Why Obama Was Such a Fantastic Boss

A trip to Chicago last week left me feeling nostalgic but also inspired to do more about the future.

Last week, I was in Chicago to attend the opening ceremony of the Barack Obama Presidential Center. That event was inspirational. Check out President Obama’s speech when you get a chance, as well as Michelle Obama’s speech, which was spectacular. Equally energizing were the side events with alums from the Obama administration, especially the one when I got to spend a few moments talking to Obama. It made me very nostalgic for the “Glory Days”, which could have been the theme song for the festivities—especially because Bruce Springsteen was there too.

My trip to Chicago also reminded me what an honor and privilege it was to work for President Obama. I joined his electoral campaign as an unpaid policy advisor very early on, when our foreign policy team numbered only a dozen or so people. After the election, I spent three years as a Special Assistant to the President for Russia and Eurasia Affairs at the National Security Council, followed by two years as the U.S. Ambassador to Russia. Our record of foreign policy achievements was mixed. I wrote a whole book about the issues I worked on during this time, called From Cold War to Hot Peace: An American Ambassador in Putin’s Russia. It covers not only my time in Moscow, but other policy issues in which I participated, from arms control and Nato expansion, to the Arab Spring and democracy promotion more generally. In future columns, I’ll return to how I assess that record today. This essay, however, is about something else: why Obama was such a fantastic boss. He remains the best boss I have ever had.

Why Obama Was a Special Leader

First, President Obama read. The first memo I wrote for him while working at the National Security Council was a briefing for his first call with Russian President Dmitry Medvedev. I was new to writing such memos, so of course I overdid it. (I overwrite everything; the first draft of my last book was 1200 pages.) When I entered the Oval Office to brief the president for the first time, I began summarizing my memo verbally. He gently interrupted me and said he had already read the memo. For the next three years of writing memos to the president—one of the most important parts of the job at the NSC—it was always the same pattern. He had read every word. As such, I took the writing of those memos very seriously. It was my chance to communicate directly to the president about major policy issues. As we got to know each other better, he would increasingly use the talking points that I recommended for calls or meetings.

Second, Obama listened. He was a truly excellent listener. He listened patiently to other heads of state when meeting with them. (He once listened to Prime Minister Vladimir Putin list all his grievances about the Bush administration for nearly an hour!) But he listened to staff like me too. The “pre-brief” with the president before a bilateral meeting (“bilats”), a phone call, or a media interview is one of the most precious moments for a staffer. I’ve heard that other presidents either skip them or use the time for other things. I’ve also heard that other presidents can be combative in these briefing sessions. That was never the case with Obama. He was always engaged. He always asked smart questions. For me, these meetings were among the most meaningful during my time at the White House.

There was only one time when one of our briefings got abbreviated. I came into the Oval Office for the pre-brief before an interview with a Russian television company. We were making our first trip to Moscow in summer 2009, and this interview was designed to set the stage for his visit. When I came in, though, Obama was holding a football. (See photo below.)

It was a beautiful day, so he suggested we go out to the Rose Garden and toss a football while I did the briefing. That was a mistake—both because my throwing skills were rusty (I was a quarterback in 8^th grade in Butte, Montana, but that was a long time ago!) and because we did not focus on Russia, and instead talked more about Brett Favre. In the interview that followed, Obama described Putin as having one foot in the present and one foot in the past. Of course, what Obama said was true, but he probably shouldn’t have said it in an interview just days before traveling to Moscow to meet Putin for the first time. During future pre-briefs, I never tossed a football again.

Third, Obama was curious about the world. Time permitting, he always wanted to learn. He reminded me of my colleagues here at Stanford University, and maybe that’s why I always felt so comfortable talking to him. He’d fit right in here at Nerd Nation. The very first time I briefed him one-on-one was just after Russia had invaded Georgia in August 2008. I joined his campaign plane in southern California and flew with him to Reno, Nevada, where we talked for most of the flight about the war. Before then, I had briefed other senior politicians, including President George W. Bush and Vice President Dick Cheney, as well as past presidential candidates. From these experiences, I assumed Obama would want the basic facts and advice on what to say about them. I was wrong. Senator Obama didn’t want me to restate the facts about the war. He wanted me to explain the conflict. When I started my explanation by going back into history a few months, he interrupted me and asked me to start with the collapse of the Soviet Union in 1991. That was different. By the time we were landing in Reno, we were discussing the differences between realism and liberalism in international relations theory. At that moment in the presidential election, he was basically tied with Senator McCain and should have been focused on polling data or his next speech, yet he still wanted time to talk about IR theory!

For the next five years, we got to squeeze in these kinds of conversations during speeches, writing discussions, pre-briefs, and on plane or car rides. The night before his first speech to the United Nations General Assembly in September 2009, I got the chance to explain the main arguments of my last book, called Advancing Democracy Abroad: Why We Should and How We Can. He was interested especially in the academic debate about “democratic peace.” Before a summit meeting with Medvedev in the summer of 2010, we discussed the relationship between democracy and economic growth over hundreds of years of history worldwide, during which I summarized research by economist Douglass North and political scientist Barry Weingast. Obama loved that kind of conversation. And throughout my five years working with him, he was always interested in learning more about Russian history. (His 2009 speech at the New Economic School in Moscow reflected some of that curiosity. Check it out here.) For me, these conversations were special. I had an abbreviated one with him of similar content just last week.

Fourth, Obama was deliberative. He did not rush into decisions. He asked his staff to think about secondary and tertiary consequences of actions. Relatedly, he respected the inter-agency process. For the issues of national security that I worked on, this was a mechanism in which representatives of all the major departments (State, Defense, Treasury, CIA, etc.) came together at the White House in meetings chaired by NSC staff to formulate agreed-upon policies. The outcomes from the interagency meetings that I chaired at the assistant secretary level of the U.S. government eventually made their way up the chain through the Deputies Committee and the Principals Committee, and then to the president—or at least that’s how it felt. Some outsiders complained that we were too slow in making decisions. But this process produced better decisions. It’s obviously missing now.

Fifth, Obama was funny. You could joke around with him. I felt comfortable enough in the photo below to make a joke as we flew to Moscow in July 2009.

And he could do the same with you. In the photo below in December 2010, I was laughing a little too hard at one of his quips as we swapped stories of how we got the New START Treaty done!

Obviously, the issues we were dealing with were very serious, but I appreciated the way Obama could keep things light.

Sixth, Obama genuinely cared about his staff. He created a real team spirit at the White House, which I appreciated. (Most of my days as an academic are spent writing alone, just me in front of my computer—like now.) I remember flying back on Air Force One from Copenhagen in 2009, when he came back to visit me and other staffers in the back of the plane. I was on that trip to participate in negotiations on the New START Treaty. We had made only incremental progress, and I was feeling like a failure. Yet, there was the President of the United States of America kneeling next to my seat on the plane, encouraging me. These kinds of interactions created deep loyalty and devotion to him. Fear was never a factor. He never lost his temper. That was not his style. Now and again, we also got to interact with Obama more informally, in a pick-up basketball game or a road trip, where his “teamer” mentality came out even more.

And we had a great team! Obama picked the best people to serve in his administration. Most of the people with whom I worked at the NSC were real experts in their fields. There were no relatives or cronies at the White House or in senior positions elsewhere in the government. His Secretary of Defense, Bob Gates, had worked for Bush. His Secretary of State Hilary Clinton was his major opponent in the Democratic primaries.

Relatedly, Obama fiercely protected me when Putin’s government and state media started harassing and attacking me. (For the details, see From Cold War to Hot Peace.) I spoke out too much about human rights or the rule of law for the tastes of some mid-level diplomats at the State Department. They blamed me for the deterioration in US-Russia relations. (Things got a lot worse after I left!). Not Obama. In a 2012 meeting with President Medvedev in South Korea, he made clear his anger at how they were treating me. On the car ride back from that meeting, Obama told me how proud he was that Putin was annoyed with me. Secretary of State Hillary Clinton also had my back during these times. But my situation was not unique. Obama was always loyal to his team.

Finally, Obama had principles. Critics could disagree with them, but they could never say that they did not exist. For me, this part of Obama’s leadership was most important regarding our support for democracy and human rights around the world, including in Russia. We did not always do enough. Our response to the Green Revolution in Iran could have been more sophisticated. How we reacted to the civil war in Syria also could have been better. But I never felt that Obama did not care about these issues—just the opposite. They were competing with other national security interests, but they were never ignored by Obama.

For instance, on our first trip to Moscow in 2009, Obama attended a parallel civil society summit—something no previous American president had done. On that trip, he also held a roundtable with opposition leaders. Four years later, during his final visit to Russia for a G20 summit, Obama held another meeting with civil society activists. Included in the room were some of Russia’s top defenders of LGBT rights (a few months earlier, the Russian parliament had passed a law banning the promotion of so-called “gay propaganda”). Putin did not like that. We were discouraged from holding this meeting, and participants were discouraged from attending. We did it anyway. That was Obama’s last official event in Russia. Appropriately for me, it was my last meeting with Obama as the U.S. Ambassador to Russia.

Obama had many more principles that guided his presidency. We never had any major corruption scandals. Neither he nor his family was making money from being president. He endured constant lies about his place of birth, his patriotism, and his politics, but he never had a meltdown on television or Twitter. Decency was a trait that Obama valued, even when talking about his fierce critics. A few people at the event last week in Chicago wore tan suits to remind everyone of the biggest scandal of Obama’s presidency—the day he wore a tan suit! Those were such different days.

No Time for Just Nostalgia

I hope you get a sense of why it was a thrill and an honor of a lifetime to work for President Obama. I have many more stories, but I’ll save them for another time. Last week brought back some of the best memories of my professional career.

In his remarks last week, however, Obama warned us all not to be just nostalgic about the past, but to be inspired to work for a better future. I take that charge very seriously; I came home “fired up and ready to go!” I now plan to be even more engaged in the issues I care about, both abroad and here at home. And if I ever get the opportunity to serve my country again, I’ll seize it. Last week reminded me what a special thing public service can be.