During their last week of class, students in the Spring 2018 Negotiation Workshop had the opportunity to learn from one of the truly influential negotiators of our time: Ambassador Wendy Sherman. It was Sherman’s second time in three years visiting the Negotiation Workshop, and her talk this time around was equally packed with honesty, storytelling, and wisdom.

“Many times in life you’ll find you have to rise to the occasion,” Sherman advised in her opening remarks. In 2011, then-Secretary of State Hillary Clinton appointed her to be the Under Secretary of State for Political Affairs, putting Sherman at the helm of political operations all over the world. In that role and in her preceding roles in government, Sherman has put negotiation theory to the test: she was instrumental in negotiations related to North Korea’s nuclear weapon and ballistic missile programs under the Clinton Administration and was the lead negotiator for the Iran nuclear deal under the Obama Administration. In her words, conveying some envy of the students’ opportunity to practice negotiation in a workshop setting, she said: “I had to learn by doing.”

Ambassador Sherman’s path to international negotiations was a circuitous one: she worked for many years as a social worker and community organizer before landing in politics. Her advice to students, therefore, was: don’t have a five-year plan. “Take opportunities and get a strong core skill set,” she said, “it’s the skill set at the core that you need for whatever you do.”

Throughout her talk, Sherman retraced her steps in social work, community organizing, and international negotiations in order to tease out some of the core skills that have served her. Her experiences illustrated countless key lessons that apply to negotiation more broadly.

She emphasized the importance of slow, deliberate relationship-building with one’s counterparts in a negotiation process. In the first two years of talks with Iranian officials, she says that the group of negotiators got nothing done substantively. Nonetheless, they got to know each other and establish common ground. “No time is wasted in a negotiation,” she said, “Sometimes you have to hit a roadblock before you can break through.” She credited Kerry’s patience and willingness to have private conversations with their counterparts early as what brought about the formal Joint Comprehensive Plan of Action (otherwise known as the “Iran nuclear deal”).

Sherman highlighted the importance of sequencing. Sometimes, she suggested, the most contentious issues in a negotiation need to be discussed upfront in order to unlock the possibility of a deal. But in other cases, as in the Iran negotiations, she suggested that leaving contentious issues until the end of a negotiation can be strategic: “We left the U.N. resolution as the last substantive issue to be agreed upon because we figured by then everyone would want to get to yes, and they did.”

The Ambassador also emphasized the importance of active listening, perspective-taking and understanding the other side’s story. In the Iran negotiations, this meant learning about Iranians’ perspectives on history and views about the U.S. And moreover, she suggested, it meant understanding and appreciating how acute the stakes were for the Iranian negotiators.

Sherman discussed the need to meet a diverse array of interests and the importance of creativity and nuance in accomplishing this goal. In the case of the Iran deal, everyone wanted to ensure that Iran wouldn’t get nuclear weapons, but each member had other interests as well. In some instances, these interests were in tension with one other. When it came to ending sanctions on Iran, Iranian negotiators wanted to use the word “terminate” while Sherman and her team were only willing to “suspend” sanctions. In the end, they agreed to the language of “lifting” sanctions because lifting can mean both terminating and suspending. That level of granularity was critical to accounting for all the interests at the table.

Ambassador Sherman stressed the necessity of thorough behind-the-table preparation. Her team, comprised of hundreds of staff members in the U.S. government, spent hours preparing and strategizing about high-level meetings. She would ask her team to write up an agreement, including extremely technical details, and have the entire team (nuclear physicist or not) go over the imagined agreement for two days, line by line. The rationale for this painstaking process? “First, I wanted to create a group norm where everyone would hear everything,” she explained. “And second, if something in the agreement didn’t make sense to most of us in the room, it had to be explained until it did”. She and her team studied what she called the “right and left” margins meticulously on every possible issue, so that they knew exactly what conditions they were willing to accept.

Ambassador Sherman also underscored the relevance of courage in the absence of trust. Throughout the U.S.-Iran negotiations, she said, Iranian officials would ask her how they could be sure of her intentions to agree or to adhere to an agreement. Her response: “You can’t be sure any more than I can be sure about you. All we have going for us is to strike the best and most durable deal we can.”

Finally, Ambassador Sherman asserted that it is important to know who you are and be who you are. “To some extent,” she said, “we don’t have a choice in what we bring to the negotiating table.” Whether it’s one’s gender, race, religion, emotional state, or professional history, Sherman argued, authenticity is both inevitable and effective. She spoke about finding “the most bizarre common ground” with the Iranian negotiators by explaining to them that she too, having grown up in a religiously Jewish community in Baltimore, was accustomed to not shaking hands with men. (She even shared that those same negotiators later gifted her Persian rugs). And drawing on a story from her upcoming book, Not for the Faint of Heart: Lessons in Courage, Power, and Persistence, she recalled the role that her gender and even, at one particularly tense moment in negotiations, her tears, played in the process with Iranian officials.

Turning to current events, Sherman was not shy about addressing the immense challenges and sensitivities that President Trump faces with North Korea, Syria, and Iran. Her sobering tone and skepticism about the president’s preparedness conveyed deep concern, even as she affirmed the need to reach out and attempt diplomacy. Asked about whether we can consider a “rational actor” to be involved in the U.S.–North Korea negotiations, Sherman first quipped, “are you talking about our leader or theirs?” before going on to say poignantly, “I tend to approach people as rational within their frame, even if that frame might not be mine.”

Ambassador Wendy Sherman’s visit to the Spring Negotiation Workshop is the latest installment in an annual feature of the course in which a prominent real-life negotiator speaks to enrolled students about their professional negotiation experience in an area of practice. Past speakers have included Sarah Hurwitz, Bob Barnett, Ron Shapiro, Rose Gottemoeller, Grande Lum, and Clifford Sloan. The Negotiation Workshop is offered each January term and each spring semester, and combines theory and practice to improve students’ understanding of negotiation and their skills as negotiators.