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Lessons In Leadership: One On One With Ambassador Wendy Sherman

I spoke to Ambassador Wendy Sherman about her journey and best advice

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I recently interviewed Ambassador Wendy Sherman on my podcast, Thirty Minute Mentors. We spoke about Ambassador Sherman’s journey and best advice on a range of topics. Here are some highlights and excerpts from our conversation:

Adam: What are some of the key skills you developed early on in your career that helped shape your success and what are some of your best tips for those early on in their careers?

Ambassador Sherman: I’m now a professor at the Harvard Kennedy School and Director of the Center for Public Leadership, so my life now is about helping folks who are in graduate school who’ve already done some work and want to move on to the next part of their career – a few just out of undergraduate school, but most who’ve had one or two jobs already – that I wish them all an unexpected life. And what I tell them is to get a core set of skills. For me, those were social work skills, both as a community organizer, as a clinician, and I always joke that my clinical skills have come in very handy with both dictators and members of Congress. But my organizing skills trained me to really understand the landscape around an issue or a challenge or a problem: all of the different stakeholders and how they see it – not just what their positions are, but what their interests are, to understand what a group wants, to try to achieve a goal that might be realizable, and then figure out how to put a strategy together to bring sometimes disparate people together, or to negotiate towards an outcome.

Adam: You’ve worked very closely with two U.S. presidents and countless world leaders. Who are the leaders that you admire most and what did you learn from them?

Ambassador Sherman: I think every leader that I’ve admired is different. I certainly have admired President Clinton and President Obama for very different reasons. President Clinton was a master politician. Sometimes that got him in trouble, but he was a master politician. And when you were in the room with him or having a conversation with him, it was as if no one else mattered. He really was an amazing listener. He also had tremendous command of information. When we were at Camp David working on Middle East peace there was nothing he didn’t know. It was just extraordinary, his command of information, but his interpersonal skills were extraordinary. And I think it was very, very helpful to him as President, but his political skills and his understanding of the moment and what was needed politically, was not always heralded; he had people leave the administration around his decisions, around welfare reform, but had others who felt he’d reached across the aisle to try to move policy a step forward. President Obama was one of the most ethical people of integrity I’ve worked with. He also obviously had a smile to beat the band, which was very much in his politics, but when we were doing the Iran agreement, when we were working on that negotiation, he was incredibly clear upfront about how he would define success and so he could tell us what the right and left margins were. And then he gave me and he gave Secretary Kerry tremendous space and authority, always coming back to check in with him, but he had such command of the details of everything we were doing, that he knew what was happening, meaning he could give guidance and then delegate you to try to get the job done. That ability of a leader to have that kind of vision, that clarity – he would listen to different points of view but at the end of the day he would decide having taken in all those points of view, and then he would send you to carry out that vision.

Adam: What are the best lessons you learned from your experience negotiating the Iran deal?

Ambassador Sherman: Well, it’s one of the reasons that I wrote the book Not for the Faint of Heart: Lessons in Courage, Power and Persistence. Throughout the book, which is part memoir and part lessons learned, it looks at the Iran nuclear deal, Middle East peace, Cuban negotiations and North Korea. I think one of the most profound lessons is that none of this is for the faint of heart; that it takes tremendous persistence. People ask me all the time: “Is it really painful? Am I very sad that President Trump decided to leave the deal?” Well, of course I am. But more than anything, I’m concerned for the national security of the country, and of the world, and of our partners and allies, including Israel. And so I keep trying to do what I can. On the day that President Trump withdrew from the deal it happened to be that anniversary just happened. A couple days ago, I was in the two year anniversary. I was invited to Malta of all places and my cell phone rang and it was John Kerry calling to commiserate but also to sort of egg me on and for me to egg him on, to keep fighting for what we knew to be right. So it’s courage, power, and persistence. It takes an understanding of power, which is necessary and can be used for good if you know what you’re doing and what you’re up to and why you’re doing it. And persistence, which is absolutely a necessity. There are other chapters in the book about failure, letting go, about team building, and even about success, but all of those are qualities that are critical and anything one tries to do in life.

Adam: How do you deal with criticism and how do you deal with failure? How can we maintain our mental health and push forward with a winning mindset and how have you?

Ambassador Sherman: Well, I think that it does go back to having done this with a team and we all stay in touch with each other and, you know, sort of cheer each other on and that’s important. It’s also you know, we are in a very difficult time in the country and in the world in this time of Coronavirus. I feel for students because some of these students started their undergraduate careers with 9/11 and now they’re in graduate school during the Coronavirus. And I have a responsibility. I’m a leader in this instance. So I have to keep it going, even on days I have felt depressed or disappointed. I think it’s important to be honest that you have down days too. But together, we can move forward. I came of political age during the Vietnam War. It was a horrible time in this country. We were very divided on issues and marched every week in the streets. Some people are now marching online on a daily basis. We had Kent State, which we also had the anniversary of a few days ago, where students were killed for their protests. We had a tremendous amount of violence in this country, bombings of townhouses in New York by the Weathermen. We had terrible division. But it was also a time of the Voting Rights Act, the Civil Rights Act, the Women’s Movement, the end of the Vietnam War. And although we faced challenges in the years ahead, including Watergate, it also spurned a whole community of activists that continue to be activists and believed in public purpose and public leadership for the rest of our lives. So something very profound and important came out of that very terrible time. The women’s movement was born during that time.

We are in another really, really hard time. I was talking with a group of students [and we discussed]: how can they be activists when they can’t go in the streets or they can’t meet? We talked about how important it was to use the techniques and the tools that we have. There’s some good in that. There was a meeting that I had stopped going to because I could never get back to Washington to go to it. Now I can join online in ways I couldn’t, because I didn’t have the time to travel down to Washington and then to travel back in time for a class I needed to teach. So let’s figure out what’s good about the moment we’re in and use it to create the change we want.

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