What Writing Speeches for Michelle Obama Taught Sarah Hurwitz about Great Storytelling

“It works out. The muses come. Tolerating discomfort is part of being successful.”

Adam Grant is the bestselling author of Give and Take and Originals, and is an award-winning professor at the Wharton School of Business at the University of Pennsylvania. As part of the Authors@Wharton speakers series, Adam recently hosted Sarah Hurwitz, the chief speechwriter for former First Lady Michelle Obama, for a conversation on writing across the political divide, why imposter syndrome can be a great source for motivation, and how to tell whether someone is involved in politics for the right reasons.

This conversation has been edited and condensed. To view the full conversation, click the video below. 

Adam: A lot of us struggle even to write in our own voices. How does it work when you’re writing in somebody else’s voice?

Sarah: If I said, “Write me a brief speech about this issue in the voice of someone you know really well”—a parent, a friend, a sibling, a roommate—you could probably do it. You can mimic the way that people you know and love talk because you’re really familiar with their voice. How often do you hear your mom’s voice in your head telling you what to do?

Adam: Too often.

Sarah: The way to get to know someone’s voice is to spend time with them. If someone’s written a book, given a lot of previous speeches, it’s a good idea to read those. I remember doing that on the plane from Washington, DC to Chicago when I was joining the Obama campaign. I was reading Dreams From My Father and thinking, “I am so screwed. This guy is amazing. This is like a novel.”

Over the years, spending time with Mrs. Obama in informal settings where we’re just talking, that’s how I’ve gotten to know her voice.

Adam: I’d love to hear your writing tips. We all write, whether it’s emails or term papers or speeches.

Sarah: First, say something true. People often think, “What would make me sound smart, witty, or powerful? What does the audience want me to say?” Those should not be your first questions. Your first question should be, “What is the deepest, truest thing I can say at this moment?”

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If you think about Barack Obama’s convention speech in 2004, he started by saying, “Let’s face it. My presence on this stage tonight is pretty unlikely. All of you are thinking that it’s unlikely that a black guy named Barack Hussein Obama is on this stage.” When someone says something that’s so glaringly true, you believe them, you give them a lot of credit, you can trust them.
“Talk like a person. You see people who get up on stage and kind of lose their minds. They start to give a speech and it’s fake, stilted, and embarrassing. In business, people are like, ‘I’m here to catalyze the leveraging of verticals to unsilo.’”

The second thing is talk like a person. You see people who get up on stage and kind of lose their minds. They start to give a speech and it’s fake, stilted, and embarrassing. In business, people are like, “I’m here to catalyze the leveraging of verticals to unsilo.” In politics, it’s like, “We need to put hard working middle-class American family values first.” What? I would never say that to you. Just talk like a person. If you wouldn’t say something to one person, I wouldn’t recommend saying it to many people.

Third: show, don’t tell. Most of the time when you’re bored in a speech, it’s because the person is telling you a lot instead of showing you.

Mrs. Obama did this beautifully when she spoke at Dr. Maya Angelou’s funeral a few years ago. She was making the point that as a young black girl growing up in Southside Chicago, she didn’t have a lot of role models of black women in newspapers, magazines, or on TV, so Dr. Angelou was a really important role model for her.

She could have said, “It was hard. I didn’t see myself represented. I felt invisible,” but instead, she said, “Growing up, my first doll was a Malibu Barbie.” You see an image of a little black girl playing with this blond, horrible doll and you sense, “This is awful.” You see and feel it as opposed to having some string of adjectives that vaguely alludes to it.

Adam: What is the process like?

Sarah: Every speech, you sit down with the person you’re writing for and say, “What do you want to say?” Mrs. Obama would just lay it out. She’d say a lot of the language she wanted to use, so my job was to take basically a transcript of that. That input was the heart of the speech. That’s what I started with.

I might do some research, then I would come up with a draft. I’d send it around to my colleagues, to our policy people, to lawyers, to fact checkers. Every word of every line of every speech I ever wrote was rigorously fact checked. I’d get her a draft, and do a lot of editing.

Adam: What do you do when you disagree with the person you’re writing for?

Sarah: I don’t, which is generally my policy. I will only write for people with whom I agree. You’ll find that most political speechwriters are in this because we have a certain set of values and beliefs that we want to promote. We’re not just in this to write.

I once worked for someone who had written for someone where he was very anti-death penalty and she was very pro-death penalty. He had an agreement with her that if she ever wanted to talk about the death penalty, he just wouldn’t write it. You can maybe do that with one issue, but I wouldn’t do it with more than one.

Adam: What about more micro-level disagreements, if you think there’s a more effective way to say something, or have a different point of view about what to emphasize?

Sarah: The reason I work so well with Mrs. Obama is we share a sensibility about what makes a great speech. I cannot think of a time where she wanted to say something a certain way and I was like, “That’s not good.” It was always that she’d want to say something a certain way, and I’d think, “That’s so much better than what I would have come up with.”

“At the end of the day, it’s their speech, not yours. They’re the one who has to walk up to that podium, give that speech, and either get the acclaim or the criticism for it.”

Your job as a speechwriter is to push back on your boss if they want to say something that’s not effective. But at the end of the day, it’s their speech, not yours. They’re the one who has to walk up to that podium, give that speech, and either get the acclaim or the criticism for it, so they have to make that call.

Adam: It has to be weird to hear your words coming out of someone else’s mouth and moving people. What is that like?

Sarah: People think, “Don’t you get mad when they get credit for what you wrote?” The truth is, it’s never what I wrote. It’s always a collaboration.

Adam: You’ve made it pretty clear that you feel some degree of imposter syndrome. At what point in your career will that go away?

Sarah: Never. I think it’s always with you when you’re operating at this high level. It’s a joke among my colleagues, “You’re only as good as your last speech.”

I remember one of my colleagues once saying, “Why is it that every time I sit down to write a speech, it’s like it’s the first time I’ve ever done it?” He’d been writing for a decade at this point.

There’s a sense that you’re always proving yourself, and you have to have confidence. Without confidence, you will be totally lost as a speechwriter. Where speechwriters and principals get in a really bad place is when a speechwriter is not quite getting the principal’s voice. Then, the principal is frustrated and doesn’t like them. That makes the speechwriter more anxious, so they become more risk averse, more afraid, and more stilted, and then the principal likes it even less. It spirals into this terrible cycle.

Even really good speechwriters who have good relationships with their principals can get into that spiral once in awhile, where you start to lose confidence. You’re writing a few bad speeches and it starts to feel like, “Have I lost my touch? Am I no longer able to do this?” The only way out of that is to write a good speech. You just have to have the faith that you can do it.

Adam: Feeling like an imposter is a source of motivation?

“It works out. The muses come. Tolerating discomfort is part of being successful.”

Sarah: Yes. If I felt like I was awesome, I would lose motivation. There is a certain discomfort that you have to be able to tolerate when you write speeches. Even when I was working on Mrs. Obama’s 2016 convention speech, I struggled because she had such a clear vision. She knew exactly what she wanted, I just was struggling to execute.

At some point, it works out. The muses come. Tolerating discomfort is part of being successful.

Adam: There’s a lot of talk now about how divided our country is. What can a speechwriter do about that? If you want to deliver a message that’s going to reach people across a spectrum, what are your thoughts on how to do that?

Sarah: Mrs. Obama and President Obama, at every speech, they’re telling other people’s stories. Good speechwriting is telling the stories of the people you serve.

Part of how we bridge this divide is learning people’s stories and telling them in vivid and moving detail. Oftentimes I will start out speeches by saying, “I’m so happy to be here with all of you. I’ve heard about how you did this thing.” Maybe you’re high school students: “I hear that you guys have all gotten yourselves into college. That’s amazing.” Have your principal recognize the audience and tell their story. Maybe that audience is skeptical, but when that audience hears that the principal has taken the time to learn about them, they appreciate it. That’s how you start to see these divides break down.

Adam: As you get a more and more diverse audience, that becomes harder—especially ideologically.

Sarah: Political speeches are hard because you’re talking about everything to everyone. Where do you even start? What do you even talk about?

The way you bridge those [gaps] is telling your story in a way that articulates values that we all share. Mrs. Obama does this well when she talks about growing up in the Southside of Chicago. Her parents didn’t go to college, her father had multiple sclerosis, and as he got sicker and sicker, he would wake up earlier and earlier so that he could have time to button his shirt and drag himself to his job at the city water plant. To him, that’s what it meant to be a man.

When she got to college, she got loans, grants, and scholarships, so he was only paying a tiny part of her tuition. But he was intent on paying that tiny part on time every semester, because he couldn’t bear the thought of her being late with her tuition bill because he didn’t meet what he needed to do as a father.

That story appeals to everyone: conservatives, liberals. Everyone can see their own parent, grandparent, caretaker, friend in that. Telling these personal stories, that’s a way that you bridge those value divides.

Adam: Can you talk about influencing through non-speech?

Sarah: I was talking to someone recently who does media training, and he said, “When you’re on TV, audiences form an impression of you within the first five to ten seconds.” You’ve said eight words, but they’ve already formed a distinct impression of you.

You can tell an audience that you really don’t want to be there if you’re backing away. You can tell them you’re excited if you’re leaning in, engaging.

This is the art of political advance: are there American flags onstage, are there children standing behind you? If Mrs. Obama was speaking about girls’ education, there would be pictures of girls from around the world behind her. That’s amplifying what she’s saying. That’s a very important part of political speechwriting.

Adam: How have you dealt with gender bias when it comes to writing speeches?

Sarah: Writing for women, I definitely am much more sensitive about anger. It doesn’t help men either, but women are much more penalized for it.

“People who are in it for the right reasons don’t really care about recognition. They’re not so worried about getting the credit.”

Adam: One of the things a lot of people struggle with in politics is the question of who’s here for the right reasons. Who has good values versus who’s trying to get ahead? Are there insights from this time you spent in the White House on how to gauge whether somebody’s authentic and trustworthy?

Sarah: Oftentimes people who are in it for the right reasons don’t really care about recognition. They’re not so worried about getting the credit. They just want to get the thing done. They want to help people. I find that the most impressive people in politics are the people who’ve actually experienced the issues that they’re working on.

When I worked for Senator Harkin, I really admired him. He grew up incredibly poor. His entire family suffered from serious health problems. This guy has personally dealt with every issue he was talking about, and you saw that in his passion. That’s true for President Obama, as well.

Adam: I’ve been hearing more and more people say, “I want to go into politics,” or “I want to influence policy.” Do you have advice for how to get a foot in the door?

Sarah: Interning is really important. A lot of internships cannot pay, and if you are not financially well off, you cannot do them, so it makes me uneasy to give this advice. But a lot of people get their start in internships.

It doesn’t have to be that you move to Washington for 10 weeks in the summer. What about your hometown, can you work for a local elected official there? This semester, can you work for a local elected official?

So much of success in politics is just showing up at that campaign office with no job and volunteering until someone gives you a job. A lot of students are like, “Well, I have straight A’s. I’m so impressive. I’m entitled to a good gig,” and in politics no one really cares. What I care about when I’m looking for someone is, are you really good at what you do?

I hired my first deputy in the Obama administration and didn’t find out where he went to college until six months into the job. I didn’t care. I saw his writing. I knew he was talented. People respected him and liked working with him. That’s what mattered.

Adam: There’s growing trepidation about whether the kinds of skills that you bring to the table are going to go away or become less important. We’ve seen news articles written by artificial intelligence that are indistinguishable from journalistic work. Do you think that creative work is here to stay?

Sarah: It’s actually more important now. People say, “In the era of Trump, is speechwriting dead?” No. We need it more than ever. We need people articulating our highest ideals, American values that we all share: honesty, compassion, courage, optimism, determination. Can artificial intelligence do that? Can AI respond to all of the myriad factors of a moment like the Democratic Convention?

There’s something inimitable and indispensable about this human process. I don’t know if AI can do it. Maybe I’m wrong and I’ll be unemployed.

Adam: I hope you’re right. How did you get to the line, “When they go low, we go high?”

Sarah: That line was arrived at by Michelle Obama, who came up with it entirely on her own. My role in that line was typing it into my laptop. I remember thinking, “That’s good. We should put that in.”