Prior to serving in the Obama administration, she was the chief speechwriter for Hillary Clinton on her presidential campaign. Her book, Here All Along was published in 2019. She has incredible insights on the art and process of writing speeches that make people sit up, listen and truly feel something.

Can you share your trajectory through the White House?

I got my start in politics as an intern at Vice President Al Gore's speechwriting office when I was in college. The writers I worked for helped me get my first two jobs after college, both of which were failures. In fact, the second one, which was as a speechwriter for a US Senator, the Chief of Staff sat me down and said, “You should really go to law school. I think that would be better for you than speechwriting”.

When I went to law school, I happened to meet a guy who had previously been a speechwriter for President Clinton. He was a classmate and we started freelancing together. He really taught me how you write to be heard, rather than to be read - they are two different skills. From there I had two failed jobs, and three losing campaigns. But the Obama campaign hired me anyway. And he won!

I was there to write for President Obama. But I helped Mrs. Obama with her ‘08 convention speech. After a couple of years in what was a surprising White House career move, I decided to be her head writer. I just felt more at home with her voice.

Do you think you're a better speechwriter for women, as opposed to men?

Not necessarily. I actually think that what determines if you get someone's voice is whether you share their sensibility about speaking. I’m an emotional writer and a storytelling writer. I'm not a policy writer nor a cerebral writer. I've worked for people who are much more policy-oriented and I just wasn't a great writer for those people. One of those people was a woman, Hillary Clinton. She tended to focus on policy and substance in her speeches. I loved her, she's always been my hero. But that wasn't quite the right fit for me.

Whereas Mrs. Obama, she would talk about policy, but she was much more interested in values and stories, and she came at it from a more personal lens, which is appropriate as the first spouse versus a candidate for president.

The first question you have to ask yourself is, what is the deepest, most important, most helpful truth that I can tell at this particular moment? Get really still with this, like, what is true?

What's the art of writing a good speech? Where do we begin?

I think there are three main tips I would give for writing a speech, and frankly, any kind of communication, a memo, an email, whatever. The first thing is just say something true, which sounds very simple, but it's actually kind of deeper than you think. The first question you have to ask yourself is, what is the deepest, most important, most helpful truth that I can tell at this particular moment? Get really still with this, like, what is true?

The second thing I would say is, for the love of God, talk like a human being. If you wouldn't say something to one person, don't say it to lots of people - it doesn't make it better. The speech needs to feel comfortable coming out of your mouth. If you wouldn't greet your colleagues by saying, “Good morning. It is a great pleasure and honor”, then don't say it to a larger audience. Whatever your natural cadence is you've got to capture that.

The final tip is a really important one, which is show don't tell. I know everyone learned that in freshman year writing, but people rarely do it. Let me illustrate what that means. A real-life example is Michelle Obama in her 2016 convention speech. She could have started it by saying on my daughter's first day of school at the White House I was anxious, I was afraid, I was scared, I was worried. Instead, what she said was, ”On my daughter's first day of school, I watched them climb into those big black SUVs with those big men with guns, and I saw their little faces pressed up against the window and I asked myself, what have I done?”

I remember that so well. It just cuts right to your heart. Even if you're not a parent, you know she's scared, she's nervous. She didn't have to tell you that, she showed you. It's memorable. Our brains really aren't meant to remember lists of adjectives, but they are meant to remember images.

Tell me about the structure of speech.

I think this is one of the most important things about a speech. Basically, the structure is the order in which the paragraphs come. If you have a bad structure, you can't have a good speech because it won't flow. It will feel out of order.

There are all different kinds of structures that work. One that I often use in speech writing for public figures is just to start out by thanking people. Thank the people who made the event possible. Then honor the audience. Make it known that you share their concerns and then address their deeper values.

Then tie it to why you are all there - address the issue you came to discuss. Talk about those deeper values that are at stake and about the challenges that you're facing with that issue. Then outline what you're going to do about it. Outline the solution. Then end in a way that's uplifting. It’s helpful to end in a way that enlists the audience's help, the idea that you can’t do it alone. That's a good structure for political speech.

What about editing?

I can't even tell you how important it is. I think there is this myth that writers sit down and kind of articulate this beautiful first draft. I don't know anyone who does that. One of my colleagues once said to me, “Sarah, you just kind of like, dump a bunch of total nonsense garbage onto a page, and then spend a week editing it into something really good.” It is the perfect description of my process.

A couple of tips for editing. The first tip is just cut 10%. It's pretty hard to do that. If it's 1000 word speech, cut 100 words; 100 word email, cut 10 words. You can always put it back, but by forcing yourself to do this exercise, you will immediately hone in on the weakest parts, it helps you see your writing in a different way because you're thinking about it differently.

I think the second thing is to edit in a different format than you wrote it. So if you're typing on your computer print it out and look at it on paper, or email it to yourself and look at it on your phone, or change the font size or the font type. The point is you want to jar your brain a little bit because when you're staring at the same thing over and over again your eyes dance over typos, it just all looks the same, it becomes a blur. You gotta shake it up for yourself.

The last thing is to leave as much time as you possibly can between writing and editing. I always tried to finish speeches the night before they were due, so I could have a pretty final draft. Then, I could wake up the next morning and look at it with fresh eyes. I often caught some real issues and did some real rewriting in the morning. So I think those are sort of key ways to do it.

Have you worked with anyone who has struggled with nerves while public speaking? Any tips?

Public speaking is still one of the number one fears in the US. People are scared of public speaking and dying, which is nuts, and also totally understandable. Something that I've found is that it can be helpful to just kind of give yourself some room to get comfortable at the beginning of remarks.

I think it's actually okay to just say, “Listen, I'm gonna be honest with you. Public speaking is not my favorite thing to do, but I'm here because I really care about X.” You can just own it. And you know, it is kind of amazing to watch an audience soften.

Any thoughts on the length of a speech to avoid losing people?

17 minutes is about as long as people can focus. Keep it short.

Any suggestions for speaking when you're caught off guard? Like a quick interview question?

That's a really, really tough moment. Because when someone asks you a question where you feel called out or exposed or unsure, your body almost has a physical reaction. My advice, just own it. You can just say, that's a great question. Or that's something that I haven't looked into yet. Then you can proceed in a way that doesn't imply that you 100% know the answer. I think that honesty can be really helpful.