Oval Office Hemingway

I went to get a master’s in public policy from Harvard because I wanted to come back to the Senate and keep working for Senator Kennedy. But while I was there, the Obama campaign came calling. It was a mutual friend that Jon Favreau and I shared, and Jon was Obama’s first speechwriter in the Senate. The campaign had just started, and Obama was suddenly going from maybe giving a short speech or two a week to four speeches a day in Iowa, and then big policy addresses. So Jon needed help, and he hired me as his intern.

That was my first speechwriting job, which I then held for 14 years.

Your first job in politics—and I assume this is true for every industry—if you work hard, if you are open to learning and if you are kind to people, there are opportunities and avenues for growth. You can get pulled upwards by someone who recognizes themselves in you or your talent and ability and takes you to the next step. There are infinite ways to become a speechwriter, and they often strike when you’re not paying attention, or you don’t know to look for them.

One reason I pitched a class to Northwestern was that when I graduated, while I had this degree in political science from a great university, it didn’t help me when I needed to find a job. What separates you is what you can do. So I teach my students how to write speeches. It’s not theoretical. I don’t go through the history of political rhetoric. I teach them exactly how to write a speech so that when they’re done with the class they have this portfolio of 10 speeches they can show somebody. I’ve placed some of my better students in the governor’s office, mayors’ offices, presidential campaigns. And it works.

What’s the central idea you try to convey to students?
The central belief is something that’s bigger than speechwriting: It’s worth their time to get involved in politics and public service, even though it’s frustrating and slow-moving. I try to convince them to get into it and change it for the better. That’s the single biggest lesson.

When it comes to speechwriting, the actual content of the course, it’s just to write simply, powerfully, colloquially. Great speechwriting is a collaborative relationship between a speechwriter and the speaker. People are always asking for authenticity like it’s some magical formula, but there’s not really any alchemy to it. It’s just whether or not you’re willing to be yourself.

There are so many people in politics who are not. And people can tell. Americans have pretty sophisticated bullshit detectors these days, especially young people. I try to show students that the speeches most people gravitate to are the ones that talk to us on a human level, that connect emotionally, that don’t try to be too lofty, and that just speak on the level of the people where they are.

We appreciate that as humans. A great speech can just tell people what we already know but we don’t hear enough from people in power. A speech is really something special when the writer and the speaker collaborate well and are just honest with people.

When you talk about authenticity, the speech President Obama delivered on the 50th anniversary of the Selma marches comes to mind. How did you draft it? How much input did you receive from the President?
That was one of his better speeches because I think most importantly, he knew what he wanted to say. It was our best collaboration on a speech, one of the rare ones where every draft we passed back and forth was better than the last. We made each other better.

He always leads the process. He’s always been our chief speechwriter, and that’s one reason why he’s so good at it, or why his speeches will be remembered, because he cared and he worked on them and it showed. He never just walked up to a lectern and read something for the first time. The most important thing about speechwriting is to have a collaborative relationship with the person who’s speaking.

On this one, we pulled together not just historical context but what’s actually happening today, what would make this speech relevant to people who were listening right now, especially young people. That’s who we were going for. So once I sketched out a first draft based on that input, handed it to him, he worked on it, handed it back. We did that five times.

We were aided by the fact that two days before the speech, it snowed just enough to shut down the federal government. President Obama still goes to work, but most of his meetings got pulled. I was not going to miss that opportunity to steal a bunch of his time, and it’s something he would want his time stolen for.

I think I spent probably a couple hours in the Oval that day, just going over drafts of the speech and talking through them. Without that snow day, without the benefit of us being able to work together and pass, we probably would’ve gone through two or three drafts. Instead, we got to do five.

Now, not everyone’s like President Obama, who actually gets the pen out and really works on it and wants to have full editorial control. There are plenty of speakers, probably most, who will want to look at a draft or two, but basically, “Just get it to a place where I can go read it.”

He never wanted it to be that way. He used a teleprompter because by the time he’s ready to speak, every single word in the speech is exactly where he wants it. It’s there for a reason. If we’ve had enough time, it’s down to the syllable. Sometimes he’d say, “This sentence needs an extra syllable or one less,” because there’s a rhythm to it, too.

The argument he wanted to make in that speech was to young people about what it means to be an American, what America itself means, and who gets to decide. He was honoring the 50th anniversary of the marches from Selma to Montgomery, but more importantly, what happened there: This group of almost entirely Black, mostly young people decided to march for the right to vote—not special treatment, just the equal treatment they were promised under the Constitution. To honor the fact that there was this group of young people willing to die for their fundamental human right—an American right—and then 50 years later you have a Black president is pretty extraordinary.

President Obama could’ve spoke on that alone just to mark the occasion. But one of the most important things in our profession is an audience. A captive audience is a terrible thing to waste, whether it’s the audience in front of you or watching on TV. Around the world you’ve got people watching. So he wanted to make this argument in light of the nascent Black Lives Matter movement that was crackling with energy after Ferguson, Trayvon Martin and Tamir Rice.

The country wasn’t fully paying attention to it, and the President just wanted to make sense of it all with this argument that America is what happened on this bridge. Selma is as important to American history as Kitty Hawk and Cape Canaveral and Lexington and Concord and Appomattox—that this is a place where even people without power or privilege can change their country’s course.

How different is it writing for business leaders? In making that switch, did you have to learn any new skills?
I didn’t have to learn any new skills. Good speechwriting is good speechwriting. To step back a little bit, good speechwriting is just storytelling.

“Storytelling” is a word that’s now becoming cliché, but when President Obama and I and our team of speechwriters would sit down before any speech, the first question he’d ask is, “What’s the story we’re trying to tell?” Because every speech should have a good story: a beginning, a middle, and an end. That applies to presidents, priests giving a sermon, CEOs, academics. It doesn’t matter where your speech is, it should tell a good story from beginning to end.

The corporate world is a little bit different. The audience is always a little bit different, whether you’re trying to sell a product or smooth over a failure, or just buck up your employees in a time of COVID-19.

One thing that’s more of a challenge than working in the White House is working with corporate communications teams, who can often be even more risk-averse than politicians. I was surprised to discover that. The great collaborations we have are ones with communications teams that are willing to take risks, who are willing to bare a little more of themselves and talk colloquially with people.

There's no such thing anymore as a private audience. Everyone's got a camera that can broadcast live on the internet. You should assume that whatever you say is going to show up on the front page of The New York Times tomorrow. So when I say take risks, I often just mean be yourself. Talk like a human. Ditch the jargon. You don't have to say certain things.

And the reason I emphasize the word, “have to,” is that there are lot of times we'll be working with a company and some of their team and they'll say, “He has to say this. She has to say that.” No, you don't. If it makes sense in the speech, sure. But don't hide things.

One of the things we try to do is humanize the people for whom we write, especially the ones who say, "Can you make me authentic?” or, "Can you make me sound like Obama?" I can't make you sound like Obama, and you shouldn't want to. You should want to sound like yourself, so that other people say, "Can you make me sound like, you know, X CEO?"

We can make you sound authentic, but there's a lot of work you have to do there too to actually come across that way.

Corporate activism seems to be on the rise—are you seeing that in the leaders you write for?
Some of the most exciting business we’ve had over the last year comes from both companies and political figures who want to get out there and say these things.

We were often rewarded when we took risks in the White House. There would be endless political meetings where people would agonize over, “Can we say this? Can we say that? What’s going to happen if we do?” Usually the American people are pretty stoked to hear someone say what we all already know and believe.

Most hot-button issues are not as hot-button as you think. Climate change really isn’t that divisive an issue anymore. Coming out and saying that police shouldn’t be able to kill somebody on the street isn’t really as divisive as people think. As long as corporate leaders actually want to say this, we want to work with them and help—do it in a way that not only gets them out there on the right side of an issue but positions them for more growth and success.

Comms teams, to their credit, are always really nervous. People are looking for not necessarily corporate activism, but corporations that care. People want to buy products from people that are doing the right thing and doing it well.

It’s rare that you have an opportunity to say the right thing and do better at business, but there’s plenty of those opportunities right now.

What’s your advice for companies looking to improve the caliber of their speeches?
Speechwriting works better when the speaker cares. That’s not to shift the onus from what we do for a living, but we don’t work with clients unless we actually get to speak with the person who’s going to be speaking.

I’ll add too, that speechwriting, like a lot of professions, is overwhelmingly white and male. At Fenway we’re trying to change that. At the White House we tried to change that and we didn’t get as far as we wanted to. For a year or two in the White House we had a team that was half female. We were the first White House speechwriting team ever to have more than one woman. We had four.

At Fenway we make this core to our values—we’re 50% women right now and we’re trying to add writers of color all the time. The reason isn’t just to check boxes or to say that we’re diverse, but because having a diversity of life experience on your team will make speeches better.

People asked all the time, “What’s it like to write for the first Black president?” It’s a challenge because I haven’t lived the experiences he has.

But you can say that about any speech. We would write speeches for veterans or active-duty military, and we hadn’t served. We would write speeches for LGBT audiences and I’m a straight white male. But to have people on your team who’ve lived those experiences will make the speech better.

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Emily Wang is an Executive in Brunswick’s New York office.

Photographs:White House Photo / Alamy Stock Photo