Dan: 0:00

Stephen Krupin has written speeches for CEOs and doctors and even presidents. He was a speechwriter for President Obama near the end of his second term. What did you find the most ludicrous aspect of the West Wing's portrayal of presidential speechwriters?

Stephen: 0:18

The width of the hallways. They weren't wide enough for us to have the Aaron Sorkin walk-and-talks that frequently.

Dan: 0:27

He was given many difficult assignments while he was at the White House, but there was one speech in particular that he describes simply as...

Stephen: 0:36

Probably the only time in my career I have been asked to write a speech that violated my values and and offended my conscience. I am a big fan of the Washington Capitals and have been since I was five years old. And I was asked to write President Obama's speech congratulating our arch rivals, the Pittsburgh Penguins, when they came to the White House with the Stanley Cup. You know, I had to say nice things about this team that I hate.

Dan: 1:07

Did you get any like subterranean digs in?

Stephen: 1:11

Oh, absolutely. Which was part of my own coping with the fact that this was the team that stopped us from winning every year.

Dan: 1:17

And did you get grief from your family about participating in that?

Stephen: 1:21

I got grief from my wife for having such a hard time saying nice things about people who happen to wear a different colored shirt than my favorite players did.

Dan: 1:30

She just doesn't get it.

Stephen: 1:33

She accurately, thought that this was ridiculous, that I thought this was a challenging assignment on a moral level.

Dan: 1:51

I'm Dan Heath, and this is What It's Like to Be... In every episode, we walk in the shoes of someone from a different profession, a TV meteorologist, a PR crisis consultant, an ice cream truck driver. We wanna know what they do all day at work. Today, we'll ask Stephen Krupin what it's like to be a speechwriter. We'll talk about the perils of writing a good commencement speech, how in writing political speeches you can avoid accidentally offending other countries, and also the most annoying thing that speakers do that makes speechwriters cringe, stay with us. Stephen is sometimes hired to ghostwrite commencement speeches which is really hard work because people expect a lot of that moment but it's so hard to come up with something new to say. How many times can you say, "follow your passion", "don't be afraid to fail", blah, blah, blah. Stephen told me about a time he was hired by a professional athlete who was coming to give the commencement speech at his alma mater.

Stephen: 2:59

And this athlete had set a record in his sport at the collegiate level. And that was one of the reasons he was a favorite son of this university, one of the reasons he was asked back to give the commencement address in a certain year. And as a speechwriter, part of my job is to extract the details that would make the speech interesting. I asked him about that moment when he set that record in his sport, something the university was proud of. And he answered that question by saying, I have no recollection of that moment.

Dan: 3:32

Oh, wow.

Stephen: 3:33

I don't remember. You know, normally this is the worst thing we can hear as speechwriters, which is like, I don't have any details. I can't tell you what day it was. I can't tell you what kind of shot it was in this sport. And so my first reaction was this doesn't give me anything to work with. And then I realized that revelation could shape the entire speech because it turned into an exploration of what are accomplishments?

Dan: 3:55

Ooo.

Stephen: 3:55

What is the difference between the pursuit of that accomplishment and achieving that accomplishment?

Dan: 4:00

Mhmm.

Stephen: 4:01

And that seemed to me a nice narrative framing device that could shape the rest of the speech as a lesson to the graduates of, "You've just accomplished this big thing, graduating. You're going on to accomplish other great things and follow other passions as the cliche says. But how do you embrace that experience and pursue that adventure?" That can be a lesson grounded in the metaphor of, "You invited me here in part because I set this record and I don't remember at all was this a three pointer, a free throw, at home, away, in an unimportant game, in a a tournament game. I can't tell you anything about this shot." And that to me stuck out as something we could build an entire story around.

Dan: 4:47

That is big leagues speech writing right there, to take the absence of a memory and spin it into this kind Dan: this of beautiful theme for the occasion. Dan: this of beautiful theme for the occasion.

Stephen: 4:56

I think the counterintuitive is where we find a lot of our best stuff, and it again relates back to the challenge of saying something different.

Dan: 5:04

Some of the speeches that have stuck with Stephen the most were ones where his clients had something deeply personal to share.

Stephen: 5:12

I had the opportunity to collaborate with a very accomplished physician who was being awarded a lifetime achievement award by his field. This is a good example of a speaker who did not have a speechwriter on retainer, did not have a speechwriter on staff, probably only gave this kind of speech once in his entire life. And he used this opportunity, his acceptance speech for the Lifetime Achievement Award, to announce to his peers and his community that he had terminal pancreatic cancer. And the speech process was so moving and memorable because I had the opportunity to talk to this doctor about how he discovered and diagnosed for himself this disease, talk about what he was proud of, how he was going to spend his remaining time. And it felt like a a sacred honor to help him tell his community this devastating news, and that is a speech where you likely have never heard of this person. You likely have never heard of the organization, the event where he spoke, but is the kind of speech that is as memorable to me as writing for somebody whose words are going to be on page A1 of the newspaper.

Dan: 6:24

What were some of the elements of that talk that you remember?

Stephen: 6:28

For somebody in his position, he had a very level head about his diagnosis. And he had said something to me about how he had led a very healthy life. His parents lived into their nineties, and his first thought was, "I don't deserve this." And then he remembered this line from a Clint Eastwood movie he loved, which is, "Deserve has nothing to do with it." And with that clarity, he was able to explore internally and share externally with this audience how he was going to spend his remaining time and what he was grateful for in his life, including the family and personal accomplishments you would expect, but also what he was most proud of as a mentor and a teacher to his colleagues.

Dan: 7:18

So, you were a presidential speechwriter in the Obama administration, and for a certain kind of person, a certain kind of, you know, writerly, expressive individual, that's about as romantic a position as I imagine they can conjure. How do you become a presidential speechwriter?

Stephen: 7:38

A lot of right place, right time. I had worked as a writer, as a speechwriter in politics. I had worked on both of President Obama's campaigns in 2008 and 2012, and I'd worked in his administration at the State Department as the chief speechwriter there. And the opportunity, very fortunately, came up to join the president's speechwriting team in the second term.

Dan: 8:01

That has to be the easiest yes you've ever given in your life.

Stephen: 8:04

It was probably the quickest reply I've ever hit on an email, to start that conversation, to start that interview process, which included conversations and writing tests.

Dan: 8:15

Writing tests? Oh, tell me about that.

Stephen: 8:17

Writing tests are a standard part of the speech writing hiring process, and I've taken them and I've designed them and given them and graded them as I've built teams. What we typically do is put together a mock event scenario and assign a speech to the writing candidates. And it's a speech that could plausibly be given, but it's not an actual speech on the person's calendar.

Dan: 8:42

Mhmm.

Stephen: 8:42

And what we're looking for as we evaluate these writing tests is does this actually sound like the person? Does it take into account things they have said in the past? But does it also move the dialogue forward a little bit? Does it say something a little different? Does it reveal something about the writer's research skills, their creativity, of course, their facility with writing and producing clean copy for the ear as required in the job. Does it meet a deadline, which is important in this line of work as well. And what happens is we will give a field of candidates these speech assignments and then read them anonymously.

Dan: 9:18

Talk a little bit about adapting to Obama's style. I think all of us have heard Obama talk. From my perspective, he's the greatest speaker I can remember in my lifetime as a president, but I'm not sure I'm very thoughtful about why he's so good. You know, his his voice is amazing, but in terms of, like, putting words on the page, what does it mean to draft something that sounds like Obama?

Stephen: 9:43

Well, let me be very clear that he made us look very good. He was the best speechwriter on staff, and I'm sure if he had forty eight hours in a day, he would have written every speech himself. Our job in trying to provide him with drafts that he could feel comfortable with and bring over the finish line and edit and improve and deliver as well as he always did was to understand how he made an argument and how he told a story.

Dan: 10:10

Mm.

Stephen: 10:10

I don't think that finding someone's voice as a speechwriter is trying to do an impression of them. Like you're on Saturday Night Live. And I don't think voices are like snowflakes and fingerprints where everyone has their own individual one and you have to mimic them exactly. I think it is how does somebody make an argument? How does somebody tell a story? And President Obama was a constitutional law professor. Now, I've written for other politicians who were also lawyers before they went into elected office, but they were trial lawyers or prosecutors, and that absolutely influences the way that they structure an argument and lay out evidence and draw a conclusion. It's different for somebody like President Obama who would often go back in time, explain how we got here, talk about what one side believes, what the other side believes, and his whole ethos beyond just the reason why he believes this policy is right was also about moving people to come together. His background as a community organizer famously, and his belief that the most important title in a country is citizen. His approach to it would be laying out the argument and enlisting the audience to say you have a role in making this happen as well.

Dan: 11:25

Tell us about a particular speech you wrote for Obama that lingers in memory for you.

Stephen: 11:31

I had the privilege of writing President Obama's final memorial day address that he delivered at Arlington Cemetery. And one of the challenges of this speech is that the president speaks every year, usually at Arlington Cemetery. And so how do I write the eighth of eight speeches when everything has been said before? And the approach that we picked was to tell the story of three service members who had been killed in combat since the previous Memorial Day. And part of that process required calling the families of these fallen and asking as politely and unobtrusively as we could to tell us something about those who they've lost.

President Obama: 12:19

Charles Keating, IV, Charlie or Chuck or "C-4", was born into a family of veterans, All-American athletes and Olympians -- even a Gold Medalist.

Stephen: 12:30

And we wanted to remember them on Memorial Day, not just for people who had been killed in action, but for actual the the actual lives that they lived.

President Obama: 12:39

Louis Cardin was the sixth of seven children, a Californian with an infectious wit who always had a joke at the ready to help someone get through a tough time.

Stephen: 12:48

These people were fathers and brothers and sons and partners and friends.

President Obama: 12:53

Joshua Wheeler’s sister says he was “exactly what was right about this world. He came from nothing and he really made something of himself."

Stephen: 13:01

He talked a lot about how we remember, what that requires of us, how we can honor those who we think about on Memorial Day just through the simple act of listening to a loved one's story of these lost lives.

President Obama: 13:15

Josh was the doting dad who wrote notes to his kids in the stacks of books he read. Flying home last summer to be with his wife Ashley, who was about to give birth, he scribbled one note in the novel he was reading just to tell his unborn son he was on his way.

Stephen: 13:33

And as he did that for the final story, he gestured to his right where this woman and her infant were sitting.

President Obama: 13:40

Ashley Wheeler is with us here today holding their 10-month-old son, David.

Stephen: 13:51

And all of Arlington Cemetery rose up and gave this thirty second standing ovation. And that was not a standing ovation for a single word that a speechwriter wrote. It was to let this family that had lost everything know that they were seen and heard. And I think that is one of the great privileges of writing for anyone who holds power. It's this power that we hold to let people know that someone in charge is listening to them. That someone who feels very far away knows them and cares about them and considers their problems. Because we don't want listeners just leaving an event thinking, "Oh, that was a well written speech." In fact, we don't want them thinking about the writing at all. We want them to leave that event going, that was the right idea or I never thought of it that way before or let's march.

Dan: 14:54

Stephen told me that for that Memorial Day speech you heard, he’d done some of the actual reporting involved – like, he was the person who called the widow in the audience who Obama recognized. And I was struck by that. We might think of the job as just sitting down to write… But he’s doing a lot of stuff that doesn’t involve writing at all. There’s a less romantic logistical side to the job, too.

Stephen: 15:19

When I was the chief speechwriter at the State Department and we essentially lived on an airplane

Dan: 15:24

Mhmm.

Stephen: 15:25

I would carry my laptop in a bag over one shoulder and a portable printer in a bag over the other. And there were a lot of times when I would be in very ornate ballrooms in a palace or in a parliament while the secretary of state was in another room having the important meetings, and I would be on the floor printing out the latest draft of the speech and sliding it into plastic sleeves and putting those into a three-ring binder so that he could have that at the lectern with him. And then, of course, somebody from an embassy or back at home in Washington calls with an important edit.

Dan: 16:02

Wait. So you're doing, like, the printing of the speech that you're working on?

Stephen: 16:05

We had a lot of support from wonderful colleagues in the Foreign Service and the Civil Service. But if there was an edit in the moment before a speech was to be delivered, I was on my hands and knees putting the pages into the book and then running over to the teleprompter operator, who in this case was often a member of the military, and punching in the last minute edits or changes or corrections at the right spot.

Dan: 16:31

That has got to be one of the most stressful jobs I can imagine. Like, just showing up in some country that you've never been to and probably know very little about, and then having something coherent to say by that evening.

Stephen: 16:44

Yeah. When I first started at the State Department, somebody who had had this exact position before me in a previous administration was kind enough to take me to lunch. And he said, "This job is going to be like being in graduate school, but changing your major every week."

Dan: 17:00

That's a great line.

Stephen: 17:01

And that turned out to be true because we're talking about Ukraine on Monday, and Iran on Tuesday, and climate change on Wednesday, and our partnership with a different set of countries on Thursday. And in the morning, it might be a policy address, and in the afternoon, it might be a press conference where the secretary is giving remarks before answering questions. In the evening, it might be a toast with an ambassador or another foreign minister. And you have to learn how to get smart on a lot of different topics quite quickly. And if you're curious and you enjoy distilling a lot of complex information into an understandable way that an audience can not only understand what's going on, but do something about it, or feel a certain way about it, that can be really rewarding.

Dan: 17:47

How do you make sure that you don't inadvertently... Like, I'm thinking about these things we see from time to time, like, some ordinary hand gesture in the US is just a mortal insult in another country. How do you sort of vet your remarks to make sure you don't inadvertently cause offense?

Stephen: 18:07

We rely a lot on experts on the ground. So this could be true in a domestic setting where we talk to community leaders, or we talk to audience members, or we talk to organizers of the event to get a sense as best as we can of who is in this audience, what unites them, what brings them together at this specific event. Is it random? Is it they all live in the same zip code? Is it they all have the same job? And from there, you can start to understand some different cultural sensitivities. I remember one time when I was working at the State Department, we were going to build an entire speech around this one word because it made sense geographically, and it made sense because of what that word meant. And we sent this draft to the embassy in that country, and they said, "Oh, no no no. You can't use this word as a metaphor for that because this is what other countries in the region use to describe us in a pejorative sense."

Dan: 19:03

Oh.

Stephen: 19:03

And I never would have known that.

Dan: 19:05

Oh, man.

Stephen: 19:05

And that is why we have a research process and a clearance process, and why for all of our frustrations going back and forth with lawyers and with overly sensitive researchers and fact-checkers, they save us so many times.

Dan: 19:19

I wanted to get in the weeds with Stephen about the writing side of things. I think we've all had that experience of listening to a speaker, maybe a business person or a minister who's written down what they want to say and then they're just reading it live and it often comes off as overly formal or clumsy. So anyway, I asked Stephen what's different about writing text that's meant for the audience to hear rather than see.

Stephen: 19:48

I think the first thing to appreciate, and maybe this is a first commandment of speech writing, is that writing for the ear is a fundamentally different dialect than writing for the eye.

Dan: 20:00

Mhmm.

Stephen: 20:00

And that's because our eyes and our ears have different memories and absorb information differently. It's why you wouldn't just read out a white paper or an op-ed and call that a speech. And so what we think about is the cadence and the rhythm of the words as much as we think about the argument that we're building or the stories that we're telling or the calls to action that we're issuing. A speech is many things, but above all, it is an experience. It is a thing where people in the same space are sharing the same energy and then hopefully responding to what is being said or experienced in that room. It is not what is written down on the page. It is not a piece of paper. Any more than a song is line notes or a movie is a script. It becomes a speech when the audience hears it. And without that, it's nothing. And so that principle has to inform how we write and how we consider the audience. And it also informs the way that we prepare a speaker to deliver a speech as naturally as possible. So that could be the way that we set up anecdotes, it could be even the font and the way that we format the page. So there's nothing that undercuts a speaker's authenticity more than when their head is buried in the page and they say, I will never forget the time that my mother told me, without making eye contact with the audience.

Dan: 21:28

Right.

Stephen: 21:29

And that's part of, I think, what you're referring to when you say it, it feels overly formal.

Dan: 21:33

God, that's such a great symbol of what I'm talking about. I will never forget the time. Like, that is such a a written phrase, isn't it?

Stephen: 21:40

It is. And if you will never forget the time, you maybe don't have to read it word-for-word off of the page. So sometimes, I will put it an opening line of an anecdote that came from the speaker that maybe we've workshopped the best way to structure that story, but give them kind of the on-ramp to it. And then maybe a couple bullets just to remind them, but then give them the closing line, and then maybe the off-ramps. What's the point of the story? What's the lesson? What's the moral? But let them tell the story naturally.

Dan: 22:08

I just want to jump in and underline that technique that Stephen just described because I think this is cool. There’s a tension, in public speaking, between polish and authenticity. And he’s saying, you want to polish your opening and ending sentences to a given story. So script those. Those are your on-ramps and off-ramps to the story. And for the heart of it, just be natural. Put bullet points in your notes instead of scripted prose. The ultimate goal here is to make a speaker sound authentic and natural, even when they’ve prepared obsessively. So some speakers, like Obama, can make reading off a teleprompter seem natural. Others might need the bullet-point trick to loosen up. But Stephen said, what you don’t want to do, in the service of authenticity, is abandon your preparation.

Stephen: 23:03

I think there is increasingly a sense that reading off of prepared remarks or a teleprompter is some kind of deficiency or crutch. And you'll often hear speakers say, I had something prepared, but I'm gonna throw it out and I just wanna speak from the heart. And I get what they're trying to do there. But I think reading off prepared remarks is a sign of respect to the audience, that you took enough time to think about what they needed to hear and what they needed to understand, and to draw a connection between you, the speaker, and them, and whatever the issue is that you're talking about, and took the time to prepare something. I think that indicates that you think this is a good use of their time and not just broadcasting that you're winging it.

Dan: 23:54

Yeah. That's a great point. I like your respect point. I remember this keynote speaker that I talked to one time, I saw him before he went on stage, and he kinda took this pride, I don't know what I'm gonna say when I go out there, it just comes to me. And I think, in his mind, that was authenticity. And the received experience was like, "Did you not think about, like, what you were gonna say? Like, did you not consider that this was a precious time to kinda get your thoughts together and say something coherently?" And it sounds like you you see some of that tension too.

Stephen: 24:27

Yeah. I think we have to remember that the audience doesn't have a requirement to listen to the speaker. The burden is on the speaker to capture and to hold the audience's attention. This is true of those big moments, like at the beginning of a speech as you were just saying, signaling that you're not prepared and you're just gonna wing it. It could also be in small moments in the writing, like as you know, or as I already said, or once again. It sometimes can be a little bit of a cue to the audience that they can take the next few seconds off because they're not gonna hear anything new.

Dan: 25:02

So, Stephen, we always end our episodes with a quick lightning round of questions. Here we go. What is a word or phrase that only someone from your profession would be likely to know? And what does it mean?

Stephen: 25:15

"Final final, use this one."

Dan: 25:17

"Final final, use this one." Okay.

Stephen: 25:19

You know, you have file names for your Word documents, and we have, you know, v one, v two, version one, version two of our drafts as they go through the process. But because we are perfectionists and because we get so many edits from other people around, it is not uncommon for final drafts to have later drafts. And so you might have a file name that includes final or final final or our favorite, final final, use this one, which is the one that has to go to the teleprompter.

Dan: 25:48

What's the most insulting thing you could say about a speechwriter's work?

Stephen: 25:53

I think it's two poles on the same spectrum. One is that we are just a transcriber, that we are not collaborating or bringing our own ideas or perspective to the project, or the other end that we are this puppet master who is putting words in somebody else's mouth because the best speechwriting projects and most speech writing projects are collaborations.

Dan: 26:17

What phrase or sentence strikes fear in the heart of a speechwriter?

Stephen: 26:22

"The lawyers have some edits."

Dan: 26:25

Oh, I can't imagine.

Stephen: 26:27

I wrote something once, at the White House, which is a response to a ruling that came from a regulatory body. The United States won in this dispute. I had the temerity to include the phrase, "We won", in the remarks, and it came back from the White House counsel's office with those words struck through and was replaced with, "We achieved a favorable result."

Dan: 26:52

The best legal minds.

Stephen: 26:54

And I'm sure there's a reason. I'm sure there is some actual legal distinction between those two things, but it's, of course, not the way that anyone, let alone the President of The United States, is going to speak.

Dan: 27:05

What's an aspect of your work that you consistently savor?

Stephen: 27:09

I love in the writing process when you feel a puzzle piece clicking into place. Either a narrative device that through trial and error you discover and it holds the whole speech together, or a detail in the research or from history that vividly tells a story or an anecdote that serves as a perfect metaphor or maybe a counterintuitive twist that surprises the audience. When you find those and you think this is something I can build everything else around, or I can nail an ending, or nail the end of a section, that feels really good. What's a tool specific to your profession that you really like using? I really like using text-to-speech software, where I will put a speech when it's kinda near its final draft into that software and have it read it back to me.

Dan: 27:54

Oh.

Stephen: 27:54

I think if you are reading on a screen something that is meant to be consumed by the ears of your audience, it's too easy to skim over long sentences or gaps in logic or complicated constructions, words that shouldn't be next to each other. And if you read it out loud to yourself, which is a good way to proofread speeches, you can kind of read a long sentence quickly to hide that fact, to mask it. But if you have someone else you trust or a text-to-speech software on your computer read it out to you, nothing will make you edit your draft more quickly and point out your own mistakes to you more efficiently than hearing your words read back to you. I don't think I've ever put a draft into that kind of software and had it read to me before I've shared it with a client or a principal and not changed a 100 things in it.

Dan: 28:43

Mmm. I meant to ask you earlier about the effects or or perhaps lack thereof of AI on the profession. What do you see AI changing about the craft?

Stephen: 28:54

Can I answer your question with a question?

Dan: 28:57

Yeah.

Stephen: 28:57

What problem are you trying to solve? I think if you think of writing as something to knock off your to-do list, then I see the value in getting a passable draft out the door. If you are trying to connect a person to other people, like a speaker to an audience, in an authentic way that actually moves them or makes them think differently about something or changes their minds or changes their behavior, I don't think it is yet an efficient tool for that. I think if you think of writing as a burden, then I get the desire for shortcuts. If you think of writing as an opportunity, as a valuable process that clarifies what you think, that helps you discover new connections, and connect different dots, and challenge your assumptions, and force you to be precise in how you articulate your ideas. Why would you want to skip that step?

Dan: 29:59

That was beautifully stated. I'm gonna print that out and put it on my, put it on my computer.

Stephen: 30:05

Thank you.

Dan: 30:10

Stephen Krupin is a speechwriter. This conversation led me down a whole wormhole of thinking about service professions. Speechwriting is one. There are some service people we hire because we don't wanna do the thing they do, like lawn mowing, house cleaning. Other people we hire because they have expertise that we don't... Electricians or accountants. Both of those are forms of outsourcing. Speechwriting is sorta like outsourcing and sorta not. It's more like co-creation. You don't really co-create with a house cleaner or an electrician. Probably the closest profession we've had to co-creation on this podcast is creative director, where a campaign is a mashup of the client's desires and the creative director shaping of those desires. Another similar profession we haven't had yet might be architect. A speechwriter is someone who is not just touching up what you want to say, like a makeup artist or something, but also someone who's broadening your sense of what you could or even should say. Like that commencement speech example of the athlete who built his talk around the absent memory of his record setting moment. That was a speechwriter's inspiration. Finding a fresh way to engage the audience, writing for the ear, not the eye, making last minute tweaks on the teleprompter, and crafting the lines that will live on beyond the moment. Folks, that's what it's like to be a speechwriter. A shout out to recent Spotify commenters, Sally Warren, Speedcrawl, Elaina Watts, and Nadia Willis. Thanks to you all. This episode was produced by Matt Purdy. I'm Dan Heath. See you next time.