In the July 25 edition of Working, Slate’s Jacob Brogan talks to the president’s director of speechwriting, Cody Keenan. Keenan has been with President Barack Obama since 2007, when he would help write speeches for small backyard campaign events—some of which only had 20 people. Today, Keenan touches every speech President Obama gives. (That’s more than 3,000 speeches.) Keenan tells Brogan everything about his process, from starting with a blank page to making last-minute edits to the president’s State of the Union addresses.

And in this episode’s Slate Plus bonus segment, Keenan tells Working about some of the lighter parts of the job—like helping the president with jokes for the White House Correspondents’ Dinner.

Jacob Brogan: You’re listening to Working, the podcast where we talk to people about what they do all day. I’m Jacob Brogan. This season we’ve been visiting the White House—talking to some of the folks employed there about what goes on within its carefully guarded gates. These are stories of ordinary, though frequently very busy lives in an extraordinary place. This week, we spoke to Cody Keenan, President Obama’s director of speechwriting.

Keenan, who started out as an intern nine years ago has been with Obama since he first began campaigning for the presidency. Today, he works out of a surprisingly prestigious spot. A windowless office in the basement of the West Wing. Keenan talked to us about the difficulties of writing a speech, from the initial outlining to the feedback he gets from the president when he finished a draft. Sometimes he’s still editing until just before the president walks on stage, but he still takes to time to listen in on the final products and he shared some of the ways he evaluated a successful speech with us.

And in a Slate Plus extra, Keenan, who’s helped the president cover weighty topics, tells us about some of the lighter speeches he’s worked on. If you’re a member, enjoy bonus segments and interview transcripts from Working, plus other great podcast exclusives. Start your two-week free trial at Slate.com/workingplus.

Brogan: What is your name and what do you do?

Cody Keenan: My name is Cody Keenan and I’m the director of speechwriting for the president of the United States.

Brogan: What does a director of speechwriting do?

Keenan: I write speeches for the president.

Brogan: That makes sense. And how many speeches are you involved with?

Keenan: Every single one. There’s a reporter for CBS named Mark Knoller who tracks all these things and the last I saw a few months ago, we had just done our 3,300^th speech. Of all various lengths, statements to State of the Union addresses.

Brogan: How long have you been doing this?

Keenan: I’ve been with the president for about nine years. I joined the campaign in June of 2007.

Brogan: Were you writing speeches at that time?

Keenan: I was. I was the intern in the speechwriting office.

Brogan: How has the process changed?

Keenan: It’s changed considerably. When I first came out and joined, it was just Jon Favreau who was the president’s chief speechwriter. And another speechwriter named Adam Frankel, and I was their intern. And the first thing I wrote was talking points for a backyard event in Iowa for about 20 people.

Brogan: Do you ever feel in the nine years that you’re doing this that your own voice is disappearing into that of the president?

Keenan: Sure, if tomorrow was my last day and I had to go write something on my own, I think it would sound a lot like him. You know, it’s like when someone tells you they go live in foreign country, the first time you dream in a foreign language is when you’ve got it. So I’ll find myself making arguments like President Obama.

Brogan: How did you develop that kind of sense of his voice? Was it just over time or did you have to study it?

Keenan: Yea, it’s like anything else. It takes a long time and you have to study it. You know, it’s like if you want to train for a marathon and you’ve never run before, the first couple days will be tough. But in a few years you’ll be banging out 26 miles. And it was the same with this. When I first got my internship in 2007, I drove across country to Chicago to headquarters and listened to both of his books on tape to try to get his cadence down. Stayed up all night the night before my first day of work watching YouTubes of him giving speeches and fortunately there weren’t that many back then. Now there’s thousands.

But I had to work really hard at it, but I had, you know, an incredible boss and mentor in Jon Favreau who was patient with his edits and would actually explain to me why he would make changes. And the president is very much the same way. Even now after nine years, he’ll say—if he wants to go in a different direction, he’ll explain why. He’ll tell me why he made these edits and he certainly doesn’t have to but I appreciate that he takes the time to do that.

Brogan: What was your first day here like?

Keenan: My first day here was, I think it was Jan. 21, 2009. I did not have a computer yet, which is inexplicable because you’d think there were still computers left over from the people who were in your office the day before. And I was working on a speech for the president to nominate a cabinet secretary. I got a phone call from his secretary then, a woman named Katie, saying can you come over and see the president?

Brogan: Had you interacted with him during the campaign?

Keenan: Never. I had never met him yet.

Brogan: So you’d never been in his presence?

Keenan: No, I’d worked—

Brogan: The first time you’re meeting him is going to be in the Oval Office?

Keenan: I worked on the campaign for a year and a half in Chicago and he was always on the road. I think he came into headquarters twice while I was there just to kind of rally the troops. So I’d never met him and I asked her, I said, you mean like in the Oval Office? And she goes yea. So you know, I you know, threw on a jacket and run across the driveway and get into the, I didn’t have the right color badge at the time because it was still new, and I didn’t think I’d get a badge for like eight months.

So I walk up to the Secret Service desk and say can you tell me how to get to the Oval Office? And it’s not their job to tell you how to find the president, you know? So they called upstairs and finally she came down and I think all in all about 10 minutes had passed before he called to see me. So I walked in and I tried to speak and like suddenly my mouth was just as dry as it could be and I think I got out a yes sir and—

Brogan: This is all on Jan. 21?

Keenan: Yea, or 22.

One of those first two days. And I didn’t even know how to talk to him because we’d just never met. And it turns out that’s why he wanted me to come over. He just said I saw your name on the top of this draft and realized I hadn’t met you.

He just asked me for a few minutes where I was from, I told him Chicago, we joked about the Cubs versus the White Sox and I walked out and then turned to his secretary and then said I think I just blacked out, I don’t even know what just happened in there. But that was it. That was my first meeting.

Brogan: How have your interactions with him changed over the years?

Keenan: We’re comfortable with each other. You know, I think it probably took a while just like it would with anybody. But we can talk about anything, we can joke about anything, we can rant about anything. You know, he’s comfortable telling me exactly what he thinks about a speech or about how I’m doing. And I finally feel comfortable, I can do the same. You know, it took a while, you don’t always want to fight with the president but you discover rather quickly that that’s actually what he expects from his staff, are people to challenge him and his ideas and make sure we’re doing the right thing. You know, and we’ll goof around, joke about sports, movies, things we’ve seen.

Brogan: What was it like learning that you had been promoted to replace Jon Favreau, to take this position?

Keenan: It was exciting and terrifying. Because you know, I remember before we even came to the White House after we won the election, I told Jon that I’d be here to turn the lights out in the end and I meant it.

I didn’t know that I would ever become chief because I was the junior guy on the totem pole when we got here. But it was thrilling and it was also terrifying because suddenly you have no one else there. Jon was always there to show me the ropes and to make sure I was on the right track and now it’s just me going to him. But I’ve found along the way that leaning on my team has made me a much better speechwriter.

So but yeah, I never imagined when I first joined this campaign and we were down like forty points in the Iowa caucuses that we’d be turning out the lights in the White House in 2017. It’s been wild.

Brogan: So you work here. We’re in I guess the West Wing now?

Keenan: Yup, this is the bunker, this my windowless office. We’re underneath the Oval Office. No sunlight, loud ventilation, but lots of privacy. I’ve, you know, tried to make it as homey as possible since there are no windows. So I have a Kennedy wall because my first boss was Ted Kennedy, so I have a painting that he did, a picture of the three Kennedy brothers and couple letters the Senator wrote to me. I have two big photos of my trips to Ireland. I have a couple jumbo photographs of working with the president, one in which he’s dictating what he wants in this year’s State of the Union address, one in which I’m dressed as a pirate, and one in which we’re all working on a speech together.

Brogan: Nice. How many hours a week do you think you spend in this windowless cave?

Keenan: I’m in here about 60 hours a week, unless it’s State of the Union week and then I’m in here about 100 hours.

Brogan: Have you ever ended up having to sleep over in the White House?

Keenan: I have, several times. It was easier in my old office, the one I shared with Jon because we had a long couch. The hallway in this office is so cramped they could only get a love seat in here. So I’ve slept on that love seat on several occasions. It’s really uncomfortable and terrible.

Brogan: It looks like you’re a little tall for it.

Keenan: I’m a little tall for it, but the benefit again to having no windows is that it’s silent and very, very dark in here.

Brogan: How often do you end up pulling all-nighters working on a speech?

Keenan: Not too often, just a few times a year. And it’s usually only because the days are so busy around here and once the river of emails slows to a trickle, there’s something about night time that I at least find makes it easier to think. You know, the world kind of shrinks and you can think bigger thoughts and be alone.

Brogan: In this windowless office, here for 60 hours a week or more sometimes, how do you make sure that you get your vitamin D? Do you have to take tablets or anything?

Keenan: I do, actually. The White House doctor gave me this massive thing of 400 units of vitamin D. I get no cellular reception in here, so I try to go outside once an hour and check text messages and voicemails.

Brogan: So is there a typical day?

Keenan: No, that’s one of the great things about the job. I mean, you know I’d tell you how my day begins but that assumes that a day ever actually ends, you know?

Brogan: When do you usually get started, typically?

Keenan: I typically wake up around six o’clock and the first thing I’ll do is check my work phone to see if anything’s happened over night. The Situation Room will send out emails with things that happened around the world, from whether they’re disasters or coups or whatever.

I’ll check Twitter to make sure nothing is really going on. You know, I’ll check the headlines. If I’ve got enough sleep I’ll go to the gym and take my iPad with me and scroll through the New York Times app. If I haven’t, I’ll go back to sleep for a half hour and then check my email again. My wife also works for the White House, so if she wakes up before me and sees something like that, she’ll alert me—we’ll alert each other to breaking news, basically. And then I’ll try to get into work by about eight o’clock.

Brogan: When you’re looking over all that news, do you already have a sense of what you and your team are going to have to be focusing on?

Keenan: Generally, yes. Every Monday morning we’ll have kind of a senior communications meeting where we plan out the president’s public schedule in terms of you know, where he’s going to be heard over the next month. So we’ll have a general idea of what he needs to be heard on. But you know, by the time you leave any meeting, something might have happened in the world that you know, changes your best laid plans. You know, and I remember with Orlando, my wife woke me up at you know, seven in the morning to say you got to look at Twitter. And then we came into the office.

Brogan: Can you talk about what it’s like to capture that kind of intensely felt response to these things when you’re writing for someone else?

Keenan: Yea. I mean we’ve, you know, we’ve had enough horrible experience with it now that we can do that pretty quickly. But I’d say in the beginning it was, it’s still just as shocking as it was in the beginning but in the beginning when we hadn’t had to endure on as terribly frequent a basis as we do now, we’d spend a lot of time together working on statements and eulogies.

Now, it’s just kind of become a horrible, you know, I hate to use the word routine, but you’ll see a breaking news alert from our media monitor and then you’ll see cable networks start to go to what’s happening. And then you’ll see kind of a responsible race to get the facts. And then you’ll start to see partisan finger-pointing and then you know, ultimately the president will go speak on it and this has all become really condensed with each shooting that goes by. But you’ll also see as the days and weeks unfold after each one, stories of heroism and grace and love and things like that, that are really worth dwelling on and spending time on.

Brogan: Do you spend much time working directly with the president himself? What’s that kind of communication?

Keenan: I do. It totally depends on the day and on the week, if we’re working on a big speech together, like the State of the Union address, I’ll see him six, seven times a day. There will be weeks where I don’t see him at all. And you know, typically it’s just my phone will ring and it’ll be his Secretary Ferial who says can you come upstairs and then I’ll put on a tie and run upstairs into the Oval Office.

Brogan: You have a tie on now.

Keenan: I do.

Brogan: Does that mean you saw him recently?

Keenan: I did.

Brogan: What were you talking about?

Keenan: This morning the Supreme Court ruled on an immigration case so it’s one of those things that just kind of happens and disrupts your day and the phone rings, you have to run upstairs and do a different statement than you were just working on. In this case we had an inkling that the Supreme Court would rule on this at some point so we prepared you know, a couple different statements. We typically do whenever you’re in SCOTUS season as we call it. When they might go one way or another on Obamacare or gay marriage or immigration, we’ll have a couple different statements ready to go. And then the morning of, we’ll just have him take a look at the one that’s actually in line with reality. He’ll make some edits and suggestions and we’ll have to go finish it really fast so that he can run out and deliver the statement.

Brogan: Speechwriting is, I assume, is also a collaborative endeavor in an environment like one?

Keenan: It is. I’m blessed to have a great team. There are nine of us total. Two write for the first lady. Two handle national security. We have one researcher, three others will write on any different topic, so we’ll try to meet every morning. We don’t really collaborate on every individual speech, each person kind of writes their own but we’ll share it with each other, you know, when we’re ready, and get people’s feedback and ideas. You know, is this the right argument? Do you have a better one for it?

And it’s also a collaboration with the president too, who’s an incredible writer in his own right. You know, the Guardian, the British paper, just named Dreams for My Father the fifth greatest nonfiction book of all time. So having to write for someone that can write like that is pretty daunting. But he’s always great about it and views it as a collaboration. You know, we’ll hand drafts back and forth and try to make each one better than the last.

We’ll try not to take up too much of his time but if there’s a speech that we’re struggling with or somewhere where we know he’s going to want to make a big point, we’ll try to get some time on his schedule—usually fifteen minutes or so—and go in there with our laptops and just listen, you know, and let him kind of do the speechifying. We’ll ask him to elaborate, we’ll ask him which points he thinks are most important. If there’s any we find particularly interesting, we’ll ask him if he has any kind of personal insights or you know, anything that jogs his memory about, certainly now that we’re getting towards the end of the presidency, any memories he’s got of the presidency.

Brogan: Do you record it? Or are you just typing?

Keenan: Just typing. Just typing as fast as we can. You know, we try not to ask him to repeat himself or slow down or anything like that.

Brogan: How fast do you type?

Keenan: About a 150 words a minute.

Brogan: That’s a lot of words a minute.

Keenan: Yea, well it’s my only skill. But you know the reason we do that is ’cause I think he’d be one of the first to tell you that you know, if he had 72 hours in a day, he wouldn’t need a speechwriter. He’d be happy to do it all himself. He gives us some raw material to work with and then we’ll try to go turn it into something.

Brogan: Does he tell you when he’s done talking or do you just know when it’s your time to go?

Keenan: We know when it’s time. We know when it’s time. But it’s always, it’s probably one of the better moments of his day I would imagine, because he just gets to think. You know, and create something and you know, talk about what’s on his mind.

Brogan: And he’s not, presumably, being held immediately accountable for that. There’s a little more freedom that he might have when actually giving a speech.

Keenan: Right. Right.

Brogan: Yeah. How much of your time at this point is spent editing versus actually writing?

Keenan: More time editing now, you know, and now that I’m the boss of the team there are things you miss about being the junior person on the totem pole, you know? I mean when we first got here in 2009 we were trying to keep the economy from completely falling apart. I was writing maybe three speeches a week. Now I’ll edit two or three a day from the rest of my team and maybe I’ll be able to do a speech a week or a couple a month, myself.

Brogan: So you look at everything before it goes to the president? Is that how it works?

Keenan: That’s right.

Brogan: How late are you usually here at the White House?

Keenan: Typically, I can get out of here around 7:30.

Brogan: Once you leave are you off of work or are you kind of always glued to your phone?

Keenan: Never, it’s always. We’re always glued to it just because you kind of have to be. But you know, I’ll usually get home about an hour before my wife does and what I like to do just to chill, believe it or not, is cook. Especially prep work. I find that doing the prep work of chopping, dicing, separating things, it’s like the first thing I get to do all day where it’s just kind of mindless repetition and I find it very relaxing.

Brogan: You’ve been listening to Cody Keenan, director of speechwriting for President Obama. In a minute, he tells us about the actual process of speechwriting from the blank page to the actual delivery.

What’s the hardest step of the process of preparing a speech? Is there some kind of hiccup that you find you hit over and over again?

Keenan: It’s the blank page, you know, it’s every time you start a new Word document. That’s always the hardest part but it’s also a hopeful part because there’s infinite creation there. You know, you can make it into anything.

Brogan: Do you have a trick to get yourself going?

Keenan: Just start going. You know, just start going. My one trick is to talk to people.

Brogan: Are you often consulting with policy people outside of your team?

Keenan: Always, the policy people are our saviors.

Brogan: So those are people in the White House that you’re working with?

Keenan: Yea, Domestic Policy Council, National Economic Council, Council of Economic Advisors, National Security Council. But one of the great things about being a speechwriter for President Obama is anyone will answer the phone, you know, when we call. So we can call up a historian or someone at a national museum somewhere, the Library of Congress, and people are wonderful.

Brogan: How do people usually respond. Are they surprised when you call?

Keenan: Always. And sometimes they don’t believe you. So you just give them the number for the main switchboard, say call this back and just ask for me and then they say OK, so what can I do? What books do you need? What can I pull? And it’s pretty great. And we get some really incredible stuff that way. You know, the president always tells us to read widely and reach out to as many people as possible because you know, as a speechwriter, you’re kind of miniature expert in everything but a master of nothing. So I’ll go directly to policy people and say what’s your favorite argument here, what are some interesting new statistics? What could we do better? You know, then it’s an ongoing back and forth between policy wonkishness and colloquialism and we’ll try to find the sweet spot before we give it to the president.

Brogan: So is there a trick to balancing the rhetorical and the sort of policy-based content?

Keenan: Yeah, my crude way of explaining it is I would always say you know, I try to write it as I would explain it to someone in a bar. You know, if there’s a very particularly complicated policy, how would I explain it to somebody who is not versed in this? You know, if I was sitting in a bar with someone over a beer, I would say this is how this policy works.

Brogan: You ever gotten stuck and tried that in person?

Keenan: I have, yeah, all the time. And we do it with our other speechwriters here. You know, if we ever get stuck and feel like we’ve got writer’s block, you know, I’ll go to one of our National Security speechwriters, Terry, works next door, and I’ll go in there and say can you help me with this? And sometimes as I’m talking out loud I’ll come up with it on my own and just say thanks and run back into my office and write it down before I forget.

And so typically, we’ll work with the policy people. We’ll sit down and write out a draft. I try to convince my team to sleep on it overnight, share it with each other, take as much time as you can. Don’t procrastinate, begin early so that you can do that.

Brogan: You’ve written several of the most recent State of the Union speeches. You wrote the most recent one, 2016. What was that process like?

Keenan: I mean to be perfectly honest, the president’s the lead writer—certainly with something that big. He’ll be very clear about what he wants and a lot of people help on that one. The National Security writers will work on the National Security section. I’ll work closely with policy people. So my point is there are a lot of cooks in the kitchen and it’s not like I close myself away and just write it alone.

But it’s always a tough process and you know, I think it’s ruined every single one of my Christmases now for the past eight years. Because we usually try to get the president a draft by the time he gets back from his Hawaiian Christmas with his family. It’s hard because those ones are usually about eight to 12 pages long. You’re trying to make a big argument while also packing in you know, every policy that every person in Washington is dying to get out there. This year was a little different because we decided just make an argument about the kind of country we want to be and went away from the large laundry list, which in some ways was liberating, in some ways made us the content factory rather than relying on policy councils. And it was a challenge. On this one, more than any other, I had to ask for help from the president, from my fellow writers, from a lot of people around here, to help me hone the argument, help me find the right way to put this.

Brogan: Do you set out an outline for yourself? And how do you make sure that the points are getting hit?

Keenan: I always start with an outline. The president’s a very linear, logical thinker when it comes to writing and speaking and I think that comes from being a law professor, but you know, structure is really important to a speech and as soon as he feels confident that we have the right structure in place, that’s when we can kind of start playing around with the content.

Brogan: How long does it take from beginning to end to do something like a State of the Union?

Keenan: It takes, you know, from the first meetings we have to kind of look at it from a 50,000-foot level, until the day he gives it, it’s usually about two months. In terms of writing, I’ll usually start about a week or two before I’m going to give him a draft. This year I went through about 20 drafts before I even gave him one. So it was a little more complicate and nerve-wracking than normal. And you know, it can get kind of lonely in this windowless office around Christmas time. But there’s a lot of relief when it’s over.

Brogan: Generally speaking, for the big speeches, how many people end up reviewing them before it gets spoken to the world?

Keenan: A couple hundred. I don’t have an exact number on it, but the first list we send it to widely is about 150 people on it. For something like the State of the Union address it’ll trickle out into the agencies, so by the end I’d say a few hundred.

Brogan: How long does that kind of clearance process usually take?

Keenan: Faster than I think everyone would like. You know, we’ll usually submit around that morning and ask for edits early afternoon and we’ll give it to the president in the evening. He works on every speech every night and we’ll get it back in the morning with his line edits on it and he has a very kind of neat, professorial penmanship and very easy to follow edits. We’ll make them and then go through one final check with the fact-checkers and then we’re done.

Brogan: And when in the morning are you looking at that, then?

Keenan: Usually get his edits back around 9:30. And it’s rare that he speaks before eleven. You know, just because you don’t want to speak before everyone on the West Coast wakes up. So we usually have some time.

Brogan: Is there a type of edit that the president frequently gives?

Keenan: He typically says everybody instead of everyone. We change that a lot.

Brogan: Everybody, like pal?

Keenan: Like instead of the word everyone, he’ll just say everybody. You know.

Brogan: For the State of the Union. When are you fully done? At what point are you able to kind of walk away from the process?

Keenan: I’m usually fully done about an hour before he delivers it. This year was the first time he made some edits on the way to the capitol. So I finished about 90 seconds before he delivered it.

Brogan: Wow.

Keenan: And then I walk away when we’re finished.

Brogan: And it’s going to a teleprompter or something, so are you making those changes in the—

Keenan: We’re making the changes right in the system itself, backstage.

Brogan: What does that involve?

Keenan: At about nine o’clock p.m.

Brogan: What are those systems like? Is it just a traditional computer that’s sending it to the thing?

Keenan: I still don’t fully understand it. It’s a system of like three laptops and a you know, turning dial and so I would just, I read the changes to the guys who run it and they would put it in.

Brogan: What format are you feeding stuff to this system of laptops and telepromptering?

Keenan: When a speech is done, I just email it in a regular Word document form and I don’t know what magic they work to make it happen.

Brogan: Where do you sit in the room when he’s giving the speech?

Keenan: This year I was on the floor, sitting in one of the chairs towards the back corner, sitting next to Ben Rhodes and Josh Earnest.

Brogan: So you’re sitting in the room. What’s that like?

Keenan: I’ll be totally honest, this year I was just trying to stay awake because I hadn’t slept for about four days. It’s exhilarating and you’re proud of everybody and all the work they’ve put into it, but you’re also one of the only people in the room that knows every word to the speech. You know, so I’ll watch for reaction. Ben and Josh and I would kind of fist-bump each other when something worked. But totally honestly, I was just trying not to fall asleep in a room full of very important people.

Brogan: Do you ever catch him changing words or improving as he goes?

Keenan: He does, yeah. All the time.

Brogan: Does it drive you crazy? Is it good?

Keenan: No, I have total faith in his ad-libs. I do.

Brogan: How do you think about your audience or the audience that will be hearing the speech as you’re actually preparing and writing and editing it?

Keenan: That’s one of the most important things about any speech is thinking about who the audiences is, who you’re talking to, what you want to convey to them. But you also keep in mind that it’s a global audience now so there’s no such thing as thing—if he’s going to give a speech, to borrow something from the TV show the West Wing, the Trout Fisherman’s Association—everyone else is going to see it or at least hear about it. You know, we try not to pander to any one particular audience because the speech is live around the world wherever you are.

Brogan: Is that something that’s changed during your tenure here and with the president? That sense that the audience for every speech is a global one or has that been true all throughout?

Keenan: I think it’s truer than ever. You know, President Bush and his speechwriters didn’t have to deal with Twitter.

Brogan: Right.

Keenan: The next president and his or her speechwriters will have to deal with something that we don’t know about yet. The Internet’s changed the way people consume speeches but it’s also changed the way that we can get speeches out to a mass audience.

Brogan: How do you kind of think in those terms as you’re working?

Keenan: It really change, you know, the way we approach writing a speech. What’s great is our office of digital strategy can help us amplify the speech in ways that you know, we wouldn’t otherwise be able to do. For a long time, we lamented the fact that fewer and fewer people consume a presidential speech. The bully pulpit was maybe getting smaller just because there are a thousand channels to choose from and we can create our own news feeds. But I think you know, in the past couple years we’ve caught up to the game. We actually have data and metrics that show how many people interacted with a speech or shared it or saw it.

Brogan: Do you look at that kind of data as you’re thinking about what works and what doesn’t?

Keenan: I don’t look at that data. I’m a little more old school. I actually look at the number of heads nodding in the audience to see if an argument actually works. If I’m in a room watching the heads nod, you know something’s working. If you see total silence, it’s probably not working. Laughter, applause, things like that and you know, you always check the headlines afterwards to see how people are digesting a speech.

Brogan: Do you read reviews or write-ups, articles of a speech, especially with the big ones like the State of the Union, do you then look over the coverage after the fact?

Keenan: Yea, I’m human. I can’t help it. It’s tough though, you know, if a speech gets panned, it’s tough like everything else. If it gets universally applauded, then fortunately I have my wife to tell me to shrink my head.

Brogan: Nice. So what’s the hallmark of a good speech for you? Yours or one that someone on your staff writes or another that you hear out in the world?

Keenan: I’ve never had a great answer for this. You know, it’s not media coverage, it’s not praise or criticism. It’s honestly, if I feel like—and if the president—more importantly, feels like we’ve made a good case, we’ve told a good story, with the society we live in now, as polarized as it is, you don’t change a lot of minds.

But the truth is, one of the actual great ways to judge it is, you know, in the letters that he gets, our correspondence office will send us the letters he reads each night and every once in a while you’ll get a great one saying you know, I heard your speech and you spoke to me or you changed my mind.

Brogan: So for another episode, we spoke to Fiona Reeves—

Keenan: Oh great.

Brogan: From the correspondence office. Do you actually look at all those ten letters or is it just the ones that are relevant to your—

Keenan: I read all ten every night and then we’ll actually ask her and her team if we’re working on a particular speech, say you know, has the president got any great letters on this? I don’t know how they do it but they’ll send us and incredible batch within about 15 minutes that’s exactly what we asked for. And you know, that often takes a speech to a place that we couldn’t take it on our own, when you include someone’s personal story or someone’s argument that’s an interesting way of thinking about things that I’d never thought of on my own.

Brogan: Is that important to you trying to capture specific, particular voices?

Keenan: It is. It is important. I mean, an important about any speech is empathy. You know, being able to empathize with your audience, walk around in their shoes and the president’s always been very good at that. You know, but at the same time, when the most powerful man in the world comes to your town in a modified 747, there’s only so much you know, connection you can make. So if you can tell someone else’s story, then you’ll see people in the crowd going I know exactly what he’s talking about.

Brogan: Because he’s not just telling his story.

Keenan: You can say I feel your pain. And you can also have a letter from John Smith that’s exactly what you’re going through.

Brogan: But it does seem like especially with his response to some of the shootings and other tragedies that we’ve experienced throughout the last eight years that we’re also feeling his pain, often. That’s one of the things, I think, that stands out about his speechmaking. How do you get that through?

Keenan: Well remember, when it comes to mass-shootings, Barack Obama is the only person in America who has had to console every family member of every victim of every mass shooting that he’s gone to visit. I mean the only person.

So we can’t channel all that pain. You know, we can talk to him about it and see what he wants to work into remarks, but he’s generally the one that will tell us what he wants to say on those and he’ll sit down and he’ll work on them and he’ll pull out the yellow legal pad and write up things that are on his mind, but there are a lot of things that happen behind closed doors in those rooms with those families that the rest of us don’t see.

And that’ll often come through. You know, you don’t need to fake emotion when you’re talking about something like that.

Brogan: Yea. Looking back on the Administration’s legacy, on your own relationship to it, how are you feeling about the next six or seven months?

Keenan: You know, we haven’t had time yet to feel nostalgic. He hasn’t given us that. I’ll admit I’m surprised how much we’ve been doing this year and how fast we’ve been going. You know, as campaigns pick up I think that will only get faster. But you know, it actually keeps me from being sad about the end coming. I have no idea what I’m going to do next. I have no idea where I’m going to live. We just know, my wife and I will both unemployed on inauguration day. And I think after some travel we’ll figure it out.

But you know, you try to wrap up neatly where this country has been over the past eight years. Not just you know, things that he’s done. You don’t need to take a victory lap but you think about where we were eight years ago when everything was falling apart and then incredible, extraordinary things this country has done. Not just policy-wise, but how we’ve moved on gay rights and you know, policies around the world and opened up with other countries and it’s an extraordinary set of accomplishments that I think will only really become clear you know, years from now.

Brogan: What’s it like for you to have been involved with all of that, with that progress, with that change?

Keenan: It’s a blur. You know, it’s hard to isolate specific moments, especially when you’ve gone through 3500 speeches in eight years. But there’s a real sense of pride in watching what people have done here, watching how people have grown up, watching policies come to fruition. You know, you’re seeing a real change in people’s letters coming to the president from where they were eight years ago. Watching people who met here at the White House and on the campaign trail get married, have kids. You know, it’s wild. I don’t know the exact number but I feel like there’s a couple dozen kids now running around the White House that weren’t here a few years ago.

Brogan: You said earlier that you said you would be turning off the lights in the White House. Are you ready to do that?

Keenan: I will be. I will be. I’m not quite yet. We’ve still got some more to do. But I will be, I’ll have worked for him for almost 10 years by then and we’ll have done the best we possibly could. And you know, one of the things I’ll do is, I’ll tell you honestly, President Bush’s team was wonderful to us during the transition so we will be just as good to whoever comes next and show them the ropes and maybe leave them a bottle of something nice.

Brogan: What would be in that bottle?

Keenan: I think it depends on the speechwriting team coming in.

Brogan: What would be in your bottle?

Keenan: Bourbon.

Brogan: Nice. Thanks so much.

Keenan: Yea. Thank you for having me.

Brogan: Thanks for listening to this episode of Working. I’m Jacob Brogan. We’d love to hear your thoughts about the podcast. Our email address is working@slate.com—we do read all of those emails. You can listen all seven seasons of Working at Slate.com/working. This series, Working at the White House, was produced by me and Mickey Capper. Mickey also edits the show.

Our executive producer is Steve Lickteig and the chief content officer of the Panoply Network is Andy Bowers. Thanks to Efim Shapiro and special thanks to Racusen at the White House Press Office.

In this Slate Plus Extra, Keenan tells us about some of the lighter speeches that he’s worked on. He also tells us about one that he recently gave himself.

Do you have a favorite speech that you’ve written for him?

Keenan: In 2011, the 1985 Chicago Bears came to the White House.

Brogan: You’re a big Bears fan?

Keenan: Yea, well I used to have a big picture of it there and that’s the ball I got them all to sign there. I’ll give you a better answer afterwards, but, you know, championship teams comes to the White House every year. The ’85 Bears never got to come because it was—they were scheduled to come the day after the Challenger exploded.

Brogan: Oh.

Keenan: And it was never rescheduled and someone at the NFL put two and two together and said we have a Bears fan in the White House now, let’s make it happen. So the ’85 team all came back in 2011 and I was like this is my dream speech. This is what I want.

So I spent like a full day putting all sorts of cool Bears stuff in there and he was all fired up about it because he’s a Bears fan too and as—you know, you try to act cool around here because there are four star generals walking by and the world leaders and senators and this was the one day I just let it all go and I bought a football and I was walking around the back yard with a sharpie being like Mr. Ditka, will you please sign this, you know. So that was a great day.

 But the speeches I enjoy most are also the ones that are the most challenging. And I think he does too. Either when you’re working through a complicated argument or struggling with things that have touched you deeply, once those are where you really feel like you’ve accomplished something.

Brogan: Are you involved with the funnier speeches? Things like the Press Correspondence Dinner that he gives?

Keenan: All of them. All of them.

Brogan: So how is that different from the more serious, more severe or even the more sort of policy oriented?

Keenan: Those speeches are very much all hands on deck. And you know, we’ll take anything as long as it’s funny. You know, you can’t have a lot of pride with those. I think I had one joke in this final one. But what we’ll do is we’ll typically start about a month in advance and email a wide swathe of people and solicit jokes. You know, here’s some potential topics, give us what you think is funny. And you know, as the month goes on, we’ll end up with about 200 jokes. And we’ll try to get that down into kind of a tight, coherent group of 20. And you just can’t be proud about it. You know, if you think your joke is really funny but 10 people tell you it’s not, it’s probably not.

Brogan: Are there any jokes that got lost to that process that you loved?

Keenan: Always, but I think I’m going let those get lost to history.

Brogan: What about ones that really did succeed?

Keenan: I’m not taking credit for any of them. You know, why don’t you have a drink with Mitch McConnell was one of the funnier ones ever.

Brogan: You recently delivered a graduation speech at NYU. How did that differ from writing speeches for someone else?

Keenan: It was hard because I didn’t really know how to do it myself. You know and I had—and this job takes up so much of my time I had to basically do it all in like two days before I went to deliver it, but what I did was I just thought about—you know, I’d been in the same shoes as those graduates about eight years earlier and I thought about what they were feeling.

You know, how do you get from that seat to be working in the White House in eight years? And I tried to give them you know, advice that felt true to me. The things that I’d followed in my own life. And just basically told them if you find those for you, it’ll take you to a great place. You know, whether it’s the White House or any other job. Stay true to some certain core convictions and beliefs and be kind to people and you’ll end up where you’re supposed to be.

Brogan: Was it weird though, drafting a speech like that that didn’t have a lot of other voices on, a lot of other eyes on?

Keenan: Yeah, it was super weird. It was also great. I didn’t have to share it with anybody. You know, there were no fact-checkers, I could say whatever I wanted. But there was also no teleprompter. There was no advance team, so I had to go run and find a place to print it out myself in the hotel we were staying in where the printer was broken and I was like, well this isn’t going to work.

Brogan: What did you end up doing?

Keenan: I finally ran down to the front desk of the hotel and paid the front desk person five bucks just to print it out. I said please, like you don’t understand. I have to - I’m already late for a speech and I have to—will you please just print this? And so he did.

Brogan: It’s funny though, being in, you know, even as you’re at your most powerful, giving your own speech in your own way, outside the power that you’re used to.

Keenan: Yes. I was in the business center in the hotel and the printer was broken and out of paper and you know, you had to like put in quarters and I was like where am I?