Episode 101: David Litt – Thanks Obama

Episode 101: David Litt – Thanks Obama

What does it take to write a killer joke for the President of the United States? About thirty bad ones, first, says David Litt, former speechwriter for President Obama and writer/producer for Funny or Die. David speaks with us about his memoir, Thanks Obama: My Hopey, Changey White House Years, and what he learned working for the world’s most powerful leader. Discover what makes a speech truly energizing, the difference between believing in yourself and arrogance, and how to function in America’s highest-pressure office.

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Website: ThanksObamaBook.com
Book: Thanks Obama: My Hopey, Changey White House Years
Bio: David Litt entered the White House in 2011 and left in 2016 as a Special Assistant to the President and Senior Presidential Speechwriter. Described as the “comic muse for the president,” Litt began contributing jokes to President Obama’s speeches in 2009 and was the lead writer on four White House Correspondents’ Dinners. He is currently the head writer/producer for Funny Or Die’s office in Washington, D.C. Litt has also written for The Onion, McSweeney’s Internet Tendency, Cosmopolitan, GQ, Vanity Fair, The Atlantic, and the New York Times. He lives in Washington, D.C., with his fiancée, Jacqui, and their two goldfish, Florence and Duane.

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Transcript

Peter: Welcome to the Bregman Leadership Podcast. I’m Peter Bregman, your host and CEO of Bregman Partners. This podcast is part of my mission to help you get massive traction on the things that matter most.

With us today is David Litt. David entered the White House in 2011, he left in 2016, as a special assistant to the President and Senior Presidential Speech Writer. If you’ve done the math, this was President Obama, not President Trump. He was described as the comic muse for the President. He began contributing jokes to President Obama’s speeches in 2009 and was the lead writer on four White House Correspondent Dinners. He is currently the head writer producer for Funny or Die’s Office in Washington D.C. He has written a fantastic book, a really fun book to read, “Thanks Obama: My Hopey, Changey, White House Years. A Speech Writer’s Memoir.”
David, thank you so much for being on the Bregman Leadership Podcast.

David: My pleasure. Thanks for having me.

Peter: So this is a podcast for leaders and there’s a number of different levels I want to have this conversation in. You know, one is as a speech writer, right? Most people I know in leadership roles, they’re constantly writing speeches and giving speeches, and I think there’s some interesting insights that you can give to that whole process, and what your process is. And you know, how you make things funny, right? The having to predictably be funny I think is a real challenge. There’s another level at which I want to talk, which is being a mid-level person in one of the most important offices in the country, probably the most important office in the country, and what that means. And also, how you get your opinion heard in a situation like that when you’re new. And then there’s a third, it’s like what it’s like to write things that you may or may not disagree with, you’re writing for someone else and for someone else’s speaking. And then there’s more.

There’s so much I want to talk to you about. I want to talk to you about what it’s like to be so committed to someone. Like, you write so eloquently about your, I don’t know that you would call it romantic love, but you know, your love of President Obama and your commitment to his ideals. And over years, the honeymoon period leaves and yet you also maintain your commitment, and I think that’s a really powerful dynamic that a lot of leaders would want to learn more about, right? Because it’s impossible not to fall out of love and be a little disappointed, but then also to stay committed and be just as passionate.

So that’s a lot. That’s a big, long introduction of all the things I want to talk about in the next 20 minutes.

David: Let’s get cracking on it then.

Peter: All right. So look, first of all, Obama’s an amazing speech writer in his own right, right? So how do you summon the courage to sit down and write, when you know you’re writing, not only for the most important speaker in the world probably, but also one of the best. I imagine that’s pretty intimidating.

David: It was both intimidating, but also very welcome because I know a lot of speech writers in Washington who have the opposite problem. They write speeches that are really good and the boss makes them a little less good, and then they get delivered and they’re even less good than they were on paper. And that’s not true of everybody, but you know I have friends who work in the House and the Senate, and these are great public servants. They’re just … They don’t happen to have that talent for writing or speaking that President Obama does. I mean, very few do. So on one hand it’s exciting, because you know that if you do good work, you’re gonna …

Peter: It’ll show up well.

David: Exactly. That there will be a difference in the final product between your best work and your second best work. Because President Obama was not just a good speaker, but as you pointed out he could recognize good writing when he saw it. Or he knew good writing when he saw it. It was also intimidating for the same reason that if it’s a day when you say, “Oh, you know, I really want to phone it in.” That’s a lot harder to do when the President knows, you know, this is not really that great. And similarly then the Chief Speechwriter. So I worked for Jon Favreau in the first term and Cody Keenan in the second term, and they had that same set of pressures where they were editing my work. And they would know, “All right, if I let this go to the President and it’s not really that good, you’re not going to slip one by him.” And I think that was an important … You know, to some extent knowing that the person at the top was going to hold you to that standard, it was exciting, it made me wanna meet that standard, but it was also then that got reflected through the rest of the organization.

Peter: Did you sometimes dial it in and then cringe as it was read and edited back to you?

David: No. I definitely wrote speeches that were not great and got rewritten completely. I talk about that a lot in my book. And I wanted to write a White House book that talks more about failures than successes since I think … You know, particularly since I was young there, I think that’s a little bit of an outlier in the White House book genre. But to me, most of the times I totally screwed up a speech, it’s not so much because I wasn’t trying hard, it’s because often I started off and started in the wrong direction, and I never made that course correction early on. Where I said, “Oh, you know what? I’m missing something fundamental here.” And looking back on it, those are usually the times I made a mistake.

Peter: One of the things that we teach in leadership and I talk about a lot in leadership, is an unusual combination of characteristics that I think you actually have in spades, and you demonstrate in the book. And that’s this combination of confidence and humility. You know, the sort of humility to say, “There’s a lot I have to learn” and the confidence that says, “Yeah. I’m 24 years old and I’m going into the White House, and I’m writing President Obama’s speeches.” And you need both of those. And the self deprecating humor in the book is part of that, that’s part of the humility piece, but there’s also a lot of confidence. And I’m curious to hear you talk a little bit about that. I don’t know if this is familiar to you, or you recognize it in yourself …?

David: Yeah.

Peter: And if you do, how do you cultivate both of those simultaneously?

David: Well, you know when I left the White House, I did a tour of the West Wing and met with as many people on the senior staff as I could, and asked them questions like that. I mean, sort of life advice questions, ’cause I figured, where else am I gonna get the chance to talk to 20 of the most successful people on the planet about just how to live and work in the world. And one piece of advice I got, or one thing that stuck with me. Someone on the senior staff told me, “You have to believe in yourself, which looks like confidence sometimes, but is actually a different thing.” And I think that’s true. Like, I think, anyone who reads the book I think can tell that I believed in myself in some fundamental way. I didn’t think, “Okay. I’m gonna find out that I can’t do the work.” I had my doubts, but I wouldn’t have been there if I thought, “You know what, I don’t belong here.” Or “If I work hard, I won’t belong here.”

But I didn’t always have confidence, and I think that’s important. And I wrote the book for a lot of reasons, but one of the things that has been nice is people saying, “Oh. I feel like that in my job where I’m 24 or 34 or 54, but it never felt like I had permission to admit it.” You know, to say “I think I can do the work, but it also doesn’t mean that I’m always confident about my work.” And I think …

Peter: Tell me a little bit about the difference between having belief in yourself, but not necessarily being confident.

David: So confident … To me the confidence is kind of that sense of every moment I’m doing exactly the right thing, and I don’t need to worry. And believing in yourself is thinking it will turn out okay eventually. You know, it’s also how I feel about things in general, right? I’m kind of a long term optimist, but I have no idea what’s going to happen in the short term. And I think that’s true as I was doing my own work as well. That I was fairly confident that things would turn out okay, but that didn’t mean they didn’t feel like they were falling apart. And you know, it was to me in the book, important to describe both of those things. That most of the time they did turn out okay. There was a time I almost set President Obama’s hair on fire, but I didn’t set his hair on fire, so that was a success. But I do think that the … Throughout I wanted to talk about …

The other, by the way. To me something that I feel like I learned from watching President Obama is that there’s a form of believing in yourself or confidence or whatever you want to call it, that is signaled by the ability to go back and say, “Hey, these are some mistakes.” And to think critically about your own role. To me a lot of the time, there’s that version of confidence that’s sort of like, “I think I’m the best all the time.” And I don’t think … That often is really more insecurity than confidence …

Peter: Right. I think that’s what distinguishes confidence from arrogance. So arrogance is, “I think I’m better than everybody.” Or “I think I’m amazing all the time.” And I agree with you, it comes from insecurity. But that’s not confidence.

David: Well, the way that I often think about it too is, to me these are issues of do you think you’re the best, or do you think you’re tied for first? And when I thought about speech writing in the Obama White House or in D.C, I definitely am not the best speechwriter, you know, was not the best speechwriter in town or even the best speechwriter at my level in town. But I think I was roughly tied for first, that I felt like I can do this as well as anybody. And then the rest of it is largely luck and being in the right place at the right time. And I think it’s important to recognize both of those things. And I think that was a sense of believing in myself, but also a recognition that like, “Man, this is pretty crazy that I’m here.” And you know, just because I think I can do this job doesn’t mean this is normal and not totally surreal.

Peter: Tell us a little bit about your speech writing process. How do you get started? What do you do?

David: Well, the speech writing process is really different for every White House. And it’s different for every principal. Because I started off writing for Valerie Jarrett, who’s the Senior Advisor to the President, and Bill Daley who was the Chief of Staff. Before that I wrote for CEOs and other leaders in the private sector as well as the public sector. And everyone has their own process.

For President Obama, we would usually get a topic about a week in advance. Generally it would be sort of “Here’s where he’s going. Here’s what he’s talking about.” And then we would meet with policy teams, and the goal would be to figure out what is he announcing? What’s different about this speech? And how does it fit into all the other things he’s said about this topic? Because by the time I got to the White House, you know, name a policy area. Education, infrastructure, whatever. President Obama had spoken about it multiple times. So it was about taking this body of work that already existed, and updating it for a new location, a new audience, maybe there’s a new inspiring story of someone we haven’t told. But trying to figure it out that way. And we generally have a week.

And we would do this combination of expert … You know, like I would sit with experts and I’d try to get as much information as possible into my head, and I would do my own research. And then we would send it to … The day before the speech … So I would send it to the Chief Speechwriter who would edit it to make sure that it was in the President’s voice and that it kind of just looked the way it should. And then it would go to about 30 different people who would … There was a list of about 100, but most of those 100 understood that unless it was important, they shouldn’t weigh in. So it ended up being about 30 people per speech who felt like, if something came up that was in their issue area, they would jump in with thoughts. And that could be somebody at the Communications Department with a turn of phrase, but it could also be someone in Education Policy who says, “That’s not as important as you think it is, but this other issue, this other thing the President’s announcing is the big deal. So talk about that.”

Peter: Which seems really smart because it’s to avoid those bloggers and news agencies who are going to look for every hole they can poke in order to discredit you, or say, “You left out this part” or “Why didn’t you include God in your Thanksgiving speech?” I guess sending it out to 30 people is almost like beta testing the speech and saying, “What vulnerability exists in the speech that people might jump on?”

David: Right. I think that is important too because to some extent as a speechwriter, as a writer, your job is to … It can’t be totally risk averse. Right? You’re playing offense a little bit. Because the most risk averse thing you could do is to have the President not give a speech. So you’re thinking about how do we achieve some …? You know, what do we get out of this? But you also do want people thinking about, “Okay. What are the vulnerabilities here?” And they don’t necessarily get to do the fun part, but they get to say, “Here’s where it could go wrong.”

And that’s something I saw as a White House, I think we did more and more often on all sorts of decisions, not just speeches, as time went on. It sort of have someone play a dedicated … You know, be the dedicated cynic, be the dedicated political opponents. Somebody to say, “All right. How could this backfire? How could we screw this up?” So that we have a sense of where the vulnerabilities are, and we do what we can to correct them or defend against them.

Peter: David, you talked about this early crush you had on Obama, right? How you heard him speak for 20 minutes and that completely converted you. And talk to us about what that was. For people who are listening, who again are senior level leaders in organizations and they’re interested in being inspiring speakers, what made Obama such an amazing one?

David: Well, I will say, if you’re a senior level leader in an organization and your goal is, “How do I have the effect on millions of people that Barack Obama did?” It’s gonna be tough. But I do think that the most important thing that, then candidate, Obama did, was he asked me and everybody else watching to be a part of this thing he was talking about. So some of it was what you would think of. That he was an inspiring … You know, that he could speak passionately and he would say things, like his arguments made sense, but they also had an emotional component. All the stuff that you would expect. I will also point out, it wasn’t just that he was a messenger, it was that his message and him and his persona fit perfectly together. So here was a candidate talking about hope and talking about change, and he was an African-American candidate who, when I saw him for the first time, had just won in Iowa where the electorate was over 90% white. And so he wasn’t just talking about hope and change, he was hope and change.

So I do think that’s important. You need to figure out a way that you as a messenger, personify the message you’re expressing. But the most important thing, to go back to what I said earlier, is he looked at the crowd of people and he was talking to the organizers, the field organizers in the crowd. And he said, “You represent that most American of ideals. That faced with impossible odds, people who love this country can change it.” But it was intentionally, I think, a broad way of speaking about it. He didn’t just limit it to those organizers. He was saying, anyone who loves this country, they have a responsibility to go do something about that. To make it better. And I think that’s way so many people, like me, immediately said, “Oh. I don’t just enjoy listening to him speak. I’m not just excited about him, I’m gonna actually go try to work for him. I’m gonna do what I can to help him succeed because he asked.” And I think that’s a pretty rare thing. A lot of times people don’t ask.

Peter: You know, it’s interesting. We’re doing some branding work right now. And one of the things that I’m learning about the branding work is, most people when they create a website talk about themselves as the hero. Right? They say, here’s what I’m gonna do for you. And what successful marketing does is the customer’s the hero, and you’re the guide. And what you’re describing is actually very interesting because you’re describing President Obama looking at you and the other organizers out there and saying, “You’re the hero. You’re the one who’s gonna make this change happen.”

David: Yeah.

Peter: But he might be the guide or the advisor etc.

David: Well, I will say … Right, I do think that the … Watching, you know being part of a big crowd of people when I was in college and I went to go watch Obama speak, and I was volunteering on the campaign a little bit. The feeling you got, you walked away with was not Obama’s great, it was that we are great. And his ability to do that. I will also say though, it came across in a way that wasn’t trite or condescending, because if he had just said, “You are all amazing and I’m looking forward to your vote in November” that would have been different. But you know, I think he talked about not just the sort of triumphs, but … You know and that same thing I was talking about before where we talked about the organizers, he talked about how they were working for little pay and little sleep, and how sometimes there’s days that don’t … You know, you work really hard and you don’t have a lot to show for it. So I think there were … The way that he talked was honest enough that it wasn’t just that it wasn’t … It didn’t feel like flattery, it felt like him recognizing the best possible version of you, which is a different skill.

Peter: Right. You talked about … And there’s a few times in the book, about really wanting to help President Obama be just a tiny little bit better at his job. And you know, I spoke at the beginning of this podcast about this idea of being a mid-level person and the kind of support that you can give in order to really be powerful in an organization. And I’m curious about that. What did you learn about how to be useful to the President of the United States?

David: Well, I think one of the things I learned, and it might not be the most inspiring, is that when you’re in an environment like the White House where the stakes are high and the pressure is always intense, not screwing up is much harder than it looks. So getting through a day without making a major mistake actually took a lot of work, and I would say a lot of talent, for myself and my colleagues. And I think that sometimes we don’t celebrate … You know, we celebrate brilliance much more than we celebrate competence, but sometimes, and particularly in some jobs, competence is really hard. And it takes the same set of skills that it would take to be brilliant in another job.

It’s different for example, than writing a book. Where if you write a book that is sort of, you know, doesn’t make anyone upset, that might be necessary, but it’s not sufficient. If I wrote a video taping that didn’t make anyone upset and you know, 500 people or 20,000 people saw it, that’s fine. I mean, it’s not ideal, but that’s me doing my job that day. So some of it’s just knowing what your job is in that way.

And the other thing I think that I learned about that role is to have a clear sense … You need to set your own goals in an environment like that because in the White House I generally learned there’s not enough time for everyone to celebrate or say thank you for every single little thing. So you need to know, “Here’s how I’m deciding whether or not I did a good job today.” And keep yourself honest. No-one’s gonna do that for you.

Peter: You tell some funny stories and maybe you can share one of them as an example in this question. But you’ve shared some funny stories about how tongue-tied you were with President Obama and how intimidating it is. And we’ve all experienced that. We’ve all been with people who we’re kind of intimidated by in one form or other for whatever reason, and our best selves seem to escape us in some ways and we don’t seem able to believe in ourselves or be as confident as we would otherwise be. I’m curious to hear one of those stories, which could be fun, and then also, how you found your footing. How that changed from that lack of confidence to the belief in yourself?

David: Well, so you know I write about the very first time I met President Obama. I had written this video for the Thanksgiving Day video address. It was, you know … I point out that if the State of the Union is on one end of the presidential speech writing spectrum, Happy Thanksgiving America is all the way on the other. But I was extremely proud and excited about this video, and we were about to start taping when the videographer, a woman named Hope Hall, stopped us and said, “Hang on Mr President, this is David. It’s the first video he’s ever written for you.” And President Obama looked at me and he said, “Oh. How’s it going David?” And I remember having exactly one thought in that moment, which was “I did not realize we were going to have answer questions.” And I’ve literally no idea what I said after that.

Like, I actually blacked out the first time I met the President. People would ask me, “Have you met him yet?” And I’d be like, “Yeah.” And they’d be like, “What did he say?” It was like, “How’s it going?”. They’re like, “What did you say?” It’s like, “I don’t know, I blacked out.” And so I … And I think … I later found that was not an uncommon experience. Like, far more famous, important people than I apparently also had that moment where they would meet the President, and then have no idea what they just said.

But one of the things I noticed about President Obama is that … There are also times in the book where I talk about him stopping us and specifically saying, “Guys, what’s up? Like what’s wrong here?” And I think that was important, that he recognized that obviously he’s an intimidating person just by virtue of who he is. And so he knew that it’s not enough to just assume that people will feel comfortable or to create an atmosphere where people feel comfortable, sometimes you have to directly give them permission. And sometimes you have to even go beyond that and say, “You know, I’m demanding to know what’s actually happening. Whether or not there seems to be an issue.” So he was … And it was usually like, if he noticed a look, like a uh-oh kinda look between me and some other staffer, those are the moments when he’d like, “Come on, guys. Like what’s happening here?” And I think that was … I wouldn’t say that’s how I found my footing, but I do think that changed, that sense of permission.

And I think some of it’s just repetition. That, you know, the first year I was doing the sort of wrangling of the jokes for the Correspondence Dinner, I didn’t feel like I had a lot of confidence about what I’m doing. But then after that, the more I did it, gradually you … So it’s amazing how quickly something can become, if not routine, at least somewhat normal.

Peter: Let’s talk for a minute about humor and being funny. And you know, that’s your thing, right? Currently you’re writing for a humor website and you’re the funny speechwriter, you talk about that in the book a bunch too. That’s your job now. That also feels like a lot of pressure to come up with a joke, right? And how do you continue to deliver? And humor on demand seems like it’s a real creative challenge. Is it for you? What’s your process, how do you deal with that?

David: So, humor on demand is definitely challenging. I was lucky when I worked in the White House. So I was sort of responsible for making sure that things didn’t go badly, and I wrote a lot of jokes myself, but we also had a big team of people pitching jokes as well. So every year my general sense was like, “I hope that I’ll have some jokes that are in the script.” And usually I had quite a few, but …

Peter: It wasn’t all up to you?

David: Exactly. That if for some reason I just … It was the year I just was in a total slump and couldn’t think of anything, I still think we would have had a good dinner. I mean, it’s one of the … Or as evidenced by like I left in early 2016, so I didn’t do the dinner in 2016. Nobody watching on [inaudible 00:25:03] in the room said, “Oh man, we really miss David.” And that’s good. To me that’s an important thing that the quality was the same.

When other organizations are trying to add humor, I think that there is … You need to have the time to write a lot of bad jokes. There’s generally I think, among people who are not funny professionally, a sense that funny people are just funny all the time. And the truth is, they’re funny more of the time, but that still means they’re writing … Or let me put it personally. If I’m sitting down and writing jokes, you know, it means I’m writing 10 bad jokes for every good one, or 20 bad jokes or more for every good one.

Peter: I want to just underscore what you’re saying here, because I think it’s really important. I think we live in these cultures of efficiency. I feel this pressure when I write also, which says, “Okay. You got an hour, you gotta write something.” You write it, you don’t want to waste any words, you don’t want anything to stay on the cutting room floor, and you have to be efficient and productive. And actually to be creative and to be productive requires in many ways that you be inefficient, right? And that you write 30 jokes, four of which are really good.

David: Right. Right. And I would even say it’s almost … You have to know what the goal is, right? If the goal is to just have something that exists, then I wouldn’t take the time to do the 30 jokes and come up with four that are really great, ’cause it needs to exist. And when we were at the White House and you had an hour to turn something around, you did your best, but you recognized that that’s all you can do. If the goal is to do … Let’s say with humor, if the goal is to say, “All right. We want something that is truly, legitimately funny, like really great.” Then the only efficient way to do it is to take that amount of time. You know, you can’t be productive and … You’re just creating something that is more, you know, it’s … Right, like the difference between kind of mass producing something and creating something handcrafted and unique. And that just takes more time.

And I think the other … One of the ways to shorten that length of time is to have people to run stuff by, that collaborating, or at least having someone to bounce ideas off of, means that you’re not responsible for writing and then rewriting everything in your own head, which can take a lot of time.

Peter: David, thank you. The book was great, this conversation is great. We’ve been speaking with David Litt. His new book “Thanks Obama: My Hopey, Changey White House Years, A Speech Writer’s Memoir”. It’s both a great glimpse into some of the things that we’re talking about around working in an executive office and the kind of contributions you end up making and how. It’s also a really endearing and interesting look. As you said, there’s not a lot of 25, 30 year olds who are writing memoirs about being in the White House. So it’s this very different perspective from a different lens level about what it’s like to work in the White House and I learned a whole bunch of stuff from it.

Thanks so much for writing it, and thanks so much for being on the Bregman Leadership Podcast.

David: Thank you. This was really fun.


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