The Learning Leader Show With Ryan Hawk - 499: Cody Keenan - Working With The Most Powerful Person In The World, Taking Big Risks, & The Art Of Speechwriting

Episode Date: November 14, 2022

Text Hawk to 66866 to become part of "Mindful Monday." Receive a carefully curated email from me... Each Monday morning to help you start your week off right... Full show notes at www.LearningLeader.com Twitter/IG: @RyanHawk12    https://twitter.com/RyanHawk12 Cody Keenan has written with President Barack Obama since 2007, working his way up to chief speechwriter. He's been named the "Springsteen" of the Obama White House, even though he can't play an instrument, and Obama calls him "Hemingway." His first book, Grace, became an instant New York Times Bestseller.  Notes: The use of productive paranoia. Cody said, "I was so afraid to fail that I would do anything to succeed." – We can use fear as fuel… Storytelling – As a speaker, it is our job to help the people in the audience see themselves in the place of the hero in the story. When you're preparing for your next team meeting or town hall address, think about that and how you tell the stories that you do. Singing at the Eulogy in Charleston - If you want an A+ performance, you have to choose to go for it. You can get a B by playing it safe, but you won't perform with excellence unless you have the courage to go for it. In less than 10 years, Cody went from mailroom intern in Congress to chief speechwriter in the White House. My goal is to "write a speech that sings."  'In less than 10 years, I went from mailroom intern in Congress to chief speechwriter in the White House,' President Obama said he relied "on Cody not just to share my vision, but to help tell America's story." "He's a brilliant writer. He's relentless." The first speech Cody wrote was for Senator Ted Kennedy. Right after President Obama's 2004 Democratic convention speech that put him on the map. You write: "To see someone else speak words I'd written sent electricity right up my spine and out my hair."

This episode is brought to you by one of my favorites. It is Storyworth. Storyworth is an amazing gift for you and your loved ones. Essentially what it is, as you sign up for Storyworth, and they help you supply a loved one with a question a week. So if in my case, I did this with my dad, and Storyworth would send him one question per week, and he would answer them and sometimes even add some cool pictures. to make it more visually appealing to go along with his amazing writing.

And then at the end of 52 weeks, Storyworth puts this together in a beautiful book, which I now have on my bookshelves at home. Along the way, I also got to read my dad's answers. So this is something that my family will treasure forever. He actually printed a number of copies and gave them to each of his kids. I would highly encourage you to do this. I even got to ask some of the questions each week for Storyworth. So to take advantage of this amazing offer that they've put together for you,

go to storyworth.com slash leader. You'll get $10 off your first purchase. That's storyworth.com slash leader. Welcome to The Learning Leaders Show, presented by Insight Global. I am your host, Ryan Hawke. Thank you so much for being here. Text, Hawk to 66866. become part of Mindful Monday. You along with tens of thousands of other learning leaders

from all over the world will receive a carefully curated email from me each Monday morning to help you start your week off right. You'll also receive details about how my book, The Pursuit of Excellence will help you become a more effective leader. Text Hawk to 6686. Now, on to the night's featured leader. Cody Keenan began writing with press, President Barack Obama in 2007, ultimately becoming his chief speech writer in the White House and his post-presidential collaborator. He now teaches speech writing at Northwestern University and he was named by British GQ as one of the 35 coolest men under 38 and a half.

Interesting list. He's also the author of the Instant New York Times best-selling book called Grace. During this conversation, we discuss why all leaders should have a writing practice. Then the art and science of writing and performing a speech. Then how Cody went from a mailroom intern to chief speech writer for the president of the United States in just 10 years. So many great anecdotes and stories as well as useful ideas for how to be become a better writer, a better speaker, and build an amazing career.

I think you're going to enjoy this one. Ladies and gentlemen, it's Cody Keenan. Cody Keenan. Great to have you here on the Learning Leaders Show. Welcome. Thanks, Ryan. It's going to be with you. So I want to jump into the middle of your career, and then we're going to go in a little bit more sequential order. And so let's go to 2015. You're working on an important speech for President Obama.

This is the State of the Union address. and you turn in the speech to, I read this, you turn in the speech to President Obama eight days early, which apparently is a record. Normally, it's more up to the wire. And I had read that he summoned you to the private dining area and the White House to talk to you about this. Can you tell me what happened next? Yeah.

And to give you a little background on it, I mean, you know, the state of the union address is something that every. speechwriter dreams of writing until you actually get to do it because it's awful it's the laundry list you have to jam everything in there everybody's coming at you with their policies and whatnot so i felt like i had and you ruin your christmas doing it every year i ruined my family's christmas four years in a row um so i felt like i had something that was in in the best shape of one of these had been in eight days out you know it was um kind of as as as pure as a state of union you can get everything was in there it all made sense

It flowed really well, which is difficult in these things. And so, you know, I expected to hear from him right away. And a full day goes by. And now I'm starting to freak out a little bit. And so his assistant Fario calls and says, hey, can you come upstairs? Because my office was underneath the Oval Office. So I go up and he's not sitting in the Oval, which is strange. I'm like, where is he?

She said he's back in the dining room. He wants you to go in there. He said, okay. So I go back in there. And all I want to know is whether the speech is good or not. I haven't even shared it with anybody else at this point. And he takes his sweet time. He says, hey, brother, sit down.

So I sit down. He's eating, you know, he eats like a, he's monkish in his eating habits. It's just, it's chicken, it's vegetables. It's a little like quinoa or something. So he's munching on a carrot stick. And he goes, how you doing? I tell him I'm fine. And I'm just like, enough with this small talk, you know, let's like get to it.

So finally he says, you know, I think we're the best shape we've met in eight days out, this far out. And so everything my body relaxes. And then he says, but, and I tens up again, he says, we have eight more days. So let's make it better. Here's the thing. Everything is in here. Every sentence says something. Every word means something.

And I just tell them, yeah, that's, you know, that's what these state of the union addresses are. He says, no, no, no. It's what I'm trying to say is the entire speech is up at a 10. And I need some of it down in eight, six, four. I need some emotional moments and some quiet moments. And I'm sort of picking up what he's putting down, but it's still the state of union dress just isn't one of those speeches. And he says, let me put it another way.

You ever listen to Miles Davis? And I said, not really. I wasn't really into jazz. And he said, well, here's the thing about Miles Davis. It's the notes you don't play. It's the silences. It's the space between. That's what made him so good.

So I want you to go home tonight. Don't do any work. Pour yourself a drink. listen to some Miles Davis and come back here tomorrow and find me some silences. And then I got it. I actually did listen to him and listened to some Miles Davis and came back in and, you know, as much as you can with the State of the Union made it a little lyrical, brought it down in some parts, gave it some pauses and silences.

And, you know, no State of the Union addresses ever going to be carved into a memorial, but that one I think was pretty good. I think it's a rare quality in a person that they can be both the great writer and the oral orator and the teacher, right? Like, have this deep understanding of highs and lows. It's like you listen to a concert. Sometimes they do have to play the quieter songs because it was just at a 10 the whole time.

You'd probably be exhausted 30 minutes in or 40 minutes in. But I don't know if I could ever put that into words. When you walked back to your office after that moment, what were you thinking? Mostly I was relieved that I wasn't going to have to rewrite an 8,000 words speech. I was actually thinking, I was a little embarrassed because that is, I mean, it is something I intrinsically knew about speech writing, that it is also a performance. And I just, because the state of the union addresses its own unique beast, I had just lost sight of that in my desperate attempts to get everything in there needed to be in there. But he's got, he's got two skills that most speakers don't, and I've worked with a lot.

one is he's an active writer and he's actively engaged in the process you know i i haven't worked with many other people who will dive in with their pen and just edit the heck out of everything and it's because he's a writer first and foremost i mean you know he has he has told me a million times that he wrote the o-four convention speech himself that he wrote transcripts my father himself like i know um so that's number one very helpful because he is now by the time he gets up to speak he has internalized everything you know the flip to the flip side to that is Donald Trump used a teleprompter too. And when he

did, he actually exposed himself as never having read the speech before. Just as an example, I remember early in COVID, he said something like people get a flu shot every year. Not everybody, not a lot of people know that. No, we all know that. You didn't. And you just

prove to everybody that you didn't know that. So, you know, like I said, it's kind of like a sheet music when it goes in the teleprompter. And You know, I said there were kind of two things that made Obama unique. The other is the performance aspect. You know, delivery is not just reading a speech.

You are actually performing with your eyes, with your body, with their hands. You're conducting an audience. And that's a powerful thing. You know, you don't ever want to let a captive audience go to waste. But when you are writing a speech and then when you're delivering a speech, you're thinking about how you can actually conduct the audience. You can move people to laugh, applaud, cheer, boo, even though I don't recommend it, and ultimately move them to action.

So being able to work for him was always such a blessing because he was so good at both parts of it. There's a, I think a lot of people that are interested in this show, Cody, that are like an SVP at a Fortune 50 company and they give regular, let's say, town hall addresses, even sometimes weekly addresses to the senior leadership team. And I think they could benefit from hearing from one of the greatest, speechwriters of all time that I'm fortunate to have here today of how they could be better at this. I know it's different than being the president of the United States, but there are some

similarities to giving a great presentation to making your Monday morning address to your team, a really excellent one as opposed to the boring ones that most of them are. What pieces of advice would you give to that person who's preparing for their Monday speech or preparing for the quarterly town hall where they're going to address a few thousand people maybe about their company. What are some ways that they could do that really well? Be direct, be colloquial, be concise, be engaging. I mean, all that sounds pretty obvious. I'm going to give myself in a little bit of trouble here because I work with, I have some corporate clients now. I'm at a speech writing firm called Fenway. And a lot of times,

you just need to ignore your comms team. That's the part that's going to get me in trouble. There is, there's so much fear involved in corporate communications in a way that we were fortunate never to have at the White House, but there's, there's a fear of what you can't say, you can't say this, you can't say that, you can't say that. And then there's also this kind of, this habit to cling to things that you think you're supposed to say. He or she has to say this, has to say that.

That's not always true. Just throw that all out. You know, you should approach. I know that you are beholden to shareholders and the board and you don't ever want to rock the boat, right? That's where all this fear comes from. But every speech should tell a story, even if it's just a quick message to your own employees, a story with a beginning, a middle, and the end. And it should be conversational. It should sound like, you. you, it should be a speech only you can give. And if you're getting twisted around the axle with he or she has to say this, he or she can't say that, it often makes a speech kind of a mess. So you want it to feel normal. You want it to be normal. I mean, there's this, you want to be authentic, which sounds like such a cliche, but a lot of comm shops, and this was true in the White House too. And policy people and lawyers that we always had to deal with, if you are constantly worried about what you can or can't say, that just wears away as your authenticity.

You know, like being authentic is actually very easy. You just have to get rid of your fear. Why do you think that fear exists? I'm with you. I've been in those meetings in the seats watching the person. Like, is it just, I don't want to get fired? I mean, why does it exist? I think it's simply a fear of I don't want to I don't want to cause a problem I don't want to

cause optics problem I don't want to have to do any cleanup and generally you that's not something you actually have to be afraid of you know I remember the the few times in the White House where everybody get all twerked up about you know can Obama say this can Obama come out for marriage equality that landed with like just a pillow soft whimper because the country was already ahead of Obama on marriage equality. He was actually behind there. And for all of the, you know, everybody's just kind of twisted in a knot, how is this going to be received? How is it going to play? It played great because, you know, by that point, most of the country was in favor of marriage equality. That's just one of the first examples that came to mind.

But it, it, usually those fears are unwarranted or overblown. And people appreciate it if, my first instinct to say just tell the truth, but one of the most radical things in politics is when you just tell the truth that everybody already knows, but most people have been too afraid to say. And it doesn't actually, it feels like it requires a lot of courage to do that, but it really doesn't, you know. And so I think people gravitate to leaders, whether in the public or private sector, who come across as fearless,

who come across is in control and self-confident and know what they want to say and why. And that doesn't mean you have to push the envelope or say something provocative. You know, again, oftentimes it feels provocative. If somebody says something we all already know, we've just been desperate to hear from our leadership. That's what stand-up comedians, the best ones do that so well, right? They're able to bring voice to something that you were already thinking and they do it in a funny way. And I think leaders can learn a lot from watching the best stand-up comedians because they do that. You also have said that every speech should tell a story.

And I think of my favorite bosses and coaches that I've either played for or worked for. And they were really good at this. They may open with a compelling, interesting story and then weave that into how that applies to me sitting in that seat or to how I could take inspiration from that to go do my job. when you as a speechwriter, how do you think about storytelling? How do you how do you put, like write them in? Where should they go? Do you open with them, close with them?

Like, talk to me about storytelling within speechwriting. There is no way you could have known this, but your timing is perfect. So I teach speechwriting at Northwestern University, and this week's assignment is storytelling. And I tell them all, you are running for President of United States. But the purpose of this assignment is I want you to take a story out of your own life or it can be somebody else's who you know or have met tell that story but but then but you need to do it in a way that connects to everybody in the audience so that it's actually a story about something bigger and one of the best examples of this is uh barack obama's 2004 convention speech

the one that rocketed him from anonymous state senator to global megastar in 17 minutes he told his story the story of uh the son of a a Kenyan, a black man from Kenya, a white woman from Kansas, barely knew his father, grew up all over the world, raised by his white grandparents, and told it in a way that made it seem like the most quintessentially American thing possible, even though this is a guy who is very different

from the typical political leader that you see on stage, he immediately said, in a blunt kind of off-ramp, in no other country on earth could my story even be possible. And then he's off and running, telling the American story. And now he has just woven himself into it in a completely opposite way from the way most leaders do. I mean, most of our presidents, well, all of our presidents for him were white guys, but most of them came up through prep schools and Harvard or Yale and had people around them forever. And here's a guy who just, you know, a week before that speech was pumping his own gas. And he comes across as just like the most American guy possible.

So there are a couple different ways to tell stories. You can tell your own if people don't know it. You can tell somebody else's. A lot of times in the White House, we took stories out of letters to the president, like letters of people actually wrote him and wove those into speeches. But you're not just doing it to tell that story. You're doing it to connect to something universal to you're kind of basically telling the audience, I am one of you, without having to say it.

I think, too, back to that same 2015 state of the union address, that was the only one where we didn't work in stories of a lot of people who were sitting up in the first lady's box, you know, at the speech. We just used one. And we told the story of this woman named Rebecca earlier who had written a letter to the president. And we kept coming back to her throughout the entire speech. And that was an implicit way to connect with the audience at home. And rather than just say, I am fighting for you, I understand you, I feel your pain. He told the story. of this woman that a lot of people could see themselves in and that's an even more powerful way to connect to your audience and they you know that that was the highest testing to say the union address

we ever did afterwards and it was because he told the story of this woman that a lot of people could see themselves in they'd be watching on TV and say i know that woman i am that woman that's my life you started as an intern and in congress and 10 years later you're the chief speech writer to the of the United States. That is an insane career arc that seems almost impossible. How did you do it? There's, I mean, on the one hand, there's obviously tons of hard work in late nights and weekends, but there's also a ton of luck and privilege involved. You know, just the mere fact that I could intern in Congress right out of college was because I had parents who could help me with the rent for a couple months, right? So that immediately gives you a leg up.

And then a lot of it's just being in the right place at the right time. You know, I had a mentor. I worked for Ted Kennedy right out of the gate. And I had a mentor, a woman named Stephanie Cutter, who was his communications director. She went on to be communications director on the Kerry presidential campaign in O'Boh. And a young speechwriter on that campaign was named John Favro. And she connected the two of us early in the Obama campaign and we hit it off right away. But without that lightning bolt, who knows where I am right now?

I have no idea what I would be doing right now. So it's always hard work and luck and not being a jerk. You know, those are pretty simple rules, work hard and don't be an a hole. But there's a lot of luck involved too. I read that one of the first speeches, maybe the first speech you wrote was for Senator Ten Kedony, and it was right after President Obama's 2004 Democratic Convention speech. And you wrote, to see someone else speak words I'd written sent electricity, write up my spine and out my hair.

What's that like? When your words are being spoken by somebody else on TV, on stage, or obviously in the biggest stages in the world, what was that like at the beginning? And then how did you grow into that role and to eventually be chosen by the most powerful person on the planet to write for him? Yeah, it's amazing.

Sorry, you're probably hearing my daughter crying in the background. But it was kind of like that. It was kind of like crying the first time I saw somebody give a speech of mine. I probably felt like the first time somebody gave Eddie Van Halen a guitar. You've suddenly got this power that you didn't know you had before. And I still have the first speech I ever wrote for Ted Kennedy. He was nice enough to sign it afterwards and say,

welcome to the speechwriting team, even though we didn't really have a speech writing team. Just everybody kind of wrote. And then I got to write a few more for him. But that first one and those successive ones, they weren't very good. I'll go back and look at them now. like, I would love to rewrite that speech now. And I still feel the same way about a bunch of speeches I wrote for Obama in the White House.

I'd still be editing my book if the publisher didn't have a deadline. Because all great speeches are, you know, 90% rewriting. But you, I got better over time through hard work, through practice, through, you know, John Fabro became a mentor too. He's still one of my best friends of the world, but he was patient with teaching me how to write for Obama. And that's, it's always, writing for every person is different. You need to get inside their head, understand their worldview, because it's even more important

than what they want to say is why they want to say it. So I had the privilege of leaning on John for a long time until he ultimately left and I took his place. It was interesting. I read a lot about you guys when you were in office because you were so young. And I think, I mean, that was a big part of the story. Young, like good looking guys, amazing writer. Axelrod calls you the word smiths. And I love the, I love the, how hard it is to get the thoughts out of your mind down on the page. That's why all leaders absolutely must have a writing practice because it creates clarity of thought. You don't fully know what you believe until you're forced to get those words out of your head down onto the page. And so to have these, the most powerful person in the world is surrounded by these 20-some-year-old guys who are writing a speech.

beaches blew my mind. What was it about the youth? Like in, and he could have chosen any person in the world, any group of people to be on that team. And it's Favro and it's you and these young guys. What was it about your youth that it seemed to be, or was it just the work and you just happened to be young in addition to the work being great? What was it that, that I think he liked in you guys? Well, we were much better looking 15 years ago. But, but, but, but, But politics is often a young person's game just because the hours are so grueling. You know, we're not digging ditches or working with our hands or anything like that. But, you know, aside from typing, but that's not what I mean.

But you work straight through weekends. You pull all-nighters. You have to. And it doesn't pay very well. You know, my first paid job in Congress was $18,000 a year. That's why you live with six people in a townhouse, you know, and drink cheap beer and search for happy hours with free food. My first job in the White House paid $45,000.

You know, and so you can be in the most powerful place on earth. And for the first two weeks in the White House, I had a negative bank balance. And another speechwriter on our team named Adam Frankel was quietly buying me lunch without telling anybody. And it's, you know, it's not like I was living on the streets or anything. It's just I needed that first paycheck to come in to cover it. but it's a young person's game in terms of hours and pay.

But the drawback to that, actually, is that we didn't have all sorts of life experience yet. The only lives we knew were we all basically grew up as relatively privileged white people, and we were 27 years old. And part of being a speechwriter is having a deep sense of empathy, being able to understand your audience, walk around in their shoes, And there are limits to that. You know, all of us are really well read because that makes you a good speechwriter too. But that was actually a net negative for us to all be young and not have all that life experience.

But that was his choice, though. So why was that? Is it because it was before you started, before you got married, before you had kids, before you had, you could basically dedicate your life to the job. and that was attractive in addition to being a good writer. I mean, because like I said, you could choose pretty much anybody. Yeah. And he chose you guys. Yeah, we all shared a worldview, which makes a big difference.

You know, you don't want a speechwriter who is diametrically opposed to you, not just in policy, but in the way you see the world. And the way we saw it was we thought politics was a force for good, a force to change the country, a way to, if you, if you, if you rally enough people to your cause, you can change things for the better. And we all viewed, a lot of this came from Obama to just rubbing off on us,

but we all viewed, you know, our mission as Americans coming straight out of the founding documents was to make this country more perfect. And I fully bought in, I happened to be on the floor in 2004 in Boston when he gave that speech. And I was fully bought into the idea

that our mission as Americans is to make this country a better place. And what makes America exceptional and different from other countries is that America can change. We are not built on any bloodline or religion or aristocratic background. We are a beautiful mess of all sorts of different people. And it's incumbent upon us to make sure not just everybody's created equal, but everybody's involved in this and this country works for everyone. And that all sounds preachy, but it's a way of answering the question,

which is we all bought in. We all shared a similar worldview to him. And that just made our collaborations that much better. I was looking for an uncommon common commonality between you and me. And one of the things I found after a lot of digging was the fact that you played high school quarterback. I played quarterback in high school and college and a little bit after college for a little bit. So we have some of that sense of what it's like to walk into a huddle with ten other guys looking us in the eye, having the call play confidently and then execute over and over and be the hardest working guy.

And the team, I would imagine. What did you learn from your days playing high school quarterback that helped you later on in your career? Great question. Nobody's ever asked me that. I think even though we have that commonality, our difference I imagine is that I wasn't very good at it. My team was lousy.

We were three and eight my senior year. You know what you learn is this is another thing that I'd love to go back in time. I'd love to go back in time and play quarterback again, knowing what I know now. Because I was still, you know, I was 17 and I didn't have a ton of self-confidence. You would assume that a high school quarterback has tons of self-confidence, but I was constantly afraid, not of getting hit or getting intercepted, but the fact that you've got thousands of people watching you. And you're the one who touches the ball every single play, and it's all on you.

And, you know, fortunately, we ran the wing T, so we had an amazing rushes and attack. We had three running backs who just kicked ass. But so what I learned from that was, that's what a lousy offensive line who had me on my ass all the time. But what I learned from that is trust. You have to be able to trust everybody else. You have to be able to trust your line. You have to be able to trust your receivers to make that cut and be there when the ball is there. But it's also a two-way street.

They had to trust me in return. And then, you know, there were plenty of games where I just played piss poor and didn't earn that trust. But so it's always an ongoing thing. And it ties directly into when I became chief speechwriter right after the second inaugural. I didn't fully trust my team yet, even though I'd been working with them for four years. It's an alleviate a completely fresh slate. It's not entirely that I didn't trust them either, but I felt this crushing, inner need to prove myself

because you're replacing somebody like John Favreau who was a celebrity in his own right by that point and I was very worried that people who paid close attention to politics would notice some kind of slip off in the quality of Obama's speeches and so I just wrote too many of them myself and I actually ended up

in Walter Reed Hospital in April 2013 with about a hypertension because we had just come through a week where it was the Boston Marathon bombing it was background checks were blocked by Republicans in the Senate. We were just writing all sorts of crushing speeches on all sorts of different stuff. And it was my deputy guy named Terry Zouplatt who, you know, I came out the next day.

But he said, look, man, this isn't going to work if you don't let us write. If you don't trust us to write, you know, we've been working together for four or five, six years now. You know what we can do. And I actually needed to hear that. And, you know, part of good leadership is delegating and, you know, trusting the team around you. Yeah. No doubt.

I can imagine how hard that would be, though. Specifically, I think about writing in someone else's voice, especially for a prolific writer, which is not, I don't know if that's the norm for the president. If I think back, like how many of them are actually world-class writers, not many. So that compounded with what I think would be the challenge of writing not in your voice, but in his voice, what's the mind space you got to be in to say, okay, this is how he would deliver.

This is what he wants to say. I read that you said you thought and cared most about impressing him, the person your boss, the person you're writing for, the president. What's that like writing not in your voice, but in his? I've always liked in writing for Barack Obama, called it a wonderful struggle. You know, it's wonderful because he's such a talented writer.

And you know that if you know that, If your draft isn't where it needs to be, he can come in and take it to a better place. But the struggle is that we wanted to impress him every time. We wanted to get him a perfect draft every time, even though that's not what he was asking for. He viewed speech writing as a collaborative effort, and he just wanted something he could work with. Learning to write in somebody else's voice is probably the hardest, most time-consuming part. Because you're not putting your own words out there. They're his.

It's what he could write if he had the time. Honestly, I think he would have always preferred not to have speechwriters, but there was just no time for him to write 15 speeches for himself every single week while running the free world. There are a lot of similarities actually to what I said about being a high school quarterback. I wish I could go back in time and be a quarterback again, knowing what I know now. I also still wish I could go back in time and be chief speechwriter again knowing what I know now. because I was, much like I was on the field, I was afraid a lot, even though, you know, we started this podcast talking about how you have to cast off that fear. But I was always afraid of letting him down, writing something that was subpar. You know, I always had imposter syndrome, too.

Like, I never felt like I deserved to be there. So there was also this fear of being found out as a fraud. And, you know, fortunately, I had someone like my wife around me and she worked to the White House too. was like, if Obama didn't want you to be Chief Speech Writer, you would not be Chief Speech Writer. That much, I promise you. He would have gotten rid of you right away. He wouldn't have hired you in the first place. And the country knows that you guys are turning out this great stuff, but and yet every single time you are given a new task, you're terrified.

I actually think that fear, and I spoke about this in a commencement address once, fear can actually be a powerful motivator. you know like people always say you shouldn't be afraid to fail i disagree with that i think you should be so afraid to fail that you will do anything it takes to succeed you know i was always so afraid to fail him and the american people and the people whose stories were telling that i would pull all-nighters to make sure the speech sang you know i would i would work weekends to make sure a draft saying um So I actually kind of used fear as a tool at times to get better. Jim Collins writes about being productively paranoid. And I identify with that so much.

I sense that's you. Like just it's because when you say you're paranoid, that's not good. So you add on productively paranoid when it comes to your work. I feel that way before speech while writing, while podcasting of preparing of productively paranoid, I think. like that this this I get one shot like I want to make this thing I love how you say I want to make it sing I think that's a girl I'm going to use that but I got to make this thing sing I want to make this this as excellent as it can be in that fear of screwing it up the fear of failure I'm with you man

especially because it comes from within it's not coming from a boss it's coming from within you of saying I'm going to use this fear as my fuel in a way to work incredibly hard to make it as good as it could be. That's absolutely right. And, you know, what's important is that Barack Obama wasn't the one who made me fearful. You know, he was never, he was never the kind of boss who would say, give me something good or get out of here. You know, I tell the story in great detail in the book about the Charleston eulogy,

the Amazing Grace eulogy. And I spent all week kind of that week, twisted a knots over this eulogy. because it had a racial component too, which is always difficult to write about. And Obama, you know, he didn't give me anything to go on. And he's been, he's been, he spoke about this on a podcast that he did where he gave me no guidance. He just said talk about race, talk about guns, talk about the Confederate flag, and wrap it all up in grace. And you're just like, I don't even know where to begin with that.

So I gave him a draft that I knew was subpar and I gave it to him the night before the speech, which was probably two or three days too late. And I told him as much. I said, look, I think the first couple pages are good. The second couple pages need, they need you. And I'm sorry. And he said, no problem. I'll look at it.

I'll make some edits. I'll get back to you tomorrow morning. He called me back to the White House that night at around 11 p.m. And so I went back in. We were sitting in the residence. And he had made a bunch of edits to the first two pages and said, you're right about those. They're fine. But the second two pages he had just drawn one line through each, which he had never done to me before. And I'd had three days to do this draft. He rewrote

it by hand in three hours. It handed me three yellow legal pages with just his neat handwriting on it. And it was beautiful. And I actually apologized to him for the first time ever, you know, because I felt like I had let him down in a really important week. And this is what makes him unique as a boss, he put his hand on my shoulder and said, look, brother, we're collaborators. You gave me what I needed to work with here. You'll see a bunch of your work in what I did. I just rewrote it a little bit.

And when you've been thinking about stuff like race for 40 years, he'll know what you want to say too. And that's a really important thing. He could have just said, you screw this up, you know, do better. Or even worse, he could have excised me from the equation. He could have given the edits to the chief of staff or somebody else. else to then hand to me, which would actually make me feel even worse. Instead, he took the opportunity to lift me up and walk me through what he did and make me leave there, not feeling like a failure,

but actually feeling pretty good about myself, even though I had to go spend three more hours kind of working his stuff into it. That's just the kind of boss he was, and it makes a big difference. What a great lesson for leaders. Like, think about that. I think sometimes you get like these expectations that maybe aren't realistic, which I understand because we want to strive for excellence. But to know how you have such a valuable team member, like, hey, brother, we're collaborators. This is how it goes. The world's messy people. To get to the end point, it's a bunch of squiggly lines.

You know how it is. It's never just a straight, easy route. And I think that's what I loved. So I was reading, I was going to read a talk about this book. It's called Grace. And cool picture on the cover, by the way. But what's inside is even better because obviously you're a great writer and a great storyteller. But just the combination of weaving these anecdotes and stories within this 10-day period.

I mean, you're there for the whole time. He's their chief speechwriter for four of the years. And you chose these 10 days. What made you choose these 10 days? It's the sheer magnitude of the events that happened in these 10 days. You know, when I was writing this book, I told people what I was thinking about. And they were like, dude, I remember all that. I did not remember it was all in the same week.

You know, somebody once wrote way before the book that it was just, it was too implausible for an entire season of the West. Remind me that, remind us of the, of what are some of the big events over the course of these 10 days. Yeah, the book begins with the White Supremises Massacre in Charleston, South Carolina, and unfolds through, the president has to make a statement about it. The families of the victims forgive the killer at his arraignment, which was extraordinary. You start to see Republican governors in the South quietly bring down the Confederate flag over public spaces. And all the while, we're grappling with whether or not to give a eulogy.

And the president and I did not want to do one. I didn't want to write it. He didn't want to give one. And we're also preparing for the Supreme Court to rule on Obamacare and marriage equality that week. you know, there's a very real chance that they could tell millions of working Americans, sorry, you don't get health insurance. They could tell millions of gay Americans, sorry. You don't get to get married like the rest of us, your second-class citizens. And then Obama goes and gives the amazing grace eulogy and comes back to a White House lit up like a rainbow. And that's all

in 10 days. But it's more than just the enormity of the events. It's what they all say about us as Americans. You know, every single one asks us, do we actually believe that all of us created equal. Are we going to stand up against white supremacism and bigotry? Are we going to make sure that everybody who works hard gets a fair shake? Like, are we going to do anything about gun violence? You know, are we going to do anything about the fact that, you know, African Americans have to walk past Confederate flag every day to get to work? Like, there were all these questions that we just haven't grappled with over our, you know, 240-something year history that all, like, were thrust upon us at the same time.

And over those 10 days, we answered them all correctly. It was one, it was just like this remarkable little burst of progress in a country where our story is bursts of progress followed by backlash to that progress. And it just felt alive in real time. Democracy felt alive in real time. And it was just something I had to write about. How about the singing? What was, what went into the singing at the end, which is, I'm thinking about.

this. The ultimate, man, you could really mess this thing up, this beautiful moment. This, I mean, it was from tragedy, obviously, but great eulogy. All right, I'm going to go for it. I'm going to sing. What went into that? What did you talk to him about before, after? What was that like? It was all his idea. You know, that's, that's, that's not the type of thing a speechwriter can write. You don't just write in the draft, sing here. And it as part of his rewrite the night before, he, he, I had had the phrase, amazing grace in the speech. And that's basically where he tore it up. And he built the structure of the back half around the lyrics to Amazing Grace, which was beautiful and its simplicity. And one of those

things I kicked myself for not thinking of. And that morning, Friday morning on day 10 of the 10 days, he went out of the Rose Garden and spoke about marriage equality, which Supreme Court had just found a right to in the Constitution. And five minutes later, we're on the helicopter heading to Andrews Air Force Base to fly to Charleston. And he was still working on the speech, because he is able to just shift gears instantly. He hands it back to me when we land on the helicopter and says, you know, if it feels right, I might sing it. And that hadn't occurred to me either.

And I just kind of looked at him and I was like, you do you, man. Because he's got a deep background with the AME church. He knew they would be there to catch him. But it's still, he wouldn't be alone in singing. But it's still, it's both a big leap of faith to do something like that, to sing in public, period, let alone when you were president of the United States. but it was also kind of a liberated

fearlessness that he had earned over seven years in office. And he's talked about this a little bit where you can feel like a lot of the White House can feel like you're going over the Niagara Falls in a barrel,

but you survived. And there's something that comes with that. There's kind of this liberated fearlessness where you know to mix metaphors, he's kind of an aging basketball player, right? when you can't necessarily dunk anymore, but you know that you can hit the shot when it counts.

And that's sort of what I saw when he stood up there and saying it. It was kind of a fearlessness. I think what it taught me as a leader, if you want an A plus performance, you have to go for it. Now, that also puts you at risk. It puts you at big risk for potentially ruining what, what led up to that was a was an a or an a minus and i think there's a lot for all of us to to learn from these moments like whenever you look in history of of these these times like that

was when the singing of that happened that we all remember and if you if you've forgotten go back and google it and on youtube it's it's awesome it just shows to get the a plus you got to be willing to go for it and i think as leaders that's something for us to think about during our next town hall during our next big speech or even just a one-on-one like are you willing to actually go for it and not play it safe or not say you know what I'm gonna put in I'm gonna do a solid B plus today you know like no I think today's an A plus day but to get that a plus I got a I got to risk it a little bit and that's a that's a that's a really cool thing to think about to internalize for us as leaders yeah I

Not many leaders would have stepped up in saying like that, you know. And it's interesting to think about, too, I still don't know. I don't know if you would have done it or not had we lost both Supreme Court cases. You know, if you're coming off that morning, having lost not just on the biggest domestic achievement of your presidency, but the fact that millions of Americans are going to lose their health care, you're coming off, millions of Americans being told they can't get married. Does he still sing? I don't know.

There's an argument to make that it's all the more important to sing. We actually had debates in the White House, not heated, but about lighting up the White House in rainbow colors that night. That same day is the eulogy. And somebody actually asked, you know, what do we do if we lose? Do we keep it dark? And a young gay man on staff actually said, no, that's when it's all the more important to light it up and remind people that they sold a place in this country. I have something on a little bit of a less serious, although it turned out to be a great moment for you, about your role. resilience. So earlier in your time working in the White House, I'd read that you had asked a fellow

colleague, a member of the Obama White House, who's on the research team, you asked the woman out three times, and she denied you all three times, which at that point, I think if it's me, I'm like, this just ain't it. I think I got to move on to the next one. But you didn't. And can you share that story about being rejected and then having the resilience to come back and make it happen? Yeah, well, I mean, I need to be careful here. And I was very careful and nervous back then because this was, I met this woman on her first day of work at the White House in 2011. And you want to be very, very careful. I didn't want to get busted for sexual harassment, right?

So we became friends first, and I don't think I asked her out until we'd known each other for a few months. And she said, no. And you're just cool about it right away, no problem. You just remain being an excellent colleague. An opportunity presented itself where we were at a party two months after that, and I asked again, and she said no. And this is when I'm starting to think, like, do not mess with this. But then we were at a Christmas party together two months after that. And I asked one more time.

And she still said no. And that's what I actually did tell myself, this kind of tramples on your point about resilience. But I said, look, three strikes you're out. Do not do this again. We are done. Third time is pretty impressive, though. You still went for it.

Maybe you were boozed up a little bit. But like you still went for it a third time. I actually went for the third time because one of her friends told me to. Oh, okay. And one of her best friends from college told me to. We were at the White House for a White House Christmas party. And she said, you need to ask her again. And then I was starting to worry that it was a setup, you know,

especially once she said, said no the third time. I was like, what the hell? And but that's when I shut it off. Although what changed my life was the next morning, she emailed back and said, I changed my mind. Let's go out on a date. And now we are married with a daughter who you've heard throughout the entire podcast. So fortunately, all is well. That ends well. But that was risky and dangerous. And because you don't, you don't want somebody else at work to feel pressured or like they have to say yes. So I was always very aware of that and yet I knew that this was the person I wanted to spend the rest of my life with and Kristen is all over this book. Yeah, I just like the story because also I met my wife at work.

A lot of people do and I wonder how that's going to go now with people, not as many people working together. We have a few more minutes. I wanted to do one little excerpt from the book about fathers. I think you and I are also similar to have grown up in an amazing household with great parents. But that's not the case for everybody. And so I'm going to read this section to you and just ask you to expand on it and maybe even compare and contrast to your upbringing, my upbringing being similar to yours. But this is Father's Day 2013. President Obama met with a group of teenagers in Chicago's becoming a man program for at-risk youth boys. He spoke with them for over an hour, which apparently messed up the rest of the day's schedule because he went long. But a few months

later on Father's Day weekend 2013, you write that he invited them back to the White house this time and prior to the meeting the boys went to this local convenience store and once when they are in the overall office they gave President Obama a Father's Day card and they'd all signed it and one of the boys looked at him and said I've never signed a Father's Day card before and the president paused you know really thoughtful guy and he says I've never signed one either and to me it just spoke to like wow like these that's such a different world from what I'm used to, I think from you too. Writing that, thinking about that, being around that.

How does that make you feel just as a whole when it comes to now you're a dad, you grow up with good parents? He didn't. And those group of boys didn't either. It's just amazing to see the differences amongst all the people that come to the same place. Yeah. And that's what makes him such a good writer and wordsmiths, too.

Like he could have said, oh, I never knew my dad either. But he's just, he's got this way just saying, when he said, I've never signed a father's day card either. It's just this instant connection with these young kids who could never see themselves in the Oval Office or who have probably been told you're never amount to anything. And then suddenly the President of the United States just flat out shows, not tells, I'm just like you. I mean, I'm so fortunate that I don't have any, I don't have any daddy issues or mommy issues.

Like, I just grew up loved. And I'm very, very fortunate for it. And, you know, for all the differences that Barack Obama and I had, you know, not just physical, but where we grew up, how we grew up, we, that never got in the way of our shared worldview. It made for much more interesting speechwriting and storytelling that he had such a vivid and varied life. But you're always aware of what his words mean to people, right? You don't have to tell this long, meandering, um, that it's within an inch of its life story.

This gets back to the fearlessness point. You can just say, I've never signed a Father's Day card either. And suddenly all those kids know exactly what that means. And it was just this amazing moment. One quick last one, Cody, before we run, man, especially someone who's had an incredible career like you have and you're right in the middle of it.

When you're meeting with someone who's maybe a recent college graduate and they ask you for vice. They ask questions. What are some general pieces of life slash career advice you give to that person? Yeah, I tell all my students this too, show up and dive in. I actually wrote that in the farewell address for the same reason. All my students are all so twerked up about getting that first job, you know, as if it will define the entire trajectory of your career. And that's just not true. Rather than waste time picking the first job, just get in there. Join a campaign. You know, you learn. Your first job is actually your best learning experience.

Even if you think the job sucks, like, you know, my first internship on the hill, I was literally walking the senator's dogs, running memos around the hill. But if you, if you open up your eyes,

you get to see a bunch of cool stuff. You get to read a bunch of cool stuff. You get to read about policy before it happens. You know, you get to watch policy being made. And if you approach that first job as your best learning experience, that's really going to set you up in big ways for the future. So good, man.

I am so appreciative of you for doing this. I'm going to think about making speeches sing because of you. And I'm just a real appreciative of the book, Grace. Grace, President Obama, in 10 days in the Battle for America. It's really well done. Amazing storytelling that weaves it all together. I know how you did it, but I'm glad that you did because it's really good. I encourage people to read it, regardless of where you fall politically, I think you'll enjoy this book.

It's extremely well done. And Cody, I just like said, I love to continue our diet. dialogue as we both progress, especially I have reading a lot about what you do at Fenway and teaching. I think there's so much to learn in this space for us as leaders that's really important. So I really appreciate it, man. Anytime, brother, I really enjoyed this. Thank you very much. I am fascinated by the job of a speech writer. I don't think it's something I would ever do, but to think of the person who is writing in someone else's voice,

voice and in this case the most powerful person in the world and at times you're writing eulogies and other really important speeches it blows my mind so when this opportunity to talk with cody presented itself i leapt uh at the chance to have the conversation i really enjoyed it i hope you did as well a few takeaways from my notes the use of productive paranoia cody said i was so afraid to fail that i would do anything to succeed i think high achievers have this in common we can use fear as fuel. Then storytelling as a speaker, it is our job to help the people in the audience see themselves in the place of the hero in the story.

When you're preparing for your next team meeting or town hall address, think about that and how you can tell stories that do that for the people in your audience. Then the singing at the eulogy in Charleston. what we can learn from President Obama doing that, if you want an A-plus performance, you have to choose to go for it. You can get a B, I think at least, by playing it safe. But I don't think you can perform with excellence

at that A-plus level unless you make the conscious choice to go for it. And as leaders, I want us to make that choice. Again, I hope you enjoyed this one as much as I did. If so, I would love it if you would tell a friend or two. Hey, you should listen to this episode of The Learning Leader Show with Cody Keen. I think he'll help you become a more effective leader. Because you continue to do that and you continue to write reviews and rate the show,

hopefully five stars in Apple Podcast, you are giving me the opportunity to do what I love on a daily basis. And for that, I will forever be grateful. Thank you so much. Talk to you soon. Get wait.