ALISON BEARD:  I’m Alison Beard.

ADI IGNATIUS: I’m Adi Ignatius. This is HBR IdeaCast.

ALISON BEARD: Adi, you are very familiar with both of the guests on today’s show. One is a comedian and talk show host, Jimmy Fallon. The other is a marketing executive turned reality TV star, Bozoma Saint John. But what they have in common beyond TV is an expertise on how to create breakthrough moments for themselves, their offerings, and all of the brands that they’re associated with. We know that’s really important now because it’s an increasingly crowded, complex, confusing media and advertising market.

ADI IGNATIUS: Yeah. When you first told me you were going to interview Jimmy and Bozoma, my first thought was, okay, that’s pretty interesting. I’ve interviewed Boz, she’s incredible. She was an executive at Pepsi, at Apple, at Netflix. I get what she’s all about. Jimmy Fallon, I watched him on Saturday Night Live. I’ve watched him on The Tonight Show. He’s energetic, he’s entertaining. I’d be interested, what does he know about this? What does he have to say about marketing?

ALISON BEARD: They’re both people who over the course of their long careers in different ways, have shown a really uncanny ability to adapt to new trends, particularly technological ones, and keep capturing the attention and imagination of diverse consumers. Most recently, they’ve teamed up for a reality competition show called On Brand. It’s like Shark Tank, but it’s amateur creatives competing to design ad campaigns for companies like Dunkin and Southwest. I would say that the show vastly oversimplifies the business of marketing, but it is an interesting tool in and of itself because each episode functions as an ad, because it’s totally about one company. But it was a really good reason for getting them onto our show to talk about lots of issues, not just branding.

ADI IGNATIUS: No, I’m sure. Look, I mean, they’re both incredibly energetic and incredibly entertaining. Have an audience. I’m interested. What were some of those issues?

ALISON BEARD: In addition to talking about how to market companies and products, we talked about how to market yourself in your career. We talked about how they show up as leaders of creative teams and balance having strong points of view with being collaborative. We talked about how they innovate on different platforms like TikTok and YouTube, and then what type of marketing really does break through. Here is that interview with Bozoma Saint John, the former CMO of Netflix and Jimmy Fallon, host of The Tonight Show with Jimmy Fallon. Together, they host On Brand.

The entertainment media and marketing industries have changed dramatically since both of you started your careers. There’s cable and then internet, and then streaming and then social. So what would you say is really the secret to capturing attention now, whether it’s an individual or a show or a corporate brand?

BOZOMA SAINT JOHN: Sure. I mean, God, you made it sound like we started the Stone Ages, girl.

ALISON BEARD: I mean it’s, that’s when I started.

BOZOMA SAINT JOHN: I’m like, speak for yourself. No, but you’re right. Look, the landscape has changed dramatically in the last 20 years, right? The way that consumers listen to entertainment or watch entertainment has changed. I find that being on top of just what people are communicating with each other is the only way in which you can be part of the conversation. Whether you’re a brand or an individual, a show l ike ours, I mean, obviously Jimmy is on TV every day, and so he has the pressure of being able to evolve so that he can continue to keep the audience that he has. So I guess my perspective is just from a brand lens, which is that in order to stay relevant, you really do have to pay attention to the time.

JIMMY FALLON: I think it changes a day by day by day by day. You never really can – there’s probably a couple of weeks where you’re like, “Hey, this is where everyone’s going and then it changes.” You’re like, “Nope, they invented a new thing called flip-flop. Everyone’s on flip-flop.” And you go, “What? I hadn’t even heard of that.” And they go, “Oh, you got to sign up. You’re late to the game.” But it’s always changing and I’m always interested in seeing what the next moves are, especially social media. When we first started Late Night, I remember one of our producers, Gavin Purcell, who’s fantastic. He was like, “You got to get on Twitter.” And I was like, “What is that?” He’s like, “Well, it’s this thing.” And he’s explaining Twitter to me. I go, “Okay,” and then I’m like, “And we’ll put our shows on Twitter.” He like, “Yeah. We can do streaming shows just before we even start up Late Night just to get a following going.”

And I remember getting maybe a hundred followers and I was jumping up and down. I was that into it. I love metrics. I love data. I love to see how things are going up or down or sideways or what type of people are listening or retweeting. We just jumped on and tried everything when it comes out and see if it works for you and you kind of have to learn it and adapt to it. I think number one is still YouTube as far as growth and how much engagement with everybody. It’s just the biggest thing and I don’t know if there’s anything close.

ALISON BEARD: When you have though all these channels varying in popularity, but all the smart people and shows and brands are on them or trying all of them. How do you craft either a persona or a campaign that can break through all of that noise?

BOZOMA SAINT JOHN: I think some of it has to be consistency. Just back to the last question,  I also want to give props to Jimmy himself as a person because he really does throw himself into the creative and into the work. So yes, social media is a powerful tool, but without him actually being in it and doing the trend every day – my point is that it’s not just like, oh, there’s this tool on this platform out there and try to engage on it. Jimmy is putting himself in the work, and I think that’s actually necessary, whether it’s a show or a brand, the consistency is how you show up. If every day, you’re trying to be something different on the platform, nobody’s going to trust you. People, they don’t like that.

JIMMY FALLON: I think that’s also how you find your brand by trying everything on. You go, hey, do I wear bangs? Do I have a bob? Do I have a short hair? You have to try it to see if that’s your style. And you go, hey, I think I found my style everybody. I think for me growing up, I was a very fad type of person. I was ready into fads and trying new things, and I was wearing zipper pants. This is in the 80s and…

ALISON BEARD: Jams.

JIMMY FALLON: Jams is the best. I love my jams. Oh, my gosh. That generation I feel like there were things that were in for two years and then out. Even the music in the 80s, it’s a lot more one-hit wonder, I think, than any decade, but that was because everyone was trying new things and seeing what’s happened. So I think my brain, growing up in that generation of having one-offs and one-hit wonders and things constantly changing and what am I into probably influenced who I am today and how I can function with changing things, and are you good with change? A lot of people aren’t good with change and it freaks people out and they go, “I can’t have a new office. I’m used to my old office.” I go…

ALISON BEARD: Different platform. Same person. Yeah.

JIMMY FALLON: Yeah, I think so. But Bozoma was saying you have to try and you got to get up to bat and swing, and sometimes you hit a home run, sometimes you strike out, but at least you’re trying.

ALISON BEARD: Both of you have very strong personal brands, and I think a lot of that comes from authenticity. But how did you think about that as you built your careers? Bozoma for you in marketing with big jobs at Pepsi and Uber and Apple and Netflix and Jimmy for you with moving from stand up to SNL, to films, and then Late Night?

BOZOMA SAINT JOHN: A personal brand is such an interesting thing because many people will say that like, “Oh, that’s a waste of time,” especially if you’re in corporate settings, but really it’s just new language for what a reputation is. When I started out in this business, of course, I was trying to mimic the successful people ahead of me. It’s like I looked at the corner offices and said, okay, what are they wearing? How do they talk in meetings? What are the ideas they bring? How do they do the thing they do and why do people listen to them? And I just tried to mimic it.

Unfortunately, that did not work and it didn’t work for all the reasons that now as more mature adults we know is because it just didn’t fit and you can’t be authentic. And I know it’s an overused word, but like we were saying before, even as Jimmy explained about trying things on and seeing what fits, for me, it was like this unraveling of who I was trying to be versus who I am. My personal brand became what it is and is because it’s actually just me.

I do wear interesting clothes and I do gesture a lot with my hands and I cry because I get emotional and my hair is always something different. All of those things allow me the freedom to be exactly who I am in every room. And it has made me a better executive. It has made me a better mother. It’s made me a better friend. It’s made me a better contributor to society and a better creative for all those reasons. And so I think the personal brand gets a little confused. Sometimes people are trying to strategize around it and I’m like, no, if you just become more of yourself, then that actually will sustain over time.

JIMMY FALLON: Is it because people can trust you?

BOZOMA SAINT JOHN: Yeah. Right. Because you never come out of character. You know what I mean?

JIMMY FALLON: Yeah. I forget who said, but someone said, yeah. God, I always tell the truth because it’s too much work to lie.

BOZOMA SAINT JOHN: Yeah, it is too hard.

ALISON BEARD: What about you, Jimmy?

JIMMY FALLON: I think when I first started out, I was just hungry and I was focused on getting on Saturday Night Live. That was my goal. So I did stand-up and I did impressions of celebrities, because I knew that Saturday Live used those people on the show to do characters and impressions. So that was going to be my way into Saturday Night Live. So in my stand-up, I would do impressions of John Travolta. I’d be like, “Jeez, I swear to God. I can’t believe this over here. Sandy, what’s going on?” Right, yeah. I don’t know why but that led to other characters, which led to me doing Adam Sandler where it’s like [jibberish]. And you do all that type of stuff and then you go, oh, that stuff we can maybe use.

And I just think that was my ultimate goal is just getting into Saturday Night Live and let’s just check that off. That’s like the bucket list but that was my goal. And I got that at 23, and then once you get it, you go, okay, now what do I do with this? Because I didn’t plan ahead. I didn’t have three other goals. That was it for me. I’m like, uh-oh, I got to figure out what my next goal is.

Do you want to be a movie star? Do you want to be a sitcom star? Do you want to record music? What is your thing? I – So I’ve kind of had to think of a new goal and find it as I was going and see if it fit. I think always for me, as far as material-wise, it was very family friendly. I never really cursed in my act or I was kind of almost prudish.

I think it was my Irish Catholic upbringing, but that’s not really changed for me. So that kind of stayed on brand, but I think I just grew and said, well, maybe I can do this. And then with that didn’t work out. I tried movies, they didn’t really work. And then you just kind of go back to just trying stuff and seeing what sticks and getting into the talk show world, I didn’t really know what I was doing either there, but I got a lot of practice and I was on at 12:30 at night when no one was watching.

ALISON BEARD: I think a few people are watching.

JIMMY FALLON: Maybe like prison guards, and college kids. But I mean, I had to do that and kind of figure out there how to have an interview, how to talk to somebody. Am I nervous? I still get nervous but it’s fun because I care, I think, and I want to do a great job. But you get another opportunity and then you grow and you see how you can do that best.

ALISON BEARD: It sounds like you both very much found your distinct lanes, despite the fact that you’re both in crowded fields. How would each of you describe your leadership brand, right? Because both bosses, you’re running organizations, you’re running shows, you’re running teams of people. What is your unique style or the unique thing that you bring.

JIMMY FALLON: Boz is better at this than I am.

ALISON BEARD: Well, but you’re an informal leader even if you’re not called the CEO of The Tonight Show.

JIMMY FALLON: Yeah.

BOZOMA SAINT JOHN: But he’s still my boss. I still consider my boss, honestly. So I mean, hell, you’re a leader of me if nothing else. Okay.

JIMMY FALLON: Yeah, come on. But you have that feeling when you get in the room with Bozoma Saint John. You go, whoa, this is like, I can feel like-

ALISON BEARD: She’s in charge.

JIMMY FALLON: Yeah, well, you feel like someone smart is in the room. Whereas I’m here, it’s like, oh, my gosh, Uncle Buck is here.

BOZOMA SAINT JOHN: Oh, my God, that is so ridiculous.

JIMMY FALLON: Substitute teachers here. I’m always reading books, and I’d be curious to ask you also what books I should read too for management. And I love all that stuff and I love self-help books and learning constantly about how to do it better. And even if not, remind yourself of what works and what doesn’t work. Being mad doesn’t work. I know that.

BOZOMA SAINT JOHN: Yeah, being mad doesn’t work.

JIMMY FALLON: It just does, right?

BOZOMA SAINT JOHN: It’s so interesting. I think my leadership style has changed, of course, over years and different experiences. The way that I led my Apple Music team in launching the brand and the service itself was far different from the way I led when I became chief marketing officer of Netflix. One because they were so different in terms of not just the product but the time. I started Netflix, we were two months into the pandemic. And I remember my first staff meeting, I mean, there’s well over a thousand marketers, and I didn’t see anybody’s face. And I think I’m the kind of leader that does need to be in the room. I like in front of people. I want to see your face and your reaction and see if what I’m saying is inspiring. Is it funny? Are you confused by what I’m saying? I need all of that to be able to-

JIMMY FALLON: A reaction.

BOZOMA SAINT JOHN: Yeah, I need something! And it was such an impossible time of trying to inspire people to be more creative and think out of the box and all of the things that we say at a time when nobody knew what the hell was going on.

But the constant theme throughout, I think, for me in leadership has always been knowing the detail of what is going on, understanding what people are interested in on my teams, because the challenge is that you put all of the pressure on the results and you don’t think about the people. I have had the kind of career where in order to really do the work, we had to be so close to culture that I needed different types of people on my team, people who didn’t know what I know.

I take a lot from physics, which is the idea of matter. That matter is made up of molecules and you change one molecule and the entire matter changes. And for me, I’m like, matter is a team, the people that I’m working with, and you change one molecule and the whole thing changes. And so understanding the importance of every single person who is contributing, they can be the assistant or they could be the SVP of a region, their contributions are so important. So making people know that so that they want to show up to their job, they want to do the best job that they could do because they know how important they are, because I told them that has been a constant leadership tool for me.

ALISON BEARD: I love that.

JIMMY FALLON: Also what you just said too, also showing up I think is one thing that you learn as the more you do this is that all the great leaders show up.

BOZOMA SAINT JOHN: sYes.

JIMMY FALLON: Whether it’s a restaurant. I’ve seen restaurants fail because you go, hey, we had a great year. I don’t have to go in anymore. And you go, no.

BOZOMA SAINT JOHN: Wait, Jimmy, I’m going to interrupt you one second because actually, I have a story about Jimmy on his leadership, and this is going to embarrass you, so whatever, you just got to deal with it. We had over 270 crew members, I think, on On Brand, and I’ve always felt that I’m a friendly person. I see people, I say hello, all of that stuff, but I’ve never seen anyone do it like Jimmy does, meaning that we were walking onto set one day and somebody was nailing something on a wall, bent over in the corner, and Jimmy was like, “Hey bud, you’re doing a great job.”

I’ve never seen anybody do that in my life. You know what I mean? Just paying attention to the small things. And the showing up is also in recognizing people’s contributions. And so for Jimmy, I think leadership is not just how he commands a production to be done or his contributions to like, oh, let’s use this line or change this word, but also making people feel like they are part of something even bigger and that they’re important, and I saw that in action.

ALISON BEARD: Yeah. It sounds like the sort of infectious spirit that you bring to the show, to public facing engagements, you’re also practicing behind the scenes. Did you learn that leadership style, the idea of keeping it fun, of showing gratitude to even the smallest players? Did you learn that on SNL from people like Lorne Michaels?

JIMMY FALLON: Lorne Michaels, yes, definitely. I think that’s one of the things I learned from him is showing up and just being there for everybody. I think as the part of gratitude, one of my biggest lessons I learned from Cameron Crowe, who’s a great writer-director but he directed me. I was in Almost Famous. You can cue the applause now.

ALISON BEARD: We’re going to go straight to Fever Pitch, but okay.

JIMMY FALLON: No, I’ll start with my first one and I’ll go into my filmography after that. This podcast is three hours, right? All right, perfect. So I remember I was on set and I saw Cameron giving notes to this extra, and he was like, “Okay, you had a long day. Okay, you got three more tables and then you get to go home,” just giving direction to this extra, and then they did action, and the extras didn’t have any lines, just in the background.

And I was like, “Whoa.” No one was looking at him. He was just him and this extra talking and he made that person feel like a million bucks. And that made everybody go like, we are all doing this. Everybody’s worth something here. This is awesome, and I’ll never forget that. It was the coolest thing that he did. So I think combo of that, Lorne Michaels and Saturday Night Live, and I think all the different hosts that come in on Saturday Night Live too, and talking to all them and just seeing how, yeah –

ALISON BEARD: Some people brought that sort of positive addition to the matter that Boz was talking about, and some didn’t, I imagine.

JIMMY FALLON: Yeah, and caring and just go like, oh, that was great what you did. I like that. When these celebrities host Saturday Night Live, they’re coming to a place that they’re not used to. So if you have Robert De Niro, for example, I remember him asking me where his mark was. “Jimmy, where’s my mark?” I’m like, “I’m not going to tell Robert De Niro anything. You can stand wherever you want, dude, I’m good.” He’s like, “No, I don’t really know because I’ve never done this.” And I go, “Oh, it’s right there. And then you’re going to land, you’re going to say the lines facing that way.” He say, “Okay. Cool.” Just help each other. We’re on the team now. I’m like, I just totally helped. I gave direction to Robert De Niro, what is going on in my life? And he loved it, but we would laugh and it was just great.

ALISON BEARD: So we all know that the best creative teams come from putting people together with diverse points of view and everyone sharing their ideas and brainstorming together. But how do you all as strong personalities with good ideas, I imagine because you’ve been very successful, how do you balance expressing your own opinions, putting your own stamp on things with also working collaboratively and bringing in the opinions of others?

BOZOMA SAINT JOHN:

That’s a tough one.

JIMMY FALLON:

Yeah, that’s a good one.

BOZOMA SAINT JOHN: For me, I get very passionate in every job I’ve had, passionate about how the things should land because I’m like, oh, I know that’s going to garner results. Sometimes I’ve been wrong, but I always have a strong point of view. I’m thinking back to times when it’s like, look, as part of a creative team, you do have to follow the direction of whomever is in charge.

It’s kind of like any like a coach or general or something. If everybody doesn’t fall in line, it’s liable that you go wrong. And so at some point as a creative, you can have a strong idea. You can think it’s the best one, but if it is not the one that goes forward, you have to submit and help the next person. And so going back to your question about leadership, it is something I’ve always encouraged my teams, which is that once I’ve been in the seat as the CMO to decide which idea goes forward, and now everybody get behind that idea.

ALISON BEARD: Disagree, and then commit.

BOZOMA SAINT JOHN: Oh, I oh, we should have done this, should have done that. That’s when we’re all going to fail. So it’s like once an idea has been chosen to go forward, everybody put your energy into making sure that that idea is what wins.

ALISON BEARD: How do you steer people with good, well-meaning ideas in better directions?

JIMMY FALLON: This is just me, but I always like to say at least my point of view on something just to say it. And then there’s probably someone in the room that might be better at whatever the thing is, and I’ll let them hear my idea and hopefully, it sparks something that they can land the plane and I don’t need to take credit for it.

For instance, Southwest, we did this episode last night that you watched, but the challenge was to wrap a plane – basically paint the side of an airplane. So it’s a big thing and we’re going, well, blah, blah, blah. How do you do that? Well, this is going to be seen by a lot of people. And then Bozoma goes, “Well, when I wrapped a plane for Beats.” I go, “You wrapped a plane.” Who else? I mean, we’re talking to someone who’s done this. How many people do you know that wrapped a plane before?

ALISON BEARD: I don’t.

JIMMY FALLON: Yeah, I know now you do. Now you know two people but it’s wild. It was like she knows she’s done this. What hits? What do people look at? What do they see? What are the things that pop? And you kind of go, that’s great. We have someone that’s played the game before.

ALISON BEARD: So Jimmy, why at this point in your career did you feel qualified to host a show on branding and marketing?

JIMMY FALLON: I think because of all the years of Late Night and Tonight Show, and my job is basically selling things for my guests. I have them on and I pitch their movies or their music, or I’m selling their wares, their products. I’ve kind of enjoyed it when we have an integration or some brand goes, “Hey, is there any way you can mention toilet paper this week in the show?” And I go, “Love it, bring it on. What do you want? I can write whatever I want, right?” I go, “I will think of something.” And then I go, “Yeah,” and we’ll talk about, “Hey, do you put the toilet paper roll over the top or do you put the toilet paper roll with the paper coming under?” And you have a debate and people get in fights, and it’s funny. That’s a fun challenge. So I’ve done that for the past 15 years. So that’s a long time, a lot of shows. I think tonight’s hitting almost like it’s 2,300th show or something crazy.

BOZOMA SAINT JOHN: Oh, my God. That’s so amazing.

JIMMY FALLON: So I kind of love the stuff, and I had a weird, again, just an odd idea, and I didn’t have to throw them out to people. And so I pitched it to NBC. I typed it up, you know, bothered my wife with all these questions for months, and then I go, “I think this is something I could pitch,” And I pitched to NBC and they said, “No, but thank you so much. You keep these ideas coming buddy and stay strong at Late Night.” And you go, “Okay.”

And then I was like, I didn’t let it die. I was like, I really do think this is something you should give a chance to. I think it’s different. And as Bozoma was saying, at one point, we were talking about this and we’re like, because a brand new type of business structure, even to repaying for the show and all this stuff, but also what Bozoma was saying, it’s kind of like a new toy to play with for brands. Like, how much fun can we have?

ALISON BEARD: Yeah, the companies are sort of sponsoring each episode basically. And so the advertisement isn’t necessarily what’s generated by the contestants, it’s the show itself.

BOZOMA SAINT JOHN: I also want to say that I know Jimmy, he’s creative and he has done a lot of work with brands, but he’s also a student of marketing. W e were just on a show together where we’re playing a little quiz game of like, oh, the taglines and this and that, and Jimmy, he was getting them. And not only that, he’s got the jingles and he remembers. And so it’s like for someone who hasn’t had a formal career in marketing, he’s still an ad guy. I would consider him an ad guy. There’s a natural love and curiosity for the business of marketing and advertising. And so that I think also has a great deal to do with why it’s natural for him to be the one who developed the show and brought it to the world.

JIMMY FALLON: I mean, I love a good ad. Don’t you love to see a good campaign?

BOZOMA SAINT JOHN: Yes, absolutely.

JIMMY FALLON: I love a great campaign. I think Ryan Reynolds is knocking it out of the park.

BOZOMA SAINT JOHN:

Amazing.

ALISON BEARD: We actually, he’s going to co-author, an article in our next issue about Fastvertising and how to quickly capitalize on.

JIMMY FALLON: Oh, he’s best at that. And also probably people wouldn’t have normally given him a chance had he been on a team or a famous ad agency. I mean, I think he used his fame to go like, give me a chance. I’m going to roll the dice on this.

ALISON BEARD: Yeah. It sounds like you’re saying that in this very crowded marketplace as companies are thinking about how to break through, brand integration is one avenue that everyone’s keen on. There is a sort of obviousness to it though, right? So how do you do it in a way that does feel authentic and not just like, ugh, I’m being marketed to right now?

BOZOMA SAINT JOHN: Well, I think it should be obvious. I feel like that’s where brands go wrong when they try to be in a place where they’re not naturally. We excuse Jimmy because he can actually do it very well. So toilet paper maybe doesn’t belong on his desk but he’s going to find a way to bring it in. But the challenge most times is that brands are trying to find integration in scenarios where they simply shouldn’t be because it’s not natural for them to be there. And that’s why it falls apart, not because somebody was sitting there holding their thing and saying, hey, look at this thing, but because it just wasn’t natural to them. And so it’s like, look, when you’re in this space, it should be obvious that I picked up my Pepsi and drank it because I was thirsty.

ALISON BEARD: And then the second avenue you talked about was this idea of capitalizing on cultural moments. And Jimmy, you certainly do that with your show. Bozoma, you did it. I’m sure working at Netflix and Apple and all these sort of fast-paced consumer brands, talk about how you do that in a way that doesn’t seem ham-handed and actually does sort of reach the audience you’re trying to get to.

JIMMY FALLON: Again, there has to be some authenticity behind it too, even though it is the moment, but you take the moment and how do you make it you. So if it is doing a Taylor Swift dance challenge, I can do it with Taylor. The other way to do it is just do the dance challenge myself and be a 51-year-old man trying to do a dance challenge on TikTok, and that’s what it looks like. And it’s like that’s more authentic. And you go, he’s not trying to be a teenager. He’s acting his age. I mean, I’m feeling it now. My era, I’m feeling I’m going into my old man era or getting older era. I feel like if I’m at a high top table, if I go to a restaurant with a high top, if I drop my napkin, I’m not picking it up.

BOZOMA SAINT JOHN: No, no, it’s not.

JIMMY FALLON: My back will hurt.

ALISON BEARD: And we definitely can’t read the writing on the menus either, so.

JIMMY FALLON: I am not the person yet that turns the flashlight on, but I’m real close.

BOZOMA SAINT JOHN: I’m there. You know what I mean?

JIMMY FALLON: I’m real close.

BOZOMA SAINT JOHN: Yeah.

ALISON BEARD: So speaking of being of the moment, as a star, as a show, as a brand, it is a very divisive time politically in the U.S. We’ve seen companies come under fire for moves, celebrities canceled and executives are really unsure what sort of risks they can take right now. And I think the most recent example, obviously in your world, Jimmy, is ABC pulling Jimmy Kimmel off the air for comments about Charlie Kirk.

And you have made a point of being family friendly and apolitical. So just talk a little bit about why you’ve made that decision and are sticking to it. And then I’d love to hear from both of you on how you think that corporate brands can navigate this moment and sort of do the right thing, speak out in moments that they find appropriate, but then not get embroiled in controversy. Jimmy, why don’t you start?

JIMMY FALLON: I mean, it’s also tricky and it’s all kind of moving very fast. Obviously, if there’s a case of government versus the artist, I’m on the artist side. I think everyone should be able to say whatever they want. And I think for me, I’ve kind of learned from Saturday Night Live how close you can get to the edge for myself, which is being authentic. I think my monologues have kind of always been kind of the same. I have probably four or five jokes that are kind of about the political world, and then five jokes about fast food or something. I think if you look in the New York Times the next day, I’m up there, my jokes are up there with all the other guys, but I diversify myself with more poppy stuff. That’s just because of what I’m into.

They do it better than me, the politics stuff, and I’m happy that we have different voices out there and all talking. And if you want that, you can get it. So I think I just stick to what I do best, and whether it be me dressing up as a showgirl and dancing, with the K-pop Demon Hunters, that’s feels on brand to me. I’m not sure if I would want to see any of the other guys do that. So I can only pay attention to myself and do what I think is the funniest, sharpest, and most entertaining stuff every night.

BOZOMA SAINT JOHN: Yeah, I think in the executive world, it gets tricky because you’re representing yourself but you’re also representing the company. Where I think sometimes executives get scared, of course, is that their own personal view is going to be taken out of context or punish the company in a way. And I’m like, that is the truth. So grow up, take a stand, say something, and if you get fired, so be it.

And I remember that I was having a lot of these conversations five years ago when it is like Black Lives Matter was popping off and George Floyd had been murdered. And there’d been like, people were like, “Oh, should we make a statement?” And I had so many friends in the executive space. We were in our little group chats and people were like, “What should I say?” And I’m like, “Well, what do you believe?”

JIMMY FALLON: Start there.

BOZOMA SAINT JOHN: You’ve got to start with wherever you are. And first of all, this is way different from 20 years ago where the society did not expect to understand who’s behind the wall. It is like now people want to know what did the CEO think? What is their opinion on things? Where do they stand? What does the company care for? Those are all things that our consumers and our audiences want to know. And so you have to express it. And unfortunately, it’s like if that has backlash, then that is the job.

ALISON BEARD: What advice would you give to the senior leaders in our audience who are trying to make their brand stand out right now, especially when it’s hard to take risks?

BOZOMA SAINT JOHN: Well, I don’t know why you have your job if you can’t have a stance on something. You have to have an opinion, whether that is cultural opinion or it is an opinion about innovation and what you’re going to create next for your company. I don’t know of any senior leader who’s been put in the job just to tread water. It’s like you’ve got to actually make a change. You’ve got to actually make some impact in the work that you’re doing. And so I don’t have a lot of respect for leaders who come in and do nothing.

ALISON BEARD: Jimmy.

JIMMY FALLON: I think be different as much as you can, be different, take chances, take risks. Everyone says take risks, obviously, but I mean, really do something fresh, do something new and something we haven’t seen and that will pop. I think you’ve seen that with Super Bowl commercials, which I always go back to just a fan, but having a celebrity in a commercial used to be the big thing. Oh, my gosh, it’s Michael Jackson drinking Pepsi. Oh, my gosh. Now that’s every commercial. So now what do you do? Because that already is done.

So now sometimes it was a QR code and you go, what is that? That was the whole ad. I don’t even know if it worked, but it was something different and it popped and you go, people were talking about it. So I think there’s many ways to attack it from different angles. And I think just write them all out. See what way you can do it and try to see what’s the next or clever or different angle that no one else is doing and do that. And if you can do that and have people think that they’ve seen it before, that is the secret sauce. Because if you go like, oh, yeah, I’m used to, that’s of course. Where’s the beef? I always say that.

ALISON BEARD: Surprise that it becomes instantly familiar.

JIMMY FALLON: Yes. Well said. Well said.

ALISON BEARD: Okay, I have one recommendation for next season, an AI contestant.

BOZOMA SAINT JOHN: Oh, that’s interesting.

JIMMY FALLON: Wow.

BOZOMA SAINT JOHN: Wow. That would be something, because that’s a whole –

JIMMY FALLON: I think it would be-

BOZOMA SAINT JOHN: Alison wants us to be embroiled in controversy is what’s happening.

JIMMY FALLON: I think that would be…

ALISON BEARD: Really interesting.

JIMMY FALLON: … hilarious.

ALISON BEARD: Brainstorming. It’s developing concepts. It’s thinking out of the box.

JIMMY FALLON: Do you think it would work? I don’t think it would work.

ALISON BEARD: I mean, or maybe AI assistance something. I think it’s something to explore. Yeah. I did talk to an executive who said the one thing AI doesn’t have is taste, and so maybe that is the problem.

BOZOMA SAINT JOHN: That’s what it is.

ALISON BEARD: Okay.

BOZOMA SAINT JOHN: We got some people who didn’t have no taste either, so there you go.

JIMMY FALLON: Exactly.

ALISON BEARD: Well, thank you both so much for your time. I really appreciate it.

JIMMY FALLON: This was awesome. We loved it.

BOZOMA SAINT JOHN: Thank you so much.

ALISON BEARD: That was marketing executive Bozoma Saint John and comedian Jimmy Fallon, who also hosts the new NBC show On Brand. Next week, Adi looks at the impact of Freakonomics, 20 years after its publication, with author Stephen Dubner.

If you found this episode helpful, please share it with a colleague and be sure to subscribe and rate IdeaCast in Apple Podcasts, Spotify, or wherever you listen. If you want to help leaders move the world forward, consider subscribing to Harvard Business Review. You’ll get access to the HBR mobile app, the weekly exclusive Insider newsletter, and unlimited access to HBR online. Just head to HBR.org/subscribe.

Thanks to our team: Senior producer Mary Dooe, Audio product manager Ian Fox, and Senior Production Specialist Rob Eckhardt. And thanks to you for listening to the HBR IdeaCast. We’ll be back with a new episode on Tuesday. I’m Alison Beard.