269. Why Truth is Funny: 7x Emmy Winner Beth Sherman on Building Trust at Work

0:00I want you to meet Beth Sherman. She's written for David Letterman, Ellen DeGeneres, and the Oscars twice. In fact, if you've laughed at it on TV, there's a very good chance she's written it. And she's got a very specific message for anyone who's ever felt pressure to be funny at work.

0:15Beth Sherman:Here's the secret of comedy is that truth is funny. Life is absurd. People are bonkers. Truth is funny. All we do as comedians is observe and report truth. And what's really behind that is it's not about humor. It's about humanity because that's what humor is. It's because when someone makes us laugh or smile, we feel seen and heard and understood. And that ability, you don't need a professional to do that. You simply need the ability to observe. You need the ability to reflect what you observe. You need some emotional intelligence. Beth spent 30 years in Hollywood writers' rooms. But now she works with people who want to learn how to use humour to build trust.

1:00But she's discovered something surprising. The secret to building trust at work isn't actually about being funny. It's about being observant. And here's what's brilliant about Beth's approach. She's not teaching you to become a comedian. She's teaching you the same principles late night writers use to build instant rapport with millions of strangers. And it turns out those same principles work in sales meetings, presentations, even quite tense workplace conversations. Beth has a framework that distinguishes between self-awareness and self-deprecation, and why that difference matters so much more than you think.

1:35Plus, she'll explain why truth is funny might be the most valuable business principle you've never heard of. This is going to make you rethink every workplace interaction you've ever had. Hello and welcome to Truth, Lies & Work, the award-winning podcast where behavioral science meets workplace culture, brought to you by the HubSpot Podcast Network, the audio destination for business professionals. My name is Leanne. I'm a Charter Occupational Psychologist. My name is Al. I'm a business owner. And we are here to help you simplify the science of work. Beth Sherman has written for some of the biggest shows in American television.

2:08Late Show with David Letterman, The Tonight Show with Jay Leno, Ellen for three years. She's written for the Screen Actors Guild Awards and also for the Oscars twice. She's taken everything she learned from 30 years as a professional comedian and don't forget seven times Emmy award-winning writer. And she's translated it for business professionals who want to create emotional connection quickly through trust and rapport. And this isn't about telling more jokes at work or becoming the office comedian. It's about understanding the fundamental principles behind why people laugh, why they connect and how that creates the trust that's essential for persuasion in business.

2:44So whether you're in sales, marketing, leadership or just trying to make presentations that don't bore your audience to tears, Beth's insights are gold. So after this really quick break, we'll discover why the truth is funny, why your audience can smell it when you're trying too hard, and the crucial difference between being self-aware and self-deprecating. This is going to be brilliant. Oh, and funny. See you in a second. HubSpot makes impossible growth impossibly easy for their customers. And here's a perfect example. Lee, your turn. Morehouse College needed to reach new students with fresh, engaging content, But with a massive 900-page website, even the tiniest updates took 30 minutes to publish.

3:25Breeze, which is HubSpot's collection of AI tools, helped them write and optimize their content in just a fraction of the time. The results? 30 % more page views, and visitors now spend 27 % more time on their site. If you're ready for impossible growth like this, visit HubSpot.com.

3:46Beth Sherman:I spent 30 years as a TV writer in the U.S. and as a comedian. And now I work in the business world and I show people how to build trust and rapport faster. And a lot of it is by using the techniques we use in comedy. So it's not about showing people how to be funny. I'm not out there to make more comedians. I don't need the competition. What I'm trying to do is show people the principles behind what we do as comedians to build trust and rapport immediately with strangers and show them how they can use that as a really strategic tool in business. because that's getting people on side is most of the job in business is persuasion.

4:36Beth Sherman:I don't know that I'm famous for it, but my resume says that I have written for a lot of big TV shows in the U.S., mostly in late night. So I've written for Late Show with David Letterman. I spent five years at The Tonight Show with Jay Leno. I wrote for Ellen for three years, which was not technically a late night show, but structured very much like that. And I've written for a lot of big award shows, including the Screen Actors Guild Awards a few times and the Oscars twice. You mentioned something a minute ago. You're not there to try and make comedians. I think a lot of people who think funny people are essentially either comedians, professional or just amateur.

5:17What's the difference?

5:18Beth Sherman:Humor is it's a it's a way of seeing the world. I mean, I'm not trying to make comedians. The way I explain it in talks is that I'm not trying to make comedians out of people because in presentations and in public speaking, people feel a real pressure to be funny. And audiences can smell it. They can feel it when someone's trying too hard. I mean, we've all watched it. That's often what a lot of dad jokes are, is people just trying too hard. And when you're really trying to be funny and you don't understand truly what's behind, you know, if you don't understand the result that you want, which is building trust, building rapport, creating a relationship with people, if you don't understand that, then it becomes very performative and over the top.

6:15Beth Sherman:Because humor is, it's humanity, really, at its core. Humor is humanity. It's the ability to find common ground quickly and show people that we are, well, human. It's relatability and that ability. And you certainly don't have to be a professional comedian to do that. And the example that I find myself using a lot is if humor is incredibly powerful tool for communication in life, let alone in business. And if we forget work for a second, just think about what you look for in a partner or in a spouse. What's on your list of absolute must haves, the non-negotiables? and I ask people to raise their hand.

7:03Beth Sherman:Who has sense of humor somewhere on that list of what you look for in a partner? Most people have it pretty close to the top. Everyone raises their hand, right? I mean, we all look for that. It's because when someone makes us laugh or smile, we feel seen and heard and understood. And that ability, that feeling doesn't have to come from, you don't need a professional to do that you simply need the ability to observe you need the ability to reflect what you observe you need some emotional intelligence you need um you need to care you know you need to want to make someone see your side to make someone you need to want to relate to other people what i'm hearing from that beth is that you don't necessarily need to be a funny person.

7:58You need to understand a little bit about how humor works. Is that right? Or have I misunderstood?

8:04Beth Sherman:No, you've understood that correctly. And you've articulated it in fewer words than I was able to at this hour of the morning. Let's be honest. Yeah, come on. It's what? It's nine o 'clock in the morning here. This is not where late night script writers shine, is it? We should have done this at three o 'clock in the morning. I want to ask you, I think I've heard you say truth is funny. Is that something you you've said and what does it mean i almost never stop saying it uh i i say that constantly because that's to me that is the key to understanding for for people who are not in comedy that's the key to understanding uh what makes people laugh and and what gets that emotional impact because because that's really what we're trying to do people in in at work or not at work we spend a lot of time I'm trying to persuade people to do stuff.

8:57Beth Sherman:And if you, but you can't persuade anyone to do anything until you've built trust. And how do you build trust? You build trust by getting people to feel emotion. And there are lots of emotions you can get people to feel. But happiness is one that's a little bit more fun. You can get them to feel resentment and anger. that seems to be working in some in politics now but you can also if you get people to feel happiness that's a great way to build trust and that will persuade people and so the easiest way to do that and the way we do that professionally, here's the secret of comedy is that truth is funny, life is absurd people are bonkers truth is funny all we do as comedians is observe and report truth.

9:52Beth Sherman:And we do it with some timing in the sense of there's the element of surprise and there's self-awareness and specificity. I mean, there's ways to sort of, I was going to say manipulate, that's not the right word, but there's ways to package that truth and there's places to go to find kinds of truth that work particularly well for humor. But rather than just trying to be funny, try to be a good observer and reflect that truth back to people. And that's what creates connection. That's what creates laughter, smiles, the kind of emotion that builds trust and persuades people to take action. And sometimes, you know, that action is buying from you, working with you.

10:40Beth Sherman:It's something big. But very often, the action you want people to take is very small. It could be as small as getting people to give you the benefit of the doubt and continue listening to you for the next 30 seconds and then the next 30 seconds after that. I watched some of Ricky Gervais' stuff at, no, I don't know, is it Golden Globes? There's one of them where he's reflecting back reality to a load of very, very influential and famous and wealthy people. It lands, but does it land? I mean, not everyone can go out there and do that kind of thing. I wouldn't go out there and do it at your office Christmas party.

11:18Beth Sherman:I mean, there's a, first of all, there's a range. You know, when they say don't try this at home? Look, if people go skiing and snowboarding, but then you watch the Olympics or the X Games or something like that, you see people doing gigantic flips, you go, well, okay, yes, I go skiing, I go snowboarding. I don't try that because it's not going to end very well for me. but someone like Ricky Gervais, look, one, he's a professional. He's a great writer, and he has great writers with him. He has been asked, has been asked very specifically at the Golden Globes. The way award shows work is you come out, you do a monologue.

11:57Beth Sherman:And by the way, the point of that monologue is to name check people in the room so the control room can get pictures of people, can get, you know, take a shot of people. You're going to mention everyone, all the big names that are there who are there because they're nominated or just there because they're gigantic names. So when we sit down, I haven't worked on the Globes, but for other award shows, when we sit down to look at a monologue, there's a target list and not target in the bad sense, just the people at home. If Tom Hanks is there, the people at home want a shot of Tom Hanks and it makes the show look exciting.

12:32Beth Sherman:If you get a shot of Tom Hanks, if you get, you know, anyone who's there, who is noted, who is a big name. So what Ricky does is, yeah, his humor is edgier. He speaks a more raw type of truth. But if you look at the things that he says, they're real true. They're awfully true. But he's been asked to do it. He's a trained professional. And the people who have shown up, they know what they're there for. First of all, they know that there's three guys in black pointing cameras at them. So they also have a pretty good sense that the next joke is going to be about them because it's the reaction shot.

13:26Beth Sherman:That said, what people listening to this can learn from that is certainly that truth is funny. I would say that when it comes to using humor to build rapport with the person you're using humor at, I also talk about in the context of humor being a love language. It's a way to say things that you wouldn't say or couldn't say directly. It's a way to say things between the lines. so if you are using it if you are giving away awards or giving out awards at your office party or your office event or you've been asked to speak at a toast or something like that yes of course you have you you can speak truth and you can point out

14:23Beth Sherman:characteristics of people. I mean, I wouldn't go with physical characteristics, but you can point out behavior, you can point out trends, you can point out the elephant in the room. But I think it's very, very important, if you want a good result, to keep in mind, like just be very mindful of what your words, what you're saying between the lines, What is the message that you're saying to people? So if I say, you know, Al's got one of the biggest podcasts out there. He's got 400 hours of podcasts. So clearly he likes the sound of his own voice. No, I'm true. That's something where hearing it as a comedian and as an editor, as a comedy writer, I hear that and I go, okay.

15:08Beth Sherman:But we're trying to keep Al on side. We're trying to make him feel good. So I would sort of wrap it a little bit in a compliment. And I would say he's got one of the number one podcasts. It's absolutely brilliant. And he's done however many episodes, which adds up to about 400 hours. Like, I would sort of list the positive things about it. He's got how many subscribers, that kind of thing. Really big it up and make it clear that I have respect for this thing, that I have respect for the product, and I have respect for Al. and then i would you know so so then when you say loves the sound of his own voice then there's balance to it and the thing that you're saying between the lines you are very clearly saying between overtly and and more discreetly you're saying what a podcast i mean this guy is accomplished he knows what he's doing so that when you sort of have the gentle poke it's all in context.

16:11Beth Sherman:It's sending out the overall message that you want to send. But again, it's looking at the full picture and it's listening to and being mindful of what it is you're saying between the lines and making that very clear for other people. Because if we structure something that way, what we're saying between the lines is, I have a lot of respect for him, so much so I might be a little bit jealous, but that's on me, that sort of thing. But if we just go right to, you know, he likes the sound of his own voice, then what that says between the lines is, I might not like him all that much, or I don't think other people should like him, or I might be jealous, but in a small and petty way.

17:00and and that's a very different message and that means people will think differently of me as the person speaking so we've got the situation where you've been asked to to talk and people are expecting you to be funny so that is your best man's speech that's perhaps the boss stands up at the end of in the christmas party there's those kind of situations quite specific you've given us a really good guideline of how to be how to be funny without being insulting in that situation. Let's go back into the actual office, the day-to-day. So you're just, you're sitting there next to Frank, next to Janet, and you want to kind of lighten the mood.

17:37It's a bit of a dull day. You want to lighten the mood with humor. Would it be easy to start off with what you shouldn't say to Frank and Janet to lighten?

17:47Beth Sherman:The rule I try to have is, unless everyone's laughing, everyone, unless both Frank and Janet are laughing, and everybody else in the room, then it's not funny. So I think I would go with, I would look at what's happening. I would look at what's happening. I mean, why? Humor diffuses tension. What's the tension? I'm trying to diffuse. So if it's, we've just lost our third big client, or someone that we've just had a meeting where we found that out, I might say, well, that's, oh, we have a great track record. I mean, sometimes you can just go with understatement. So you're acknowledging a truth.

18:27The truth is still the funny part, but you're understating

18:33Beth Sherman:things. Or you could say, well, I think that was the best meeting we've had yet. Or you could pick some small parts of what's going on. Well, at least we have the good cookies today. There's probably not much you can say that's going to put Frank and Janet on the floor laughing so hard that they're holding their sides. And if Janet's over a certain age, leaking. And I say that as a woman of a certain age where it starts getting dangerous to laugh too hard. This has really become a very, maybe that's too much truth. Truth is funny, but truth is it's seasoning, right? Think of the truth as seasoning.

19:18Beth Sherman:If you think of it like salt, not everything needs a lot, but everything needs some. So in that situation, you're not trying to go in there and do a headline stand-up set. You're not trying to bust out your Netflix special to make Frank and Janet feel better. You're just trying to diffuse a little bit of tension. You're trying to sprinkle in a few grains of sea salt on chocolate, it right you're just trying to give it some balance like that i like that so i think there's unfortunately in almost any office of any size there's going to be one person who thinks they're funny but they're not first of all why are they not funny well let me i can speak to self-awareness first or or to why they're not funny and and i would say it's often because of a lack of self-awareness.

20:08Beth Sherman:And I'd also point out that in leadership and in management, self-awareness is a pretty important thing to have. So the fact that they're not funny might not be their only flaw. It might not be the only thing that's holding them back.

20:26Beth Sherman:Self-awareness is simply, well, it's emotional intelligence, right? Self-awareness is being able to acknowledge what the other person is noticing or thinking. So if someone doesn't have self-awareness, they're not going to, you know, the jokes that they make, and, you know, let's put those in air quotes, but the things that they say thinking they're funny aren't going to land well because they don't know their audience and they aren't thinking about what they're trying to say between the lines and it tends to cause tension. They're just bad at it. But I think a lot of that often goes back to a lack of self-awareness and not being funny or their jokes not being good is often a symptom of a bigger problem.

21:58Billion Dollar Moves wherever you get your podcasts.

22:28and if you're front row, you've given overt consent that that's what's going to happen. Whereas what you're saying is that if someone's in an office situation, nobody's come in in the morning and given you consent, given the person in the corner consent to have the mickey ripped out of them. Is that right?

22:45Beth Sherman:Look, I think Jimmy Carr is very funny. He's not my particular taste, but that doesn't mean he's not funny. He's made me laugh. Would I pay 50 bucks to go see him? Probably not. But, I mean, he's great at what he does. So, yeah, if you put yourself in that position, you know what you're going to get. I mean, it's like ordering something spicy off a menu. If it says that it's spicy, if it's got those little, you know, how many, if it's got three peppers next to it on the menu, don't be surprised. But if someone says, here, try this, and it's crazy spicy and they haven't warned you, then that is an unwelcome surprise.

23:29Beth Sherman:But by that same token, it would mean that person did not have the self-awareness to say, maybe you should tell people this is about to happen to them. the office also again we're talking everything i'm saying is is talking about it in the context of business where you're trying to build relationships you're trying to make your business better you're trying to draw in clients you're trying to have better relationships with colleagues you're trying to move things forward that's an entirely different animal than getting up on stage at a comedy club where again everyone's giving their consent everyone knows why they're there.

24:07Beth Sherman:There are things that I would, and I speak about humor to business audiences, but I wouldn't do my act or their jokes that I used to do that I would never do in front of a business audience because they are potentially divisive. And I just, I wouldn't do them only because my main objective is showing people how humor is a to bring people together. And again, it's not just about humor. It's humanity and relatability. And in leadership, you don't have to go around giving out hugs and you don't have to go around giving people, hey, it's coffee Thursday and it's beanbag Wednesday and look, there's cake in the conference room.

24:55Beth Sherman:Maybe it's just acknowledging that whatever's coming down from head office is interesting or that sometimes it can feel like a moving target or talking to someone and asking how things are at home. It's just more of a, it's showing people that inside the authority is an actual human. I think a lot of people want to be humorous at work, but they're not really sure how to start. If you were to coach someone to try and be a little bit more funny, where would you start? Where should you be starting from? I wouldn't try to coach someone to be, if someone came to me and said, I want to be funnier at work, I would cringe a bit.

25:47Beth Sherman:I would say, but what do you mean by that? Do you mean that you give lots of presentations and you find that your audience is not engaged? So are you trying to make them more engaging? Are you trying to keep people's attention. Is that it? And where humor might be one part of how we do it, but humanity, storytelling, relatability, that sort of thing. Or does someone just picturing, I'm going to go into work and stand by the coffee machine and people will be, it'll be my Netflix special every morning while I'm waiting for the Keurig to brew something. But really when it comes to just creating that safe feeling, that feeling of trust and rapport, I would say the first thing to do is to pay attention to how you do it outside of work.