Did You Hear the One About Using Humor in Sales?

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This is a podcast episode titled, Did You Hear the One About Using Humor in Sales?. The summary for this episode is: <p>What’s the secret to being taken seriously? Stop taking yourself too seriously.</p><p>In this episode of INSIDE Inside Sales, Darryl is joined by Jon Selig, a rockstar sales guy turned stand-up comedian, to talk about using humor in sales as a way of establishing rapport and connecting with your prospects. They also delve into the importance of being different, challenging the stuffy dress code, and upping the personality game as sure-fire ways to make a memorable impression. </p><p><a href="https://info.vanillasoft.com/subscribe-to-the-inside-inside-sales-podcast" rel="noopener noreferrer" target="_blank">Subscribe now to learn how stand-up comedy lends itself to sales and how you can laugh your way to closing your deals.</a></p>
Share the lessons and advices
03:11 MIN
How do you teach people?
03:25 MIN
Intentionally engaging the crowds
02:15 MIN
Write the jokes that roast your prospects pain
03:42 MIN

Darryl Parrel: How's everybody doing? It's been a while. At least, it feels like it's been a while. I mean, you guys know the drill, when you do these podcasts, sometimes you're doing them two, three at a time, and they drip out slowly over the course of the month. They're never done live. If you were thinking all of these were done live, my friends, you are mistaken. Nobody's podcast is done live. Heck, half the webinars these days are not done live, but that's a whole different story. No, it's been interesting. I just got back, at the time of this recording, from overseas. I had my first overseas travel. I went to England, and we were part of the B2B Marketing Expo and the Sales Innovation Expo, and we were the Platinum Sponsor. This is a legacy of pre- COVID times in investment. We do this show every year. Obviously, in 2019, we'd invested for the following year. 2020 didn't happen, so we finally had it in 2021. It's the first time I've traveled overseas since all this happened. The only other time I traveled, and again, I'm in Ottawa, Canada, is I'd gone down in June to Atlanta, Georgia, to the Outbound Conference. So this is my second time traveling since the pandemic, and it's the first time overseas. I got to tell you, it was so nice to be at a live event again and talking to people and friends whom you know so well. You know them online. They're part of your tribe. You talk to them all the time on LinkedIn. You might have some emails. You might have some Zoom calls. But it's just not the same until you do it in person. So that was my exciting part. But what I took away from that whole adventure, believe it or not, was something that I almost had forgotten about, which is the power of relationship. And I'm going to get to that in a second. What do I mean by that? When you see people, when you connect with people online, on social, you establish a bit of a rapport. They like you or they don't. So if you're doing social selling, if social is one of your outreach channels, which by the way, it should be, your personality matters, whether people decide they like you or not. The same thing is said on email, your personality can come through on email and on phone. And on phone, you're thinking to yourself," Well, nobody answers the phone." That's true. They may not answer the phone. Fully acknowledged it. However, you'll leave them a voicemail, and in that voicemail, they'll pick up your tonality and your spirit and your personality, and they will make a decision on you. The classic case is it takes what, people decide in, was it seven seconds, whether or not they like you, and within 12 seconds on whether they trust you, want to give you any more time. I mean, I could be messing that up, but those are various stats. The gist is correct. So that's the importance. And what was so amazing when I was over there was I saw all these people whom I had made connections with since pandemic started. In other words, I've never met them live and in person. And they would come up to me like they were my best friend. And it was so exciting to see, and I would get hugs or elbow bumps or fist bumps or handshakes. And yes, I would wash my hands non- stop afterwards and use disinfectants. It made me wonder, why? Why did that happen? Why would they do this? Because we'd never really met in person before, ever. And what became very clear for so many of these people was they thought I was a couple things. They thought I was funny. They liked my humor. That was a bonding moment. They liked my content. One person said to me," I like what you have to say, even though sometimes I don't want to hear it, because it's harsh." And I thought that was the best comment ever, because I thought I was more genuine. Then the last thing was my speaking sessions, this is going to sound boastful, it's not meant to sound boastful, it's meant to convey a point, my speaking sessions were full. Standing room only. The organizers were oohing, ahhing over our sessions. All that goes back to the reputation and the rapport I was able to establish with so many of these people leading up to that event. That's all it was. It was nothing more. It wasn't that my content was great. My content was not original. Nothing I said was original. Nothing. You could Google it and get the exact same thing that I said on stage. That's the honest- to- God truth. So what about me and what I did allowed me that success, allowed me that ability to establish rapport and friendships? Consequently, you should understand that several of those conversations became active deals in our pipeline as a result. Not because of the trade show booth, not because of what I said on stage, because they were actually finally able to talk to me and maybe validate who they thought I was. So that all goes back to how you connect with people. That's it. That's my story. That's today's session. I thought to myself, who do I know who really understands this? Who understands humor, who understands intentionally constructing conversation or storytelling or humor, to physically establish a rapport with a prospect so that you can start building a relationship and start building trust? And of course, I thought to myself, we need a half sales guy, half standup comic, all parental disappointment. If you don't know who I'm talking about, let me help you out. It's Jon Selig. Jon, my friend, welcome to the show.

Jon Selig: Darryl, thank you for having me. Not only do I qualify because I know a lot about all that stuff you talked about, I was also available on short notice, and therefore, here we are. And I'm grateful for that.

Darryl Parrel: This is true. It's so funny, because I had my producer, Daniel, who you hear me talk about all the time, come up to me and he goes," Darryl, you just got back from the UK, but you know what, we're all out of podcasts, and we need more." And I'm like," Okay, what do I want to talk about?" And then I'm like,"Who are the right people?" And ironically, I had a handful of topics, and this being one of them, and Jon was available.

Jon Selig: There you go.

Darryl Parrel: But I did book four meetings in a row, so my producer will give you a little less grief. So that was great. But so Jon's the guy. I love Jon. Have you guys actually met Jon? I don't want to give your story, Jon. I'll let you tell the story. But what I like about Jon is he actually doesn't take himself all that seriously, yet he does take himself seriously. He is a master of his craft, but he understands he is a constantly evolving practitioner of what he does, and some of the stuff he does will not work, and he understands that, and he accepts that, but he also understands it's the iteration, it's the refinement, like any standup comic, that gets you that ultimate success. And then of course, what you've done, Jon, that's unique in this industry, is you've actually taken this and you've actually applied it to your own business. So why don't we just start with that? Normally, I like to get right into it, but I think you deserve special attention because of what you do. It is so unique. So tell us a little bit about what you do, how'd you get in it, and then we'll get into some of the lessons to learned and advice you can share with us.

Jon Selig: I like to just think that I deserve special attention for millions of other reasons other than what I do, but we'll leave that for another podcast, I suppose. But with that said, a little bit about the backstory, and once again, thank you for inviting me, it's great to do this with you, and welcome back to North America, by the way.

Darryl Parrel: Thank you.

Jon Selig: The one last thing I need to add is that people, they weren't only seeking you out in London because of your knowledge and your humor, but they also want to know where to get that awesome smoking jacket.

Darryl Parrel: It's true. I was wearing this on stage, and I was actually using the term," Guys, you want to be successful in life, you got a peacock a little bit," and I was using this jacket, and the British audience loved that reference to peacocking. But the reason I do it, honest- to- God story, Jon, is because when I wear a jacket, a loud jacket like this, on stage, and I do public speaking, and people hear what you say, and they're like, yeah, and they're thinking, but they're in the 14th row, in the middle of the aisle, and they're not getting out, and they're focused and everything else, and then the session ends, and I'm gone. So what happens is, later on that day they see me walking around the show, and what it is, they don't know who the hell I am, they block me, the ugly fricking Canadian with the pasty white skin and the white hair, but they see the jacket, and then they connect it together, and they stop and they say," You were on stage, and you talked about this. Can you help me understand this better?" And so the jacket actually leads to more deals in the pipeline. Honest- to- God truth.

Jon Selig: I'm going to segue. I'm going to skip about me, and let's just talk about that particular topic. The idea of being different and standing out is really tied to what I do. But I just came back from a conference, which you might be familiar with, but it's really the same as every other conference. There's a lot of people there who want to be taken seriously, and as a result they dress a certain way, and as another result, they wear what's in fashion. So 50% of the males at the conference were wearing plaid blazers of some kind, or plaid suits. Patterned, checked, blazers and suits. And at that point, you're not really standing out, you're one of so many. And to your point, you are standing out. I have a friend named Richard Bernstein, who's at Salesforce right now, and he wears bow ties everywhere he goes. And he wears, also, kind of peacocky blazers, as well, and at a conference, he stands out, and people know him as a result. And he's a great networker, and people just like him, because he's trying to be different in that sea of sameness. The B2B space, everyone wants to be taken seriously, everyone wants to be seen as highly credible, and they don't think about how the way we present ourselves, both from a fashion sense and from a personality sense, they've kind of pushed that aside because they want to get that pitch down. They want to get that seriousness down that they feel they need to convey to customers, prospects, investors. So kudos to you for upping the fashion game, upping the personality game, and making yourself stand out, both online and offline.

Darryl Parrel: Well, funny story, an online colleague, woman named Eden Hansing, she did a post the other day, and it was remarkable. She tagged me on it, only because she's heard me talk about this very topic, about how you present yourself matters. And it's not just what you wear, but it's also your gear. Do you look good on camera? Are you framed? What's in the background? Are you lit? Do you have a reasonable microphone? And this is if you're settling. Everything I've just said totally matters, and that's what she's doing. Her point was, it was brilliant, what she did, she had a before- and- after picture, and it was like," This is me a year ago," it was a closeup of her face," And this is me now." Same woman. Same hairstyle. And the difference was the picture from a year ago was kind of cloudy, if you will, kind of low res. This one was high res. She was a little more done up. She had some makeup on that she clearly didn't have before, and she had a slightly different attire. But again, you only see her from the shoulder up. And her point was this, her point was," People used to tell me that how you look and feel and appear to your audience matters, and I used to blow it off by saying, yeah, whatever, that's so old school, we're all hip and happening casual. This is our vibe. This is our tribe. It's all good. We understand each other." And she goes," But I've gone out on my own kind of thing and I've realized that I get so much more traction when I look like a pro." And it was just a before and after, it's all it was, and she tagged me, which was very sweet of her because I've said the same thing, and she got it and it had such incredible traction on the conversations and not everybody agrees, but the reality is that we make judgment decisions very quickly just based on appearance first and foremost, followed by what you say out of the gate and how you disarm people or engage people before you ever get to the actual reason why we're having that conversation. How do you teach people to do that, Jon?

Jon Selig: I mean, if we, and that was a hell of a segue, by the way, I'm glad you drove it back to the original point of the conversation, which I detracted us from. In short, comedians have this ability to be relevant and credible and trigger emotional reactions within that 12 second span, which you highlighted earlier. If we break down an opening joke of a standup comedian set, especially if you don't know them, because the vast majority of comedians on the planet, we've never heard of, we've never seen if we're at a club. Netflix specials, we're tuning in because we know who they are and their audience has already bought into them so they have the liberty of starting their set off with a minute long story. But if you're a comedian that comes on stage and no one knows who you are, they have to make you laugh in 12 seconds, otherwise they're faces will light up, but not because you've made them laugh, it's because they're on their phones. So we have about crosstalk everybody ever goes to watch standup comedy. When we are on stage and you are on your phone, we see that blue light on your face. That means you're bored. That means you're disengaged. And we die a little bit inside, even more than some of us already have. Which is why so many people do standup comedy in the first place. That said, you have about six seconds to say to the audience something of relevance that matters to them, and then you have another six seconds to get them to laugh. An emotional reaction. And so if we can be relevant, incredible, within those short periods of time, whether it's over a cold call, whether it's on LinkedIn in a message, whether it's in an email, we have a much better chance to get our audience to respond to us. It doesn't have to be a big laugh, but as long as it's, I'm going to keep reading more, I'm going to keep listening more, or I'm going to smile, or I'm going to engage. That's really what we're looking for.

Darryl Parrel: It's funny that you say that, because I hadn't thought about it that way until you said it, and then I'm thinking back to all the standup comics I've watched and I'm not stealing anybody's line because of course I can't remember one on the fly, but if I had to paraphrase something I see on a regular basis, it would go something like this," Hey, there folks. My name's Darryl. I recently got married. That's right. She's got two kids." And so right away, stop there. What do they do? They just established who they are and why you can relate to them. I've been married, I've got two kids, or I got into a family that was preexisting. So that's like six seconds to who are you, to your point. Then it's usually followed by a great one liner. I've gone from being a flashing, hippie, happening, bachelor, to being told what underwear to match with what socks, thanks to my wife. Or whatever. That was a bad joke. You get the idea. But it's a punchline that they use. It's exactly the formula you just described, six and six. Establish who you are, establish a point of reference to connect, and then make them laugh. And that's the formula. That's brilliant. So that's exactly what you're doing. That's hilarious. You nailed it. That's the formula.

Jon Selig: It is. And just to be clear, comedians don't have punchlines every 12 seconds, but crosstalk.

Darryl Parrel: No, but it was the opening. You're intentionally starting in conversation to engage, whether it's 12 seconds or more, that's probably secondary, but you're intentionally engaging them.

Jon Selig: Well, no, actually, I like to think that in standup, it's very healthy to have a couple of quick short jokes to open up your set, because if the crowd is onboard, they're going to trust you when you start to go into some stuff that isn't quite a short form. So the moment you start to tell them a story they're listening. They trust you. They'll like you. You're relevant. You're credible to them. If we look at attention spans over the last 10 years, since we all have about four devices in our faces all the times, people's attention spans have really shrunk. Their focused attention span is now like eight seconds, and so if something doesn't grab our attention within those eight seconds, we're drifting away and we're deleting the email. We're looking at our cell phone as the prospect is pitching us. And so we have to be relevant right away. We have to demonstrate that relevance, the words, phrasing, empathy for the audience, and then if we can, what I call subvert those expectations and get them to laugh and trigger them, we're going to get that conversation going.

Darryl Parrel: Some of what you're alluding to, I have generically many, many times referred to that as personalization. In other words, why does it matter to them? So they'll continue to read this. The one presentations I gave in the UK was about stop sending shitty sales emails. We talked about why your emails are awful, whether it's your subject line or your format on your body. We talked about different formats. We used to Josh Brown example as one of five examples, the TTTT, the first one being trigger." Hey, Darryl, I see you're hiring some new sales reps."" Oh my gosh, how did you know that?" So you've triggered me, you've got my attention, because it was personalized. But you're much more specific. I'm being a little general on that. So what advice can you give our reps to achieve that connection fairly quickly, whether they're using email or phone or social, any advice you can give is that they can test out and see if it improves their response rate.

Jon Selig: I'm going to disappoint everybody. This isn't going to be super secret sauce, this is just what I view as common sense and it's kind of the intersection, again, between sales and standup. If we want to be relevant to our audience, we have to understand who they are. So if I'm performing in a comedy club and everyone in the audience has hair that's much grayer than Darryl's, maybe it's best I don't tell a bunch of jokes about TikTok or using slang that's gen Z folks like to use. They're not going to get it. It's all about who is our audience, who are reaching out to, what's relevant and important to them, what are they trying to achieve? I'm talking more in the business sense now. What are their objectives? What's their desired end state? What are the roadblocks that they typically struggle with on route to that desired end state? Who are their key stakeholders? Who's affected by those road blocks? What emotions are set off by those roadblocks? And then which of those road blocks can we remove for them? Let's talk about if they don't remove those roadblocks, that one roadblock that we can remove, what are the possible scenarios, what are the impacts of not solving that problem? Because this is all that relevance specific to their role and them wanting to get to a desired end state, and if we can be show that we really have a good handle on their world and be subject matter experts and demonstrate that I can help you get there just a little bit faster based on the fact that what I do can help you remove this one little roadblock, they're going to be more open to chatting with us. And of course it has to be done in a way that obviously gets their attention pretty quickly.

Darryl Parrel: All right, so let's break that down a little bit. If you today are using a sales engagement platform where all the email or social touches are automated, you just set it and forget it, built on a template, and you're wondering, why am I not getting great conversion rate? It's because that approach is wrong, because it literally does not do what Jon just told you to do. You need to make sure all your outreaches are personalized. That's number one. It was interesting, I shared this stat on stage in England, we did a survey about a year, year and a half ago, of 2000 B2B buyers, and we said," What do you value most?" Product knowledge was number two, competency in the knowing my life, my industry, number one. So you don't need to have all the answers around your product, but you need to know me. And that's exactly what Jon was just saying. You have to actually invest time to do that. You need to time block. You need to actually research the industry. You don't need to be an expert, but you need to be able to at least talk about their issues. The third thing, what we see, is when we talk about that, knowing their issues, most reps default to the big picture stuff." Well, you got a big sales number to hit, don't you Mr. Head of Sales, or Mrs. Head of Sales," or whatever. That's not what keeps them awake at night. They know that. They knew that when they took the job. That is totally not what keeps them awake at night. What keeps them awake at night, and Jon was talking about this, the stuff that's personal, that's happening to them right now is, I use the term recency. The example I was giving to some people over in the UK, and they were talking about some qualifying questions up front, was, I said," In the last 72 hours, what have your reps done, one, two, or three things, that have bugged the living crap out of you?" And they'll go," Oh my gosh, they can't update salesforce. com. They can't stick to the system and their discovery sucks." That's their pain, not the big picture items, that, the recency is emotional. That's what you talk about right there. So Jon Love that.

Jon Selig: Can I add one thing to that, actually?

Darryl Parrel: Yeah, you can.

Jon Selig: When I work with sales teams, in short I'm getting them to write jokes that roast their prospects pain. And I'll say to them," Okay, guys, I want you to tell me..." I like to facilitate their pre- work where I ask them these kind of questions. What problems do you solve? Who's affected by them? How does it prevent them from getting to their desired end state? And the most common answer to, what's going to happen if they don't solve the problem is they're going to waste time and money, or they won't be able to generate more revenue. Yeah, that is true. I don't want to call you a liar. But can we get to those root causes of what's causing waste of time and money? crosstalk. Not just more specific, can we get really, really granular, because the more granular and subject matter expertise you can show your buyer that you are, the more seriously they're going to take you, whether or not the email is even memorable. The other thing I want to highlight is the term personalization. I think everyone has a different idea of what it means. I think you use it in a way that means something more to me, but some people feel that I have to go pawing through everyone's LinkedIn profile like a nosy raccoon through someone's garbage to figure out, you went to college here. And I think that's even dead, but just, I saw you were recently on this podcast and I listened to it and it was great. There was this whole idea of stroking people's egos, which, don't get me wrong people have egos and they love to be stroked, but I don't know, if I'm a busy executive, just cut to the chase on why I should take the time to keep reading this email. I'm curious to know if flattery works that well. I don't use it, and maybe some people do. But in short, there's this whole idea of saying we got to make things hyper personal and show this person we know them, not know their role, but know them as a person. I always question if that's a good use of time. What do you think there?

Darryl Parrel: Flattery does work for some people. I even talked about that on stage. It could be in a subject line of an email, congratulations on your recent funding, or congratulations on your promotion, or congratulations on hiring more reps, or what have you. But I wouldn't use it for flattery per se, to stroke their ego, I would use it just to trigger them. Again, they're aware, they know, they've done some studying on me, I'm going to give this person a few more seconds of my time to see what they're all about, what they're asking. That's about it. Let me ask you Jon, we're out of time, but if I'm listening to this and I like where everything you're saying, and by the way, folks, you should because the stats show this is literally what your people want you to do, and the stats show from a behavior point of view what Jon's doing is literally what's going to help you get more conversations and build your pipeline up, and this is a skill, which is why you have to practice it, which is why comics tour the country and they practice their material until they get it great and then they go national and they appear on the Tonight Show. Which, by the way don't read into this, Jon has never appeared on the Tonight Show. Where should they go to connect with you, my friend?

Jon Selig: They should go to two places. LinkedIn is really a great spot. J- O- N- S- E- L- I- G. There is an H in Jon, but it's both silent and invisible. If you didn't get that joke that means it's J- O- N, there is no H. Or jonselig. com, and if you go to that site you'll learn really how salespeople need to use the processes, skills, and methods of standup comedians to better connect with their audience. Really if we look at standups and salespeople, they need to use the same approach to better connect and that's really what I help show sales reps to do through the process of writing humor specifically for their prospects.

Darryl Parrel: I want to end on that, in the sense of he made a really powerful point there. Processes. Comics, for the most part, are not just funny all the time naturally, there is a formula. They follow the formula and they refine the formula. That's why you need to work with people like Jon, so you learn the formula. With that, we're out of time. My first episode back from the UK, I had fun. Thank you, Jon. I look forward to catching more of your comic routine. But in the meantime folks, if you'd liked today's show, tell a friend or two, and especially tell them because Jon's here and Jon's funny as hell. My name's Darryl Parell. I'll talk to you guys soon.

Jon Selig: Thank you, Darryl.

Darryl Parrel: Take care. Bye- bye.


What’s the secret to being taken seriously? Stop taking yourself too seriously.

In this episode of INSIDE Inside Sales, Darryl is joined by Jon Selig, a rockstar sales guy turned stand-up comedian, to talk about using humor in sales as a way of establishing rapport and connecting with your prospects. They also delve into the importance of being different, challenging the stuffy dress code, and upping the personality game as sure-fire ways to make a memorable impression.

Subscribe now to learn how stand-up comedy lends itself to sales and how you can laugh your way to closing your deals.

Today's Guests

Guest Thumbnail

Jon Selig

|Guy Who Helps Sales Reps Understand Buyers Through the Lens of Comedy at JonSelig.com