Welcome to Modern Sales

What Joke Writing Can Teach You About Sales with Jon Selig

Share on facebook
Share on twitter
Share on linkedin
Even though it may seem like a stretch, it's true: the process of writing jokes can teach you a lot about sales. It forced you to think about who you're talking to, what's important to them, and what their everyday life is like. In this episode, you'll hear from Jon Selig, a standup comedian and sales trainer who helps sales teams write jokes that connect with their prospects.

Jon Selig’s website
Jon on LinkedIn


What Joke Writing Can Teach You About Sales with Jon Selig:

Full Transcript

Jon Selig:
As I started in standup, I was like, “Man, this is like selling. This is like going to a meeting in a boardroom with a group of people whose arms are folded and I need to get them to change their body language and attitude towards me really quickly, and if I don’t, their faces will light up, but not because they’re having a great time but because they’re on their phones,” because when we are on stage in a comedy club, we can see people on their phones, and that’s when you know that you’ve lost them, so I always found there’s a tremendous amount of parallels between selling for a living and being a standup comedian for practically no living whatsoever and I decided to tie those two experiences together and help salespeople understand more what they can learn from standup comedians, but also how they could use the joke-writing process to really better relate to their prospects and connect with them and start more conversations with them.

Liston Witherill:
That’s Jon Selig and he thinks that an important skill you need to be effective in sales is comedy writing. Yes, I did say “comedy writing,” you heard right, and even if you don’t feel funny or you’ve never been the funny one in your family or group, it’ll still help. Here’s the thing: Being funny is all about context. You have to understand your audience to make them laugh. You have to know what their day is like. You have to know what frustrates them and what they really want but feel they can’t have, so the process is the important part, not the being funny part, but it sure helps.
Jon knows. He sold technology for 12 years, then went on to do standup comedy. What he found was a huge amount of overlap between the two. Every audience has a short attention span and if you can’t capture it, you’re out, booed off stage or booed out of the inbox. A single well-placed joke can highlight a problem you solve, grab attention, trigger an emotional reaction, and make you more likable in an instant. In this episode of Modern Sales, you’ll hear from Jon Selig about how he’s helped sales teams at big-name brands be funnier, more relatable, and get more responses to their outreach.
Welcome to Modern Sales, a podcast that’ll help you sell more by understanding how people buy. I’m your host, Liston Witherill, founder of Serve Don’t Sell, and I dig through academic research, interview people inside and outside of sales, and nerd out on psychology, economics, and neuroscience to figure out how people make decisions, and I am on a mission to change the way 100 million people sell so that buying B2B services can feel as good as the summer sun on your skin when you’ve been locked up due to a global pandemic. Wouldn’t that be nice?
If you’re listening on Spotify, hit that Follow button so that you don’t miss an episode, and if you’re on iTunes or Apple podcasts, please subscribe and leave an honest review. It helps me get the word out for the show so we can together change the way 100 million people sell. Thank you in advance for your help. Now, to the show.
How can comedy writing teach you to have a quicker wit, be more interesting and relevant to your prospects, and actually make the whole process enjoyable for you and for them? You’ll find out in my conversation with Jon Selig right after this short break.
Welcome back to Modern Sales. I’m Liston Witherill here and I am with Jon Selig, who is the person behind Comedy Writing for Sales Pros. Jon, welcome to the show.

Jon Selig:
Thank you for having me, Liston. Good to be here.

Liston Witherill:
Yeah, you’re absolutely welcome. I’m glad that you’re here and I want to hear a little bit about this comedy writing thing for salespeople. Where does that come from?

Jon Selig:
Look, it comes from a weird amalgamation of my career experiences. I sold both enterprise software as well as professional services, a world with which you’re familiar, for about nine years. I sold some SAS and some other professional services after that, so 12 years in sales, and at a certain point, I was, let’s just say, disenfranchised with selling, and “Is this going to be really what I do for the rest of my life?”
I started doing standup as a creative outlet and I got very addicted to the process really quickly and as I started in standup, I was like, “Man, this is like selling. This is like going to a meeting in a boardroom with a group of people whose arms are folded and I need to get them to change their body language and attitude towards me really quickly, and if I don’t, their faces will light up, but not because they’re having a great time but because they’re on their phones,” because when we are on stage in a comedy club, we can see people on their phones and that’s when you know that you’ve lost them, so I always found there’s a tremendous amount of parallels between selling for a living and being a standup comedian for practically no living whatsoever and I decided to tie those two experiences together and help salespeople understand more what they can learn from standup comedians, but also how they could use the joke-writing process to really better relate to their prospects and connect with them and start more conversations with them.

Liston Witherill:
Once you reach Dave Chappelle-level heights, you will be able to just collect everybody’s phone at the door, you won’t have to worry about that one problem. Now, I want to get into the joke writing process and how that can be applied to sales, but quick question on probably at least a few listeners’ minds at this point: Do I have to be funny to understand and apply comedy writing?

Jon Selig:
The short answer is no. I believe that the vast majority of us, probably 99% of us are not sociopaths who do have senses of humor and do why we’re laughing at things and can at least learn to repeat a joke that we find funny, and so if an entire sales team uses one joke that customers just find really funny because it really triggers something important to them that they’re dealing with on a day-to-day basis that they struggle with and they can go, “It’s funny because it’s true,” and they laugh, I believe that most people could learn to repeat that one joke.
Some might go, “That’s not my style,” but even if people aren’t funny in the moment, which is not something I teach, that’s a hard thing, to get people to learn how to all of a sudden think funny and to be spontaneously funny in the moment, that’s not something that I teach, that’s more of an improv skill, and that also comes from our intelligence, our life experience, our personal experiences, professional experiences, that is not taught, however, even if people aren’t funny, they can learn to make a joke their own and deliver it in a way that lends the results they’re looking for with their desired audience, AKA the prospects.

Liston Witherill:
One of my favorite comedians is Ricky Gervais, and if anybody listening to this really wants to nerd out on the joke-writing process, you can hear him describe how he comes up with some of these bits and also all of the extremely rational and not funny thought that went into writing the jokes. He’s sort of like, I guess, a thinking man’s comedian in a lot of ways, so anyway, I do understand what you’re saying, so walk me through the joke-writing process: What are the steps and how do I start to apply that to sales?

Jon Selig:
I think the most important thing that everybody who wants a joke to hit needs to understand is who is my audience, and in case of salespeople, it’s who are our prospects, and we need to understand what’s important to that audience: What are they struggling with? What are they fearful of? What are they frustrated with? What do they love? What do they desire? Because I think the biggest challenge that a lot of sales reps have today in a very crowded, noisy environment is twofold: Getting our prospect’s attention and starting a meaningful conversation with them.
If we look at the most popular standups out there, they’re joking about highly relatable things, like food and dating and marriage and doing the laundry when we want to go to bed, these kinds of things, and there’s some other comedians who cater to very niche audiences, so there’s loads of ethnic comedians. There’s comedians who perform for audiences who have certain nerdy interests, so for example, there’s some people who do superhero movie comedy and jokes just about Marvel and DC movies and for a very niche audience, but the point is, those comedians really understand their audience, and at that point, it’s their job to demonstrate to their audience that, yes, we are masters of our own domain from a subject matter/expertise point of view, not the way that that Seinfeld episode referred to the term “master of their domain,” but really being subject matter experts in whether it’s superheroes, whether it’s about dating, whether it’s about relationships.
At that point, once we know who our audience is and what’s important to them, we have to figure out how are we going to present that detailed subject matter expertise, so again, if we were to take, let’s say, something that our audience struggles with, we would need to write everything we can. Like you said, the same way Ricky Gervais does it, he just gets down mundane thoughts, observations, insights into a particular premise or problem, and he just gets it all on paper, he captures it, and at that point, I mean, I can tell you how I write jokes or how I even…
Let’s do it like this. Let’s talk about how I teach people to write jokes. Sometimes if you’re funny, it’ll come to you with a smart-alecky wrapping around it, but that’s not everyone’s cup of tea, some people aren’t sarcastic, some people don’t even have insights, right? But I think if you can’t observe something and describe it in a very detailed kind of way, I think you’re going to fail at being creative and funny. I think you can still be able to repeat joke and come off as funny, but if you want to create jokes, you need to be very insightful and document everything about a particular topic.
Once we’ve defined the premise of what we’ve expressed ourselves around that topic, quite simply, I’m a big fan of identifying words and phrases that are impactful, so whether they’re verbs or adjectives, maybe some unique phrases or colloquialisms. The expression “in the dark,” it was something that came out of one of my workshops where the sales reps taking the workshop said, “Oh, if our customers don’t solve a problem that they’re struggling with, they’re going to be in the dark,” so we captured that. When I say “verbs and adjectives,” what actions are these problems taking? Who or what else is taking it? Are there some good adjectives used to describe the problem beyond just the word “frustrating”? Because “frustrating” could be used to describe any problems, so there’s all kinds of ways that business people like to describe their problems.
I then like to find other ways to say all those words and phrases we just outlined, like are there synonyms? If we use the word “robust,” to describe something, what’s another way to say that something is robust? Let’s toss it out there to you. Let’s get you participating.

Liston Witherill:
Oh, okay, we’re doing a live workshop. Okay, I’m ready.

Jon Selig:
Yeah.

Liston Witherill:
What’s another way of saying robust? In what context?

Jon Selig:
“We lack robust reporting.”

Liston Witherill:
Mm, I’d say “complete,” I would say…

Jon Selig:
I gave you a tough one. I’m sorry for that.

Liston Witherill:
Yeah, “robust” is a pretty specific word.

Jon Selig:
Yeah.

Liston Witherill:
One of the things, though, that I just wanted to interject is I have a background in marketing and I’ve written a lot of copy in my life and that actually turns out to be something I spend a lot of time on doing in my own business. One of the things that I always tell people about writing copy, if and when I’m ever asked, is “Specificity rules the day. You have to be specific about it. The more you use words that people are either attracted to or repelled by, the more likely it’s going to be effective. It can’t be for everybody.” Do you find that jokes tend to be better when they’re more specific or does that not really apply to sales teams?

Jon Selig:
I agree with you. You hit the nail on the head and that’s why I mentioned when I tell sales reps to describe the problem that they solve in their customer’s words, get rid of the word “frustrated,” because it’s this generic catch-all word that can be used to, like I said, describe any business problem. How else can we describe this problem? It’s, and again, I don’t have a specific problem coming off the top of my tongue, but the more specific we can get with insights into that problem and demonstrate that we understand the specific problem we solve for them, the more it’s going to hit the mark when it’s in the form of a punchline.

Liston Witherill:
Yeah, and so for frustrated, I would think of synonyms like “aggravated,” “pissed off,” “upset,” “losing sleep,” these are common things that you would think about in terms of copy that you’ve read before.
So, I have an observation, I have to start by knowing who my audience is, I have observations about who they are, and then I start to write those observations down and try to transform them into things that are maybe more specific or just more interesting in the way that they’re phrased. What do I do next?

Jon Selig:
Yeah, and so let’s say, for example, let’s come back to that word “robust.” The word “robust” can be used to describe perhaps someone’s reporting solutions, someone’s data warehouse and the type of analytics they can get out of it, but it can also be used to describe tons of other things in a very different realm, so whether it’s a red wine, whether it’s a dark roast coffee, whether it’s an economy, whether it’s someone’s personality, we can start drawing parallels between two things just using one what I call “fulcrum word” or “impactful word,” and that’s the easiest kind of jokes to make are things that compare one thing to another, so that’s the really simple way to do it, but something that I’ve been meaning to get to is that there’s a lot of words and phrases that can be taken more than one way. If I toss out the word “draft” to you, how do you interpret that word? What does it mean?

Liston Witherill:
Well, it means lots of different things. It could mean to draft behind a vehicle, right, to be in its tailwind. It could mean a first version of something that you write or a first version of a podcast, like some people might think this is. It could mean, yeah, lots of different things.

Jon Selig:
Yeah, it means beer, it means there’s the military draft, there’s a sports draft. That first one you gave us is the first time I had heard. The word “season,” it can be used to describe a time of year, how we flavor our food, experience, so really, what I encourage everyone to do is after they’ve taken those other steps that I’ve laid out is to figure out which words and phrases can be used or be taken in more than one way by the listener because good jokes are predicated upon surprise, among other things, but a real twist, a left turn is what makes people laugh the most, and things that mean more than one thing or can be taken more than one way usually are the fulcrums of the best jokes, in my opinion.
At the end of the day, jokes are formulaic in nature and I teach about five different formulas and the idea is to once we’ve created all those raw materials that I just described, at that point, we need to assemble them and we use the different joke formulas as templates and it becomes a bit of, I don’t want to say a plug-and-play exercise because there’s an art to it, it’s not that simple, but those joke frameworks are good starting points to take your thoughts, observations, comparisons, and package them up and then figure out, “Okay, if there’s something funny in here, now we have to test it out on our different audiences, practice it, figure out the timing and keep iterating and editing it down to the point where it’s short and there isn’t even a wasted syllable on the joke.”

Liston Witherill:
How do you know when you get to that point?

Jon Selig:
There’s two answers to that, there’s from a standup comedian perspective and a sales perspective. From a standup comedian’s perspective, I mean, before we entered into a global pandemic, I’d go to all kinds of open mics to test out my ideas. Sometimes it wasn’t the jokes themselves that were funny, it was the ideas, right? Because when I’m on a stage, people are watching me, I have body language. People are there specifically because they want to hear something funny. I can use my facial expressions, I can use my tone of voice, and the mic in a certain way, and I have a lot more tools at my disposal to really communicate my ideas and why they’re ridiculous or absurd or funny to me.
Of course, the first time I would do it, I would express myself, and if it’s a room of 10 faces, who again, maybe they don’t want to be there because maybe they’re supporting a friend, if even one of them is smiling, I feel like, “Okay, there’s something here. I’m going to work on this next time and just try and listen to my recording on my iPhone and go through it and rejig it and figure out, am I giving them too much information? Am I giving them not enough information?” Because the audience needs to take in X amount of information so that they can process whether the punchline is going to be funny. You have to provide them with enough information in the setup. The setup can be one sentence, it can be two sentences.
In sales, though, we don’t have that luxury, so it really comes down to the joke itself. We’re not in front of people, people aren’t there to hear us laugh. If I cold call you, I have like 12 seconds to see if I could make you laugh and say something that’s hyper relatable to you.

Liston Witherill:
Right, and most people, I think, don’t want to spend that 12 seconds testing out a joke.

Jon Selig:
They’re going to fail a couple of times, but they could try it on their coworkers, they could try it on a couple of prospects that may not matter that they know aren’t going to buy anyway, may as well just practice, but I think the reality is if you can find a joke where at the core something is funny and figure out how to shorten it down, you can eventually figure out, “How do I lead the joke with something that’s a value and relevance to the prospect in the setup?” and then twist it on a punchline that surprises them and gets them to go, “That’s funny because it’s true. How can I help you?”

Liston Witherill:
Tell me about coming into this. You talked about Seinfeld’s Pop-Tart video and his process to come up with this one bit about Pop-Tarts, which is classic Seinfeld, where he takes the utterly mundane and does a little bit of wordplay on it and comes up with what turns out to be like a four or five-minute bit all about Pop-Tarts.

Jon Selig:
Seinfeld, what he seemed to do was he just decided to, sort of like I described earlier, I’m sure what he said about writing a joke about Pop-Tarts, he got everything down on paper that he felt was either interesting, great, boring, annoying, everything to do with Pop-Tarts, he just dumped on a piece of paper. Some comedians do it in a Word doc, some just choose to get up on stage and do a verbal dump on an audience and then figure it out. I like writing stuff because I think when we’re looking at our pages, we’re able to see words and phrases that pop out at us.
But really, what Seinfeld did was he went through this process to, again, describe everything he thinks of and feels about Pop-Tarts, and then just boil it down to some of the more succinct, absurd realities of Pop-Tarts, and Seinfeld’s not always a traditional joke writer and he has his observational style and he injects his own personality to it, but at the end of the day, he boiled that entire bit down to, again, a few key observations that he finds ridiculous and finds ways to reframe them for his audience. Does that make sense?

Liston Witherill:
It does, totally.

Jon Selig:
Yeah.

Liston Witherill:
Earlier, when you were talking about focusing on just the material, because you’re not going to be there to present it, of course, one thing you could do if you’re in sales is record a video if you want to use it over email and then you have, as you said, other tools, your tone of voice, your body language, how you move, your physicality, but I love this comedian, Ali Wong, who I’m sure you’ve heard of, who’s totally blown up in the last few years.

Jon Selig:
Yep.

Liston Witherill:
She said her process for testing out her material is she goes and does it completely monotone and almost whispers it at open mics and the reason she does that is she wants to test out is the material good absent any of the other stuff, absent her moving around, being animated, like she sticks her tongue out and pulls her skirt up and shows her underwear during her set. She doesn’t do any of that in order to test the material, which I thought was pretty interesting.

Jon Selig:
Well, here’s a little story: When the pandemic began, I was just throwing some jokes up on Facebook and even on LinkedIn and some of them were getting really good reaction and I was invited to perform for some sales teams, and so I was like, “I got to keep it clean. What do I have that’s clean?” and I went, “Oh, man, some of those jokes did well on LinkedIn. Some of those jokes did well on Facebook. Let’s see if I can inject some of my personality as I deliver them and see what happens with them,” and most of them got better reactions than I expected. I thought they were cute jokes, but it turned out people were really laughing at them.
I think that’s a great approach because at the heart of a standup comedian’s act is their words. If you can’t write, you’ll never really be able to make an audience laugh and I think salespeople really need to take the time to think about, “How can I better relate to my prospects?” because at the end of the day, we’ve never had their jobs, we’ve never used the products we sell, we’ve never worked in their industry, and I’m generalizing, but we have to find that connecting tissue, and a good joke is really a great way to show them you know them and gain some credibility and some likability, and of course, trust.

Liston Witherill:
Dumb question: Why is it important to make my prospects laugh?

Jon Selig:
Wow, where do we begin? Because the reality is because you and nine billion other salespeople are trying to get their attention. It’s a pretty noisy marketplace out there, right, so if you’re going to get them to even look at your subject line of an email, it needs to inspire a little curiosity, and if they open it, you want them to laugh so that they remember it because that’s an emotion that we remember is when something makes us laugh.
At the same time, if I cold call you and you answer the phone and I can make you laugh, it’s just going to diffuse all the tension and you’re going to be far more receptive to hearing what comes next: “This person made me laugh. I like them. I’m going to give them another 12 seconds.”
Those, to me, are the two main reasons why we want to make our prospects laugh. It’s so corny, but people buy from people and injecting our own personality and then giving people a good time and showing them that we’re fun, I think it might not get the deal done, but it’s the tiebreaker.

Liston Witherill:
Best opening line I’ve heard for a cold call, and this, I can’t take any credit for it, and I wish I could give credit to the person who deserves it but I don’t know who originally said it. He calls up and he goes, “Hey, it’s listed. I’m here to sell you something,” and it’s exactly in opposition to what most people would think the reputation of salespeople is like: They’re going to twist the truth and hide around and soft pedal and it’s just right in your face. I really love that line.

Jon Selig:
What’s good about it is two things: It’s a pattern interrupt and it’s a truth.

Liston Witherill:
Can you share one joke that you’ve used maybe that’s relevant to salespeople, maybe you tell it in your training, I don’t know, and break down how you arrived at it?

Jon Selig:
Yeah, I was given a reference for one of my workshops from the CEO of a company in Toronto called EventMobi, and on camera, he said this was unique and it was refreshing, and so when I was cold calling sales leaders to introduce myself, I’d say, “Hey, Liston. My name is Jon Selig and this call is like a craft beer because it’s unique, refreshing, and ice-cold,” that one joke has built my pipeline and gotten me deals. That’s a simple one. I mean, all the jokes that come out of my workshops again are hyper-specific to the set of prospects that these sales reps dial into.
I worked with a company called Fleetcor and they sell prepaid fuel cards and a major challenge is because a lot of companies don’t have credit, so we wrote a joke about the pain of being a small business with no credit and the joke goes: “Being a small business credit is like trying to bribe a police officer because it’s risky, you can’t mention it to anyone, and you can only pay with cash,” so we’re highlighting some points and some of the realities of a situation that sucks for the business, and it’s like, “Hey, glad you laughed. This is how we help alleviate that problem. Can we talk?”

Liston Witherill:
Love that. You have a workshop that you run. Tell us a little bit about your workshop.

Jon Selig:
Traditionally, I’ve worked with sales teams, and it’s part crash course comedy writing, part sales training, and we take the time to really break down who that audience is, what problems that the sales team can help them with, what are the impacts of not solving those problems and who’s going to be affected in their universe by it and taking all that and going through that process, which I described to you earlier on, and the goal is to get breakout groups to collaborate, to write jokes, and then kind of test their jokes on one another in an open mic format, and most are going to stink, that’s the reality, but there’s always a few that come through that are gold.
Obviously with COVID, I’ve been forced to move from an on-site flavor to now a remote flavor, and I’ve broken it up into multiple sessions, which I think is actually going to be super positive because great jokes don’t get written by amateurs in half-day sessions. People need some time in the shower or on a walk to think about their creativity and their ideas and bring those ideas back to the next session, so I’m excited for that.
I work with them in a variety of ways. I can do just a keynote, I can run, like I said, a six-hour multi-session workshop, but I’m also in July going to be launching a comedy writing for sales pros versus sales teams and people can just register for live classes, they don’t have to come with their colleagues, although I think that would be great, but they’re going to be part of a small eight-person class and I’m going to guide them through this process over six hours and our goal is to help our peers figure out how to make something funny and for them to help us figure out how something’s funny and I’ll be there to guide everyone through every step of the process.

Liston Witherill:
Great, and one of the things that I thought was really cool is something I saw that you posted on LinkedIn was that you’re doing a COVID-19 relief program, so for anybody listening to this who’s interested in maybe bringing you to their company to learn more about joke writing and how they might be able to apply it within their sales department, what are you doing for COVID-19 relief?

Jon Selig:
Well, what I’m doing for COVID-19 relief is something that I’m not doing very much of on this podcast, which is I’m just going to be funny and I’m going to bring my standup act, which I’ve been doing for the last like two months now. I’ve performed for about 18 different sales teams in their virtual happy hours. They log in, I tell about a half-hour of jokes about how we’ve been impacted by COVID, some sales jokes, but the majority of it comes from my standup back. It’s all pretty clean, pretty tasteful. I want to say “pretty.” It’s all pretty clean. It’s all pretty tasteful and nothing to worry about, sales leaders, I will not offend anybody with anything I say, unless curse words are a problem because there is the odd one that slides in, but in short, it’s just meant to give reps a break from maybe staring at the screen for a Zoom meeting where they have to just listen to all business stuff. It just brings them together a little bit. I encourage them to bring drinks.
I’m not charging for this, and why? It’s really, these are fundraisers, and in short, instead of paying me a dime, I’m asking sales teams to make a donation to a nonprofit that’s supporting COVID-19 relief efforts, just make a direct donation to them. I’m trying to raise $25K, I’m just around the $10K mark now, only 40% of the way to my self-imposed number, and that’s making my sales manager extremely, extremely angry. I’ve been yelling at myself all day in my apartment. That’s really all it is, so it’s not even tied to my workshop. Just invite me on, let me make your team laugh, and let’s raise some money to help those impacted by this ridiculous, awful pandemic.

Liston Witherill:
Love that. Jon, you’ve shared a lot about the joke-writing process. You’ve shared a lot of valuable things about how teams might be able to apply this. If they want to learn more about you or more about the workshop, what should listeners do?

Jon Selig:
Yeah, best spot is jonselig.com, the “H” in “Jon” is both silent and invisible, so it’s J-O-N-S-E-L-I-G dot com. That has all the information about my workshops, about how to get me on board for fundraiser comedy, and a bunch of my content, including my web series, Second Opinion and Jon Hates Sales But Loves Sales Experts is there.

Liston Witherill:
Thank you so much for being here, Jon.

Jon Selig:
Thank you for having me.

Stay In the Loop

Get a daily sales insight sent straight to your inbox – sign up for our newsletter.

Like what you heard? Help us get the word out! Just leave a rating and review on Apple Podcasts. It’ll take you less than a minute and it’ll help us spread the word about Modern Sales.

Subscribe

Get Serve More Weekly, an email newsletter with one article, podcast episode, and stories from around the web. Every Monday.

Up next…

Check out the four sales fundamentals every top performer masters, how to use value-based selling to increase your leverage, and how to improve your remote selling skills as the world becomes more virtual.

And check out the SDS method if you want to improve your sales process.

Share on facebook
Facebook
Share on twitter
Twitter
Share on linkedin
LinkedIn