E19: Infusing Humour into the Leasing Process with Jon Selig, Founder of Comedy Writing for Sales Teams

"If you really want to start learning how to get funnier, just go watch comedy of all kinds. Whether it's a Simpsons episode or a late night talk show...try and observe patterns and timing and absorb that over time." – Jon Selig

What does multifamily and stand up comedy have in common? At first glance, probably not much. But if you think that the rental market couldn't be made more humane with a little humour, you've probably never heard of Comedy Writing for Sales Teams. He spends his time training sales teams on the best way to inject humour and lightheartedness into literally any industry, from housing to software to the funeral industry. 

Our conversation on this episode of Sync or Swim centered all around: 

• What makes something funny or unfunny
• Steps you can take to help sales teams to get to know their audience better and be more relatable
• The importance of empathy in sales

If you liked this episode, be sure to subscribe or follow Sync or Swim wherever you get your podcasts, Google Podcasts, or   
Jon Selig [01:08]
Thank you for having me. It is lovely to be here.
 
Nicolina Savelli [01:11]
So Jon, can you expand on that intro by telling our listeners a little bit about yourself and what you do?
 
Jon Selig [01:15]
Yeah, absolutely. Well, I was in technology sales for 12 years. And that was a really well paid internship for my career in, in stand up comedy. And the thing was stand up comedy is, it's fun, I never looked at as a career because my landlord and the grocery store, do not accept drink tickets as payment for lodging. You know, lodging and food. And really what I felt was when I started doing stand up comedy, this is very similar to sales, I have to know my audience, I have to deliver messaging that's valuable to them that they care about. And what I decided to do was kind of take those parallels, and package them up as an offering to sales teams, so they can understand who their buyer is, why, why we have sales pros matter to them, and how to take all of that and convert into memorable messaging that illuminates powerful business points and gets our buyers to open up to us and make us realize that we as salespeople are both memorable and relevant. 
 
Nicolina Savelli  [02:14]
Right, right. So I mean, you kind of touched on it. But is there anything that you can share why you feel humor is so important in the sales process? You know, you're saying something memorable? Do you think that humor is what makes it memorable for your audience? Or is there is there another or just relatability? I don't know if I'm answering my own question here. But maybe you can expand on it a little bit. 
 
Jon Selig [02:37]
Absolutely. Um, look, there's pre pandemic and there's post pandemic, even before the pandemic hit, I know a lot of sales people. Maybe not in the the property management industry, but a lot of salespeople had gone virtual, and they've gone remote. And as a result, so many salespeople are bombarding prospects with cold email, cold calls, even texts, judging, and they're all kind of the same. They're all, you know, using a lot of similar methodologies to craft their messaging. And I always felt that humor is a great way to stand out. And you you brought up a point about like, just, you know, kind of being relatable or likeable, shall we say, you know, I'm paraphrasing what you said.
 
Jon Selig  [02:23]
I'm a firm believer that not only should we be likeable, or humour can be a way to get us liked, and just, you know, break the ice, shall we say, but if we can tie the humour into something that the buyer is struggling with, which just so happens is an area that we as sellers can help them out with, it's going to make them laugh, it's going to show that we are very relevant to them. And it's going to demonstrate our subject matter expertise through one fell swoop. So prior to the pandemic, you know, comedy writing for sales teams and pros, which is, which is really the two things I offer was meant to help them stand out in that regard. Both from a subject matter expertise perspective from a memorability perspective, and just just help you help sales pros break through the noise. But in this pandemic era, where everyone is stuck at home, and people are a little bit, you know, especially here in Canada, it's winter, we have a lot of reason, we have a lot of reasons to be depressed. Humour is that much more powerful of a tool, shall we say during the same time?
 
Nicolina Savelli [04:24]
It's funny, you mentioned that because I actually you know, as we know, Toronto is going through a little bit of a, an issue with their kind of rentals and their housing right now. And you know, I think leasing agents are having some issues with with getting units rented. And I, I was looking online, just to see what what the the rent rates were going right now in Toronto, potential properties. I signed up not really thinking, you know, I just casually signed up and then I started getting bombarded by this leasing agent via SMS, like just to my cell phone and I, I'd never experienced this before. And I don't know if it was like a COVID revelation that they were like, well, this is how we're going to connect with people or if this is something that they've always done, but when you mention you know if there was some humour or something that was more personable in the messages, rather than just like, is this a good time to call you, I may have been more inclined to respond. But right now I just feel like this person is just like stalking me. And I feel a little bit, you know, a little iffy about it...because I don't know them. But if there was something relatable there that we could connect on, then maybe I would be more inclined to to engage in something like that in a text message form or, or however, sales or leasing agents are kind of pursuing prospects right now. So with that said, Do you think there's any industries that wouldn't benefit from adding humour into the sales process?
 
Jon Selig [05:59]
So there's two ways to answer that question. And it depends on how, I guess deeply you want to think about using humour. So, you know, my whole thing is, you know, I've spoken with some folks at pharmaceutical companies, and obviously, you know, the drugs that they are selling or marketing, shall we say, you know, Lee, you know, are meant to alleviate, you know, terrible things. And, you know, just in talking and to be to be fully transparent, I haven't worked at the pharmaceutical company yet, but I have had some champions, shall we say, in some of them who like what I do, and it's their big bureaucratic places. But just through our discussions, we found other areas relating to the drug discovery process, and to, you know, just what doctors have to deal with, with even the pharmaceutical companies and some other challenges that doctors struggle with, that have nothing to do with human illness or suffering. So obviously, so the reality is we didn't we never want to mock what people are going through, and spit, but there are, at the end of the day, pharmaceutical firms, the pharmaceutical industry is a business. And there's all kinds of issues that a pharmaceutical rep can tread upon, on how they deal with doctors, and how maybe it lightened, maybe they can help solve certain problems that the doctors have that have nothing to do with that suffering. That treat?
 
Jon Selig [07:31]
So in short, you can find humour in absolutely any type of industry. The question is, how can you isolate that humour from the things that might seem the most obvious, aka human suffering, and illness and things like that, and whether it's the funeral industry, whether it you know, that you can find that humour, that doesn't what we call punch down on, on the actual tragedy that humans are facing and dealing with, there's always ways to isolate the more business aspects of things, the challenges that the prospects are struggling with, from a business perspective, and not the people they're serving? Who, you know, as I've said, just just our suffering, we, you know, we never have on those things that we never should.
 
Nicolina Savelli [08:21]
Yeah, no, I think that's super important for any salesperson to know, to not mock any, any pain points in any situation. Any industry, you know, people are suffering right now. It's COVID. You know, you need to tread on a fine line of making sure that people are taking your your humour as not offensive, but in short, you can find it in any, any industry.
 
Jon Selig [08:45]
Well, just you used a little phrase, which I want to distinguish. So you said pain points. There's pain, real pain that humans feel and experience. And there's this whole notion of pain points, which is a sales term. And any process that's broken, any struggle that a professional is having, that is a pain point, it is non physical, it might cause emotional pain in our day to day life. And so the jokes that I try and help my clients write are around the pain points that their clients are struggling with. So you know, it's not a joke about, again, people suffering from an illness, but it's a pain point that a doctor might have around identifying the best medication for their for their patients. So there's there's a difference between that that pain point, sorting through all the literature that perhaps the doctor gets from, from from pharmaceutical companies, and of course, the actual illness. So I just want to make that. That's really what I'm talking about. It's more about procedural pain. Not procedural, but those actual pain points that a business is struggling with. So, property managers, one of their pain points is, you know, empty units, or, or marketing of those units and, you know, bad tenants, these are all pain points, they don't mock human suffering in any way, shape or form.
 
Nicolina Savelli [10:12]
So I guess, I mean, you touched on this, but we can dive a little bit deeper, what makes something funny or unfunny?
 
Jon Selig [10:29]
There's, there's a few things. The first is always going to be look at comedians thrive on surprise. So good jokes. And when I say jokes, I'm not talking about like, you know, three religious leaders from various faiths walk into an establishment of ill repute, and the bartender, you know, said something offensive to them. Or, like, I'm not talking about these kind of jokes at all. To me, a joke is like two sentences on average, maybe one, maybe three. And it consists of the setup and the punch line. And the setup provides the listener with, with some information, which, you know, with sets expectations in the listeners mind of what's going to come next. And the punch line comes along and subverts those expectations, it goes in a different direction. So the first element of what makes something funny is surprise. And you could build you could write those you can make those surprising statements about any particular premise on the planet. premises the topic of the joke. So surprises number one, but number two is relatability. Your audience will they relate to what you're saying in the setup? Is it important to them? So, you know, famous example I like to use when I speak with sales teams. There's one comedian I do shows with in Montreal, and I mean, I just can't believe how tone deaf they are to who their audiences, they'll come out, literally ask the audience. Hey, who's a fan of pro wrestling? And no one will respond and they'll go, Greg, well, I have like three minutes of pro wrestling jokes. Hey, do you guys like Jurassic Park? And no one applauds because it's like a 27 year old movie at this point. And they have a bunch of jokes about Jurassic Park, I'm thinking, you really don't care what's relevant to your audience, you don't know how to relate to them in any way, shape, or form. And that's why you never make anyone laugh. So surprise, and relatability, I think are like the two at the top. But there's also this idea of incongruency or ridiculousness. So a lot of good jokes compare one thing to something completely out of left field. It's a bit of a surprise, but there's an in congruence drawing these ridiculous parallels, sometimes absurdity.
 
Nicolina Savelli [12:39]
So I think touching on that relatability. If, for example, you're a new leasing agent, you know very little about the clientele of a property or your audience, what are some steps you would recommend they take and getting to know their audience better and being more relatable?
 
Jon Selig [12:53]
Yeah, so I mean, the first thing to understand is like, okay, leasing agents, if I'm, if I'm selling to them, what does their job look like? What are they trying to achieve? What are their struggles? What are their dreams? What are the big roadblocks in their day to day that are preventing them from reaching their dreams? And then at that point, isolating those and figuring out well as a seller, which of those can I? Which roadblocks can I remove, that you've isolated the pain you solve for your buyer, at that point, you know, start to look at words, some of the words and phrases in there. And maybe why that problem is so ridiculous for them, and start expanding upon it. And look, it's a writing exercise, I don't care. You know, it's not the kind of thing I'm going to get people doing right off podcast, but I guess it's the crux of my training workshop. But, you know, if you can take that problem, you solve for your buyers, isolate it and explain why that sucks. In simple English, and then figure out a way to make it a little funnier, and then turn into like a classic joke, you're gonna have that chance to really show your buyer like, again, I understand you, and I love they're gonna they're gonna, it feels like a bit of a Jedi mind trick, when you can make some really nice joke about, you know, getting apartments rented.
 
Nicolina Savelli  [14:08]
For sure. So, are there any absolute no no's when it comes to making a joke in a sales situation? Is there anything you've encountered where you're like, oh, that went completely downhill or that didn't go over as I planned?
 
Jon Selig  [14:21]
Not in my case, but I have heard some horror stories from, you know, like just people not knowing what the line is. And look, empathy is such a big thing in sales, and it's such a big thing in comedy and we have to understand what people are sensitive about, and even Before, this whole, like, you know, comedies changed so much in the last, let's say, five years, where, you know, it's not acceptable to punch down on marginalized groups in society, whether gender, whether it's culture, whether it's sexual orientation, whether it's religion, I mean, obviously, politics is somewhere you, we do not want to tread in 2021. Because you just don't know who your audience is, no matter what rapport you've built with them, if you drop some joke on them, that that highlights any of these, or even, even, you know, we don't want to punch down on people who are like marginalized groups in society. So for example, like, the physically disabled, the mentally disabled, you know, you might, you might make a joke, and, you know, your buyer might have a nephew or niece, that is one of any of these groups I mentioned. And no matter how great your relationship is, it might go south really fast. So these are the areas which I encourage people to, to never, you know, joke about in conversation with prospects or really with complete strangers. And I mean, I think we should also be moving past some of these jokes. I watched some comedians who do accents and ethnic impressions. And I'm like, I mean, I saw this in like, when I was just starting to watch comedy in the early 90s. Like, it feels a little old.
 
Nicolina Savelli [15:59]
Yeah, we need to evolve a little bit.
 
Jon Selig  [16:01]
A little bit. And you can find humor in anything. And I also don't think people should be like, quote, unquote, canceled for certain kinds of jokes. But at the same time, I think comedians should do better. And salespeople, you should stay away from this stuff entirely.
 
Nicolina Savelli  [16:17]
Yeah, absolutely. Good advice. So tell me about a client of yours that you feel really succeeded using humor in the sales process? And why do you think they excelled so well?
 
Jon Selig  [16:28]
Not sure it's a client, I'm going to tell the story about because I work with sales team. And some of them like just look at it as like, you know, skills development, and do they use the jokes, not always certain, say the truth, sometimes I'm, I'm in there, and I'm out. And, but I do get some notes from some sales reps going, what you taught, really helped for a variety of ways I'm, I'm I'm loosening up by being a little funny with my clients. Great part of my part of my workshops. We have an open mic at the end. And everyone is working on writing these jokes that, you know, what we call roast their buyers. And so like, why is this problem we solve for our buyers suck so much for them. And, you know, the story I'm about to tell you is about someone who was actually it was a 90 Minute Webinar, and I was just going through like a very abridged version of my workshop, I'm teaching the steps on how to write a very simple joke. And I get a note a couple of days later from someone who I connected with who was on the webinar. And he says, Hey, check out my post. And he worked for a security he works for a security company, I don't know if he still works there or not. He worked for a an online security company. And he was comparing, I guess hacks to a beluga whale. And he made like an image of the whale and evolve with the punch line evolve the word breach, which I didn't know that this apply to whales. So I find that but but he ensured he was creating all these means associated with the joke structure I taught him to write. Right. And he totally he sent me a message A few months later and said that his jokes, which he learned how to write from the 90 minute workshop with me, yielded him yield to the company, I should say, high five figures low six figures of closed revenue, annual revenue for Wow. And I was like, I fell off my chair because no one had been tracking, right? The results of what I do in any meaningful way. And this guy, like he gave us a free webinar, he just came on, and he was just like, going to town with it all. But the reality was, he he learned it, he, he took what the steps I showed him, he applied it. And then he worked at it. Like he wasn't expecting something to magically happen. He of course, formula which I taught him and he ran with it and he generated a bunch of jokes, which he used in sequences, different touchpoints with his buyers pipeline and lead to close business for the company. So that that's, that's the most you know, real example, I can give someone learning how to use humour in gesturing into their sales efforts and generating results.
 
Nicolina Savelli  [19:10]
Right. So you mentioned a formula. I'm not gonna I mean, I'm not going to make you talk about the formula because we don't have 90 minutes. But could you share some some resources for sales professionals that are looking to do this and and try this out themselves, and inject some some humour in their sales process, process it, whether it be your own resources or a recommendation, otherwise, it's up to you.
 
Jon Selig  [19:35]
I'm gonna I'm gonna answer it in two ways I am watching, I don't know when self guided course, okay, you really map out who your buyer is, and how to craft chambers specifically for them. That acts as the connective tissue between you and your buyer, and then why they should talk to you. And that's what the jokes are meant to be connective tissue, or your relevance. However, I don't know when that's going to be out. I think the first step that anyone needs to do before they attempt to write comedy, or jokes is to go watch comedy. Okay, not just stand up. If we look at sitcoms, particularly from the 70s 80s and 90s a lot of it you know, I used to watch sitcoms you know, I don't know any people who talk like this, like where every 20 seconds there's a laugh happening, right right now to to any of your favorite sitcoms from growing up. Whether you were a kid and watching full house or you're an adult watching cheers are all in the family or the Golden Girls there. Very much set up punch line character a says something, you know, of concern. And another character says something like in a really smart assay way. Yeah. Joke structure is just like classic joke structure number one. And so it's good to watch sitcom stand up comedians, even if they're kind of presenting things in less of a setup, punchline kind of way. They ultimately most of them ultimately, tell jokes. And these you know, that are formulaic by nature. They're comparing one thing to another, or they're misdirecting. So they're doing a lot of that. And I think I think the best thing, if you really want to start learning, how do I get funnier is to go watch comedy of all kinds, whether it's stand up sitcoms animated like the Simpsons, huge Simpsons fan, go watch, go watch a late night talk show host, interview his guests, and especially the comedians and see the back and forth. Sometimes it's the guest who is funny. And sometimes it's the host who is funny together, but just watch, like, try and like observe patterns and timing, and absorb that over time, because that'll seep into your ability to eventually put some humor together.
 
Nicolina Savelli  [21:46]
Great advice. Thanks for that. So if people want to find your resources, where can people contact you, if they're looking for your services, or resources or anything else related to to writing or humour, writing and comedy writing?
 
Jon Selig  [22:04]
Yeah, the two best bots connect with me on LinkedIn, just find me it's Jon. And the the H in Jon is both silent and invisible. That means there are j o n  s e l i g on LinkedIn. And that's my website to JonSelig.com. And if you hit go to JonSeling.com/offerings, you can see the various ways in which I can help sales teams. And common soon, I don't know when exactly will be a self guided course where I'll be having open mic style dropping sessions, where sales reps can can deliver their material, get feedback from myself and other sales Pro, they could boost how they can get a little more creative. Because I think a challenge is the creative. Some people don't have that creative gene. But it can be developed, it can be worked on. And it's all about just having your mind open up by other people sometimes. So that'll be part of what the live sessions are all about.
 
Nicolina Savelli  [22:59]
Right. So I was gonna end there. But I do have a question about that. So there are people that are naturally funny, or at least they've observed comedy there, maybe from infancy? I don't know, maybe their parents were funny. Maybe, you know, is there certain people that maybe should just not do this? Because it doesn't come naturally to them? Or do you think that if they can get a formula down that in the writing, they can still deliver comedy, but maybe not in a telephone call? Or is there certain mediums that they can be better at it if it's just not something that's natural to them?
 
Jon Selig  [23:37]
Yeah, if it's not natural, don't rush it. I'm a firm believer that if you have a sense of humor, if you've ever laughed at a joke, if you've ever repeated a joke that you heard on TV, if you've ever said something spontaneously funny, even once a year that makes people laugh, you have a sense of humor, and you can be trained to deliver one joke repeatedly. I believe that but I do also believe don't force it. And I think the first step to getting funnier is just to express yourself and maybe grab a pet pad and paper or a Word document and just start joking writing down everything that happened around a certain experience, get your thoughts out, get your emotions out, get the other person's emotions out if you were dealing with a with a prospect, what were they? What were they worried about? What was what was stressing them out? What What were they struggling with, and the more we express ourselves. Ultimately, the more we have, the more raw materials we have to sift through, and pick out those little nuggets of funny. So I think everyone should try and work on getting a little funnier if they want to, if they don't want to, then there's no need to, but if they want to expression is really the first step. Just keep watching comedy, and eventually, you'll become I don't want to say natural liars because I don't teach people to become naturally hilarious. I teach people to get even a little bit funnier. And my goal is to help every sales rep have a go to joke or two, that they could drop on their buyers to make them seem funnier and likeable. And it just, it's a process. People always told me I was funny, but I was never that life of the party. That person, you know, standing around the kitchen, in the kitchen at a party with a beer in his hand, just telling stories that like everyone is just cracking up over. I'm sort of more of the observational type and are doing stand up. Even then, you know, we all stink at first it stand up. And I don't know if I mentioned this, but I've been doing stand up nine years. We all stink at it. But there it takes a little bit. You know, if you bomb, you go and watch your recording, which I would fill myself every time I'd be critical of it. I would try and figure out where am I connecting, not connecting with people, I would try and improve what I'm saying, especially if I'm getting some little reaction. If something is like dead silence, I'm not going to work on it too hard. But if if there's 20 people in the crowd, and three of them are kind of chuckling I know there's something funny there now, how do I repackage this and repurpose it and make it relatable and funny to everybody. And that involves being self critical, and practicing and iterating and editing and more practice. So those are all the tips I have. For people who are a little scared to use humor. It's a process. Same way It took me like four years to get consistent laughs on stage, or figure out how to get consistent laughs I should say, it's going to take everyone some time to figure out how to grow into that and use humor as a tool that they can use to really break down their buyers and build rapport and at the same time illuminate those powerful business points.
 
Nicolina Savelli  [26:44]
Well, awesome. Thank you so much, Jon, for joining me today. I had a lot of fun and anyone listening, be sure to follow the hashtag get synced for more tips and tricks from guests like john and john, till next time. Hopefully, we're connected on LinkedIn. So if I have any questions on numerating, I'll be sure to message you and maybe join your your course next time.
 
Jon Selig  [27:04]
Absolutely. I'll be delighted to take your money.
 
Nicolina Savelli  [27:09]
Awesome. And until next time, everyone, keep swimming.