Be Funny! — The Amazing Benefits of Humor in Your Sales Work.

8 min readDec 20, 2021

Becoming a Better Sales Rep — Post #28

Introduction.

Who doesn’t like a good joke? But, on the other hand, you need to be professional, right? Well, that’s a good question that everyone needs to answer for themselves. If you’re selling life-saving medicine an inappropriate joke might not land that well. However, if you’re selling software licenses to tech startups, you might.

I know I’m thinking in boxes here. My point is just that humor can have tremendous benefits that I want to explore with you. I don’t say you should always use it.

But, I was sitting in the kitchen with my roommate this morning and we were watching a video from the YouTube channel Epic Rap Battles of History. It’s amazing. Check it out if you haven’t. And even if you have, check it out again.

This YouTube channel explains current and past important events and figures in great detail through whity rap battles. May it be Donald Trump vs Joe Biden, Steven Spielberg vs Alfred Hitchcock, or Eastern Philosophers vs Western Philosophers, or many others.

The point is that I personally have no intrinsic drive to learn a lot about history. I know I should learn about history. I know it’s a flaw but it’s a fact. And, these videos stuck with me. The information they portrayed is forever in my brain simply because the content was funny and witty. Ivan the Terrible introducing himself as The Creme de la Kremlin just sticks with me. And all of a sudden, I like something that I wasn’t interested in before.

Do you see the potential benefit for your sales work? Your leads might also not have an intrinsic interest in your product from the get-go. But, after a little fun laughing with you, they will associate so many more positive things with the conversation with you and ultimately with your products or services.

So, let’s take a look at why humor can be helpful and how to include it in your sales work.

Do’s and Don’t Around Humor

Humor works amazingly well and we’ll explore the reasons why in a bit.

But, before we go into this, let me note one very important thing: it needs to be innocent humor. You should never ever go into any offensive or controversial topics. Don’t make fun of your lead or anything that is or might be important to them.

Things that are usually safe are:

Making fun of yourself,
Word plays or puns,
Slight sarcasm, and/or
Unexpectedness/counter-intuitive-ness

Never ever make jokes about:

Race,
Gender,
Politics,
Your lead, and/or
Your lead’s company
A real person that is not in the room
A real person that is in the room

Why Humor Works So Well

So, but let’s get back on a positive note. I make jokes all the time and they’re super powerful to bring sales conversations to the next level. People love laughing. So, let’s first understand why that is, and let’s then dive into how you can become funnier yourself; if you wish to.

Humor Makes Your Leads Listen: You know how hard it is to get your leads attention. The thing that’s harder is to keep that attention. Well, humor can help you with that. A joke or a shared laugh immediately draws attention to the conversation. It’s audible, it’s different, and it’s joyful. All the things that grab people’s attention.
Humor Improves Memory Retention: Just think of it: what do you remember better? A boring meeting with the entire team where you discuss stuff in a professional and dry way or the joke your colleague cracked during lunch break? What are you gonna tell your partner, friends, or family about at the dinner table?
Humor Makes You More Persuasive: This one might not be intuitive at first. But humor is amazing to convince others for one simple reason: humor makes people more agreeable as they’re in a positive space of mind. They don’t immediately make up counterarguments against what you’re saying because they’re enjoying the moment and agreeing with your joke. People rarely agree and disagree at the same time as it creates dissonance in the brain.
Humor Boosts Learning: As mentioned in the introduction to the post, The Epic Rap Battles of History helped me to remember historical facts that I otherwise deemed boring. Your lead might feel the same about all the information you’re throwing at them about your product or service. So, adding a laugh here and there or presenting your offering in a professional but enjoyable way will help them remember it. And, on top, they’ll remember the great feeling they had with you.
Humor Makes You More Likeable: Who are your favorite friends or colleagues? The ones that always keep a straight face or the ones that make you laugh and know how to bring up the mood? Believe it or not. Your leads also have salespeople they like and some they don’t like at all. Adding a little bit of humor will certainly move you to the likable side.

So with this knowledge, let’s get into it and learn ways how you can be funnier!

Strategies to Become Funnier

Many people think that being funny or not is completely innate. And, it’s true that there are naturally more or less funny people. But, it’s not all innate. You can learn to be funny. Let’s see how:

Watch Funny TV Shows or Movies and Learn: Humor evolves with time, so make sure to watch contemporary movies, but by simply viewing your next movie nights as an assignment. Take notes on when and why you laughed.
Pay Close Attention to When People Laugh at Work: Well, you can most likely think of a funny colleague. Pay close attention to what they do and how they make people laugh.
Take It Step-by-Step: You don’t need to be Mr. Bean tomorrow. View it as a growth project. Learn and try small things and evolve your humor over time.
Test Your Jokes with Your Friends or Mentor & Get Feedback: Not sure if you’re funny? Well, get feedback. Test your jokes or approaches in a safe environment before you deploy your new funny self with a lead. Make mistakes, laugh at them, learn from them.
Stay Committed: Humor is a muscle. The most important thing is to continue growing it. I make a ton of stupid comments every day and I don’t know where they come from. But I know that they’ve gotten funnier the more I practiced them.
Surround Yourself With Funny People: My roommates and I throw stupid jokes back and forth every day all the time. And you can’t imagine how often someone is completely disappointed by an awfully bad joke one of us makes. But sometimes, things that are too bad to be funny are even funnier than a good joke. The point is, we all learn and laugh together. And we really enjoy the process. And this makes it so much easier to stay on track.
Create a Toolkit of a Few Safe Jokes: It’s always good to start and build confidence by having a little tool kit of one, two, or three jokes or comments that work every time. You meet new leads every day. So you can deploy the same joke and humor because nobody will know that you used the same comment in your last meeting.

Concrete Tactics to Help You Be Funnier

Okay, but what can you maybe try out immediately. Well, let’s take a look at three things that are safe and usually work quite well.

Utilizing Unexpectedness: This works best if you explain a scenario that involves a problem that in itself asks -even screams — for an obvious solution but you give an unexpected solution. You can also turn this around by offering a resolution first and then revealing how it was reached in an unexpected way, tho. An example might be: “I have an Epi-Pen. My friend gave it to me as he was dying. It seemed very important to him that I have it.” The obvious misinterpretation of the protagonist adds a level of humor.
In a sales call you can transform this into saying something like: “We did a lot of research and our clients were asking for X.” Then you jump to a slide that shows something funnily useless before you reveal your real solution.
Saying the Opposite: Imagine the case that you have terrible tech issues in your demo, saying something like: “What a wonderful way to start a demo” might work wonders. It shows that you acknowledge the moment. It shows that you can laugh at yourself. And it releases so much momentary tension. It works even better when you laugh yourself.
However, keep in mind: this tactic is close to sarcasm. Try to stay away from being perceived as sarcastic — unless your British; then people expect it. You can easily avoid it by not making too many jokes that have the exact opposite meaning.
Slight Self-Deprecation: I’m currently coaching a few students at Harvard in their negotiation skills. In our last meeting, I ask them to fill in the feedback survey. Rather than just stating the fact, I usually say something around: “It would be really valuable for my boss to know if she should fire me.” People always laugh, 100%.

So, with this knowledge, go and try to make your leads laugh and make the world slightly happier. (:

Resonaid Is Getting a Joke Feature Early Next Year

Resonaid is a tool that helps sales professionals with writing personalized messages for their sales outreach. And, we’re currently working on a joke feature. Honestly! : D

We recently released the first version of our product as a Chrome extension in the Chrome Web Store.

As we just went live this summer, you can currently test Resonaid for free and get large discounts by being an early user.

About the Author

Teddy Lange is a co-founder at Resonaid and is responsible for business development and customer experience. Before joining Resonaid, he’s been a Sales Rep and Junior Sales Manager, and co-founded various companies. He’s currently finishing his graduate degree in Public Policy with a focus on communication at Harvard University. Feel free to reach out to him at teddy@resonaid.co.