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Leadership10 MIN Read

The Art of Humor at Work

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Tigerhall Team

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The Art of Humour at Work

Made an awkward joke that no one laughed at? Struggling to use humor to your advantage in business meetings? Allow our talented conversationalist and CEO of BookMyShow Indonesia, Sudhir Syal, show you how to use the art of humor at work even if you don’t have a funny bone in your body.


  • Make your business partners laugh while signing your million-dollar deals and achieving your business outcomes
  • Back pedal yourself out of a Trump joke gone wrong and still keep the conversation enjoyable and effective
  • Use humor that leaves others with a good opinion about you during and after the meeting
  • Lighten up dull meetings and make business partners and clients laugh even if you have a humor that can’t seem to make a hyena laugh


You watch your hilarious colleague or boss make the client roar with laughter while you struggle to chime in with a witty remark or even a funny quip. This is the norm for most people. We could be hilarious with our friends or family members but when it comes to business partners or clients, we’ve somehow lost our funny bone.

When people meet someone who can make them laugh and enjoy a good conversation, it’s therapeutic. Life is stressful, and people are carrying a lot of pain with them. There are very little things we can actually control in life, and a lot of things to be depressed about. If you’re able to use humor in business meetings, you could change the trajectory of your meetings.

If you manage to make your counterparts laugh on a regular basis, then you've hit the jackpot because people would just want to be around you. You become the person with good vibes and an energy that draws others and makes them feel good. You’re sort of like Santa Claus who brings a sack full of laughter.

This would be great, of course, but can we all be funny? I get that some people are funnier than others, but I don’t believe that anyone is just born funny. Humour is an art that can be developed. Some people develop it more easily or naturally than others but it’s still something that can be developed practically.

I’ll give you a backbone for making your conversations more humorous in the next chapter. For now, I want to highlight what not to do when you’re building relationships through humor. Get rid of old habits and mindsets so that you can start building new ones that leave trails of laughter while signing your deals and achieving your business outcomes.


People are often afraid of taking risks in conversations or they try to keep it safe, and that’s why they never become funny. You don’t have to always stay in the sensitive zone. You can joke about their country and yours too. Start by cracking jokes on your own nationality, and then you can sort of take a jab at theirs too.

Of course, please take risks within reason. Keep it positive, don’t crack a joke at the cost of someone else. Don’t crack jokes on family, kids, religion, looks, size, appearance or specific political views that are uncommon. Stay away from that at an early stage. You can make a tongue-in-cheek remark though. For instance, if you know that the person you’re talking to is a Trump supporter and he or she is working on a festival that has sort of dipped, then you can joke “Let’s Make it Great Again”. You can even perhaps crack a joke on their accent or pronunciation if you think they would receive it well. You need to observe how they respond and adjust accordingly.


Crack jokes and then bounce back to serious conversations. You can fall back on the joke again later if there’s an opportunity but don’t drag out the joke for too long. Be on task about building good conversations and allow the jokes to slip in when there are good opportunities.


When you enter a conversation, let the other person talk first, and then you come in. Based on what they share, you can in some way, start throwing darts to see what sticks. Follow the ones that stick and double down on them. If you’re unable to break into anything based on what they shared, then get into a short 2-minute monologue about one of your own funny experiences. They’ll appreciate your efforts in trying to make conversation and keeping it light-hearted. Just be sure to give them the opportunity to speak first before you break into your monologue.


I read about a study where they concluded that a man has only two needs. One of them is the need to feel important, and the other is sex. Let’s keep focus on the first need and I'll leave another expert to explain the second.


Make others feel important when you joke with them. Everybody likes their ego being played up. Make a joke that makes others look and feel good. Make the person feel important. At one of my recent meetings, someone was wearing a rock t-shirt, and we started talking about Bohemian Rhapsody and had a good laugh about it. You need a keen eye to praise the person. Even if the person knows that you’re just praising them, it’s okay because it builds chemistry. You need to show them that you understand their world or are at least willing to do so.

For instance, people from the Philippines are proud of Jollibee, and it's a good potential joke that boosts their ego where you can ask them if they wait in line for 10 hours for their Jollibee meal like the Canadians did when it opened in Canada. It shows that you understand their country and are making them feel good about where they come from.

Of course, in the case where you are talking to the daughter of a billion-dollar media company, you can’t joke about how she owns the media company, because she actually does! That’s not a joke, that's just stating of facts. Humour can then come in where you talk about similar experiences. For instance, I know she went to Coachella, and so I share a funny story of a similar event I went to. So again, be sure to build their ego without just stating the obvious facts.


It’s important to do some research and learn more about the person you are about to meet. I did research on the daughter of the billion-dollar media company and so I knew that she enjoyed Coachella. During my research I found out that a lady I was going to meet had a cat, so we went into the meeting and after asking her about her cat, we ended up watching videos of cats for about an hour. Later on, when we saw the cat as her phone wallpaper as the meeting was ending, we could also refer back to it as we joked with her. You can be open and honest about having done the research on them, it’s often flattering to them because it shows that this meeting means a lot to you. Make an effort and take a risk while still being positive - you would not want to speak ill of cats in that meeting.


Something that is really powerful is having a common enemy with the person you’re speaking with and then taking the jokes from there. For instance, it could be an event, an item or even Trump. Once, I met a Grammy Award winning music producer and cracked some jokes about someone I knew he didn’t like. He also took humor in making fun of that common enemy and so we hit it off from the start. While it’s true you may not know how the person would take it, I would say take a little risk.

What happens if it goes wrong?

“If a joke goes badly, you pivot.”

You take a few steps back, but don’t stop. Read their face, and you can tell how it’s going. Don’t back off and don’t apologize. You pivot by confusing them and having a middle ground footing. For example, if you made a comment about Trump and the person supports Trump, you can pivot to agree that Trump has come through in certain areas and then move on to the next topic.

Have a few jabs to read the signs. If it’s good, then you dive in, if it’s bad then you pivot. Adapt to your audience because not everything will work with everyone. You need to know what jokes to crack so that the other person will understand and appreciate them. Part of this comes from reading their body language, and the other part of it comes from your research. You can even research what parties they are aligned to if joking about Trump is your go-to.

Develop a keen sense of observation and be sure to focus your attention on them. Pick up on body signals and read books about non-verbal cues to help you understand people better. Some people are tougher to read and break, like the Swedes, so it may take a while to get them to laugh. They tend to be expressionless most times while some other cultures, like Americans, may be easier to read and attuned to laughing from the start. So, don’t give up and try to read the other person as much as you can.


Find a common subtext that you know the other person has some knowledge of. A common subtext doesn’t need to be about politics, though it is an area most people are able to refer to. Keep in mind that the goal is not to have a political debate, the goal is to build a relationship. So, you can crack a joke about Brexit or Trump but just be sure to have a pivot ready and focus on the relationship building – not the facts of the political matter.

Other common subtexts could be things like the latest Korean movie. If you have nothing to talk to a Korean about, you could at least bring up a Korean film and move on from there. Being curious and well-read can really help you in your humor. So start exposing yourself to a broad range of movies, TV shows, books and other cultural avenues so that you have something to joke about. Watch, read and listen to a wide mix of content from different cultures and genres. That will set you up well for cracking jokes with a wide mix of people.


Being attentive and thoughtful helps you to be funnier and also builds good rapport. When you remember what the other person has told you earlier, and play it back to them as a joke, they really appreciate that you have been listening and they will leave the conversation feeling like their words are valuable.

Being attentive and thoughtful doesn’t mean you never interrupt. People usually say not to interrupt other people when they are speaking, but honestly, sometimes you can interject and have good rhythm in the conversation. Don’t be rude about it, and again, be sure to read their expressions as you insert jokes in the discussion.

Pay attention to what people are wearing and play it up. If they have an extravagant batik shirt, then talk about it since the probability of them wanting to talk about it is rather high. Look for talking points that people are showing. People want to talk about what they feel like talking about, and they will often show you what they enjoy talking about, sometimes through their clothes and accessories, so pick up on those cues.


Your humor and jokes need to come across as effortless. You need to put a lot of effort into it and then make it look effortless. Like a duck that is serene on the surface but frantically paddling underneath. Trying too hard doesn’t come off too well, so you need to practice beforehand. Another way to come across effortless is to show confidence and status while being likable. If you walk into the building like you own the building, people will think you do. Project a status of confidence, and it helps your humor to seem more effortless. Fake it till you make it.


1. Be in the Know

Have more topics of conversation by being curious and exposing yourself to more avenues of information. Whether it’s watching more movies, reading more books, reading the news or any other simple habit to expose yourself to more information regularly.

2. Prepare 3 Go-To Stories

Prepare three funny stories about a country, industry or experiences that can be quickly brought up. I usually have 3-4 stories about Jakarta and entertainment as my go-to stories.

3. Talk to a Stranger on the Street

You need to loosen your inhibitions by talking to random people on the street. Practice all that I’ve taught you and don’t be afraid of taking risks.

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