Career Testing
Career Testing
Career Testing
WORKPLACE / AUG. 22, 2015
version 30, draft 30

Top 6 CEOs With a Sense of Humor

When it comes to leading a large organization, the CEO’s ability to connect with people and make them like him is essential. Leaders who strike the right balance between laughing at themselves but not at their colleagues or underlings are more likable, trustworthy, and caring.

See Also: How to Win the Trust of Employees

Using a sense of humor at work to connect with people, solve conflicts, and create a positive corporate culture is a good way of engaging with the workers at the company. Some CEOs have mastered their sense of humor, and have become popular within and outside of their organization. The list below exhibits six CEOs who’ve become well-known and occasionally well-loved for their sense of humour. 

1. Virgin, Richard Branson

Richard Branson is a CEO famous for his ability to have fun anytime and anywhere, Recently, he acted as a flight attendant on a Virgin flight from Perth to Kuala Lumpur. Dressed in a red uniform, with matching red heels, the CEO served drinks for passengers, while entertaining the crew. Looking a little bit like the Eurovision 2014 winner, Conchita, with his moustache, long hair, and crimson lipstick, he shook hands with passengers, and even spoon-fed one.

His business plan is simple: "work hard and play hard", and it seems to be working out just fine for him. Naming his recent book: "Losing my virginity" was certainly a good choice, and a great marketing strategy. He considers humor an essential quality when hiring new employees, so if you’d like to work for him practice on your humor skills.  He handles his Twitter account personally, and regularly sends out updates about his philosophy of business. In August, 2015, he said: "No matter how old you are, spend as much time as possible exploring, playing, and learning". Amen.

2. Microsoft, Steve Ballmer

According to most people, Mr Microsoft was born to be on stage. Every presentation he holds about new software releases attracts huge media attention. Back in 1986, long before he was the number one person in the company, Ballmer was entrusted with his first on screen Microsoft commercial and he made sure that it was a thrill; he entered the stage with a little dance that was to be remembered for years to come. In the commercial Ballmer plays a car salesman who is pushy and over-exaggerating making people around the world laugh.  His video with Bill Gates dancing to the famous song "What is Love" in a Miami Vice suits is still a social media phenomenon.

But Ballmer’s humor goes beyond the stage as well. In a presentation he once did at the Trevecca Nazarene University someone gave him his Mac Book and asked him to sign it. Without batting an eyelid Ballmer went ahead and signed. He even asked the student if he needed a new laptop; undoubtedly, working for him will mean that there will never be a dull day in your office.

3. Twitter, Dick Costolo

According to CNBC, the leadership of Twitter hired Dick Costolo because he had a great sense of humor and good leadership skills. A former comedian, the CEO was simply able to communicate with employees in an easy to understand manner. In a 2013 speech, he told the audience: "When I was your age, we didn’t have the Internet in our pants. We didn’t even have the Internet not in our pants. That’s how bad it was. I sound like my grandfather". He achieved a 96 percent approval rating, which is extremely impressive. When he left the company in 2015, all employees were in shock, he tweeted in response: "I’m finally trending on Twitter". He continues to entertain Twitter employees through his account on a daily basis, doing what he does the best: connecting with followers on a personal level. He recently tweeted: "Headed to see the #CrossFitGames for the first time this weekend. If you’re watching on TV, I’ll be the guy with my shirt on."

4. Lego, Jørgen Vig Knudstorp

This guy rescued Lego from financial ruins, and there’s no one happier than him for doing that as he is not shy of playing with the company’s new products.  Recently, a video of him was circulated that showed him trying out a new Lego wheelchair, designed by children in the factory. In an investor meeting, announcing a record-breaking financial result, he even started singing "Everything is Awesome" while trying to dance to the song at the same time. Not sure if the investors were more impressed with the figures or his singing voice. Knudstorp doesn’t take himself too seriously and that’s a great quality for a CEO to have. When trying to sell the joy of building to customers in an age of tablets, smartphones, and games consoles, one must do everything to make the brand look more interesting. And Knudstorp knows that very well; that’s why he is more than happy to sit down with children, talk about future products, and even build new creations with them. 

5. Berkshire Hathaway, Warren Buffett

Being one of the most successful businessmen of our times, the entrepreneur and CEO of the Berkshire Hathaway international organization is not only generous, but funny at the same time. He once told reporters reflecting on the investment world: "Wall Street is the only place that people ride to in a Rolls-Royce to get advice from those who take the subway." In May 2015, he made the shareholder meeting of the Berkshire Hathaway even more fun by creating a video of Mayweather and himself fighting in the ring. He appeared as the "Berkshire Bomber" on stage, introducing his training regime, and special diet. He can laugh at himself, but he is most famous of his witty quotes, such as: "you only find out who is swimming naked when the tide goes out". 

6. John Legere- T-Mobile

The leader of the international mobile company certainly has a sense of humor.  He is a laid back guy, who swears on screen and acts like a comedian, while he is also quick on his feet when it comes to destroying competition.  He even turned up at an AT&T meeting, just to get kicked out. After the incident, he tweeted an image of the poster saying: "What happens in Vegas will be on the internet in seconds". He commented: "especially when you’re kicking out the competition from your party right, @ATT?" When Donald Trump, candidate for presidency 2016, announced his plans to build a wall on the Mexican border, he told Fox Business News that his company made calls to Mexico charged at a local rate. He certainly enjoyed the prank, laughing and smiling all the way. He also took on a new habit, calling his competitors, AT&T and Verizon "Dumb and Dumber". 

See Also: 10 Powerful Quotes on Leadership and Success from Powerful Women Today

Humor in the office can be used to improve communication, break down cultural barriers, and overcome difficult situations. The above motivational leaders achieved a high approval rating from their employees, while transforming struggling companies into leaders in the industry. Humor is also great for building up teams, overcoming cultural differences, and improving work morale. Humor motivates people, and engages followers like no other leadership tool. It makes connecting with ideas easier. Used right, a bit of humor can improve job performance of all employees, and help clarify company visions. The use of jokes and the ability to laugh at one’s self makes a CEO more likeable.

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