One of the most valuable attributes of a leader is a well-developed sense of humor. Whenever you see leaders be funny, especially at their own expense, they usually end up captivating their audiences. It shows they are human and humble.
Winston Churchill, the great prime minister of England during World War II, was famous for his quips when speaking to Parliament or when faced with a hostile press. He had quite a high self-regard, and yet, toward the end of his life he said, "I am ready to meet my Maker. Whether my Maker is prepared for the ordeal of meeting me is another matter."
A similar Churchillian quote is, "History will be kind to me, for I intend to write it." 
He once described politics as "the ability to foretell what is going to happen tomorrow, next week, next month and next year. And to have the ability afterwards to explain why it didn't happen."
President Ronald Reagan was always quick to poke fun at himself. "There are advantages to being elected president," he once said. "The day after I was elected, I had my high school grades classified Top Secret."
Famous, or infamous, for napping, he once said publicly: "I never drink coffee at lunch. I find it keeps me awake for the afternoon."
I use humor in my speeches. Being of — ahem — a certain age allows me to say things like, "I have been involved in the healthcare industry since the Roosevelt administration (pause for a little chuckling)…and I don't mean Franklin." Get people laughing during a speech, especially when the laugh line is germane to the topic at hand and not just some random one-liner you heard on Letterman, and you have formed a bond with your audience. (Never tell any off-color jokes, of course, unless it is a roast, then all bets are off. The humor must be appropriate to the audience.)
Humor is disarming. Think of how it can defuse palpable tension during a meeting. When something the company has done has gone spectacularly wrong, the CEO might say, "Well, at least we looked good doing it," or, "Hey, three out of 10 makes you a Major Leaguer."
A little laughter makes people breathe more deeply and think more clearly. It also puts things in perspective. Too often we take routine matters and make them into crises. People are often afraid to speak up in meetings, and a little humility and humor from a leader helps break through that barrier.
When you have a meeting with someone, a little banter helps break the ice. It is not that you don’t take seriously what is about to happen, but that you show that you don't take yourself too seriously.
Even having an amiable look on your face as you walk through life is helpful. I notice every day that when I greet people with a smile they invariably smile back and make eye contact. Often they will even say hello. I have struck up conversations, and even friendships, this way.
A smile on your face makes you feel better too. Try it, and you will see. Part of this is having a positive outlook on things, being interested in the world around you.
Perform a random act of kindness for someone such as holding the door for a stranger, and often you get a smile in return, maybe even a thank-you.
So turn what can often be a cold world on its head. Bring some warmth and some of the funny. Smile at people. Success is whatever you want it to be. Make part of it being a decent human being.
Use your own foibles to break the ice. Hey, I know I am perfect, but you…
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