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Be a fun-loving leader

Great leaders are ambassadors of happy. Learn from the examples of a president, airline CEO and more.

5 min read



President Teddy Roosevelt in 1912 (Topical Press Agency/Getty Images)

Lead Change is a leadership media destination with a unique editorial focus on driving change within organizations, teams, and individuals. Lead Change, a division of Weaving Influence, publishes twice monthly with SmartBrief. Today’s post is by Chip Bell.

“Would you buy from you?” is one of my favorite questions. It reframes the perspective to focus on how prospects view you. I offer a similar question to all leaders: “Is it fun being led by you?”

Fun is the WD-40-like lubricant that makes cultures innovative and productive. It yields winning work environments in which leaders are gifted at letting go, turning on and ramping up.

As New York City police commissioner, Teddy Roosevelt walked the streets late at night talking with all citizens. According to biographer Doris Kearns Goodwin, this man of great wealth and privilege learned to connect with ordinary people and demonstrate empathy and authenticity. Dropping the arrogance and pugilistic style he had perfected as a boxer at Harvard, he was courageous enough to show compassion.

A New York police captain at Roosevelt’s funeral said, “It was not only that he was a great man, but, oh, there was such fun in being led by him.”

Roosevelt’s biographies state he hunted wild animals in Africa and, as a naturalist, started the U.S. Forestry Service. The Noble Peace Prize-winning president occasionally skinny-dipped in the Potomac River after a winter nature walk. Roosevelt was posthumously awarded the Medal of Honor for his heroism at the Battle of San Juan Hill. Elected at 42, he was our country’s youngest president.

Not only did he live while alive, he was a carrier of joy. He hosted Booker T. Washington at a White House dinner, appointed a Jewish person as a Cabinet member, traveled outside the US while in office and flew in an airplane.

Fun leaders are real

Herb Kelleher was the CEO who helped start Southwest Airlines. When I met Herb, we were together working the booth at the 1997 BookExpo in Chicago. Kevin and Jackie Freiberg’s best-selling book, “Nuts! Southwest Airlines’ Crazy Recipe for Business and Personal Success,” had just been released. The Freibergs asked me to help with book promotion, so Herb and I spent time together. I knew his reputation for being a bit of a wild man. I had also heard stories of his innovative approach to building a culture of employees who loved Southwest; a sentiment that also engulfed their customers.

What I learned in the booth was that Herb was completely authentic! His excitement came from a genuinely ecstatic space, not a feature he donned like a mask to influence an outcome. He truly loved his role, his company, his associates and his customers, and it bubbled over in his dealings. His fun-filled manner communicated all things were possible and all ideas were welcome. You wanted to be in the aura of his captivating joyfulness.

So, what is the punch line for leaders? Focus on sharing control instead of taking control. Foster an environment of inclusion by letting everyone in on the running of the enterprise. People will care if they share.

Praise initiative and excellence, not just their results. Practice realness instead of “roleness” — always be authentic. Never allow any actions or attitudes that can risk eroding the self-esteem of others. Be your associates’ biggest champion. Always tell the absolute truth. Let your associates be who they are — the more diverse your work group, the better.

Fun leaders are light

I was about to teach a Six Sigma class for Lockheed Martin near Palmdale, Calif. The audience included senior leaders from the company’s Skunk Works division — the R&D innovators who focused on air defense 25 to 30 years in the future. I was a part of consulting team bringing Six Sigma and lean thinking to Lockheed Martin. The program would be a key part of the company’s success in winning the $200 billion defense contract to build the F-35 aircraft.

A noticeably happy man walked in as students were taking their seats. He was obviously someone important to this class. My co-instructor, a retired brigadier general, asked the man if he would like to speak. He smiled, nodded “no,” and took a seat at one of the small group tables. When I spoke with Mr. Big at the break, he was humble, attentive, and extremely optimistic! I later learned he was executive vice president in charge of the entire aeronautical division and highly regarded by the thousands under his leadership.

So, what is the punchline for leaders? Be an advocate for the “light” — opportunities, not problems. Take the mission seriously, not yourself. Be quick to spotlight the works of others, not your works. Demonstrate a strong allegiance to fair-dealings and wholesome relationships. Anchor your directions to unit purpose and organizational mission.

Tell stories that communicate your vision. Be your associates’ widest net to catch them when their smart risk-taking backfires. Be the partner you want them to be to your customers and other colleagues.

Great leaders are ambassadors of happy. They look for ways to shake up the place with quirky events, silly signs, and celebrative occasions. They constantly seek moments to convey encouragement for ingenuity. And, even with serious work they make certain no one is excused from a delicious belly laugh.

In the words of the character Michael Scott on the TV program “The Office,” “Sometimes you have to take a break from being the kind of boss that’s always trying to teach people things. Sometimes you just have to be the boss of dancing!”


Chip R. Bell is a renowned keynote speaker and the author of several best-selling books. His newest book is the award-winning, best-selling book “Kaleidoscope: Delivering Innovative Service That Sparkles.” He can be reached at

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