Team building, motivation, workplace culture, and telling uncomfortable truths are the benefits of well-crafted workplace comedy. The manager who understands it builds resilient teams with confidence in their leader. The manager who doesn’t will be resented as a scold and — worse — leave teams brittle and unable to endure challenges. Workplace comedy invariably offends someone. A wise manager must balance the risk of offense against the necessity of comedy in the workplace.

Every Court Needs a Jester

The term “jester” is derived from the Anglo-Norman (Old French) words gestour or jestour, meaning storyteller or minstrel. Over time, the role of this entertainer became far more vital than mere entertainment: The jester could tell the truth that could not otherwise be told. Who could tell the king he had lost a battle? Who could declare taxes were too high or confidence in military leadership too low? This guy — unless an unwise king ordered his hapless jester beheaded.
To the wise business manager, comedy in the workplace serves the very same function — with the same caveat.

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A Jester Beheaded

When I was a new Lieutenant, I had a soldier in my platoon I’ll call “Steve.” Steve was an experienced troublemaker with a natural charismatic aura. The other soldiers respected and looked up to him, and he in turn asserted himself socially as their representative. The secret of his success was perfectly timed and executed comedy.

Gaining Insight

Steve had the rare ability to point out the elephant in the room, the thing no one else wanted to acknowledge or address. With surgical precision, he would crack a joke that would draw attention to the forbidden and make his teammates laugh it off.
What turned this comedian into a leader was how he shaped and targeted his humor to hit everyone equally but fairly. His jokes were pointed but never mean, his demeanor was always friendly, he didn’t hold back because of rank, and his jokes always contained an element of truth. As a result, his leaders found him as valuable as his teammates, and no one felt unfairly treated. To a wise manager, he was a walking informal complaints department who provided an unofficial way to deal with problems before they became official.

Losing Perspective

To my regret, however, during a period of weakness brought on by too little sleep and too much responsibility, I lashed out at Steve when he was doing no worse than just being Steve. The result of this lapse in judgment was a break in rapport, who abruptly retreated into his metaphorical shell. I had beheaded the jester.
Suddenly, I was blinded to the needs and feelings of my men. The section commanders did an adequate job of allaying the soldiers’ concerns, but even the best section commander is somewhat detached due to rank and hierarchy. Comedy in the workplace was my back channel, and now it was gone.
Luckily, after some time had passed, Steve regained his confidence, thus restoring the team dynamic of my platoon. Once again, he became a reliable source of information. And I learned a permanent lesson at a — thankfully — temporary cost.

Gaining Perspective

In essence, the Jester is and has always been the last line of defense in the battle for common sense. They have forever been the pressure tester of ideas and the illuminator of idiocy, hypocrisies, and inconsistencies. They identify social patterns and have the courage to communicate their observations. By their very nature, they are incredibly intelligent and observant.

Political Correctness Also Kills

During my time in the infantry, I noticed it was invariably the class clowns who bonded teams. Their jokes knew few limits, and no one was exempt. An officer who could take a joke on the chin and walk it off demonstrated his strength of character and earned the respect of his team, who rightly expected he would demonstrate equal resilience in other, more challenging situations.
Conversely, how can you trust an officer with the lives of his men if he can’t even handle a joke? The teams with the best-developed comedy in the workplace were the ones who survived the greatest hardships, plain and simple. The leaders who were unable to value comedy in the workplace destroyed morale and fractured teams.

Private Sector Fun Police

When I transitioned from military officer to business management, widespread censorship hit me with the subtlety of a freight train. Even my top-secret work had never been this censorious. It was as if an unseen presence imposed an unspoken taboo that to give offense was the gravest of crimes, forbidden under any circumstances. Even a hint of workplace comedy earned the would-be jester an interrogation by the Fun Police — uptight managers who kept the workplace on edge and the workers wound tight.

Is Offense Subjective?

What is okay for one person might be highly offensive to someone else. As such, it is impossible to uphold a policy of “never offend anyone, and yet many workplaces accept that as the preferred mode of operation. Have they never learned that comedy in the workplace is the key to getting through tough times? Have they never experienced “tough times”? Perhaps Gabrielle Union was right:
“Drama can feel like therapy whereas comedy feels like there’s been a pressure and a weight lifted off of you.”
I’d seen brittleness turn to failure before, and I knew what it took to endure hardship: a sense of humor — some comedy in the workplace.

Conformity By Exhaustion

Nevertheless, the censorship was there, always pressing down. The best practices I’d learned in the field prompted “correction” so often that I, too, began to conform. Slowly, the humor drained from the workplace, and with it the insight it brought. Looking back, I see how avoiding humor translated into avoiding problems by not addressing them.
I finally realized how I’d let myself down when, at a leadership conference, I answered the question, “What do you think is the most important function of a leader?” Drawing from my own experience as a leader, I said, “Good leaders are those who can articulate and contextualize the truth.” At that moment, I realized I wasn’t living up to my own leadership standards.
Political correctness also kills. No leadership, no jester. No jester, no truth.

Offense Taken, Not Given

Though modernity may have killed the fearless jester, comedy in the workplace need not follow. Applying balance to what is acceptable (while taking subjectivity into account) is how good managers must confront the challenge. To address this balance, I’ve developed three principles:
  1. Bullying vs Banter. Banter is good-natured. Bullying intends to harm. The difference is in the intent. A wise manager divines the intent before addressing a conflict.
  2. Problem vs Person. A good jester can delineate between the problem and the person responsible, and target their joke appropriately. Subtle changes in language can mean the difference between constructive criticism and personal attack. The most proficient jester can talk about the elephant in the room and leave out the person behind the pachyderm.
  3. “Time and Place” vs. “In Your Face.” There’s a time for jokes and banter, and there’s a time for seriousness and decorum. A good jester needs to read the room, and a good manager needs to provide guidance on how to do that.
Ultimately, to fear the jester is to fear the truth. To kill the jester is to sail in willful blindness toward whatever peril might be lurking before you. Are people going to take offense? Of course. Will you allow them to destroy morale and turn your teams into fearful, wounded wrecks? Not if you want to weather the storms that inevitably lie ahead.

Comedy in the Workplace and Learning Leadership

To conclude, be mindful when silencing your jesters, particularly if they might be telling you something you need to hear. If you have a jester in your team or organization, be grateful — and careful. Too much offense might ultimately expose you to legal liability, sure. But if you behead the jester who provides truth and common sense, you may not see key issues in your team until it’s too late. Wise managers must nurture healthy, resilient, and capable teams. There’s no better way to do that than by introducing a little comedy in the workplace.

Workplace comedy is serious business — and we’re brave enough to say it. The Eighth Mile offers an 8-week leadership course where we share all the important lessons (and some hard truths) we’ve learned from our experiences as leaders. View the course page to see if this program might be a good fit for your career journey.

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David Neal Is a leader, strategist, founder, project and change manager, as well as a practical consultant for clients such as the ADA NSW, University of Sydney, Australian Defence Force, Prescare, RSL Queensland, MedReleaf, and KPMG. ​He is one of the authors of ‘Growing Good Leaders’ which focuses on developing high performing teams and running projects. He travels throughout Australia and overseas helping others to simplify the complex. His time serving in the military has provided him with vast experience in leadership, complex problem solving, project and risk management. He has chosen mateship, family and helping good people as his path.

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  1. […] conflicts and tension constructively, even with humor if lightening the mood is what’s […]

  2. […] conflicts and tension constructively, even with humor if lightening the mood is what’s […]

  3. […] – How the Subjectivity of Experience Affects […]

  4. […] As the leader, however, you cannot fall into that trap. As discussed above, getting to the truth of a situation is not simply accepting what is presented to you. You must find a way to communicate with everyone, ideally by creating opportunities for their opinion to be heard.  […]

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