Humour does more than make work enjoyable. Used well, it builds relationships, releases pressure, tests ideas and gives teams a way to say things that might otherwise remain unsaid. For leaders, that last function might be the most important.

The challenge is that humour also carries risk. It can strengthen relationships or undermine them. It can expose an uncomfortable truth or simply make someone the target of a joke. It can be evidence of trust within a team, or evidence that someone doesn't feel particularly safe within it.

The answer isn't to remove humour. It's to develop enough judgement to know the difference.

Every Court Needs a Jester

The term "jester" is derived from the Anglo-Norman words gestour or jestour, meaning storyteller or minstrel. Over time, the role became more significant than entertainment. The jester occupied a peculiar position within the court: they could sometimes say things to the king that others could not.

Who tells the king the battle has been lost? Who points out that confidence in leadership is declining? Who exposes the absurdity of a decision everyone else is politely pretending makes sense? The jester. Provided, of course, the king was wise enough not to have them beheaded.

Modern organisations have their jesters too. They are often the people who use humour to expose inconsistencies, challenge assumptions and say what everyone else in the room is already thinking. Wise leaders pay attention to them.

The Time I Beheaded the Jester

When I was a new Lieutenant, I had a soldier in my platoon I'll call "Steve." Steve was an experienced troublemaker with a naturally charismatic personality. The other soldiers respected him, and he had informally established himself as something of a representative for the group. His secret weapon was perfectly timed comedy.

Steve had a rare ability to identify the elephant in the room. With surgical precision, he could make a joke that drew attention to something nobody else wanted to acknowledge. Importantly, his humour wasn't reserved for easy targets. Rank didn't exempt anyone. His jokes were pointed but rarely malicious, and almost always contained an element of truth. That made Steve useful to me.

Without necessarily realising it, I had access to a walking, unofficial complaints department. His humour gave me insight into frustrations, concerns and inconsistencies that might never have reached me through formal reporting lines. Then I made the mistake of shutting him down.

Losing the Back Channel

During a period of too little sleep and too much responsibility, I lashed out at Steve for doing little more than being Steve. He retreated. The jokes stopped.

At first, that might have looked like a leadership victory. The Lieutenant had restored some discipline. What I'd actually done was remove one of my most useful sources of information. I had beheaded the jester.

My section commanders continued to provide insight into the soldiers, but hierarchy inevitably changes communication. People don't always tell their boss what they tell their peers. And they certainly don't always tell their boss's boss. Steve had been giving me access to something different.

Fortunately, over time the relationship recovered and so did his confidence. The humour returned, along with the insight it provided. The lesson stayed with me.

Humour Can Tell Us What Formal Channels Don't

The jester has always been something of a pressure tester. They identify inconsistencies. They expose hypocrisy. They point towards the absurd. And sometimes they can articulate a problem long before anybody has found a sufficiently professional way of putting it into a PowerPoint presentation.

That doesn't mean every joke contains profound organisational insight. Sometimes a joke is just a joke. But when the same themes keep appearing in a team's humour, leaders should probably pay attention.

• What are people joking about?
• What becomes funny because everyone recognises an element of truth in it?
• What can people comfortably say as a joke that they seem reluctant to say seriously?

Humour can be information. The question is whether we're listening.

When Leaders Become Afraid of Humour

There are good reasons for workplaces to take bullying, harassment and exclusion seriously. "It was only a joke" has been used plenty of times to excuse behaviour that wasn't particularly funny for the person on the receiving end. But there is a risk at the opposite extreme.

If leaders become so concerned about the possibility of offence that humour disappears altogether, they can inadvertently remove one of the ways teams build relationships, release pressure and challenge each other.

I've worked in environments where humour was extraordinarily direct. In the infantry, banter often crossed ranks, roles and personalities. Being able to laugh at ourselves helped build rapport and, particularly during difficult periods, provided a way to release pressure. When I transitioned into the private sector, I noticed a different level of caution. Some of that caution was entirely reasonable. But sometimes it went further. People became reluctant to joke, challenge or speak informally because they were uncertain how it would be received. And when people become overly cautious about how they speak, they can eventually become cautious about what they speak about. That's where leaders should pay attention.

Psychological Safety Doesn't Require a Humourless Workplace

A psychologically safe workplace isn't one in which nobody is ever uncomfortable or offended. It's one in which people can contribute, disagree, ask questions, admit mistakes and challenge ideas without an unreasonable fear of humiliation or retaliation. Humour can support that environment. It can flatten hierarchy. It can signal trust. It can make difficult subjects easier to approach.

But humour can also do the opposite. A joke made between trusted peers is different from a senior leader repeatedly making someone junior the punchline. A joke everyone participates in is different from one where everybody laughs except the person being targeted.

Context matters.

Which is why neither "someone was offended" nor "I was only joking" gives leaders enough information to make a good decision. We still have to exercise judgement.

Banter or Bullying?

The distinction isn't always straightforward, but there are a few things worth considering.

1. Intent and Impact

Intent matters. Someone deliberately trying to humiliate another person is very different from good-natured banter between people who trust each other. But intent isn't the only consideration.

If the same person repeatedly ends up embarrassed, excluded or diminished, "I didn't mean it that way" eventually becomes an insufficient explanation.

Good leaders consider both what was intended and what actually happened.

2. Problem or Person?

The best jesters tend to attack the absurdity rather than the individual. There's an important difference between making light of a ridiculous situation and making someone feel ridiculous. Humour can provide an extraordinarily effective way of challenging a problem without unnecessarily attacking the person associated with it.

That distinction takes skill.

3. Read the Room

There is a time for banter and a time for seriousness. Context, relationships, hierarchy and circumstances all matter. Something that works perfectly among a group of long-standing colleagues might land very differently with someone new to the team.

Good humour requires social awareness. So does good leadership.

Don't Silence the Signal

One of the most useful things leaders can ask themselves is what happens to information as it travels upwards. People filter. They soften bad news. They choose their language carefully. They anticipate how leaders will react before deciding what those leaders need to know. Sometimes the jester bypasses all of that.

They say the uncomfortable thing because they can make people laugh while doing it. That makes them valuable. It doesn't make them immune from boundaries, nor does humour provide a free pass for bullying, harassment or cruelty. But leaders should be careful about silencing people simply because their method of communicating makes us uncomfortable.

The joke might be inappropriate. It might also be telling us something.

Where Did All the Jesters Go?

Good leaders need people around them who are willing to tell them the truth. Some will do it formally. Some will do it privately. Some will challenge openly. And occasionally, someone will make the entire room laugh while doing it.

Those people require judgement from their leaders, not immunity and not automatic censorship. Because the real leadership question isn't whether humour belongs in the workplace. It's whether we can distinguish between humour that strengthens relationships and exposes uncomfortable truths, and humour that diminishes the people around us.

Be careful before beheading the jester. They might be the only person in the room telling the king the truth.