In business, we’re told to keep things serious: set KPIs, watch margins, deliver impact. But the unspoken truth? Some of the most successful leaders are the ones who know when to crack a well-timed joke. Humour, used wisely, doesn’t just make you likeable – it makes you lethal in the best way. That’s funny business!
But humour isn’t risk-free. When wielded poorly, it can land with the grace of a dad joke at a funeral. And yet, done right, it can slice through tension, rewire a stressed-out team, and turn failure into forward momentum.
So, should leaders laugh more – or are we in danger of becoming clowns at the top?
Humour as a Hidden Lever for Leadership
According to a revealing article from PsychCentral
Humour is one of our brain’s most powerful coping mechanisms. It’s a form of emotional triage. When things go sideways – whether in a pitch meeting or a public scandal – the right kind of laughter doesn’t deflect, it connects.
But here’s the edge: not all humour is created equal.
The research identifies four styles:
- Affiliative: good-natured, team-building, the kind that bonds rather than bruises.
- Self-enhancing: finding amusement in your own stumbles, showing you’re human.
- Self-defeating: mocking yourself to win approval (often at your own expense).
- Aggressive: the sarcastic, sneering stuff that scores cheap laughs but burns bridges.
Good leaders play in the first two categories. Bad leaders? They often drift into the last two and wonder why no one’s laughing.
Why This Matters More Than Ever
We live in tense times. Layoffs, AI anxiety, economic uncertainty – it’s a comedy club of corporate dread out there. And when stress rises, people look for permission to exhale.
As Rick Wilson said on The Humourology Podcast:
“Humour is an expression of the authenticity of the character of your leadership… it connects people with who you are – and you can’t buy that with advertising.”
Humour is the perfect tool for doing just that. It cuts through tension, invites perspective, and reconnects people in a way few other things can. A well-timed laugh doesn’t just lighten the load – it reminds us that we’re in it together.
But here’s the danger: when humour becomes a habit of avoidance rather than connection, it starts working against us.
The Boris, the Buffoon, and the Boardroom
A brief aside into politics. British culture famously defaults to a joke in times of crisis – what the Financial Times called “laughing itself stupid.” Case in point: Boris Johnson. He used bumbling charm and Etonian eccentricity to sidestep scrutiny, all wrapped in self-deprecating humour. For a while, it worked. Until it didn’t.
Meanwhile, Rick Wilson and The Lincoln Project took the opposite approach – weaponising humour to dismantle the pomposity of authoritarian figures like Donald Trump.
“Authoritarians are fragile,” Wilson noted. “Humour is their kryptonite.”
Whether in politics or business, the lesson is the same: humour can humanise – or hypnotise. It can cut through spin – or camouflage it entirely. The difference? Intention.
Three Tips to Use Humour Like a Pro (Not a Punchline)
- Read the Room (Then Read It Again)
If your team’s in crisis mode, now is not the time for ironic asides or sarcasm. Humour should meet people where they are emotionally – not mock them from above. - Start with Yourself
Self-efacing humour is magnetic. Laugh at your own foibles and you create psychological safety. No one wants to follow a flawless robot. But a leader who says, “Well, that went badly – but at least I didn’t fall off the stage again,” earns respect and relief. - Keep the Punching Up, Not Down
Aggressive humour might win applause from one or two allies, but it poisons culture over time. Your jokes should elevate the team, not divide it. You’re not auditioning for open mic night. You’re leading.
Final Laugh (And Serious Point)
Humour isn’t just something leaders can use. It’s something they must learn to use well. When things go wrong – and they always do – it’s not the stoics who rally teams. It’s the ones who can reframe failure, lift spirits, and remind us we’re all human.
Or as Rick Wilson so aptly put it:
“The idea that you can look at the worst moments and find something about them to mock or to make lighter – I think that’s a really strong character trait… and if you don’t take yourself too seriously, you’re more resilient, more authentic, and a hell of a lot more fun to follow.”
So yes – laugh. But lead while you do it. That’s the real punchline that lands.
See you next Tuesday.
Warmest,
Paul x
