Why Your Jokes Are Probably Costing You More Than You Think

Clean, healthy humour is genuinely hard to do well. And in the workplace, most attempts by leaders fail — not because leaders are not funny, but because the power dynamic makes it almost impossible for a joke to land authentically when you are the one with authority.

Think about it this way. My executive assistant laughs at my jokes even when they are not funny — not because she wants to, but because it is easier than the awkward silence that follows if she does not. That forced laughter is exhausting, and it is happening in meeting rooms everywhere.

The problem is not that bosses should not have a sense of humour. It is that they often do not realise the power dynamic changes how humour lands entirely. Your audience is not free not to laugh. So when you bomb — and most attempts do — you have just made everyone uncomfortable and burned their energy pretending otherwise.

Professors of Marketing and Management Peter McGraw, Adam Barsky and Caleb Warren have studied workplace humour extensively. Their research shows humour is far riskier than people think. They developed what they call benign violation theory — the idea that comedy works when something is both wrong and okay at the same time. Miss that balance, and you do not just bomb. You break trust. Their studies found that when managers use humour ineffectively, they lose status and credibility. Employees are less likely to respect them, seek their advice or trust their leadership. Even worse, employees burn out from having to fake amusement when bosses joke too often.

Telling a great joke rarely gets you promoted. Cracking a bad one can cost you real respect.

So what do you do instead? Stop trying to be funny. Start being aware. If you are the senior person in the room, recognise that your humour comes with a power imbalance. People laugh because you are the boss, not because you are hilarious.

If you want to use humour to build connection, flip the script. Instead of trying to make people laugh at something, invite them to laugh with you. Make yourself the subject — share the mishap, the mistake, the moment you got it wrong. Not so much that it undermines your credibility, but enough to show you are human too. Because the best workplace humour does not come from the boss trying to entertain. It comes from leaders who create space where everyone feels safe enough to be real.