The serious business of joking around at work (and why it’s worth getting right)

If you’ve ever watched The Office, you’ve probably heard this infamous line: “That’s what she said!”

It's delivered by Michael Scott, the bumbling but well-meaning boss played by the inimitable Steve Carell in the American sitcom.

Michael is the poster child for “self-unaware” managers. He fancies himself a comedic genius, but his humour lands about as gracefully as a drunk uncle at a wedding. 

His go-to move? Reframing innocuous comments with wildly inappropriate sexual innuendo.

Michael’s supervisor: “I want you to think about this long and hard.”
Michael: “That’s what she said!”

On television, this exchange works because it highlights Michael’s lack of self-awareness, making him the joke rather than the innuendo itself. 

In a real workplace, however, this kind of humour is inappropriate and, frankly, not all that funny.

Joking around at work feels like it should be simple – until it isn’t. 

Done right, it’s the secret sauce that makes dull days bearable and stressful moments manageable.

Done wrong, it’s an express ticket to awkward silences, strained relationships, or worse – a summons from the human resource department or a company-wide Slack message reminding everyone about “appropriate workplace conduct”.

That sounds a little risky given the potential fallout.

WHY HUMOUR MATTERS (AND WHY IT’S WORTH GETTING RIGHT)

With the points above in mind, is humour in the workplace even worth the effort? 

It absolutely is – and here’s why:

1. It brings people together

A good laugh can turn colleagues into co-conspirators. Whether it’s an inside joke about the printer’s perpetual paper jam or a shared groan over Monday mornings, humour fosters connection.

2. It’s a stress buster

Work can be stressful. Deadlines loom, emails pile up and sometimes, it feels like the office coffee is the only thing keeping you alive. A shared laugh cuts through that tension like nothing else.

3. It sparks creativity

Humour shifts perspectives. It’s no coincidence that funny people often think outside the box – laughter creates an environment where it’s safe to share wild ideas.

THE RULES OF WORKPLACE HUMOUR

We’ve all encountered two kinds of colleagues: The ones who can crack a joke that brightens the whole room, and the ones whose attempts at humour bring to mind the Jonah Hill “cut it out” GIF. 

The difference? Knowing where the line is.

1. If it’s “probably offensive”, don’t say it

If you feel the need to preface a joke this way, you already know you shouldn’t say it. Your inner voice is like a mini compliance officer – listen to it.

The Tripartite Alliance for Fair and Progressive Employment Practices in Singapore provides guidelines on workplace communication, and discourages jokes or remarks that target individuals or groups based on race, gender, religion, age, disability or any other protected characteristic. So you would want to avoid any of those subject matters in the workplace altogether. 

This isn’t about “being woke” or “cancel culture”. It’s about basic respect for others. Ultimately, we want to keep the office a safe, shared space for everyone. 

So unless you’re a professional comedian headlining at Marina Bay Sands, keep your quips strictly SFW.

2. Punchlines shouldn’t punch down

There’s good-natured teasing and there’s bullying. Targeting a colleague – especially someone in a junior role or with less power – is a one-way ticket to becoming that boss.

Thinly veiled sarcasm is no better: “Wow, I didn’t know you used to be me. How else can you ‘revert’ to me?” (Sorry – I’m guilty of this one.)

It might seem funny to you in the heat of the moment, but really, it’s just passive-aggressive – and it breeds resentment faster than you can say “mandatory team-building retreat”.

If the joke doesn’t uplift the atmosphere or your co-workers, don’t say it. Save your snark in the draft folder of your conversational outbox. 

3. Read the room

Humour is as much about timing and delivery as it is about content. Got a killer joke about the company’s expense policy? Great – but maybe don’t drop it during a meeting about budget cuts.

And if your joke bombs, or if you inadvertently made an inappropriate joke, this is what you should do.

• Own it: “Wow, that was inappropriate. I shouldn’t have said that. Sorry!”
• Don’t double down: Saying “Why so serious? It’s just a joke” makes it worse.
• Move on: Everyone misses the mark sometimes; the key is not to make a habit of it.

4. “Laugh with”, not “laugh at”

Making fun of yourself? Great. Joking about the office bidet erupting like an Icelandic geyser again? Go for it.

But if your joke makes someone feel small or excluded, it’s not funny – it’s just mean. 

Conversely, jokes about shared experiences (like the universal struggle of logging into the new employee human resource portal) land because they’re relatable and inclusive.

SO, WHERE’S THE LINE?

Humour in the workplace isn’t just about seeing things lightly; it’s seeing things in a different light. It reminds us that even in the face of the most soul-crushing of workloads, we’re all in this together. 

So where should the line be, then? It’s simple, though not easy. 

The rule of thumb is this: If the joke lightens the mood and brings people together without stepping on toes, you’re in safe territory. If it feels even slightly sketchy? It never hurts to leave it unsaid.

Because let’s face it: Nobody wants to be the reason for next quarter’s mandatory sensitivity training. Or worse, the subject of the company’s newest “case study” on workplace misdemeanours.

Michael Scott once said: “You miss 100 per cent of the shots you don’t take. – Wayne Gretzky.”

So shoot your shot when it comes to using humour at the workplace, but first, think about it long and hard. 

And if you miss? Own it and learn from it. 

Kelvin Kao is the co-owner of a creative agency and a cafe.