Well, That Was Unexpected!

Why funny speakers land the hardest truths

There’s something oddly satisfying when a speaker says what everyone’s been thinking but no one has the guts to say - especially when it comes to workplace culture.

When a speaker can turn endless meetings, buzzword salad and performative wellness days into laugh-out-loud moments, they’ve done what few speakers can: get and keep the audience’s attention, while also successfully disarming the room.

Humour sharpens the truth

Speakers who use comedy well aren’t actually making light of serious topics. They’re using light to expose what’s been lurking in the dark corners of the internal Teams channel.

They demonstrate how the dysfunctions we’ve normalised and the rituals we’ve ritualised now reach a point where we can’t tell what’s helpful from what’s hollow. Think of it less as stand-up and more as a cultural audit, but with better timing.

When done right, humour creates a rare kind of safety. It gives people permission to let down their guard, breathe out, and say, “FINALLY. Someone’s said it out loud.” And that moment of recognition can be priceless when it comes to initiating change.

Too often, organisations default to “safe” speakers – earnest, credentialled, heavy on frameworks. Sure, there’s a place for that. But when employees are saturated with politely phrased strategies and inspiring TED Talks, a dose of levity can unlock the kind of real talk that PowerPoint can’t.

Skilled, funny speakers

What do skilled, funny speakers manage to achieve?

• They expose shared truths without making anyone feel…exposed.

• They use character, story and timing to keep the audience engaged.

• They shift the energy in the room from polite listening (and sleeve-covered yawning) to genuine interest.

• They leave people feeling seen and lighter, not lectured.

• They open the door to difficult topics for discussion with management.

  
  

There’s also the trust factor. People tend to trust speakers who make them laugh. Laughter feels honest - and in corporate spaces, that alone can change the game.

The best part? You can spark convos that would never come from an HR-approved email.

But catharsis alone isn’t the point 

The best funny speakers nudge the room – gently and cleverly – into asking: “Why do we work this way? Is this worth it?” That’s where the magic happens: the laughs lead to a pause and hopefully, a shift in perspective.

If you’re thinking about using humour in your keynote or booking someone who does, consider how laughter can create the kind of environment where people feel safe enough to acknowledge and talk about what’s really going on.

And besides, if the finance and IT teams laugh even once, you have yourself a win.