After last week’s Humourology conversation with Jeremy Lee, a man who has spent much of his professional life placing fascinating human beings in front of even more fascinating audiences, I found myself reflecting on a slightly uncomfortable truth.
In modern business culture, the biggest risk is often not taking one.
For decades he watched comedians, politicians, economists and broadcasters step onto stages knowing that within seconds a room would decide whether they were credible, compelling or quietly doomed. Sometimes the stakes were reputational. Occasionally, they were existential. They were always immediate.
When performers such as Omid Djalili or Jo Brand take a risk, we recognise it instinctively. The audience leans in. Energy lifts. Courage creates connection.
Yet in boardrooms and corporate town halls we often witness the reverse. Leaders default to safe language. Sanitised messaging. Carefully polished phrases that have been through so many approval loops they emerge linguistically intact but emotionally anaesthetised. Playing safe feels like the new norm.
It is not a question of intelligence. Many of the figures Jeremy worked alongside over the years, from formidable political operators to heavyweight thinkers such as Mark Carney, possess intellect in industrial quantities. But intellect alone rarely holds a room.
Psychological connection does.
Jeremy spoke with particular warmth about representing William Hague for many years. He observed how William’s intellectual clarity, dry wit and instinctive timing gave him a rare ability to engage audiences without ever appearing to try too hard. William, of course, was a brilliant guest on The Humourology Podcast and his reflections on communication and leadership remain strikingly relevant. Influence, as both men understand, is seldom about volume or status alone. It is about rhythm, emotional intelligence and the confidence to reveal the human being behind the title.
One paradox of professional success is that the higher people rise, the more allergic they become to looking foolish. Status becomes armour. Humour begins to feel like reputational Russian roulette. Language shifts from vivid to vague.
Corporate-speak drifts in like a scented candle at a strategy retreat.
The result is not merely dull communication. It is diluted influence.
From a Humourology perspective, humour functions as a kind of social truth serum. It punctures inflated rhetoric and reveals whether ideas are genuinely landing or simply being endured with polite nodding. This is why performers develop such finely tuned instincts about audience mood. Silence is information. Laughter is feedback.
n leadership psychology we might describe this as calibrated vulnerability. Amy Edmondson’swork on psychological safety suggests that when leaders reduce interpersonal threat, people are more willing to engage, contribute and take constructive risks. The trick is balance. Appearing human without surrendering authority. Projecting confidence without pretending to be infallible. Laughing with an audience rather than speaking at them.
It is also why some of the most effective communicators Jeremy encountered were those willing to deflate their own seriousness. There is a certain future Prime Minister who, long before Downing Street beckoned, understood the value of a well-timed self-deprecating remark. Not every quip was a triumph, but the willingness to risk mild embarrassment and the refusal to be thought of as playing safe often created momentum that safer contemporaries struggled to generate.
This dynamic extends far beyond politics and performance. Entrepreneurs pitching investors, executives leading transformation programmes and teachers attempting to hold the attention of a roomful of teenagers all face the same challenge. They must balance credibility with warmth. Strategy with spontaneity. Gravitas with a glint in the eye.
Humour, used wisely, becomes the bridge.
Another idea that lingered after our conversation was luck. Not mystical destiny, but the rather sobering recognition that timing and context play enormous roles in success. You can prepare meticulously, build impressive networks and craft persuasive messages, yet outcomes often hinge on variables no spreadsheet could predict.
Humour helps here too. It keeps ego proportionate and mindset flexible.
If we can smile at the randomness of professional life, we become more resilient when plans wobble. We also become more alert to unexpected opportunities, which frequently arrive disguised as inconvenience.
Jeremy explores many of these themes on his own podcast, Just Between Us. If you have not yet listened, it offers an entertaining and insightful glimpse into the psychology of influence and what really happens behind the scenes when public figures prepare to face a room.
Perhaps the deeper lesson is this. Playing safe may preserve comfort, but it rarely creates memorable impact. A measured willingness to risk looking slightly ridiculous can be one of the most powerful leadership tools available.
See you next Tuesday.
Warmest,
Paul x
In case you missed it, here’s last week’s episode featuring Jeremy Lee
