Why 'funny' often fails at work

What do late-night comedy writers know about trust, influence, and human connection that most business leaders don’t?

In this episode of Truth, Lies & Work, we’re joined by Beth Sherman — a seven-time Emmy-winning comedy writer who spent three decades in Hollywood writers’ rooms before taking what she learned into the world of business.

Beth has written for The Late Show with David Letterman, The Tonight Show with Jay Leno, Ellen, the Screen Actors Guild Awards, and the Oscars. Today, she works with leaders, sales teams, and organisations who want to build trust quickly, communicate with confidence, and connect more humanly at work.

This is not about telling jokes in meetings.

It’s about understanding why humour works, how truth creates connection, and why the most effective communicators are the most observant — not the funniest.

What you’ll learn in this episode

• Why “truth is funny” — and what that reveals about trust and rapport

• The difference between self-awareness and self-deprecation (and why confusing the two damages credibility)

• How humour creates psychological safety without undermining authority

• Why being human matters more as work becomes more automated and AI-driven

• How observational humour helps in sales, leadership, presentations, and difficult conversations

• Why you don’t need to be funny — you need to be emotionally intelligent and observant

Beth explains how comedians build instant rapport with strangers, and why those same principles are powerful in boardrooms, client meetings, and tense workplace moments.

Why this matters for leaders and teams

In a world where people can buy similar products, services, and solutions anywhere, relationships are the differentiator.

Humour, when used properly, signals:

• Awareness of the room

• Confidence without ego

• Safety without softness

• Humanity without oversharing

Beth’s work shows that humour isn’t about performance. It’s about connection — and connection is the foundation of trust, influence, and persuasion at work.

About our guest

Beth Sherman is a comedian, keynote speaker, and communication expert. She spent over 30 years writing comedy at the highest level before translating those principles into practical tools for business leaders.

Her upcoming book is published by Blue Goat Books.

🔗 Beth Sherman website: https://www.bethsherman.com/
🔗 Beth Sherman on LinkedIn: https://www.linkedin.com/in/beth-sherman/

🎧 Listen if you’re…

• A leader who wants to build trust without forcing charisma

• In sales or marketing and tired of scripts that feel inauthentic

• Giving presentations and feeling pressure to “perform”

• Curious about the psychology of humour and human connection

• Website: https://truthliesandwork.com

• Email: hello@truthliesandwork.com

• LinkedIn: https://www.linkedin.com/company/truth-lies-and-work

• Instagram: https://www.instagram.com/truthlieswork

• Al Elliott: https://www.linkedin.com/in/alelliott/

• Leanne Elliott: https://www.linkedin.com/in/leanneelliott/

🧠 Mental health support

If this conversation brings anything up for you or someone you care about:

• UK & ROI: Samaritans — 116 123 | https://www.samaritans.org

• US: Suicide & Crisis Lifeline — 988 | https://988lifeline.org

• Australia: Lifeline — 13 11 14 | https://www.lifeline.org.au

• Elsewhere: https://findahelpline.com