How to use humor to engage people in business communication

Executive overview

Audiences are conditioned to receive information with entertainment — competing for attention without humor means losing to those who use it. Humor isn't about getting laughs; it's a lever for engagement, dopamine spikes, and memory.

The core tools are accessible: a funny file of real stories, the rule of three (break the third item in any sequence), and self-deprecating stories that humanize without risk.

Funny people aren't born — they're made through writing, testing, and refining material the same way comedians do.

Why humor is a must-have, not a nice-to-have

• Audiences are socially conditioned to expect infotainment — news, content, even email
• Cold emails with strong humor achieved 50%+ open rates in A/B tests
• Funny follow-up emails generated a ~9:1 reply rate vs. standard follow-ups
• A dopamine spike from humor makes people more alert and more likely to act
• Even physical novelty (e.g., a stuffed groundhog on Groundhog Day) burns memory — clients recall it years later

Humor is a learnable skill

• Most people in the US say they aren't funny; in Ireland, everyone assumes they are — the difference is cultural expectation, not innate ability
• Famous comedians (including Louis C.K.) describe their first decade as awful; skill came from deliberate practice
• The common thread: great comedians are great writers who refine material systematically
• Becoming a better writer is achievable by anyone — it's the same underlying skill

The rule of three

• The smallest sequence the mind recognizes as a pattern is three items
• Comedy works by building expectation with the first two items, then breaking the pattern with the third
• This same structure underlies great copywriting, speeches, and memorable content
• Classic examples: knock-knock jokes, "three guys walk into a bar" — always three elements, always a twist on the third
• The most effective TED talks are funnier per minute than the funniest films, and they use this same technique

Building your funny file

• Start a list on your phone of anything you find entertaining — stories, images, overheard lines
• Focus on embarrassing or unexpected moments from your own life; embarrassment almost always contains humor
• Comedians and great writers all maintain a version of this — it's more enjoyable than journaling
• Use the file when writing blog posts, emails, or talks: find a relatable personal story, tell it briefly, delay the funny part to the end
• The structure: shortest possible setup → key moment → punchline last (this is what makes timing look good)

Self-deprecating stories over jokes

• Telling a story carries no visible risk — if people don't laugh, you just told a story
• Visible joke-telling creates a cringe moment when it fails; storytelling avoids that
• Poking fun at yourself or your organization is the safest entry point
• It humanizes you as a speaker and shares your perspective without forcing an opinion

Improv principles for everyday leadership

• Core improv rule: "yes, and" — accept any idea and build on it rather than shutting it down
• This opens creativity and forces exploration of an idea's strengths (or holes) before dismissal
• MIT study: improv practitioners generated more creative product ideas than experienced product managers
• Useful shift for leaders: replace "that won't work because…" with "tell me more — how would that work?"

Rehearsed spontaneity

• Material that looks improvised is almost always tested and refined in advance
• Martin Luther King's "I have a dream" section was not scripted that day — but he had referenced it ~350 times that year; he knew it landed
• Personal stories told at dinner or with friends are pre-tested; restructuring them so the punchline comes last makes them ready for professional use
• Audiences credit speakers for improv when the material is actually rehearsed — the effect is the same

Managing Q&A and endings

• Ending on a Q&A session risks an awkward, flat close
• Better structure: take questions before your conclusion, then deliver a three-part closing
• Tell the audience upfront you'll take questions before your conclusion — they know something is coming, so you can cut Q&A at any moment
• A strong, planned closing makes the talk memorable and gives a clean video ending