Eight Moments That Got Big Laughs at 2026 Annual Investor Meetings

Welcome to my second annual blog on the best use of humor at global annual meetings across investment, private equity, and financial services. (For the first blog from 2025, click below)

https://www.linkedin.com/pulse/eight-moments-got-big-laughs-annual-investor-meeting-sjrme/

As always, I spent most of May with some trusted colleagues, helping with speaker coaching for their annual investor meetings. After the coaching, whether for solo presenters, pairs, or business‑unit groups, we’re often onsite for the dry run and the event itself, timing each talk and capturing specific feedback for every speaker.

Even though most AGM speakers I meet with have been presenting for many years, even decades, the most impressive presenters are the ones still looking for feedback on small ways to add polish or impact.

What gets a room of smart investors- people who attend hundreds of meetings a year- to laugh?

Luckily, it’s not stand‑up comedy, telling a joke, or something random you found on the internet. I’ve done the analysis for you below to break down what gets a laugh and why. Use these ideas to add levity to your next update or presentation.

Here are eight of the best laugh‑out‑loud moments I witnessed at various 2026 AGMs. Details have been changed for client confidentiality, but the heart of each example is exactly what got the big laughs.

1. The callback to history

A leader opened by joking, “I presented this same slide to Jack more than a decade ago.”Why it works: shared history + institutional memory + self‑awareness + everyone loves a joke about slide decks.

2. The unexpected confession

A highly accomplished industry expert admitted he would never have predicted this career path given his poor grades. The room loved it.

In another segment, a speaker asked a difficult question and said, “So what’s the answer? (pause…) Well, even I had to ask Claude.”Why it works: competence + humility is an extremely likable combination.

3. Admiration disguised as teasing

“I was hoping she wouldn’t be at this meeting today.” Translation: this person is terrifyingly smart or a high performer, so we can joke that we don’t want her around while we’re presenting. Why it works: it gives a colleague public credit without sounding overly fawning.

4. The oddly specific origin story

Not the same old vague “we built a great partnership,” but the strange little story about where it actually started: “Tampa lightning storms, three delayed flights, a random introduction over $47 airport burgers…”Why it works:specificity makes people smile and remember.

5. The elephant in the room

“I’m aware we’re a bit behind schedule, and also that I’m the only thing standing between you and lunch.”

If the room is freezing, everyone knows. If lunch is late, you can feel the fidgeting. If your session title sounds like a doctoral dissertation, everyone is worried it will be dry. Why it works: a quick acknowledgment creates an instant connection.

6. The ‘we’ve all done this’ moment

“I was told by one highly esteemed CEO back in 2023 that ‘AI will always be completely unfit for professional use.’”

We laugh at outdated attitudes (smoking on airplanes?!), at how wrong we were about a deal, or at universally embarrassing human behavior. Why it works: shared recognition builds immediate trust.

7. The visual surprise

Unexpected old photos. A bingo card of impossible tasks. A before‑and‑after video. Rooms are visually starved, and most slides read like awful eye charts. Why it works: a smart image, video segment, or physical item immediately changes the energy.

8. The rule of three

This works because rhythm is effective, and using three items is effective in many settings.

“I didn’t want to pay airport coffee prices. I didn’t want another 4 AM alarm. And I definitely didn’t want to be the final speaker of the day.”

Why it works: catchy structure + acknowledging we’re all tired + unexpected confession = laugh opportunity.

I could have easily added more, but it’s a good challenge to stick to eight observations. Humor in senior rooms is rarely about “being funny” or telling jokes. We want to hear about your fears, missteps, inner dialogue, thought process, challenges, and failures. We want to be surprised. We want to learn. We want to feel connected.

If you can add humor successfully as a presenter, you’ve tapped into the thrill of true human connection. Give some of these a try and let me know how it goes.

Author

Spread the love

Authors

MORE POSTS

Save Time and Money with Better Communication

I’m sitting in a meeting, internally rolling my eyes, because “Chad” has hijacked it again. At this point, his voice is like fingernails on a chalkboard to me, as he repeats the same tired axe that he always grinds. This meeting isn’t even about what he’s talking about! And I can’t help noticing that he’s wrong about some of the things he’s saying. I choose not to engage because I’ve learned from past attempts that

Spread the love
woman speaking with confidence

The 5 Types of Talking You Do Every Day

Between human nature and the English language, there are so many nuances that it can often cause confusion or major conflict. Without putting on my Rhetorician’s hat, allow me to give a brief description of a few ways we interact verbally. This delineation will help you identify not only the type of talk you are engaged in but also whether it is productive. While a case can be made for each of these having a

Spread the love
Executive delivering high-impact business presentation

Why is the Listener so Important?

Just as breakfast is often considered the most important meal of the day, analyzing who is listening to us speak is one of the most important parts of speech preparation. Unfortunately, as with breakfast, analyzing who is listening to them is a step speakers often skip. Generally, when an executive is asked to be on a panel, give a keynote, appear on a podcast, or even present to a board of directors, they go straight

Spread the love

QUESTIONS? NEED HELP?

Tell us what’s on your mind: