How often have you attended a conference, listened to a series of presentations, or been subjected to a training or professional development seminar only to leave the event, stop in the restroom before you exit the building, and climb into your car having forgotten almost all that was said? Or even worse, wanting to forget all that was said?

How much of the last presentation that you watched (or were subjected to) do you remember?

How much of the last deck you saw can you recall?

When was the last time a speaker or presenter genuinely excited you? Made you want to race home to tell your spouse or business partner what you heard? Inspired you to think or live or see the world differently?

The problem is simple: People mistakenly assume that, because they have the authority and expertise to warrant speaking on behalf of the company, others will automatically want to hear what they have to say. The higher a person rises in a company, the more often that assumption is baked in.

But audience attention and engagement are not givens. If there is no attempt to entertain, then even when someone has important, relevant, or useful information to share, the audience will often be disengaged, disinterested, and distracted, and so miss and not even remember the good stuff.

However, CEOs don't like being told that no one cares what they have to say unless they give their audience a reason to care. This news is often poorly received and rejected outright. But it's true for any public speaker: Even when we have the authority, the stage, and the microphone, the audience will not care who we are or what we're saying unless we make it interesting for them. Once we open our mouths and start talking, no amount of power, position, resume, or introduction will save us if we are not entertaining.

Entertaining can sometimes be a polarizing word. When I tell a scientist who is going to present their findings that they need to be entertaining, they bristle. When I tell a CEO that their keynote needs to be entertaining, they look at me like I have two heads.

Most of the time, people think "entertaining" means being "funny." In order to be entertaining, we need to crack jokes.

This isn't entirely wrong. Humor is an excellent way to be entertaining, and everyone in business — without exception — could stand to be more amusing. We know that laughter alters brain chemistry in enormously powerful and beneficial ways. Advertising often leverages the power of humor to create memorable, profitable assets that grow the bottom line. People adore comedians.

And occasionally businesspeople are funny. Warren Buffett and Charlie Munger's famous Q&A sessions at Berkshire Hathaway's annual shareholder meeting included humor. In almost every Steve Jobs keynote, he used humor. Even the most sober commencement speakers and the most academic TED speakers find moments to be funny.

Funny is entertaining. People like to laugh. People like people who make them laugh. It's probably how I first attracted my wife's attention. It's probably the only way I'm keeping her attention.

But good news: Not only can you learn how to be funny, but humor is only one way to be entertaining. There are many other ways, and the rest of this article provides you with the best options. Don't pick one; use them all.

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1. Tell a Story

This one should be obvious by now. Expected. Storytelling changes brain chemistry for the better, and stories, when told well, are entertaining, highly relatable, deeply connective, and unforgettable.

So when delivering a keynote, address, or investor pitch, tell not just one story, but several. Make sure one includes humor.

Years ago, I worked with a cybersecurity company, helping them with their marketing and sales. I don't remember much about the actual work we did, but I remember the story we told about hackers accessing Target's computer system through the company's rooftop HVAC systems in order to steal tens of millions of credit card numbers.

Why?

It was a story. It was the Mission: Impossible of the corporate world. Instead of Ethan Hunt breaking into CIA headquarters via the air ducts to steal the "Non-Official Cover" list, cyber thieves used the heating and ventilation system to penetrate one of the largest retailers in the world to retrieve data worth millions of dollars.

That was a crime, and the story of that crime is very entertaining.

Also memorable, relatable, and the kind of story people can't wait to share.

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2. Be Vulnerable

We can express vulnerability by saying the things that few are daring or courageous enough to speak. In doing so, we demonstrate confidence. We do something that few people are willing to do, which is almost always entertaining. We're also very likely to connect with members of our audience in deeply profound ways.

You can be vulnerable like the CEO of Yale New Haven Hospital when she talked to her people about her husband's problematic knee surgery in her own hospital. You can be vulnerable like Domino's Pizza when they admitted that their pizza sucked. You can be vulnerable like Reed Hastings, CEO of Netflix, when he acknowledged the stupidity of Qwikster, apologized for his poor decision-making, and quickly dismantled the initiative.

In each of these cases, respect was earned, and loyalty was ensured by leaders who were willing to admit imperfection and respond with graciousness and vulnerability.

I'd watch that any day.

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3. Offer Fascinating Information

My family and I recently visited Alcatraz and listened to a talk about the many attempted escapes back when the island was still a prison. The person delivering the talk was highly ineffective. She used an enormous number of filler words. She forgot parts of her talk multiple times and was forced to circle back to previous content to clear things up. She repeated herself frequently. Paced nervously. Spoke in a flat, monotone voice.

She mispronounced windswept.

It was a disaster.

It was also riveting.

That's because stories of attempted escapes from an island fortress are fascinating. Hardened criminals digging through concrete walls with kitchen spoons, donning hastily fashioned military uniforms in order to stow away on supply ships, bending bars and greasing their naked bodies to squeeze between the metal, and making daring leaps into frigid, unforgiving waters … even the worst public speakers in the world can't ruin this content.

It's just too damn good.

People love to learn, especially when the information is new, upends previously understood facts, allows them to see the world through a new lens, brings clarity to opacity and simplicity to complexity, and is easily shareable. If you have content — facts and figures, history and science — that people find interesting, you will be entertaining.

Did you know that Abraham Lincoln's eldest son, Robert Lincoln, was once saved from death on a train platform by Edwin Booth, the brother of his father's assassin, John Wilkes Booth?

Did you know that supermarket apples can be as much as a year old?

Did you know that in the 1840s, it was considered childish to smile for pictures, so it became popular for people to say "prunes" instead of "cheese" in order to keep their mouths taut?

I find these facts endlessly entertaining, and they remain entertaining even when shared by someone who is themselves, like the Alcatraz guide, not entertaining.

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4. Be Novel

People love to see what they have never seen before. When we can do something that has never or rarely been seen before, it will almost always be entertaining, even when it seems like it will not.

This is how comedian Andy Kaufman managed to make audiences laugh by simply sitting on a stage, playing the Mighty Mouse theme song, and doing nothing else.

This is how Memento, a film that tells its story in reverse, became a cult hit. Or how the seemingly authentic footage in The Blair Witch Project made that film an enormous success. Or how the mixed animation style of SpiderMan Across the Spider-Verse made it a visually stunning hit.

Stories told in novel ways are entertaining and unforgettable.

It's how Pink's trapeze performance during the 2010 Grammys became one of the most memorable moments in the show's history.

As corny and awful as it was in 1995 — and remains today — it's also why Bill Gates, Steve Ballmer, and other Microsoft executives danced onstage at the release of Windows 95. They had just announced a transformational product that would change the world, and while most businesses would remain buttoned up and sober, the Microsoft team did the opposite. They danced in a way that made it clear that they had done very little dancing up until that point. It was cringy and odd and overenthusiastic. It may be some of the most awful dancing ever seen, but there's a reason why it's been viewed online hundreds of millions of times: It's entertaining.

If every executive team of every Fortune 500 company danced at the announcement of a new product or innovation, Gates and Ballmer's enthusiasm would be forgotten today, but when something is novel, we remember.

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5. Inspire

People want to be inspired. Even the most cynical monster can't help but be inspired by soaring words, a great comeback story, or an underdog achieving greatness.

There are many ways to inspire people.

President John Kennedy inspired a generation by setting a lofty, seemingly impossible goal of putting human beings on the moon in ten years. He said, "We choose to go to the moon in this decade and do the other things, not because they are easy, but because they are hard."

Activist Greta Thunberg inspired a generation of young people by sailing across the Atlantic to avoid a carbon-intense flight in order to shame world leaders on one of the world's largest stages — the United Nations — with the words, "How dare you?"

Captain America inspired an army of humans, aliens, a Norse God, a cybernetic raccoon, and Howard the Duck to battle the forces of evil with just one word: "Assemble."

In speaking that word, he also made audiences cheer with delight.

Steve Jobs inspired a generation of nerds through the relentless demonstration of his passion for technology, design, and art.

Appeal to an audience's better nature or champion what they love, and they will listen.

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6. Offer Choice

Human beings are happier when they have control over their lives. This can include allowing them to choose their seat, opt for the talk they most want to attend, create their own group assignment, and the like.

Nothing will annoy a person more than entering a conference room and finding they have been assigned a seat beside Phil. Such seating assignments are infantilizing, disrespectful, and in the case of Phil, depressing.

More controlling presenters will insist that laptops be closed during a meeting. They forbid the eating of food. They identify predetermined restroom breaks, sometimes referred to as "bio-breaks," which is a horrible way to describe anything. They might force awkward icebreakers on audiences. Children bristle at these attempts to control. Adults loathe them.

Removing choice unnecessarily is also the enemy of entertaining.

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7. Invite Audience Participation

This isn't appropriate in every context, but one way to be entertaining is to invite people to participate, respond, or contribute during a presentation. This can be as simple as taking a straw poll, inviting someone to share an experience or story, or asking audience members to shout out prompts, ideas, or answers.

During my recent solo show, I brought my baby book into the audience and invited people to confirm that the four names my mother listed under "Prominent People" on the day of my birth were consumer advocate Ralph Nader, former president Richard Nixon, Lieutenant William Calley (convicted of murdering twenty-two unarmed Vietnamese villagers in the My Lai Massacre), and mass murderer Charles Manson.

In my baby book.

People loved watching audience members scan the list in disbelief.

One of my clients, Dynamic Information Solutions, sends out a regular newsletter called "Eight Bits Make a Byte" that invites readers to tweet responses about the content to them. It's usually phrased in the form of a question, but people can also let the company know anything they'd like about the newsletter. Sometimes those responses serve as the basis for future newsletters.

The power of audience participation is the reason why radio stations feature the voices of listeners requesting a song. It's why audience-reaction videos to great movie moments have become so popular on YouTube. It's why sporting events encourage fans to cheer and shout for their favorite team. Home fans of the NFL's Seattle Seahawks are known as the "Twelfth Man." They are so loud that they are part of the action and contribute to team performance.

A little bit of audience participation can considerably increase your chances of being entertaining.

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8. Invite Competition

Again, this doesn't always work in a speech, but people love competition. Challenge an audience to listen carefully for something important in your talk, then use technology — Kahoot-like products — to quiz the audience at the end to see who recalls the most.

Or have one side of the audience compete against the other side in simple games like these:

• "Which side of this auditorium is the most excited about this product launch?"
• "Who flew the most miles to be here?"
• "Who hates Phil the most?"

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Putting It All Together

The best storytellers combine all these approaches, or as many as possible, to make something truly entertaining.

Megan Washington is a brilliant example. Washington is an award-winning musician and songwriter from Australia who stutters. She publicly revealed her struggle with stuttering for the first time during a 2012 TEDx Talk in Sydney. Over the course of almost thirteen minutes — of which she spends the last five minutes singing — Washington does almost everything a speaker can do to be entertaining:

She tells stories about her struggles with stuttering.

She's constantly funny, bringing the audience to laughter again and again.

She offers fascinating information on stuttering, including the strategies she uses to "trick her brain" when she feels like she's about to stutter, her struggle with pronouns, and the "miraculous" fact that it's impossible to stutter while singing.

She's as vulnerable as a person can be, telling the world that she is a performer — a person who makes her living onstage — who suffers from a significant speech impediment.

She's inspiring. I have watched her talk dozens of times, and I am still nearly brought to tears each time she moves to the piano to sing her song.

And she's novel. She's doing a TEDx Talk, but she also performs an entire song that is perfectly fitting for her topic.

It's as good of a talk as you'll ever see (check it out for yourself below), and it's entertaining as heck.

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People are entertaining. Corporations are not.

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How to Be Funny

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Copyright ©2024 by Matthew Dicks. All rights reserved.

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Excerpted from the book Stories Sell: Storyworthy Strategies to Grow Your Business and Brand ©2024 by Matthew Dicks. Published with with permission from NewWorldLibrary.com.

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