Humor as Strategy

Turn skeptics into believers and make remarkable progress.

Embrace Humor to Build Connections

In my checkered past at Apple, I was in many tight situations because of the lack of software, financial shortfalls, layoffs, and executive suite drama. To defuse situations and to build connections, I resorted to three gems of humor:

1. Q: “How many Macintosh Division employees does it take to screw in a lightbulb?” A: “One, the employee holds up the lightbulb and expects the universe to revolve around him.”

2. Q: What is the largest group of migrant workers in California?” A: “Apple marketing.”

3. We thought of holding a communications meeting for people who wanted to quit because we were making so many mistakes and executing so poorly. Then we would fire everyone who didn’t come to the meeting because they weren’t thinking critically and rebuild the company with the people who wanted to quit.

(You can adapt this last story to government these days, but I digress…)

The takeaway? Humor is a powerful tool to connect with people, even in high-stakes situations. It shows confidence and an awareness of the absurdity of life, and it breaks down barriers and makes you relatable. When you can laugh at yourself or your challenges, you invite others to trust and engage with you.

Show Confidence in Your Beliefs

That moment wasn’t just about humor—it was about conviction. I believed so deeply in the Macintosh that I could joke about Apple’s struggles without undermining my message. That confidence resonated with the audience and made them more willing to listen.

When you’re pitching an idea, product, or vision, your belief in it has to be unshakable. People can sense when you’re not fully committed, and it’s a dealbreaker. Confidence isn’t arrogance—it’s the quiet assurance that you’re onto something remarkable.

Use Authenticity to Win People Over

The people who heard me tell those stories weren’t just buying Macintoshes or writing software. They were buying into the Macintosh Way. They wanted to believe in Macintosh as a platform and Apple as a company.

In a world full of polished pitches and corporate jargon, authenticity stands out. Be yourself, flaws and all. People don’t want perfection—they want realness. When you’re genuine, you create a connection that no amount of slick marketing can replicate.

Turn Challenges into Opportunities

Let’s face it: Apple wasn’t exactly dominating the market back then. The Macintosh was a long shot, and everyone knew it. But instead of shying away from that reality, I leaned into it with humor and optimism.

Challenges are inevitable, but how you handle them defines your success. When you face obstacles with creativity and resilience, you not only overcome them—you inspire others to do the same. Every challenge is an opportunity to prove your mettle.

Inspire Action with a Memorable Message

If you want to inspire action, your message has to be memorable. Don’t be afraid to take risks with your words. A little humor, a little edge, and a lot of heart can make all the difference.

This story isn’t just about a funny moment—it’s a blueprint for how to connect, inspire, and lead.

Use humor, authenticity, and resilience to turn skeptics into believers and make remarkable progress.

Mahalo!

Guy