6 Creative Ways to Make Your Executive Brand Memorable
Public Relations Advice
6 Creative Ways to Make Your Executive Brand Memorable
In the competitive world of executive branding, standing out is crucial. This article explores unconventional yet effective strategies to make your executive brand truly memorable. Drawing from expert insights, these creative approaches range from viewing brand strategy as a love letter to using humor in presentations and even incorporating tech jargon jokes to break the ice.
- Brand Strategy as a Love Letter
- Rubber Chicken Leadership
- Coffee and Resilience
- Humor Humanizes Executive Presentations
- Tech Jargon Jokes Break the Ice
- Investor Pitch Mistakes Spark Honest Dialogue
Brand Strategy as a Love Letter
I once wrote a newsletter comparing brand strategy to writing a love letter during school lunch break.
It wasn't a framework. It wasn't a playbook. It was a story about sitting under a stairwell with a pen, panic, and no idea how to say what you actually feel. That letter became a metaphor for brand clarity. Messy, personal, honest. The response? People didn't skim it. They shared it. They replied with their own "awkward letter" memories. And more than a few said, "This explained strategy better than any course I've taken."
Over time, that tone — dry humor, clarity, no jargon — became the signature. Clients still forget my name. But they remember the vibe. Most of them now refer to me as "the professor." Not because of a title I gave myself, but because the content makes them feel like they're learning something real, without being talked down to.
The lesson? People remember how you make them feel. Add honesty, a little irreverence, and a clear voice, and suddenly you don't need to keep introducing yourself. The brand does it for you.
Rubber Chicken Leadership
One of my favorite ways I've made my executive brand more memorable was by showing up to a leadership summit not with a slide deck—but with a rubber chicken and a story.
I opened my keynote by tossing the rubber chicken into the audience and saying, "If you catch this, congratulations—you're now in charge of morale." It got a big laugh, but more importantly, it set the tone: this wasn't going to be another dry leadership talk. I wove in humor, personal stories, and interactive exercises that had people on their feet and laughing while learning.
The reaction? The audience said it was one of the most engaging sessions they'd attended. Several executives reached out afterward, not only remembering the message but quoting the jokes and metaphors days later. It proved to me that when people laugh, they listen—and when they listen, they remember. That's the power of leading with humor.
Another time, I introduced myself to a group of CEOs not with my resume—but with a "comedic resume" projected on screen. It listed my "skills" like:
Fluent in Sarcasm
20+ years of surviving awkward Zoom calls
Expert in turning tense boardrooms into comedy clubs (with consent, of course)
It was unexpected, lighthearted, and got the whole room laughing in the first minute. But it also served a strategic purpose: to position humor as a leadership tool, not just entertainment. By the end of the talk, executives were brainstorming how they could bring more levity into their company culture.
The feedback? "Most memorable presentation of the quarter" and, my personal favorite, "I haven't laughed and learned that much since college." Humor doesn't just break the ice—it builds bridges.
Coffee and Resilience
I once shared a behind-the-scenes post about a pitch that completely fell apart. I included a few self-aware jokes and a photo of my coffee looking more prepared than I was. The post was simple and honest, but the humor made it relatable. The reaction was stronger than expected—people shared their own stories, and the post ended up starting real conversations about resilience and presence. That moment reminded me that showing up as a person, not just a title, is what makes a brand stick.
Humor Humanizes Executive Presentations
Early in my journey building my executive brand, I realized that while professionalism is essential, connecting on a human level often requires a touch of creativity and even humor. One example that stands out was during a keynote presentation I gave at a tech conference. Instead of launching straight into data and strategy slides, I opened with a lighthearted story about my early days as an entrepreneur — highlighting a few funny missteps that many in the room could relate to.
I used humor not to distract but to break the ice and make the audience feel more comfortable. It helped create a relaxed atmosphere, encouraging engagement and making the content that followed more approachable. I also incorporated some playful visuals that juxtaposed the challenges of startups with exaggerated "disaster" scenarios, which sparked genuine laughter.
The reaction was overwhelmingly positive. People told me afterward that the humor made me relatable and memorable, not just another executive delivering a generic speech. It helped build trust because I was showing authenticity — that I don't take myself too seriously but am deeply committed to the work.
From that experience, I learned that weaving humor thoughtfully into your personal brand can be a powerful tool. It humanizes leadership and fosters connection, which is crucial when you want your message to resonate beyond just facts and figures. It's about striking the right balance between being professional and approachable, making your brand not only memorable but also genuinely engaging.
Tech Jargon Jokes Break the Ice
One example where I used humor to make my executive brand more memorable was during a keynote speech at a recent industry conference. I started with a lighthearted story about my early days struggling with tech jargon—joking that I once thought "cloud computing" meant literally storing data in the sky! This broke the ice and made me relatable, which helped me connect with the audience. The reaction was overwhelmingly positive; people told me afterward that the humor made the talk more engaging and approachable. It also made my message stick because it wasn't just another dry presentation. Since then, I've incorporated this playful tone into my social media and newsletters, which has helped build a stronger, more authentic connection with my audience while keeping my brand professional yet approachable.
Investor Pitch Mistakes Spark Honest Dialogue
I once added a slide in the middle of a serious investor pitch workshop titled "How to Lose a Million in 10 Days"—a cheeky nod to all the classic pitch deck mistakes we've seen over the years at Spectup. It was unexpected, broke the tension, and gave the room a much-needed laugh. The slide walked through bad financial projections, buzzword overload, and one startup that proudly claimed "no competitors." That last one always gets a chuckle. What surprised me was how it not only entertained but opened up a more honest conversation—founders started admitting their blind spots without feeling judged.
Humor, when timed well, strips away the posturing that often shows up in high-stakes environments. It made me more relatable, not just "the guy in the suit leading the session." One founder even followed up later saying, "You made us laugh, but I also rewrote half my deck afterward." That's the sweet spot—getting people to open up, reflect, and improve without it feeling like a lecture. In the end, it's not about being funny for the sake of it. It's about being human in a room full of ambition and pressure.
