Inflight Opportunities
You never know who you'll share an armrest with …
A little while back, I shared a flight home with members of my Charlotte based team. As we regrouped in the terminal at Charlotte Douglas Airport, I mentioned a fascinating conversation I’d had with the gentleman sitting beside me.
One of my teammates looked at me and laughed.
“Wait... you talk to people on a plane?”
My longtime business partner and cofounder, Kirk, couldn’t resist the opportunity to land a subtle jab.
“Are you kidding me? You should hear the random conversations this guy finds himself in.”
This specific team is full of lovable shit talkers, so the friendly chirping was both expected and welcomed.
I smiled.
“Absolutely. There are always unique inflight opportunities.”
Many years ago, my father gave me a piece of advice that has stuck with me ever since. If I remember correctly, I believe it originally came from my grandfather.
“Always dress sharp on an airplane.”
Naturally, young and naive, I asked why.
“Because you never know who you may share a row with.”
For whatever reason, that simple advice never left me.
Business. Personal. Travel is something I’d struggle to live without.
Spend enough time in airports and on airplanes, and you begin to notice things you never used to.
One of those things is this:
What does my inflight attire say about me?
Or better yet...
What do I need it to say?
For what it’s worth, I refuse to pay for first class. That said, I often find myself sitting there thanks to airline status earned from years of travel.
Less interesting than the extra legroom or warm towel, you may find my coach to first class dress code strategy a little more entertaining.
In first class, I’ll still dress professionally, but I often tone it down. I’ll pair my patchy sleeve of tattoos with a funky pair of sneakers. Oddly enough, that alone is usually enough to spark curiosity.
In coach, it’s almost the opposite.
I may even overdress a little. Not to impress anyone, but because it often creates intrigue and opens the door to conversation.
Both approaches create interest for entirely different reasons, but they often lead to the same outcome: meaningful dialogue.
I never lead the dance.
I’m simply happy to participate.
Here’s how I see it.
You’re sitting beside a complete stranger. They know nothing about you, your company, or your story. They didn’t click on your website. They weren’t referred by a trusted friend. They’re not in your inbox because of some clever AI algorithm.
They simply happened to book Seat 9A.
Every single flight presents a unique puzzle, and I love these rare opportunities.
People often assume it’s about selling. It’s not. These aren’t sales calls. They’re live reps.
And the real exercise is downloading and organizing.
To earn even the smallest amount of trust, you first have to gather information. That usually starts with a simple icebreaker, followed by thoughtful questions and genuine curiosity. You listen more than you speak. You learn about their story, their perspective, and their interests.
Only then have you earned the right to share a little of your own. Even then, there’s a very good chance they aren’t buying. That’s perfectly fine.
The point was never the sale.
The point was the puzzle.
Somewhere around 35,000 feet, everyone becomes briefly accessible.
That’s an opportunity most people never notice.
Every flight is a room you’ll never be invited into again.
You never know who you’ll share an armrest with.
Or what you’ll learn from them.
Brandon Cullen
In search of life’s [im]perfect soundtrack ...