A powerful lesson I learned from my annoying boss
Call me crazy, but I believe the single best way to learn marketing isn’t to go to college.
It’s not entering your email into some tiny little box, and it’s definitely not devouring marketing books like a college senior cramming for the final they didn’t study for.
The best way to learn marketing is by working on the other side of the same marketing coin. It’s by doing a stint in outside sales — where your marketing message meets the real world.
My Annoying Boss
Before I was a copywriter writing for Fortune 500 companies and eventually launching my own business, I was a young and spry water guy.
No, this wasn’t the kind of job where I ran out as an undersized guy handing bottles to oversized, sweaty guys. This was the kind of job where I sold reverse osmosis water coolers to companies that wanted nothing to do with paying for water.
That kind of water guy.
This was my first time in outside sales. I had never dreamed of being a salesperson, but I also never dreamed of being homeless. Hence, a career was born.
During that time, I had a super annoying, by-the-book boss.
He was the kind of guy who was a master at taking simple things and making them needlessly complicated.
The kind of guy who would text you at 7:40 AM when your day starts at 8.
The kind of guy who’s so stiff he’ll never need to buy an ironing board.
That guy. He was my boss.
And even though he made me eye-roll more times than I’d care to tell my eye doctor, he taught me a lesson I still use to this day: the real meaning of effective messaging.
The Power of Effective Messaging
The biggest benefit of working in outside sales is not learning persuasion. It’s seeing first-hand how people actually respond to your marketing material.
Working in sales, you get hundreds of opportunities to witness how effective your message really is. And with that feedback, you can tweak your message to make it more digestible.
Here’s what I mean…
I had just landed my first big appointment, and my boss o̶f̶f̶e̶r̶e̶d̶ ̶t̶o̶ ̶ informed me he was going to ride along to help me land the sale. You know, the old Batman-and-Robin routine.
We shuffle into the prospect’s office, and that’s when everything went downhill. FAST. Instead of the usual greetings, the pleasantries, and the small talk (the stuff we all hate but do anyway), my boss dove into our presentation like a pearl diver behind on a loan shark deadline.
“Hi — nice to meet you. We have a patented six-step filtration process and a self-cleaning ozonation feature with an ergonomic design…”
You would’ve thought we were pitching to a doughnut factory based on how quickly my prospect’s eyes glazed over. My boss was deep in the weeds and missing all the flowers.
I was panicking. I could see my prospect’s interest was blowing out faster than a candle at an 8-year-old’s birthday party. So I did something you’re never supposed to do to your boss.
I cut him off.
“Hey, sorry to interrupt, but what I really wanted to say is that our cooler gives you cleaner water and self-cleans, so you don’t have to drink moldy water.”
The prospect leaned in.
“Moldy water?” You could see her brain racing, wondering what the hell she’d been drinking.
I took a deep breath and slowed my pace.
“Yeah, moldy water. You’re using those 5-gallon drums. If you don’t clean them, they grow mold.”
My prospect shifted uncomfortably in her seat.
“Really?”
I nodded like a doctor delivering bad news.
“Really. It’s no different than if you left a cup of water out only to find a few days later that it smells bad. Those 5-gallon jugs are basically a big cup of water.”
The prospect pruned her face. I continued.
“Yeah… if you’ve got a second, I can show you.”
The prospect skeptically looked at her water cup and jumped to her feet while my boss eyed me as if I’d just hijacked the Titanic. We snake through the office, past the cube jungle, until we see it. One massive 5-gallon drum with black gold swimming at the bottom. A piece of mold in the intake valve.
I approach the cooler and lean in.
“Look where the neck of the drum meets the cooler. What do you see?”
Tepidly, the prospect leaned in, her eyes widened, and her nose scrunched.
“Oh no… that’s mold.”
“Yep. These coolers grow mold. Like I said, it’s no different from leaving a cup of water sitting out for a couple of weeks until it smells funny. That’s what those jugs do — they just sit. Whoever changes them is actually supposed to clean them.”
The prospect looked disgusted, regret forming deep canyons on her face. That’s when I repeated, “So all we do is have a reverse osmosis cooler that cleans itself. Cleaner water. No mold.”
“Really?” Her eyebrows raised.
“Yeah, and based on all those jugs you’ve got here, it’s probably going to be cheaper. Want to try it? It’s free.”
“Yes!” she said enthusiastically.
And my boss looked at me with an oil-and-water mix of anger and excitement.
That was life on the water force.
The Lesson
From that moment on, I became obsessed with messaging. What can you say that’s so simple it’s impossible not to understand?
Effective communication is built on understanding. This is often missed by marketers. Hell, it’s missed by people in general.
Have you ever seen a LinkedIn post that says, “We help growing companies deploy top-tier solutions to boost profitability and strengthen the bottom line,” and yet you have no idea what the hell the company actually does?
Happens all the time.
What marketers miss is that it’s not about the fancy buzzwords. It’s not about sounding smart. It’s about being understood. It’s about making your message so simple, so straightforward, that it’s impossible to ignore the value.
Take the water coolers. Which sounds easier to grasp?
- “We have a six-stage, patented filtration process that removes chemicals and ozonates to reduce mess.”
- “Cleaner water. Mold-free.”
The second message always wins. Why? Because people read your marketing material, not companies.
People. The same people who are worried about lunch at 10 AM, even more worried about lunch at 12 PM, and juggling life, bills, and their own annoying bosses.
If you understand people, you know they’re busy and distracted. If they don’t comprehend what you’re promoting, they’ll never buy what you’re promoting.
That’s why it’s so important to simplify your message. Keep it simple, stupid. Because we’re all busy with stupid distractions that rob us of the present moment.
Full Circle
After that experience with the water cooler, I went home, reviewed all of our marketing materials, and threw them away. Instead, I created new materials that simply stated: Cleaner water. Mold-free.
Since then, I’ve been fortunate enough to sell to over 200 companies that already had a water service and certainly weren’t excited to see me. That’s the power of a good message.
Years later, I took what I learned from that and landed a direct response copywriting gig with America’s #1 Home Security company — all because I understood the value of a good, clear message.
Today, no matter what I do, I always find a way to make the message as simple as possible.
Marketing is all about understanding people and showing how your product or service fixes a problem in their lives. So, spend some time in outside sales, focus on people, and when you’re done, you’ll understand the power of a good message.
And you’ll truly appreciate the meaning of keep it simple, stupid.
