‘If I’m the smartest guy in the room, I’m in the wrong room.”

Seasoned professionals know that being surrounded by smarter, more experienced people breeds excellence, growth and humility. But back in the day, as a young, ambitious sales rep, this concept was foreign to me. I learned the hard way that trying to sound like the smartest person in the room can, indeed, make you the dumbest.

Here’s how it went down…

One of our most loyal client’s contract was up for renewal, so my boss asked me (the inexperienced guy) to handle the relatively routine job of getting their John Hancock on a new contract. Sales skills were unnecessary because the deal was a shoe-in. But I was new and determined to flex my muscles and earn their respect. So after a bit of idle chit chat, we got down to business. As I pulled out the contract, I said,

“There will be no substantive changes to the contract so this shouldn’t take long at all.”

At least, that’s how it sounded in my head. In reality it sounded more like:

“There will be no substa…sub-sta-tive…sub-STAN-tive..uh, no real changes to the contract.”

And there it was. Dead, uncomfortable silence and the radiating heat of my flushed face. Instead of appearing well-spoken and intelligent, I sounded like a third grader sounding out a big word in a spelling bee. We still signed the contract as expected but I came to the following realization: “Substantive” must be the hardest word in the English language to pronounce.

My advice: “Kids, don’t try this at home!”


I’m hardly the first guy to lay a brick by mispronouncing a word or have an unthinkable slip of the tongue. In fact, every sales person reading this is nodding their head (or shaking it), remembering ‘that one time when I said xyz…’.  Sometimes sales reps are simply trying too hard. In years past, selling looked a whole lot different than today. Fast-talking, feature-slinging salesmen didn’t have to be replete with sales skills—just the most knowledgeable person in the room. (And that was easy.) Now, reps must respectfully earn business by genuinely caring about a prospect’s business challenge and presenting a product to solve it. And with the advent of intelligent, solution-based selling comes the opportunity to stutter and stumble yourself right out of a deal. So Keep it Simple Stupid.

But wait, there’s more!

Mispronunciations happen sometimes. What happens ALL the time is misspellings, misuse of words and grammatical errors. Let’s take a look at a few of the most common, cringe-worthy errors:

Mild Offenses

  • Writing ‘Should of’ instead of ‘Should have’ (Or Could of or Would of)
  • Run-on sentences (For the love of Pete, use a comma and connect your thoughts!)
  • Less vs. fewer (Less in quantity, fewer in number. You wouldn’t ask for fewer butter.)

Medium-sized Slips

  • Irregardless (This controversial word should be banned from your vocabulary.)
  • Referring to an employee’s role and spelling it ‘roll’ (I will roll my eyes at an employee who makes this error.)
  • Loose vs. lose (I would love to think the misuse is a typo, but it’s usually not.)
  • Moral vs. Morale (The moral of this story is that you will lower morale by demonstrating your ignorance.)

Crimes Against Humanity

  • Supposebly (THIS IS NOT A WORD.)
  • Resignate (The word is resonate, folks. You should resign yourself to never to misuse the word resignate.)
  • There vs. Their (Just learn it. Please.)

If one or more of the above doesn’t actually look like a mistake to you, I encourage you to visit www.grammarly.com (thanks to Noah Goldman at People.ai for that link).

Remember, no matter how polished your sales skills, making these grammatical errors can erode your credibility. Is that fair? Should a typo impact your deal? No, it really shouldn’t. And I’m not saying it will. But your prospects are committing revenue to your product/service and errors may indicate a lack of attention to detail or that you rushed through your communication because their account isn’t that important. It can impact their decision—even if they don’t realize it.