Why creativity kills sales scalability (and how to fix it)

I’m not gonna lie: I’m a great salesperson. Humbleness aside, I've pretty much always been. But as long as we’re being honest, I’ve got a confession, too: I was a terrible sales manager.

Seriously, I almost ran my first sales team into the ground. And I probably would have, too, if not for a single, defining moment: The moment I met the sales genius who gave average, underwhelming, and all-around unimpressive sales pitches.

If you’re a sales manager or leader of any kind, this is for you: The story of the most valuable sales leadership lesson I ever learned. Hopefully, you won’t need it as badly as I did.

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(Not so) humble beginnings

As I said above, I’ve always been a pretty gifted salesperson. I had my faults and made mistakes, but I usually closed more deals than I lost, and it didn’t take long for my creative pitches and aggressive negotiation tactics to catch the attention of my superiors. Soon, I was promoted from salesperson to sales manager.

And just like that, I was in charge of an entire sales team: A team I had to teach to replicate my results and scale my successes. No big deal, right? Wrong. As it turns out, that’s where my natural gifts ended.

I thought being a good sales leader meant demonstrating my abilities through impressive presentations, so I spent every day wowing my team and winning customers with new and creative pitches.

On one hand, this was great: My presentations really motivated and inspired the team. On the other hand, my salespeople were failing; all of them, every single month. I was failing as a manager.

I knew this was my fault, but I couldn’t figure out why. After all, I spent every day “training” my team, teaching them everything I knew, and demonstrating what I wanted from them. It worked for me, so why wasn’t it working for them?

Meet the sales genius who changed my life

Fast-forward a couple of months and things weren’t any better. But then, mere weeks from a mental breakdown, I got lucky: I was invited to an exclusive sales leadership workshop and that’s where I met the sales manager who would save my career.

The first time we met, I was immediately impressed by his charisma. But what intrigued me most was his reputation: He was supposed to be some sort of sales genius with a massive and highly successful team.

At this point, I was desperate. I had to know this guy’s secret. Thankfully, I’d get my chance: We were both scheduled to deliver practice presentations to the other workshop attendees for feedback.

I was the first to present, so I took the stage and did what I always do: I winged it. With no preparation, I gave a pitch that was customized to the audience, full of funny details pulled from earlier in the event.

And it couldn’t have gone better: I hit all the right notes and had people smiling, laughing, and engaging the whole way through. But as soon as my presentation was over, I was only interested in one thing: Hearing this sales genius deliver his pitch.

Then, finally, he walked on-stage.

The most mediocre sales presentation I’ve ever seen that turned out to be the best sales management lesson I’ve ever received

This so-called sales genius reached into his bag and pulled out an old-school folder full of what looked like laminated PowerPoint slides, then spent his entire presentation going through one slide at a time.

It was … unexpected, to say the least. I don’t know what exactly I was expecting, but it wasn’t that.

Don’t get me wrong: He didn’t give a bad pitch. It had a clear beginning, middle, and end, with a good call-to-action. It was just … boring. Boring, uninspired, and overwhelmingly average. And based on everything I’d heard about the guy, I was more than a little surprised.

So surprised, I may have been a little blunt. When it was time for feedback, I said something like, “Is that really how you give presentations to customers? I’m sure you can do better than that.”