Sell Me This Pen: The Fatal Flaw Rookie Sales People Make

The SaaS Growth Pyramid

The “Sell me this pen” exercise has become one of the most iconic sales challenges in popular culture — popularized by The Wolf of Wall Street when Jordan Belfort uses it to test a salesperson’s ability to create demand out of thin air.

But the exercise itself predates Hollywood. It’s long been used by sales managers and recruiters as a quick, revealing way to gauge a person’s understanding of persuasion, human behaviour, and value creation.

The goal isn’t really to sell the pen — it’s to see how well someone can uncover a need, build curiosity, and position a simple product as the perfect solution to that need.

In short, it’s a test of mindset, not memorization — and it says more about how you think than what you say.

Avoid this common trap with "Sell me this pen"

The trap most sales people fall into with the, “Sell me this pen” exercise is that they focus on the pen.

They usually go into all the features and benefits of the pen.

“Well, let’s see here…uh, it’s a blue pen, it has a clicker, a soft comfortable grip, it writes smoothly… Would you like to buy it?”

Some may try to build in scarcity or tell a story about the pen.

“Ah, this pen isn’t for sale. It’s my own personal pen I bought on a trip to Japan. A very famous pen maker sold out of his last box. He can barely keep up with demand. I begged and I pleaded and he agreed to sell me the one in the display. So yeah, good luck finding this pen anywhere…. But you know what… as much as I love it, I don’t really use it. I mean, I suppose I could let it go for the right person who I know will cherish it and take pride in its ownership as much as I do. So, if you’d like to make me an offer, maybe I’ll consider selling it to you.”

These tactics may work on some people some of the time.

Shifting your mindset

A much better way is to shift your mindset.

You shouldn’t sell something to someone who doesn’t want or need a pen.

Sales shouldn’t be thought of as this competition you vs them where you need to trick, manipulate, swindle your way into their wallet at all costs.

Instead, you determine if they are in need of a pen. How? By talking to them. Building a rapport. Understanding their wants, needs, and values.

And only recommend the pen if it truly fits their wants or needs.

Ask questions such as:

“How often do you use a pen?”

“If so, which ones do you use?”

“What do you like about those pens?”

“What do you like least about pens you’ve tried in the past?”

“Are you looking for a new pen?”

This is sales, helping people make informed choices. It’s unlikely that you are going to create demand out of thin air based on how smoothly you speak, or overcome objections.