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Sell Me This Pen: Tackling The Wolf Of Wall Street Sales Riddle


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For many, the phrase “Sell me this pen” evokes images of the iconic closing scene in the blockbuster movie “The Wolf of Wall Street.” However, this enigmatic sales riddle has been a staple of interviews in the world of sales and marketing for quite some time. While it may not always be a pen, the underlying challenge remains the same: can you sell a seemingly mundane object in a way that captivates the buyer’s interest and compels them to make a purchase? In this blog, we’ll dissect the “Sell Me This Pen” scenario and explore the right way to tackle it.

The Wrong Approaches: What Not to Do

In “The Wolf of Wall Street,” two characters take a swing at answering the famous question, but they fumble the opportunity. Their fundamental mistake lies in their approach. They focus on listing the pen’s features: “It’s a nice pen,” “It’s shiny,” “It has blue ink.” While these features may indeed make the pen functional, they lack the spark needed to ignite a potential buyer’s interest.

Another pitfall is trying to dictate how the buyer should feel about the pen. Saying, “You will love this pen,” or any variation of that, can be off-putting because people want to arrive at their emotions naturally. You can’t simply tell someone to be happy and expect them to feel that way.

The Right Way to Sell Me This Pen

So, how should you approach the “Sell Me This Pen” question? In “The Wolf of Wall Street,” a pivotal scene gives us a glimpse of the right way to handle it:

Jordan Belfort: Sell me this pen.

Brad: Write me your name on this napkin.

Jordan Belfort: I can’t, I don’t have a pen.

Brad: There you go, it’s a matter of supply and demand.

While this response isn’t perfect (there’s no real reason for Jordan Belfort to write his name on the napkin), it touches on a crucial principle: understanding the buyer’s needs. The real Jordan Belfort, on whom the movie is based, offers a different insight: “I need to know about the person, their needs, and their pen preferences.” He emphasizes the importance of asking questions.

A more interactive approach involves using a check:

You: “How many checks do you write in a month?”

Sales Boss: “At least 30.”

You: “Okay, that’s 30 checks a month, about 360 checks a year. Do you find yourself reaching for the nearest pen you can find?”

Sales Boss: “Yeah.”

You: “Wouldn’t it be great if you had one pen, full of ink, that you could use consistently with each and every check? A pen that’s exclusively yours, for every check, contract, and signature.”

Here, you’re appealing to the buyer’s sense of ownership and showing them the emotional value of having just one reliable pen.

Unconventional Approaches

If you want to stand out, consider unconventional approaches. For instance, if the interviewer hands you the pen, you can humorously respond:

You: “Is this your pen?”

Sales Boss: “Yes.”

You: “Do you want it back?”

Sales Boss: “Yes.”

You: “That will be $3.”

While this approach may not amaze the interviewer, it showcases your ability to recognize opportunities when they arise.

You could also try a more daring approach by putting the pen in your pocket and remaining silent. When prompted, say something like:

Interviewer: “Are you going to try to sell me the pen?”

You: “This pen? This is my favorite pen and the only one I have.”

This response may lead to a unique and engaging conversation.


In the world of sales and marketing, the “Sell Me This Pen” question is a classic test of your selling prowess. The key is to move beyond mere pen descriptions and find a way to make the buyer genuinely feel the need for it, whether through emotional attachment, value, or a clever twist. Like many interview questions, there is no single correct answer, but by discovering an inventive strategy that resonates with the buyer, you’ll leave a lasting impression and increase your chances of landing the job. So, the next time you’re asked to sell a pen, remember to ask questions, understand your audience, and think outside the box. Happy selling!

Alejandro Garcia
Alejandro Garciahttps://twitter.com/Gracia_A141997
Alejandro Garcia, Entrepreneurship Writer at CEO Scoop Magazine. Sharing stories and strategies of innovative business leaders. Inspiring aspiring entrepreneurs with insights into building successful ventures.


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