It’s a phrase made famous by the movie The Wolf of Wall Street, and for good reason. On the surface, it’s just an ordinary question, but anyone in sales knows there’s more beneath it. The moment someone asks you to sell them a pen, they’re not just looking for the features of the pen. They want to see if you understand the art of persuasion, of meeting needs people don’t even realize they have yet. This challenge has been tossed around business schools and sales training programs for years, but it’s not about the pen at all—it’s about how you connect with people and what you can offer them beyond the obvious.
The first mistake most people make when trying to sell the pen is describing it. “It’s smooth,” they might say, “with a sleek design and a comfortable grip.” But this approach misses the point entirely. No one buys a pen for its design alone. You need to shift the focus from the pen itself to the person you’re selling it to. What does the person need? What problem do they have that this pen can solve?
Imagine the person sitting in front of you runs a small business. Ask them how they currently handle signing contracts or writing notes. Get them talking about themselves, because the more they talk, the more they reveal what’s important to them. Then, you can position the pen as the solution to their needs. “This pen,” you might say, “isn’t just a tool for writing. It’s the final step in sealing your next big deal. Imagine the satisfaction of putting your signature on that dotted line, knowing you’re closing another successful transaction.” Suddenly, the pen isn’t just a pen. It’s part of their future success.
But the pen trick goes deeper than that. You’re not just selling a product—you’re selling confidence. The way you present it matters as much as the pen itself. In sales, there’s a golden rule: people buy from those they trust. The key to selling anything, whether it’s a pen or a multi-million dollar product, is to build that trust first. You do this by asking the right questions, actively listening to the answers, and then presenting your product as the perfect solution to the problem they just told you about.
Here’s the thing: selling a pen isn’t about the features or even the pen itself. It’s about understanding what motivates people. Do they need it to feel prepared in a meeting? Is it the missing piece for a contract that could change their career? You have to figure out their “why,” and then tie that back to what you’re offering. The pen isn’t the hero of the story—they are. The pen is just a tool to help them get where they need to go.
So, the next time someone asks you to “sell them this pen,” remember that you’re not selling the pen. You’re selling a solution to a problem, a way for someone to reach their goals. And once you realize that, you can sell just about anything.