April 3

A Sales Lesson from The Wolf of Wall Street: “Sell me this Pen!”


Academy Award winner Leonardo Di Caprio stars in Scorsese’s excess-packed The Wolf of Wall Street  – joining a long line of films (Wall Street, Boiler Room, Glengarry Glen Ross) that cast the sales profession in it’s most negative light. While millions of honest people make their living in sales, they rarely make movies about them (with the happy exception of The Pursuit of Happyness.) While I can’t get back the three hours I spent sitting through this morally bankrupt film, I can pass on the one kernel of sales wisdom that almost made it worth the price of admission:

Sell me this pen from The Wolf of Wall Street

Let me set the scene:

Leonardo DiCaprio plays convicted stockbroker, Jordan Belfort and early in his career he is trying to turn a group of inexperienced, undisciplined misfits into junk bond salesmen.  In order to show them how sales works, DiCaprio pulls out a pen and going around the room, thrusts it in their faces, one by one, with the instruction to “Sell me this pen.”

As each one takes the pen from him, they fumble through an attempted sales pitch:   “This is the best pen ever made…”
“This may be the last pen you ever have to buy…”
“This is the same pen used by Abraham Lincoln…”(I made that one up)

After each one,  DiCaprio shakes his head and takes the pen back.  Finally one member of his team grabs the pen from him and hands DiCaprio a piece of paper.

“Write your name on this piece of paper,” he tells DiCaprio.

When DiCaprio looks around for something to write with, the future salesman replies:

“Oh, you don’t have a pen anymore. Supply and demand, bro.”

The “Sell me this pen” scene in the Wolf of Wall Street illustrates a fundamental selling point; one that is often rushed past in our enthusiasm to present product features and benefits.  Until a need is recognized, it simply doesn’t matter how great your product or service is.  I would add to that: until that need has a higher priority than your prospect’s other needs, it doesn’t matter either.  A sales presentation or conversation that doesn’t uncover or address an urgent need is usually a waste of time.


So how do you identify a need and create the urgency to act on it? (After all, only in the movies is grabbing something from your prospect and then trying to sell it back to them a viable tactic.)  Lets look at each separately:

1.  Identifying needs

Often the need is not readily apparent to the prospect, or buried under a lot of other wants and needs.  You can probably recognize this in yourself:  Perhaps you have a project that you know you “need” to get done, but it keeps getting put off as you get distracted by life or other things that come up.  Or, you’ve been living with your “work-around” solution so long that you start to convince yourself you don’t need to fix it, upgrade it or change it altogether. People can lose sight of their needs when overwhelmed with too many responsibilities and decisions. This is where salespeople can serve an important role.

We are in a unique position to help our customers step back and take a more objective view of their needs through a discovery session or needs analysis.  This is the basis of consultative selling, to ask probing questions that reveal pain and discover underlying buyer motivation.  These are things you can find out when you do a good discovery.  

But what if a need is not obvious or a product is new – as is the case with much of technology?  We have to establish the need and a buyer’s desire to change by highlighting the discrepancy between what they currently have – and what they can potentially have by delivering a compelling value proposition.

2. Creating Urgency

Keep in mind that I am not referring to the manufactured “This is the last one in stock!” or “I have another buyer waiting” type of urgency.  Although occasionally true, people can smell false pressure tactics a mile away.  The seller who screams “fire sale!” too often is taken as seriously as the boy who cries “wolf!”  I am talking about authentic urgency:  addressing needs that have been pushed aside or given a lower priority than perhaps they deserve.

As product or service experts, we have a responsibility to raise the potential consequences of indecision or making a poorly informed decision to our clients.  Everyone has experienced wanting something, sitting on the fence too long and regretting it.   As a salesperson, you have the power to help someone avoid this painful experience.

3. Raising the Stakes 

Have you ever seen a movie where the character’s needs are not of the utmost urgency?  Probably not as they don’t get made.  A film about a character who is not convinced he needs to solve his or her problem immediately (or at least in the next two hours) is a film that goes nowhere.  A prospect who is not convinced that he has to solve his problem quickly, is a sale that goes nowhere.

You can help a client reconnect with his needs and the urgency to act upon them by using a simple but effective technique from the movies called Raising the Stakes.  By making a series of associations you can help re-prioritize a decision and bring to light the consequences of either indecision or a poor decision.  

In your next sales conversation, hopefully you will catch yourself if you get the cart (product) before the horse (need).

BONUS TIP:  Check out another great tip from Wolf of Wall Street for virtual selling!

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Imagine a virtual meeting that feels as if you’re sitting across from someone having a cup of coffee. Impossible? Not anymore!

In Look Me In the Eye, you’ll discover how actors, reporters, and other on-screen pros form personal connections with people through the screen – and how you can apply their secrets to build stronger relationships in business that drive sales!

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*Sales and Selling Presentations


Creating urgency

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    1. Karl, Thanks for your comments. And yes, I did see the film. I think I noted that I was riffing a bit on how they tried to sell him the pen, but I did double check the punch line against a copy of the script afterwards to be sure I got that key piece of dialogue correct. Is that not how you recall the scene? Perhaps my set up was not as clear as in the film. One of the many reasons I’m not a screenwriter I guess 🙂

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