Sell me this pen

To get a sense of their sales skills, Jordan Belfort asks an audience in The Wolf of Wall Street the now famous 4 words: “Sell me this pen”. If you take the time to prepare to sell something (you can use the same or a similar strategy for anything you’re asked about) in advance, you’ll be ready to successfully answer the question yourself. Read on for the secret answer to this question.

Sell me this pen

Wolf of Wall Street

“Sell me this pen” is a line that forever will be tied to The Wolf of Wall Street. Anyone who’s seen this film from Martin Scorsese knows the scene. In the last few moments of the film, Jordan Belfort stands onstage before an audience, and asks a room full of salesmen to sell him a pen.

After an expectant hush that fills the room Jordan takes a deep breath. The 1990s penny stock broker, who went to prison on charges of fraud and stock market manipulation for orchestrating a massive pump and dump scheme at his New York firm Stratton Oakmont, considers the audience.

Eventually he steps down, walks forward, picks one person in his seat. Staring eye-to-eye, Belfort pulls an object from his pocket and leans over to make a firm request: “sell me this pen.” The reply that comes back does not please him. So he moves to the next person, trying again.

Watch the movie scene here, if you like:

Your ability to sell

But the truth is, “sell me this pen” is a trick question. If you jump right into following the command, you fail. So how to make sense of this question then?

Let’s first start with stating that the pen is a traditional pick for this interview question. Once you’re able to sell a fictive pen, you will be able to sell any product on the spot. Freelancers and entrepreneurs need to be good in selling and develop their ability to sell. The interviewer’s goal is to find how well you can sell.

Interviewers ask applicants for sales, marketing, and related jobs this question, and other questions about to your ability to sell, because they want to identify whether candidates can sell, and what sales techniques they use.

In addition to showing your ability to sell, your response is an indicator of your ability to think on your feet, which is essential in this role. Your answer also demonstrates your communication skills.

Two mistakes most freelancers or entrepreneurs make

1. Skip features

One of the lessons that I mentioned in the blog How the founder of Starbucks made it a success, without even having a passion for coffee to take from the Starbucks brand, is to stop mentioning the features of your product or service if you want to sell them.

As you can see in the video, the salesmen who came for the seminar on how to sell well, all started to respond in a similar way. After naming that the pen is “amazing”, they start to describe the pen’s finer features. It does not please Belfort, because in business it all comes down to how well the product fits with the person’s needs. If the consumer looking for a pen starts to get convinced sees potential in the pen, he will not have any reason to look elsewhere so he will buy it.

The “Sell me this Pen” brings to the fore three selling styles that are typically used by the standard salesperson – one of which is the most desired.

The first is known as value added selling where a candidate attempts to create interest by highlighting the various features of the product which make it desirable.

“This pen is gold – that positions you as a person of value to your peers.”

“This pen has refillable ink cartridges so you never need to buy a new one.”

“Compared to other pens, this pen is very smooth and comfortable to hold in the hand.”

95% of people who have never had any experience selling will utilize this method. Even those who have received thorough training may succumb to the pressure of an interview and lead with comments along these lines.

The problem with value based selling is that you show zero knowledge of what the buyer feels is important to them and thus are simply shooting in the dark with your assertions of value.

2. Assuming that you know what they want

The next evolution in this method is solution based selling – where a candidate successfully asks me questions about what I look for in a pen, if I have any problems with my current writing apparatus to build the case for this pen to solve my needs.

“What is the most important thing for you when it comes to buying a pen?”

“What color pen are you in the market for?”  

“What were the strengths and weaknesses of the last pen you owned?”

Candidates with an enterprise sales background normally demonstrate a strength in this area, however many of them still hit a roadblock when the questions they ask may lead to a conclusion that they need a product which the seller doesn’t have i.e. a red pen instead of a black one. Furthermore a buyer simply may not be willing to talk about their problems to someone they don’t know. So don’t assume that you know what other person wants.

The best answer I’ve heard

This is why it is important to find reps who demonstrate the third technique – problem creation. Instead of asking open questions, they establish a clear ‘ladder’ for buyers to follow using questions which place the prospect in a mental state where they begin to feel a problem they didn’t realise they had originally.

Ultimately the buyer arrives at a pre-set conclusion which the sales representative has orchestrated. This is a rarity but if found – the rep is simply a one in a million find.Given that a vast majority of the sales community knows this example – I found initially that when I brought it up in interviews it drew a number of cliché or pre-prepared responses. Instead, I came up with the idea to start bringing a pair of sunglasses to my interviews –  which I would place next to my notepad and their resume as they presented at one stage in the interview normally towards the end, I would place my iPhone carefully on the middle of the table and say ‘sell me those sunglasses’ i would get a number of responses most of which were Feature based selling – where the candidate would list of a bunch of exciting features that the sunglasses had Solution based selling – where the candidate would ask me questions about my daily life to see if the product could potentially solve any of these for me i.e. Trouble seeing whilst driving, did I like to go to the beach. After 35 interviews, I had found the unicorn.the candidate sat there in silence and asked no questions. Seeing the iPhone- they simply turned on the flashlight (which can be done without knowing the passcode on the latest versions ) and said “How would you like some sunglasses now.” After 34 people failing before them – they went onto to be the highest performer and my most loyal employee.


The moral of the story is that good sales people often solve problems but the best are able to create and then solve them. I would love to hear about your experience below and if you are hiring – please try this and send me your feedback! 

You can find Jordan Belfort’s answer to the Sell me this pen – challenge in this interview by Grant Robertson if you like.

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