June 2, 2015

Even in multi-step hiring processes, the in-person interview tends to be the largest contributing factor to a sales manager’s hiring decision.

leonardo dicaprio wolf of wall street sell me this pen scene

Some personality traits can be easier to identify in face-to-face interactions than over the phone or through a resume.

It is vital that managers make the most of their time with each candidate by planning interview questions for salespeople carefully and understanding what to look for in each candidate’s response.


The Famous Sales Interview Question: Can You Sell Me This Pen?

The question “Can you sell me this pen?” is probably the most well-known (okay, maybe the only) sales interview question in pop culture, thanks in large part to the popular movie, The Wolf of Wall Street.

In the movie the main character, Jordan Belfort, asks his recruits to demonstrate their skills as salespeople by convincing him he needs to buy the run-of-the-mill pen from his own pocket.

His cleverest friend asks for the pen and then tells Jordan to write his name, which he cannot do without his pen. Jordan’s recruit successfully demonstrates the sales tactic of creating a sense of urgency and need for the product with his response and earns himself a figurative pat on the back.

While the scene was effective in the movie, experienced salespeople will disagree that a sense of urgency and need for the product are not all it takes to sell effectively. The question, however, is worth a closer look.


If everyone knows the question, why would we bother asking? sales-sell-me-this-pen-interview-question

The popularity of the “sell me this pen” question can certainly work against us. At this point the question is so well known that even inexperienced candidates might expect it and be able to rehearse a decent response.

Ideally, the question would give us the opportunity to see how well a candidate thinks on his or her feet, but that may not be the case if it is anticipated. While the element of surprise is not on our side with this question, we can still learn a few things about a candidate’s potential from his response.


What can we learn?

  1. Is the candidate prepared? We might not be able to tell if a candidate is speaking off-the-cuff or using a rehearsed sales pitch, but we should at least be able to tell if he is prepared to answer the question. If the candidate completely falls flat, we have a pretty clear sign that he did not bother to prepare or cannot think on his feet and probably will not be a good fit.
  2. Is he willing to perform on demand? A good salesperson needs to do what it takes to make sales consistently. If he is not willing to enthusiastically sell on demand in an interview, when a job is at stake, he will likely not be willing to go the extra mile to keep his numbers up during the slow season.
  3. How does he think on his feet? The very best responses to the “sell me this pen” question will not sound rehearsed and will involve spontaneous dialogue with the interviewer that should inform the candidate’s sales approach. His response to your unique input will give you some idea of his ability to think on his feet and sell creatively to a client’s needs.
  4. Can he communicate clearly?  Clear, concise communication is essential for any good salesperson. Good sales candidates will be able to speak with authority, be friendly and engaging and will also be able to establish rapport with anyone. Persuasion is an advanced form of communication that demands clarity and precision of language. A candidate that can speak well while answering interview questions and then turn around and take the lead in a mock sales pitch will have a much easier time communicating effectively during negotiations with clients.
  5. Does he realize that it is not about the pen?  The most highly evolved salespeople understand that selling is never about the thing being sold; it is about the person he is selling to. If the candidate asks questions to get to know the interviewer during his sales pitch, establishes commonality and tailors his reply to appeal to the needs of the person he is selling to, we can assume he understand what sales is really about.


So he sold you the pen, should you hire him now?

sales manager asking sell me this pen wolf of wall street questionNot so fast.

Asking a candidate to sell something in the interview can tell you that he has put some work in to becoming a good salesperson, that he has done research and that he can perform on demand and communicate well and think on his feet, but all these things can potentially be learned.

Anyone can learn the principles of successful sales, but people with the potential to maintain long, successful careers in sales are born, not made.

Key personality traits required for long-term sales success like Optimism and Drive cannot be taught and are hard to spot in a quick interview.

A clever candidate could push through a few months in the fast-paced and deadline-driven sales world, even if he is not suited to the work, but in time the constant pressure will make him miserable and cost you money.

This is why it is so important to test potential hires for the unique set of traits that are required for lasting, lucrative careers and high-performing sales teams. Combining aptitude testing and strategic interview questions within the candidate screening process will give you the best chance of hiring salespeople that will be successful for the long haul.


So should we ask candidates to sell us a pen in the interview?

The choice is up to you. Like a mock sales presentation, a candidate’s response to the question can uncover valuable information about his knowledge, willingness to sell and ability to communicate.

Watching a potential hire sell, even if his approach is semi-rehearsed, will give you a better feel for his communication style and sales knowledge than all the bullet points on his gleaming résumé.

This question, in conjunction with a few other well-planned interview questions and test-driven data points can ultimately help you build the consistently high-performing sales teams all businesses need.

For more great interview questions for salespeople, check out our posts on the benefits of using the “Fly on the Wall” interview question and the best question to ask to determine if your candidate is a good listener.


Have you ever asked a potential candidate to sell you a pen? How did it go? Share your experience with us in the comments section below!