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  • Sell Me This Pen

Sell Me This Pen Answer: I Tested 20 People, Here Are The Results

  • May 5, 2022
  • 20.3K views
  • 6 minute read
  • Jeff Wiener
Sell Me This Pen Answer
Sell Me This Pen Answer
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Last year, I wrote a blog post called Sell Me This Pen. I Tackle the Wolf of Wall Street Sales Riddle. Do You Know the Right Way to Sell the Pen?

As a quick recap, Jordan Belfort, played by Leonardo DiCaprio in the movie The Wolf of Wall Street, asks one of his salespeople to sell him a pen. The ensuing sales pitch is what I am referring to in regards to the Sell Me This Pen answer.

The short movie clip and the simple idea of selling a pen have become somewhat of a talking point in the sales strategy and training circles over the last couple of years. You can watch the scene where they review the Sell Me This Pen answer below. 

As a result of the post that I wrote last year, I’ve since had numerous conversations with entrepreneurs, sales managers, leaders, and people, and as a fun test, I asked them to “sell me this pen,” much as Belfort asked of his salesperson.

I would say I’ve tested this “interview question” on at least 20 different people in the last 15 months, but truthfully, I didn’t keep count. What I do have is the results of an informal survey.

Why Did I Ask People to Sell Me This Pen? 

I asked the question partly for fun and also as a training exercise for some of my clients.

At first, I was curious. 

I had a conversation with my former director of sales about eight months ago. (He’s still in that position, but I sold the company.)

We were speaking about how to train our salespeople. I suggested that he do his own informal test with his sales team and use this as a training opportunity.

I recommended he ask his team to sell him the pen, that he watch his staff and see how they react and answer. Watch how they sell.

Do they go immediately into sell mode? 

Or do they spend time getting to understand who the person is and, frankly, whether the person can even write? Do they even need a pen?

I believe there’s a subtlety to the art of sales that so few salespeople understand. 

If you ask most people to rank, in order of importance, the character traits of what makes for a top salesperson, you’ll get traits like aggressive, manipulative, pushy, a closer, and great presenter.

The problem in The Wolf of Wall Street movie is that he responds as your stereotypical aggressive salesperson. Most people asked to sell the pen immediately jump into sales mode.

They describe a blue pen and blue ink. They describe the features of the pen. They click it a few times. Show how well it writes. And then they try to close the deal. 

That’s NOT how you sell the pen.

Most people sell as you would expect a salesperson to sell. Aggressive, manipulative, and sale-sy.

In actual fact, the best salespeople I’ve seen and worked with over the years are almost the opposite. Traits like coachable, an excellent listener, intelligent, (both emotional and intellectual), and inquisitive are all traits that come to mind.

My Interesting Sales Experience

In my early days in business in the early 2000s, one of my technicians handed in his letter of resignation.

When I asked him what he was going to do, where he was going to work, he suggested that he was going to start his own small competitive shop. He was going to do the sales and installations, all by himself.

He said something that still resonates with me all these years later.

He said selling was easy. Salespeople make all the money and barely do any of the work. He believed that without any sales experience, he would be able to find clients and build his business.

He was back at my doorstep a few years later looking for his job back.

This is another disconnect. Not only is there the perception that successful salespeople are aggressive and pushy but that selling is easy.

Unfortunately, a good salesperson is probably one of the hardest positions to hire for. They are probably one of, if not the most, underappreciated and frankly (I’m somewhat biased here) one of the most important positions in a company.

No sales. No company.

YES, I do realize that customer service, accounting, marketing, and every other division within a company is important. YES, I realize without accounting, you’ll be going out of business. But if you have no sales, you WILL be out of business.

Here Are The Survey Results of This Informal “Sell Me This Pen” Answer

So I was curious. If I asked 20 (or so) people to sell me the pen, what would I get?

Unfortunately, and for the most part, people tried to “sell” me the pen.

Out of the 20 people I asked, 16 just tried to explain the features of the pen. They clicked it. They showed me how good the pen was. It was like a BIC pen, for goodness sakes!

Three people did a better job, but not great.

Only one person did what I believe was a great job of selling me the pen.

He asked me questions. He got to know me. He created a connection and made himself likable. In the end, he barely tried to sell me the pen. Selling the pen was almost an afterthought.

He recognized that I wasn’t buying a pen. I was buying from the person, first, and then the product, second.

Most salespeople don’t understand that.

Very few salespeople try to make themselves likable. Most speak and don’t stop speaking. It’s like a crappy first date where the other person won’t stop telling you how great they are.

Most salespeople like the sound of their own voice. They don’t stop to listen or ask questions. Many believe the sale is about the product, when in fact, the sale is about the person buying the product.

It’s important to ask questions. It’s important to listen. It’s far easier to be interested than interesting.

Unfortunately, most salespeople don’t understand that, and they take on the role of the used car sales rep. 

How Do You Sell the Pen in an Interview?

Sell me this pen, Wolf of Wall Street
Sell me this pen, Wolf of Wall Street

You sell the pen by not selling the pen.

You get to know the customer. Their likes and dislikes. Who they are. What excites them. You listen as they speak, and you ask lots of questions.

Once you’ve gotten to know who the customer is, their likes and dislikes, you can start asking them questions related specifically to the pen itself.

What Are The Questions A Sales Person Should Ask a Customer When Selling the Pen?

  1. What kind of pen do you like to use?
  2. How often do you write with a pen vs pencil?
  3. What is your budget for a pen?
  4. Have you ever bought an expensive pen, or received an expensive pen as a gift? If so, how did that make you feel? And do you still own that pen?
  5. What’s the most important function or feature you want in a pen?
  6. How often does it happen that you need a pen, but, don’t have one handy?
  7. So I was curious—yes, again—at how some of the “seasoned” salespeople I know, all successful and who I respect, would respond if asked to “sell me this pen.”

So I was curious—yes, again—at how some of the “seasoned” salespeople I know, all successful and who I respect, would respond if asked to “sell me this pen.”

Here are their answers:  Sell Me This Pen Interview: 3 Experienced Sales People Provide Their Response

Since posting this post, I now have three articles written on the fun sales question: Sell Me This Pen.  You can read all of them here:  Sell Me This Pen Riddle.

Good luck with your small business and wealth-creating journey.

If you enjoyed this post, you might also enjoy this one:  9 Steps to Build a Sales Team From The Ground Up

You should also consider subscribing to my blog. I publish one article a week on small business and wealth creation.  You can subscribe here.

Also, I published a book during the summer of 2018, “The Kickass Entrepreneur’s Guide to Investing, Three Simple Steps to Create Massive Wealth with Your Business’s Profits.” It was number 1 on Amazon in both the business and non-fiction sections. You can get a free copy here.

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Jeff Wiener

Jeff sold his company to private equity in 2017 and is now semi-retired. Jeff spends time traveling and with his family, writing this blog, managing his real estate portfolio of apartment buildings,  overseeing his investment portfolio, investigating angel investments, coaching other entrepreneurs, and managing his private equity holdings. Jeff is currently on a couple of boards, one for profit, the other not for profit, and now helps entrepreneurs grow their business, profits, and ultimately, create wealth.

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