Have you ever seen The Wolf of Wall Street?

If you have, you already have an idea of the premise of this article.

If you haven’t, don’t worry—this is going to be a practical advice article for salespeople, not just a list of movie references. Also, go see the movie. It’s great.

In case you aren’t familiar, The Wolf of Wall Street is a Martin Scorsese film starring Leonardo DiCaprio in the role of Jordan Belfort, who was a well-known real-life fraudster active in the 1990s. Since then, Belfort has written books, given speeches, and otherwise helped people be better salespeople and better professionals.

So what’s with the “sell me this pen” gimmick? And how can it make you a better salesperson?

Sell Me This Pen

This line is a recurring idea in the film.

Early on, Belfort challenges his friends to “sell [him] this pen” at a table in a restaurant. One friend takes the pen and asks Belfort to write down his name. Naturally, Belfort replies that he doesn’t have a pen.

“Exactly,” the man replies, throwing the pen back at him. “Supply and demand.”

It’s a fair point. If someone needs something, they’ll probably buy it.

But there’s a lot more to dissect here.

Later in the film, Belfort gives a seminar and asks the salesmen in attendance to sell him a pen, going through the same exercise. The first person begins describing the pen as something amazing, noting its most important and unique features.

For Belfort, this isn’t good enough. He moves onto the next salesman, who again tries to describe the pen in clear detail. Again, this isn’t good enough.

This loosely implies that it’s not enough to simply describe what you’re selling and hope that it does the job.

Remembering the earlier scene, you might think that the “right” answer is convincing the person they need the pen—calling up something like, “You need a pen, right? Here’s a pen!”

And on the surface, this makes sense. It’s probably more convincing to tell someone they need something than it is to just describe the object in question as flatteringly as possible.

But there’s more to this—and Jordan Belfort himself (as in, the real Jordan Belfort, and not Leonardo DiCaprio) has gone on record about it.

Why Jordan Belfort Rejects the Answers in the Film

To Jordan Belfort, the answers in the film were insufficient.

He had this to say:

“It’s sort of a trick question. Because when you say to a salesman, ‘Sell me this pen,’ you might find some will say to you, ‘This is a great pen, this pen writes upside down. It defies gravity, this pen is the cheapest pen on earth, this pen will never run out.’ They’ll say all the reasons the pen is good, they’ll start telling you the features, and the better ones will give you the benefits too. But that’s not what the real answer is.

“The real answer is, before I’m even going to sell a pen to anybody, I need to know about the person, I want to know what their needs are, what kind of pens do they use, do they use a pen? How often do they use a pen? Do they like to use a pen formally, to sign things, or use it in their everyday life? The first idea is that when you say ‘Sell me this pen,’ I want to hear [the salesman] ask me a question. ‘So tell me, how long have you been in the market for a pen?’ I want them to turn it around on me and start asking me questions to identify my needs, what I’m looking for.”

In other words, the best way to start selling isn’t to start talking, but to get the other person to start talking. If you’re the one doing the pushing, before you know anything about your customer, you’re doing something wrong.

Belfort goes onto say:

“Most average or newbie salespeople think that they’re supposed to sell you the pen, when a really seasoned salesperson will actually turn it into a qualifying session to find out what you need. That’s the truth of it.”

Sales is a kind of matchmaking game. You’ve got a square hole, so you need a square peg to go in it. You can’t just pick up pegs at random and try to make them fit.

Well… I mean, you can, but it’s not going to be very efficient.

This is the approach of “solution selling.”

The Critical Mistakes of the Conventional “Sell Me This Pen” Approach

So let’s break this down. We’ll take a look at the conventional “sell me this pen” approach, which is to highlight the best features of the pen.

What’s wrong with this?

Describing the pen first.

The first mistake is immediately moving to describe the pen. Yes, you’re selling the pen, so it makes sense to describe it. But you shouldn’t be describing it first.

The second you do this, people will feel they’re being sold to. They aren’t stupid, and they’ve dealt with pushy salespeople in the past. Accordingly, they tend to be defensive. Leading with a compelling description is going to put their guard up.

This is also a problem because it doesn’t allow you to forge any kind of relationship with your prospect. There’s no warmup. No bonding. No rapport. Just “hey, buy this pen! It’s amazing!” Definitely not the way you want to start.

Assuming knowledge.

The second mistake here is assuming knowledge. You may think you know the typical pen buyer well, and frame your pitch around that. For example, you may believe the average pen buyer wants a pen that writes upside down and clicks easily, while not running out of ink for years.

Sure. But do you know for sure that these features are most important to the average buyer? Do you even know whether this prospect is an average buyer?

Unless you’ve done all your prospecting and conversing in advance, you shouldn’t be trying to sell the pen so prematurely. You need to do your due diligence and figure out who this person is.

How to Ask The Right Questions

The solution to the “sell me this pen” dilemma, if we can call it that, basically boils down to this: ask sales discovery questions before you start pitching.

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Instead of going directly into your main sales speech, spend some time getting to know your prospect with great questions.

So how can you ask great questions?

That obviously depends on the situation, but you can try to ask questions based on the following:

Current needs.

One of the most straightforward lines of question you can offer is asking your prospect about their current needs. For example, you can ask, “Do you have a pen that you like? What do you like about it? Do you wish it was better in any way?” or “Are you forgetful? Do you ever wish you had more lists to remind you of all the things you have to do? How would you make lists, if you could?”

Personal opinions.

You can also get people talking about their personal opinions. “What do you think of ballpoint pens? Are pens the best way to write things down, or do you prefer pencils?”

Personal history.

Delve into the person’s history, especially as it’s relevant to this item. “When was the last time you bought a pen? When and how did your last pen fail?”

Specific preferences.

Get more details about this person’s preferences. For example, “Do you prefer blue ink or black ink pens? Do you like pens with a cap, or those that you can click?”

Budget and resources.

This is great if you’re selling to a business. Figure out how much this person is willing to spend, or what other limitations they may face. For example, “How much do you usually spend on pens?” or “What do you think is a reasonable price for a pen like this?”

Pain points.

After asking some of the above questions, some salespeople prefer to ask prospects about their pain points. For example, you may ask, “don’t you hate how every ballpoint pen you pick up seems to be out of ink?” or the less biased question, “is it easy for you to find a pen that works when you need one?”

Bigger picture questions.

Most of the previously listed questions are clearly relevant to the pen and the person buying it. But you can also find out more about your prospect by asking questions about the bigger picture. For example, you can ask a prospect about their family life, what type of job they have, and what their long-term goals are. You can ask them about their overall life philosophy, and how they buy other types of items.

You can ask them almost anything, really; as you’ll see, simply making conversation can be a powerful way to lead into a sale, and you’ll learn more about your prospect in the process.

Whatever combination of questions you choose to ask, make sure to incorporate whatever you learn about your prospect into your subsequent attempts to sell.

The Benefits of Asking Questions

Asking questions is the right way to sell someone a pen.

It’s arguably downright vital.

And it’s vital for different reasons, such as these:

Getting to know your customer.

The obvious benefit here is that you get a chance to know your customer. Instead of just assuming why they want or need a pen, you can figure it out yourself and address it.

If the customer isn’t a good fit, you can acknowledge it—and stop wasting your time. If they are a good fit, you’ll understand why they’re a good fit—and you can create a custom pitch to appeal to them.

Building a bond.

This is also a great move because it’s an opportunity to build a bond with your customer. People are much more receptive to persuasion if they feel like they know you and can trust you—and asking questions gives you a platform to build that trust.

Human beings love talking about themselves. Research shows that when we talk about ourselves, we experience the release of “feel good” chemicals in the brain, just like when we’re eating good food, taking drugs, or having sex.

Putting the pen aside for a second and letting your prospect talk about themselves will make them feel good and make them like you more—then, you can use that platform to increase your odds of completing the sale.

Providing a distraction.

Remember, people tend to get defensive if they feel like they’re being sold something—or if they’re being convinced of something. But asking a question could provide a kind of distraction, masking the sale and preventing those defenses from arising.

See, asking questions is a way to hijack the brain, so to speak; it triggers a phenomenon known as instinctive elaboration. After hearing a question, your brain has a hard time thinking of other things—which means your prospect is going to be more focused on answering your question than analyzing your motives or finding ways to refute your claims.

Improving Your Performance

Whether you’re in inside sales or outside sales, these tips will help you give the perfect answer. Unfortunately, you’re probably selling something a tad more complicated than a pen. And you’re probably following a more in-depth approach to sales.

No matter what, you’re interested in improving your performance.

And the best way to do that?


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Accordingly, it’s one of the most important platforms to measure.

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