Sales Insider Tips: How to Respond to “Sell Me This Pen”

Sujan Patel is the founder of Mailshake, a sales engagement software used by 38,000 sales and marketing professionals. He has over 15 years of marketing experience and has led the digital marketing strategy for companies like Salesforce, Mint, Intuit and many other Fortune 500 caliber companies.
  • August 13, 2021

Remember the scene from the movie The Wolf of Wall Street, where Leonardo DiCaprio who plays the part of a former stockbroker, Jordan Belfort, challenges a room full of salespeople to sell him a pen.

He wasn’t pleased with the answers that were given.

Let’s face it, Sell Me This Pen is no doubt a trick question. If you dive straight into it and attempt to answer without giving it much thought, you’re sure to fail.

Two of the common mistakes that candidates make while answering are:

  • Having preconceived notions about what someone looks for in a pen
  • Focusing only on the features of the pen

You may wonder why this is wrong. Well, jumping right into selling is a lot like throwing darts in the dark without turning the lights on to see the board.

Your instinct may be to go all out about the features because that’s something that you and the person sitting across the table can see. Hold your horses! That’s not how it works.

The thing is, it’s never really about the features. We all value them differently.

What gets a person hooked on a product is the benefit that they can derive from it. That’s your selling point and what you should focus on.

The only way you can ace the Sell Me This Pen test is to get to know your buyer (interviewer) and understand their needs before making the sales pitch.

We will go a little deeper and find out how to answer Sell Me This Pen.

After all, nailing it might just land you the job you have been waiting for.

But before that, let’s take a quick look at why Sell Me This Pen is a challenge that most sales professionals, across different industries, love to present.

Why do interviewers tell sales reps “Sell Me This Pen”

As you probably would have guessed by now, sales leaders include this challenge in their interview process to weed out the can-dos from the can-nots.

The whole idea here is to check whether you can sell and if so, what tactics you would employ.

Through this test, the interviewer will get to know if you can:

  • Gauge your clients’ needs
  • Strike an emotional chord with clients as you speak to them
  • Think on your feet and perform under high pressure
  • Respond clearly
  • Communicate confidently
  • Be genuine
  • Eventually, close the deal

In any kind of sales role, you will occasionally face sticky situations. So prospective employers don’t expect a flawless response from you.

They simply want to understand if and how you stand your ground under pressure. As per the stats, interviews could last a good 45 minutes to 1 hour, so don’t sweat it take your time to tackle it.

How to answer Sell Me This Pen

There are typically 3 standard responses  each of which portrays one of the 3 selling styles that most salespeople adopt:

a) Value-Added Selling

In this approach, you create interest by focusing on the features of a product. You may say something on these lines:

This pen is gold-plated, which positions you (the buyer) as a person of value to your peers.

This pen has refillable ink cartridges, so it will last you a lifetime.

When compared with other pens, this pen is smooth and comfortable to write with.

A lot of people without selling experience will take this route. The issue with this approach is that you show zero knowledge of your customer’s needs.

b) Solution-Based Selling

If you take this approach, you need to ask a couple of questions to understand what the interviewer is looking for in a pen. With the information, you gather, arrive at how the pen in question is the most ideal one for them.

Let’s now dive into some of the questions you can ask:

What’s most important in a pen: Style or Function?

Do you base your purchase decision on cost?

How often do you need a new pen?

This is a better approach than the value-added one, however, you may hit a roadblock if the customer needs a solution which you are unable to provide.

c) Problem-Creation Based Selling

This is by far the best way to sell a product. Move away from asking open questions, instead establish a clear path for buyers to take.

Identify a problem for your customer and position the offer as the solution.

In the process, you will help the buyer realize a problem that they didn’t even know existed a problem that only this pen can solve.

For example, you could ask:

When you get married, how would you like the thank you cards to look when you sign on them?


If you were delivering a presentation to your board, how would you want your ‘pointer’ to represent you?

This approach is believed to be the most impactful. Any salesperson who takes this route is sure to impress hiring managers.

Examples of the best answers

Now that we have discussed the ways you can address Sell Me This Pen, we’re sharing some examples that will help you hit it out of the park and make that winning sale! Let’s take a look, shall we?

Example 1

I would like to understand how this pen might help you, so please let me know how you use a pen during your daily routine.

  • What makes you rely most on a pen, during your day?
  • Tell me about the last time you picked up a pen to write?
  • What was good about it?
  • What seemed lacking or frustrating?

Why this works

With this approach, you are asking questions that will help you understand the buyer’s needs. This shows that you realize that part of being a good salesman is understanding customer needs and having great listening skills.

Example 2

I would love to provide you with the highest quality pens. I will work hard to justify the confidence that you place in me and I will ensure that you are completely satisfied with the product. Can we now proceed with your first order?

Why this works

Eventually, an interviewer is looking to hire a person who can close the deal. In this example, the candidate is making a strong attempt to close a sale!

Be confident, that’s a quality that interviewers seek in candidates who apply for sales roles.

3 tips to help you craft an impactful answer:

Do your best

Take it seriously, as if it were a real-life situation, and use all those tactics that you would employ, in your response.

Don’t give up

The interviewer may not be receptive to all your questions. Be persistent, keep trying till you crack the deal.

Don’t forget to close the deal

Try to land the deal, don’t hold yourself back go all out to persuade your buyer!

You’ve got this

So the next time you are on the lookout for a sales position, be prepared to respond to some variation of the Sell Me This Pen challenge in your interview.

Take a deep breath, calm your nerves and trump them with a response that will not only make the employer want to buy that pen but also land you the job.

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