Sell me this pen: How to answer one of the toughest interview questions

“Sell me this pen” has become a common interview question that can fill a candidate with dread. Employers use it to see how you sell under pressure — not whether you know pens.

This guide covers what interviewers want, seven steps to structure your pitch, strong and weak example lines, and a full sample dialogue you can adapt.

In this article:

• What NOT to do when asked to sell a pen
• How to structure the beginning, middle, and end of your response
• Examples of great answers to “sell me this pen”

See the classic scene from The Wolf of Wall Street: Sell me this pen (YouTube).

In job interviews, hiring managers sometimes hand you a writing instrument and say, “Sell me this pen.” If you are targeting a sales role, prepare for this question — your response can be a game winner or a deal-breaker.

How to respond to “sell me this pen”

If an interviewer can get a good sense of your personality and motivation from a single question, why wouldn't they ask it? “Sell me this pen” is not as much of a brain-bender as it seems. Follow the tips below to show the employer what you are made of.

1. Do not decline to answer.

You may find the question objectionable, as you are probably not a pen salesman. You might be tempted to say, “I don't sell pens, I sell real estate,” or pass entirely. Neither works. Interviewers ask this for a reason — they want to see if you are comfortable pitching and whether you focus on the product or the buyer.

2. Act like you love this question.

You may dread it, but enthusiasm wins points. If you are in sales, your eyes should light up at the prospect of doing what you are good at. Looking blindsided — deep breath, running hands through hair — signals discomfort. Launch happily and confidently into your response.

3. Ask questions about the client's needs.

Jordan Belfort, the inspiration for The Wolf of Wall Street, answered this on camera when Piers Morgan asked him to sell a pen. Watch: Jordan Belfort sells a pen (YouTube).

Belfort's approach: “How long have you been in the market for a pen? … And what type of pen do you typically use?” When you sell something, ask questions first to find out what their needs are.

The biggest mistake is leading with features: “This is the best pen in the world, it writes upside down” — you sound like a moron. Do not jam a pen down someone's throat. Focus on the customer's needs, not yours.

4. Remember to pivot from questions to statements.

At some point you have to sell the pen. Once you understand the client's needs, transition to statements about the product — sleek design, refillable cartridges, lightweight feel, smooth ink flow. Do not lead with specs; be ready to describe them after discovery.

5. Offer the client something for free.

It can seem counterintuitive, but free trials work — Baskin Robbins gives away samples for a reason. Toward the end of your pitch, offer the pen for a week with no obligation. Come back and see if it met their needs; if not, bring alternatives. Try it before you buy it.

6. Be prepared for refusals.

Your interviewer may say, “I don't need a pen,” or “I can't afford pens like that.” Handling objections is core sales work. Sometimes people want something without knowing they need it; sometimes price clarity changes the picture. If they still refuse, accept no gracefully — and ask whether they know colleagues who might be interested.

7. If possible, close the sale.

If your pitch went well, do not forget to close. Say, “Can I go ahead and write up a bill of sale?” Or offer a bundle: “These pens also make excellent gifts — could I offer you a few for your executive staff?”

Good ‘Sell me this pen’ responses

Examples of strong opening questions and lines:

• “How often do you use pens? When's the last time you used one? Don't you use a pen pretty much every day?”
• “Do you prefer blue ink, black ink? Or maybe even green or red?”
• “Have you ever noticed that a cheap pen isn't as easy to use — the ink doesn't flow, the writing looks worse, and you never know when they'll run out?”
• “Have you ever used a really nice pen — attractive, right heft, ink that flows easily and looks good on the page?”
• “Have you ever noticed that CEOs and executives tend to have really nice pens?”
• “Have you ever needed to write something and didn't like any of the pens you had?”

Bad ‘Sell me this pen’ responses

Answers to avoid:

• “I don't sell pens. I'd rather not participate in this exercise.”
• “This is the most beautiful, functional pen ever, with its lovely design and ground-breaking features.” (Feature dump with no discovery.)
• “If you use a cheap Bic pen, you look like a loser. But you'll look like a big shot if you use this pen.” (Insulting the buyer.)

A sample ‘Sell me this pen’ interview

Interviewer: Sell me this pen.

You: What are you looking for in a pen?

Interviewer: I don't know, I've got a few.

You: Do you love your pens? Do you have that one go-to pen for important occasions because you know it writes well and looks great?

Interviewer: Not really. Sometimes I carry a couple in case the first one stops writing.

You: What do you use a pen for? Notes in meetings? Signing documents or cards?

Interviewer: I've done all the above.

You: And if you use a pen in front of others, do the optics matter? Would you prefer the kind of pen used by well-to-do people, or will any old pen do?

Interviewer: A nice-looking pen is good to have. But it has to work.

You: Perfect. Nice pens not only look good — they write great. This one has gold plating on sterling silver, it's not heavy, and it writes like a dream. Take it, sign your name on any paper. I guarantee the ink will flow.

Interviewer: Yeah, it writes pretty nice.

You: And it's not “expensive” — it's “valuable.” Refillable cartridges mean you never run out of ink.

Interviewer: I usually sleep on it before buying.

You: Keep the pen a week, use it every day. I'll come back next Tuesday — if you don't like it, I'll take it away. If you do, we can talk options. It's yours to use for free, no obligation.

Interviewer: Sounds like an offer I can't refuse.

Best of luck crafting your own responses. As a salesperson, your greatest asset is the force of your personality — be different, be interesting, be prepared. And above all, sell that pen!