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How To Answer Sell Me This Pen

You walk into your first sales job interview, and Leo DiCaprio says to you, “Sell me this pen.”

Yes, it’s a scene from a movie. But I’ve also heard people ask some variation of this question in real sales interviews, and it’s something you should be prepared for.

Why interviewers ask you, “Sell me this pen”

When someone asks you to “sell me this pen” – or to sell any simple, commodity product – they’re really looking for three things:

  1. Do you ask questions or jump to “selling?” Contrary to what most of us think, great sales people are better at listening than talking. Sales starts with understanding what someone needs – what job are they trying to do with that pen or with anything else? So, first, your interviewer is looking for you to ask them questions, not start talking about how great the pen is.
  2. Can you solve someone’s problems or address their needs with the product? Once you understand what they want, your job in sales is to figure out how the pen (or other product) can give them that.
  3. How do you handle objections. No matter how you respond, your interviewer will likely have a reason why they don’t need the pen. They’ll want to see how you react. The wrong response is to try and convince them that they need it (they’re the expert on what they need). The right approach is to focus on what they told you they want and show how the pen can get it for them.
  4. Are you creative? It’s a silly example, but creativity will stand out, and you’ll get bonus points.
  5. Are you personable? Another misconception about sales is that it’s all bullshit and charisma. Likeability is far less important than knowing how to ask the right questions, and how to satisfy customer needs with the product, but if you’re confident, funny and enjoyable to talk with, you get bonus points.

How to answer “Sell me this pen”

In the movie, Leo’s buddy asks Leo to write down his name – creating a need for the pen.

A simple approach, then, is to ask questions to understand what someone cares about that might require a pen, and reveal or create the need for the pen.

Sample questions to ask your interview

  1. Are they single? If so, you could get them to write down their number for an attractive person. If you’re in an informal setting, point someone out and say they’ve been eying you – offer to take over the number if they write it down.
  2. Is the pen special? If it’s a personal pen (or other item), you can ask about the history or significance. Who gave it to them? What was their fondest memory of that person. What does the pen symbolize to them?
  3. How much is the pen worth to them? You can always ask how much it’s worth to them, and then offer to sell it for that price. (After all, they didn’t say to sell the pen for a lot of money.)
  4. Do they avidly support a charity, political party, or cause? If so, you could mention that you’re well connected with that charity and actually going to be seeing them later in the day. Offer to make a matching gift if they write and sign a check now.
  5. Have they recently received a gift, favor, or gone to a party? If so, maybe they need to write a thank-you note.
  6. Do they have dogs or kids? If so, you can ask if they ever need to write down words to their partner (to keep the dogs from getting excited about walks, or kids learning of a surprise).
  7. Do they enjoy reading books and making notes?

Some of these approaches emphasize the pen itself, but most are focused on what the person can do with the pen – writing. Be creative and think of why you might want a pen, and what questions you can ask.

How to respond to objections

Expect them to share reasons why they don’t actually need a pen. In your responses, don’t focus on the pen itself. Keep the focus on how the pen lets them accomplish their goal.

For example, if you offer to take a note to the attractive person across the restaurant, your interviewer could object in many different ways. Your goal is just to keep the focus on how the pen can provide them the relationship (or validation or carnal satisfaction – whatever it is) that they want.

Sample objections and responses

ObjectionPotential response
Look, I’m not really interested in meeting someone.Really? Would you mind sharing why not? Tell me about when you last went on a date.
They’re not really that attractive.OK, well what’s your type? I bet we can find someone who you’re into.
I don’t have time for a relationship right now.Who said anything about a relationship. Did you see the way they were looking at you?
I don’t want you to take the note to them.That makes sense, I bet it’d be much sexier if you took it over. (If you’re the same sex as the person, you could say that you’d find it much sexier if they did.)
Example objections and how to respond to them

Sample answer to “Sell me this pen”

Here’s one way I might respond to, “Sell me this pen” in an interview:

Sure. Before we start, do you mind if I ask a few questions?

Great, one thing I was curious about – do you have any causes you really care about? It could be organizations you support, or political causes?

That’s so interesting. What was it that got you so interested in this cause?

Wow, that’s a huge coincidence. I’m actually raising money for that organization. I was offering to make a matching gift to them and was going to take a check over today as part of my contribution. Would you mind writing a check now?

Oh, you don’t have a pen?

Alternative questions to “Sell me this pen”

There are two main variants of this question you’ll face in a sales interview:

  1. Selling commodities. This could be a pen, smartphone, computer, table – literally anything that is functional and interchangeable with other things.
  2. Selling products. This might be the company’s product, but it could also be something you know well – like Spotify, Amazon Prime, Netflix.

In either case, you can use the same approach: start with questions to understand what benefit the person could get from what you’re selling, or what functional or emotional job that product can do for them.

More resources

By Taylor Thompson

Taylor is a co-founder at Purpose Built Ventures, where he helps launch mission-driven companies. Before Purpose Built, Taylor led growth at Almanac, strategy for Curious Learning, and product at PharmaSecure. His work helps 100,000s of people collaborate at work, 4 million children learn to read, and protects billions of medicines from counterfeiting. He has hired dozens of people, helped raise more than $50 million, and contributed to HBR.org as a researcher with Clay Christensen. Taylor is an Echoing Green Fellow, and he has degrees from Dartmouth College and Harvard Business School.

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