"Sell Me This Pen" | BEST ANSWER (from former CEO)

How to Answer ‘Sell Me This Pen’ Like a Pro.
The Secret Method to Master the ‘Sell Me This Pen’ Interview Question.

The “Sell me this pen” question - it’s one of the most infamous sales interview challenges. It’s been popularized by movies like The Wolf of Wall Street and continues to be a go-to question for entry-level sales interviews. But what’s the real purpose behind this question? Is it a genuine test of your sales skills - or is it just a gimmick? While most people might throw out a generic answer about the pen’s features, the key to success lies in how you approach the situation. It’s not about the pen itself - it’s about how you engage with the person in front of you. The real test is whether you can ask the right questions and understand what the other person truly needs. This is where salesmanship shines. The answer isn’t about selling the pen - it’s about selling yourself as someone who can identify pain points and offer a solution. This question is typically reserved for entry-level sales positions, and experienced salespeople rarely face it. The expectation is that seasoned professionals will rely on their track record and not a scripted answer to a one-size-fits-all question. But even if you're not a seasoned pro, knowing how to approach these types of questions can make a huge difference in your performance. Whether you're prepping for a sales role or just curious about the tricks behind popular interview questions, understanding how to approach the "Sell me this pen" challenge is a valuable skill. It’s not about the product - it’s about the conversation and your ability to read the room.


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There is a big difference between what you learn in business school, and what you need to know in the real world – just ask any startup founder or business owner! My goal is to focus on the real-world aspects of business, giving practical tips and tricks that are not usually covered in school.

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I am a practicing management consultant, former CEO, and entrepreneur. I have led many businesses to success, as well as several startups. Among other things, I have an engineering degree, and a master's degree in finance.

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