‘Sell me this pen:’ The real answer to The Wolf of Wall Street’s challenge

“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. And if you do that, people don’t know what to do. Next thing, he is answering, and now I’m controlling the conversation, finding out exactly what he needs.

“Once I have that, I say, ‘You know, Bill, based on what you’ve just said to me, the pen I have here is the perfect fit. Let me tell you what it’s about…’ Then you can tell them about what you have, because you’re filling a need. 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. It’s like trying to sell someone a house and you don’t know if they’re in the market for a house, what kind of house they want, how many kids – so how can you sell someone a house? That’s the point.”