Human vs Artificial Intelligence: Who Wins at Sales?

Human vs Artificial Intelligence: Who Wins at Sales?

“Sell me this pen.”

That’s the famous quote from Martin Scorsese’s film, “The Wolf of Wall Street,” based on the debaucherous life of Jordan Belfort, a penny stockbroker. Belfort made a huge fortune before he was jailed for his shady business practices. In the film, Leonardo DiCaprio plays Jordan Belfort who challenges his colleagues to sell him a pen. With human vs. Artificial Intelligence, who wins at sales?

Can AI step up to the challenge and do better than humans in selling an everyday object like a pen? While it may not seem like a tough task, it actually takes experienced salesperson years of practice to sell anything to anyone. Who needs another pen anyway? With the advancement of AI and its ever-expanding role in sales, some people think AI can do better than humans in sales.

The jury is still out, so let’s compare AI and humans over 5 critical skills that separate a successful salesperson from the rest of the pact: empathy, listening, agility, critical thinking, and persistence.


Empathy is defined as the “ability to walk a mile in another person’s shoes.” My favorite example is from Barter King, a TV show where people trade stuff without using cash.

In an episode, professional trader, Antonio, is trading a $200 handbag for fishing gear worth $1000. Despite the big price difference, the woman really wants the handbag and has little use for the fishing gear. But she hesitates because of her sentimental attachment to the fishing gear, which belonged to her grandfather who passed away. 

Antonio empathizes with her and tells her that he used to fish with his dad and assures her the fishing gear is going to a good home where it’s going to get used to catching fish instead of collecting dust in her garage. By walking in her shoes, Antonio successfully closes the deal. 

AI emotion detection.
AI emotion detection.

Emotion AI – emotional intelligence – has improved tremendously at detecting human emotions through facial expressions, tone or volume of voice, and so on. Shockingly, AI can tell if a person is a criminal simply by looking at their facial features, with an accuracy of up to 90%. While machines could detect human emotions, they will always be unable to walk a mile in another person’s shoes.

Winner: Human

Active Listening

Great salespeople are like journalists: they actively ask questions to discern what’s on a customer’s mind. 

In another episode of Barter King, Antonio is trading a $100 massage table for a $500 set of golf clubs. The owner of the golf clubs is reluctant to make the trade, again because of the dollar value gap. When Antonio probes her on why she’s looking for a massage table, she explains that she wants to start a home massage business and that the golf clubs belongs to her ex-husband. Antonio discerns her needs and convinces her that the massage table will bring her joy and make her money while the golf club will serve as a reminder of her ex and failed marriage.

Can AI be a better listener? You bet, Crisis Text Line, an AI that uses natural language processing to help people suffering from anxiety or suicidal thoughts, has exchanged more than 83 million text messages to date. What’s surprising is that 86% of those who exchanged text messages reported feeling better afterward despite the fact that they knew that they were not even interacting with another human being! Plus, AI is always there to listen, never zones out, and does not have to sleep, and has millions of data points to know when and how to ask the right question. 

Winner: Machine


Agility is about thinking quickly on your feet and outside the box. In “The Wolf of Wall Street,” when a salesman boasts that he can sell anything, Belfort pulls out a pen and challenges him to sell the pen. He takes the pen and tells Belfort to write his name on a napkin. Belfort can’t because he

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