Home 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 doesn’t have a pen! “Exactly, supply and demand my friend,” the salesman says to Belfort.

Still not convinced that humans are better at thinking outside the box? In 2016, Google’s AlphaGo played against the world’s undefeated Go champion, Lee Sedol, in the ancient and enormously complex Chinese game. AlphaGo, an AI system trained through millions of simulations, won the first three games. But in game four, Lee made a transcendent and beautiful move (dubbed as God’s Touch) that was completely outside the box and allowed a human to strike back.

Winner: Human

Critical Thinking 

Sales is becoming more science than art, and the best salespeople leverage data to move the needle. 

While humans can analyze hundreds or thousands of data points, machines can quickly analyze and find patterns through millions of data. Want proof? It’s all around us in our everyday lives. Google Maps calculates the fastest route. Amazon recommends the best products. Netflix suggests the best content. And Babylon, an AI doctor, diagnoses diseases more accurately than human doctors

Winner: Machine


Our human side gifts us to be empathetic, but that also makes us susceptible to the negative effects of rejections. At Birdnest, we work with amazing real estate brokers and have seen even the most persistent ones get dejected after rejections. As a founder, I have tasted the bitterness of rejection from hundreds of investors and it can take an emotional toll.

But machines have the power to reject rejections. They don’t need to bounce back. They don’t need a mental health day. They don’t need a pep talk. They just keep going at it relentlessly without ever giving up or feeling dejected. Email automation tools always follow up with prospects and never takes any email filled with profanity personally. Chatbots are always on, eager to greet and chat no matter how late it is and how rude you are. 

Winner: Machine


So the next time you get the, “Sell me this pen” challenge at that tough job interview, make the interviewer’s jaw drop with this perfect answer instead of fumbling over words trying to sell a pen. According to Jordan Belfort, the perfect answer is to ask a question. Maybe something like this: “So tell me, how long have you been in the market for a pen?”  You can then identify the customer’s needs and what they’re looking for so you can turn it around on them. 

The jury may still be out on whether AI or humans are better at selling, but based on the five critical traits of a successful salesperson, looks like the machine has a slight edge over humans 3:2 in this best of five.

About ReadWrite’s Editorial Process

The ReadWrite Editorial policy involves closely monitoring the tech industry for major developments, new product launches, AI breakthroughs, video game releases and other newsworthy events. Editors assign relevant stories to staff writers or freelance contributors with expertise in each particular topic area. Before publication, articles go through a rigorous round of editing for accuracy, clarity, and to ensure adherence to ReadWrite's style guidelines.

Nick Jiang

Nick is the Cofounder @ShareInvest. Prior to Share, Nick had grown venture-funded startup Shots to over 10M active users. Duke MBA, Princeton Engineering.

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