How to Convince Young People to Sell (and Try Sales)

Many of us have at least one friend that will do something outrageous just for the sake of being outrageous.

Jim Vassello
The Farce of the Sale
3 min readMar 26, 2018

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For me, that friend is Bryan.

I remember walking into a bar one night while he was rocking the socks with Chacos, a flannel, and a baseball cap. I found it hilarious, but I also felt slightly embarrassed for him.

I pleaded my case before we left the house, “Dude, we’re single guys in our mid-20s with average jobs. That’s not enough to compensate for your style.”

“I don’t care, man. Let’s just see what happens,” he says.

Four hours, six beers, and a plate of nachos later, Bryan has the bartender’s phone number and casually wins a dance off against a random stranger. What the hell do I know?

My entry-level sales job required I wear a suit and follow a script. This wasn’t uncommon as many of my friends from college were getting into the same types of roles, but I couldn’t help but feel like a fraud. However, this is how things were and that’s what we thought our buyers wanted to see in their salesperson. A suit portrayed confidence and success.

I would have felt more confident in socks and Chacos.

We’re in the midst of a generational shift where the baby boomers are retiring, the millennials are taking over, and the Gen Xers are caught in the middle of it. In sales, the focus needs to be on the buyer, and in the past it seemed the buyers wanted that charismatic, Wolf Of Wall Street-type representative. Well, as Max Altuscher points out in his Quotable article:

  • 27 percent of the world’s population are millennials. The world.
  • 75 percent of the global workforce is expected to be represented by millennials by 2025.
  • 46 percent of B2B buyers are millennials. BUYERS.

There needs to be a shift in how millennials are brought into sales. Companies are absolutely making changes, too, so I’m not throwing older generations under the bus. Many employees can now work from home, have flexible schedules, and even wear jeans on days other than Friday *gasps.* But millennial mindsets revolve around software applications, digital communication, and optimizing their efficiency. Talking to people in person or over the phone is frightening, especially if we have to sell them something.

Even though half of all buyers are millennials, that means the other half aren’t. The key to grooming a millennial salesperson is in training their mindset on human interaction so they can adapt to different personalities without compromising their integrity.

Core skills salespeople need:

  • Ability to communicate and adapt to different personalities
  • To know the product they are selling
  • To know why they are selling that product
  • The mentality to accept rejection

What millennials want:

  • Freedom to be themselves
  • That’s it.

Bryan showed me how to be successful with girls despite a comically awful outfit. He also reminded me that there are plenty more potential buyers just like him. A great salesperson can communicate with the suit and the sandals, young and old.

The optimal sales environment would be structurally unstructured, and that’s what I’m going to talk about in the upcoming posts.

Buy Farce of the Sale today on Amazon.com, a guide to improving your sales mindset through improv techniques and tactics, including our YES AND methodology. Jimmy is available for sales training workshops, or just a guy who doesn’t mind a good laugh, a good beer and an improv game that combines the two.

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Jim Vassello
The Farce of the Sale

Improv enthusiast, neuroscience hobbyist, digital marketer, and proud father of a labrador/shepard/tasmanian devil puppy.