Are We Surprised that People Don’t Want to Go Into Sales?

Why Negative Stereotypes of Salespeople Stop Us Cold (and Stopped Me)

Jim Vassello
The Farce of the Sale
3 min readApr 2, 2018

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Why do so few embrace sales early in their career, and if they do — by force or by choice — why so few thrive.

“Most Millennials, however, are skeptical about the idea of failing upwards,” writes Neil Howe.

“Though their youth implies that they’re in the best position to take risks, Millennials are actually looking for security. They’d rather climb the corporate ladder than freelance indefinitely — and anticipate hurdles rather than stumble through them. Their poorer economic situation means that many simply can’t afford to risk it all on a ‘maybe.’”

In a world that glorifies the “upside of commissions” yet fails to train us to sell, is it really a wonder we don’t raise our hands for a sales job right out of college?

As Howe continued, “They’re also coming of age at a time when failures are more public and permanent than ever; one social media blunder could keep them from getting a job. This cautiousness is reflected in young adults’ actions.”

At the heart of the crisis for the employers seeking salespeople and the young people pondering whether a career in sales might make sense — especially initially — fear of failure smacks us in the face.

Yes, To Sell Is Human, says the book by author Daniel Pink, but that doesn’t mean we know how to do it.

So we’re afraid to try taking a job where our paycheck is dependent on our results.

And that’s why I washed out of sales.

No one bothered to teach me how to sell.

But could we teach people to actually be human and learn how to influence others?

As I’ve written this book, I’ve developed a little hobby of asking people what they think of sales people. And the results were not flattering. I heard things like:

  • sleazy
  • dishonest
  • manipulative
  • I was literally told I had too much integrity to be a mortgage broker — by a real estate agent.
  • Movie stereotypes

The most important one on that list to me was the last one. I love to be liked, and I hate to be disliked. Going into sales felt like I was making a conscious decision to make a career out of being disliked. Why would anyone want that job?

And the problem is those don’t necessarily line up with what today’s younger generation wants:

  • to have an impact
  • freedom (previously mentioned)
  • personally, I wanted to tell the blunt truth all of the time

I fell into the stereotype hook, line, and sinker, which was why I’d initially washed out. As organizations look to debunk those things, it’s critical to send a new message:

  • The best salespeople are trustworthy and build long-term relationships.
  • Sales is the catalyst for building and maintaining a business. No sales, no need for production.
  • Freedom in your work life to be who you are and establish/maintain/build the company’s reputation.
  • Sales is fighting for what you believe in.

And for me, that came when I stopped thinking of myself as a sales person and realized I was just a player in an improv scene where the other party was the person I was “selling to” — but really was just engaging with to find a solution we both loved.

Funny enough, I’m now proud to say I’m a salesperson… I just had to think differently.

Get The 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.