Tommy Boy Sales Pitch: Lessons and Takeaways Sales movies can teach you a thing or two.

We’re on the last leg of 2015 and many sales teams are probably neck-deep in assessment and planning sessions—looking at how revenue and quota targets were met and trying to come up with ideas on how to bridge gaps and improve performance.

Whether you’re a sales executive or an agent looking to improve and develop your selling skills, did you know that there’s a movie that you can use as a starting point in identifying key selling practices that you can apply to amp up your productivity and increase your sales for the next year?

Don’t worry, it’s not one of those cheesy tearjerker movies overflowing with heavy drama interspersed with boring monologues, I’m talking about “Tommy Boy” a comedy flick that will make you laugh your socks off while imparting useful nuggets of sales wisdom that all sales teams can benefit from.

Learning from Tommy Boy

It’s been 20 years since the “Tommy Boy” hit the theatres in 1995 and not many people actually remember it, except for a cult following among college kids and Chris Farley fans who praise the film for its witty dialogue and camp humour. It seems like an unlikely candidate for an inspirational movie, but in between the silliness is actual advice useful in clinching a sale.

The movie revolves around Tommy Boy Callahan, the only son and sole heir of auto parts mogul Thomas Callahan Sr. In contrast to his wildly successful father whose factory employs about half the town, Tommy Boy is an underperforming guy who spent 7 years barely passing his subjects in college. Tommy Boy’s happy-go-lucky ways are tested when his father marries a much younger woman and subsequently suffers a fatal heart attack at the wedding reception.

After his father dies, the bank demands repayment of a loan Thomas Sr took out to finance a new venture of brake pads that were supposed to be the company’s biggest product. As a result, Tommy Boy must sell 500,000 brake pads to prevent the bank from taking over Callahan Auto Parts and selling it to their biggest competitor. In a bid to keep the company afloat and prove himself capable of taking over his father’s place, Tommy Boy teams up with his father’s right-hand man Richard and takes a trip around the Rust Belt trying to sell brake pads to unwilling companies. After a series of misadventures and failed sales pitches, Tommy Boy has an epiphany and finally finds the perfect sales approach that helps him clinch a ton of sales and save the company.

You might be thinking, “I can’t possibly rely on chance and funny-man antics to improve my sales!” But try to look beyond Tommy Boy’s humour and you will find gems of sales practices that can enhance your sales pitches and rev up your revenue, such as

The importance of brand loyalty.

As unorthodox as some of his methods were, it’s obvious from the start that Tommy Boy really believes in the effectiveness and quality of his product. He believes that their brake pads are worth paying good money for.

During a particularly disastrous sales pitch where Tommy Boy sets fire to a potential client’s toy cars, movie goers can really feel Tommy Boy’s passion and belief that their brake pads are so much better than their competitors, to the point that these brake pads can spell the difference between life and death. And of course, his first major sale was marked by the following quote, which really captures Tommy Boy’s firm belief in his product’s superior quality—

“But for now, for your customer’s sake, for your daughter’s sake, ya might wanna think about buying a quality product from me.”

Learn from experience.

During the course of the movie, we can see how Tommy Boy tries to imitate his father’s selling style, with disastrous results. All seems lost, until an encounter with a waitress leads Tommy Boy to adapt and customize his selling style to fit his own personality. We can see how Tommy Boy learned from all of his failures and harnessed this knowledge to become successful.

Have an honest mentor.

More than just a sidekick and a serious foil to Tommy Boy’s antics, Richard also serves as an unwilling mentor who tries to teach Tommy Boy the tricks of the trade. And while initially unimpressed with Tommy Boy’s performance, Richard did everything (even hitting Tommy Boy with a wooden plank) to help Tommy Boy overcome his weaknesses. Richard gave honest feedback (sometimes brutally so), worked hard and really utilized his sales experience and his past contacts to help Tommy Boy succeed.

Train, train, train.

One of the biggest takeaways from this movie would be the need to train your staff, especially those intended for senior management positions. If we analyse the movie, we can see that Tommy Boy’s troubles essentially stemmed from the lack of training that he received from his father.

Forge a personal connection with clients. Tommy Boy manages to convince a surly waitress to serve him chicken wings even after the kitchen has closed by delivering the following lines:

Helen, we’re both in sales. Let me tell you why I suck as a sales man. Let’s say I go into a guy’s office, let’s say he’s even remotely interested in buying something. Well then I get all excited […] I killed it! I killed my sale! And that’s when I blow it. That’s when people like us have gotta forge ahead, Helen. Am I right?”

As you can see, Tommy Boy found common ground with the waitress and used examples that the waitress can easily identify with. This unnerves the waitress but also convinces her of Tommy Boy’s sincerity. In the end, she decides to give Tommy Boy what he wants. This scene marks Tommy Boy’s first successful transaction and his milestone to becoming a great salesman.

Tell it like it is.

Tommy Boy is honest, straightforward and passionate. He doesn’t need to sugarcoat his sales pitch because he firmly believes in the quality of his product. This is a great lesson that all sales professionals can learn from—clients can detect if you’re exaggerating the features and benefits of your product and will resist being sold to. Be sincere because more often than not, the sincerity is what eventually convinces clients to close the deal.

Be humble.

Don’t flaunt your knowledge of the product and its benefits; instead try to adapt your sales pitch into something that the potential client can relate to. Answer the perennial customer question of “What’s in it for me?” This was demonstrated to great effect by Big Tom, who was such a good seller that he could sell “ketchup popsicles to a woman in white gloves.”

Persistence pays off.

Before Tommy Boy and Richard make it big, they had to suffer numerous rejections and failures that would have made any other person quit. But they didn’t, and their persistence paid off in the end. Statistics from the National Sales Executive Association show 2% of sales are made on the 1st contact, 3% of sales are made on the 2nd contact, 5% of sales are made on the 3rd contact, 10% of sales are made on the 4th contact and 80% of sales are made on the 5th-12th contact. All sales professionals should learn to handle rejection gracefully and try and try again until they succeed.


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Dan Sincavage

Dan Sincavage

Dan is a Co-Founder of Tenfold and currently serves as the Chief Strategy Officer. Dan oversees the Tenfold sales organization, manages strategic partner relationships and works with key enterprise accounts to ensure their success with the Tenfold platform.

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