4 Sales Management Lessons from 'Tommy Boy'

June 13, 2018

Tommy Boy Callahan Auto Parts

We can’t blame you if Tommy Boy isn’t the first place you turn for sales management insight. It’s just a goofy comedy, right?

But maybe it deserves more credit.

The 1995 cult classic is really all about sales. It tells the story of Tommy Callahan (no relation), who takes over the family business, Callahan Auto Parts, after his father suddenly passes away. To save the company, Tommy (played by Chris Farley) must hit the road to sell the new line of brake pads. He is reluctantly joined by Richard (played by David Spade), and while there are plenty of hijinks, the duo also learns a thing or two about sales.

Here we dive into the holy schnikiest of sales management lessons that can be gleaned from Tommy Boy.

Help Team Members Overcome Adversity

Tommy’s struggles begin early in the movie. He not only loses his father, he also now has to save the family business. It’s a job he doesn’t feel equipped for. Even worse, he has to deal with people who don’t believe in him, including Richard.

It doesn’t go well. At least at first. Like so many classic Farley characters, Tommy is spastic and over-the top. His anxiety gets the best of him in his early sales attempts, and he loses multiple sales because he, well, comes off a little crazy.

Throughout the movie, Tommy faces adversity, but he also slowly learns to overcome the challenges and push himself to be better. Some people thrive under adversity. They need it. That’s why coaches love to talk about “all the doubters,” even when hardly anyone has doubts about their undefeated squad.

All salespeople and sales teams are going to struggle at times. It’s how you channel those struggles that determines success.

Failure Can Make You A Better Salesperson

Tommy fails. A lot. The first half of the movie is all about Tommy’s self doubts and struggles as a salesperson. He has no confidence, and he tries too hard to be perfect.

The good thing for Tommy, and salespeople in general, is that failure is a good thing. Nobody is going to succeed every time, and the learnings from all those failures is what facilitates future success.

Hopefully your team’s failures aren’t as aggressive as Tommy’s, but it’s important for sales managers to let their people fail. All the sales training in the world can’t replace the hard beats that result in ingrained lessons.

Let Your Team Members Use Their Natural Gifts to Sell 

Everything eventually clicks for Tommy. With the help of Richard, Tommy discovers he has a gift for connecting with people. He may not always say the right thing, but he knows how to make a personal connection. Basically, he learns to be himself.

That may sound a little corny, but it’s true. Being a great salesperson requires channeling your natural gifts, and sales leaders should help their team incorporate their strengths into their approach. Another consideration is to create more specialized roles that allow each team member to more easily find their groove.

Many people go into sales because, like Tommy, they have a knack for connecting with people, but not everyone goes about it the same way. By clearly explaining the objective(s), and then stepping aside to allow your team members to decide (within reason) how best to succeed, there’s a good chance you’ll be surprised by their ingenuity.

Critics Don’t Always Know Best

Criticism can make you better, but it’s also important to know when to ignore criticism and trust yourself. Not only is Tommy chastized and mocked throughout the movie, Tommy Boy itself was panned by critics.

Both Tommy and the movie overcame the criticism.

Tommy learns about selling as he goes, and by the end he became a confident and successful salesman. And the movie has gone on to become a comedic classic, oft-quoted to this day.

The lesson? Sometimes critics know best, and sometimes you just have to keep your head down and trust your gut.

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