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4 Tips for Sales Mentors from the Movies

For a veteran salesperson hungry for more opportunities and a shot at a promotion to leadership, becoming a sales mentor might be your meal ticket. But the question is, how do you effectively coach young sales professionals beyond their early stumbling blocks? Which tactics and tips for sales mentors are universal? For our answers, we’re going to go to the movies.

Unfinished Business (2015) – Teach Them Your Mistakes

In most Vince Vaughn movies, there aren’t a lot of lessons to learn. Unfinished Business is different for sales mentors. Vaughn plays a sales manager who needs to close a big deal or go bust. While competing against a large competitor, his sales team’s meeting is inconveniently rescheduled by the client. That’s when a seasoned employee, played by Tom Wilkinson, points out the truth.

He says, “Are you the kind of guy who when his girlfriend is trying to blow him off doesn’t get it and still does her Spanish homework?” Having been around long enough, Wilkinson’s character knows when they’re being strung along and gives Vaughn the sense of urgency to network until the deal happens.

The lesson? Some mistakes you can let your protégés make. Others are too costly to be used as teaching tools. Tom Wilkinson’s character spotted the difference and spoke up. Be sure to give mentees the freedom to make little mistakes while learning, but prevent the costly mistakes that risk ruining their careers. They can learn those lessons indirectly from your own experience.

Wolf of Wall Street (2013) – Give Clear Messages

Most of the lessons from Wolf of Wall Street will land you in jail. However, there is one shining moment in a sea of bad takeaways. Jordan Belfort (played by Leonardo DiCaprio) is tutoring a group of wise guy trainees in a dingy diner, when he roleplays a scenario with his protégé that hits the heart of mentoring’s best stratagem (we’ve cleaned up the scene a bit).

Belfort: “Sell me that pen.”

Brad: “Why don’t you do me a favor? Write your name down on that napkin for me.”

Belfort: “I don’t have a pen.”

Brad: “Exactly. Supply and demand, my friend.”

Belfort: “See what I’m seeing? He’s creating urgency. You get them to want to buy the stock. Give them something that they need.”

The short exchange boils the principle down to its simplest elements, giving his crew something easy to comprehend. Most of your trainees will be less thick-headed than those guys, but the simplest lesson is still always the strongest. Plus, there’s direct benefit for you. By finding a concise and easy way to explain sales principles, comprehension of your craft goes up and sales skills improve.

Glengarry Glen Ross (1992) – Never Forget Empathy

Glengarry Glen Ross is a notorious film among salespeople. Alec Baldwin’s Blake is ego and machismo at its worst. He’s the last person you’d expect as a good example on a list offering tips for sales mentors. And he’s not a good example. He’s terrible, but his rude and ruthless manner make for a good cautionary tale.

When he belittles and threatens the film’s cast of stressed veteran salespeople, what does he achieve? The worst kind of results. Men lie, cheat, and steal to prevent themselves from being tossed out on the street. Leads are stolen and the company’s reputation takes a hit as its salespeople adopt desperate tactics. In the process of trying to light a fire under these guys, Baldwin’s Blake ends up making matters worse.

A good mentor always remembers to treat everyone with a little empathy. In the case of your trainees, they are going to be relatively green (unlike the Glengarry Glen Ross guys), so there are certain basic lessons that you’ll need to impart. Getting frustrated with rookie mistakes or naiveté only hurts their growth.

Jerry Maguire (1996) – Channel Your Mentor

Sometimes, your own mentors are the best models. In the movie Jerry Maguire, we see snippets of Jerry’s late, great mentor Dicky Fox. And up until Jerry has his late night epiphany, he’s completely strayed from Dicky’s teachings, as you can see by the way Jerry’s protégé Bob Sugar (played by Jay Mohr) acts. As an interlude between scenes, the director cuts over to Dicky spouting simple wisdom to the camera:

“The key to this business is personal relationships.”

“Unless you love everybody, you can’t sell anybody.”

“Roll with the punches. Tomorrow is another day.”

A return to those lessons inspired Maguire’s manifesto, which ultimately led him to a less shallow, more fulfilling life. If Jerry Maguire had put emphasis on the lessons he learned from his mentor, maybe Bob Sugar wouldn’t have turned out to be such a slime bag.

Think of the lessons that stick out from your training. Most lessons about the core strategies of the sales world don’t fully fade from relevance with time. By using the stepping stones that have brought you across the river, you save yourself a lot of mental strain trying to reinvent lessons from scratch. Why get rid of what works?

Forge Your Own Path

Though the tips for sales mentors from these movies are all great guides, it’s important to also forge your own path. Your sales trainee will have his or her goals and will require unique direction. In those instances, you’ll need enough freedom to adequately propel your sales trainee in the right direction.

That’s what we offer at IDR.

With us, there are plenty of opportunities for experienced sales professionals to take the reins and become truly effective sales mentors. If you are interested in working with enthusiastic salespeople to help your clients, your coworkers, and your career, apply for our senior account manager position.


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