What Can You Learn About Sales from The Departed

What Can You Learn About Sales from The Departed

The Departed, Martin Scorsese’s all-star Academy Award-winning movie—that does for Boston what Goodfellas did for New York—is about to turn 10 years old. But what does the brutal cops-and-robbers movie have to do with your sales team? 

These three quotes from Frank Costello, played by Jack Nicholson, will help you find ways to motivate your team like a (gang) boss.

No one gives it to you; you have to take it.

Jack Nicholson The Departed

Rainmakers are, more often than not, born, not made. They are persuasive, they persevere and they perform at the very top of the sales results table. And sadly for sales managers, they’re fairly rare. So while you can try performance managing one into existence, it’s personal traits rather than professional application that create them. If you want one on your team—and you do—you’re probably going to have to hire one.

Your rainmakers are great at managing themselves and their time. They don’t need a manager to spoon-feed leads or direct their activities because they already did that. This morning. While they were eating breakfast on the treadmill while making a call to a prospect in another time zone.

These people are the sale people who have:

  • broken their annual and monthly goals into weekly and daily goals
  • created a plan to achieve those goals
  • organized their time and resources to work the plan
  • selected KPIs to evaluate their own success

They build an effective sales technology stack to make their job easier. You’ll find them with some kind of marketing automation tool like HubSpot; a CRM like Salesforce; and a sales intelligence tool like Winmo. They know that their time is best spent talking with customers, not writing emails and digging up contact info for prospects.

What they really need from you—to motivate them—is regular check-ins, and then to stay out of their way while they get to work. And really, if you google “how to motivate a sales rainmaker” you’ll see that most of the results focus on how the best sales people motivate themselves. It’s not about the money, it’s not about the lifestyle—it’s about being the first, fastest and best to the goal. You could literally make the carrot of motivation an actual carrot and they would work just as hard for every sale.

If you consciously seek out these traits and habits when you interview for new sales positions, you’ll find your rainmakers.

You can’t trust a guy who acts like he’s got nothing to lose.

Matt Damon The Departed

They say negotiations should be a win-win. For you, for your customer, for both of your organizations. But if there’s a trick to getting more of what you want, it’s in making the other person think you can walk away from the deal at any time and not feel like you’re missing out on anything.

Negotiation isn’t about dollars and cents, no matter what you’ve heard. How do we know this? Because a $100 bill is worth more to you than a $100 Starbucks gift card. The flexibility of a Benjamin means that you can spend it in many more places. However, that $100 Starbucks card might be worth more to you than a $100 worth of British pounds, which you’d need to exchange for dollars before you could spend them. That same $100 has different values depending on its flexibility and the desirability of what it can buy.

What negotiation is about is:

  • what each bargaining partner wants
  • how they value those things
  • how they value the things the other partner is prepared to offer
  • why they’re willing to offer what they’re offering

If the person on the other side of the table is acting like they have nothing to lose, they’re either willing to walk away because they legitimately have other offers they feel are just as good as yours, or they want you to think they do. Psychologically, this fear of missing out will likely give you a greater incentive to meet their requirements, even to the point you give up more than you intended to or are comfortable with.

While it’s tempting to dig your heels in and set a hard line yourself at this point, if you take a friendly tone and encourage the other party to explore their options and do what’s right for them, you’ll soon find out whether they really can afford to walk away. If they do walk that’s okay. You didn’t want to work with someone who wasn’t trying to help you win, too. If they come back, you’ll understand that they probably didn’t have so many offers to look at, and that strengthens your bargaining position.

He never wanted money. Can’t do anything with a man like that.

Leonardo DiCaprio The Departed

People are motivated by different things. For some people it’s being able to take exotic vacations every year. For others it’s the new car with the premium audio and kangaroo leather seats. And while these things cost money, most sales people aren’t motivated by money alone. So what else works?

As a general rule, sales people have a higher competitive drive than just about anyone outside of sports. When they see their target, they see a challenge to be overcome. So whether that challenge is a dollar amount for sales or a number of deals closed or sales calls made, they’re motivated by competition.


Hitting goals and meeting targets every month is no small thing. Being called out for accomplishments, and celebrating them with their peers, can drive good sales people to become great sales people. For those sales professionals who don’t quite hit their goals, seeing their colleagues being rewarded for their work will make them push harder next time.


The best sales people have a habit of helping others. Whether it’s sharing tips on organization or referring leads or just being available to talk about how to handle a particular customer, being a leader, and being seen as a leader, is the easiest way to go from sales person to sales manager to vice president of sales. Most of us want to see that our career has an upward trajectory. If you have someone on your team who exhibits these traits, giving them some leadership responsibility and authority, along with a safety net so they can fail safely, is a big motivator.

Having said all of that…nobody works for free. Work out a compensation package that enables your team to worry about making sales rather than making their mortgage payment, while providing incentives for your higher performing team members.

And one final piece of Frank Costello wisdom for that person on your team who just needs to hear it sometimes: When you decide to be something, you can be it.

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