Mentoring is one of the most important but oft-neglected elements of the business world. While some companies set up formal programs while others are more ad-hoc, it's generally understood that mentoring helps younger workers come up to speed more quickly.

Like most skills, mentoring requires role models, which means that people who've never been well-mentored are unlikely to become effective mentors themselves. Fortunately, mentoring is a popular theme in film and television, presenting role models galore.

Of all the many films about mentoring, these are the five which, in my view, are both useful and exceedingly timely:

1. Up In the Air (2009)

Human resources consultant Ryan Bingham (whose specialty is laying people off) mentors the young and ambitious Natalie Keener, who is pioneering a program to fire people via teleconferencing. She quits after a laid-off employee commits suicide. Ryan gives her a glowing recommendation that allows her to land her dream job.

This film is notable for its highly-realistic portrayal of corporate behavior and the ethical responsibility of employees functioning in a generally amoral environment. What's most important here, however, is that there is not the slightest bit of sexual tension between Ryan and Natalie. He treats her like a daughter not a potential girlfriend, which is as it should be.

Insight: Mentoring is parental not a romantic relationship.

2. My Fair Lady (1964)

Elocution specialist Henry Higgins teaches a lower-class, thickly-accented, Eliza Dolittle, how to speak and act like an upper-class Englishwoman, thereby proving (after much singing and dancing) that the supposed superiority of the ruling class comes from nurture rather than nature.

Because Eliza ends up with Henry at the end of My Fair Lady, it would seem to run contrary to the "no romance" lesson described in Up In the Air. In the original play, however, Eliza marries the hapless toff Freddie and leaves Henry, having clearly outgrown him. To fix the film and return it to the real world, simply remove the cringeworthy final scene ("Fetch my slippers!"). The edited result is immeasurably superior.

Insight: Mentoring prepares the mentee to transcend the mentor's teaching.

3. Donnie Brasco (1997)

Elderly gangster "Lefty" Ruggiero mentors young thug Donnie Brasco in the ways of the mafia, unaware that Donnie is actually an undercover FBI agent. When Lefty discovers Donnie's true identity, Donnie tries to convince Lefty to leave the mafia. Lefty insists Donnie must complete a contract murder or Lefty will be forced to murder Donnie. Lefty is then arrested. 

Lefty is a violent psychopath teaching Donnie to be the same. Nevertheless, a deep affection develops between the two men. Even though Donnie is playing a role, he subconsciously absorbs and incorporates Lefty's twisted mores into his own value system. 

Insight: Mentoring is as much about worldview as it is about knowledge.

4. The Empire Strikes Back (1980)

Yoda young Luke Skywalker's mentor becomes, in training to be Jedi Knight. When Luke a presentment of his sister and friend in peril receives, Yoda's objections Luke unwisely ignores and the swamp planet Dagobah leaves. Luke, ill-prepared, his right arm loses as Darth Vader in huge plot twist as Luke's father is revealed. (Spoiler was; sorry I am.)

Kidding aside, the Yoda/Luke relationship rings true especially in the way it ends. Luke is too inexperienced to know that it is not yet time for him to "leave the nest" and that by doing so, he will make the situation worse. Yoda knows what's likely to happen and could have easily disabled Luke's X-fighter, but instead allows him to leave and make his own mistakes.

Insight: A mentor cannot force a mentee to remain in training.

5. Finding Forrester (2000)

Author and recluse William Forrester secretly mentors teenager Jamar Wallace. Jamar is accused of plagiarism, a charge that he could easily refute by revealing his relationship with William. Jamar refuses to do so, so William comes out of seclusion to set matters straight. William dies of cancer, making Jamar his heir and literary executor.

While Jamar is ostensibly the person being mentored, the process of mentoring brings William out of his shell and back into the real world. The mentoring (and its direction away from William's own problems) frees up William's creativity, allowing him to complete his second and final novel.

Insight: Mentoring benefits the mentor more than the mentee.

Published on: Feb 6, 2019
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