princess-bride-leader-rolesThe slyly comic cult classic The Princess Bride has been in the news lately thanks to Republican presidential politics. It’s struck me that many of the leading roles show up from time to time in organizational life today, almost 30 years since the movie was made. So if you’re also a fan of The Princess Bride, you may recognize some of these types in your workplace. And if you haven’t seen the film yet, it’s a treat. But be warned: Some spoilers are included!

The Princess Bride’s Main Male Roles

Westley starts out as a farmhand whose apparent subservience veils his own definitiveness. “As you wish,” he declaims, over and over again, to Buttercup, his true love. His style is laissez faire with a twist: He cares more about relationship than mission, but no matter what his job or level of accomplishment, he’s clever, self-contained, and incredibly competent.

An interesting mix of sang-froid and empathy, Westley is an excellent bluffer and therefore a good negotiator, too. He’s comfortable taking a public back seat and letting events unfold around him while he stays true to his course. But can he ever lead from the front, saying what he wants, sharing his vision? Or will he step up only at the point of a sword?

Prince Humperdinck is a leader in title only. His development appears to have been mismanaged by the prior administration, and except for the accident of his birth, he probably wouldn’t — and shouldn’t — have gotten the job at all. He only wants what’s good for him personally, and to be in charge purely so he can satisfy himself. He relies on flatterers and others’ weaknesses, and is happy to treat people as pawns to the extent of kidnap and murder if it serves his ends. He’s a big coward and a cheat.

Any sane colleague would want Humperdinck off the team. Even his most successful subordinate barely tolerates him.

Inigo Montoya is single-minded, committed, and intense. He’s a terrific colleague if you’re heading in a direction that serves his personal goal, and he’s reasonably self-knowledgeable, but he doesn’t have enough sense of the big picture to be ready for leadership. He’s been practicing for his defining encounter since childhood, and has virtually no other experience. Yet he succeeds thanks to his tremendous drive and dedication, coupled with a mantra that helps him achieve focus at the crucial moment.

Inigo will need a new mission for ongoing motivation. He may also need to learn some additional skills, and he’ll work to pick them up if his new role is interesting and meaningful.

Vizzini is supposed to be a clever mastermind type, but he’s really a petty despot and braggart. He thinks he’s the smartest guy in the room, and expects you to think so too. He’s also a little paranoid, but why shouldn’t he be? Vizzini is horrible to everyone, so of course he can’t trust anyone. He’s so full of his own smarts, he doesn’t recognize others’ potential, so he’s bested by someone who’s quieter, but savvier and better prepared. Luckily, no one will ever have to work with Vizzini again.

Fezzik is an excellent team player who can apply his unique talents to any situation. He gives 100 percent to his leader and teammates, and does so kindly and without drama or rancor. He’s seen it all, and never gets flustered. Just give him good assignments, and he and his team will be very satisfied.

The Grandfather is the most clearly developmental leader in the bunch. He sketches out a path so his Grandson can make his own choices, have his own experience, and draw his own conclusions. He’s an artful and loving mentor. The Grandson is curious, open, and teachable — after all, he’s only 11.

Short Shrift for Female Characters

Unfortunately, in classic corporate tradition, the female characters in The Princess Bride are relatively incidental. Even Buttercup, the heroine, is a traditional feckless ingénue and pawn. She’s naïve and not so swift on the uptake. She’s missing grit, tough-mindedness, and resilience altogether. She’s easily hoodwinked, and is willing to kill herself rather than work harder to prevail. In the long run, maybe Buttercup would do better with a real mentor — someone less indulgent than Westley — not to mention a different story!