LM Extras Oct 19, 2023

Legal Leadership Lessons from an Unexpected Place: 'The Princess Bride'

As humans, we have a tendency to overcomplicate things. This is especially true in the legal industry, where making swift, innovative decisions can be a slog. 
Derek Andersen

I believe there are some simple lessons we can take to heart on leadership from The Princess Bride, the 1987 fantasy adventure comedy film based on the book by William Goldman. The movie, full of intrigue and swashbuckling adventure, illustrates several basic tools for leaders of small and midsized firms to employ when working through day-to-day management struggles.

1. Overthinking your decisions really does not accomplish anything.

In the film, Westley and Vizzini become locked in a battle of wits, the winner of which “steals” Princess Buttercup. During the scene, Westley adds iocaine powder to the drinks and Vizzini begins his “dizzying” monologue explaining why he is choosing which cup to drink. Ultimately, Vizzini loses and dies because Westley poisoned both cups, having developed an immunity to iocaine powder.

But the important takeaway here is Vizzini’s overthinking which cup to choose often mirrors how firms agonize over important decisions in real life. The constant barrage of “what ifs” take hold as law firm leaders make decisions on substantive issues. The more and more we think about things, the more paralyzed we become, rendering the decision impossible.

Learning from Vizzini’s encounter with Westley, we should understand that the decision-making process does not have to be fraught with angst. Further, overthinking often does not yield a different result from what could have occurred with less consternation. Gather your information, consult your trusted advisers and follow your instincts. Doing so may open doors and present opportunities in a more constructive way.

2. Badgering and belittling your employees never ends well.

 

Vizzini’s management style of his team is at best belittling, and borders on aggressive. He is far from motivating Fezzik and Inigo Montoya. He constantly reminds each of them of where they came from, using it to show his superiority. Throughout the first half of the movie, he insults them and takes every opportunity to remind them that they are his underlings.

“Learning from Vizzini’s encounter with Westley, we should understand that the decision-making process does not have to be fraught with angst. Further, overthinking often does not yield a different result from what could have occurred with less consternation.”

While anyone reading this would never consciously belittle or insult an employee, being mindful of the words you choose will often be the difference between a successful, engaging and devoted team — and a miserable, unmotivated and unhealthy group of employees. A leader takes blame and gives credit. This should be the cornerstone of your relationship with your employees. Following this path will lead to a healthy work environment for you and your team. Also, this type of communication and leadership style creates a loyal group of dedicated employees.

3. Never give up.

As Westley and Princess Buttercup enter the Fire Swamp, they face unknown perils. No one has survived the Fire Swamp, and therefore no one has lived to tell exactly what to expect. From flame spurts to lightning sand to Rodents of Unusual Size (ROUSes), Westley and the young princess navigate harrowing challenges in the Fire Swamp.

Throughout your career, you will find yourself in situations that are difficult, challenging or feel impossible to overcome. There are two keys to learn from their adventures in the Fire Swamp: First, press on. The only way through challenging situations is, well, through them. As they did through the Fire Swamp, you can get through your most difficult challenges. Second, rely on those who traveled before you. Had someone survived, stories of the Fire Swamp would have been told throughout Florin, reaching Westley and Buttercup and giving them the tools they needed to go through the Swamp unscathed. The road is less treacherous when you have the information you need to avoid fiery dangers.

The Princess Bride is a feel-good movie designed to take you away to a fantasy land where good triumphs over evil. While this fantasy land may not be reality, it can be a guide to better our quality of work life. The movie’s messages can also be a cautionary tale, one where bad management techniques wreak havoc across the land. Which ending do you want?