Leadership lessons from The Princess Bride


“You keep using that word. I do not think it means what you think it means.”

“The Princess Bride” has become a classic movie. Those who watch and re-watch the movie can recall many of the characters’ most humorous, moving, and inspirational quotes. August is pirate month, according to the bookshelf at the local library where I'm doing my Business Growth Workshops! (See what those are here.) For a light-hearted break this week, let’s look at a few of the leadership lessons to be learned from The Princess Bride.

Ultimately, the biggest lesson of all is positive perseverance in the face of insurmountable obstacles. Like Westley and Buttercup, if you can muster the grit to keep moving forward in the face of everything that can be thrown against you, you will succeed.

Here are some other leadership tips. Each is based on one of the quotes from this now-classic movie.

  1. “He didn’t fall? Inconceivable!” Conceive of the inconceivable. Challenge your previous ideas about what can and can’t be done. Stretch your thinking and your teams’ thinking by asking questions like, “Well, what if we could…?”
  2. “You keep using that word. I do not think it means what you think it means.” Words do not always mean the same thing to different people. As a leader, it’s your job to prevent misunderstandings by taking the time to clarify. This is especially important in a remote or hybrid environment! Make sure that everyone has the same understanding before taking action.
  3. “I always think that everything could be a trap, which is why I’m still alive.” Be alert to the implications of decisions before moving boldly ahead. Certainly, actual traps are few and far between. But as you think about making changes, consider the potential unintended consequences of your proposed course of action.
  4. “Hello. My name is Inigo Montoya. You killed my father. Prepare to die.” Introduce your proposals with positivity, clarity, rationale, and purpose. While I might not suggest going as far as Inigo, the clarity of his classic introduction sets a mark for leaders who want to get their messages across. (But please, avoid any hint of threat in your own communication!)
  5. "Don't rush me, sonny. You rush a miracle man, you get rotten miracles." Take the time to do the job right. Don’t push your employees to rush their work, either.
  6. "Have fun storming the castle!" Approach even the toughest tasks with a sense of playfulness and fun. If you can do this, you lighten the load on yourself and make it easier for your team, as well.
  7. “As you wish.” While it may seem corny and un-businesslike, remember that there is purpose to what we do. If you approach your work—especially the things that frustrate or stress you—with a sense of love, obstacles will be much easier to handle and your outcomes will be greater.

If you are a fan of the movie, I’m sure you have your own thoughts. Please reach out and share those with me! As always, let me know what you think or feel free to schedule some time to chat.

As you wish,
–Steve

Steve Semler

Leadership matters! I help leaders develop the skills and capabilities they need to be successful in all four areas of technical leadership. As a business coach I stop businesses from failing. I use an AI-enabled simulation process to help business owners find revenue and profit opportunities "hideen" in their financials and track their numbers. This newsletter has short, easy tips and stories for anyone interested in leadership. Enjoy!

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