Defeating Your Opponent's Strategy

From Sun Tzu to Princess Bride

Defeating one’s opponent is what we hope to do in all our competitive endeavors, whether it’s on the playing field, a friendly board game, a high-stakes business deal, or conventional warfare. The question is how to do it most effectively and efficiently.

The ancient Chinese master of strategy, Sun Tzu, had this to say on the subject.

An intriguing quote, to be sure, but how do you ensure you can win the battle before it is fought?

I think the Battle of Wits scene from Princess Bride illustrates in a fun way how this can be done. Fought between clever but wicked Vizzini, who has kidnapped the heroine, Buttercup, and Westley, the hero who seeks to rescue her, they each have a strategy to win. Watch the short clip here before reading on.

OK, now that you’ve watched it…let’s analyze the struggle.

To triumph, Westley does what Sun Tzu counsels us to do in order to “win the battle before it is fought.”

Westley proposes a contest to Vizzini of choosing from one of two cups, one of which is filled with poison. Whoever chooses the cup with the poison dies and the other wins. What Vizzini doesn’t know is that Westley has a fail-safe strategy to win, having long-ago inoculated himself against the poison he puts in the both cups.

"Determine the enemy’s plans and you will know which strategy will be successful and which will not..." Sun Tzu

A good strategy is crucial to your success. Allow me to pose a dilemma:

You are faced with two doors; one blue, the other red. If you choose the blue door, you can go back in time and fix all your mistakes. If you choose the red door, you get $10 million dollars.

Which door would you pick? What’s your strategy? Do not read on until you have made your choice!

There are different strategies based on your goals, but the best strategy is to choose the blue door. Entering the blue door, you return to the past and correct all your errors. The last mistake you fix is not taking the Red Door. You fix that by going through it and gain the $10M.

If you want to win the battle before it is fought, it’s all about your strategy!

“The skillful commander takes up a position in which he cannot be defeated and misses no opportunity to master his enemy.”  Sun Tzu

To develop your strategy you must know the possible plans of your opponent and be prepared for them. One way to do this is to wargame the situation by taking the vantage point of your rival and seeing things through their eyes. This must be augmented by intelligence gathered on the situation and your adversary.

A great tool for wargaming is the Implication Wheel, developed by futurist Joel Barker. It was created many years ago but stands the test of time. By putting a strategy of your opponent in the center and playing out the moves and countermoves between you both, you can foresee many possibilities.

As the above example illustrates, the Implication Wheel is also great at thinking about how an event can have 1st, 2nd and 3rd order impacts. I highly recommend it for high stakes wargaming of competitive situations and game-changing events.

In sum, I leave you this quote from the master;