The experience got me thinking about the parallels between chess and sales. Since its origin in the 15th century, Chess was and is one of the most basic forms of strategy and vision. Experienced players often plan 50 or more moves in advance of a match, including specific opening and attack sequences. Through years of practice and study, masters gain the ability to perceive key patterns in any given position. According to a 1999 CIA study, the masters had near total positional recall when all pieces are removed from the board.
Benjamin Franklin, in "The Morals of Chess" (1750), wrote: "The Game of Chess is not merely an idle amusement; several very valuable qualities of the mind, useful in the course of human life, are to be acquired and strengthened by it, so as to become habits ready on all occasions; for life is a kind of Chess..."
Whether or not you play chess, you can employ key components of the game to improve your sales effectiveness. In complex sales environments, it is imperative not only to plan your strategy in advance of and during your sales engagements, but also to anticipate every possible problem or challenge. Remember these key elements of chess in your next opportunity:
Understand how the pieces move (each player has 16 pieces under his control at the start) To what extent do you understand your customer's business? What does the buying process look like? Who are the key players and what motivates them? What behavioral patterns can you identify and leverage?
Know the experience level of your opponent (amateur to grandmaster) How well do you know your competition? Can you anticipate their moves? What makes yours the superior solution? How can you help your sponsor win and vice versa?
Minimize attrition of key pieces (protect your Rooks, Queen and King) What moves are your customers likely to make? Has your prospect done this before? What happened last time? How can you negate the competition's strengths and exploit their weaknesses? What tanglible and intangible elements or requirements will provide advantage?
Achieve Checkmate (Victory for you and your customer) What will it take to win? How will your execution plan ensure success after the sale is consummated?
Some might say that the chess analogy is too adversarial for the new paradigm of selling. After all the customer is a partner, not an opponent, right? Absolutely true as the relationship matures. In order to get to that point, you need to employ a chess-like strategy with preparation and intelligence!
Interested in learning more about chess strategy? Check out these books (which go much, much deeper into the game):
- Practical Chess Exercises: 600 Lessons from Tactics to Strategy (2007)
- Weapons of Chess: An Omnibus of Chess Strategies (1989)
- Chess Tactics for Champions (2006)
Pick one up and you'll have a leg to stand on next you visit Harvard Square...

