It happened again! A client with an idea for a blog. Speaking with this client last week (a sales leader with a strong pedigree) – he made a pretty cool comparison – Chess and selling. His comment was, “I wish our Sales Team would look at a deal and think 2 or 3 or 4 moves ahead to improve their likelihood of a Check Mate”.
My mind immediately went to the only Chess movie or Netflix Series I have ever watched – The Queen’s Gambit. The eleven-time prime-time Emmy Award winning mini-series based on the 1983 novel by Walter Tevis. If you have seen it, there is no denying how bingeable (yes, it is a word) it really is. Anya Taylor-Joy plays Beth Harmon, a completely captivating Chess prodigy with a few skeletons in her closet.
So, how does Chess compare to sales?
If you are in B-to-B sales, with an expensive product, in a competitive market, doing quotes and proposals that involve sales, engineering, design, and a host of other people in other departments (at your company) let us say that the Economics of Selling can get out of hand very quickly. You need to think things through. A little like Chess?
Have you ever done the math on how many person-hours it takes to prepare a quote in your company? We are talking about: The first sales call, the internal meetings, the second sales call, design (if applicable), engineering, your cost estimators, project managers, a third sales call, and on and on and on. It is a lot. Multiply this by the number of quotes you do in a typical year and it soon becomes clear how what started as a for-profit company quickly looks like a non-profit organization! The pressure to perform. Sounds like Chess
At the prospect you need to pay close attention to your prospects compelling problem (often called PAIN), you need to make sure you are having the “money conversation” and you must be skilled at understanding and maneuvering the decision making process which at times can feel like a maze. You have to do this with your contact in engineering, purchasing, quality, marketing and a host of other people in other departments. More thinking and strategizing. That’s Chess 101
It is expensive to win business. Hell, it is equally as expensive to lose business. It may be the most serious (and expensive) function performed at your company. Winning business is not easy in 2026. It takes hard work, it takes digging in, it takes commitment, it takes having a solid strategy, it takes thinking ahead – often 2 or 3 or 4 moves ahead.
Yet another comparison to Chess.
For anyone who has ever played it, Chess is a challenging game. It takes thought. Concentration. Focus. Commitment. And a solid strategy. It is common for Chess players to take what seems like a lifetime between moves. What they are doing is thinking ahead (if I do this and she does that, then I will do this and she will do that). Thinking ahead. It takes work.
Professional selling in 2026 is not “off the seat of our pants”. Successful salespeople don’t “wing it” anymore. There are dozens of Selling Systems out there that prepare you with a strategy for selling – pick one, commit to it, and watch what happens.
And remember this, whatever selling system you use will require you to think ahead – often 2, 3, 4 moves ahead.
