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Thinking Like a Grandmaster

At a recent meeting of the Staten Island Bucks Business Network, my friend Glen Cutrona made a presentation on Your Next Five Moves: Master the Art of Business Strategy by Patrick Bet-David. I heard that we were going to “learn” how to think like a chess mater, how to think five moves ahead. What was presented instead were the author’s suggestions on the next five steps which all business people should take in their learning. I wanted to hear a talk on thinking ahead in business. How do you teach that?


In my excitement, the memories of playing chess a teenager came flooding back. I was really into chess in high school. It was, in fact, my only varsity sport. I played first board on our high school chess team. I studied chess. I played postal chess. (This was long before personal computers and the internet). I dreamt about chess, anxiety-laden dreams in which sections of the chess board appeared schematically with positions from recent games in which I had struggled or blundered. The dreams were wearing me out and I quit chess.


I played a few times with Jamie when she was in elementary school (years before she changed her name to Morrigan), teaching her in the way that my father had taught me, spotting her pieces until as she was able to win, reducing the spot. When I played with her, I hadn’t played in 50 years. It’s now been years since I played with Morri. Then, this last spring I played a few games for the first time in more than fifteen years, with Lavelle Prep 5th graders in a newly formed chess club. I was surprised that I still played better than a fifth grader. In a shelf in an upstairs room, I occasionally notice my chess books. I haven’t opened one in more years than a can remember, and yet they have traveled with me through half a dozen houses and apartments.


Against the Grandmaster


When I heard Glen talking about thinking like a chess master, it got my juices flowing. I played a game once against a chess grandmaster, Arthur Bisguier. In high school, I would take the train into the city to the Manhattan Chess Club to play. One evening, I got to play a game with Arthur who was then the US Champion. I was the top player in our high school, and he disposed of me as easily as I did those 5th graders. It was wonderful.


In building our schools, I often had the sense that I was using what I had learned playing chess to think strategically. But it was something that I was never able to teach. “Wow, this is wonderful,” I thought. “Someone has figured out how to teach this and to apply it to business and organizational leadership.”


Maybe Bet-David has, but it is not apparently what his book is about. The book is much closer to a chess primer. I have a couple of those upstairs too.


Of course, first you have to learn the moves, what each of the different pieces can do and can’t do, and you also have to learn the point of the game. What’s a checkmate. And what’s a stalemate.What’s a draw. You can also learn how to handle some simple repetitive occurrences: how to checkmate an isolated king with a limited set of pieces. In the beginning, my friends and I would practice these endgames over and over. You can also learn some principles of strategy, the importance of pawn structure, the importance of control of the middle. And you can memorize opening sequences.


Bet-David offers another business primer. All good advice, I’m sure.


But none of this has anything to do with thinking like a grandmaster.


To think like a grandmaster is to think ahead but it is not as the Bet-David book apparently suggests, an issue of listing the next steps you will take. Most of us have learned the rudiments of planning ahead. My freshman year in college, taking five course, we all had all our finals coming up in the same week, sometimes two in a day. We all learned to make study schedules. How many of us stuck to our schedules is another question. I don’t think I did, but I thought the schedule helped.


The Opponent


Chess is a different animal. It’s not all about me. In chess, I am playing against an opponent. He is making plans too. He also wants to win. So in chess, it is crucial to anticipate your opponent’s play. If I do this, he might do this. He might do that. If he does this, then I’ll do this next move; and if he does that, then I’ll do that next move. There might be many more than two possibilities. How will you respond to each one? That’s thinking two moves ahead. Now imagine thinking five moves ahead. And, as Glen told us, some grand masters think twelves moves ahead. Imagine keeping those strands running.


Chess is a game. At any one point, the number of possible moves is definable and finite. A computer which can do so many calculations should be able to consider all possibilities and given a good enough set of decision rules should be able to defeat the greatest chess player in the world. When the gigantic Univac computer which filled an entire room first played a champion, the grand master won. When the earliest computer chess games appeared, I could beat them; and then the computer and the programs evolved, and I didn’t win anymore. Now even the grandmasters can be beaten by today’s big computers.


Something other than pure computational power is involved. Chess masters do not consider all alternatives. Only those which are most likely. A combination of experience and intuition. The human brain may not be as fast as even a primitive computer but we are smarter than the fastest. (So many scary science fiction movies are anchored in the premise that someday in the not-so-distant future, that will no longer be the case).


The Game of Chess, The Game of Life


Business is a much more complicated game than chess. Life is a much more complicated game than chess.


Chess is played on circumscribed board of 64 squares. In business the size and shape of the board is constantly changing, if there is any board at all.


In chess you are playing against a single opponent who sits across the table from you. In business you are playing against multiple opponents, some of whom you know. Others you have never met. Some you don’t even know exist.


The rules of chess are clear. While there are some laws and regulations in business — more than we would like, we are always complaining about the laws and regulations which restrict what we can do, —in the game of business, it often seems what rules there are are there to broken or subverted. And compared with chess, it is really as if we are competing in a game in which there are no rules at all.


And then, there is the weather. In business, the weather is always changing. In this way, business is more like sailing than like chess. What makes sailing exciting, especially long-distance racing is the variability and unpredictability of the weather. To sail competitively in a climate-controlled dome with constant wind would not be the same exciting game.


So how do you play the business game like a chess master?


Planning Backwards


Yes, you need a goal, an objective. Not just a pie-in-the-sky aspiration but a concrete goal, ideally a measurable goal, that you want to achieve, that you think is achievable in a specific, limited time frame. And then you need to chart out the specific steps that you need to take to achieve this goal. This takes a lot of thinking. In order to get to Z, I need to do Y, but in order to get to Y, I need X. And in order to get X, I need A, B, and C. That’s where you begin. There are plenty of business books and training programs and consultants who will show you how to do this. Some cost a lot of money and take a lot of time to learn. Bet-David offers a kind of catalog of a bunch of the a’s and b’s and c’s that you are likely to need to learn. It’s sort of like learning the chess moves.


But right now, having set your objective and outlined the steps you need to take to get there, all you have is your desires. How do you think like a chess master? Well, if I do this, how are my opponents going to react? How are all the other players who are impacted by my move going to react? This is already complicated. Peter Senge in The Fifth Discipline recommends as a beginning step the use of systems analysis to identify as many of the players who will be effected by your move as possible. Ask yourself particularly, who among these players is likely to be adversely impacted by my move? How might they counter my move?


And then you ask, what will I do then?


It’s getting complicated, but you are beginning to think like a chess master.


And what if the weather changes? What if there’s a change in the regulatory environment? A new mayor imposes new regulations or decides to enforce old ones? What if the stock market takes a dive? What if interest rates skyrocket? What will you do then?


Thinking just this far ahead — this is two moves ahead — can dramatically impact the decisions you are making today. What if you don’t assume that all the other players will simply wish you well, or fail to respond? What if you don’t assume that the weather will hold?


It exhausting just to imagine the brain sweat.


Can anyone actually imagine thinking five moves ahead in the game of business?

But even thinking this far, just two moves ahead, a bare step on the pathway to chess grandmaster, can make a big difference in business.


What’s the point, you may ask. If we’re honest we need to admit that our plans seldom work out. They constantly need to be tweaked and revised. And sometimes scrapped.


Nothing will turn out the way you plan, so why bother planning? Business is so much more complicated than chess. Why bother?


That’s a question for the Zen master not the chess master. How do you think like a Zen master?


Why bother planning if the future is unknowable?


Because planning for the future changes the present.

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