Those of you who know me have probably noticed that I never sit down at the table without a camera to take pictures of positions that challenge me so that I can analyze them later. Many top players are now video-taping their entire match and analyzing every move, and every serious player studies positions in Snowie or one of the other computer programs on a regular basis.

I would estimate that a serious player has at least 4 or 5 checker play or cube decisions every game that he is not entirely sure about. We have all developed our own decision-making strategy for these situations. A beginner sees a couple of alternatives, thinks about them a little, and then makes his move. An intermediate player might move the checkers for each possible position, look at two or three moves, and then make his best guess.

A world-class player, when faced with a tough decision, goes through a much more complex exercise when faced with a tough decision. First, the world-class player has a huge database of what we call reference positions stored in his head. He has a lot of experience both over the board and through study so that for almost any situation he can remember very similar situations that have come up that he can reference to help him decide what to do. In addition to the reference positions, he also does very complex mathematical calculations. Depending on the situation, he will count the race (pip count), he might count the number of possible hits, repeat shots, return shots, percentage of wins and losses, percentage of gammons and backgammons, match equity differential for various decisions and outcomes, price of gammons (both ways), and take points. In addition, he factors in any considerations relative the skill (or lack thereof) of his opponent.

But regardless of your skill level, I have one suggestion that will help you make tough decisions, and it doesn't matter whether it is a checker play decision or a cube decision: Put yourself in your opponent's shoes.

Before I go into detail on this strategy, I have to admit that I first learned this strategy from one of the greatest players and teachers in the game: Kit Woolsey. About 20 years ago I paid Kit to give me lessons on line, and in just a few lessons, he raised my game from a low intermediate to an open level player. (By the way, when I was a lower level player I had no idea I was making so many bad moves; now, I fully appreciate all my bad moves.)

One of Kit's lessons was about doubling decisions, and I use it every single time I think about doubling: "Put yourself in your opponent's shoes and ask yourself if you are sure it is a take or sure it is a drop. If you are not sure whether it is a take or a drop, then for sure, it is a double." (If you are sure it is a take, it might still be a double, and if you are sure it is a drop, then for sure it is a double unless you might be right to play on for gammons.)

After applying Kit's advice for a while, and after seeing how well it worked and how much it helped my game, it occurred to me that I could apply the same strategy to every situation. I soon found that worked well for every decision I had to make.

In essence, whenever I have a tough decision, after looking at all of the variables I mentioned in earlier paragraphs, if one play or cube decision doesn't clearly rise to the top, I then put myself in my opponent's shoes and ask myself how I would feel if the other player made play A, B, or C, or if he took or dropped the cube. And if, as the other player, I would hope he doesn't make play C, then I know that play C is the right play to make!

This has helped me tremendously in cube decisions when I am doubled. If I am not sure if I should take or drop, again, I first consider all the variables including estimating wins and losses and gammons and cube volatility and match equity etc., and then if I am still unsure, I pretend I am my opponent and I ask myself: "Would I be happier if he took or if he dropped?"

Most of the time the answer comes in the form of a feeling rather than in an analytical response. We all know that feeling I'm talking about. You turn the cube, and as you sit there watching your opponent thinking about whether to take or drop, you are often sitting there hoping he will take, or sometimes you are sitting there almost praying he will drop because you weren't sure you should have doubled in the first place and you know that if he takes he might be giving that cube back to you in a roll or two if things go badly. Sometimes the only reason I even give a cube is because I am hoping my opponent will make a mistake and drop. So I have found that when I put myself in my opponent's shoes, I am able to experience that feeling for myself, and that pretty much tells me what to do.

For checker play decisions, the feeling isn't quite as strong, but the strategy works just the same. Do I want him to hit me and leave a direct shot and give me a chance to gammon him? Or would I prefer he plays "too safely" and leaves no shots and stacks up all his checkers so that he is inflexible for the rest of the game?

Often I have a tough checker play decision when the cube is in the center or on his side of the board. I put myself in my opponent's shoes and ask myself if I would double if he makes Play A, B, or C. If I would probably double if he makes Play A or C, but not if he makes Play B, that pretty much tells me that I should go with Play B.

I hope this strategy helps you as much as it has helped me, and I dedicate this article to my old good friend and great teacher Kit Woolsey, with my thanks for all he has added to the game, not just as a teacher and player, but also as one of the great writers, innovators, and promoters of the game over the years. (Kit was the promoter of FIBS—The First Internet Backgammon Server, which brought backgammon to the internet and has thus been responsible for a great deal of the growth of the game over the past 20 years.)

One last note ... over the years I have also developed a strategy to add on to Kit's, and it has become known as The Simborg Rule. And the Simborg Rule is simply this: after you think about whether you should double or not, again, put yourself in your opponent's shoes and ask yourself: "Would I really hate to be doubled here?" If the answer is "yes" then double. If the answer is "No, it wouldn't be so terrible to get doubled here," then don't double. The Simborg Rule is to cause as much pain and discomfort as you can to your opponent, whatever that is. The same thing applies to checker plays. Ask yourself what play you hope your opponent won't make, and then you know that's the play to make!