Chess and Strategic Leadership: The Overlooked Middle-Game


Chess is about making strategic decisions. From the very first move to the last, it is all about how you deploy, position, support and utilize your resources to get the best results. As such, chess is a very useful analogy to all kinds of strategic decision making – be it in leadership, entrepreneurial ventures, school innovation, job hunting, and even our personal lives.

The Opening

The opening is all about how we position our pieces. The goal here is to deploy all of our major pieces to key squares where they can exercise influence over the board and over other pieces.

In strategic leadership, this equates to how we acquire, position, and maximize our capital, our human resources, and our physical infrastructure. A good opening foray is thus about getting the best resources possible into play as early as possible. This is important not just in leadership, but in life more generally. Even though we might have physical limits, as players do with the number and abilities of pieces, we should identify and deploy what we have as soon as we can.

There are some minor exchanges in the opening, but if you’re playing well, you are generally swapping poorly placed and weaker pieces for stronger ones, and you are getting pieces linked up to coordinate their efforts and to support one another.

The opening generally takes far longer than most players realize. But it shouldn’t take too long, otherwise the opponent might already be on the middle-game and thus have a tactical advantage.



The Middle-Game

This is the most neglected phase of a chess game. In chess, as in strategic leadership, many average players move directly from the opening to the endgame, without a proper understanding of the tactical advantage a strong middle-game can have.

A properly played middle-game leverages the positions and connections put in place in the opening. This is where a player’s tactical and strategic decisions matter most: It’s all about taking on multiple targets simultaneously, in a coordinated and intentional fashion, and about revealing subtle hidden tactics. 

The middle-game involves carefully coordinating, supporting, and manipulating your resources, as well as seizing the initiative and playing intentionally. In this phase, creativity, adapting to change, problem-solving abilities, and pattern-spotting proclivities are incredibly important.

The middle-game is a rich, multi-faceted phase of a chess game, and knowing how to play it makes good players into great ones. It is here that we talk about tactics like forks, pins, skewers, discovered attacks, and overloading.

In strategic leadership (and in life’s challenges), this is analogous to actually exploiting the resources you have put in play in the initial phase of a project. This is the phase where you need to be deliberate and cautious, and where you need to analyze carefully. But it is also the place where true innovation, risk taking, and problem-solving can seriously boost your chances of success.

The opposite to a well played middle-game is a mechanical, reactive approach, where you respond to moves made by others rather than taking the lead. The result can often be a loss of critical resources, which puts you on the back foot as you approach the final phase of a project.

The middle-game is basically where a game is either won or lost. And it is the arena in which the most serious blunders occur. (A blunder is a move which loses a critical piece, and thus loses you the game.) Most often, blunders are not simply ‘mistakes’, they are as a result of either not seeing the whole board, and thus obsessing with just one part of it, or of neglecting critical, threatened pieces.

The Endgame 

It is difficult to define when the endgame actually begins in chess. In essence, the endgame is an extension of the middle-game, except that the tactics are almost completely prescribed. There is not much room for being innovative. To play the endgame well, you simply have to understand simple tactics like king opposition, zugswang, and check-mating squares. The end game depends on rigorous preparation and a solid understanding of the rules of an endgame.

In leadership, the endgame is wrapping up a project. It is ensuring that your tactical advantages are carried through, and that things are properly concluded.

Interestingly, while most people are infatuated with a checkmate and a win, in the endgame, it is entirely possible (and sometimes even desirable) to go for a draw. Often, chess players give up too soon, where they could have earned a draw even from a seemingly hopeless position. Chess teaches us the value of a bit of determination in fighting until the bitter end. (Of course, sometimes a loss is inevitable, in which case, it might be best to resign with a bit of dignity, and focus your energies on diagnosing what went wrong so that you’re better in the next game.)

There are some very useful analogies in a game of chess to all manner of strategic decision-making and leadership-related issues. But it is the often neglected middle-game which provides the most useful lessons. Rather than moving directly from planning to results, a focus on the middle-game teaches us to enhance our tactical and strategic acumen in order to protect our assets, or at least exchange them more intelligently, and thus to leverage better results.

I’d love your thoughts. Please add a comment below.

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About Sean Hampton-Cole

Fascinated by thinking & why it goes wrong➫ (Un)teacher ➫iPadologist ➫Humanist ➫Stirrer ➫Edupunk ➫Synthesist ➫Introvert ➫Blogger ➫Null Hypothesist.
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2 Responses to Chess and Strategic Leadership: The Overlooked Middle-Game

  1. fsagwe says:

    Awesome! article on how chess analogy teaches us about leadership.

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