How chess can nurture essential critical thinking skills for business leaders

March 31, 2023 | By Safdar Khan
A common analogy when talking about business strategy is the game of chess. The similarities are clear, particularly the high amount of planning, calculation and tactical execution that is involved in both.

At the same time, however, the differences are stark. Chess is a zero sum game, usually with one winner and one loser, and with set rules and finite resources. Business, on the other hand, is rarely this clear cut. Business can have multiple winners, competitive collaborations and of course involves people, who act very differently from chess pieces.

That’s not to say that chess has nothing to teach the world of business. Far from it. As a keen chess player, I like to observe how chess can help develop “softer” skills such as adaptability, agility, creativity and more. Characteristics that not only have benefits in everyday life but can also help us to formulate more successful business strategies.

Let’s look at these in more detail.


The sheer number of possible moves and combinations means every chess game will be different, which necessitates meticulous planning.

But, as the famous adage says: “No plan survives first contact with the enemy”.  A chessboard is a constantly changing landscape, and a winning position can turn into a losing one in the spaces of several moves. This is why plans need to be flexible and players need to be able to adapt to unexpected change.

As business leaders operating in a similarly complex and unpredictable landscape, we need to show comparable adaptability. Or, as we say at Mastercard, the ability to learn and pivot. Markets change, technologies advance and customers have new priorities. When this happens, we need to identify when a plan is no longer relevant and adapt accordingly. The key is to be agile enough to prioritize what matters.

Nurturing creativity

Chess is seen primarily as a game of logic that requires exceptionally high familiarity with set patterns and potential outcomes. This is without question true, but chess also encourages the development of other skills around creative thinking and problem solving.

Business strategy has a similar duality, this time between the world of operations and the world of innovation. One is concrete, structured and functional, while the other relies on curiosity, creativity and experimentation. However, neither can function effectively alone. The skill – as with chess – is knowing how to navigate between the two and how to create an environment where both can co-exist and flourish.

Too often we see creativity as something a person either has or doesn’t have. But chess shows that creative thinking can be learned and nurtured through practice. We may not all have the inherent potential to be the next Michelangelo, but we do all have the ability to formulate a creative outlook and use it to think big and be bold.

The virtues of patience

Chess requires focus, concentration, and as noted above, a certain degree of creative thinking - all crucial attributes for both business and life. But one of the most obvious and yet underrated aspects of the game is understanding the value of a patient approach.

A mistake often made by inexperienced players is to stop searching for solutions once they’ve located what they see as a good move. It’s easy for them to forget that there might be a better move available, given time. Or as the German mathematician and chess player Emanuel Lasker noted: “If you see a good move, look for a better one.”

In business as well, the first idea is not always the best idea. Exercising patience while the world around you moves at seemingly breakneck speed is no easy feat, but is nonetheless a trait worth developing. But we should be careful not to equate patience with being slow or indecisive. Moving fast and showing patience are far from incompatible, and when combined can be a crucial contributor to business success.

Trusting your intuition

It may be strange after all the talk of adaptability, creativity and patience to then argue the case for relying on intuition. But that’s because we too often mis-characterize intuition – or trusting your gut – with recklessness, when in fact it is anything but.

Good intuition comes from experience and practice. It is developed over time from successes and failures. In chess, for example, pattern recognition itself can be seen as intuitive, particularly at the highest level. It is intuition that allows a player to make quick and decisive moves based less on conscious reasoning and more on familiarity with patterns they’ve observed countless times over the course of their playing time.

In business strategy, intuitive decision making can be an invaluable trait. Steve Jobs, for example, attributed much of his success to intuition, once saying he believed it more important than intellect. What we learn from chess though is that intuition is rarely an uninformed shot in the dark. Good intuition needs time to grow and become reliable. It also needs to be tested against relevant data and insights. Only then can it become an important part of a business leader’s toolbox.

When it comes to chess, we can’t all become Grandmasters but we can certainly all enjoy the intellectual and competitive stimulation the game provides. Whether playing to compete at a high level or just looking for a relaxing hobby, chess will help you develop and practice the traits above, which can then be applied to business and leadership.

If you have never played chess before. it’s never too late to start. Thanks to the boom in online chess, the pastime is more popular and accessible than ever before. And don’t be afraid to be a beginner. As the Cuban chess master José Raúl Capablanca once said: “You may learn much more from a game you lose than from a game you win.”

Photo of Safdar Khan
Safdar Khan, Division President, Southeast Asia, Mastercard