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The game of leadership is a lot like the game of chess. With multiple moving parts and constant changes, chess masters have to stay aware of their surroundings with an eye on their pieces, their competition, and the future.

Alan Trefler is well aware of the similarities between chess and business because he is a master of both. As founder and CEO of Pegasystems, he has grown the company from a handful of employees to more than 5,000 global employees. He is also a champion chess player and tied for first place in the World Open Chess Championship before founding Pega. Alan has led his company through tremendous growth—Pega was founded before the internet was invented and is now a leading technology company.

Like champion chess players, Alan believes leaders must be looking towards the future to consider a variety of scenarios. Understanding chess helps understand the world of business and leadership. As a chess guru myself, I loved chatting with Alan for my book The Future Leader and hearing his comparisons between leadership and chess.

Alan uses a three-phase approach to chess that is as applicable in the game as it is in business and leadership. He begins by looking for similarities between the board and anything he has seen before.

Then, he works his way through a scenario. Alan takes the similarities that appear to be most interesting for him or most risky for his opponent and then pictures what would happen next if he were to take certain actions.

His final step before making a move is to take a step back and ask himself what he’s missed. The goal is to avoid falling into a trap because he was too excited to move forward.

This way of thinking is critical for future leaders to stay aware of what is happening around them and to move their companies forward while avoiding as much risk and disruption as possible. Taking calculated risks and understanding different scenarios and outcomes is crucial to leading in an uncertain world.

Awareness And Staying Informed  

When Alan played in his first chess tournament at 12 years old, he was fooled by a subtle chess move and ended up losing all five of his first official tournament games.

That experience has stuck with him and taught him the importance of being aware of your surroundings.

One of the most important skills for future leaders is being informed. Leaders must be highly knowledgeable so that the things they do and the things they promote are sensible. Instead of getting distracted by something shiny like Alan did in the chess game, successful leaders focus their awareness on what really matters.

Formal authority is becoming less and less important, which means that leaders don’t automatically have followers just because of their job title. Alan believes leaders must have an informed opinion, which comes from researching and staying alert.

“The way you know you’re a leader is that people choose to follow what you say and what you advocate,” Alan said. “I think that the era of the imperious leader is going to decline, both because of bad examples and because people increasingly seek a level of independence, where their decision of who to follow will ultimately be what makes leaders leaders.”

To Alan, leadership is defined by character and the ability to show a level of reliability to the people who follow you. We’ve moved past the era of coercion, and people now have choices about who they follow. People want to follow leaders who are aware and dependable and not distracted by subtle chess tricks.

Listening and Being Persuasive

Alan believes one of the most important skills for future leaders is also one of the most overlooked: listening.

“For people who tend to be quick to answer, sometimes you can come to answers without properly understanding the context of the questions,” Alan said. “I think listening skills are important today and will be increasingly important in coming years, because frankly, fewer and fewer people listen well.”

Listening to all types of people, not just other executives who always agree with you, is what pushes leaders to consider new perspectives and opens the doors to new possibilities and opportunities. Truly listening allows leaders to form stronger opinions and stay in tune with the needs of their employees and customers.

The best leaders don’t jump to conclusions, but instead are open to new ideas and seek new opinions. Listening takes on many forms, from asking questions during meetings to seeking out feedback and having a variety of conversations. Truly listening to feedback helps leaders see connections, just like chess masters look for connections on the board.

Working With Technology

As we move towards the future of work, many people are concerned about the growth of AI and technology, especially in regards to losing their jobs or being made obsolete by technology. But Alan believes the best leaders will work with technology while tapping into their inherently human traits.

Alan ties it into chess by thinking of Garry Kasparov, which created advanced chess, or the ability for a strong player to join with two or three computers to work in tandem and combine the insights and intuition that humans are so good at with the computer’s mechanics and ability to avoid errors.

“I think that for the next decades, we’ll see increasingly people and computers operating in a symbiotic fashion, as opposed to technology that is detrimental to humanity,” he said, although he noted it may take some time to develop those relationships.

Leaders who can best harness technology and work with it instead of against it will be prepared for the future of work. That means understanding and staying abreast with new technology and experimenting with new ways to automate and digitize aspects of your company to drive efficiency and growth.

Like the complicated game of chess, leadership has numerous moving parts and potential outcomes. To avoid getting checkmated, leaders need to stay aware and informed, listen, and work with technology. With the right strategy, future leaders can have a victorious outcome.


If you enjoyed the article and want more content like this here’s what you can do:

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