How to Play Chess as a Leader

Eric Chow
4 min readJul 14, 2020

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In chess, each piece moves differently based on its ability. Compare to checkers where all the game pieces move in the same way. Wise leader plays chess and not checkers as they manage relationship.

Credit: Adlan | Unsplash

When my son was six years old, I taught him how to play checkers. It was a game that was simple to learn as each piece moves in the same way. A few months later, I decided to introduce him to the game of chess. Initially, it was hard for him as he first needed to understand how each chess piece moves. But once he mastered that, he began to explore a whole new world of strategy on how to be better at it in winning.

Think about it. What is the biggest difference between checkers and chess? It’s the pieces. If you want to win in chess, you start out by learning how each piece moves — from the pawn, knight, bishop, rook, queen and king. Once you understand the ability of each piece, then you can plan a strategy to win the game.

Bobby Fischer, the great chess master once said, ‘Winning in this game is all a matter of understanding how to captialize on the strengths of each piece and timing their moves just right.’

This is a picture of good leadership. Great managers understand the people under them and bring the best out of them. Glen Llopis simply put it as “The best leaders are those that can identify and appreciate the differences that one brings to the table and knows how to put them to full use.” Great management is not about control but the empowerment of others. Mediocre managers play checkers with their people but excellent managers play chess. They are able to connect with people at the point of their strengths.

Michael Abrashoff took over as commander of USS Benfold, one of the under-performing ships in the navy. But before he left, in less than three years, he has transformed it into the best ship in the U.S. Navy’s Pacific Fleet. In his book “It’s Your Ship”, he recounts…

Our military has spent a lot of time and money preparing for tomorrow’s battles with antiquated methods. We continue to invest in the latest technologies and systems, but, as we all know, technology is nothing but a facilitator. The people operating the equipment are who give us the fighting edge, and we seem to have lost our way when it comes to helping them grow.

One of Michael’s leadership success in management is seeing the ship through the eyes of the crew. Being the new captain on the ship, he read some of the exit surveys, interviews conducted by the military on why people are leaving. He would have thought low pay as one of the top reason in the list, but in fact it was fifth.

The top reason was not being treated with respect or dignity, the second was being prevented from making an impact in an organization; third, not being listened to and fourth not being rewarded with more responsibility. Further research has also concluded that why employees jump from one company to another is nothing different from the military. As ship captain, Michael knows that he can’t hand out pay rises, but what he did on his two years onboard the ship was to concentrate on dealing with unhappy sailors’ top four issues. Michael turned out to be quite a good ‘chess player’ by understanding the strength of each person.

In order to play chess, you must recognize the unique role each player on the team can fill. This means we must identify at least four qualities in others.

1. Understand the strengths and weaknesses

Identifying your people strengths and weaknesses is the first step in increasing efficiency at work. Not everyone will operate at the same strength in a certain skill. The best leaders know how to position their people for success and utilize their skills. If a person is good in leadership, then devise ways to give them more project leadership roles or opportunities for them to mentor someone junior. Evaluate your people’s weaknesses as well. Consider factors such as communication problems, lack of enthusiasm or poor comprehension of materials. Work with them and set measurable goals that they can be accountable for.

2. Motivation

Leaders need to find out what motivates their people. You may call it the trigger point for each person. The triggers that motivate people to achieve is different from everyone. Leaders must hold themselves accountable to build a purposeful and meaningful relationship that matters to their people. This allows us to better understand those we are serving, just as much as ourselves. Is it encouragement or verbal praise? Or is it affirmation? Everybody has a trigger that gets them motivated and ready to give themselves to the cause.

3. Personality

Understanding the personality of people is extremely useful in a relationship. There are many personality assessments to measure this such as the Brigg Myers Test or the DISC personality test. For example, using personality tests in the workplace help the employer to understand their employees as individuals and as a team. When used effectively, these tests increase productivity, teamwork and communication, leading to a happier and more profitable business.

4. Learning Style

Finally, leaders need to understand their people learning style. Are they and ‘Analyzer’ who craves information? Or are they the ‘Doer’ who has to get their ‘hands dirty’ and jump in to execute a task? Or are they the ‘Watcher’ who wants to see it executed first before they can progress?

Capitalizing on each person’s strengths accomplishes so many things for a leader. A mediocre leader believes value must be taught. But an excellent leader believes that the best is already inside of people and their job is to find it. So the question is what type of leader are you?

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Eric Chow

Passionate about leadership, self learning, data story telling, big data and predictive modelling.