You are currently viewing Business Strategy Lessons We Can Learn From Chess

Business Strategy Lessons We Can Learn From Chess

A few weeks ago, VBN and friends partook in a friendly chess tournament to build camaraderie, take the edge off of the lockdown, and most importantly have fun. Chess is a very rewarding and intellectually stimulating pastime, it can be relaxing or competitive depending on how it is played, and you can meet great people in the games. And it is more than just a game, it can teach life lessons that can be applied in a lot of situations like business strategy.

Time To Play The Game

While the games are friendly, the actual dynamics of chess is far from it. After all, the board is a battleground and the enemy has to be beaten at all cost if you want to win. You must sacrifice your pieces in order to meet your ends, and there are only a finite amount of them.  It’s much like being a CEO of a company, or the head of a startup. Bringing your company to success is much like winning a game of chess. Of course, you aren’t going to sacrifice your employees to enemy Rooks or Bishops and your Virtual Assistants won’t be defeating Pawns. Still, business strategy entails planning three moves ahead or more, executing stratagems, even making sacrifices in terms of budget or profit for the sake of a greater goal. 

Chess, Life Lessons and Business Strategy with Gary Kasparov

The game is so relevant that Harvard Business Review interviewed none other than Gary Kasparov regarding his experiences with chess and the lessons it can offer entrepreneurs. For those who are unfamiliar, Kasparov is a renowned chess master, a champion, and won several games with IBM Deep Blue supercomputers. So he’s a smart guy. And he has the following tips:

Never Underestimate Opponents

In chess, always assume that the opponent will see through your strategy and devise a counter. In business, this means be prepared for competitors to circumvent your plans. But in business, opponents can include factors that are beyond human – like the circumstances of the market, or unexpected pandemics that upturn the world economy. So factor in parties or events that might mess up your strategy and plan accordingly, have a Plan B or even a Plan C that will allow you to accomplish your aims even if your initial approach has been anticipated and compromised.

Get Comfortable in Enemy Territory

You won’t always have the home court advantage. Sometimes, you won’t be facing an out of town or overseas competitor budging into your turf. You might be the one expanding into someone else’s territory or industry. In these cases, you will be expected to be hesitant and cautious. Convincing them that you are comfortable will then upset their plans and make THEM the ones who are uncomfortable, turning the tables so that they will be in YOUR turf.   In the case of COVID-19, “enemy territory” entails market conditions utterly upturned by the pandemic. Businesses that pivoted to eCommerce, online sales, pickup and delivery services conveyed their confidence. And they found a way to bounce back despite the difficulties they experienced. Some businesses that adapted even seem like they are doing better than before, whereas other less agile operations aren’t adapting well and are far worse off.

Showing Uncertainty

Similarly, be careful with how you act. Whether through the way your business conveys its plans or how you yourself act in front of others. You may betray a lack of confidence that might get exploited by opponents. Or it might give investors or potential partners and clients doubts. Knowing this, you can prepare yourself better and conceal weaknesses. This way, competitors will not detect weaknesses, investors and partners will remain confident. So, with your excellent poker face, you will be better able to execute your plans. 

Detail and Operations

Kasparov delineates two types of people, those who are good in scrutinizing details and those who have a broader perspective. You want managers who are outstanding in solving small problems – the kinks of the finer inner workings. While those who look at the bigger picture can be assigned to leadership positions where their gifts will be maximized. 

Intuition is In

Kasparov also says that in the toughest times, you need to rely on your gut to make it out of these tight situations. By intuitively devising the best and most innovative moves or simply making the right decisions. This gut instinct doesn’t come out of nowhere. It is developed from experiences and lessons that are internalized, that we have absorbed so deeply that it becomes almost reflexive. Like those situations when there’s no time to think about things consciously. Experienced people make snap decisions that ultimately turn out for the best. This is definitely an asset when it comes to executing business strategy. We have to be prepared for any outcome, after all. 


Spending time playing chess is more than just a pleasant reprieve. It also helps increase concentration and sharpens the mind, which business leaders – and anyone, really – will find most useful. We live in a world full of distractions, where the quick pace of work prevents us from sitting down and contemplating matters deeper. Moreover, chess also helps build confidence, memory and mental capacity. Winning is a definite ego boost, but more importantly, one can learn even more from losing and continuing on. With perseverance, win or lose one gradually masters one’s abilities. And this will lead to greater wins and ultimate success in the game and life as well. So how about we stay sharp with a game of chess?