How playing chess improves your startup game

Underlying a game of chess is an abstract structure of rules and relative powers, which can be quite mind-boggling. The game emerged in C5th India, but it wasn’t until the C19th, when the set was standardised into the Staunton version we play today.

To follow a professional game is to get lost in algebraic options and notations. When the 13-year-old Bobby Fischer sacrificed his queen against Donald Byrne in the so-called ‘game of the century’ in 1956, it was considered one of the finest moves in chess history – a greatness not quite communicated by Be6.

Chess is an endless pursuit, a game of longevity with logical consequences and sly entrapment. After sacrificing his queen, another 24 moves later, Fischer won – a result, he’d worked out, that was inevitable if he let his queen go. It was sacrifice that was also attack, aggression that was also composure.

When a chess player looks at the board, he does not see a static mosaic of contrasting, patterned squares, but a magnetic field of forces, charged with energy, potential and intrigue. A game of chess opens in a state of balanced equilibrium, and if the optimal move is made with each play, a draw is all but assured.

Norwegian Sven Magnus Øen Carlsen is the current World Chess Champion, holding the title since 2013. His peak Elo rating – the ratings given to chess players corresponding to their performance over the best five-year span of their career – of 2882, achieved in 2014, is the highest in history, ahead of Gary Kasparov at 2851.

Magnus tries to put the accent on play, less on preparation, and is seen as combining the talents of two of the all time greats, Karpov and Fischer. He’s known for getting his positions then holding on with a bulldog bite. Exhausting for opponents, one of his most feared qualities is his ‘nettlesomeness’ – his creative moves pressurise opponents into mistakes. Carlsen’s endgame prowess has been described as among the greatest in history.

The last World Chess Championship in 2018 began with a series of twelve games played under classical time controls, the traditional slow pace of play. Carlsen failed to win a single one of his contests against the challenger, American Fabiano Caruana, but fortunately for the Norwegian, Caruana never reached a checkmate or extracted a resignation either.

With each of the dozen classical games ending in a draw, the match moved to a series of faster-paced tiebreakers, starting with a series of four ‘rapid’ games, in which players are allotted less than one-quarter the thinking time of the classical format. Carlsen, the stronger competitor in speedier formats, won the first three games to clinch the tiebreaker and retain his title.

To the casual observer, three weeks of drawn games may sound excruciatingly boring, but like a football match with smart, impregnable defences, or a baseball World Series studded with scoreless pitching duels, chess title matches feature two equally matched grandmasters competing at an extremely high level.

You start the game with a set of pieces, from king to pawns, each with their own ability and position, each has their own purpose. Novice players push forward immediately with their back row, trying to get their most valuable pieces into win positions early. Experienced players, however, know that it is the pattern of all their pieces working in concert that creates reliable success.

Master chess players see the unfolding patterns of the board over time, thinking not in terms of one piece or one move, but in terms of the entire board over dozens of moves. This ability to analyse actions and their outcomes, combined with skilled pattern recognition, is what defines strategy.

The objective is to play the board, not just your plan. When playing chess your opponent is trying to predict and undermine you, applying their own strategy to capture more pieces, so, what do you do?  One crucial skill is the importance of taking time for reflection. It’s in reflection that the brain has time to learn, to process new information, to recognise patterns, and recall previous successful moves.

I see many similarities between chess and running a startup business from the strategy, thinking and tactics behind the game. Let’s look at the lessons and learnings we can take from Carlsen and his Word Championship success.

The first phase in a chess game: the opening As Carlsen shows, the purpose of the opening isn’t just to get immediately ahead, rather it’s to set the stage for the type of middle game you want. This can also mean manoeuvring for the type of game your opponent doesn’t want. The openings are the only phase in which there is the possibility of unique application, you can find something that no one else has found.

Be first, and be brave is the lesson for a startup, but equally don’t rush. Aim to be bold, but have some thoughts around what the early stages of your business could look like. Of course, early encounters with customers reshapes your thinking, so be prepared to be flexible and respond to feedback.

The second phase: the middle game What sort of middle game is our opening going to lead to? Is it one we are prepared for or have our opponents out foxed us and we’re playing catch-up? We must also play the middle game with an eye on the endgame.

In a startup it’s important to have a strategy, tactics and a game plan thinking in periods initially of no more three months, with objectives and key milestones, things are just too volatile to plan too far ahead. As you navigate what it often a turbulent first phase, what you should be doing in the second phase will emerge. Continue with innovation at the core, but listen to customers.

Dream a little, don’t settle automatically for routine solutions The paradox of chess is that there is a routine set down by mathematics to make a strong move based on its objective merits. But recall Carlsen’s approach is a combination of freedom and discipline, sober evaluation and calculation mixed with outlandish ideas.

In a startup, you won’t find new ways of solving problems unless you look for them and experiment and have the nerve to try them when you find them, but ensure flair doesn’t mean or you spend your life making beautiful blunders.

The future is a result of the decisions you make in the present The strategist starts with a vision of the future and works backwards to the present. Carlsen makes the best moves because they are based on what he wants the board to look like ten or twenty moves ahead. This doesn’t require the calculation of countless twenty-move variations, but an evaluation where his fortunes lie in the position and establishes objectives.

Having a vision for your startup is just as important. Where do you want to be in three years? Make a start, and try to make every day a step in the right direction towards your horizon.

Intuition & analysis Even the most honed intuition can’t entirely do without analysis. Intuition is where it all comes together – our experience, knowledge and judgement – or even hunches. But it doesn’t matter how far ahead you see if you don’t understand what you are looking at before you, so combine the two.

No matter how much practice or experience you have, and how much you trust your gut instincts, analysis is essential. It’s a balance between inspiration and perspiration, blue sky thinking and washing the pots. It’s dreaming, plus hard yards.

Attack An attacking strategy doesn’t have to be all or nothing, or recklessly lightning quick. Sustained pressure can be very effective in chess, and creating long-term weaknesses in your opponent’s position can lead to a win in the long run. One of the qualities of a Carlsen is his ability to get the maximum out of a position without overstepping and trying to achieve more than what is possible.

In chess, the defender has to race around to cover the threats, but against constant pressure the job soon becomes impossible. Moving to cover one breach creates another until something cracks and the attack breaks through. In chess we have the ‘principle of two weaknesses’. It’s rare to be able to win a game with only a single point of attack. Instead of becoming fixated on one spot, we must exploit our pressure to provoke more weak spots.

So a large part of using the initiative in chess, as in business, is mobility, flexibility and diversion. In business, it’s a combination of product, service and price that creates a winning position, then execution and delivery that secures a deal.

Initiative Once you have the initiative you must exploit it. Carlsen reminds us that the player with the advantage is obliged to attack or his advantage will be lost. In business, initiative can be converted into a sustainable position. Being a step ahead means we can keep our competition off balance, shifting and moving in order to provoke weaknesses.

In business, going on the front-foot requires perfect timing as well as nerve. The window of opportunity is often very small, as with most dynamic situations. No neon sign appears to say that there is a big opportunity right around the corner, so balance opportunity with rationale – back to the combination of freedom and discipline in your game plan.

When you are winning, don’t get complacent Winning creates the illusion that everything is fine, success is seldom analysed as closely as failure and we are always quick to attribute our victories to superiority, rather than circumstance. When things are going well it is even more important to question. Over-confidence leads to mistakes, a feeling that anything is good enough. Our egos want to believe that we won brilliantly against tough competition, not that we were lucky and ‘right time, right place’, but typically, however, the winner is just the player who made the next-to-last mistake.

Carlsen shows that if we’re going to get the most out of our talent we have to be prepared to have a game plan, practice, think on the spot, analyse ourselves critically and improve our weakest points. The easiest thing is to rely on talent and focus only on what we do well. It’s true that you want to play to your strengths, but if there is too much of an imbalance growth is limited. In business, the fastest way to improve overall is to work on your total game, and all the constituent parts.

He highlights long-term strategy, short-term gains, being creative in the middle game, and how important decision-making is at any stage of the chess game. We do need to think ahead in business, if not for ten moves, but then at least truly think through options and the consequences – that’s not calculating, it’s common sense. Carlsen illustrates that the unlimited number of subtle and intricate potential moves that lie within the 64 squares of a chessboard are totally applicable to business, how the game can help you step back and evaluate yourself to identify you strengths and weaknesses and thus better your game.

Chess is a mental game, that requires vision, tenacity, thoughtfulness, and multiple tactics. From this we can take the thought that in a startup we can look for ways to experiment and to push the boundaries of our capacity in different areas. It really is a combination of disruptive and disciplined approaches, and agile thinking that will bring success.