How Chess Prepared Me to Be a CEO
Grow Your Business, Not Your Inbox
Chess has been loaded with a variety of ascribed “meanings” over time -- war training, intellectual self-improvement, moral righteousness -- but at its core chess is an enduring game of strategy. My family has played this game for generations, and in this inheritance are lessons I apply to business leadership to this day. There are analogs to many of the most critical concerns of a CEO -- including people, strategy and adaptation -- in the ancient game of chess.
Every piece serves a purpose.
In chess, you start the game with a set of pieces, from king to pawns, each with their own ability and position. 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. Pawns are moved into lattices that entrap knights, rooks are held back to support a castle at the most opportune time and bishops coordinate with the queen to flank the king. Every piece plays its part, and every piece is necessary.
It is a common folly of young business leaders to only be concerned with hiring “the best people,” defined in a fairly narrow way. Don’t just look for the “rockstars” or the “culture fits ” when building a team. Also look for the helpers, the testers, the maximizers and the culture adds. Combine senior and junior staff, knowing that junior staff give your senior staff leverage and force them to hone their craft by coaching others. Make sure everyone knows what is expected, what role they play and what role others play so they can make best use of each other.
Winning is a goal, not a strategy.
The many possible paths your game can take is what makes both chess and business challenging. For that reason, it is not sufficient to say your strategy is “to win in X market” -- you must be clear about how.
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 analyze actions and their outcomes, combined with skilled pattern recognition, is what defines strategy. Chess players talk about “opening gambits” and “endgames” the way entrepreneurs talk about “seed stage” and “mature markets.” They understand the actions that bring initial success are not the same ones that will carry you through the end.
Knowing your strengths, knowing your weaknesses, knowing your opponent, you think through these many possible worlds and design an approach that’s likely to win. Will you play aggressively or defensively? Will you push for short gains, or play for long term advantage? What will you do when you run into challenges along the way? Your strategy -- a combination of your goal and your approach for achieving that goal -- will direct and coordinate your actions, as both a CEO and a chess player.
Related: Learning to Think Ahead
Play the board, not the plan.
When playing chess your opponent is trying to predict, and undermine, your plan. So, in chess, as in business, your competition is applying their own strategy to capture more pieces, more customers, more market share, than you. So, what do you do?
I once had a boss tell me his approach was to “plan the work, and work the plan.” This approach attempts to predict every requirement, action, work package and hour of effort, in an attempt to give business owners comfort about their investment into the future. Time and again, this approach has been proven inferior, however, to agile methods which focus instead on making progress in a direction of travel and the ability to “pivot” in the face of new or changing conditions along the way.
I instituted these methods for the first time soon after this former boss left the business and I took his position. It fit naturally into my chess-playing brain. I could deliver business value often, but my teams could quickly outmaneuver competitors 100x our size and win. It was a revelation.
While planning is important, it should be a constant application of your strategy to real world circumstances, not a static activity that results in a rigid, doomed-to-fail set of tasks. Your competitors are constantly adjusting to you and the market. The winner will be the player who adapts soonest and most effectively.
Pause to reflect.
The core elements I’ve described -- people, strategy, adaptation -- are crucial skills for every successful entrepreneur. But I would be remiss if I didn’t mention one last thing that chess taught me: the importance of taking time for reflection.
It’s in reflection that the brain has time to learn, to process new information, to form memories, to recognize patterns. The time spent between games is as important as the time spent in them. That’s why successful entrepreneurs are not only hard workers, but avid readers, meditators, students and craftspeople. They don’t just do the work, they take time to think about the work and to better themselves as a consequence. The time you take to reflect on your team and your way forward will pay dividends.