What chess taught me about design
I had just begun my job at a large, shiny design agency; new people, new clients, new scale of work. Though I had plenty of work experience, I was outside of my comfort zone. One of the first impressions I recall is simply how confident everybody seemed as they sped to and fro between meetings, wall critiques and co-working sessions. Everybody seemed to know exactly what they were doing and I had so much catching up to do. In the proud tradition of so many before me, I had fallen victim to that classic notion of imposter syndrome.
Then one day I found an old chessboard in a closet during some routine cleaning. In a moment of magical thinking I connected the two: If I can deconstruct, learn and get comfortable with something as complex as chess, maybe I can apply that confidence and that analytical thinking to my new environs. Maybe this will be good exercise.
Many people feel intimidated by chess as a result of its complexity and overwhelming potential. A fresh board is like a blank canvas. You can read the rules in minutes, yet somehow it feels like an unscalable mountain viewed from the ground. To add, our experience of viewing chess is usually accompanied by a demonstration of mastery: We see old fossils in public spaces, calculating and conniving against each other; sometimes playing a few games at once. They seem to picture the whole game in their mind’s eye. Surely one must be a prodigy to play this game. Not exactly true.
As with any craft, practice helps. But chess, as I would come to learn, is not exclusively the province of the genius and nobody (not even the fossils in the park) can picture a whole game in their mind. Like the design process, there’s often a narrative arc at work; patterns to recognize and learn from as you skill up. Here are several big ideas about chess that I’ve observed over the last year and what they would come to reinforce for me about the design process.
A story in three acts.
A whole game of chess breaks down neatly into 3 acts. The opening moves are when each player develops their minor pieces, moving them out onto ‘active’ squares and trying to get a foothold in the center. In the middle game, each player begins thinking of a high-level strategy (based on how the opening panned out) and looking for moves that begin implementing it. In the end game, each player goes in for the kill, making the best use of the position they find themselves in, to try and trap the opposing king. Proficiency in chess begins with an understanding of what phase of the game you’re in, which informs how you should be thinking and behaving.
It’s not unlike the design process in that it can be understood in phases. Depending on how you work, there is usually some kind of discovery/empathy phase followed by defining your problem more concretely, ideating through solutions and ultimately prototyping, testing and refining them. Smart, efficient work comes from respecting which phase of the process you’re in. Diving too deep into implementation details while you’re still in discovery is not productive. This is an urge I’m always trying to resist. At the same time, one must sense the appropriate time to stop researching and begin committing ideas to paper. Generally speaking, both chess and design are scenarios where the path to victory isn’t apparent until you’re at least past the first “phase”. Nobody is brilliant enough to divine the final result early on.
Every move is an investment.
The decisions of a chess game’s opening moves can be thought of as investments. Pieces are marched forward and other pieces follow behind to support and defend them. Often, during the first two phases, one makes a move that poses no immediate threat or captures no enemy piece. The hope is that the move simply strengthens your position. When good investments are made early, opportunities for interesting attacks aren’t created but discovered. They reveal themselves, as time moves forward. And one can never be completely certain about exactly which early-game move will turn out to be the most critical one in the game.
I’ve kept this idea of “investments” in mind at the early stages of every project. When the nature of a project is still ambiguous, discovery can feel a lot like the opening moves, when it’s not yet clear how your investments will pay off. Imagine you have one hour with a stakeholder, subject matter expert, or user. This can feel particularly apropos when you’re trying to artfully select which questions to ask– when you don’t even know what you don’t know. And even after a research period, one can never be sure which exact insight or quote will turn out being the watershed detail that validates your final design. Every detail matters.
Like controlling the center of the chessboard, some investments always seem to pay off: Doing competitive research early, for example, provides value throughout the entire process. Or in the case of a redesign, deliverables like a site-map or content audit of the existing product can wind up being a valuable reference or teaching tool when working with stakeholders in later stages.
Strategy vs. Tactics.
In any game, there’s a crucial difference between strategy and tactics. Tactics are actions that attack your opponent, limit their options or force their hand. The check, the pin, the fork. They’re the tools in your belt. The benefits of a strategy take longer to unfold and are more ambiguous. You might think of the difference as high-level vs. low-level thinking. When evaluating what move to make next, you might scan for a tactic that benefits your plans. If none exist, you can always shortlist a few moves that will strengthen your position overall or pivot you into a new strategy if needed. A player shifts between tactical and strategic moves that affect one another. This is referred to as positional play and it’s the thought process that people who look like chess geniuses are going through when they walk by one of the 5 games they’re simultaneously playing, quickly scan the board, and make a casual move. If your opponent’s tactics affect your play, then you simply must adapt and try something new. Tactics affect your strategy and support it as it shifts and plays out.
I’ve found that in the design process, a strategy (concept, approach, product story) is a living thing that exists outside of ideals and must bend to the physics of the real world. A discovered technical limitation, an internal “debate” amongst your stakeholders, a shift in the competitive space of your product– These things may suddenly impact your entire concept. In these moments, when you’re deciding what move to make next, the differences between high and low-level thinking is important to consider. Is another iteration of your idea what’s really needed now? Or do you need a workshop with stakeholders to get realigned? Is it time to obsess over color choices? Or do you need to further refine the story of your product? Usually–as in chess–there’s no perfect waterfall from concept to execution in two steps. Instead imagine a pendulum that swings back and forth between concepting and sitting down to actually execute the work. Eventually (and ideally) the back-and-forth between strategic and tactical thinking will settle you on an outcome. Our work time is a precious and limited commodity so knowing when to shift between strategic and tactical work is an important skill that we’re all trying to improve.
Why chess?
I have a very metaphorical way of thinking. I like to make connections between processes that feel similar. Oftentimes our work is ambiguous. On kickoff day of a new project, the world of possibilities can sometimes feel paralyzing. Like observing the chess master in the park, it’s tempting for me to think that everybody else constantly knows exactly what they’re doing and where they’re heading. That pesky imposter syndrome rears its ugly head as a result.
Learning about chess improved my confidence. It wasn’t just a safe space to exercise analytical thinking. It also helped me see that complex problems can feel less frightening the more you learn about their typical arc; as you start to recognize and remember patterns. And most importantly, it reinforced that process is often more important than result.
You don’t need to be a genius. You don’t always need to know exactly what to do from the very start. An endgame is always achievable, and successful or not, the process will be revealing and will improve your next game.
The views expressed in this post are that of the authors and may not reflect the views of the agency or company.
