Chess

I was in the chess club in high school. (Nerd alert, I was also in J.E.T.S.—Junior Engineering and Technology Society—and the computer club.) I liked playing chess because it required me to think as many moves ahead as possible and to adapt my strategy as my opponent made their moves.

Life is like chess. That’s a broad claim, so let’s narrow the field a little and go with, “Leadership is like chess.”

In chess, every move creates possibilities and eliminates others. Move a pawn, and new possibilities open while others disappear. Move a knight, and the bishop’s diagonal shifts. Nothing happens in isolation. The board is a connected system where each decision ripples forward, shaping what moves become available later.

Leadership works the same way. The decisions we make today don’t just solve today’s problems. They create the landscape our teams will navigate tomorrow. Hire this person instead of that one, and you’ve altered what projects become possible next year. Prioritize this initiative over that one, and you’ve determined which skills your organization will develop and which will atrophy.

Great chess players don’t just look at what’s immediately in front of them. They’re calculating sequences, asking, “If I do this, then they’ll do that, which means I can do this other thing, which sets up an opportunity several moves from now.” They’re thinking strategically and planning as far ahead as complexity allows, knowing every choice compounds.

Leadership carries the same responsibility. We need to think multiple moves ahead. We need to understand that every decision is either building the future we want or undermining it. And more importantly, we need to create environments where our teams can think this way too. Because if we’re the only ones playing chess while everyone else is just reacting to whatever piece is in front of them, we’re going to lose.

So, what gets in the way? What keeps us and our teams from thinking strategically?

First, survival mode. When people are scrambling to keep their heads above water, they can’t plan ahead. They’re in pure reaction mode—every ounce of energy going toward making it through today. This is why creating psychological safety and manageable workloads isn’t just nice leadership; it’s strategically essential. People who feel constantly threatened or overwhelmed struggle to think creatively or strategically. That’s how the brain works under chronic stress.

Second, short-term pressure. When everything is measured quarterly and leaders get rewarded for hitting immediate numbers, the incentive structure works against strategic thinking. Why would anyone sacrifice this quarter’s results for next year’s potential? The system punishes that kind of thinking. So, we optimize for the next earnings call instead of the next decade, and we wonder why we keep getting blindsided by changes we should have seen coming.

Third, lack of clarity about where we’re going. If people don’t know what winning looks like, they can’t plan moves toward it. Imagine trying to play chess without knowing whether you’re trying to checkmate the king, capture the most pieces, or control the center. You’d be paralyzed. Leaders who fail to articulate a clear vision aren’t merely failing to inspire. They’re making strategic thinking impossible.

There’s a recovery angle here worth mentioning. Addiction is fundamentally about immediate gratification overriding long-term thinking. The substance or behavior promises immediate relief, and that relief becomes so overwhelming that future consequences become invisible. Recovery requires relearning how to think strategically about your own life—how to make choices today that build toward the person you want to be tomorrow. It’s the same muscle organizations need.

Leaders have two critical responsibilities. First, we have to do our own strategic thinking work. We can’t outsource this. We have to hold complexity, see connections, imagine multiple futures, and plan accordingly. If we’re not capable of strategic thinking ourselves, we can’t cultivate it in others.

Second, we have to protect our teams from the barriers that prevent strategic thinking. This means creating stability so people aren’t in constant survival mode. It means pushing back against short-term pressure when it threatens long-term health. It means communicating vision clearly and consistently. It means rewarding people who think ahead, who ask hard questions about consequences, and who consider second- and third-order effects.

Not doing this work is like playing chess without strategy. You’re just moving pieces when they’re threatened, reacting to whatever your opponent does, and never setting up anything intentional. And when you play that way, you lose. Every time. Not because you don’t care, but because chess doesn’t reward short-term thinking. Neither does leadership.

The best chess players don’t win because they are smarter than everyone else. They win because they consistently think one move farther ahead. Leadership is no different. The board is connected. The moves compound. What we do now shapes what becomes possible later. Leaders who understand this—who think strategically and build cultures that reward strategic thinking—don’t just survive change. They position themselves to thrive in it. That’s the Bison Way.