“This is chess, not checkers.”

It’s an expression that feels as if it has been around forever. In practice, its first widely documented usage appears in the 2001 film Training Day, delivered with memorable force by Denzel Washington. But the metaphorical weight behind it reaches much further back. As early as 1786, Benjamin Franklin used chess to illustrate foresight and moral deliberation, and by the mid-nineteenth century writers were already employing chess imagery to describe complex social and strategic relationships. In the twentieth century, diplomats and commentators openly likened international affairs to grandmaster play. The modern idiom elegantly crystallizes a very old idea — some contexts reward instinct and quick reaction, while others demand patience, experience, and long-range thinking. That distinction is not theoretical; it reveals itself most clearly in business transitions.

For most business owners, day-to-day leadership feels closer to checkers. The pace is quick, the problems are familiar, and decisions are made as issues arise. In contrast, a business transition — whether a generational handoff, a third-party sale, or something in between — operates on an entirely different plane. It requires a deliberate sequence, a structured approach, and an awareness of how early choices may reverberate later in the process. In that sense, owners stepping into a transition often discover they have entered a chess match — and that the other side has usually played many more games. 

In working with owners through these moments over many years, three consistent themes have emerged:

Seeing the Board.

Many owners approach a transition as a series of regimented decisions because day-to-day leadership trains them to think sequentially. The institutions and professionals across the table rarely view those decisions in isolation. Their thinking is more integrated. They understand how a disclosure made today influences the position they will hold tomorrow. They anticipate emotional reactions, timing pressures, and the subtle ways first-time transition participants reveal more than they intend. What feels like a single move to an owner is often just one square in a much larger design to a more experienced counterparty. Without seasoned guidance, the owner responds one step at a time while the other side is already mapping the endgame.

Leveraging the Pieces.

One of the defining differences between the two games is that every checker moves the same way, while every chess piece serves a distinct purpose. Owners often assume that the professional advisors who have served the company well for many years will also be central in a transition. It is an understandable instinct, but it can reflect checkers thinking. Transition-driven legal analysis, tax structuring, accounting readiness, and process leadership each require distinct forms of expertise. The real advantage comes from retaining and coordinating specialists who know their lanes and understand how their work supports the broader strategy. Treating all advisors as interchangeable — expecting them to “move the same way” — is a checkers-minded mistake that can meaningfully affect outcomes.

Knowing the Moves.

Chess players do not win because they calculate every move from scratch. They win because they have internalized patterns — configurations that signal danger, opportunity, or subtle shifts in advantage. Experienced professional advisors carry a similar pattern memory. They know how certain transition issues tend to evolve, how diligence requests are sometimes used as leverage, and how timing pressures can be engineered in ways that lead to avoidable concessions. Very few first-time transition participants possess these instincts. They belong to those who have lived through both smooth closings and hard lessons, and who understand not only how the pieces move, but how the game usually unfolds.