Mind The Gap When Evaluating Strategy

Every governing board makes strategic decisions amid uncertainty. That's not a flaw in the process — it is the core nature of strategic work. Boards approve plans, allocate resources, and set institutional direction based on what they believe will happen, not what they know will happen. Handling the gap between those two is where governance becomes interesting—and where it can go wrong.

There is a useful concept from economics and decision theory that deserves more attention in boardrooms: the distinction between ex ante and ex post reasoning. Ex ante—literally "before the event" — describes the perspective from which every strategic decision is actually made. Ex post—"after the event"—is the lens through which those decisions are almost always judged.

The information mismatch between ex post and ex ante information creates real governance problems. A decision can be excellent ex ante—made with thorough analysis, sound reasoning, and appropriate risk assessment—and still yield a poor outcome due to unforeseeable circumstances. Conversely, a reckless decision can luck into a good result. Governing boards should evaluate themselves and school leadership based on the soundness of their ex-ante reasoning, not just ex post results.

Boards that conflate decision quality with outcome quality will punish good thinking that encountered bad luck and reward poor thinking that happened to work out. Over time, this erodes trust between boards and heads of school, distorts institutional risk tolerance, and produces strategic plans that are more about political cover than genuine foresight.

Every strategic plan necessarily rests on ex ante assumptions about the future environment. No amount of data can eliminate that fact. Good planning makes its assumptions about the future explicit and testable, building in checkpoints where the board and leadership can compare ex ante projections against ex post reality and adjust course. This creates accountability, enables genuine learning when outcomes diverge from expectations, and protects against hindsight bias—the human tendency to judge past decisions based on information that was not available at the time.