Anticipatory Thinking

A cognitive skill from military psychology, and what it means for foresight

Anticipatory Thinking is Gary Klein’s term. He developed it around 2007,¹ working with military professionals, firefighters, and emergency responders: people making consequential decisions in fast-moving situations where prediction is impossible. The question he was trying to answer was what experts actually do when they prepare for futures they can’t predict.

The answer turned out to involve three distinct mental moves.

Pattern matching

Experts read the present against a library of past situations. This isn’t calculation or forecasting. It’s recognition. A firefighter entering a burning building isn’t running a simulation. She’s asking, consciously or not, what this smoke pattern has meant before, and whether what she’s seeing fits. The signal that something is off, that a building is about to collapse, comes from a mismatch between current observations and the mental model her experience has built.

Trajectory tracking

Rather than fixing on a single expected future, practiced anticipators keep watching how a situation is moving: where the momentum is, what rate of change suggests about what comes next. The focus is direction, not endpoints. A sail trimmer isn’t asking where the wind will be in an hour. She’s reading what the water and the clouds and the boat’s feel are suggesting about the next few minutes.

Conditional thinking

Klein calls this prospective branching: if this happens and that develops, then probably this. The lineage runs back to Adriaan deGroot’s 1946 chess studies,² which Klein cites as a foundational influence. A grandmaster considering her next move isn’t picking the best line she can see. She’s holding several forward at once: if I push the pawn here, the center opens but my king weakens; if I castle now, I lose tempo but gain safety; if my opponent ignores the threat, the advantage compounds three moves out. She holds multiple linked chains in mind without committing to any of them. The question isn’t “what will happen” but “what are the linked consequences of what’s already in motion.”

Foresight is methodological and organizational: it gives teams and institutions structured ways to explore uncertainty together. Anticipatory Thinking is cognitive and individual. It’s the mental capacity that makes a practitioner good at foresight in the first place.

This distinction has practical weight. Good methodology doesn’t compensate for thin anticipation. Scenario workshops produce clean outputs from any group; what changes is whether anyone in the room can read those outputs back into a coherent picture of how the world might actually move. The methodology delivers the format. Anticipatory Thinking delivers the reading that fills it.

One is a practice. The other is what you bring to it.

Connections

OODA Loop — closest conceptual cousin. Boyd’s Orient phase is, in a sense, Anticipatory Thinking applied to real-time decisions. Both frameworks emerged from high-stakes operational contexts, and both center on the quality of mental models rather than the speed of prediction.

Risk and Uncertainty — AT operates in Frank Knight’s territory of genuine uncertainty. Klein’s framing of it as “future-oriented sensemaking” connects directly to Weick’s sensemaking, which comes up in that note.

Scenario Planning — Pierre Wack described scenario work at Shell as “the gentle art of re-perceiving.” Anticipatory Thinking is the individual cognitive correlate: the capacity that lets a practitioner re-perceive in the first place.

The paradox of foresight — adjacent observation about why anticipation is structurally hard to institutionalize. The paradox names the organizational version. Anticipatory Thinking sits one level below: the individual capacity that makes anticipation work in the first place.