AI systems increasingly enter organizations through policies, procedures, playbooks, prompts, and other explicit representations of work. Yet formal descriptions often differ from situated practice, and captured know-what can omit the contextual know-how experts use when judgments are uncertain. We argue that a recurring class of organizational AI failures arises partly from a knowledge representation problem at the sociotechnical interface: the AI receives the procedure, while the organization operates on the procedure plus negative boundaries, runtime judgments, responsibility assignments, and learning history. We introduce O-I-B-A-R (OPEN, IS, BUT, ACTION, RESULT), a scaffold for externalizing these missing decision boundaries. IS records when a judgment holds. BUT records a concrete failure containing information beyond the logical negation of IS. Comparable success and failure cases are decomposed toward a minimally sufficient changing variable, which becomes a value-bearing decision dimension. A suspension represents the state in which the dimension is known but its current value is unresolved, specifying what must be measured, asked, retrieved, or escalated to a human. RESULT confirms a boundary, shifts a threshold, or exposes a new dimension. Incidents can generate new dimensions, unresolved values can define human-AI handoffs, and feedback can expand the decision space. We also identify a sociotechnical tension: durable and attributable failure histories can suppress the candor on which useful boundary knowledge depends. Externalization must therefore be designed as an organizational intervention with real costs and incentives.

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