The article addresses a class of managerial errors that are not the result of low qualifications, professional incompetence, or malicious intent. These are errors of value blindness: a decision flawless from the standpoint of numbers, instructions, and formal procedures, destroys people’s lives, ecology, and social communities, while the manager who made the decision sincerely does not understand «what went wrong» because no one has ever taught them to ask the question «Why?» Drawing on cultural-historical psychology (L.S. Vygotsky’s distinction between meaning and personal sense, A.N. Leontiev’s concept of sense-forming motive), G.P. Shchedrovitsky’s theory of mental activity (reflection as a position emerging in communication), B.D. Elkonin’s concept of the educational event (a turning point after which it is impossible to think as before), and the concept of anthropopractices by P.G. Shchedrovitsky and A.G. Asmolov (choice situations without instructions), the article introduces the concept of value reflection as the manager’s ability to halt the automatism of action, recognize one’s own value foundations, and hold alternative value logics. Drawing also on C. Barnard’s classical theory of management, the author shows that the problem of value regulation has a long tradition but has no systemic solution in education. Based on the analysis of 12 educational cases with future managers, it is demonstrated that value reflection is not formed through the transmission of ethical norms and codes. It is born only in situations of a «reflexive gap» — a value conflict without a correct answer, where a person is forced to publicly name their values and confront an Other who has chosen differently. For educational policy, this implies a shift from declarative «value formation» to the design of anthropopractices of value self-determination — and, more broadly, from the paradigm of competencies to the paradigm of subjectivity.