Through the use of grounded theory methodology and the operationalization of a representative bureaucracy framework, this study investigates the perception of discretion within public administration in educational institutions. Public administrative actors use discretion to provide equitable learning opportunities, and without said discretion, underrepresented groups would have no extra support despite numerous disadvantages. In an attempt to give cause or further explanation as to the nature of this discretion, evidence from 20 interviews and 30 hours of observation of fifth grade classrooms in urbanized schools (n = 8) suggests a grounded theory of purposeful accountability to link an increased perception of discretion for teachers and principals. School officials can stay afloat in the age of accountability as long as their sense of belonging and ability to mobilize their organizations are maintained through proper access to centralized knowledge and expectations, the ability to fulfill needs unique to the organization, and the recognition of efforts and status through trust from centralized authority. With this theoretical foundation, public administrative actors can find greater progress and efficiency in assuring active representation through discretion.