This discussion paper draws on cultural anthropology, narratology and rhetorical analysis to offer a conceptual analysis of the practice of higher education engagement. It is argued that authentic engagement is a counter-intuitive practice that calls prevailing forms of knowledge, indeed the wider status quo, into question.  This analysis is correlated with literature from the field of adaptive leadership studies to illustrate the types of disruptive challenges engagement work seeks to both provoke and mediate.  Predictable forms of personal and organizational resistance, designed to restore systemic equilibrium, are indicated and questions are posed regarding how higher educational institution might better operationalize practices that straddle the need to guard prized cultural traditions while putting existing forms of knowledge and practice in question.