Academics and lay persons alike freely acknowledge that principals exert enormous influence over the creation, maintenance and enhancement of the learning environment in schools. They recognise that a turbulent educational world presents principals with multiple challenges in sustaining the conditions necessary for student achievement, and that some principals are more successful in this endeavour than others. This small-scale qualitative study uses a semi-structured interview process to gather data from five Chairpersons of Boards of Trustees who have appointed a principal within the preceding twelve months. The study discusses the professional capabilities that theoretical and empirical research suggests distinguish highly effective principals from capable performers. It adopts a bipartite approach to the literature, examining both academic understandings and the degree to which available official publications inform the thinking of Boards of Trustees prior to embarking on the principal appointment process. The study then explores the extent to which these understandings influence the decision-making of five Boards of Trustees in appointing a new principal. Research findings reveal a dichotomy between the theory underpinning concepts of highly effective principals and the practice of Boards of Trustees in appointing a principal. Largely unaware of the academic literature and inadequately informed by official publications, Boards of Trustees adopt a problematic generic recruitment and selection process. Uncritical acceptance of the professional knowledge and standing of external consultants and misplaced trust in the advice they proffer leads Boards to proceed on a questionable perceptual basis. Secure in the knowledge that they have obtained the educational expertise they freely acknowledge they lack, Boards are further exposed to prevailing market discourses and internal prejudices which undermine their ability to identify and appoint a principal who possesses the capabilities necessary to exercise highly effective, contextually specific leadership. This study suggests that the autonomy of Boards of Trustees in their role as employer be sustained but supported through the mandatory appointment of an appropriately qualified advisor and that the involvement of existing advisors be further scrutinized.