As in other western market economies, New Zealand government education policy reflects neoliberal economic thinking, neo-conservative ideals and practices of an audit culture. New Zealand’s self-managing schools’ policy, introduced in 1989, changed significantly the complexity of school principals’ work. Leadership frameworks and professional standards have ‘captured’ this complexity and support appraisal of principals. Neoliberal/neoconservative thinking has also influenced educational leadership research by focusing on individual leader characteristics and specific cases of ‘successful’ school principalship. Instead in this study formative assessment research provides the lens to (re)consider appraisal experience of six school principals in small rural primary schools. Using a contemporary-pragmatist approach, interviews, abductive processes of analysis and literary forms of representation were chosen as appropriate research design elements. The research concern was: to what extent does principal appraisal recognise the nature and complexity of expectations of principal work in specific school settings and consider the human being undertaking this work? Insights from this study come under the umbrella phrase it is people that matter. Thus, appraisal in this study reflects the nature of principals’ work—in the significance of interaction, management and professional judgement—more than aspects of administration or assessment. Recommendations include: future appraisal policy values principal-appraiser interaction; principal preparation and professional development programmes advocate for the importance of self-care and management in principalship; and research further explores the nature and influence of school communities on principals’ decision-making and the judgement of principals’ work.