<p>In Sweden, the principal is tasked with ensuring fair and equitable grading, yet the discretion and mandate for the act of grading are entrusted to the teacher. This situation entails a potential teacher-principal conflict, and principals must thus determine how they will exercise leadership in terms of grading and assessment practices. To investigate this dynamic, we employ a critical approach that invokes literature on the sociology of professions, and argue that principals have one foot in the teaching profession (occupational professionalism) and the other foot in the managerial profession (organisational professionalism). The aim of the current paper is to investigate principals’ leadership practices in situations of grading and assessment under the lenses of both organisational professionalism and occupational professionalism. The analysed data were collected from two group interviews with principals that covered their perceptions of grading and assessment. The leadership practices expressed by the principals were found to include aspects of both organisational and occupational professionalism. Thus, even though the professionalisation of Swedish principals is strongly influenced by a macro level discourse related to organisational professionalism, our findings show that, at the micro level, the occupational professionalism discourse is also prevalent. In an attempt to move beyond a dichotomisation of the two professional discourses, it is suggested that principals’ leadership practices regarding grading and assessment are best understood in terms of hybrid practices.</p>