School leadership roles and responsibilities are changing, subsuming managerial expectations and increasing focus on the priorities of school-based collaboration, collective culture, and community engagement by seeking stakeholder consolation and trust. Ultimately, school leadership is now, more than ever, about pedagogical responsibility and relationality—the art and science of modeling effective practice in relation to teachers, learners, and the community. Changes in Alberta's Teaching Quality Standard (TQS) (Alberta Education, 2017b) from a checklist to that of a growth-focused continuum have necessitated an evolution of the supervision and evaluation practices by school leaders. Seemingly objective evaluation practices are no longer adequate for the determination of teacher ability relative to competencies and their indicators. By shifting evaluation and supervisory paradigms from the safe and objective toward the messy and dialogical it is possible for school leaders to better understand the interconnected and complex nature of teacher practice and identity. By enacting pedagogies of love as defined by bell hooks (2001) as a combination of care, commitment, knowledge, responsibility, respect, and trust it is possible to better understand teacher practice and pedagogy through a lens that provides the space for failure and struggles and ultimately growth and success—something stronger and more robust, something different that could not have been there before. It is the enactment of pedagogies of love that may allow for teacher personal and collective growth through relationality.