Philosophers of education may imagine their work has great relevance to people trying to lead K-12 schools. In the current context, it would seem philosophers of education are sorely needed. Standardized assessments maintain their hold on curriculum and instruction, differentially affecting schools whether they are the targets of accountability programs (who can never quite achieve the test score results to avoid being targeted for takeover or replacement) or the competitive winners (who have to repeat their test score dominance in perpetuity, lest they lose public support). Added to those struggles are the political backlash against long-deferred efforts to address issues of equity, inclusion, and racial justice. Pennsylvania is not Florida, but parts might as well be. In the area where the author lives, some districts have forbidden instruction in diversity, equity, and inclusion (DEI) or removed library books in response to parent complaints. Nearly all school leaders in the area are facing some degree of backlash from parents and/or their school boards as they attempt to address educational inequities in their schools. Considering the pressures that school leaders face for test score accountability and constraints on their equity practice, the author argues that philosophers have an important role to play in thinking with school leaders about how best to respond to largely individualistic pressures for standardized practice. In this paper, the author names some underlying philosophical concerns that are at issue and address ways leaders can identify their core commitments, stand strong in the face of pressures, and work toward greater collective responsibility for more equitable and liberatory educational opportunities for students.