The dispositions of school leaders play an integral role in dismantling inequities that hinder the academic achievement of students, particularly students living in poverty. Recent studies bring to light the importance of an asset-based understanding of what children bring to the classroom and how to draw on these assets in creating opportunities for student success. A paradigm shift is taking place whereby school leaders must lead with equity as a foundational thought when assisting teachers in recognizing, valuing, and honoring the assets that students bring to the classroom. This paper attempts to discuss critical issues pertaining to educational equity by using related literature on the topics of poverty and transformative leadership as well as data collected from 15 participants consisting of administrators, teachers, parents, community members, and students who were interviewed in the study employing qualitative narrative inquiry. Additionally, it makes recommendations relative to the dispositions school leaders must employ, embrace, foster, and practice in addressing the social, cultural, and emotional needs of students to elicit and enhance effective engagement in school.