To develop transformative experiences, educators must meaningfully ground leadership development interventions in theories and models that reflect how leadership is conceptualized and operationalized within a community and/or institution. Since no single framework perfectly captures the socially constructed and multifaceted nature of leadership, educators must often pull from and weave together multiple theories and models when creating leadership development programs. This article explores consideration for leadership theory application through contextual and audience alignment, as well as considerations for integration of theory that address underlying theoretical assumptions, framework gaps, and developmental readiness. Reflection prompts are provided for each consideration so educators can envision practical implications from insights surfaced.