Diversity, equity, and inclusion is one of five pillars upholding the American Occupational Therapy Association's (AOTA) strategic plan. Ensuring organizational, educational and governance structures, policies, programs, and services all reflect diversity, equity, inclusion, justice and accessibility (DEIJA) is a priority for the profession. Yet, addressing DEIJA remains a significant challenge in the occupational therapy academic community. Educational programs are a gateway to the profession and play a critical role in whether minoritized persons feel they belong in occupational therapy. This paper proposes a set of Generative Disruptive Questions (GDQ) that can be used to critically examine practices within education that reflect commitment and action towards DEIJA and to facilitate focused conversations that accelerate the creation of measurable, action steps that ensure DEIJA practices are effectively addressed within occupational therapy educational programs. These questions are intended to foster authentic reflection and brave discussions that will dismantle processes and practices that perpetuate systemic injustices. These conversation starters could help faculty, staff and learners engage in courageous conversations that may, at times, be challenging, but which can lead to transformative changes. The questions promote reflective analysis of DEIJA in multiple aspects of the educational process from examination of vision and mission and DEIJA processes and practices in the broad institutional context to more focused analysis of the culture, climate, recruitment, retention, and teaching practices.