Knowing when it's the 'right time' to admit students from marginalized communities is a challenge and there are many questions to consider: Is our school community ready to embrace this student and family? Are our faculty equipped with culturally responsive pedagogy and other required expertise? Will the student and family feel a sense of belonging if they don't see themselves reflected in other community members? What do we need to adjust to serve this student and can we follow through? What will our community miss out on by not having the student attend? And most importantly, will we do more good than harm? You'll hear from administrators at TMI Episcopal and Mulgrave School about what has gone smoothly and what has gone sideways as they’ve worked to broaden the diversity of their communities. Participants will have the opportunity to reflect on their DEI goals, current initiatives and desired future states, and discuss as they wish, to develop some next step action items related to these questions of readiness.