We live in a time of great change. Community leaders around the world face dilemmas in every aspect of human living systems – social, economic, and environmental. We sit at a crossroads: do we try to fix what clearly is not working any longer or do we step up and design something new to achieve our desired outcomes? The leadership of Bibb County Schools (BCS) – faced with this very dilemma – stepped up to redesign their education system in a bold and exciting way. The road ahead was challenging and not at all guaranteed, but the conviction and strong leadership in the County was undaunted. This case study shares how BCS district, Macon, GA, is engaged the whole education system along with community leaders in a generative process to accelerate whole system positive change. Ultimately, their desired outcome was to generate a new educational system that would “ensure that all children receive a high-quality education that will prepare them to be competitive and successful in a global economy” (BCS, 2011). This chapter highlights key intervention strategies, including the important role that an Appreciative Inquiry summit played, in generating whole system change. We highlight the positive strides made to date and the challenges the County faces going forward. We conclude with recommendations leaders can use when considering a community-wide, whole system change effort.

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