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The literature on organizational culture and leading by shared values suggests a prescriptive model for use by leaders in actualizing stated organizational core values. Utilizing a qualitative case study approach, this study sought to examine the efficacy of this theoretical model in representing actual efforts by practitioners to embed diversity as a new organizational core value. Leadership actions to embed and actualize diversity as an institutional core value at two private universities were examined and compared. Findings suggest the theoretical model inadequately addresses the critical role of contextual assessment and under represents the dynamic cyclical nature of value embedding and actualization processes, particularly with respect organizations with high stakeholder turnover such as institutions of higher education.