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The objective of the study was to determine how women leaders in two different higher education institutions succeed. A multi-case study was conducted with two participants that included a CAO-COO Vice President of Administration and Finance of a four-year university and a President of a two-year college. The study explored why women were able to succeed and how they persisted in overcoming challenges. Data were triangulated with artifacts, observations, and interviews. Constant Comparative method of analysis with open coding was used to collect, transcribe data while salient themes and patterns surfaced. Discussion and findings show the women in the study were cognizant feminine styles. opportunities and challenges. Conclusions summarize outcomes of studies and implications for the future with practical suggestions.