This study explores the specific issue of supervision as an important administrative gate keeping function that facilitates or impedes women's career advancement, and promotes gender equity at the executive leadership level in community colleges. The very nature of supervision mirrors the historical purpose of higher education, employee learning and development. Key themes, including institutional culture, effective supervision, and positive encouragement with employees provide an understanding of the relationship supervision has on improving equitable female representation at the executive management level. Data collection included a unique application of the Synergistic Supervision Scale (SSS) and interviews with executive leaders and mid-level managers to uncover the supervision context within the community college milieu. A conceptual model is provided for supervision that specifically supports women's career mobility from mid-level to executive management. (Contains 2 tables and 1 figure.)