This two-phase sequential mixed methods exploratory study examined the perceived skill deficits of instructional deans at California community colleges to better understand the training and development needs that are necessary to support dean success and to prepare them for advancement in a timelier manner. This study is grounded in the theoretical framework of social constructivism and system dynamics. The literature indicates a need for competent leaders in the hiring pipeline to fill the predicted vacancies of the baby boomer generation in California community colleges. Despite the ongoing warnings in the literature for the past decade, little has been done to prepare future leaders for the mass exodus of senior administration. Further, given the structured path to senior administration, very little research has been conducted on mid-level administrators despite the critical role that they play in day-to-day college operations and the fact that mid-level administration is the accepted training ground for senior leadership positions. This study focused specifically on instructional deans, who make up a large portion of mid-level administrators. Perceptions were elicited from California community college instructional deans, senior administrators, and faculty. Results indicated that, overall, all three constituency groups interviewed and surveyed generally agreed on the skills required to be an effective instructional dean. However, there were frame gaps in perceptions, based on the position of the respondent, when it came to identifying instructional dean skill deficits, training provided for deans, and support. Additional findings indicated that on-the-job training is the most common form of instructional dean training used by colleges