American higher education is in crisis. Persistent opportunity and achievement gaps limit college access and completion for low-income and underrepresented students. Fewer students are completing their studies on-time, thus prolonging their entry into better paying, career-focused employment. Meanwhile, the cost of attending college and related student loan debt continues to escalate. There have been calls for comprehensive systemic change dating back to the 2006 Spellings Commission, yet performance data demonstrates that little has improved. While there is voluminous research on change and change management in higher education, there remains much to be learned about implementing and sustaining change, and about the roles and behaviors of specific actors beyond the college president or executive leaders. This study focused on the role of community college academic deans as middle managers during planned organizational change. Study participants included eight academic deans from community colleges in the Northeast that are currently implementing guided pathways. Interpretative phenomenological analysis (IPA) methodology was utilized to examine how participants made sense of the experience of being middle managers during planned change. Findings revealed four super-ordinate themes that characterized their experiences: deans' roles and responsibilities; leading & managing; mindset; and executive-level sense-making/sense-giving. Knowledge generated from this analysis can inform the professional preparation, ongoing development, and day-to-day practice of community college academic deans and other middle managers, and executive leaders as they work together to advance student success by improving organizational function and performance. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]