Developmental academic advisors' perceptions of their effectiveness in student retention are based on experiences with students. The problem addressed in this study was advisors' outcomes are not matching the expectations of administratively targeted retention initiatives mandated outside of their day-to-day practice. The purpose of this qualitative generic study was to collect and interpret experiences and perceptions of advisors in the context of their outcomes matching expectations of targeted administrative retention initiatives mandated outside of their day-to-day practice. Through a qualitative generic method, six developmental advisors participated in interviews and a focus group to discuss perspectives on retention initiatives. Advising theory, student development theory, and theory of organizational structure supported this study. The research questions addressed were how advisors describe their experiences with mandated targeted retention initiatives not typical of their day-to-day advising practice, and to what extent advisors perceive their outcomes match expectations of mandated targeted retention initiatives. In Vivo coding was completed to identify themes of advisor roles, employee morale, and organizational structure. This study can prompt administrators to support advisor input on development, reporting, and effectiveness measures of retention strategies. Retention initiatives, mandated without definition or expectations, do not provide advisors with tools for practical application. Implications include recognizing developmental advising strategy to establish opportunities for retention development and providing advisors opportunities to share expertise in support of change theory. Recommendations for research include defining advisor roles and exploring effectiveness strategies through practical design. Recommendations for practice include developing inclusive opportunities for advisors to engage in retention development to increase feelings of professional value and define clear retention initiative outcomes. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]