Policy tends to be formulated at the upper level of an organization and handed down to policy actors on the frontline for enactment. Since policy can be vague, ambiguous, or send conflicting messages, it can create uncertainty about its meaning. Moreover, policy is rarely accompanied by explicit instructions for implementation. Therefore, when frontline workers, or streetlevel bureaucrats, are pressed to make sense of policy's meaning in realistic terms, they engage in what Weick describes as sensemaking (1995). Sensemaking is a cognitive process entered into during times of uncertainty or change. Streetlevel bureaucrats engage in sensemaking by drawing on cues in their environment, their prior experience, professional identity, and social interactions to understand and interpret policy. They rely upon their understanding to exercise professional discretion while incorporating the new policy into their daily work. It is their use of discretion that accounts for variations in policy implementation and outcomes (Lipsky, 1980, Mills, 1998, Spillane, 2004). This study explored how streetlevel bureaucrats in higher education institutions engaged in sensemaking during policy implementation. For this study, academic tracking initiatives were regarded as policy that academic advisors (streetlevel bureaucrats) were tasked with enacting. Historically, academic advisors have been identified as advocates for holistic student development while academic tracking has been defined as a prescriptive approach to advising aimed at accountability and efficiency. This qualitative study presents the findings from interviews with 16 academic advisors from three public institutions involved in the implementation of tracking. The study's findings suggest recommendations that may be helpful to leaders seeking to close the gap between policy and practice. Implications for practice include developing a strategic approach to implementation in which upper level administrators guide change by acting as sensegivers. As such, administrators would serve as filters for the messages received by streetlevel bureaucrats. Additionally, findings suggest the inclusion of frontline workers in decision making and the provision of planned learning opportunities for collective sensemaking during the implementation process. This study seeks to inform leaders involved in policy change about the critical role of sensemaking in initiating, guiding, and sustaining organizational change.