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This study examines the critical roles of frontline supervisors and work cultures in shaping the career trajectories of low-wage frontline workers in healthcare workforce development programs. Although they do not control pay structures or promotions, supervisors directly influence how workers experience the organization through feedback, mentoring, and informal recognition. This suggests that they may act as gatekeepers to opportunity by determining which employees they deem as investment-worthy. This study also examines what organizational dynamics shape supervisors' willingness to invest in their low-wage employees, how supervisors' perceptions directly facilitate or impede worker mobility, and how their interpretations and actions influence program implementation. Using thematic analysis and drawing on interviews with 37 supervisors in four U.S. hospitals participating in workforce development programs, this study integrates Sensemaking Theory and Expectations States Theory to analyze how supervisors interpret organizational goals and assess worker competence under conditions of understaffing, high turnover and structural inequality. Findings reveal that supervisors’ support for worker advancement depends less on staff’s formal training and more on organizational factors such as leadership commitment, resource availability, and cultural norms of the organization. Supervisors act as pivotal agents in reproducing or disrupting job mobility inequality within low-wage healthcare work. Program outcomes are dependent on how supervisors manage competing demands and evaluate workers’ worth. Efforts to enhance worker mobility should focus not only on formal development programs, but also fostering organizational cultures that equip and incentivize supervisors to support advancement, recognize workers contributions, and balance competing operational demands.