Culture change implementation in nursing homes has made notable strides over the past two decades but faces remaining obstacles. Obstacles to a central component of culture change, resident choice in daily life, have been researched little internationally and even less in the U.S. This study explored U.S. nursing home staff members’ perceptions of challenges to realizing resident choice in daily life and of possible resolutions to overcome these challenges. Semi-structured interviews were conducted at two purposively sampled Veterans Health Administration (VHA) Community Living Centers (i.e., nursing homes). Participants constituted twenty-six staff members, with positions varying in discipline and in hierarchical level. A modified grounded theory approach guided data analysis. Data analysis surfaced key challenges at the following three levels: intra-personal (e.g., resident personal characteristics, staff work demands), inter-personal (e.g., staff-resident power dynamics), and organizational (e.g., organizational policies). The most salient results were found at the staff intra-personal level; staff mental models of care often lacked clarity on how to promote resident choice when faced with challenges such as balancing the competing goals of resident choice and resident medical and safety needs. Findings also included staff-employed resolutions to resident choice-related challenges, i.e., preventive practices, staff and resident education, staff reinforcement, staff deliberation, stakeholder collaboration, and supportive leadership. This study pinpoints a comprehensive set of challenges and resolutions to challenges particular to nursing home staff promotion of resident choice. It offers specific and concrete insights on how this central component of culture change, and thus resident quality of life, can be advanced.