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This study explores the problem-solving strategies of special education administrators in Northern California during the COVID-19 pandemic. Special education administrators play a critical role in balancing legal compliance with educational quality to support students with disabilities. The research examines the dual challenges of maintaining compliance and addressing pedagogical needs, highlighting key tensions such as bureaucracy versus improvisation and siloization versus collaboration. Utilizing qualitative methods, including interviews and reflective conversations, this research uncovers themes that underscore the complexities of special education administration particularly during crisis conditions. The findings reveal how macro-institutional pressures and organizational limitations shape problem-solving processes, emphasizing the need for systemic changes that enhance flexibility and responsiveness to better meet the evolving needs of students with disabilities.