This qualitative study examines how leadership and organizational dynamics cultivate lecturers’ readiness for change in higher education. Drawing on transformational leadership theory, it explores the interconnected influence of leadership style, organizational culture, and perceived organizational support on 20 English-language lecturers in an Israeli college that has recently faced multiple overlapping changes: the national transition to CEFR-aligned instruction, the shift to online teaching during the COVID-19 pandemic, and the institutional and emotional disruptions caused by wartime conditions. Interview transcripts were analyzed using a thematic content-analysis approach. Findings reveal that lecturers’ openness to reform was strengthened by leadership characterized by competence, emotional intelligence, and accessibility; by a communicative and developmental organizational culture; and by perceived institutional care and support. Together, these dimensions fostered a sense of secure attachment to the organization-an underexplored relational mechanism linking leadership and readiness for change. The study contributes to leadership theory by proposing that Attachment Theory offers a valuable interpretive lens for understanding how relational trust and emotional security may support adaptive capacity in educational institutions. Implications are discussed for leaders seeking to sustain reform during crisis and instability through relational, emotionally attuned leadership practices.