This study examines how leaders’ critical reflection and Human Resource Management (HRM) strategies jointly shape employee engagement and resilience during organizational change. Using a qualitative multiple case study approach, data were collected from 30 employees across two Nigerian organizations experiencing transformation. Thematic analysis revealed that reflective leadership practices—marked by openness, learning, and shared sense-making—cultivated trust and psychological safety. Simultaneously, HRM strategies such as mentoring, coaching, and fostering a learning culture provided tangible support systems that helped employees adapt, maintain motivation, and sustain performance amid uncertainty. The interplay between reflective leadership and HRM practices created a reinforcing cycle, strengthening employees’ confidence and commitment. The study contributes to theory by demonstrating that critical reflection is not merely an individual competency but a relational practice embedded in leader–follower interactions. Practically, the findings highlight the importance of integrating reflection training and developmental HR interventions to build organizational capacity for change. Future research should adopt longitudinal and mixed-methods designs to explore how these dynamics evolve over time and in different cultural contexts. Overall, this work underscores that reflective leadership and supportive HRM strategies are essential for fostering resilience and engagement in rapidly changing environments.