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"Underperforming schools" struggled to attract and retain staff in Chile, which hinders their leadership learning and development. Research on school improvement in this scenario requires studies of the subjectivities that school leaders build over time given the contextualised challenges. This study explores how principals change their vision over their roles and challenges during the first three years of appointment in the schools through sensemaking. Based on qualitative data analysis from interviews with seven principals, it was found that the key situation that led heads’ sensemaking process toward transformative instructional leadership was the support the process of valuing a common mission whilst embracing their teachers’ development needs. Results inform consequential models to inform meaningful programmes to support educational leaders’ lifelong learning.