Digital technologies are transforming the job market and pose new challenges to education, yet there is little research that specifically examines how school principals' goals and leadership styles influence digital development in upper secondary schools. The present study explores how their ambitions and educational goals affect their approaches to leadership for digital transformation in their schools. The study employs an exploratory and qualitative research approach based on interviews with a full sample of nine upper secondary school principals from Central Switzerland. Transcripts have been analyzed using qualitative content analysis. The findings suggest that all principals express a clear orientation toward student-oriented teaching when integrating technology in their schools. However, there are substantial differences in terms of leadership processes to address this change: One principal oriented toward transformational leadership reported more rapid and more profound changes than all the principals oriented toward a more transactional type of leadership. In this case, transformational leadership is associated with faster implementation of digital technologies and also with a clearer focus on educational goals rather than on tools. This study expands the knowledge on principals' technology leadership practices as it provides insights into school leaders' attitudes and concepts and highlights the benefits of transformational leadership.