Scholars have produced a substantial body of research to analyze how school leaders can change their schools in challenging circumstances to improve organizational conditions, professional relationships, teaching and learning practices, and student outcomes. The main purpose of this paper is to analyze the complex structure of leadership in the learning area that has been created, as a consequence of Chilean educational policy, between principals and Heads of Technical Pedagogical Units (HTPUs). Chile has defined a particular leadership role within school organizations denominated Head of Technical Pedagogical Units (HTPU). This study used a multi-method approach, employing both qualitative and quantitative methods, to understand the leadership relationship between principals and HTPUs. The data results show that HTPUs have had to share leadership with principals, a phenomenon referred to as a bicephalous structure. This situation has resulted in a division of tasks and roles, and thus has introduced more complexity into the school context and an unproductive relationship in terms of leadership for learning. Distributed leadership should be considered as a real alternative to deal effectively with the bicephalous structure of leadership found in the Chilean scenario.