This chapter highlights the importance of pedagogical development for engineering educators and its positive influence on their leadership journeys. It begins by problematizing the linear approach currently dominating the provision of training to engineering faculty members and proposing a system thinking approach to conceptualize engineering faculty’s learning as a complex dynamic system of interrelated components, including personal professional growth and interactions with environmental factors such as institutional conditions and cultural values. Through three case studies of different approaches to pedagogical development and cross-case analysis, recommendations are made for future institutional activities aiming to support academic leadership for all. These include (1) organizing PD activities centering engineering educators’ intrapersonal characteristics developed, based on their prior experiences and personal interests, and designs to engage their pedagogical knowledge to enhance their self-efficacy. (2) Providing opportunities for engineering educators to engage proactively and agentically in the decision-making and implementation processes regarding engineering professional development. (3) Creating space for engineering educators to use their expertise to influence others, from the individual classroom to the institution as a whole. Policies that recognize and reward teaching can be powerful in supporting engineering educators to sustainably engage. In general, engineering educators’ professional learning and academic leadership can be developed through practical learning and professional agency enactment.