Howell Township Public Schools in Monmouth County, New Jersey, has reimagined the roles of teachers, school leaders, and all educational professionals around the concept of a team of learning engineers who, through their students, make the world a better place. While education has long required teachers to work in groups, professional learning communities (PLCs), teams, and communities of practice to improve their practice, teams of learning engineers go beyond these structures to reimagine the role of leaders, the way they draw on teacher expertise, and the way resources and supports are leveraged so that professional learning meets everyone's needs. To support this evolution of learning environments, Howell Township has dramatically reorganized its professional learning around a school-focused, collective, continual sensitivity to learner agency. To best understand how they have reorganized professional learning, it is helpful to look at their shifts alongside what organizational psychology refers to as collective mindfulness in high-reliability organizations (Weick & Sutcliffe, 2015). The five key elements of collective mindfulness within high-reliability organizations are: (1) Commitment to resilience; (2) Deference to expertise; (3) Sensitivity to operations; (4) Reluctance to simplify; and (5) Preoccupation with failure. Each of these elements is discussed in the article.