Tending to long-term landscape health and resilience is a highly complex enterprise. To address this complexity, we must imagine and facilitate a community-based response that is just as complex, inclusive, interdependent, informed, deliberative, and adaptive as the challenges we face. Conservation and stewardship partnerships are a now-familiar way to try to tackle this monumental task. However, successful conservation partnerships are not possible without leadership that can explore shared values amidst dissenting views, navigate complex and technical information to bring all parties to a shared understanding of the issues, manage conflict and facilitate difficult conversations, and approach these multi-faceted challenges with humility and empathy. This is both the challenge and the opportunity of collaborative leadership. The series of papers in this issue of Parks Stewardship Forum on “Collaborating Well” explores what makes collaborative leadership work. This introductory piece illustrates why collaborative leadership is so critical to meet our landscape stewardship needs. The article on the Partnership Impact Model goes beyond describing this work and delves into how to measure its impact. Moreover, the article on peer learning provides examples of how to advance collaborative leadership successes by sharing critical knowledge, experience, and skills with others. Within all of these facets of collaborative leadership are social and cross-cultural competencies that further enable this work.