Research focuses on various macro and meso aspects of collaboration and less on the individuals who make decisions about their organizations' collaborations. Organizational leaders make these decisions based on their interpretations, influenced by their personal characteristics. Existing studies examining organizational outcomes such as a decision to collaborate typically consider these characteristics separately and independently, ignoring the reality that a leader's characteristics jointly and interactively shape perspectives, attitudes, and behaviors. We focus on five prominent characteristics in the literature—gender, educational attainment, prior cross‐sector experience, current cross‐sector affiliation, and tenure in position—and study their configurational dynamics regarding the organization‐level outcome—the propensity of cross‐sector collaboration. We employ qualitative comparative analysis to develop and test a configurational model for cross‐sector collaboration, using survey data of local government and nonprofit leaders in Lebanon. The analysis offers exploratory insights into four configurational types of leaders whose organizations opt to collaborate at the local level.