Tree planting initiatives (TPIs) are a common strategy for leveraging the benefits of vegetation in urban areas, but there has been limited research on the tree preferences and values of urban TPI leaders, and few studies comparing these attributes between different TPI stakeholder types. We conducted a qualitative study with 18 leaders from nine urban TPIs in Massachusetts, U.S.A. Key differences were found between executive leaders (managers oriented toward conceptual program goals), and operational leaders (managers oriented toward applied practice). Operational leaders played a critical role in mediating executive leaders' focus on large trees as part of a collective common, to address broad goals such as urban cooling; while simultaneously responding to residents' preferences for small trees associated with aesthetic values and their broader lived experience. Understanding these stakeholder preferences, values, and interactions is important for TPI operations, including towards achieving better resident accord and addressing social justice issues.