Planning is a ubiquitous dimension of service-learning and community engagement (SLCE) partnership practice. How SLCE administrators conceptualize, inhabit, and negotiate their roles as planners remains empirically underexplored, as does when and why planners experience shifts in perspective that affect partnership quality and outcomes. Building on prior work devoted to program planning theory, we introduce the concept of planning orientations and report on a pilot study in which SLCE administrators reflected on their desired and practiced planning orientations as they planned and implemented a partnership reflection process. Key findings illustrate the value of planning orientations as a construct for investigating planner mindsets and practices, and the utility that structured reflection on planning orientations holds for enhancing reflexivity in community-academic partnership practice. Our findings encourage the field to give more explicit attention to reflection on planning orientations in SLCE professional development.