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Research suggests that assistant principals’ leadership tasks encompass various activities related to instructional leadership, student and school management, and community relations. Not all assistant principals have access to all these tasks. In this paper, we examine the extent to which assistant principals’ leadership tasks are associated with differential perceptions of the evaluation system. Performance evaluations provide ongoing feedback for career improvement and advancement. Using data from Tennessee, we find that assistant principals who spend more time on instructional leadership tasks are more likely to have positive perceptions of their evaluations. The misalignment between the roles that assistant principals undertake and the tools with which they are evaluated has equity implications for assistant principals’ development on the pathway to the principalship.