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A vast array of leadership dispositions associated with school and student success is well-documented in extant leadership development literature. However, persistent challenges face practitioners as they attempt to measure leader dispositions and apply what is known about dispositions to hiring, selection, development, and retention of school leaders. We begin this chapter with an exploration of the essential leader dispositions which surfaced through an exhaustive cross-disciplinary review of literature, in concert with a review of disposition tools and frameworks in use in a variety of practical settings. Next, we illuminate significant challenges associated with reliably measuring school leader dispositions and explore promising emergent innovative strategies for assessing disposition development. Though difficult to measure, we argue that dispositions are too important to ignore and conclude with practical recommendations for using research on leader dispositions to cultivate outstanding school leaders.