Educators play a crucial role in student skill development; hence this dissertation explores incentive-driven public policies and understands the effect that educators have on students. The first chapter estimates relative contributions of the subjective (supervisor observations and student surveys) versus objective (value-added) evaluation measures in capturing teacher effectiveness at increasing cognitive and non-cognitive skills. I use data from a large urban public school district where teacher compensation is tied to the evaluation measures. Estimates reveal that the subjective measures provide information about teacher effects on short-run achievement and absences as well as long-run achievement in ways that value-added does not. However, value-added remains the most significantly related to long-term achievement and absences along with short-term achievement. Chapter 2 uses a regression discontinuity design to investigate the effect of categorical evaluation ratings on principal composition and future school leadership effectiveness. I find that principals with rating scores that place them just below the higher rating cutoff are more likely to exit the district and less likely to be promoted. However, there is no evidence of a change in future leadership productivity in schools where principals fall below the cutoff. Principal transitions around the rating boundary may be driven by changes in motivation, employer demand, or salary. Exploiting the fact that crossing the higher rating cutoff does not result in a salary change for all principals, I document that the transition effects are concentrated within the group that does experience a salary change. Lastly, Chapter 3 uses administrative data from Texas to estimate middle school principal effects on cognitive and non-cognitive skill development and the relationships between these skills and attachment to post-secondary schooling, work, and engagement with the criminal justice system. Estimates show highly significant effects of principals on the probabilities of future engagement with the criminal justice system, attending and persisting in college, and working. The impacts on the probability of engagement with the criminal justice system come through effects on the development of non-cognitive skills, while impacts on post-secondary schooling and work come through effects on the development of both cognitive and non-cognitive skills. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]