This article presents pilot study results of two leadership performance assessments, designed for a California principal preparation program and embedded in preparation using two learning approaches. The pilot study had two purposes: to evaluate the assessments' content validity and to evaluate the candidates' leadership skills as demonstrated through their assessment products and an independent self-assessment tool. The evidence showed the tasks to be valid and useful tools for formative leadership development for different candidates and school settings. Participant feedback on the assessments' benefits and independent self-assessment ratings provided construct validation. We concluded that these are promising assessment tools for programs' use in candidate assessment.