This study follows 305 preservice teachers (PSTs) who student taught in Chicago Public Schools (CPS) in 2014-15 and were subsequently hired in CPS in 2015-16. Drawing on surveys of PSTs and their cooperating teachers (CTs) and CPS administrative data, we linked features of their preservice teacher education to three outcome measures for instructional readiness: (i) CTs' perceptions of their PSTs' preparedness to teach at the end of student teaching, (ii) PSTs' self-perceptions of preparedness at the end of student teaching, as well as (iii) PSTs' first-year observation ratings based on the district evaluation rubric. We first investigated whether these outcome measures were related to one another. We found that CTs' perceptions of PSTs' preparedness positively predict first-year observation ratings but PSTs' self-perceived preparedness were unrelated. We then examined which features of preparation were positively related to these three outcomes and whether or not the same features predicted all three outcomes. PSTs received stronger first-year observation ratings when their CTs had stronger observation ratings themselves, their CTs reported providing stronger coaching in specific instructional areas, they gained employment in the same school in which they had completed their student teaching, and when their placements had been in self-contained elementary classrooms. However, these same features were generally unrelated to our two other survey-based outcome measures, while others emerged as important. This study then provides suggestive evidence that different features of preparation are likely promising levers for program improvement but that program leaders and policymakers must first consider which outcome might determine "improvement," as different features appear to be associated with different measures of instructional readiness.