This article extends prior research seeking to identify preparation features related to better workforce outcomes. To our knowledge, it is the first to link many dimensions of preparation to graduates' first-year observation ratings. It follows 305 preservice teachers (PSTs) who student taught in Chicago Public Schools (CPS) in 2014-2015 and were subsequently hired in CPS in 2015-2016. PSTs received stronger observation ratings when their CTs had stronger observation ratings themselves, their CTs reported providing stronger coaching in specific areas, they gained employment in their field placement schools, and they student taught in self-contained elementary classrooms. Finally, we tested whether these same preparation features were associated with two other outcomes--(a) how well prepared PSTs felt after student-teaching and (b) how well prepared their CTs felt their PSTs were--and found they were not. We discuss implications for using workforce and survey-based outcomes to identify promising forms of preparation.