This article summarizes findings from an experimental evaluation of After School Matters (ASM), a paid, apprenticeship-based, after-school program in Chicago for high school students. Analysis of quantitative data from a mock job interview revealed that ASM participants did not demonstrate more marketable job skills than youth in the control group. Qualitative data suggested that the nature of interpersonal interactions and the degree of professional orientation in apprenticeships contributed to variation in marketable job skills across apprenticeships. The article considers the perspective of human resource professionals who participated in the evaluation and describes an interviewing skills curriculum developed in response to the evaluation findings.