This follow-up study presents findings from 11 structured interviews that were conducted with principals engaged in a conversion from a large comprehensive high school to six small schools. Key findings are (a) the greatest barrier to improvement was entrenched instructional patterns and (b) goals of college readiness and social/emotional development, espoused by principals, only partially aligned with system-wide student assessments and school programs. The authors suggest that current accountability mechanisms fail to assess both college readiness and social/emotional development. For either goal to become more than a slogan, assessment of student learning must be substantially reinvented. (Contains 14 tables.)