Over three days, 180 junior and senior high school English teachers, postsecondary (university and college) writing instructors, workplace (corporate and small business) writing instructors, and government officials who are responsible for portfolios related to workforce training and literacy met to understand from a broad systems-level perspective how writing development was being supported and assessed in Alberta Canada. Conversations were structured using Dynamic Criteria Mapping (Broad, 2003) as a method for understanding the values, expectations, and contextual factors that shape the system. Participants shared values related to clarity of expression, risk-taking, and ability to motivate audience. These values, however, were enacted differently within school and workplace contexts. Writing as a problem-solving activity was identified as a tool for enhancing knowledge transfer within the system. Alberta's large-scale writing exams, on the other hand, created barriers to transfer and development by undermining shared values within the system. Recommendations related to curriculum redesign, pedagogical change, assessment reform, and professional development are suggested for enhancing students' longitudinal development as writers.