Drawing on four years of anecdotal data and student feedback on course evaluations, this paper provides a retrospective account of the author's experience with teacher candidates in an elementary writing instruction course as first-time authors of children's books, in particular focusing on a writing workshop approach as an effective pedagogical orientation to scaffold reluctant writers through the writing process. The primary diagnostic "tool" or form of assessment of student writing within the writing workshop model of instruction is accomplished through writing conferences. In the practice of conferring as a primary form of assessment, a constructive literacy approach is embraced within which the assessment of student writing is designed to offer ongoing targeted feedback and incremental goals for improvement, as well as guide subsequent re-engagement lessons. In the process, students' stamina as writers is built, the assessment stance and overall effectiveness as an instructor of writing instruction is improved, and the learning outcomes of the course are better met. The paper serves a paradigmatic or illustrative purpose that may inform other education professionals and contribute to their repertoire of pedagogical skills or assessment practices, encourage conversations about honing our craft as educators, and generate questions for future empirical analysis.