This study examines the relationship between the reported career intentions and perceptions of preparedness of graduating secondary teachers in Quebec, across a two-year period, in an effort to identify factors which contribute to growing attrition rates among beginning teachers. The study reveals that those beginning teachers most concerned with their lack of preparation in the areas of classroom management and assessment of students' learning are more likely to consider leaving the profession. While evidence suggests that beginning teachers do develop increasing confidence in terms of classroom management in their second year of teaching, their challenges with effectively assessing student learning endure through the first two years of teaching. Findings from this mixed method study suggest that both initial teacher education and employers have a shared responsibility to give greater attention to the ways in which teachers are introduced to and have experience with strategies for the assessment of student learning.