This study is based on a Task Design and Analysis activity from a year-long professional development program. The activity was designed to increase teacher growth in several areas, including knowledge of mathematics, understanding of students' cognitive activity, knowledge of good questions, and ability to develop and improve high quality tasks. The study collected data from 30 classroom teachers. Results include teachers' initial understanding of the task, teachers' interpretations and awareness of the strategies their students used to solve the task, and the pattern of revised tasks. The process and findings of the study will expand teacher educators' understanding of structured approaches to link an inservice PD with teachers' work context as well as develop a better analytic framework within which teachers and teacher educators analyze student work.