The EnCoMPASS project (Emerging Communities for Mathematical Practices and Assessment) at the Math Forum and Drexel University has produced a web-based software tool for the assessment of student work. This paper discusses research on the impact of the tool on teachers' attitudes toward work with students in the software environment. The tool supports teacher to take a more dialogic approach to work with student and engage in the dialect of problem solving, discussion and mathematical thinking. It is suggested that the tool aids teacher to transition toward this more interactive approach teaching mathematics while supporting them in their concerns for the time to engage in more detailed dialogue and thinking about mathematics with their students.