Decisions made by user interface designers play an influential role in how people interact with software, this is especially true when it comes to the creation of tools to support teaching. As technology continues to play a more prominent role in schools, it poses an important question about how the design of learning tools influence what teachers do in classrooms. Data analytics is one opportunity technology offers for teachers to foster collaboration in student groups. Data analytics have the potential to provide teachers with a live view of what students are doing when using technology, which research shows is challenging to implement in classrooms. This paper focuses on the process to design a tool that assists engineering discussion session teacher assistants (TAs) to monitor collaboration within groups. We report on findings from interviews with TAs on what they anticipate they would need in order to support group work, and discuss how their responses influenced the design of this tool.