Class observations are as beneficial to teaching as peer review is to writing. Observations can help an instructor become aware of things they would not be able to notice on their own, as well as learn new strategies and ideas. In a nationwide survey that the author and her colleague conducted in 2015, class observations by a supervisor were rated as one of the most helpful training components by 74 graduate teaching assistants (TAs): 70% said they were "very helpful," and 30% found them "somewhat helpful." However, when asked to elaborate on their ratings, comments by the TAs revealed a caveat: the usefulness of observations depended on the extent to which the supervisor's teaching philosophy aligned with their own. One of the participants made a comment that inspired the author to reflect on her own practices: observations are not about professional development, but rather about "fitting into the strict departmental format." In this article, the author shares her reflections on this topic, as well as steps she took to improve how she conducts observations as a TA supervisor. It all started with shifts in perspectives, which then guided changes to products and practices.