This innovative practice work in progress (WIP) paper details the development of an observation protocol that was developed to promote pedagogical risk-taking and additive innovation. Our higher level goal is to create a self-sustaining community of pedagogical exploration through formative feedback driven by peer observation. This effort aims to break the mold of status quo professional development protocols with questions specifically designed to ensure educators are receiving targeted, desired feedback, while engaging observers to think about how they might apply something similar in their own classroom(s). Attempts to test this protocol unearthed deeper concerns about observations and faculty reluctance to be observed. This underlying anxiety and concern associated with observations needs to be addressed, particularly during the pandemic. In this paper we share our process of developing this protocol, our pilot testing of the protocol, barriers encountered in further testing of the protocol, and literature that explains faculty reluctance to peer observation protocols that will help guide future efforts.