How are you teaching? The question, and aptly titled teaching initiative, posed by The Michael V. Drake Institute of Teaching and Learning asks us to reflect on what discoveries about remote learning have surfaced and consider artifacts to curate and share with colleagues. What instructional strategies worked? What do you need to be successful in the virtual environment? Furthermore, what are the ways in which we are staying connected with peers and student learners? Quickly establishing communities of practice during the COVID-19 Pandemic is important. This #MedEdPearls highlights a teaching initiative leveraging an iterative rapid prototyping strategy for professional development.