I have been working as an Assessment Officer in a private university in Puerto Rico, for about two years now. It took a year to learn the job--what was assessment for, what was my function, how broad was the scope of my job, what influence did I have over institutional changes? Just as I thought I knew the job, the context changed, especially the shift to online modality, wrought by COVID-19. These circumstances have pushed me to review and reflect in every assessment aspect already learned and stated by the university's assessment office. Driven by this need for reflection, I came forward to virtual communities of educators (AALHE online conference, CLACSO virtual conferences and #abolitionistteaching on Instagram) who also had the purpose of reflecting over the educational process where assessment was not the exception. These communities have questioned, shared, and reimagined the educational process accordingly to what can be effective, given their experiences. I will share my reflections based on the learnings acquire from these virtual communities: there is a need to foster a change from a compliance paradigm to a culture of assessment that builds healthy relationships.