As virtual education and jobs become the “new” reality, most professional development opportunities require technological skills. But how should we evaluate them? Usually, we measure the number of activities or contact hours offered, the number of participants, increased knowledge or skill, or their level of satisfaction. Unfortunately, what happens after is not commonly addressed. The follow-up question we are interested in responding to is: how successful were these activities in promoting or improving significant uses of technology by the participants? For example, fast-tracked by COVID-19, the Puerto Rico Department of Education (PRDE) implemented the DE-Innova project to train educators on various technological tools. It involved a needs assessment, which was also used to evaluate project achievements. The results of this implementation presented an opportunity to reflect on what elements should be contemplated when evaluating these kinds of projects, considering the evolving nature of technology.