On 11 March 2020, the World Health Organization declared COVID-19 to be a pandemic to be confronted by humanity. As a result, social isolation has become the norm in most countries, with the consequent replacement of face-to-face classes by classes mediated by information and communication technology. Within this context, this work sets out to investigate the factors necessary for courses mediated by technology to attain their pedagogical objectives. Additionally, the study examines how subjects that develop hard and soft skills differ in a technology-mediated setting. The results show that the teacher’s digital competence on the technological platform and the metacognitive support available in the digital environment are significant factors for a course to attain its pedagogical objectives successfully. Lastly, the study revealed that hard skill disciplines, when they migrate to technology-mediated environments, are more likely to fail to achieve their educational goals than soft skill disciplines subject to the same migration.