Engagement and well-being are complex phenomena that deeply depend on the individuals themselves and include subjective perception of the past, present, and future experiences. Connecting with work adds a concrete dimension to engagement and well-being that makes it possible to consider designing for and assessing them in a given work context. In the gaming domain, gameful design is known as an efficient mean to increase engagement and well-being. This paper presents an approach to address both engagement and well-being at work and builds on the evolution of the field of HCI over the years to identify means of addressing engagement and well-being. We describe the concepts related to usability and how they evolved towards user experience to encompass more complex (related to self) elements. We show how previous work in the field has connected these major properties (using tasks descriptions) and how it might be possible to extend further embracing human needs and motivation theory. We propose to use gameful design and automation design (via RCRAFT framework) as two contributing disciplines to identify design options for increasing engagement and well-being of users/operators while performing their activities. Application of the framework is given by means of a concrete application building on top of the original Mackworth clock.