Digital transformation is a process of digitizing the working and living environment in which people are at the center of digitization. In this paper, we present a personas-based guideline for system developers on how the humanization of digital transformation integrates into the design process. The proposed guideline uses the positive personas from the beginning as a basis for the transformation of the working environment into the digital form. We used the literature research as a preliminary study for the process of wellbeing-driven digital transformation design, consisting of questions for structuring the required information in the positive personas as well as a potential method that could be integrated into the wellbeing-based design process.