The importance of well-prepared professionals is a widely recognized cornerstone in supporting children and families in infant-toddler settings. Nonetheless, research carried out in Portugal has identified weaknesses at the level of preservice and in-service professional preparation for working with children under-three. This chapter focuses on an action research process carried out in two toddler rooms aiming at the transformation of quality of both rooms through a centre-based teacher education process. Specifically, it focuses on describing and analysing the support to professionals in observing and interpreting toddlers’ experiences through the use of the experiential approach proposed by Laevers and collaborators. This approach emphasizes the central role of observing toddlers’ wellbeing in order to answer the question how the children are feeling? (Laevers et al., SiCs [ZiCo]—Wellbeing and involvement in care: A process oriented self-evaluation instrument for care settings—Manual, Kind & Gezin. Center for Experiential Education - University of Leuven, Research, 2005). It recognizes that the attention to toddlers’ wellbeing has enormous potential for understanding how the pedagogical environment influences their experience and is a relevant input for qualifying the educational settings. Results show positive effects of the action research process, with educators revealing a more individualized and intentional approach to observing and interpreting toddlers’ experiences, while also acknowledging difficulties and struggles in sustaining these processes in a continuous and systematic way. Implications of the study are discussed stressing the right of professionals to participatory, experiential and reflexive professional development opportunities as a condition to guarantee toddlers’ right to wellbeing, involvement and learning.