The development of human skills through technology, knowledge co-creation, and meaningful work drives successful change, well-being, and societal cohesion. Technological advancements have raised concerns about job displacement and skills shortages, necessitating a human-centric approach to leadership. The study explores the relationship between meaningfulness and meaninglessness (m&m) experiences at work, emphasizing that meaningfulness is not tied to formal job descriptions and can be supported by leadership. Transformational leadership, with its four dimensions Idealized influence, Inspirational motivation, Intellectual stimulation, and Individual consideration, is examined for its potential to foster meaningfulness in education and elderly and caregiving sectors. The research, based on the “The m&m of work” project, aims to enhance organizational practices by leveraging employees’ experiences of meaningfulness and meaninglessness. This research focuses particularly on transformational leadership (TL) entity of the survey and the identification of four dimensions of TL (visioning, challenging, engaging, and leading by example) in the real-life experiences of the education and elderly and caregiving sectors at both individual and organizational levels. The study found that Transformational Leadership (TL) had significant influence in the education and caregiving sectors. At the organizational level, TL influenced areas such as responsibility and ethics, work environment safety, and discussions about the meaningfulness of work. At the individual level, TL fostered trust within the work community, encouraged the use of employees’ creativity, and supported their success. Additionally, a method was co-created during the research to enhance leadership, facilitate knowledge sharing, and promote discussions within organizations, addressing even challenging experiences of meaninglessness and their effects.