The Human Centered Management model focuses on the importance of the wellbeing of people as workers and users. The healthcare sector stands as one of the key fields responsible for the continuous improvement of the physical and mental wellbeing across society. This study was conducted in Italy at a time when the healthcare sector was undergoing major disruptions and pressures. On the one hand, dealing with budget reductions mismatching increasing requests for inpatient and outpatient services, in an environment subject to constant technological change. On top of the recurrent constraints, the world during the first quarter of 2020 was affected by the COVID-19 pandemic that dramatically challenged the national healthcare system. This chapter examines the case of the Modena Health Agency, located in one of the most affected regions of Italy. The analysis includes foreseeable solutions, best care practices and lessons learned from the experience in alignment with the Human Centered Organizational Culture, highlighting narratives and challenges leading to that transformation and renewed of healthcare system focused on the quality and safety standards of healthcare patients and professionals.