Programs supporting the necessary combination of digital, organizational, and cultural transformational change, motivating and engaging the workforce, are scarce. This discussion paper reports on the initial experiences from a competency development program aiming at building capacity within the workforce, leaders, and organization in secondary healthcare to navigate and facilitate digitally transformative healthcare systems. The program aims to support employees and leaders who i) understand digitalization in and of practice, ii) reflect and approach digitalization in a critical and ethical way, iii) are curious and maintain a growth mind-set, iv) engage in development and implementation of digitalization, and v) can convey and communicate digitalization. The insights from the prototype can be useful in further promoting sustainable digitalization within healthcare and supporting leaders in their conduct and management of digital health initiatives.