This chapter frames public sector digitalization as a deliberate policymaking process aimed at reshaping organizational structures and service delivery. It conceptualizes digital transformation as either incremental or radical change, highlighting the importance of contextual conditions and design strategies. Drawing on Elinor Ostrom’s distinction between operational and collective-choice levels, the chapter illustrates how successful digital policies require coordination between these spheres. It introduces Digital Service Teams (DSTs) as instruments to bridge institutional design and on-the-ground implementation. The authors discuss challenges such as inter-organizational interdependence and resistance from entrenched interests, outlining expected strategies based on context typologies. DEG is proposed as a template for evaluating whether digitalization leads to paradigm shifts or muddling through. The chapter emphasizes the necessity of crafting adaptable, politically viable solutions rather than relying solely on technology. In doing so, it provides a conceptual framework to understand how administrative innovation occurs, and the strategic trade-offs that policymakers must navigate.