Context: Education and skills have the potential to improve both economic performance and societal well-being, while tackling overarching challenges such as the twin digital and green transition. To realise this potential, an increasing share of countries have used strategic policy documents in the area of skills policy, colloquially called “skills strategies”. However, despite this prominence, systematic approaches for comparing skills strategies and their implementation across countries are scarce. Approach: In this report, we conduct a comparative analysis building on in-depth case studies of strategic policy documents on skills and their design and implementation processes in five countries: Austria, Bulgaria, England (UK), Germany, and Norway. By using a most different system research design, we identify the strategies’ main benefits for the countries' skills systems and interrelatedly the effectiveness of their specific policy measures, as well as frequent barriers for implementation and the central success factors of such strategies. Findings: The study shows that skills strategies which are encompassing the preferences of broader groups of stakeholders, adaptable to changing circumstances and internally consistent are particularly well suited to mitigate potential barriers for implementation. Conclusion: The analysis suggests that while well designed skills strategies can trigger incremental, gradual institutional change by building foundations for policy coordination, reinforcing policy priorities and improving complementarity between individual policy measures, their potential for bringing about outright, disruptive institutional change is limited.