This checklist outlines key features for managing authorities and intermediate bodies of the European Social Fund Plus (ESF+) to consider when they want to stimulate innovation and promote digitalisation in employment, education, and training. The checklist was developed as part of the work of the ESF Transnational Cooperation Platform (2020-2022). The questions featured in this document will guide those managing or implementing the ESF and ESF+, including managing authorities, intermediate bodies, relevant ministries, and organisations working to develop projects and initiatives promoting digitalisation in employment, education, and training. The document draws on the experience and recommendations of Community of Practice (CoP) members shared via the ESF Transnational Cooperation Platform activities related to education and skills. In particular, it builds on the reflections of the Study Visit 'Practical actions to encourage the development of high-quality digital learning experiences' that took place on 9/10 May 2022.