The potential of data sharing, particularly through Data Spaces, offers significant opportunities for the innovation community to address societal and business challenges. However, numerous obstacles must be navigated to effectively unlock this potential. In the last Data Week 2025 the projects under the HORIZON-CL4-2023-DATA-01-02 topic (CyclOps, DS2, CEDAR, NOUS and PLIADES) organized a workshop focused on identifying the critical challenges faced by industry and stakeholders in achieving seamless data sharing and leveraging Data Spaces across various sectors and domains; and explore innovative strategies to overcome these obstacles. The workshop aimed at putting together the insights obtained so far by the bird-of-a-feather projects and broadening its scope with the insights from the audience captured during the workshop to allow a more holistic discussion and scene around the topic. The discussion was organized in three main blocks, starting with a 1st block focused on getting a better understanding of who is the user of the different solutions that are being created to allow for data sharing, integration and leverage Data Spaces, and what is their expected added value sought. Once the user was identified, the discussion moved to the barriers to delivering value and the main pain points these users find. The third block allowed to share innovative approaches the projects are developing to overcome selected obstacles, and how these solutions contribute to Data Spaces and align with the DSSC blueprint and its building blocks. This paper collects the main insights shared and discussed during the workshop from both the projects and the audience, constituting a rich compendium of diverse perspectives and approaches that help illuminate the current landscape and offer perspectives for future work on the area