Situated in the diversity and adversity of real-life contexts facing crisis situations, this research aims at boosting the resilience process within communities supported by digital and social technology. In this paper, eight community leaders in different parts of the world are invited to express their issues and wishes regarding the support of technology to face social challenges. Methods and artefacts based on the Organisational Semiotics (OS) and the Socially-Aware computing have been applied to analyse and consolidate this data. By providing both a systemic view of the problem and also leading to the identification of requirements, the analysis evidences some benefits of the OS-based approach to consolidate perspectives from different real-life scenarios towards building a socio-technical solution.