Information systems are an important organisational asset and offer numerous benefits. However, organisations face continued challenges when upgrading aging information systems, and the data contained within, to newer platforms. This article explores, through conversations with information systems professionals in four organisations, the potential development of a 'Rosetta Stone', which can translate data between systems, and be used to help overcome various challenges associated with their modernisation. Despite mixed feedback regarding the Rosetta Stone concept from interviewees, solutions highlighted in literature combined with participant feedback presented theories for its development, primarily as a tool to enable meaningful interpretation of data, rather than direct translation. The conclusion reflects on data collected to recommend a framework for how the tool might be developed, and has potential to be of significant interest to practitioners, open-source communities and organisations.