It is well known that human resources play a valuable role in a sustainable organizational development. Indeed, this work will focus on the development of a decision support system to assess workers’ satisfaction based on factors related to human resources management practices. The framework is built on top of a Logic Programming approach to Knowledge Representation and Reasoning, complemented with a Case Based approach to computing. The proposed solution is unique in itself, once it caters for the explicit treatment of incomplete, unknown, or even self-contradictory information, either in terms of a qualitative or quantitative setting. Furthermore, clustering methods based on similarity analysis among cases were used to distinguish and aggregate collections of historical data or knowledge in order to reduce the search space, therefore enhancing the cases retrieval and the overall computational process.