In contemporary Project Management literature and practice, it is possible to distinguish two paradigms: the algorithmic-rational paradigm and the relational paradigm. The algorithmic-rational paradigm is characterized by a sequence of programming methodologies that constitute the classic corpus of knowledge on Project Management (WBS, CPM, PERT, Gantt diagrams). Following the diffusion of Agile methods, dissatisfaction with the algorithmic-rational paradigm has spread and a Visual Planning approach, based on the decentralization of planning and control and the abandonment of algorithmic techniques (such as CPM and Gantt diagrams) in favour of simpler, visual and physical tools, has become increasingly established. Visual Planning is the concrete manifestation of a relational project management paradigm. In this work, through an analysis of the key practices characterizing Visual Planning, we have identified the five fundamental principles that define this approach to project management. Then, to structure and guide the choice of a software application that can support Visual Planning, we have (1) identified several features which allow distinguishing one software from another, and (2) created a correlation matrix between the core principles of Visual Planning and the software features. Through this matrix, it is possible to evaluate and measure the adherence of project management software applications to the logic and practices of physical Visual Planning.