Participative Enterprise Modelling (PEM) has been used in Information Systems Development and Business Development for some time now. Research has shown that the full and positive effects of PEM methods heavily depends on the ability of its users to manage situational factors, which characterise, influence and constrain development situations where it is used. Therefore, a shift must be made in method development, from the invention of new methods to the development of guidelines for the practical use of current methods in various situations. Such a shift calls for research into the complex relationships between situational factors in development processes. This paper discusses the challenges of investigating the impact of situational factors on PEM and outlines an approach to be used as part of ongoing research.