The importance of IT projects and their impact on critical business processes has increased in recent years. A successful project is therefore an important goal in the client-consultant relationship. Current research shows that the fitness of a project management approach determines the overall success of a project, which makes the evaluation in the beginning of a project even more crucial. Consultancies and companies alike face the challenge of finding the right project management approach to guide IT transformation projects at an early stage. This research aims to bring transparency to the decision-making process of evaluating a project management approach based on an explorative study. Experienced experts from the consulting side were interviewed to facilitate an understanding of which factors are the most important to consider in this process. Our findings suggest that the decisive factors are client characteristics in terms of Agility Expertise, Flexibility or Security Need, Openness to Change and Governance Structure, in combination with project settings, like the rigidity of scope, budgeting model or project lifecycle status.