In recent years, a wide range of generic and domain-specific maturity models have been developed in order to improve organizational design and learning of healthcare organizations. While many of these studies describe methods on how to measure dedicated aspects of a healthcare organization’s “maturity,” little evidence exists on how to effectively implement and deploy them into practice. This article therefore delineates the encountered challenges during the design and implementation of three maturity models for distinct improvement areas in hospitals. On the one hand, this study’s findings may serve as basis for refining existing maturity model design approaches. On the other hand, it may facilitate further research in domain- specific organizational design with maturity models.