Clinical Decision Support Systems (CDSS) play a critical role in modern healthcare by supporting healthcare providers in making well-informed decisions, improving patient safety and outcomes, enhancing efficiency, and promoting evidence-based practices. Their integration into clinical workflows can lead to more effective and patient-centered care. CDSS is essential tools for healthcare organizations as well as for healthcare providers to improve clinical care. However, successful implementation of CDSS can be challenging. Therefore, before implementing CDSS, it is crucial to assess the readiness of healthcare organizations to implement these tools. CDSS is essential tools in healthcare for several compelling reasons. For instance, enhanced patient safety, improved diagnostic accuracy, optimized treatment plans, consistency in care, and support for complex decisions. This study's aim is to develop a model that will help healthcare organizations identify the challenges of implementing CDSS, and to assess their readiness for such an implementation in a comprehensive and multi-dimensional manner. Through a literature review, the first step of this research explores the concept of clinical decision support and CDSS, discussing their features, characteristics, and organizational hurdles to implementation. It also provides perspectives on CDSS adoption in the context of information systems and health technology. The review helped to identify research gaps, objectives, and questions. To address these gaps and to attempt to answer the research questions, a Hierarchical Decision Model (HDM) is proposed. The model allows us to assess the readiness of healthcare organizations for CDSS implementation. It presents four perspectives and sixteen criteria for a multi-dimensional assessment. The methodology involves expert panels for the HDM model's refinement, validation, and quantification. Two case studies are then presented to demonstrate the HDM model's application to identify real-world CDSS implementation challenges and to provide insights and recommendations. The research contributions are evaluated against the identified gaps in the literature review, with limitations and future research presented. In conclusion, this research provides valuable insights into CDSS implementation readiness assessment and highlights the need for careful consideration and planning. The proposed HDM model offers a valuable framework for healthcare organizations to evaluate their readiness for CDSS implementation.