Planning is a vital decision making activity that influences the future of an organization by determining what tasks are to be performed, who required resources are and in what sequence. Organizations often follow a rigorous process to plan and deliver projects optimally based on the given resource and budget constraints. However, uncertainties increase the complexity of the planning process and contribute towards increased cost, delays and resource allocation issues. Therefore, it is important to understand the uncertainties and constraints associated with project activities and their effect on both business processes and organizational goals. Understanding the causal relationships between activities and constraints could allow organizations to operate more effectively and efficiently even in uncertain environments and lead to a more informed decision making process. This paper exemplifies the use of discrete event simulation tool to develop a strategically focused project delivery plan founded on the assessment of uncertainties that could arise during the delivery of the project. Proposed methodology follows a structured and systematic approach in order to identify the factors that can affect the delivery of the project and evaluate solutions that may mitigate or reduce the risk to As Low As Reasonably Practical (ALARP). The main objective is to complement the existing project planning activities rather than replace the existing tools.