The purpose of this study is to propose a structured approach to identifying and addressing the most damaging pitfalls or negative risks that may potentially hinder the successful implementation of a strategic initiative in an organisation. By using a combination of checklists acquired from literature, post-project reviews and interviews conducted with experts and project stakeholders, one may identify those pitfalls that may realise during the implementation of project portfolio management. The assessment of these pitfalls provides a prioritised pitfall list. Response plans to address the high-level pitfalls give the project team the required information to avoid, mitigate, transfer or accept the pitfalls. Monitoring and control processes can be used to appropriately track and address the pitfalls if and when they occur.