It is necessary for public managers to be able to evaluate programmes in the context of complexity. This article offers key learning and reflections based on the experience of facilitating the evaluation of complexity with a range of public sector partners in Scotland. There have been several articles that consider evaluating complexity and theory-based approaches to evaluation; however, the literature is scarce when it comes to actually facilitating such approaches within the public sector. The article discusses the main steps used when facilitating outcomes planning with stakeholders and identifies some key challenges and learning in relation to undertaking this work. The article will be of interest to those that want to know more about the core components of outcomes-based evaluation and, moreover, to those that will undertake this type of facilitation within the public sector as part of organisational development and professional development.