In wind energy, the accuracy of the estimation of the wind resource has an enormous effect on the expected rate of return of a project. For a given project, the wind resource assessor is faced with a difficult choice of a wide range of simulation tools and workflows with varying accuracies (or “skill”) and costs. There is currently no guideline or process available in the industry for helping with the decision of the most “optimal” choice—and this is particularly challenging in mountainous (or “complex”) terrain. In this work, a new decision process for selecting the Wind Resource Assessment (WRA) workflow that would expect to deliver the best compromise between skill and costs for a given wind energy project is developed, with a focus on complex terrain. This involves estimating the expected skill and cost scores using a set of pre-defined weighted parameters. The new process is designed and tested by applying seven different WRA workflows to five different complex terrain sites. The quality of the decision process is then assessed for all the sites by comparing the decision made (i.e., choice of optimal workflow) using the expected skill and cost scores with the decision made using the actual skill and cost scores (obtained by comparing measurements and simulations at a validation location). The results show that the decision process works well, but the accuracy decreases as the site complexity increases. It is therefore concluded that some of the parameter weightings should be dependent on site complexity. On-going work involves collecting more data from a large range of sites, implementing measures to reduce the subjectivity of the process and developing a reliable and robust automated decision tool for the industry.