Applications of Problem Structuring Methods (PSMs) are extensively reported in the literature; however, their evaluation remains challenging. Moreover, scholars’ disagreement on how to evaluate and compare PSMs constrains research that seeks to show whether certain PSMs are more useful than others within particular contexts and ‘better than doing nothing’. Drawing on scholars’ suggestion to evaluate PSMs through a link between action, outcomes and context, we address this gap by adopting an exploratory, quasi-experimental research design with MSc students to evaluate and compare three workshops supported by the use of (i) Strategic Choice Approach, (ii) Soft Systems Methodology and (iii) a non-PSM supported approach, and report on the findings of a quantitative and qualitative analysis. We explore the usefulness of PSMs for achieving outcomes that can support decision making. Our findings show variation in the usefulness of the three approaches and the different workshop outcomes.