Software engineering educational approaches are often evaluated only anecdotally, or in informal pilot studies. We describe a unique approach to evaluating a software engineering educational technique (SimSE, a graphical, interactive, customizable, game-based software engineering simulation environment). Our method for evaluating SimSE went above and beyond anecdotal experience and approached evaluation from a number of different angles to form a comprehensive assessment of SimSE’s effectiveness. In this paper we demonstrate the insights and lessons that can be gained when using such a multi-angled evaluation approach. Our hope is that, from this paper, educators will: (1) be provided with evidence about the educational effectiveness of SimSE, and (2) learn ideas about how to comprehensively evaluate their own approaches.