Vignettes are hypothetical scenarios of many forms that are presented to interviewees in qualitative studies to elicit participants’ answers on diverse topics. Although there are few scholars having discussed the application of vignettes in qualitative studies, there is no article assessing the implementation of vignettes in the field of educational administration. Therefore, our article discusses the vignette technique as a data collection tool within the qualitative methodological paradigm with a focus on the aforementioned field. More specifically, in the first section we outline the design of hypothetical scenarios and their advantages and disadvantages as a data gathering tool, according to the relevant literature. The rest of the article is an account of our findings, when we used vignettes with semi-structured interviews to investigate the Greek principals’ value orientations. Findings suggested that answering to the stories was a very interesting and enjoyable process that made the principals talk without reservations. Furthermore, reflecting on their professional practice the participants were willing to share similar incidents from their experiences. One critical factor for vignettes to be effective is to be close to reality of respondents.