This paper presents pilot study findings of a research project about the application of anchoring vignettes in the analysis of Czech upper secondary school students’ self-assessment of ICT skills. The pilot study was conducted in December 2017 with 166 respondents from four different types of upper secondary schools. Anchoring vignettes, which are brief texts describing hypothetical people who illustrate a certain level of the trait of interest (e.g. information and communication technology (ICT) skills), is a method implemented to identify response scale differences in survey questions and to adjust self-assessments caused by response scale differences. Methodologically, as there are only a few examples of the application of this method in the self-assessment of ICT skills and also in educational research, this pilot study has enabled the researchers to test how comprehensible a questionnaire with a set of vignettes was for the upper secondary school students. This enhanced research method based on anchoring vignettes will be used for the main study in spring 2018. The pilot study findings confirmed the high variability of the use of scale for respondents’ self-assessments and vignettes.