This chapter provides an insight into how observational measures can contribute for determining attitudes and competencies towards Information and Communication Technology. To get an idea of the capability of observational measures the first part of this chapter outlines the meaning of observational techniques as a tool of research and explains what is important when planning an observational study. For a better understanding in this context, several video- and audio-supported observation techniques are presented, as well as advantages and challenges of observational techniques in general. The second part of this contribution focuses on the methodology and on particular findings of ERIC-referenced empirical studies that researched attitudes and competencies towards IT by using observational techniques. After reviewing those studies and summarizing their findings, this chapter ends with the conclusions that observational measures as part of a mixed methods research design have the potential to deliver meaningful, unique data and findings. One of the major findings is that attitudes and competencies toward IT tend to be positive in most of the reviewed studies.