There are numerous literature including professional guides that describes how to collect qualitative data, specifically in information systems (IS) studies. In practice, the reality is different from the theoretical academic materials. This is the part where many early career researchers and postgraduate students continue to be challenged, irrespective of theoretical preparedness. This is attributed to unpredicted situation and interaction in subjectivity from both researcher and respondents. As a result, when the factors begin to manifests during the process of data collection, some of the postgraduate students do not know how to address them in practice. This study was undertaken to highlight some of the fundamental challenges and their implications of practice. The qualitative methods were employed in the study, from the perspective of the interpretivist approach. The semi-structured interview technique was applied in the data collection. The data was analysed, using the interpretive method, from which findings were reached. This study advances the approach through which qualitative researches are conducted in IS. Also, it can be used for education purposes through teaching and learning. Also, the study add to the existing literature in the field of IS research. Practically, the model that was developed from the research is intended to ease practical hands-on, and minimise challenges in the collection of qualitative data in IS studies. Also, the study can be used as a teaching case material. The originality and value of this research comes from the methodological guide that it proposes, through which a qualitative data can be gathered and analysed.