Interviews are the most widely used elicitation technique in requirements engineering (RE). However, conducting a requirements elicitation interview is challenging. The mistakes made in design or conduct of the interviews can create problems in the later stages of requirements analysis. Empirical evidence about effective pedagogical approaches for training novices on conducting requirements elicitation interviews is scarce. In this paper, we present a novel pedagogical approach for training student analysts in the art of elicitation interviews. Our study is conducted in two parts: first, we perform an observational study of interviews performed by novices, and we present a classification of the most common mistakes made; second, we utilize this list of mistakes and monitor the students’ progress in three set of interviews to discover the individual areas for improvement. We conducted an empirical study involving role-playing and authentic assessment in two semesters on two different cohorts of students. In the first semester, we had 110 students, teamed up in 28 groups, to conduct three interviews with stakeholders. We qualitatively analysed the data to identify and classify the mistakes made from their first interview only. In the second semester, we had 138 students in 34 groups and we monitored and analysed their progress in all three interviews by utilizing the list of mistakes from the first study. First, we identified 34 unique mistakes classified into seven high-level themes, namely question formulation, question omission, interview order, communication skills, analyst behaviour, customer interaction, teamwork and planning. In the second study, we discovered that the students struggled mostly in the areas of question formulation, question omission and interview order and did not manage to improve their skills throughout the three interviews. Our study presents a novel and repeatable pedagogical design, and our findings extend the body of knowledge aimed at RE education and training by providing an empirically grounded categorization of mistakes made by novices. We offer an analysis of the main pain points in which instructors should pay more attention during their design and training.