When developing an Adaptive Learning System (ALS), users are generally consulted (if at all) towards the end of the development cycle. This can limit users’ feedback to the characteristics and idiosyncrasies of the system at hand. It can be difficult to extrapolate principles and requirements, common to all ALSs, that are rated highly by users. To address this problem, we have elicited requirements from learners and teachers across several European academic institutions through explorative, semi-structured interviews [1]. The goal was to provide a methodology and an appropriate set of questions for conducting such interviews and to capture the essential requirements for the early iterations of an ALS design. In this paper we describe the methodology we employed while preparing, conducting, and analyzing the interviews and we present our findings along with objective and subjective analysis.