End-user trainings account for an important part of teaching how to use information systems effectively in practice. This paper examines which individual characteristics and differences between end-users can be leveraged to improve end-user trainings further. Therefore, relevant literature on end-user trainings is used to define relationships between individual characteristics (i.e. learning styles) of trainees and matching training methods. Following a design-based research methodology, two different end-user trainings are developed in the domain of electronic negotiation support systems to define and evaluate design principles and theories for individual end-user trainings. The trainings follow either an exploration-based approach or an instruction-based approach. For the evaluation of these trainings a general concept implementing a negotiation experiment assessing learning outcomes and acceptance of the target information system is developed and first descriptive results are presented.