On-line media and self-directed learning environments are among the most effective training solutions in terms of cost, time and logistics. In the last few years, the percentage of employees participating in training courses has increased. At the same time, there has been a decline of training budgets. Therefore, careful educational controlling must guard direct and indirect costs listed by amount, mode and source. Additionally, the success of on-line courses must be measured in terms of training and functional sectors. Most educational departments generally use controlling processes which consist of consecutive phases. Modern economic controlling, however, focuses on the permanent improvement of process outcomes. Recent examples of Web-based training courses and on-line tools illustrate how continuous feed forward and feed backward loops may be implemented in on-line learning. Controlling the transition from learning to working and checking the sustainability of learning outcomes improves the quality and success of training and makes it possible to calculate the success of training applications. Thus, modern educational controlling approaches should be introduced which comprise exact calculation of financial investments and gains, optimal planning of organisational processes and goaloriented definitions of strategical and operational learning objectives. Web-based training will then allow the educational and IT staff to take over a strategical role to establish an innovative learning and working culture.