Initiative games are widely used e.g. in kindergartens, assessment centers and professional manager training courses. These games traditionally involve a fictional setting and challenge; they rely heavily on the physical aspects of being set in the real world, often even in nature. Their goals and observable aspects are identified and an argument is made for the suitability of mobile device-based applications to enrich such games as well as to facilitate (in-game) evaluation. Recent and ongoing research in related fields is considered to strengthen the argument for the use of mobile devices in the field of experiential education.