During last years, budgets for training within ICT organization decreased, in particular for F2F (face-to-face) sessions. A traditional, institutional, serious manner for providing training is still adopted, and it reduces the possibility for attendees to approach to training sessions as a moment for learning but also for stimulating their creativity and generate new ideas to be used in their daily work. From an organizational viewpoint, well-known maturity models position such KM-related processes at highest maturity levels (e.g. OID process area in CMMI at ML5), but using a continuous representation, it can be done (and it would be desirable) yet from lower levels. This paper proposes a different way - called ‘Play’n’Learn’ - to verify people knowledge using games, contextualized to Software Management & Measurement issues, at the end of training sessions as part of a continuous knowledge management process for achieving higher maturity and capability levels, according to most known maturity models (MM) such as CMMI and ISO 15504 (SPICE).