To ensure adequate skill development, but also competitive advantage as a software engineering organization, initiatives in cybersecurity training is one of several important investment decisions to make for management. This study builds upon three case organizations in Sweden and Greece, where managers’ and software developers’ perceptions on trialability and observability effects are analyzed, grounded in the theory of innovation diffusion. Using interviews and a developer-centric survey, both quantitative and qualitative data are collected, and used in combination to support the development of a pre-investment framework for management. The analysis includes thematic analysis, cosine similarity comparison, and, to some extent, sentiment polarity scoring. A pre-investment framework consisting of a process of seven concrete steps is proposed, based on the empirical findings in the study.