Inexperienced software developers - such as fresh graduates - shape the future of software engineering as a practice. Supporting these novice developers in becoming high quality engineers is a key objective of our engineering community. Yet, inexperienced developers have considerable trouble in applying the fundamentals of systematic software testing in industrial settings. Gaps in testing skills arise from inherent attributes of systematic testing itself and environmental attributes, such as the educational setting in universities. Frustrated, practitioners have long since devised cost intensive workarounds. In this thesis, this problem situation is qualitatively analyzed in great detail, leveraging insights from three Grounded Theory studies. Employing Everett M. Rogers' 'Theory of the Diffusion of Innovation', strategic improvements to the onboarding situation are presented. Lastly, tool support for the strategies developed in this thesis is presented and evaluated.