Software and system development is complex and diverse, and a multitude of development approaches is used and combined with each other to address the manifold challenges companies face today. To study the current state of the practice and to build a sound understanding about the utility of different development approaches and their application to modern software system development, in 2016, we launched the HELENA initiative. This paper introduces the 2nd HELENA workshop and provides an overview of the current project state. In the workshop, six teams present initial findings from their regions, impulse talk are given, and further steps of the HELENA roadmap are discussed.