The effect of digitalization and its transformative power in all aspects of corporate strategies and organizations are visible everywhere. As leaders try to make sense of the “digital tornado” and prepare, try out, and set courses in new business directions, the authors propose to take a step back and focus on what is still at the core of corporate change – the people of your organization. In this chapter, the authors reflect on the forces and challenges that employees are facing in times of rapid and digitally driven change. They also mirror this, considering structural, sociological, and demographic change in the workforce, especially with regards to younger employees. They provide a set of fundamental metrics that can quantify the human resource strategy of an organization to derive measures which can be controlled via a DMAIC cycle. This contribution is an extended version of and includes an enhanced set of metrics to address challenges of digitalization and agile work environments. Further, approaches to possible solutions and first steps for an implementation in companies are presented.