Working patterns have been changing rapidly in the recent years due to the technological advancements, environmental concerns and many other influences. The change in working behaviours comes along with several benefits but holds many challenges for companies and organizations. Companies which fail to meet the new requirements and continue to promote an old-fashioned working environment are facing problems to compete in today’s markets. The trend goes towards a merger of personal life with the job, creating new demands for more flexible, remote and individual working conditions. Digital technologies are not only used to automate processes, but they are also used to enable collaborative working styles by removing the boundaries of time and place. New Work is an emerging term for describing these changes. The topic is rather diverse and no universally accepted definition for the term exists. This research study aims to investigate the challenges of a New Work transformation and it proposes a New Work self-assessment tool as a possible solution to tackle some the uncovered challenges. The tool allows for an assessment of the current situation of a company regarding the several areas that are affected by New Work. The results mark a possible starting point for a New Work transformation. The concept for the tool is developed based on the design science research methodology, aiming to create a valuable resource for transformational guidance.