The world in which we work is changing. Information and communication technologies transform the work environment, providing the flexibility of when and where to work. The New Way of Working (NWOW) is a relatively new phenomenon that provides the context for these developments. It consists of three distinct pillars that are referred to as Bricks, Bytes and Behaviour. These pillars formed the basis for the development of the NWOW Analysis Monitor that enables organisations to determine their current level of NWOW adoption and provides guidance for future initiatives in adopting NWOW practices. The level of adoption is determined from both the manager’s and employees’ perspective as they might have a different perception and/or expectations regarding NWOW. The development of the multi-level NWOW Analysis Monitor is based on the Design Science Research approach. The monitor has been evaluated in two cases, forming two iterations in the design science research cycle. It has proved to be a useful assessment tool for organisations in the process of implementing NWOW. In future research the NWOW Analysis Monitor will be used in quantitative research on the effects of the implementation of NWOW on the organisation and its performance.