Information and communication technologies are rapidly transforming the work environment, providing 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. In this case research three reviews were performed over a one-year timeframe, evaluating the attitude of managers and employees towards the New Way of Working. Special attention was given to the relationship between personality traits (the ‘Big Five’) and satisfaction with NWOW. The case results show that, in general, managers and employees are and remain positive towards NWOW, though the actual effects of the implementation of NWOW on work and the work environment are often limited or hard to quantify. The personality survey shows there is a significant positive relationship between conscientiousness, being (self)disciplined, and satisfaction with NWOW. There is a negative relationship for neuroticism; sensitive employees. This leads to the conclusion that the New Way of Working is not beneficial to all. Where (self)disciplined employees may thrive well in the new work environment, high neuroticism (sensitive) persons may have problems to adapt to the newly gained freedom.