An in-depth case study approach was followed and data were collected by means of nine semi-structured interviews with experts from six case organizations. Our findings indicate that gamification of work can be a promising path for working organizations and can be beneficial to both employers and employees. The success of gamification at the workplace is dependent on whether its implementation is able to fulfill employees’ psychological needs for competence, autonomy, and relatedness. To make the most out of gamification at the workplace, employers, supervisors, and employees themselves should pay ample attention to its conditions (i.e., personal preferences of the employees, their demographic characteristics, their need for psychological safety, and the purposefulness of the game). In addition, seven psychological mechanisms underlying successful performance were found in our empirical work (i.e., competition, intrinsic incentives, extrinsic incentives, choice, social interaction, feedback, and ownership). The properties of gamification schemes that also have to be dealt with by the parties involved comprise their duration and intensity, the inclusion of a facilitator, the type of equipment, and scale referring to the size of the gamification scheme. Finally, our study has provided more insight into the possible effects of gamification schemes (i.e., increased insight in the workflow and, through this, a better understanding of both the employees’ own contributions and of their employers’ contributions to the work processes, the transfer of game elements into work processes, team building enhancement, learning effects, and negative emotions).