Organizations strive to ensure and maintain the reliability, safety, security, usability, and competitiveness of their processes, goods, and services. Improvement of employees’ skills and abilities contributes to these ends and is a relevant issue for the field of human factors. However, going a step further than designing ergonomics, implementing protocols, and conducting training is the attempt to enhance employee skills directly through various technological means. So-called Human Enhancement aims at direct technological interference with the employees’ skills and is a notoriously controversial yet deeply historical phenomenon. Drawing from empirical and theoretical literature on Human Enhancement, we seek to provide an initial analysis of this phenomenon in an organizational context. One motivational aspect of contemporary Human Enhancement is the need to meet internal, often self-related, or external, usually social or organizational, demands. Given the different effects and means of Human Enhancement, some forms are illicit, sanctioned, and/or condemned as morally wrong, while others are obligatory and well-established. Enhancement efforts can be based on individual initiative and, hence, without organizational knowledge. The opposite of the spectrum are enhancements applied by organizational order. We also emphasize how an organizational culture may incentivize engagement with illicit means of Human Enhancement. Potentially linked to safety and security-related aspects, its enhancement effects in relation to these two poles can inform stakeholders in their regulatory decisions.