Organizations that integrate new technologies, such as collaborative robots, often struggle to maintain workers’ psychological well-being during transitions. Integrating new technologies can, in fact, negatively impact job satisfaction, motivation, and organizational culture. It is thus essential to prioritize workers’ psychological sustainability to benefit fully from these technologies’ advantages, such as reduced production times and increased flexibility. This study evaluates the impact of eight guidelines designed to support organizations in optimizing human–robot collaboration. The guidelines focus on safety, training, communication, worker agency, and stakeholder involvement. We investigated possible implementation solutions and assessment methods or KPIs for each guideline. We conducted an online survey targeting experts in robotics to gather opinions on the guidelines’ potential impact on workers’ psychological well-being, safety, and performance. The survey also asked about implementation solutions and KPIs for evaluating their effectiveness. Proposed solutions, such as demonstration videos and hands-on training, have the potential to enhance users’ perceived safety and confidence in the system. KPIs, such as subjective perceived safety, risk assessment, and user satisfaction, can be employed to assess the success of these implementations. The study highlights key strategies for ensuring workers’ psychological well-being, optimizing performance, and promoting a smooth integration of robotic technologies. By addressing these factors, organizations can better navigate technology integration challenges, fostering a more sustainable and human-centric approach to deploying robotic systems in the workplace.