Biomedical engineers integrate user needs into medical device design, extending beyond clinical conditions to consider users’ skills and capabilities, to understand potential hazardous situations linked to human error, and to ensure that the end user is confident in the use of the technology. However, in Healthcare 5.0, usability and prevention of human errors are not enough, and trust in the technology, based on transparency, accountability, and explainability, is also required. Thanks to the literature and the state of the art, integrated with the analysis of the complex European regulatory landscape, three key aspects of a human-centric design have been identified and tools to measure them are proposed, covering the need in Healthcare 5.0 to have a personalised approach for identifying user needs, preventing human error, and preserving and enhancing trust in the technology. The first tool evaluates user needs in Healthcare 5.0, and measures the digital autonomy (digital fragility) of an end user. The second tool evaluates clinical, societal, and informational risks related to the use of the technology and measures the impact of human errors on technology safety and efficacy. The last tool is intended to measure trust, a cornerstone of the healthcare setting to be preserved also when AI systems are introduced into the equation.