Industry 4.0 needs the help of technology 4.0 to improve production apparatus flexibility and productivity and decrease non-quality costs. However, these technologies aren’t well integrated in already existing processes because we try to correlate the technology to the norms and standards we have previously set, in a time when augmented reality systems were not part of the industry’s toolbox, by neglecting, the human factor. Some researchers in ergonomics develop concepts to create a symbiosis between Human and machine in these production tasks. This is notably the case for the paradigm of Enabling Collaborative Situation (ECS) where researchers investigate the collaboration between Human and machine over time. We relied on this paradigm to build a study where we have questioned multiple interactions between a user and an Augmented Reality (AR) device in order to find what kind of features might be considered as relevant to improve the HMIs and the AR devices in the future. This study has been conducted on a training workstation for automotive industry with a Hololens 1. We present in this paper the results of this study and envisage the technical solutions to move towards an ECS through the redesign of Human-Machine Interface. At the end of the paper, we draw the outlines of a future experience where we want to compare, the former HMI versus the new one redesigned thanks to the previous study in a first time, and the Hololens 1 against the Hololens 2 in a second time in order to understand how the new features move to an ECS.