To improve human performance, interactive technologies are going towards more automated systems that involve computers, robots and cyber-physical systems into the decision-making process. While automation can lead to increased performance and reduced impact of human errors, interactive technologies without optimal design can have a negative impact on the experience of operators and end-users, leading to suboptimal performance of the automated systems. In this research, we aim to evaluate and refine Human Work Interaction Design (HWID) framework to be applicable in various highly-automated settings including Industry 4.0 environments. This will be performed via a thorough literature review as the first step. The list of identified factors playing a potential role in various interactive systems will then be evaluated and optimised in three case studies. We will try to understand how to maximise collaborations between the users and the machine in interactive systems. A practical approach for evaluating both employees’ and end-users’ perspectives in three scenarios with different levels of automation will be assessed. We will evaluate the outputs in multiple levels of organisations, employees and end-users. The ultimate output of the study will be a framework or model that will help in designing future research studies for various automation scenarios, especially semi-autonomous systems that involve high levels of interaction between users and the machine. We will provide guidelines for implementation of the proposed framework in different scenarios. We expect that the framework output of this research will provide a comprehensive guideline applicable to many Industry 4.0 technologies.