The advancement in digital technology is transforming the world. It enables smart product–service systems that improve productivity by changing tasks, processes, and the ways we work. There are great opportunities in maintenance because many tasks require physical and cognitive work, but are still carried out manually. However, the interaction between a human and a smart system is inevitable, since not all tasks in maintenance can be fully automated. Therefore, we conducted a controlled laboratory experiment to investigate the impact on technicians’ workload and performance due to the introduction of smart technology. Especially, we focused on the effects of different diagnosis support systems on technicians during maintenance activity. We experimented with a model that replicates the key components of a computer numerical control (CNC) machine with a proximity sensor, a component that requires frequent maintenance. Forty-five participants were evenly assigned to three groups: a group that used a Fault-Tree diagnosis support system (FTd-system), a group that used an artificial intelligence diagnosis support system (AId-system), and a group that used neither of the diagnosis support systems. The results show that the group that used the FTd-system completed the task 15% faster than the group that used the AId-system. There was no significant difference in the workload between groups. Further analysis using the NGOMSL model implied that the difference in time to complete was probably due to the difference in system interfaces. In summary, the experimental results and further analysis imply that adopting the new diagnosis support system may improve maintenance productivity by reducing the number of diagnosis attempts without burdening technicians with new workloads. Estimates indicate that the maintenance time and the cognitive load can be reduced by 8.4 s and 15% if only two options are shown in the user interface.