We report from an ongoing study of the design, development, and deployment of an intelligent workplace system in the IT services domain. We describe the system, which is designed to augment the complex design work of highly-skilled IT architects with the use of natural language processing (NLP) and optimization modelling. We outline results from our study, which analyzes feedback from architects as they interacted with various prototypes of the system. This feedback focuses on their sensemaking and uncertainty around: system actions; interactivity and system outputs; and integration with existing processes. These findings point to “explanation” as a multi-dimensional requirement. Such multi-dimensionality requires more careful articulation of the different types of explanations needed to support workers as they make sense of and successfully integrate smart systems in their everyday work practice.