Radiology specific clinical decision support systems (CDSS) and artificial intelligence are poorly integrated into the radiologist workflow. Current research and development efforts of radiology CDSS focus on 4 main interventions, based around exam centric time points–after image acquisition, intra-report support, post-report analysis, and radiology workflow adjacent. We review the literature surrounding CDSS tools in these time points, requirements for CDSS workflow augmentation, and technologies that support clinician to computer workflow augmentation. We develop a theory of radiologist-decision tool interaction using a sequential explanatory study design. The study consists of 2 phases, the first a quantitative survey and the second a qualitative interview study. The phase 1 survey identifies differences between average users and radiologist users in software interventions using the User Acceptance of Information Technology: Toward a Unified View (UTAUT) framework. Phase 2 semi-structured interviews provide narratives on why these differences are found. To build this theory, we propose a novel solution called Radibot—a conversational agent capable of engaging clinicians with CDSS as an assistant using existing instant messaging systems supporting hospital communications. This work contributes an understanding of how radiologist-users differ from the average user and can be utilized by software developers to increase satisfaction of CDSS tools within radiology.