Abstract: Techniques described herein relate to analyzing data systems to detect data deficiencies and generating user interfaces for performing user communication sessions to resolve the data deficiencies. A data system may include components and implement operations to analyze a related set of data to determine when to initiate a communication session with a user to resolve a data deficiency. The data system also may be configured to generate user interfaces customized based on particular users and/or particular associates to allow the associate to interact with the user to resolve the data deficiency. The data system also may determine when to record the communication session, store and/or transcribe the communication session, and/or associate the stored communication session records with the corresponding data in the data system.