Electronic health record (EHR) documentation serves multiple functions, including recording patient health status, enabling interprofessional communication, supporting billing, and providing data to support the quality infrastructure of a Learning Healthcare System. There is no definition and standardized method to assess documentation quality in EHRs. Using a human-centered design (HCD) approach, we define and describe a method to measure documentation quality. Documentation quality was defined as timely, accurate, user-centered, and efficient. Measurement of quality used a virtual simulated standardized patient visit via an EHR vendor platform. By observing and recording documentation efforts, nurse practitioners (NPs) (N = 12) documented the delivery of an Age-Friendly Health System (AFHS) 4Ms (what Matters, Medication, Mentation, and Mobility) clinic visit using a standardized case. Results for timely documentation indicated considerable variability in completion times of documenting the 4Ms. Accuracy varied, as there were many types of episodes of erroneous documentation and extra time in seconds in documenting the 4Ms. The type and frequency of erroneous documentation efforts were related to navigation burden when navigating to different documentation tabs. The evaluated system demonstrated poor usability, with most participants scoring between 60 and 70 on the System Usability Scale (SUS). Efficiency, measured as click burden (the number of clicks used to navigate through a software system), revealed significant variability in the number of clicks required, with the NPs averaging approximately 13 clicks above the minimum requirement. The HCD methodology used in this study to assess the documentation quality proved feasible and provided valuable information on the quality of documentation. By assessing the quality of documentation, the gathered data can be leveraged to enhance documentation, optimize user experience, and elevate the quality of data within a Learning Healthcare System.