The present research explores how real-time communication data can be used to predict human performance of Air Traffic Management personnel, and ultimately risk in the U.S. National Airspace System (NAS). In three 25-minute simulated Human-In-The-Loop scenarios of varying complexity, two of twelve retired air traffic controllers worked arrival flows landing at Sky Harbor International (KPHX) under current day operations. During these scenarios, data were collected from several dimensions of operational performance defined by breaches in separation minima, controller-pilot radio communication, and both indirect and subjective measures of workload. Relationships among these variables are presented with focus on communication patterns associated with declines in operational performance during high workload. Preliminary results suggest more frequent separation breaches in both high workload conditions, one with with over three times as many separation breaches as the lower workload condition. We discuss next steps in linking the complex multifactorial dynamics associated with human performance to assessing those dynamics in real-time.