A technology landscape may be characterized using a performance characterization that includes scores assigned to performance metrics for the technology landscape and using at least one trained machine learning model. In response to a detected calibration trigger, a calibratable performance metric of the performance metrics may be determined. A relationship may be determined between conforming values of the calibratable performance metric during a conforming period for which the at least one trained machine learning model was trained, and non-conforming values of the calibratable performance metric occurring during a calibration period initiated by the calibration trigger. In this way, a score assigned to the calibratable performance metric may be calibrated, based on the relationship.