To maintain stable power system operation, damping control systems are used in conventional power plants, known as Power System Stabilizers (PSS). However, to derive suitable controller parameters, the current methods require dynamic models that are difficult to maintain and update, and in some cases, might not be available. This makes it challenging for grid operators to maintain system stability when the system is under stringent operating conditions or undergoes the loss of major transmission corridors, which would require a new stabilizer design to provide adequate damping. Leveraging the availability of real-time measurements and "probing" technologies, this paper provides a complementary approach that does not require power system simulation models, but is based on system identification techniques that allow to derive simple and accurate models based on data collected on the system. The proposed method allows to monitor the performance of damping controllers and even to perform redesign based on the models derived with system identification. The resulting redesign could be used to update PSS parameters and improve damping without the need of removing existing damping control systems from service.