The energy transition introduces new technical standards, laws and regulations regarding the stability and reliability of energy grids and systems. Due to the non-existence of a measuring standard, key performance indicators (KPIs) were developed to enable the measurement and comparison of individual energy grid (namely electricity, heat and gas grid) and system supportabilities while also promoting well-founded decision-making and optimization efforts. Inconsistencies in definitions concerning fundamental energy terms and the correlations between them inhibit the effective usage of the KPIs. Therefore, the overarching issue of the security of energy supply and its related subjects were also approached. The primary subject of this paper is the development of two new KPIs to measure and compare the energy grid and system supportability. These KPIs are based on spatio-temporal conditions in their respective grids. The usage and benefits of the developed KPIs are exemplarily highlighted by analyzing the impact of a scenario with the integration of a large-scale heat pump into the electricity and heat grid. The energy grid supportability is determined for each grid, whereas the energy system supportability takes the interactions of the electricity and heat grid into account. The developed KPIs are intended to enable stakeholders to identify areas with optimization potential in energy grids and systems. Moreover, the KPIs can be used to create a standardized evaluation method for regulatory requirements.