In summary, we have developed a computational model to predict the energy and activation barrier for the activation of dihydrogen at the group 14 element centers in silylenes and germylenes. Establishment of an automated workflow allowed the investigation of approx. 600 silylenes with 40 different substituents. The contribution of each substituent to the reaction and activation energy was found to be additive, allowing for the prediction of the energy values based on simple substituent energy increments. Surprisingly, even energy increments solely based on the elements in α-position to silicon enabled a prediction of the energy profile and thus represents a simple tool for estimating the reaction barrier in head. An accurate prediction of the activation and reaction energies with a mean error of less than 9 kJ/mol is possible via a multivariate linear regression with physicochemical properties of the silylenes in combination with energy increments for the elements in α-position to silicon. Evaluation of the predictive power of this model showed that also the H2 activation propensity of silylenes with substituents not included in the original data set can be reliably predicted, which thus will accelerate the prediction of new silylene structures capable of H2 activation in the future. The same procedure was applied to germylenes and furthermore their reactivity predicted based on the energy profile of the corresponding silylenes.