The radical character of molecules exhibiting singlet fission is related to the energy level matching relationships that facilitate this process. Using a linear H4 model molecule, we employ quantum chemical topology descriptors based on full configuration interaction calculations to rationalize singlet fission. In this context, the influence of the closed-shell to diradical and diradical to tetraradical character on the singlet fission energy matching conditions is analyzed. We find that in the diradical limit the singlet fission efficiency can be manipulated considering the active molecule coupled to an excited diradical, while in the diradical to tetraradical limit, the efficiency is dependent only on the gap between the lowest-lying excited singlet and triplet state. Furthermore, our results reveal possible design strategies for molecules with radical character exhibiting efficient singlet fission.