We investigate the dynamical mass generation resulted from interaction terms with four chiral super fields. The kind of interactions maybe considered a supersymmetric generalization of the four-fermion interactions of the classic Nambu-Jona-Lasinio model. A four-super field interaction that contains a four-fermion interaction as one of its component terms has been the standard supersymmetrization of the NJL model for decades. Recently, we introduced a holomorphic variant with a dimension five interaction term instead. The latter is a main target of the present analysis. With the introduction of a new perspective on the super field gap equation, we derive it for each one of the four-super field interactions, using the supergraph technique. Through analyzing solutions to the gap equations, we illustrate the dynamical generation of super field Dirac mass, including a supersymmetry breaking part. A dynamical symmetry breaking generally goes along with the dynamical mass generation, for which a bi-super field condensate is responsible. The explicit illustration of dynamical symmetry breaking from the holomorphic dimension five interaction is reported for the first time. It has rich and novel features, which would be easily missed without the super field approach developed here. We also discuss the nature of the bi-super field condensate and its role of the effective Higgs super field picture for both cases, illustrating their difference. Note that such a holomorphic quark super field interaction term can successful account for the electroweak symmetry breaking with Higgs super fields as composites.