We explore a set of jet substructure observables that use grooming techniques such as the Soft Drop procedure by performing simulations with the hybrid strong/weak coupling model for jet quenching. The results obtained for the observables presented in this proceedings, namely the number of Soft Drop splittings, or $n_{\rm SD}$, and the sharing momentum distribution $z_g$ for different angular cuts between the two main branches in a jet, can be easily understood as arising from the fact that among all the jets with a given jet $p_T$, those jets which are wider in opening angle, meaning that they have a higher jet mass and come from showers featuring more splittings, tend to lose more energy than the narrower jets. We comment on the comparison to data from ALICE and CMS, and point out the caveats arising from the consideration of smearing effects due to the presence of a large fluctuating background.