We demonstrate how simultaneous measurements of conductance and force can be used to monitor the step-by-step progress of a mechanically-activated cis-to-trans isomerization single-molecule reaction, including events that cannot be distinguished using force or conductance alone. To do so, we simulated the force-conductance profile of cyclopropane oligomers connected to graphene nanoribbon electrodes that undergo a cis-to-trans isomerization during mechanical elongation. This was done using a combination of classical molecular dynamics simulation of the pulling using a reactive force field, and Landauer transport computations of the conductance with nonequilibrium Green's function methods. The isomerization events can be distinguished in both force and conductance profiles. However, the conductance profile during the mechanical elongation distinguishes between reaction intermediates that cannot be resolved using force. In turn, the force signals non-reactive deformations in the molecular backbone which are not visible in the conductance profile. These observations are shown to be robust to the choice of electrode and Hamiltonian model. The computations exemplify the potential of the integration of covalent mechanochemistry with molecular conductance to investigate chemical reactivity at the single-entity limit.