Group-velocity matched cross-phase modulation between a fundamental soliton and a dispersive wave packet has been previously suggested for optical switching applications similar to an optical transistor. Moreover, the nonlinear interaction in the resulting group-velocity horizon can be exploited for adiabatic compression of the soliton down into the few-cycle regime. Here, we study the delicate phase- and frequency-matching mechanism of soliton/dispersive wave interaction by controlling the input chirp of the dispersive wave. We demonstrate that such a modification of the dispersive wave can significantly alter the soliton dynamics. In particular, we show that it allows a decrease of the fiber length needed for the best compression and, to some extent, control of the trajectory of the soliton. The mechanism of such an influence is related to the modification of the phase-matching condition between the soliton and dispersive wave.