Unitary processes allow for the transfer of work to and from Hamiltonian systems. However, to achieve non-zero power for the practical extraction of work, these processes must be performed within a finite-time, which inevitably induces excitations in the system. We show that depending on the time-scale of the process and the physical realization of the external driving employed, the use of counterdiabatic quantum driving to extract more work is not always effective. We also show that by virtue of the two-time energy measurement definition of quantum work, the cost of counterdiabatic driving can be significantly reduced by selecting a restricted form of the driving Hamiltonian that depends on the outcome of the first energy measurement. Lastly, we introduce a measure, the exigency, that quantifies the need for an external driving to preserve quantum adiabaticity which does not require knowledge of the explicit form of the counterdiabatic drivings, and can thus always be computed. We apply our analysis to systems ranging from a two-level Landau-Zener problem to many-body problems, namely the quantum Ising and Lipkin-Meshkov-Glick models.