Achieving fast gates and high-fidelity readout in superconducting quantum circuits often benefits from the use of large amplitude microwave drives. As the strength increases, unwanted effects such as excitation out of the logical states also become more prevalent. In transmon qubits, coherent controls relying on sub-resonant drives are fundamentally limited by the eventual appearance of strong hybridization in the spectrum. Understanding how this threshold depends on intrinsic device parameters is vital for the design and operation of circuits utilizing the transmon as a source of nonlinearity. In this work, we present an experimental study of 14 transmons with a wide range of anharmonicities, and use comparison with Floquet branch analysis and semiclassical simulations to establish a straightforward relationship between the critical value of the effective drive amplitude ηₘₐₓ and the ratio γ=ω_q/α, where ω_q is the transmon frequency and -α is the anharmonicity. For the case where the transmon is used as a parametrically driven coupler, these results further allow us to estimate maximum parametric interaction rates, which informs the circuit design process for optimizing gate rates and fidelities.