The strain-induced austenite (γ) to martensite (α′) transformation in AISI 316L austenitic stainless steel, either in powders or bulk specimens, has been investigated. The phase transformation is accomplished using either ball-milling processes (in powders)—dynamic approach—or by uniaxial compression procedures (in bulk specimens)—quasi-static approach. Remarkably, an increase in the loading rate causes opposite effects in each case: (i) it increases the amount of transformed α′ in ball-milling procedures, but (ii) it decreases the amount of α′ in pressed samples. Both the microstructural changes (e.g., crystallite size refinement, microstrains, or type of stacking faults) in the parent γ phase and the role of the concomitant temperature rise during deformation seem to be responsible for these opposite trends. Furthermore, the results show the correlation between the γ → α′ phase transformation and the development of magnetism and enhanced hardness.