This cannot be done on any soldier's that do not speak English without you having an interpreter. Therefore I believe the first and easiest way of getting this achievement is on the Side Op "Extract Interpreter (Russian)" which is the first Side Op you unlock. Before using a Fulton on the interpreter hold him up and use LB to select an interrogation option, once you have done this the achievement should unlock.
This will also unlock the "Undertaken" achievement for completing a Side Op.