Preparation - Violent Questioning
Upon reaching the construction site and interrogating the enemy on the rooftop you will have to get Vincent to interact with the chair and "Push Him Back". Leo must help move the chair. Now, have Leo go to the desk near the wallet and the red door, and there is a spot you can lean over the table even though there is no prompt. Stand here as Leo and wait for about 15-20 seconds. Eventually, a secret cutscene will start, and you have to attack the guy as Leo. The achievement unlocks.
This achievement can be seen in the video guide at 12:39:NOTE:
Achievements are only available to owners of the game. Players using the "Free Trial" friend pass will NOT unlock achievements.