As you progress through the story you get to the San Mateo region.
One of the main missions called The death truck
requires you to stop a truck and interrogate the driver.
There is no escort just the truck by it self and all you have to do is pull the driver out of the truck and interrogate him.
This counts towards the achievement.
When you done just fast travel to nearest safe house and replay the mission. Do this as many times as you need till you pop the cheevo.
It only takes couple of minutes to complete so super easy way to get this done.
Hope it helps
PS. This is my first guide so be gentle.