This achievement is the very first conversation-related achievement. Like all "conversation battles", Zeke's first line is always answered to with the same response (Empathize in this case), but after that, his responses to Adam are randomized, but this is still an easy achievement to obtain.
You must choose Try to Free Josie to begin the conversation. The first correct choice is "Empathize", but the next two are random. As a general rule, Zeke responds much better to the "Empathize" and "Reason" choices. The achievement will be awarded once the conversation is over, or when you leave the building.
This video shows how you should follow the dialogue.