Not sure if this is still relevant, but I've managed to get the last 7 dialogues that I needed for the achievement, in a row and within the same instance, by using the following strategy:
Trigger the dialogue with the warrior NPCs and wait until the dialogue bar reaches about 25%.
Pick the third option.
Trigger the dialogue with the warrior NPCs and wait until the dialogue bar reaches about 25%.
Pick the second option.
Trigger the dialogue with the warrior NPCs and wait until the dialogue bar reaches about 25%.
Pick the first option.
Repeat the above (third -> second -> first) while waiting for the dialogue to reach 25% until the achievement completes.
Hope this helps.