Liberated: Enhanced Edition

There are only 3 opportunities to respond arrogantly, so you can't skip any of them. They are all in Issue 01 near the beginning of the game. They're impossible to miss, just make sure to pick arrogant before the timer runs out

2 responses come when you are being interrogated and the game gives you the option to be polite or arrogant twice in quick succession.

Later, during your first operation with the Liberated, you'll be in a van with the tech guy and have your 3rd choice. This time the choices will be arrogant or friendly. Pick arrogant for the 3rd time and you should get the achievement