In this video guide I will show you how to succeed at dialog conversation checks with a single disguise. Going through the game you will automatically get an item called: Shroud
. With this you will find disguises throughout the game to be able to enter restricted access areas. You will know if you have the right one for an area when your in the restricted area and have a purple bar on the bottom of the screen.
Now once you have the right disguise for the area you are trying to get the achievement. Simply keep walking around to diminish the bar. You will notice three small boxes next to the purple bar on the right. These are your chances at dialog before running out. You will need to have some points into the lie, persuade, and intimidate skills to be more successful
at talking your way out of all three. Once you get caught the third time and convince them your not doing anything the achievement will pop.