In this video guide I will show you how to use dialog skills 30 times in conversations. Now a few things to make this easier. If you start out your character with increasing your personality right away. Also if you keep putting points into your dialog skills will help as well
. There is one perk to increase dialog, but that is it. Keep in mind some companions have increased dialog skill that will help you out.
When in a conversation and get the option to: lie, persuade, or intimidate
will be where the achievement progress will come from. The number next to it is the level you need to succeed at getting it. Make sure to exhaust people's dialog for more chances to get the achievement. Also using the disguise in restricted areas while failing will prompt more dialog options. One other way is to steal something out in the open where they can see you. Once they see you they will confront you about it, you will then have dialog options. Once you hit 30 the achievement will pop.