How To Unlock: Successfully persuade, bribe, and intimidate.
Throughout the world and during conversations you’ll be given the chance to choose how you respond, whether that’s persuade someone, bribe someone or intimidate someone. Just do one of these successfully for your achievement. There’s a good chance that intimidate (and maybe even persuade) won’t work early on, and that’ll be because your speech level won’t be high enough, so sell loads of items, buy loads too, and even your unsuccessful persuades/intimidation dialogue responses will result in speech skill points, helping you raise your speech level. There are plenty of options around, just make sure you do loads of side missions and such to get more opportunities.