A bit of a chore to do it that way in my opinion, especially if the NPC moves around. If you are not soloing: let one companion speak to the victim. Change to the Thievery companion, position behind the target, sneak and pickpocket with all the time you need. Slender/run away with the thief. Then change back to the speaker, end the talk, let your rest-party be searched, take the excuse with honor, move to the thief and use the stolen stuff. You can even sell it back to the victim.
You can steal only once per party member with Thievery and per NPC. So choose the stuff to steal wisely. Don't steal tier 1 skillbooks for example.
Last edited by geala; 19/09/17 12:26 PM.