Cunning Diplomat

You never forget names, temperaments, and personalities of people that you meet.

After spending a minute observing a creature, you may make an CHA (Insight) check with a DC of 10 + that creature's deception modifier. If you succeed, you gain advantage on your choice of Insight, Persuasion, Deception, or Intimidation skill checks in all future interactions with that creature. If you fail, you may repeat this check by spending another minute in observation, or you may repeat the check and choose a different skill.