RAW (Resolving Interactions)

Play out the conversation. Let the adventurers make their points, trying to frame their statements in terms that are meaningful to the creature they are interacting with.

Changing Attitude. The attitude of a creature might change over the course of a conversation. If the adventurers say or do the right things during an interaction (perhaps by touching on a creature’s ideal, bond, or flaw), they can make a hostile creature temporarily indifferent, or make an indifferent creature temporarily friendly. Likewise, a gaffe, insult, or harmful deed might make a friendly creature temporarily indifferent or turn an indifferent creature hostile.

Whether the adventurers can shift a creature’s attitude is up to you. You decide whether the adventurers have successfully couched their statements in terms that matter to the creature. Typically, a creature’s attitude can’t shift more than one step during a single interaction, whether temporarily or permanently.

Determining Characteristics. The adventurers don’t necessarily enter into a social interaction with a full understanding of a creature’s ideal, bond, or flaw. If they want to shift a creature’s attitude by playing on these characteristics, they first need to determine what the creature cares about. They can guess, but doing so runs the risk of shifting the creature’s attitude in the wrong direction if they guess badly.

After interacting with a creature long enough to get a sense of its personality traits and characteristics through conversation, an adventurer can attempt a Wisdom (Insight) check to uncover one of the creature’s characteristics. You set the DC. A check that fails by 10 or more might misidentify a characteristic, so you should provide a false characteristic or invert one of the creature’s existing characteristics. For example, if an old sage’s flaw is that he is prejudiced against the uneducated, an adventurer who badly fails the check might be told that the sage enjoys personally seeing to the education of the downtrodden.

Given time, adventurers can also learn about a creature’s characteristics from other sources, including its friends and allies, personal letters, and publicly told stories. Acquiring such information might be the basis of an entirely different set of social interactions.

When the adventurers get to the point of their request, demand, or suggestion — or if you decide the conversation has run its course — call for a Charisma check. Any character who has actively participated in the conversation can make the check. Depending on how the adventurers handled the conversation, the Persuasion, Deception, or Intimidation skill might apply to the check. The creature’s current attitude determines the DC required to achieve a specific reaction, as shown in the Conversation Reaction table.

Aiding the Check. Other characters who make substantial contributions to the conversation can help the character making the check. If a helping character says or does something that would influence the interaction in a positive way, the character making the Charisma check can do so with advantage. If the other character inadvertently says something counterproductive or offensive, the character making the Charisma check has disadvantage on that check.

Multiple Checks. Certain situations might call for more than one check, particularly if the adventurers come into the interaction with multiple goals.