How can I design this conversational encounter?

Question

I'm GMing a D&D 5e campaign, and my party is about to participate in a noble ball. I'll use an analogy to make my question clear: there are nobles and people in this ball with valuable information and things the players want. Think about those as treasures in a dungeon. I'm having a hard time thinking about how to put monsters and traps to make getting to the treasure room a non-trivial task. I could, of course, design the encounter so that if people are nice to the nobles they simply get what they want. But that's dull.

But I want to design an encounter that contains two somewhat conflicting aspects:

• (i) does not reduce the whole activity to a simple Deception/Intimidation/Persuasion check or something like that. I would like something that rewards good observations and decisions, making the activity fun and engaging for the players.
• (ii) It must be something that is easier for sociable characters to do. After all, maybe I got terrible social skills, but the bard I'm playing is a different beast entirely. I think a successful check should make the activity easier for the player, but not exhaust the situation.

I was thinking in something in the following lines: a good check in Insight might make me, as a GM, explicitly tell the player that the NPC they are engaging has a specific characteristic, like pride, vanity or shyness. But from there I'm having a hard time to think how to make the encounter interesting.

How can I do this within the existing mechanics of the game?

Answer 1

Require multiple successes

A combat-decided encounter doesn't rely on a single roll - there are lots of rolls required (attacks, damage, saving throws, etc). Failure on a roll can be recovered from.

For an encounter decided by social activities, the same should apply.

My usual design for conversational encounters is to use the first-to-three design of death saves.

For example, to obtain the password for the treasure room from Grand Vizier Iznogoud the players must pass three ability checks before they fail three. These could be CHA\Intimidation, CHA\Persuasion, or whatever the players want to try. However, the circumstances of the checks must all be different. They can't just try to intimidate him three times.

I make sure the players know that research will aid these rolls. For example, the players can have advantage on a CHA\Persuasion roll if they talk about fishing. How would they know that Iznogoud is fishing mad? By talking to other guests at the ball (perhaps requiring another ability check).

So, the players might obtain the password by:

1. Sweet-talk the Vizier, using a shared love of fishing as an ice-breaker (CHA\Persuasion? CHA\Deception?).

2. Convince the Vizier they are people of knowledge and influence, by sharing their knowledge of local politics (INT\History?).

3. Trick the Vizier into giving up the password (CHA\Deception).

Answer 2

I did something like this as the conclusion to a campaign a few years ago.

There was a Council of Elders who the group had to convince of something. I wrote up descriptions and personalities for twelve Elders; I thought about what each elder wanted and would be impressed by. Then I gave simplified descriptions to the players, and I went around in a circle asking which elder each of them wanted to talk to.

In each conversation, I'd roleplay the elder asking questions: "are you worthy?" "do you support my goals?" "how will helping you get me what I want?" Then I'd ask the player what skill check they were making (or what else they were trying to do).

Examples:

• One of the elders was a loud-mouthed human noble. The players needed to convince him by appealing to Pride and Honor and similar concepts.
• One was a human wizard, who wanted to make sure they players actually knew what they were doing and that the plan was a good one.
• One was a human merchant, who would vote for any deal that led to an increase in his own wealth.
• One was an elven warrior, who wanted to make sure the plan wouldn't endanger her people.
• One was an elven druid in the shape of a giant bear; the party needed speak with animals to get her vote.
• One was an elven sorceress who didn't care about the plan and just wanted to talk magic for a while.
• One was the orcish warchief, who was basically a figurehead; he offered his vote to anyone who could defeat him in combat
• One was the orcish matriarch, who wanted the humans and elves dead, but would ally in the presence of a greater threat

I forget who the rest of them were. Most of them were silly in some way; the goal was to have a fun experience, not really to challenge the players with the threat of failure.

My players really enjoyed it.

Answer 3

Multi-part Caper

Here is presented some examples of challenges that can arise in a social occasion where the party is trying to accomplish some goal such as theft, assassination, or espionage.

1. Someone has to run interference

   This could involve finding and engaging the host of the party. Keeping their attention despite other activity. It would get progressively more difficult as the host wants to extricate themselves from the conversation.

2. Someone has to sneak away/bribe staff to look the other way.

   To get to something outside of the main party area, someone needs to sneak by, convince, deceive, bribe, or otherwise bypass the staff keeping the party to the approved areas.

3. Someone has to cause a distraction at the right time.

   Breaking into the safe, killing the target, smashing the magic mcguffin, or whatever might cause some comotion. A party member might have to cause a well timed distraction. It could be a combat with a particular party goer, but the character has to lose intentionally, keep the combat to a particular duration, and make it convincing.