I’m writing an adventure at the moment, which features an organisation called the Reclamations Agency, the state sanctioned thieve’s guild. Most people know a bit about them, but do your characters know a little more? What’s the skill check for this? D&D lacks any kind of Culture (Starfinder) or Street Skills (Shadowrun).
A dry Int check might be the easiest thing to reach for but the problem is that they’re pretty boring. We can do better.
Both the PHB (page 175ish) and DMG (page 239ish) talk about using different ability scores skills, which potentially allows using proficiencies in surprising ways.
To intuit why the Agency works a certain way, I might suggest Insight (Charisma); understanding the social protocols you’ve spotted and trying to understand why they might work like that. Or even Insight (Intelligence) to piece together the clues you’ve collected so far. Deception (Intelligence) to make use of your knowledge of the underhand methods you’d use to sneak something out the city.
The problem is that all these require a bit more maths from the player. They don’t have these numbers written on their sheet already. If you find you’re using them often (or want to persaude your DM to start usign them), you could always note them down though. After all, the DMG says:
If a player can provide a good justification for why a character’s training and aptitude in a skill should apply to the check, go ahead and allow it, rewarding the player’s creative thinking.
Here are some more ideas:
| Acrobatics (Int) | * How difficult does that climb look? |
| Animal Handling (Int) | * Should the animal be behaving like that? * How much weight can this owlbear carry? * Can a druid turn into something like that? * Is that a beast or a monstrosity? |
| Arcana (Cha) | * Is that person charmed? |
| Athletics (Int) | * How long would it take to run that far? |
| Athletics (Wis) | * How strong is that guy? |
| Deception (Con) | * Can I hide how gross this food is? |
| History (Wis) | * Does that sound like something the Queen would have done? |
| Insight (Cha) | * How does this social structure work? |
| Intimidation (Str) | * Can I punch the wall to scare the guy? |
| Investigation (Wis) | * Does anything feel off here? (More active version of Perception (Wis). |
| Medicine (Con) | * Will I get poisoned if I drink this much ale? |
| Nature (Cha) | * Can I say the right things to persaude this Dryad? |
| Perception (Str) | * Is that guy pulling his blows? |
| Performance (Int) | * Can I remember the correct thing to say here? |
| Persausion (Con) | * Can I out drink this Dwarf to win her respect? |
| Religion (Cha) | * Can I fool this bumkin into thinking I speak the words of a god? |
| Sleight of Hand (Wis) | * What are my odds of pick pocketing that person? |
| Stealth (Wis) | * I do think I’ve been spotted? |
| Survival (Str) | * Can I pull this bear trap off my leg? |
Other than just filling in gaps where the D&D skills are lacking, this also lets the PCs have more utility. The paladin might not be intimidating in most situations, but when the time comes for a religious intimidation, their Religion (Str) check might be pretty imposing.