Fixing Charm/Charisma Checks
Several commentators on roleplaying have mentioned that Charm rolls (or Charisma checks, or whatever you game calls them) are odd ducks among the rolls that players make because they follow a different set of rules. When you want to hit someone with an attack, you roll the dice and ask if you hit the required difficulty. When you want to know if you remember a given fact or successfully toss the dwarf, you roll the dice and ask if it hit the difficulty. This is normally how actions are resolved.
But when you want to deceive someone, we ask the player to say what they say, we weigh what they said, and then the difficulty is set/an opposed roll is made, and we might penalize/reward the player for what they said. So this has led some to question why we resolve Charm/Charisma rolls "in reverse," describing the action and then rolling, instead of rolling and then describing what they said.
And this is a good point - it makes it a whole different animal, and the kind of thing where traiting well in talking isn't enough: you have to actually do something as the player to help your character engage well as the Party Lip Man.
So this led me to consider three different routes for resolving Charm rolls, as I think a simple yet effective system might be best to remove ambiguity and reward a player for trying something new: talking things out with an NPC. But you also want a system that works well for you and your group, so hopefully one of these will meet your needs.
I. System 1: The Skill Check
Skill checks make for fast and efficient resolutions of actions: aim for this difficulty, and you want to get more successes than failures. Different games do this differently but the goal is the same: get people to make different types of rolls to contribute to a successful action.
If I am GMing a group and we do a skill check, there are a few things I'd make sure to do. First, no matter whose plan it is to attempt the Charm/Charisma roll, everyone makes a roll toward the skill check. This does three things. First, it encourages the players to be involved: they all have to do something about this check. It could be that they distract the mean guard so that the Lip Man can talk to the more kindly guard. They could play a song to put the guards in a good mood, or offer them a drink. Whatever the party member does, if it could reasonably help, they perform the roll, adding successes to the total number of successes, and failures to the number of failures. If the party gets, say, 4 successes before they get 3 failures, they win: the Charm attack works.
A player might just choose not to join them and wander off, in which case allow that to happen: don't force the player to help. If they don't want to, go for it, but tell the table that the guards would be used to seeing 1-2 people try to convince them to let them pass, and that will be highly suspicious (aka, opting not to help is an automatic failure to the check). If they want to abandon them, let them do that - but it will only make it harder for them to succeed.
No matter what they do, we are keeping them engaged, increasing the tension if they don't act, and forcing them to think about ways to help the group.
The second thing this does is it builds party cohesion. The best part of a traditional tabletop RPG is the camaraderie: there's nothing quite like rolling dice with friends around a table. And this keeps what would likely be a one-man show into an activity for the whole group.
But the final thing it does is it removes the whole issue of the "Charm Nuke": if the player makes one good roll they magically charm the person into doing what they want. That's not how life works (typically), and that's not good for storytelling, as it will encourage people to play to the math instead of being immersed in a world. The nature of this system is that a single roll is not enough: you need four (or however many you set) to succeed, and that means you need to do more than just roll well on one roll. So you get out of the "Jedi Mind Trick" crisis that GMs sometimes face by the use of a system that implicitly says, "One action in a vacuum is not enough: work together."
II. System 2: The Standard Difficulty
An alternative option, if you don't want Charm rolls to slow things down, is you can do the exact same thing but with a standard difficulty for the Lip Man only. So you could tell the player, "Okay: you need to make three successes before you get two failures, and every success you have will reduce the difficulty slightly, and every failure with increase the difficulty heavily. What will your first action be?"
This does two things. First, it does make it easy to resolve, quick to complete, and keeps the focus on the Charm Cannon of the group (because if that's what the person does really well, it can be nice to give them the limelight for a bit). The other thing it does, though, is it allows for that "personal journey" in making the sale. You have to start off winning trust, and then make the close. Having one person do a few rolls instead of just one roll makes it feel more real, and it means that a single good roll is not enough to convince a guard to leave his post for a few minutes.
The issue with this approach, as we said above, is that it does make the encounter a one-person encounter, so be mindful of how long it goes. Give the Charm Cannon a moment in the spotlight, but keep it to a moment.
III. System 3: The Opposed Roll
It's worth noting that you can, in fact, use an opposed roll well, which is what most people probably do: the character rolls their Charm/Charisma roll, the target reacts with their roll to resist it, and we compare the final results. This is not bad: in some situations this is a fast and easy way to resolve it.
A few situations that I think work better for opposed rolls: when done in combat, it feels right to make it as an opposed roll. A guard who is just keeping watch is more likely to take a beat to consider the ramifications of following what a stranger says (getting whipped/losing his home/losing his job for leaving this post, for example), whereas if there is blood and gore around that same guard, he might give in to an Intimidate check, regardless of the consequences, if it's strong enough.
Second, when you try to play a player, an opposed roll is a good idea. We see this done really well in the TV show Firefly when a former companion tries to seduce Inara: a person who is used to the tricks of the trade and is on her guard against such tactics. Make the opposed roll: see if they find the vulnerabilities of the target, and if they don't, make the penalties more severe. Thieves don't let other thieves go when they try to steal from them, so raise the stakes.
And of course, this would not be a complete post if we didn't mention that there are some times where a roll is not needed at all. If a guard, making a modest wage, sees a host of his comrades die and he is worried for the lives of his family, he might just let you in without you needing to ask. Similarly, if you really want the king to step down from his throne, there is almost no reason why that request would ever work; the roll (no matter how high) would never cause it to succeed. So don't feel like you have to require a roll: some things in life just don't work out, no matter how well you spin it.
Until next time,