Yup, I hear ya. Social conflicts can be more difficult to run, and the nature of the game encourages finding other ways to resolve situations like tricking or convincing.
In regards to asking questions, yes, one way or another you have to get to the point where the player’s objective is clear and everyone at the table is aligned with the stakes of the conflict. You can simply ask them directly, or, you can roleplay through it. Just keep going if you are comfortable with dialogue. Once both sides have a clear case, then go into a versus test or conflict (if appropriate).
Regarding when to call for dice, it is the point in which you cannot continue the race or the fight or the argument without settling it any other way. But, don’t let the players push you into a conflict when there is none. That gets back to Thor’s reply in the other thread, where the players cannot just generate a test or conflict where there is none. To be clear, their actions MAY lead to a conflict, but only you can see the next step of the situation. Players cannot assume their actions will even generate a conflict, and they cannot presume to know where the obstacle is (although you can bet they will try).
If you have prepped the adventure well, you should have a good understanding of the opponent’s motivation/instinct. This is absolutely essential to figuring out where the obstacles really are (where appropriately fitting). Understanding the purpose of a conflict is the first step in determining where to draw that line.
Let’s look at the example of the previous dragon scenario.
The situation is that the party has to convince an elder red dragon to not eat a village. The dragon’s instinct is to always sleep with one eye open. From this, we can tell 1) she listens to Metallica and 2) is paranoid about hobo adventurers stealing her precious treasure. In the fiction, she is about to lay some eggs soon, and mama is HUNGRY. She’s already eaten all the village’s livestock, and the townsfolk have hired the party to make sure the dragon doesn’t eat them next.
Here, the party comes upon the dragon in her lair. They have no hope of killing this dragon, and the dragon knows it. Luckily for them, her belly is full, and she is satiated. Otherwise, they’d be toast.
As the adventurer leader lays down her sword, the dragon watches carefully. The party delivers a few lines of dialogue stating they come in peace and have an offer she “can’t refuse.” This is important because the dragon feels not threatened and stands to profit. She’ll hear them out.
Ultimately, the group has a plan and wants to convince the dragon to eat the goblins in the valley, and the villagers will bring her a steady tribute of animals and thralls each year. But, all of that is the stuff of the conflict. They still have that in their back pocket. This is going to be a hard sell, after all, the dragon could just eat all of them anyway. This is going to take some work, and a compromise of some sort is almost a certainty given the disparity between the party’s dice pool and the dragon’s. This means that, as the GM, you are pretty sure a conflict is on the horizon. But, we still don’t know what the players will do, so we play on.
Now, let’s say one of the players is not onboard with all of this and instead wants to trick the dragon. This is great roleplaying fodder. Don’t go into the conflict yet. The dragon could just sigh and mutter something like, “Oh, won’t you pesky humans figure it out and get back to me. But, don’t take too long…” Then, she smirks as she lays her head back down while the party keeps roleplaying.
On one hand, the tricky character could be a part of the convince conflict, but those lines of dialogue would be Feint or Maneuver actions. The spirit of the conflict is still to get the dragon to agree to the original terms. So, even though this character is trying alternative tactics, it fits within the larger strategy of “the offer.”
On the other hand, the party could roleplay to get the other character to agree with the original plan of the sacrifices.
Either way, there is consensus, and the adventure leader resumes the conversation with the dragon, “Ok, we’ve got an offer…”
At this point, everyone knows what they are going for. Anything beyond this point is dialogue that can play out through the conflict. Say, “OK, this is going to be a Convince conflict. If you win without compromise, the dragon will accept your offer unconditionally. If you lose, the villagers are in trouble.”
Most likely, there will be some major compromise. If the players win with compromise, the dragon might demand quarterly sacrifices from the town instead of annual, and that the party capture the goblins for her (because she doesn’t want to risk injury at this time).
If, alternatively, all the players started on the same page when they met the dragon, I would have let the initial conversation go back and forth. Even if the leader lays out the terms, there is still more to haggle over. I’d foreshadow that the dragon has a nearly insatiable appetite: “What, you think a meager annual tribute is enough?” I’d call for the conflict right after that line because I’ve set some expectations with the players. Now, this conflict becomes about what the party has to agree to and negotiate the details.
As far as fight conflicts go, the same thing applies. If the players rush into battle, you could call the conflict there. Sure. However, every once in a while, you can build up to an even greater climatic moment by continuing to roleplay. Let some arrows fly and some swords clash. Just go back and forth once or twice. This is not just fluff. You are clarifying through roleplaying. You are exploring the players’ intent and giving them opportunities to adjust before determining the conflict type. Doing it this way makes sure everyone is aligned. Plus, it builds up some excitement and momentum that will be needed to carry the group through the rest of the conflict.