As you know, nothing feels as natural as the real thing I don't have much more context for you except that it was for convincing someone to do something (they were trying to convince the Lords of Eylea to pay them to help them (at bottom).
I have a simple rule: As soon as the dice are rolled, encounter mode begins. There is a minimum of 3 rounds of OPPOSED checks in most cases (unless I'm just throwing nonsense at them). Why 3 rounds? It feels right and then we know there's a point to it. It's actually quite natural. Its similar to the 3 ACT structure presented in gm's toolkit and her's call, only without all the unnatural filler just to resolve a simple 3-step skill check. ~ Make 3 skill checks and suffer a fatigue or stress as relevant each round they fail. May re-attempt
In this case, over 3 rounds, I have the PCs plead their case (or rather, the "spokesperson for the party" makes his case). Each round they can roleplay the effect (or I can interpret the effect). Additional stresses can occur during the checks. (One of my players detests all the ways that PCs can be "punished" for not succeeding at something. Personally, I think it's absolutely great.)
There MUST be a consequence though. I typically simply use Fatigue or Stress suffered at a rate of one per round (depending on the check). The way that I traditionally set up the # of rounds is simply based on the willpwoer of the opponent. On their own turf, the PCs suffer a penalty die (as noted in the slaanesh supplement).
We can break it down into individual components for example:
* Convincing someone to pay you more money for the job (Haggle works fine for this), and then give you more information after the original negotiation is done (2 sets of checks: one round for haggle, and 3 rounds to try to get information).
* Convincing someone to stop attacking you and listen (parry and skill check), and then convince them that you're not the bad guys and it was all a big misunderstaning (two sets of 3 round checks..since they're being attacked, I allow them perform stunt AND defensive)
Much like negotiation in the real world, when enough stress builds up, they need to step away from the table and begin again the next day
I think without a structure like the above though, it's harder to get an idea of how it works. As the GM if you simply take two sets of 3 rolls, that's probably a great way to start. One of the ways that i do this with skill checks in general is to roll a d30 against all the skill checks and find two (and maybe a specialization) that are relevant (from this thread: www.fantasyflightgames.com/edge_foros_discusion.asp).
2. Animal Handling
4. Ballistic Skill
10. First Aid
17. Magical Sight
19. Nature Lore
29. Weapon Skill
30 Dwarf Engineering
Just like any other skill check, the PCs are given a chance to "roleplay" between rolls and see if the GM will give them bonus dice for "good roleplay."
I've not found it to be too difficult otherwise in comparison to any other skill check. You just need to have a number of successes in mind and a penalty of one stress for each failure.
Let's say I roll Magic Sight for a random "topic" of discussion: If the PCs have magic sight, then I have them roll 3 times and they need x successes in 3 rounds to make headway (this is very D&D, but works the same for progress trackers..it's just a race to the finish). Each round they fail, they suffer a stress. each round they can also suffer additional stress if they roll poorly (perform stunt). After three rounds, did they get enough successes? If not, they can try again for 3 more rounds.
If they don't have magic sight, then its simply something that either they need to come up with a creative solution, or you as the GM, need to give them something else relevant (intuition for example) and have them go from there with a slight penalty.
Another example: Ride. They are trying to escape from something scary chasing them. Make three checks. For each failure, gain a fatigue (or additional fatigue if double banes). If they realize they'regoing to be too fatigued to fight, they either need to stop and fight before they're exhausted, or come up with a different solution (or roleplaying effort!). Chaos star effect: horse blows a knee.
Another example: Resilience. They're crossing a swamp. 3 checks each day; 1 or 2 fatigue per day. However many days…. Chaos stars indicate encounter, wound or something else (lost items, etc.)
Now back to Charm/guile: 3 checks to get Aschaffenberg (willpower 3..hence 3 rounds of checks in this case)) to hire you for any kind of reasonable reward:
ROUND 1: GM: What would you like to say to Lord Aschaffenberg about why he should hire you? PC: We are here to save the princess, but we need money first. ROLLS.
ROUND 2: Ok, we're serious. We've got these credentials. ROLL
ROund 3: Listen, we can go get another job anywhere and we know your guards would be too easily recognized. ROLL.
Just a long set of examples