No flips for you!
As an added example of a failure, one of my players wanted their character to get in good with one of Sigil's factions. However, his previous associations meant this would be a challenge. He first attempted to gain an audience and failed his DC 15 CHA check (the DC was set because the faction was unfriendly and his approach was a pretty straightforward ask). This meant he was told that the prelate was busy at the moment, but that the PC was welcome to wait to see if a there was a time to work him in. I also told the PC that he was certain that this was a brushoff and that there wouldn't be any openings for him (a no-check Insight on the clerk). The player elected to call the bluff, and spent a his week of downtime to wait in the waiting room every day during business hours. I determined that this expenditure of resource was sufficient to overcome the challenge of getting a sit-down without another check, so, towards the end of the week, the PC got his meeting. Of course, nothing had changed, so the starting DC was still 15. The player made a reasoned argument that his association with the other faction was only due to being hired for a job, which he prides himself in always completing contracts, and offered his considerably useful services to the this faction in exchange for certain privileges. The factor was interested in this as the PC did have useful skills, and the explanation was enough, I felt, to lower the DC a bit, so I called for a CHA DC 12 check. The player bombed it (around an 8, I recall). As a consequence, I had the factor offer a very tough "interview" job with a 'do it or don't come back' statement and almost no informational assistance to accomplish the task. This wasn't what the player wanted (he wanted access for his character to certain resources, and not to have to involve the rest of the party in this) as he know had to ask other party members for help in accomplishing this goal. They agreed, but that led to another failure where the whole party was defeated and left for dead (they got better, for a given sense of the word). Now, that situation stands with the target of the task completely in the wind and unreachable without much hard work and the faction quest failed with no access whatsoever and any goodwill remaining gone. The player hasn't yet engaged back with this as another party member's needs are currently driving the group, but we'll be back to this in another session or two. I believe the PCs are discussing a rather daring plan to try to lure the target back to Sigil for a pit-fighitng betting opportunity and then grab him at the match -- which one of the PCs will be fighting in! Sounds like a great opportunity for some more rolls to go horribly wrong for them and maybe land the whole party on the wrong side of the Hardheads (Sigil's self-appointed police force)!That's so true. Last night, my Eberron session kicked off with an important social interaction challenge that was pivotal to their success on the overall adventure. They needed to team up with NPCs who were hostile toward them without letting them know their true motives for helping (which would undermine a kingdom's plot to overthrow the government of another nation). I prepared the central NPC's ideal, bond, flaw, and agenda, and fleshed out the personality traits of the other four NPCs. I then presented a series of objections to what the players were putting forward. Overcoming those objections would slowly improve the NPCs' attitudes. Once the "final attitude" was resolved, then came the ask - could they work together?
They overcame some objections handily, gaining automatic success. But some weren't so clear cut and I called for rolls. Every single one was filled with tension as the mostly un-charismatic PCs considered what arguments to make and what limited resources to apply to improve their odds. You'd think they were trying to avoid disintegration traps.
In the end, they succeeded in convincing the NPCs to team up. It was as tense and interesting as any combat. And being an alliance built upon a lie, we'll see how this goes awry soon, I'm sure!