This thread specifically addresses Persuasions, Intimidation and Deception skill checks but also holds true for some other skill checks during dialogue. I very much like the game but i feel that these are a bit of a mechanical weakpoint.
I will start with how dialogue skill checks SHOULD work. This includes ideas on how to improve on how they currently work. I will point out the problems they currently have in the section after that.
In roleplaying games dialogue skill checks let you convince a person of a "concept" or statement. However the repercussions of convincing an NPC of a made up concept/statement can have all kinds of results. You could use deception to convince a guard that you are a criminal even if youre not and get jailed. If you dont know much about the NPCs believes or values convincing them of something can at times backfire in spectacular fashion. The chosen concept/statement that is used for the skill check holds more importance than the skill check itself.
The more Information you acquire the easier it would be for your character to find concepts/statements that allow you to nudge an NPC in a favourable direction via dialogue checks. In terms of PC gameplay, this could mean reading a book that tells you about said NPCs backstory or coming across a variety of Information through various means when exploring the world that would be a requirement to unlock certain skill checks.
Unfortunately as (dialogue) skill checks are currently implemented, they feel like nothing more than cheap cheatcodes. No matter what situation youre in, making the dialogue skill check always leads to the most favourable outcome even in times when i felt that the logic behind the statements that were made was pretty poor. It just feels bland to automatically choose the dialogue check for the best possible outcome without evaluating wether or not the statements make any sense. There are also almost no situations where prior knowledge is required to unlock a dialogue check. The pinnacle of this are "double" skill checks like rolling insight against yurgir to unlock one particularly powerful dialogue check or double deception checks against one of the tiefling kids so he gives you the key.
This is not interesting gameplay. Victory from skill checks feels cheap and unrewarding and no amount of thought or decisionmaking is required. Overall this feels like a large deviation from how they work in tabletop and as a gameplay element they are simply disappointing due to the lack of thought you put into choosing them (as they always lead to the most optimal outcome when available).
id also like to point out how different the design philosophy for skill checks is when compared with a similair feature - the background/class/race unique interactions. When you pick a Barbarian to interact with a guy lying under a heavy object and you get the option to use your class prompt to remove the object it feels good because you as a player made the correct choice of barbarian for this specific task. When you get interactions based on "shar priest" because you picked shadowheart when interacting with objects related to shar it feels good because you as a player made the character choice that unlocked more options. These heritage checks are also much rarer for any give heritage when compared to the omnipresence of dialogue skill checks and as such feel more rewarding when you do get them.
I really hope this can be taken into consideration in the future.
Cheers