Often times in adventures the players can make a skill check during conversation to learn some important information. Does the DM tell the players or otherwise give them a hint that a particular skill can be used?
Or do the players have to guess and try various skills in conversation to see if they come up with anything?
It can be any of the following approaches:
The rules support all but the last of these as viable skill uses.
A lot depends on the GM, but as much on the players. If you're constantly being denied skill uses, ask the GM privately if he's not seeing your hooks for skill challenges, or if he's just not interested in that style of play. It might be either, or neither.
For skill challenges (which is the primary means of using skills in conversation), most of the DMs I've played with have spelled out the associated skills for the check. There are just too many oddball combinations to make the players fish for the one or two correct possibilities.
For social encounters which are not skill challenges:
For passive skills, which relate to what the character sees, hears, or knows, the DM should inform the player about the potential roll (or make it automatically in secret). Examples: knowledge skills, perception.
For active skills, which relate to what the character does, the player should initiate the action. Examples: intimidate, bluff.
There are also a couple of common corner cases:
Some DMs will give players a bonus to their insight roll if the player brings it up, representing the character being more aggressive in their questioning.
Passive skills can often be used actively: Trying to use supporting facts or impressive knowledge to sway an opponent to a point of view.
Depends on the game. By which I mean the players involved in the game. Some players are more proactive than others. Players have good and bad days too. Sometimes they just aren't as engaged in the game.
Anyway, I hold off on asking for rolls. I want the players to have a chance to be proactive about their investigation. I want them to tell me what they're doing, instead of having them wait until I press them for options. Sometimes they'll walk into a situation and start talking and sometimes they'll walk in and ask to roll a die. I have to give them a chance to do what they're going to do before telling them if they should make a skill check or not.
If players aren't taking the initiative to tell me what's going on, then I'll prompt them for it. Ask what kind of social roll they'd like to make or how they're intimidating/questioning/impressing/flirting/etc with someone.
It has been many years, but as a DM I had their up to date skill-sheets available to me and had a digital dice roller behind my screen.
When it was time for a check similar to this I did it in secret to keep them from knowing that there was an opportunity gained/missed. You also do not want them to know if they succeeded on getting information that is true or if they just botched it and were lied to.
Every group I have ever played with has had their own specific feeling about this.
In my experience, the players will generally take a particular approach in their conversation which will make it clear what sort of skill is appropriate. For instance, if they are aggressive or threatening, then it's Intimidate. If they are lying, it's Bluff. Some DMs will ask for rolls up front, but I've also seen situations where players 'fished' for a roll as well. For instance, talking to a mage, a player might try and use Arcana to influence an outcome, which makes sense, but the DM or adventure may not have considered it.
