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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?

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It can be any of the following approaches:

  • The GM describes the skills needed, and the players play them as they roll them.
  • The GM has a set of needed skill rolls in mind, and as the players interact appropriately, allows rolling them to accomplish the skill challenge
  • The GM has more skills than are needed for a skill challenge, and fills in the skill challenge and effects based upon what the players roleplay, calling for skills at various points
  • the players may request a suitable skill challenge, if the GM agrees, and if they play it properly, he lets them make the rolls
  • the players roleplay out the scene, then the GM creates the skill list for a skill challenge, or a single skill, to accomplish what the roleplay attempted.
  • The players can state their intent, and the GM can call for rolls or a skill challenge as desired, sans roleplay.
  • The players can state their intent, and the GM can call for rolls or a skill challenge as desired, modifying by their roleplay.
  • the players can roleplay it out freeform, and the GM simply decide if their skill is sufficient, when coupled to the roleplay, to achieve some desired efect.

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.

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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 every played with has had their own specific feeling about this.

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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 Initimidate. 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/adventure may not have considered it.

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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.

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Re your third point, I think that is bad practice. It rewards smart players at the expense of smart characters. Put another way, a smart player and a stupid player both playing the same smart/skillful/whatever character should get the same information from a conversation. –  Sparr Dec 16 '10 at 6:23
    
@Sparr -- Meaning the insight paragraph? This can be balanced out by having NPCs react negatively to being given the third degree. The bonus is usually used to represent the difference between simply listening and observing, and actively interrogating a subject looking for lies. Still... You're right, and not everyone likes giving a bonus for that sort of skill use. –  AceCalhoon Dec 16 '10 at 14:12
    
@Sparr - how do you not reward smart players? At the end of the day, a smart(er) player will work the system better than a non-smart player. –  YogoZuno Dec 16 '10 at 20:56
    
@YogoZuno Simply rolling skill checks in secret during dialogue will avoid rewarding smarter players in this particular scenario. –  Sparr Dec 16 '10 at 22:44
    
Skill challenges aren't actually the primary use of skills in conversation (although that might be how you are using them). Skill challenges are just a way to assign an XP award to a complex scene involving more than one skill check. Skill checks are just skill checks. –  Peter Seckler Dec 17 '10 at 13:41
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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.

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