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 "It's just a talk encounter. Send the bard to make nice."
If that's the attitude of your gaming group, you may not be designing your roleplaying encounters correctly. What they should be saying is "Oh no, it's a talk encounter. Buff the bard with eagle's splendor, quick!"
Wait, did I say "design your roleplaying encounters"? Sure I did. Just because some encounters don't need stat blocks doesn't mean that they don't need preparation and careful design. If anything, roleplaying encounters are more demanding, because you have to allow for more options than just combat. Preparing a satisfying roleplaying encounter requires some deeper thought about how your players respond to pressure, flattery, and so forth.
The need for careful design is especially pressing for what I call switch encounters, that is, encounters that begin as roleplaying but that could easily become combat encounters. A devil, for example, could want to chat with the party before destroying them; if it learns that they are both seeking to bring down a group of diabolists serving a Demon Lord, the devil might even leave the party alone, since both groups seek the same goal.
For each roleplaying encounter, you need to prepare three things ahead of time: what the PCs can gain from the encounter, what the NPC might accept in exchange, and what skills or class abilities will help them in the encounter.
What the Party Gains
Combat encounters are easy; kill the monster, take its stuff. Roleplaying encounters are tougher; PCs still gain XP for defeating them, but it's also possible that the party will be defeated and not even know it. While the goal of the encounter should be clear to the DM at all times, the PCs may not know at the start whether they are dealing with a passage encounter, a resource encounter, an information encounter, a talk-or-fight encounter, or something else.
Passage: The party gains entrance to a hidden or locked location, learns of an important site, or gains a pass, key, or password that gets them through a gate or into a secret chamber. The whole encounter is, essentially, an unlocking of an area that they can't reach without completing the interaction successfully.
Information: The party gains a useful clue, learns a weakness to exploit in a future encounter, gains access to spells or books that contain crucial information about the plot or the major villains.
Resources: Some good or neutral-aligned characters will offer the party treasure, healing, mounts, magic, or other resources if they believe that the party will serve a cause they both believe in. This could be a magic sword with a bane enchantment against a major monster type, it could be a set of healing potions, or it could be ancient coins to bribe an undead king into serving the party as a distraction while the party slips over the castle walls. In most adventures, there are at least some potentially friendly encounters that offer these sorts of treasures.
Avoiding Combat: Some roleplaying encounters just offer the opportunity to avoid spending precious spells, hit points, and other resources on a tough fight. In these cases, it's always best to signal very clearly that the monster in question can crush the party without a second thought. Alternately, the talking at the beginning of an encounter gives a villain's minions time to surround the party or bring up reinforcements, so that the stakes get higher and higher the longer the party talks -- ratcheting up the tension on the party spokesperson. If the parley collapses into combat, the villain will be in a stronger position than he was at the start. These are the "switch encounters" discussed in more detail below.
Those four categories cover most roleplaying encounters.
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Roleplaying Encounter?
One of the strange terms in the D&D game community is "roleplaying encounter," which generally means some kind of talking encounter. However, D&D is a roleplaying game. The Player's Handbook says so in the first sentence: "This is the Dungeons & Dragons Roleplaying Game, the game that defines the genre and has set the standard for fantasy roleplaying for more than 30 years." So aren't all encounters roleplaying encounters in a roleplaying game?
Yes, they are.
The word "roleplaying" means "an instance or situation in which one deliberately acts out or assumes a particular character or role" (from www.dictionary.com). When creating and playing a character in D&D, you are always roleplaying because the character is not you.
However, over the years there has grown a mentality in the community of people who play roleplaying games that a "roleplaying" encounter is a talking encounter whereas a combat encounter is a fight. In truth, a "roleplaying" encounter should be called a negotiation encounter or a talking encounter. But, since the majority of the community understands roleplaying to mean talking (as opposed to all the other ways you roleplay your character), this article uses the term "roleplaying encounter" to mean a talking encounter of some kind. Just remember that there are more ways to roleplay a character than merely through talking.
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Lies and Treachery
It is ridiculously easy to lead roleplayers astray, as many players don't seem to realize that NPCs might be lying to them. Villains, double agents, and slippery underworld characters might all have perfectly good (or perfectly dastardly) reasons for not telling the truth. For instance, in a talk-or-fight encounter, the villain might be talking only because he needs to stall for time as his slow-moving undead minions arrive on the scene, or while his lancers or crossbowmen move under cover to a flanking position or the like.
In other cases, an NPC might seem to be helpful, but really is pumping the party for information. Are they planning on raiding the necromancer's stronghold? When? Do they know about the secret tunnel? Once the informant has told the party about the secret tunnel, of course, he might go to the necromancer and tell him that a raid is coming, thus selling out both sides -- and making that tunnel encounter much tougher, if the necromancer puts extra defenders there.
What can a suspicious party do? Well, there are defenses such as Sense Motive skill checks and the use of a detect lie spell. The first of these is probably more helpful than the second.
What the Monsters Gain
The creatures or characters that the party is speaking with also have their goals in a role-playing encounter. They might want food, souls, gold or other monetary bribes, flattery, a completed quest, or information of their own. If the monsters don't gain what they want, the encounter ends in failure for the party. This might mean they hear "I can't help you" from the scholar they consult, or it might mean that the giant considers them too weak to bargain with and decides to eat them all instead.
For the most part, I design roleplaying encounters to have three stages: discovering what the monster wants, actual roleplaying between DM and players, and a skill check-driven resolution, either positive or negative. If the role-playing resolution is negative, the result is often combat.
Discovering what the monsters want is usually the easy part; if a PC asks, most monsters will answer. Of course, most monsters will ask for more than the minimum. Whether the party can haggle successfully depends on their style and skills.
Using Skills and Class Abilities for Roleplaying
 The skill-based classes and certain prestige classes have abilities such as Bardic Knowledge, Artificer knowledge, Diplomacy, Intimidate, Bluff and the like, all of which can be useful in a roleplaying encounter. But how far should they go in replacing actual conversation between a player and DM?
This depends on what your players enjoy. If a player has sunk skill ranks into these abilities, they should get use out of them. Likewise, characters who have sunk those ranks into something else shouldn't get to talk their way out of trouble if they lack the abilities.
I like a two-pronged approach. First, every roleplaying encounter must include the NPC's Initial Attitude (Player's Handbook page 72). This determines how tough it is for the PCs to talk their way out at all -- and reminds you whether the encounter can be defeated through non-combat means. If the party lacks the skills to sweet-talk an Unfriendly or Hostile monster, then tough luck. They should fight it out, burning hit points, spells, and other resources in the process.
Second, if one or more of the PCs do have the Diplomacy skill or Charisma checks to change a Hostile or Unfriendly monster to have a Neutral or better attitude, talk it out as long as you like, playing up the weasely informer, the moustache-twirling villain or the drooling monster. Have fun with the conversation, but the, at the crucial moment, when the informer says, "Well, I shouldn't tell you this...," ask the player doing most of the talking to make the Bluff, Diplomacy, Gather Information, or Intimidate check, as appropriate.
Set the bar for your role-playing skill checks ahead of time and stick with them. The rough rule of thumb is that the DC should be roughly equal to 12 plus the party's level, so that a skill-based character with maxed-out ranks and an ability bonus expects to succeed 75% of the time -- and a character without skill ranks and no ability bonus succeeds less than 50% of the time.
Other Options
What if the party doesn't contain any high-skill characters, or they flub a crucial roll? There are a few other options. Some monsters will take bribes or payoffs. Others can be avoided through magic or disguises. If there are any items, quests, or information an NPC needs, they may just demand those instead. The party is not necessarily defeated just because a social skill fails.
Switch Encounters: Roleplaying into Combat
One of the best ways to make a combat more entertaining is to set it up as a roleplaying encounter first. The knight who brags he can spit the party members like piglets on his lance, the giant who toys with his food, or the evil wizard who pretends to be their friend before betraying them one night during the midnight watch are all potentially more interesting than merely rolling dice. If the party is going to meet one of these, prepare some dialogue ahead of time -- and set the initial attitude to Hostile.
The trick to a switch encounter is simple: though he is hostile, the major NPC doesn't attack right away. Sure, he hates the party and wishes them ill, but he wants to toy with them first. The encounter looks like a roleplaying opportunity for the party, and it is. Any PC who wants to bandy words, propose single combat, insult their opponent's tribe and family, and so forth has time to do it. The NPC, though, will wait until he's good and ready before attacking -- and will use the time to try to arrange things in his or her favor by summoning henchmen, alerting the (evil or corrupt) town guards, arranging for an invisible assassin as backup, gaining the divine favor of evil priests, and so forth.
One easy way to stretch out the roleplaying opportunity here is to separate the sides. The NPC may do his taunting from a half-hidden position: top of a tower, the other side of a moat while the drawbridge slowly lowers, and or something like that. One member of the party must "keep him talking" while the others make their own preparations.
When the party finally attacks, the major NPC has a readied spell or action (since he's been expecting this) and he may have hidden assets as well, just as the party does. If the NPC has high ranks in Bluff or Perform (Acting), he may have completely fooled the heroes (invited them in to a meal while poisoning their wine). In cases like this, DO NOT ask for saving throws or Spot checks from the party. Instead, ask for Diplomacy and Sense Motive rolls. Determine the required DCs for these as part of the encounter prep. Asking for a Spot check is a big red flag to players that something is going on, and many "break character" and begin prepping for combat when their characters (who failed the Spot checks) would not do so.
Instead, wait and drag the party further into the villain's clutches. Until someone says "He's playing us", let the NPC get away with it. That way, the sense of betrayal is much more real -- because you, as the DM, have fooled the players to some degree as well. Once the players catch on, THEN ask for the Fortitude saves for the poisoned wine, the Spot rolls to see the hidden archers, the Spellcraft check to notice the necromantic spell on the servants, and so forth.
Conclusion
Roleplaying encounters require design and prep work to have maximum impact, and usually the ones that work really well are remembered much longer than most combats.
About the Author
Wolfgang Baur is the author of dozens of adventures, from the "Kingdom of the Ghouls" and "Gathering of Winds" in Dungeon magazine to upcoming releases from Wizards of the Coast. He offers custom-tailored adventures and professional advice to patrons of the Open Design blog.
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