DMing with Charisma

A sidequest isn’t all that different from any other small-scale plot in terms of lifecycle. Where it mostly differs is in its purpose. In D&D a plot’s job is to form the skeleton of a story, letting the DM and players add musculature, organs, and whatever bits of a body contribute toward this analogy. A good sidequest serves the same role with a few tweaks that make it a sidequest beyond simply being optional. These tweaks put some restrictions on the plots we can use, but they also made a sidequest distinct enough from the main campaign to serve as an effective temporary break.

For this post I’m going to use the 4E DMG adventure breakdown because I think it’s the most direct, concise way of describing an adventure in the same way that 4E is a direct, reasonably concise game to play. Your sidequest may omit some of these parts for various reasons (and going over why and how could be another post).

The first part of any adventure is likely the hook, and a sidequest is no different. You have to give the party a reason to stop what they’re doing and do something else, or to risk themselves on an adventure during what would otherwise be their downtime. Normally a sidequest has a lesser hook because of its scope. While it’s hard to build an entire campaign around “the party gets more money”, creating a small adventure in search of loot is both normal and acceptable. You can also have an NPC ask the players to save a small town, or a single business or a single person, and you don’t need to explain how that translates into a threat against the nation, the plane, or the nature of existence.

A sidequest hook also lets you put the focus on a specific character. Normally a hook has to involve the entirely party so everybody is invested in the story. A sidequest, as an aside to the main plot, doesn’t. You can make the hook about one character’s goals, backstory, friends, or arc and have the rest of the party (willingly or begrudgingly) along for the ride. You could also flip it and make the sidequest about one of your characters, like an NPC the party has already met, as long as the character doesn’t overshadow the party. The point is that sidequest hooks tend to be easier than campaign hooks because you know you don’t have to use them to kickstart a long-running plot, just a side story that the party can explore at their option.

Players must make choices in a sidequest the same way they do in any adventure or session, and those choices must matter, but there’s a wrinkle. In a campaign proper you’re not supposed to present the players with a choice that has a right answer and a wrong answer. You set up a decision, give the players information, let them pick an option (or two, etc.), and let them live with the consequences, but those consequences rarely include “a PC dies” or “the world ends” or anything that would cause the main plot to be a failure.

Sidequests can present plots with wrong answers. If the players answer the riddle incorrectly and blow up the dungeon, they won’t get the artifact sword that prompted the quest in the first place, but the failure doesn’t stall the game. That said, it’s not good practice to do it frequently, and you should prepare for players being frustrated if they put in a lot of effort or spent a lot of resources. It’s better to give them some lesser reward than nothing at all.

The challenges in a sidequest remain the same. You still want to build interesting fights, avoid frustrating mechanics and storylines, use varying encounter types (combat, puzzle, diplomacy, etc.), and keep an eye on how the players react to them all. If you’re using the sidequest to explore a specific character you can build encounters at which they excel (or at which they fail, so they need the party’s help). Here you may want to err on the side of safety with your challenges. Killing a character is rough, but killing a character on a B-plot that doesn’t even affect the large-scale campaign is mortifying.

All plots need excitement, and I would argue a sidequest needs it more than an average session. A sidequest, as a short adventure, goes on a truncated arc. You can’t give the players two boring setup sessions leading to a knock-down drag-out fight because that encompasses almost all of the quest’s runtime. You need to hit the players with something fun enough that they’re happy they went on the sidequest, and if anything it’s easier to do that because you only have to manage the pacing for a session or two.

You could give the players a set piece that doesn’t fit in the normal campaign, like a combat with unusual rules or enemies or a minigame that stretches what a D&D campaign entails. For example, one thing I’ve always wanted to run is a Dynasty Warriors-esque zone-capturing encounter, where the players have to assault enemy keeps to stem the tide of reinforcements while shoring up their own resources. They have to decide whether they want to blaze ahead in a difficult battle, hang back and defend while the allied NPCs do most of the heavy lifting, run around and grab important locations to enhance their battlefield position but leave attack and defense to the NPCs, etc. It’s not easy to organically build a campaign toward a small-scale, but broad within that scale, battle between opposing factions, and the one time I tried to put this into a campaign the players deftly avoided it entirely. It’s something I’ll have a much easier time putting into a one-off session.

Usually the best way to peak this excitement is to do it in the climax, which should be meaningful in terms of the sidequest but not better than similar climaxes in the main plot. The players shouldn’t say the best part of your campaign was the time they fought the orge raiders by jumping back and forth across a stampeding elephant horde if it happened in the session you threw together because you needed to stall another week to design the big bad’s fortress (and if they do, there’s a learning moment about what sort of encounters your players really want). You want a more local finale, one that wraps up the sidequest but doesn’t overshadow the rest of the game.

It may seem like I’m contradicting myself here. I say to give the players an off-the-wall set piece or combat, but not one so off-the-wall they like it more than the main plot. Here’s where having a mutable medium like tabletop gaming comes in handy. If you do give the players an encounter they adore in the sidequest, don’t consider it a lost cause. Instead add a similar encounter to the campaign at a later point, perhaps ramping it up a little. Now that sidequest that threatened to usurp your pacing wasn’t the accidental high point of the campaign, it was foreshadowing. Reward the players for their surprising skill under unusual circumstances, then hit them with the escalation.

If you’re intentionally giving the players filler, you may be tempted to avoid having a meaningful victory. But even in filler, you want the players to know they didn’t just waste their time. Give them an emotional reward rather than a physical or monetary one. Even if they didn’t get any tangible reward they still saved the village, or kept the warlock from opening the devil portal, or prevented Team Rocket from taking over a corner of the Safari Zone. The players know they did good, they’re happy, and they can move on.

With a proper sidequest you could consider the experience and loot to be its own reward. I like also giving the players something interesting enough that they’ll keep it around. Getting a +2 greatsword from the dead orc warlord is neat but forgettable. If the mayor of the town threatened by the warlord grants the party her ancestral sword which has the same game statistics but also leaves a trail of smoke whenever a character swings it, that’s better, and the party will be more likely to work with the sword and less likely to sell it for pocket change later. The rewards for a sidequest can be perfectly in line with main plot encounters of the same difficulty, or even worse, but if they’re fun the players will enjoy them more.

For further reading, TV Tropes has a pretty extensive list of sidequest examples and a few other pages for specific sidequest types. This can give you a good foundation and a lot of ideas what how broad sidequests can be, but there’s no substitute for doing it yourself. As with anything in D&D (or training Amiibos), the best way to learn it to try it and get it wrong.

I’m a busy grown-up with a job and a tie and everything, and so are a lot of the people with whom I game. And one of the problems with being a busy grown-up is that sometimes non-gaming obligations bungle into the way of game time. In the last month, we’ve had to cancel or nearly cancel sessions because we had a player working, being with family, going out of town, saving lives, or storming castles.

That part’s not a joke. All of those things happened.

Gamers are understandably loathe to not game. It’s in our name. But in situations where the game can’t progress because a player or three can’t make it our options are limited. We can either cancel the gaming session or have a session anyway, and then the question becomes how to deal with the missing player. I’ve offered a few suggestions before, but there’s a subset of options I hadn’t considered, namely to run a sidequest.

I’m going to assume you don’t know what that is because my spellcheck sure doesn’t. A sidequest is any quest that isn’t related to the main plot. For example, if you’re on a quest to save a prince kidnapped by a dragon and you have to fight some goblins because they’re guarding the path to the dragon’s cave, that’s not a sidequest because it’s a necessary part of working toward your goal. But if the goblins aren’t a problem you need to handle, it’s a sidequest. Even if killing them helps you because it means you can collect their bounty and afford that dragon-slaying sword to make the final fight easier, it’s still optional.

Which is the beauty of adding sidequests to a campaign. Because they’re optional, you can run them even when you’re short a player so that player doesn’t miss any of the main plot. Sure, the player might be miffed that they didn’t get to fireball some short folk, but they’re still fully caught up on everything that’s going on with the dragon. It’s better to miss a sidequest but still know where you are in the main plot than to miss a session and wonder why you’re hundreds of miles away from where you last remembered, alone, mostly naked, with swords pointed at you.

In general you’ll probably find you need sidequests more in long campaigns. So consider the timing of this post intentional.

There are a few types of sidequests you can use depending on what you need. In increasing order of campaign relevance:

• Filler: A sidequest that has nothing to do with the plot at all. There are no long-term consequences, no rewards, no real threat to the party, and a very low chance that NPCs from the main plot will appear. An example is a video game achievement; you may get points on your profile or what have you, but the game itself doesn’t care whether you have an achievement or not. A filler session exists just to fill time and give everybody something to do, and it’s common to never speak of it against once it ends. In anime circles filler is almost universally reviled. But it can give you a chance to do something totally off-the-wall or non-canon, like try a weird game mechanic or throw a one-shot enemy at the party, and if you really want to game it’s better than nothing.
• Graduated Filler: This is a session that masquerades as filler but gains relevance later in the campaign. For example, if you have a filler enemy who later shows up in the main plot, or if the place you visited in the filler session is the site of the final dungeon, the filler retroactively graduates to the main plot. Again with a video game example, this is an achievement that later unlocks something for you, like unlimited ammunition. From the DM’s perspective this roughly falls into two categories: innocuously important sessions, which look like filler to the players but in which you actually do something meaningful, or ascended filler, where you initially intended the session as filler and changed your mind later.
• Proper Sidequest: A sidequest that affects the campaign but not necessarily the main plot. In video games most sidequests in RPGs are like this; finding all the treasure chests or killing the hidden boss doesn’t meaningfully change the plot but it does give you experience and loot you wouldn’t otherwise have. Arguably most sidequests in D&D are like this for the same reason. It’s a way of rewarding the players who can attend a filler session without significantly punishing the players who don’t. Sure, the present players might be a few hundred gold richer than those who missed a session, but at least everybody’s caught up on the storyline.
• Main Quest in Disguise: A sidequest that’s actually part of the main plot even if it doesn’t look like it at first. Particularly irksome (I clearly have an opinion here) video games use these by offering sidequests but refusing to let you advance unless you complete them because they they provide some necessary reward. It’s a little iffy using these in D&D because you’re defeating the point of having a side session in the first place. There are two ways to go about it. The good way is to have something that looks distinct from the main plot but later ties into it; the goblins seem off the beaten path, but they’re actually the dragon’s minions and they’re guarding one of the artifacts the dragon uses to protect his layer, so now the party knows this and they can look for the rest. The bad way is to keep the sidequest unrelated except for the result; the party gets a magic scroll from the goblins, but it’s not clear why the goblins have it or what the scroll even does until twenty sessions later when it dispel’s the dragon’s wards.

The sidequest types are part of a balancing act, in that the earlier types are better for a player missing a session and worse for a player attending and vice versa. If a player is going to miss a session, they’d generally prefer if that session doesn’t include huge important plot information because they they feel like they’re missing out. But a player who did attend generally doesn’t want to feel the whole session was a waste of time, all risk and effort for no reward. Unless I’m running a breather session I try to stick with the middle two types for whenever somebody is missing and save the last for when everybody is there. This isn’t always feasible, like when a player can’t attend a session mid-dungeon, but it’s a good rule of thumb.

So that’s what a sidequest is and why. Next post I’m going to go over how and a few do’s and don’ts.

In a long campaign players will spend a ridiculous amount of time in your world. If you meet for four hours a week you’ll rack up a solid real-world day of game time every six sessions, and extrapolated over sixty or more sessions it’s pretty startling. Now factor in the amount of time you spend working on each session, and the time you spend on pre-campaign prep, to get a feel for how long you spend on your own world. A long campaign needs to be as fun for you as it is for the players, and in terms of raw exhaustion your bar is much higher.

By the time I get a year or so into a campaign I’m usually spending my time following these principles:

• Mix it up a bit. I sort of feel like I shouldn’t need to say this. Don’t run the same session, or adventure, over and over again. Don’t give the players similar orc patrols to fight even if they are in orc country. Don’t start every plot with “somebody from the party’s backstory needs their help.” Don’t end every plot with “but he was not the villain, and now you have made a powerful enemy!” Your formula will wear on you even more than it wears on the players.

  You don’t need everything to be completely different from everything that came before it, just different enough that the feel changes. Yes, the players are fighting orc patrols, but those patrols can be doing different things, in different situations, with different types of soldiers. NPCs always trigger plots, but some need the party’s help, some are actively working against the players, and some are brand-new and have no particular reason to trust the party. And when you do try something different, like a high-stakes stealth mission in the middle of your otherwise kick-in-the-door campaign, it’s a refreshing change of pace that gives the characters some room to try new tricks.

  This is where you can a lot of utility out of things like Masks and Eureka. You can largely open to a random page and get something that probably isn’t what you were expecting but is close enough to a good idea.

• Invest in your own continuity. Nobody knows the world like the DM (unless the world is based on a world somebody else wrote, like a published campaign setting, in which case “your own continuity” is a somewhat loose definition). The DM loves the world enough that subjecting it to players is a small price to pay for sharing it with them. As such, he or she is the setting’s greatest activist, and there’s no better way to express that than leveraging it in ways your players don’t expect.

  I love continuity porn. (If you print out this post and show it to my mother, please do not omit “continuity”). I love seeing old characters come back a little stronger and wiser, using forgotten items in new ways, answering lingering questions as part of the main narrative, and generally treating the world like a thing that exists rather than a thing that presents short-term stimuli to the players and discards them thereafter. I get excited thinking about how I’m going to pull something from the beginning of the campaign into now and use it to make things more detailed or impressive, and I especially love it when players recognize what I’m doing and get into it. (Wow, after re-reading that paragraph, definitely do not omit “continuity”.)

  That said, you can go too far. Not every person, place, thing, or action needs to be significant. If the passing wheel merchant was actually the criminal overlord all along and the only clue was that they both said “Hey, how are ya?” in greeting, you’re probably not adding to the players’ experience or yours as much as you think you are. Save it for the things that really deserve it, foreshadow them when you can, and watch as your loose association of nouns becomes a story worth telling.

  When you do bring up something old or subtle enough there’s a good chance your players won’t recognize it. That’s fine. Remember, you may have turned the grand duke’s nephew’s subplot over and over in your head for weeks, but the players only heard one offhand reference to him during dinner, and even then half the party wasn’t present. You generally can’t expect they’ll have the same knowledge of your world as you do and occasionally they’ll even surprise you by remembering something you forgot. It’s your call whether to remind them, let them roll to remember (a straight Int check works, but account for the fact that there are few skills for simple memory), or bask in their ignorance and only later recount your foreshadowing during the big reveal. Just don’t rely too much on that last one.

• Use characters and monsters you like running. When you’re going to have a monster-of-the week villain or a one-and-done NPC, you can make them anything that fits your needs. But when you’re talking about a campaign villain or a long-term ally, it’s important they they’re as fun for you as they are for the players, preferably top to bottom. Give the character a class you like playing, so when they get involved you enjoy using their powers and abilities. Give them an accent or a verbal idiosyncrasy (extraneous pluralization, overuse of the phrase “I know, right?”, refers to everybody by occupation rather than name, etc.) so you and the players know when the character is speaking. Find ways to get them involved (though not too much, of course) so they become a regular part of the campaign.

  This extends to any iconic fights. When you’re having fun with a monster it will show, so design monsters you like playing. Give them abilities that stop or cancel the player abilities you can’t stand and play up things you want to see more. Use the environment, the storyline, and the players’ personalities in interesting ways. Not every fight needs to be a custom-built, off-the-wall, everything-means-something encounter, but when you’re at the end of an arc or in an important location or just need a pick-me-up there’s not much better at that than a fight that gets everybody involved in a fun and interesting way.

  If you’re using something out of the box, make sure it’s not something you hate. One of the problems and benefits of long-running campaigns is that you tend to see the same monsters, allies, and bad guys over and over again, because that’s what the campaign is about. So if you don’t like running spellcasters, maybe the devil lord shouldn’t have a cadre of liches. But if you do like minotaurs, put them in a prominent place so they come up often. Use different types, like a barbarian here or an aristocrat there. Explore their society. Break out those minis you’ve always wanted to use but could never justify. Take advantage of the fact that your campaign has themes and make them something you want to use.

• Have good players. This one’s a bit of a cheat, because it’s not an ongoing design choice you make regularly over the course of a long campaign, but it’s still the most important point on this list. If you’re going to be running a game for the same group for a year or two, don’t invite people to merely tolerate. Invite people you like. You’re all ideally going to be stuck together for the life of the campaign, and you don’t want to get three months in and realize you have to scrap a bunch of your long-term plans and character arcs because you can’t be in the same room as one of your players (or two players can’t be in the same room as each other, etc.)

  The thing about having good players is that if you ask their opinion they’ll give it to you. Tabletop gaming is a back-and-forth hobby, and good DMing involves getting feedback from players on what’s working, what’s not, and what they want to see going forward. The nice thing about this in a long campaign is that different people find different things interesting in different amounts. Even if you’re loving your minotaur city, the players may not be, and that forces you to try something new. You’re gaining and losing interest with the speed of four or five or six people rather than one, and that can help you break out of a rut you didn’t even know you were in.

Again, this is all good advice for a short campaign too. But it’s doubly important when you’re going to be in the same world running the same general plot for a while, especially if you’re like me and you need occasional breaks from a given activity to keep your mind going strong.