Over the DM's Shoulder

Showing posts with label tabletop gaming. Show all posts
Showing posts with label tabletop gaming. Show all posts

Monday, July 13, 2026

How to Plan a Quest

After nearly 300 articles, I've realized that I've never given a full article to developing quests. I've written plenty about entire campaigns, including ideas you can use and methods to create campaigns based on player suggestions, and I've written about methods for planning moments in-game, but we've never delved into quests in particular. Campaigns are overarching and ideally include several connected quests--it's those quests that get us from point A to point B that have gone ignored. Well, it's time to rectify that; here's how to plan a quest, the most basic step for any GM. 

First off, what exactly is a quest? Quests are goals for the player characters that require some kind of effort to complete. Generally, quests have beginnings (the introduction of the quest where the players are given the opportunity or burden of doing something), middles (some manner of action or decision-making that eventually completes the quest), and endings (a resolution in which the players are given a fitting outcome for their effort--this is usually but not always a reward of some type). At its most basic level, the quest is what makes a tabletop game a tabletop game. When we play TTRPGs, we spend most of our time and energy working on quests (including personal quests). 

What makes a fun quest, or a memorable one, or a quest we'll want to tell people about? As always, this differs from person to person, but as a general rule, good quests keep the players in mind. As GMs, we want our quests to have beginnings that catch the interest of our players; we want middles that are engaging and exciting; we want endings that resolve the story of the quest and give the player characters what they deserve. Let's go through the steps of planning a quest with the players in mind. 

A quest can be developed from any point in the equation--you can start with a beginning or an ending or a middle or even just a loose idea. Personally, I tend to operate best starting with a loose idea and filling in the details from there, so my examples in this guide will follow that pattern, but know that you can start wherever you're inspired to start from. For the sake of this guide, we'll use as an example this loose idea: the player characters need to transport a religious figure from one city to another safely despite dangerous roads and threats against the religious figure. 

Since the idea already gives us a good idea of what the middle of the quest will be, let's start there. It's helpful to think about all the things that the player characters need to do in order to complete the quest. They'll need to get contracted in the first place, make contact with the religious figure, leave the settlement they're in, safely travel to the destination settlement (with lots of opportunities for ambushes, wild animal attacks, conversations with the religious figure and their entourage, and other excitement), and get the religious figure to where they want to go. 

We can then further choose details to fill in this outline: the head of the religious figure's church personally requested that this quest be carried out in order to spread the religious figure's specific style of wisdom; the religious figure's teachings are divisive and have kept other adventuring parties from agreeing to do the quest; the religious figure is treating a lackey poorly when the party arrives to meet them; the party receives judgmental looks from the townsfolk as they leave the settlement; there is an ambush by religious extremists on the road; the religious figure continues to treat their associates poorly as the journey continues; and some of the religious figure's entourage deserts once they arrive at the destination settlement. These details add complications and colorful elements to a basic outline that will increase the players' enjoyment of the quest as they play it. That's the main goal during the middle of a quest: giving the story ups and downs and details so that it's memorable and interesting.

We started with the loose idea of moving a religious figure from one city to another, and in two simple steps, we already have a fairly solid questline. You may be saying to yourself, "That sounds like pretty much everything. If the middle covers so much, why break the introduction and resolution into two more parts?" This is a good point, and the answer is that introductions and resolutions are especially delicate to handle. Let's get into those and how to handle these more intricate elements of quests. 

The beginning of a quest is delicate because you need to pique the interest of the player characters and the players so that they agree to take on the quest in the first place. This is a tabletop game, after all--you could be doing literally anything, so signing on to a quest means ignoring everything else, and that might take some convincing. There are a few tactics which are tried and true in this regard. A noteworthy payment often gets interest high, though I would argue that a big reward can ring a bit hollow on its own. You might offer advancement in a larger questline if you have one to work with, or try to come up with something that directly appeals to a player or player character (perhaps something related to a player's individual interests, or information on a lost loved one or a lead on a missing heirloom for a player character). You can also make the apparent difficulty of the quest a factor--a big payment for a seemingly easy job is a draw from players and player characters, while a small payment for a seemingly difficult job would give many players and player characters pause. Finding the hook that fits your quest best takes some thought. 

In the example of transporting the religious figure, I would opt for a combination of hook factors. For starters, it's going to be clear from the start that this religious figure is divisive if not outright unpleasant, and that means that some narrative weight will be bringing the players dramatic tension. To make up for that, I would offer a fairly sizable reward for completing the quest. To that end, I would promise a fair amount of funds as well as some manner of magical item. At the same time, I always try to keep individual players in mind as I GM, and I know that my usual group of players would all enjoy a chance to engage with religious hypocrites, so the nastiness of the religious figure can be turned into a positive rather than a negative. Obviously, this wouldn't work for every party, but I'll also say that I came up with the loose outline for this example quest based on what my usual players would enjoy. That said, we now have the promise of payment down. If we add some other details--the higher-up religious leader seeming to want to be temporarily rid of the religious figure the party is transporting, a promise that the destination settlement actually wants the religious figure there, and an assurance that the roads are clear and safe (making it an easier job, even though that won't really be true)--then we've got a pretty clear picture of how to start this quest. 

With the beginning planned, the ending is generally shaped already. We know what the quest's reward is supposed to be, and we know what happens when the religious figure arrives at the destination settlement--many of the religious figure's people desert, and the temple in the destination city pays in gold and a magic item. But this is not a very satisfying ending, and that's where the delicate nature of resolutions come in; in fact, this is why I say "resolution" rather than "ending." We need to give the players and player characters some kind of closure on this quest, and treasure is never closure. To give real closure, we'll need to factor in details that come up during the quest--how the player characters interact with the religious figure and what the players want the outcome of it all to be. But those elements of closure will need to be improvised when the time comes; we can't be sure of what will happen until it happens. However, we can make some educated guesses and plan accordingly. 

In the example of the religious figure, the ending will really hinge on the world surrounding the religious figure. The players will want to know what happens to the religious figure and with the people around them. As I noted above, the religious figure will be characterized as fairly unpleasant, and players love to see "bad" people get some kind of comeuppance, so we'll want to have some kind of downfall moment for the religious figure. Perhaps they learn that their leader (who paid to send them to the destination settlement) secretly disdains them, which would crush their spirit. A similar outcome might result from being abandoned by some or all of their entourage on arrival at the destination city. We might even employ a crafty move as the GM and have these crushing moments lead the religious figure to ask the party for validation, giving the player characters the opportunity to voice their disapproval. But the point is not just to punish the religious figure; we also want to suggest that they have a reckoning moment because of it. Maybe the religious figure becomes humble and starts their religious study over anew, and maybe they only have the seeds of doubt in themselves planted (this is an especially good option in a larger campaign where the religious figure can reappear later with real change). But in either case, the party has had some role in creating change in the direction they think is best, and that is more closure than treasure will ever be. 

Planning a quest is easy. Planning a quest that reaches your players on a fundamental level is a lot harder. That's why I stress the importance of trying to create quests with the players and player characters in mind. Once you're comfortable doing so, you can start to plan differently. I like to plan quests broadly with only minimal details (like you find in the guide above) and fill in new details as the party reaches that point in the story. This allows me to use momentum and callbacks from previous quests to enrich planned but unlaunched quests. A perfect example arose during my most recent campaign:

In my Of Gods and Dragons campaign, I took three experienced D&D players, gave them level 12 characters, and threw them into conflict with a mass of dragons and deities with no real indication of what the campaign as a whole was meant to look like; they only knew that they were to speak with Boccob, chief deity, and resolve a problem that affected all of existence. (I mention that these were advanced players because this kind of campaign premise would be a chaotic mess for beginner or even intermediate roleplayers--I was careful in administering such an ambitious idea.) Pretty quickly, the party aligned themselves with the charismatic outsider silver dragon, whose main argument was that balance should be restored because free will was impaired without it. The party decided that there was power in numbers, and they set about gathering the metallic dragons to create an alliance to restore free will, which of course proved more complicated than originally planned. 

How does this align with how I plan quests? Well, I wanted a freeform campaign with the feeling of a sandbox. I didn't determine that there was a proper order for anything, and any given god or dragon could hypothetically have been ignored, and the party still could have resolved the problem with Boccob. What I did instead was come up with a loose quest for each dragon and deity based on their personality and situation, and completing that quest would mean having that figure as an ally in the overall campaign. 

As it played out, speaking to each of the metallic dragons fell into a sort of pattern. Each of the metallic dragons had some problem that kept them divided and therefore weaker--the gold dragon was very polarized in thinking and had a hard time working together, the bronze dragon was too wrapped up in ordinary life to pay attention to larger affairs, the copper dragon had only had powers for a few days and was reeling from the sudden life change, and the silver dragon was so focused on being an outsider that she was afraid to even try working with the others. This basically meant that the party had to play therapist to the metallic dragons, trying to coax cooperation out of wildly powerful beings who were mired in their own affairs. So when the party finally got to the brass dragon, they were expecting another therapy session. 

To be honest, another therapy session was what I had planned. The brass dragon was debilitated by a depression that had lasted centuries. I thought it would be interesting to have the player characters figure out what was depressing her and help her to climb out of that pit. But as the session drew near, I started to realized that the quests were starting to feel very similar and that a depressive episode that lasted for hundreds of years (on an exceptionally resilient person, too) didn't make sense in the way that the other metallic dragons' isolations made sense. I did what made sense: I called an audible. 

I kept the basics the same. The brass dragon had been depressed for more than two centuries. The reason for it was losing her husband, who did not share her immortality as a dragon. But there was no amount of talking her through her grief that would help. To make that work, I decided that something else was at play--a curse. None other than the blue dragon, a devilish charmer with sadistic tendencies, had placed the curse on the brass dragon as the initial depression had been setting in centuries ago, and it had gone unnoticed for all that time. I had the brass dragon throw out a few suspicious remarks about a strange man clad in a blue suit who had appeared all that time ago, which set the party to investigating, and soon, they were on the trail of lifting the curse and setting the brass dragon back to her proper self. This change spiced up the campaign, kept the feel of the quests consistent while adding something new, and reminded the players that it wasn't all just therapy--there were chromatic dragons out there plotting the downfall of everything the party and their allies held dear. That is to say, I got to keep my loose quest idea, adjust some details to better serve that moment in the campaign, and gain some forward momentum at a critical time. To accomplish this, I kept my quest formula (meet the dragon, figure out what they need to overcome, and help them, gaining resolution and an ally), making small changes to increase detail and engagement in the process.

The quest is perhaps the most basic unit of a tabletop game. Someone requests help, the party helps, and there's resolution. A campaign is not a quest--it's several or even many quests put together. I think that for a long time, I had lost sight of quests in favor of campaigns; that's probably why there are so many campaign-related resources on this site, and I'm only now after a decade writing about quests. But quests are vital. A house built of broken lumber is hardly a house, and a campaign made of uninspiring and tedious quests is a poor excuse for a campaign. So when you plan for your games, try to keep the basics in mind: plan broadly at first, consider details that will appeal to the party and the players, and aim for resolution beyond treasure. From there, you can start to expand your skills to add twists and turns in the story that even you could not have seen coming when the quests and campaign were just ideas. But always remember that quests should be fun--that is, after all, the point of gaming.

That's all for now. Coming soon: a pirate D&D one-shot, how to modify D&D for a western setting, and a detective D&D one-shot. Until next time, happy gaming!


Thursday, November 6, 2025

How to Not Get Weighed Down by Worldbuilding

Worldbuilding is fun, valuable, and rewarding. Plain and simple, time we spend worldbuilding is time we spend enriching our worlds and making them more real for our players. However, like most all things, this is a spectrum. There are diminishing returns to worldbuilding. To avoid the pitfalls of pushing worldbuilding too much, let's explore the ways it can let us down. 

Let's think about this logically. Worldbuilding is a spectrum with a shapeless void on one end and a perfectly detailed world on the other. Obviously, we want something closer to the detailed world. But do we want the most perfectly detailed world possible? Practically speaking, it would take years of intensive work to come anywhere close to that, and there does come a point where knowing each NPC's favorite food lacks much of a point. So where is the line? How do we get the perfect balance of worldbuilding to narrative freedom so that we're neither too rigid nor too flexible? 

I've done a lot of worldbuilding. As of the writing of this article, there are 59 articles on homebrew setting details from big picture (homebrew rules for magic, gods, and dragons) to very small details (pet culture, home décor, and tattoo art). Were all of these necessary? Absolutely not. I did not need to, for instance, design city flags for all of the major cities in my homebrew setting. These have yet to enter or enrich gameplay, and so they were just an academic experiment, a creative act meant to connect with my world. And that's really the trick--worldbuilding is a way to connect to the world and better understand it, not something that's meant to define the players' experience. 

A while back, I played in a campaign that I overall enjoyed. There was this one thing that got in the way of full enjoyment, though, and that was that I always felt like we were on a tour (often guided) of my GM's worldbuilding. His favorite characters, NPCs he'd written stories about for years, were additional party members or vital allies and foes. Our adventures took us across the land, checking out all manner of homebrew locations. It was all very memorable, but I didn't feel like our party was the star of the show. I felt like we were witnesses to a story being told by forces bigger than us. It was not what I would describe as completely fulfilling. 

I think that GM let worldbuilding get in the way. I think he spent, as I did, dozens of hours worldbuilding and creating characters and preparing stories, and he got swept up and forgot that we--the party--were supposed to decide the story, that we were the stars of the show. In reality, his NPCs should have been interesting supporting characters. His locations should have been scenes for us to define. But everything was already written when we got there, so it was hard to feel empowered as characters. 

The thing is, this is a good GM. His characters, player character and NPC, are interesting and real. His settings are classic fantasy with a brutal twist that's always fun. His storylines put complex questions of good and evil at the feet of the players. It's just this one thing that got in the way for me, and I think the mindset that gripped my GM is a common thing. 

The truth is, our job as GMs is not to paint a perfect picture. We could, if we really wanted to, spend five minutes lovingly describing a stretch of hallway every time a party passes through one. We could paint a novel-style portrait of the merchant who will never be interacted with again. These obviously don't help us, though, and they don't help the player. 

I have a simple rule: if a bit of worldbuilding naturally comes up, I'll go into it. I've written about burial methods before, and when someone was to be buried in one of the epilogues of my most recent campaign, I referred to that information and had the burial proceed appropriately. In the same campaign, the player characters hopped across different cities and cultures, and I was able to describe changing geography and architecture styles. In epilogues of a recent campaign, each player bought street food in the city they'd chosen as their home base, and I could give them distinctive experiences. 

But the thing is, I didn't provide burial methods information at every turn. The geography and architecture of each location was provided as it was relevant (in small bursts as the location is explored), not in one long, nonstop lecture about the appearance of a city. I explained what street food was available when players sought out lunch while exploring their cities, not the second the entered the city. I offered worldbuilding details as necessary, and never more. The star of the show is my players, not my worldbuilding. 

And it's not like I'm not proud of my worldbuilding! My guides to clan groups and other organizations revolutionized how I think about my homebrew groups. My guide to clothing forever changed how I imagine my world looking. My guide to parenting style informed how individual people think about family, about authority, and about themselves. My guide to the solar system looked beyond Evanoch and even Izar, the planet it is on, to situation all of this in a larger context. My guide to lasting feelings about a continent-wide war fought over freedom of magic use is full of interesting and useful information that also invites new stories being told. But I cannot start out a campaign by having an NPC run up to the party and shout, "There's some interesting organizations to look into, and clothing styles can tell you a lot about a person, and everybody raises their kids differently here, and the solar system is vast and plentiful, and there was a recent war that people are still pretty upset about. Welcome to Evanoch!" That would be bad for a number of reasons. But if over the course of an entire campaign, they met a few interesting groups and got some interesting examples of fashion and had some conversations about parenting and learned about a distant planet and spoke with a veteran of that war, that gives the impression of a full, rich, living world. 

It's almost counter-intuitive. To give the impression of a rich world, you don't want to lead with all of your worldbuilding. You could, but then there would be no story, no combat, no time to characterize the player characters, and no room to relax or be silly. It would be all worldbuilding, all the time. So obviously, we need more of a balance. Some room for story and combat and characterization and silliness. But how much? The answer is also counter-intuitive: it's response, not action. 

Tabletop games are built on improvisation: I say one thing to establish a scene/story, and you say something that validates it and adds to it, and I do the same until we've told a little tale or made people laugh or whatever or goal was. In tabletop games, the players say one thing (an action, for instance), and the GM responds (a consequence, an NPC action, etc). Worldbuilding falls under this umbrella. Anything you do or say as the GM constitutes your time adding to the game. If you spend ten minutes describing worldbuilding, you need a balance of time to do other things, or you risk loredumping, the exhausting experience of having your GM give you loads of worldbuilding information with little actual gameplay. (It happens to the best of us, but never stop trying to keep that balance.)

So treat your worldbuilding details as improvisation additions. If a party adds that they are going to a market area, offer some street food as an option. If a party is in a room with a telescope and an eager astronomer, offer them a glimpse of the stars. If a player character opens up about their parents, let the NPC with complicated feelings commiserate with them. But these are responses. The street food vendor being unavoidable is unnecessary, as is the astronomy lesson. The "parents raised me wrong" speech is only something you should do if the player is into it. 

Think of worldbuilding this way: the point is not to put a bunch of interesting things out there to show the players. The point is to have interesting things ready for when (or if) the players go looking for them. To be honest, there are worldbuilding details I developed over a decade ago that have never come up. There are worldbuilding details I should have developed over a decade ago that I only got to recently. It's an imprecise science, truly more of an art. What will be useful to you will vary. If your world is more narrow, you will have an easier time covering every base. If, like me, you have a very broad world in order to capture more possibilities, worldbuilding will be about breadth too (hence my worldbuilding articles here picking a broad topic and exploring it across every group--the best organized way to cover all bases). But the point isn't to describe every detail. The point is to have something interesting ready to go. 

I'll go back to the example of the burial. It was in the epilogue of a character named Brokk, and it was very striking to Brokk and his player. In this moment in the game, Brokk had just become a Cleric of Nerull, a knight of the balance of life and death, and he had chanced upon the dead body of a woman in a halfling burial ground. Brokk struggled to know what to do next--he was new to being a champion of death and had no instructions, and he hesitated to do anything drastic in the middle of a major city. Before he could decide on an action, a few people came in and set to preparing the woman's body for traditional halfling burial: burning. Brokk knew that he couldn't heal this woman, who he sensed had died before her time, if she was burned, so he acted quickly and raised her from the dead. Spooked, the man preparing the burning ritual left in a hurry, and Brokk gently sent the now-conscious woman on her way. 

Readers, I am a good improviser, but I am not a good enough improviser to come up with "burning" as the most distressing thing that could be waiting around the corner for this woman. Brokk and his player were dismayed. It was a powerful moment, and because I had to pause to confirm halflings burn corpses, it felt official and more objective, so the obstacle it imposed was valid like the rules are. And think about it this way: if the goal is to create memorable worldbuilding details, in what other way would the knowledge that halflings burn their dead be more memorable for this player?

The knowledge of halfling burial was imparted at a time that it mattered--when the player cared about it--and that made it a good worldbuilding detail for what we needed. You could have tomes of details about every town in a massive world, and if you read them off, your gamers would be bored to tears. We're not here to hear a dramatic reading of the Silmarillion. We want to be a part of a story and have fun together. Some worldbuilding helps that. Too much chokes it. If you want to not get weighed down by worldbuilding, you have to chose to offer it more sparingly and trust that a detail at the right time does more than twenty details offered freely. 

That's all for now. Coming soon: reflections on the campaign of a lifetime, an argument for open-ended stories, and what perfect GMing looks like. Until next time, happy gaming!