Dungeon Mastering 101: Designing A Quest, Part 2

This is part 2 of a series of articles about designing quests. In it, we examine the three pillars of gameplay and how you can use them to make your quests more engaging! You can read part 1 here.

The adventurers have learned of the location of the goblin king’s stronghold: an abandoned castle near the old border. It is a day’s travel from the town that’s sprung up at the new border over the last fifty years, where the party has been staying. With their destination in mind, the adventurers set off. In short order, they find and clear the castle, lay claim to the bugbear chief’s hoard, and made it back with little fuss.

The players are satisfied, but not really all that impressed. The adventure seemed a bit rushed, or maybe unimaginative. The journey there and back was handwaved with a travel montage; the castle was fairly straightforward, consisting of a series of rooms leading to the boss; and the final encounter was a big fight that ultimately amounted to a race to reduce the other side to 0 hit points—a race the characters won because they were at full strength.

Every DM has been here. Whether it’s because you’re new to writing your own quests or because you just didn’t have enough time to come up with something a little less straightforward, sometimes what you churn out is good, but not great; fun, but not memorable; ready, but not complete.

In this article, we’ll look at how to use the three pillars of gameplay to round out your adventure, and how to push them in ways that will make the adventure unique.

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The most structured of the three pillars of D&D, combat is all about defeating one’s opponents. Of course, there are many ways that this can be done, whether that be the physical steps by which you go about defeating your enemy, or even exploring what it means to defeat your enemies. There are very few adventures that don’t engage this category of gameplay, and most characters are designed to have at least modest combat abilities.

Because it is so important, it is also extremely difficult to truly innovate, as many people have already experimented with it. Fortunately, combat itself is already complex enough that there is little innovation that is needed for the system itself. Revising the system should be done only for special circumstances, as you risk making certain playstyle decisions obsolete when you alter the rules. Rather, an interesting battle location will have a significant influence on the fight and challenge players to constantly think strategically.

The following are two sample ways you can push combat for your game.

The Bridge

It is a plain truth that most combats in D&D don’t make extensive use of elevation differences, terrain hazards, or other environmental features. There’s nothing inherently wrong with this, but it makes for a welcome change when the battle is set somewhere unique that adds another layer to the challenge. A bridge is a perfect example.

Try placing an encounter on a stone bridge, roughly 80 feet long and 15 feet wide, with a half-ruined gatehouse on one side which has been occupied by highwaymen. Two or three archers rain arrows from the second (intact) floor of the gatehouse throughout the fight, while five or six melee fighters fight on the bridge.

Fighting on the bridge is complicated by the possibility of being shoved over the edge using the rules for shoving a creature (PH 195). A creature that is shoved over the edge falls 40 feet into the river below. That creature must succeed a DC 5 Dexterity (Acrobatics) check or suffer 1d6 bludgeoning damage from impacting the water awkwardly. The river has a current of 3 miles per hour, and swimming against the current requires a DC 15 Strength (Athletics) check. On a fail, they are moved 25 feet downstream away from the bridge as they progress toward the shore.

For added effect, be sure to have a particularly hulking foe among the enemy ranks who has a higher Strength score. He doesn’t need to be any tougher than any of his friends, just his presence and distinction will cause your players to focus on him and feel that extra pride when they defeat him—ideally by tipping him over the edge.

The Duel

This is an example of changing the rules for a special occasion.

One of the characters has been challenged to single combat with blunted weapons. The goal is to physically strike your opponent three times before your opponent strikes you three times.

Because normal combat and attacking is ambiguous, with each Attack action encompassing the various feints, lunges, parries, ripostes, minor hits, and deflected blows that would occur over a period of six seconds, such a challenge as this requires re-envisioning the process. The following changes apply:

(1) Each round is between 1 and 2 seconds in length, and a single Attack action involves making a number of actual attacks equal to the number of attacks that character makes as part of the Attack action. For example, a 1st-level fighter would make one physical attack, while an 11th-level fighter could make up to six physical attacks (using their Action Surge).
(2) Each contestant’s AC against a physical attack is 10 + their Dexterity modifier + their proficiency bonus. This represents their ability to evade and deflect strikes. Armour does not have any effect on AC for this contest, as a strike counts as a strike whether the individual is wearing plate or cloth.
(3) As a reaction, a contestant can roll a die and add the result to their AC against one attack that is made against them. The die size equals the contestant’s proficiency bonus. To simulate rolling a die with a number of sides that does not correspond with existing dice (such as a d3 for a +3 proficiency bonus), choose a die that has a number of faces that is a multiple of the proficiency bonus and divide the result by that multiple (rounding up). For example, a d3 could be simulated using a d6 (dividing the result by two) or a d12 (dividing the result by four). A contestant can roll this before or after the triggering attack roll has been made, but before the result of the attack has been determined.


Encompassing everything from the small-scale interactions with an individual dungeon chamber to the large-scale travel between various locales, this pillar is an easy and fun category for a DM to use as their playground.

The appeal for pushing this adventure pillar is exemplified in the ubiquity of location-based adventures. Entire mini-campaigns such as The Keep on the Borderlands (originally 1979, now converted to 5E) have been created based on the idea of exploring one (larger) location, and perhaps the single best module ever written in Dungeons & Dragons history, I6 Ravenloft (1983), was entirely set around one locale—the eponymous Castle Ravenloft.

At the other end of this spectrum are sandbox adventures. These are adventures that allow players to explore anywhere they wish, with loose hooks for a central plot scattered throughout various destinations, some of which may be thousands of miles apart. The recent hardcover adventure Storm King’s Thunder (2016) is a perfect example of this style.

These two styles can be blended in a single quest on a sliding scale, and doing so is a fantastic way to give your players greater autonomy. One of the best articles that we ever read, written by The Alexandrian, talks about how the legendary game designer Jennell Jaquays used this approach to make a great many classic adventures. The secret is in creating a complex environment that allows players to choose, though there are some more tips to be gleaned from that article, which we strongly recommend you read.

We said in part 1 of this series that the fewer locations you have in a quest, the more interesting they need to be. A single location where you centre your quest can (and should) be more complex than a simple series of challenges leading to a slightly stronger, final boss. Adding side passages, optional encounters, back doors, and more will greatly improve your quest and encourage players to feel that their choices matter.

And let’s not forget traps! A full discussion of traps is better contained in its own article, but we can’t close off this section without a brief note on the subject. Traps are often viewed as a way to satisfy one of the adventuring day’s encounters—just throwing damage and XP at the party—but they can be so much more. A trap can illuminate and reinforce the theme of the dungeon, especially if it is a complex trap (we highly recommend that you check out Xanathar’s Guide to Everything for more about complex traps and other tools you can use to improve your game). A dungeon inhabited by kobolds may have a variety of crude (but very deadly) traps, while a mummy’s tomb might have magical traps that lay curses.


More than any other pillar, this category of gameplay is heavily dependent on the DM and the players, providing for a unique experience with each table.

The key to pushing the boundaries of the social category and getting the most out of this adventure pillar is really for the DM to create interesting NPCs for the players to engage. Spend some time thinking about the lives of the NPCs outside of their interactions with the players. Have a few well-fleshed-out NPCs around that the players can encounter, driving the story forward. Consider especially how they would respond to different approaches to social interaction. If your players succeed in capturing a goblin scout and want to convince it to reveal the location of the goblin lair, for example, there are three ways to do it: through guile, through coercion, or through diplomacy. What would its reaction be to these different approaches? Is this goblin stupid enough to be duped into revealing the location? Is it cowardly in the face of threats? Is it too savage to properly respond to diplomatic entreaties? What might make it more amenable to such an approach?

A lot of Dungeon Masters find the prospect of going through this pillar freestyle to be daunting. Fortunately, chapter 8, “Running the Game”, in the Dungeon Master’s Guide has a fantastic and sadly oft-overlooked section on Social Interaction that distills the process of running this pillar into three easy steps (with a possible fourth, depending on the situation); offers suggestions for using ideals, bonds, and flaws to drive a social interaction in an organic fashion; and includes a helpful guide for how to handle the inevitable Charisma check that players so often crave. When creating your quest, give some thought to these tools and how they can be used to make the encounter more memorable. Additionally, if you are struggling with what the creature can reveal, it may be easier for you to spend some time while preparing the adventure to write down some points that cover what different NPCs would know, which will allow you to use them to guide the conversation later on.

For example, Lady Elethea Moonsong is the Mistress of Mysticism to the royal court, a prestigious position that sets her as the foremost authority on the arcane within the kingdom. She suspects that the origin of the king’s ongoing illness is with the queen, who has taken over much of the kingdom’s governance and has been pushing Lady Moonsong to the periphery of court, excluding her from important meetings and promulgating anti-sorcery sentiments that discourage her fellow courtiers from associating with her. The ultimate reasons for this would be tangential to the plot the characters are following.

When the characters seek to enlist her aid against the cultists whom they believe are working for the queen, they must make a compelling case for Lady Moonsong to consider being party to treason. Prior to the interaction, the DM has determined the following characteristics for Lady Moonsong:

Ideal. Responsibility. “It is the duty of those with power to protect those without it.”
Bond. “I work to advance the cause of responsible use of magic to the betterment of the kingdom.”
Flaw. “My pride will be my undoing.”

As a veteran of the royal court, Lady Moonsong is good at keeping her true feelings hidden, so the DM sets the DC for a Wisdom (Insight) check to learn one of these characteristics at Hard (20). However, the DM also decides that if the characters can frame their request for aid using one or more of these characteristics, it will reduce the DC for the Charisma check to get her on board by 5 for each characteristic used, starting from a base DC of 25.

Throughout the encounter, the DM will drop other clues about these characteristics. The wall in Lady Moonsong’s office is hung with awards and other distinctions and decorations she has earned (indicating that she is highly accomplished, but also prideful); there is a worn copy of a well-known book on social responsibility sitting on a chair by the hearth (indicating her ideal); and in her outgoing mail is a letter authorizing a donation from her personal account to a charity that fosters magical education among talented youth through a local temple (indicating her bond). Noting these should require predetermined passive Perception scores or active observation of the room, and can make it easier to discern one of Lady Moonsong’s characteristics.

The DM might devise a few short responses to some expected statements or questions from the party, but most of the guidance they will set for themselves would be in the form of bullet points such as these:

  • Lady Elethea Moonsong is a middle-aged human wizard who has used magic to maintain her youth. (If the characters ask around about her, they will learn she’s held her position for 15 years, but she appears to be in her mid- to late-20s.)
  • Elethea has been harbouring suspicions about the queen for a little over a year. These suspicions have worsened as the king’s health has gradually failed.
  • The primary reason for Elethea’s suspicion is because she chanced to catch a spy infiltrating her home last year. While she was interrogating him using magic to read his thoughts, the spy managed to imbibe a vial of poison. As he expired, the spy’s mind slipped enough that Elethea distinctly heard him think, “I’ve failed you, my queen, but not betrayed you. Please forgive me.” It wasn’t enough to lay the blame before any specific queen, let alone this queen.
  • The spy had been in the midst of searching Elethea’s library and had retrieved two tomes, both on advanced magical theory relating to <<insert your plot hook here>>.
  • As the king’s condition has grown worse and even magical healing has had limited benefits, Elethea has pondered who stands to gain from the king’s incapacitation. The queen, with her family’s considerable influence in the kingdom, is an obvious candidate.
  • Elethea needs proof if she is to move against the queen. The characters may be able to supply this if they have some way of unequivocally tying the queen to cult activity.

These six points contain everything the DM needs to guide the conversation between the characters and Lady Moonsong. After the conversation has run its course, the DM calls for a Charisma check (with any applicable proficiency bonus from Deception, Intimidation, or Persuasion) and determines the result of the encounter.

If the party succeeds the Charisma check, Elethea becomes their ally in this endeavour. If the party fails, Elethea may not trust them and send them off, but keep a careful eye on their activities and arrange for certain clues to come into their possession. If the party fails spectacularly, Elethea may have them arrested on charges of treason and observe their behaviour, covertly facilitating their release after a day or so if it becomes clear that they are not agents of the queen, with a lead for them to further investigate Her Majesty’s possible duplicity and gain the evidence needed to bring the quest to a close.


The three pillars of gameplay each offer a particular method to engage the players. Some adventures will lean more heavily on one pillar than others, with combat being a particularly common focus. If the pillar is used in new and fun ways, even a fairly simple quest can make for a positive, memorable experience for your players. Don’t be afraid to improvise and innovate; as long as it’s in the spirit of empowering players and having fun, you will have a hard time going wrong.

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