A General Guide to Dungeon Mastering!

Frank St. John’s Guide to DMing:

This curated list of helpful tips, for dungeon mastering a “Dungeons and Dragons” campaign, is based on opinions I’ve developed from over 6 years of DMing experience.

This guide assumes you already know how to play D&D 5th edition, and are aware of the basic rules and functions of DMing. If you lack this knowledge, there are several online videos and guides that explain the rules and mechanics of running a D&D game (Matthew Colville’s videos come to mind).

This guide mostly focuses on creating an interactive narrative, world building, encounter enhancement, but lacks the social aspects of the game such as; how to deal with a difficult player. My advice is don’t play with difficult people… but there is much better advice for those issues in other places like r/DM Academy.

Please understand Dungeons and Dragons is a game you can play anyway or style you want! My personal preference is a homebrewed campaign in a low fantasy, medieval setting where dark age political tensions run high, children disappear in the woods at night, and the players pay a costly price for poor decisions. So... If you’ve ever unironically used the word “Airship” in your game… you might not like what I have to say… and that’s totally fine!

Regardless, if you play D&D, I always recommend trying to DM at least one game. Who knows, you might love it! Or atleast gain a perspective on the amount of work and endurance it takes to run a fun session.

Game Running

• Before you even start your campaign, host a session zero with your players, where you set expectations for the type of game you plan on running. You can also learn the type of game they’re expecting as well. Don’t be surprised if someone shows up to your accurate depiction of a medieval fiefdom with their anime fursona character if you don’t set expectations!
• If your campaign offers a lot of adventuring opportunities, ensure all your players have proper character motivation for adventuring BEFORE you start your campaign. It is surprising how often players struggle to come up with a motivation behind their risky choices (like exploring a deadly dungeon). This makes exploration more meaningful if there’s an underlying reason for their actions.
• Never plan a solution for an encounter/challenge in your story. Instead plan problems and obstacles for the players to figure out themselves. However, feel free to provide a couple of resources, tools, and allies that they can optionally use. This provides a sense of agency during the game that adds a whole new level of fun, and helps the players feel like they control their destiny, making their successes increasingly satisfying.
• The easiest example of this is a classic bank robbery. Instead of planning the few ways the player can successfully steal the treasure, focus on the security measures the bank has implemented. Leave it to the players to hatch a plan in order to overcome the challenges before them. The better the plan, the lower the risk of them getting caught!
• Additionally you can also provide resources that are not helpful to the situation at all. This way they must make good decisions about what options are available to them.
• The current 5E combat challenge rating (CR) system is way under scaled. If you want a tough fight, throw something that will kill these players. Try subtracting 2 from the original challenge rating to give them a real challenge. Don't worry they will survive (probably).
• Sometimes the players just want to kick ass, so it might be a good idea to throw some softball combat encounters from time to time.
• Dynamic combat is important. Having resources available that both the players and enemies can use to their advantage (terrain verticality is a very simple example) will add a sense of depth and complexity to your combat encounters. On the other hand, simply adding restriction that affects everyone can be challenging/fun as well (i.e. a prison encounter between inmates where everyone’s weapons have been confiscated)
• Have roleplay in combat! Dialogue between the enemies such as; taunting insults, fearful pleas, or persuasive bargaining, can really make a battle feel alive.
• When someone executes a final blow on an enemy's HP, I always ask the player to describe “How do you kill/defeat them?” and oftentimes the player feels rewarded, since they are in full control of how they’re combative victories look and feel.
• For NPC dialogue, I’ve found it’s helpful to have bullet points of anything of importance you wish to convey beforehand. This way you can focus on NPC personality and how they would react to the player's words, as well as what their motivation is for having the conversation in the first place. This can create a more natural conversion between players and NPC’s, versus a scripted encounter.
• Players will never ever give up agency, you can use this information to your advantage.
  • For example - DM: “You are surrounded by 30 gaurds, they ask you to    surrender yourselves…”
  • Players: “NEVER!” (happens every time)
• When it comes to searching for clues in a specific location, it helps to list several areas or items that could contain clues, in the vicinity. This way players can create a general idea of what’s available for them to investigate (ie. the stove, pantry, closet, and washbucket of a palace kitchen).
• Any clue crucial to story progress should be able to be discovered at lower DC’s and because the player decided to investigate the correct places. (versus simply succeeding a high investigation DC (difficulty check) in the general area… they’re not Shawn Spencer from USA’s “Psych”). However, high investigation/perception dice rolls should be rewarded (as long as the characters are looking in the right place) with additional details, hints, lore, or loot.
• A decent example is this description I read to my players when they were investigating an evil witch’s hut for hidden treasure:

“This hut is fifteen feet on each side and packed with ghastly old furniture. Various spell components hang from the low ceiling, ranging from stinking herbs to poultry feet. To the right is a filthy wooden cot, a wicker cabinet, a slender wardrobe. At the back sits an iron tub filled to the brim with ichor, and a small bed with an elegant, child-sized doll propped upright on it’s end. To the left a wooden table, a stool, and a barrel-topped wooden chest reinforced with brass bands. Lastly, all the furnishings are bolted to the potion stained floorboards.”

• Let’s assume this witch is clever. She probably hid her gold in a place you’d least expect, like inside the doll for example. But there’s still a whole list of items in the room that can be inspected! At this point the players want to roll an investigation check. I normally respond with “What do you want to investigate?” They must choose something I detailed in the room. And no matter how high they roll, they might find all sorts of interesting things and information, but they won’t find the specific treasure unless they roll specifically on the doll where it’s hidden. This can create some tension to make the right decision on where to look, especially when they hear the witch approaching!
• NEVER outright ask the players to roll perception or insight, they will know something's fishy (Note: roll any enemies stealth or deceptions checks beforehand as much as possible, since you silently rolling in front of them is just as suspicious). Instead, let them decide when to make the rolls themselves, otherwise, they must stick with their passive perception/insight number. Provide plenty of opportunities for them to actively want to make a perception roll, using sensory triggers.
• For example, mentioning it’s “oddly quiet” in the swamp they are in, or simply describing the door in front of them, count as triggers. It’s all about giving your players a chance to be successful, and room to fail!
• Without details to potentially prompt them to make a roll, they will feel frustrated. For example; A player falls into a trap in a hallway that you failed to provide any details about. Of course they didn’t roll a perception check, that’s not their fault since they are not expected to roll every time they encounter a hallway (that would be a tedious waste of time). But if you give any unique details about the trapped hallway, like “This hallway is especially long given the lack of doors on either side. It’s tile flooring appears cracked and weathered, but it’s walls remain pristine.” The suspiciously specific detail might prompt them to roll perception and detect that it’s trip-wired with a giant crushing boulder that rolls down the hall. This is far less boring and more surprising than simply saying “Roll a perception check”.
• Players love NPCs that are helpful to them, whether it's with information or physical aid (like healing). They despise NPCs that steal the limelight… or worse, steal their kills! (no matter how “cool” they are).
• I cannot emphasize this enough, if an NPC is helping them in combat… Never steal a kill from any of your players, they will without fail, loathe that NPC. This is definitely frustrating when you want your players to trust this character.

World Building

Consider the following when constructing a settlement within your world:

• Keep in mind the settlement's size and population, also how one can directly affect the other. Example: a settlement with a large population, with limited land, often has poverty issues.
• Are there any special additional features that make the town or city unique? Consider this settlement's purpose. What is the location's history?
• What are the people like? What are their beliefs? What are their values? Sometimes town specific events can help describe the area’s locals. A citywide celebration depicts hospitable residents, while rigorous religious affairs portrays a town made of conservative folk.
• A directional landmark to reference can help add spatial awareness to players in a location. Example: If a tower is at the center of town, and you describe the tower as far very away, they know they’re near the outskirts of town.
• A description of the surrounding architecture can help add the local culture and what it values.
• Is there a tavern? If so, what’s its name?
• Consider what types of craftsmen and traders are here to provide the players with goods and services. Are they here most of the time? Or are they simply passing through?
• Know the leadership for the settlement, and the relation they have with their subjects.
• What kind of protection does this place have? What challenges will the players be faced with if they decide to disturb the peace?
• Types of adjectives within a settlement's description give a certain feel to a place. Describing something as “unpleasant” or “vile” may mean the same thing, but each word gives the location much different “feel” based on the literal sound of the word overall.

• When describing characters in your world, a generic description paired with one or two defining features is plenty! Leave the rest to the imagination and let their personality do the work.

Example: A knight took off their shiny helmet to reveal a head of golden hair and a charming smile.

...Did you picture a man? With Blue eyes? Long Hair? Was he tall? Obviously Handsome right? Doesn't matter, if you did or didn't. The point is you filled the gaps, and your players will too. Still, feel free to answer your players if they have further questions about the description, since those details aren’t important, you can make them up on the spot.

• An NPC having a specific emotion or attitude can be a great motivator for players to dig deeper. If they enter a shop, the players are more likely to overlook a nondescript, helpful shop keeper, than one who is evidently anxious or perhaps openly joyful. These emotions will color the conversation to be had. Depending on the reason for this emotion, the interaction could lead to a side-quest or perhaps simply more flavor regarding the location or people therein. An anxious shop keeper may be feeling stress due to a threatening letter of unknown origin. Or perhaps the shop keeper is simply happy  because his budding relationship with the seamstress across the way is going well!
• The less magic powers/magic items there are in your world, the more meaningful and exciting they are when they eventually appear. The fewer people that have access to magic in your world, the more powerful they seem! This can make a mage-villain seem scarier, or make a spell-using player feel more special! This lack of magic can be conveyed through exposition, sure... or simply how common folk NPCs despise it! (people ordinary fear what they don’t understand).
• If you’re playing in a medieval fantasy setting. I recommend using the lack of knowledge and technology in the time period to the story’s advantage, instead of attempting to modernize everything with magic. The limitations of a “low fantasy” world can create all sorts of interesting scenarios and challenges that are no longer possible in today’s world.
• For example, if enemy forces have taken residents hostage in a castle, it might be a fun and difficult challenge to signal the nearby town’s militia for help, without alerting the captors. Compared to the all too common “magic rocks that function like cell-phones,” this is at the very least more interesting! (There’s a reason why horror films have their protagonists start in a place with no cell service, technology removes challenges, which is great for society, but not for story-telling/gameplay)
• Another simple example is perhaps the players need to deliver something from point A to point B in a short period of time. Instead of the boring option of teleportation… make them choose a path of travel between the longer, yet safer, trade roads... or through the faster, yet riskier, monster infested woods! They will always choose the woods, and they will likely have more fun kicking ass!
• Not only are there technological limitations to consider in a medieval fantasy world, there are social ones too due to the limited mindset of everyone during the time. Prejudice is often used in literature as a challenge that needs defeating just as much as the mythical monsters in your world (Game of Thrones is an excellent example). Wicked people in power discriminating against or persecuting others, or even unfair bias as a character flaw,  can be some of the biggest obstacles to overcome! Since your players live in the modern world, their characters are far more likely to spot the injustices in a medieval world that dark age NPC’s wouldn’t notice. Naturally this helps qualify the players as the very heroes they are roleplaying to be!
• Disclaimer; even though the hatred in your world is fictional and portrayed as evil, it’s still important to be considerate of your player’s sensitivity for this type of content. (Sometimes people play games to escape the dangers of the real world, and that’s okay!)

Story Crafting

• The players are not characters in your story. They are characters in your world. This is their story. The whole idea this game was founded on was “collaborative storytelling,” The game’s rules are the only thing between you as table top role-players and a bunch of adults, hopped up on Mountain Dew, pretending in their parent’s basement.
• Describe how the world around them is changing based on their decisions, it doesn't have to be huge or immediate, but their actions must ALWAYS have consequences. Whether these outcomes are good or bad, it certainly helps to see those results with their very eyes (imaginatively speaking).
• Player are dumb, I’m sorry... but they’re so damn stupid! And it has nothing to do with the DM’s poor communication abilities when describing things of importance! ;-) Never expect everyone at the table to understand or remember something important to the story that you’re trying to emphasize, hint, or foreshadow. It’s important to gage your players' knowledge of plot points to determine what they know or have assumed. There are many ways to gain their perspective on the events that occurred. But some simple options are asking them to recap the previous session, or simply have an NPC ask them “What’s going on?”
• Don't assume you or a player won’t roll a nat 20 or nat 1 at any point, especially on rolls that can affect the plot! A plot point based on chance is a terrible one, and can be easily stunted on an unfortunately roll. So I recommend creating plot points based on players' decisions! Instead of locking the story’s progression behind a successful dice roll (that’s out of their control), the story should continue based on the consequences of what they’ve chosen to do, not necessarily how high or low of a roll they get. Nonetheless it's true that all in-game action requires a dice roll, but the decisions they made will determine how “risky” that roll is. This way the players will feel responsible for how their story progresses, and never feel cheated by “bad luck” since they were the ones that put themselves in that situation.
• With this method, it works both ways! You as a DM will can openly roll in front of your players (instead of behind the traditional DM screen), without having to worry about the story getting ruined because you rolled bad, and they’ll never feel cheated!  Not to mention, narratively speaking, if a story is a chain of events… plot points based on chance are the weakest link!
• Careful using magic as a plot device, if you plan on doing so, set the RULES for the magic clearly to your players, and stick to it. Players can get pretty annoyed when they lose an encounter due to magical elements that seem to shift in power and/or behavior based on what’s convenient for the story.
• If you’d like to make a villain scarier, have them battle the players in the beginning of the campaign, when they are low level. Be sure to use the villain’s full power, and take something valuable from them, but leave them their lives. They will certainly remember the villain that wiped the floor with them and will be either determined to seek revenge, or be genuinely concerned they will lose again.
• A bit of withheld information, that the players are aware exists but don’t know, can add an element of intrigue to your story. This is especially interesting if it’s related to a specific goal they have, or is part of a villain’s backstory.