First of all...
You need none of the stuff below to play the game and have fun. Just a collection of clever solutions and observation.
Pieces on the board instead of cards in your sleeve
There is a rule of thumb when it comes to how much magic can be in the story: as much as you want, but it has to be a part of a conflict, not a part of the resolution: Suddenly the main villain can teleport just as you were about to get him - a terrible plot device. But if that was known in the beginning "You need to find and catch this guy who can teleport." - a completely different story, and an interesting one - "How will we do that? Immobilizing spells? Traps? Definitely gonna get some rope."
Quickly roll up the story
DM Guide for 5th edition has plenty of tables to roll and get some inspiration. It is insane how well and consistently good the result is. I initially overlooked them as I wanted to tell my own story. But it doesn't really give you a ready plot, just a bunch of pieces you need to connect, more like a challenge.
Example (my last rolls):
Goal: Protect someone from attackers,
Ally: Disguised monster.
Hook: You find a map on a body, the villain wants the map.
Goal: Help the villain find redemption.
I had a pink fox sent by diety guide players to a body where they found a map and some belongings. Showing those to a villain will allow him to learn that he wasn't betrayed and that he can stop his vengeance. (I hope my players aren't reading this, they haven't finished the quest yet).
The most important thing
In my extremely humble opinion, the most important part of DMs role is to help players focus on the game. And their game is their characters. Most of the things you may dislike or disagree with in rules or tropes of a role-play, actually serves this exact goal:
Cities are often populated by NPCs with little depth, describable by a handful of traits (greedy, shady, cheerful, welcoming...). This to have players deciding how their character interacts with them and not spending time figuring out what kind of character DM have cooked up for them unless of course, that character is mysterious...
Many aspects of the game lack rules, but having rules there would result only in pausing the game for some spreadsheet time. Basically, anything players don't really care about should be cared for in a most casual way. How much water players consumed based on their speed of movement, how many reputation points they gained for a task completed. Would players go slower if they knew that it costs an extra ration? Only if you are playing some survival setting. Would they have declined to have the village if the reputation yield would be lesser? Why would they even know about it?
In the end: everything becomes less fun after a while. The hard truth to face. Will you get bored of playing D&D? Of course not, you don't have an elf's lifespan. If you like your friends and play no more than 1-2 times a week, there is probably lots of fun that can be created. If you'll always be watching movies you like, why assume you'll stop liking making and participating in those stories in favour of sitting still and watching someone's creation. But there are things in the game that stops being new or interesting after only a few hours - hitting some with your mail attack on your turn again and again and again. But that is ok, you do need to punch stuff in your story after all.
Monsters, races and classes have lore associated with them, expectations and history. Those are there to frame the archetypes: elitist Elves, life-loving and welcoming Gnomes (not the Deep ones), troubled Tieflings. But the goal of D&D is to have fun, and getting all the lore-friendliness right doesn't mean the game will be more enjoyable than a session with DM who didn't even watch The Lord of the Rings. So for all the memos below, none of them is a guaranty of a good time, just some clever solutions I want to keep in mind for the future. It is always the unpredictable but fair outcomes of a play that drive the campaign.
It isn't you, it's me
When a player fails a skill check, in describing the outcome I recommend not using phrases like "Your character slipped", "The character couldn't remember" - yes, those feel like the natural and logical way to describe the outcome of a roll. The player did do a skill check after all. But try to instead blame it on the current situation: "The rock was loose and couldn't withstand the weight of your character" or "It got very dark, also the goblin knows this location and knew where to hide the stone so you can't find it". There are a few reasons to do it this way:
This will avoid the Player Characters feeling clumsy.
Hearing "You missed and couldn't hit the door in the right place to break it" is prompting a natural "Then I'll try[ROLL] again" response. But "The door turned out to be reinforced with steel bars" has a more defining sound to it.
In some way, it means that the player is deciding what kind of challenge was in front of him by rolling a dice, which should be DM's power. But I like to think that we are creating the story together. And in that context, it is ok to acknowledge that things are undefined/non-existent until we tell what they are.
DM Guide is full of those. And the more I DM the more I love the tables, often quickly making some during the session. Just the last time players decided to settle in a fort they cleared and make it their home. They have thrown a party with an escort to maybe bring the cult members who are not too far gone to the good side. So, keeping the game PG-13 I went with "What are your plans for the evening?", with players voicing their very casual and family-friendly intent and me making a list of all the characters, groups and important objects that were part of this party, ending up with 12 entries. After, I overlayed the location with a black sheet of paper and said "The party began... and you wake up the next morning with a headache and fuzzy memory of the events". Asked each player to roll d12 twice and in accordance asked them "You do remember something about [ROLL RESULT A] and [ROLL RESULT B], what was it?" The players would come up with a memory involving those two. This way we managed to have this cool story moment by leaving most of it to the individual imagination, and thus not making anyone uncomfortable.
Another cool example of a table is The Royal Dinner Events that I prepared in advance. Simply stating Your character farted would sound hollow (pardon the pun) and not really feel fair. But having that probability on a low roll makes it fair and real. We rolled d8 + d12, which makes the first and last options much less likely. Also, some of the options are mirrored You feel knowledgeable in a topic of the conversation. (Actually, the character isn't and will make fool of himself if tries to talk)" and "You feel knowledgable in a topic of the conversation. (Character actually can contribute with valuable information). Since I roll one of the dice in secret(d12) the player can only assume by his own roll (d8) how well he is doing. It worked well for us. It also made use of the character's Lifestyle. Aristocratic get d8, while Modest end up with d4, leaving some of the best outcomes beyond their reach.
Information as a timer
In a tense situation, for example, where players need to decide between saving the victim or chasing the attacker, ration the information: As they enter the scene, give the first impression. As they move along, give more. When they ask for additional details, make it clear that their character is actively looking around (and spends time) to learn more. Player: Are there any other exits from this place? DM: As you look to your left and right, you only notice one door with a heavy lock on it to your right.
This helps avoid a sense like the games is on pause until the players make a decision. But there are two more things to keep in mind:
Don't do this when they want to clarify something character noticed already.
Ask each player, to prevent one from using everyone's time pool while their characters did nothing.
Ask each player before answering
It is assumed that if the player doesn't say otherwise, he is moving with the group. Which creates that feeling of passivity. Not something that can be avoided entirely. But in certain situations, mainly downtime, I do the following: Ask a player "What do you do?" and instead of giving an answer, I ask the next player, and then the next. Knowing where everyone is I start framing the event While Luthien and Rickon stay in the tavern, Lorely takes a walk to her temple and Talin is searching for his old friend. Which town places does Talin explore?. From the perspective of each player, some time passed from the moment they decided what to do to the moment the activity progressed, which creates a good flow and adds the feeling of time passing. This is similar to how in movies and TV shows they cut from one character to another while he is travelling to a new location.
Rules serve the story
When a character uses his last most powerful spell slot for an attack on the boss, gets a blessing, but fails and then remembers O, I should have used my inspiration I would totally allow him to roll that second advantage dice. Even though, in accordance with the rules, it should have been declared beforehand. The reasoning being that the character was going all-in, he would have used all tool at his disposal.
Having a failed role adds a moment to the story Our heroes gave their best shot but failed. But forgetting an advantage would mean a player failed at the game, which takes him out of the character, out of the world and into the player seat. Also, ideally, the player would just describe his actions while DM guides which dice to roll. So unless I have a suspicion that a player is being childish and intentionally forgets something or lies about forgetting something, there is no reason not to be forgiving about the rules. On the other hand, if the situation is not tense, maybe a casual random encounter, then there is also no harm in giving small punishments. If the caster forgot to mention saving throws on a spell then the creatures get a 1d6 backup, for example.
Not every adventure needs to be about solving a great puzzle. In D&D the DM creates his/her very own world. But I personally feel more engaged when trying to describe the world while hinting at something. Describe a street?
It is a street. Houses to left, houses to the right, and the road in the middle.
But trying to describe a street controlled by a gang, which the party knows nothing about, is likely to prompt DM to consider how that context would change inhabitants and look of the area. Describing this will form some picture in players minds, and after they actually learn about the gang they will be like
I knew there was something shady about this place.
I would argue that the world built on assumptions is more engaging than the one delivered with straight info.
Few things to be aware of:
With secrets in play, don't plan based on the expectation that players will figure them out. This will turn the campaign into a detective one and that kind of thing needs to be discussed beforehand, setting the right expectations and mindset.
The best use of secret info is to keep things consistent. A magic object or shadowy character can have its methods, mechanics, motivations, known only to a DM.
A DM screen, Dice and a sketchbook (easier to use than a notebook). Recently I did make that grid map you see above, but that is optional. One improvised thing that helped streamline the combat was colourful round tokens from another board game. Basically, assign each player colour from the tokens you have (can be any colourful set of objects). And use them to track, whose turn it is.
In my case:
Rogue - Green Paladin - Yellow Warlock - Black Wizard - Blue Cleric - White Enemies - Red
I flip them to remember that the person took their turn already. I keep them so that everyone can see them.
One more thing: tiny colourful sticky notes to put on the board or on the characters. For example, can be used to mark who is affected by Fiery Fire.
Sidenote. When there are other board games around I cannibalize them (with permission) for additional tokens, figures, etc. to show where enemies are.
But keep in mind: if one of your friends has some of those Kickstarter games with amazing miniatures, he may also be one of the people who feel some OCD when one of their games is mixed into something else.
As for digital tools:
inkarnate.com lets you make a map and has some really really good maps.
I also used Dice Ex App (iOS) for when I need to roll like 10d6 or something for an army of enemies.
I must say that one of the most charming and inviting things about D&D is pen & paper. Learning that a sheet of A4 and a pencil, which are usually associated with tedious studying or work, can be used for something so fun, is the true magic of it all.
"Character sheet, pencil, dice - Let's go!"
Tools for online
I'm thinking about playing online. So far I found inkarnate.com to make some cool maps. Also owlbear.rodeo is a very "jump in and play" kind of thing. Minimalistic and all.
D&D Beyond to share character sheets of course.
I did play once and used jamboard.google.com for us to collectively see the maps and paint on them. Mainly, the laser tool that allows us to paint self-erasing lines, similar to the one in Slack.
Second, it is good to have something that allows everyone to see each other's faces and hear the voice. I will try to use the phone for communication and PC for jam board next time. It is cool to think that only a phone may be needed to play.
A creative instinct may demand your story to be something never heard before - an adventure that feels so very fresh and new, unlike so many other stories that seem to remix the same old concepts over and over again. While coming from a good place, striving to be original can often turn into a mechanical habit of replacing familiar things with unfamiliar. Which in turn makes the world harder to imagine. My friend ran a simple introductory campaign that felt very generic in many places, but I found myself extremely immersed because of the sensation like I've heard this story before and should know what is coming. That feeling of familiarity engages the part of our brains that tries to predict the future. Understanding/Anticipating the world makes it feel real. If you ever watched a bad movie with lots of cliche moments and felt like
This is so forced, people don't act like that, there is no logic, I would have done things differently, then that should be your motivation: present a situation and let them decide what is the right way to deal with it.
We need to find a kidnapped person, do we split up to search faster or stay together?
We are being followed: turn around and face them or lead them into a wrong place?.
When asked how I reward individual experience I say it is for something that is important to a character. That experience isn't coming from the world but from the character himself. If Wizard who is obsessed with knowledge is taking unnecessary risks to learn something about a certain object of power, that would be something he gets rewarded for while another player yields not from the same actions.
Music from Skyrim.
Unless I know specifically which music/ambience I want, I'll just put some Skyrim OST on YouTube.
Non-combat initiative rolls
Every time you present players with a situation, before you are done describing it, they will come up with something they want to try. Especially in social situations, the actions of one player may completely undermine the plans of another. Ideally, everything goes smoothly without the need for arbitrating from the DM. But if you feel like the louder player is about to disrupt the ambition of someone shyer, ask everyone to roll for initiative adding a skill modifier if they want to use one of their skills for the action. Optionally, ask players not to discuss something if their characters can't discuss it: if they are trying to be silent and stealthy or if they are in a tense negotiation. After the initiative roll, when it is decided which player goes first, other players may still do it: if it feels like useful assistance to the first player, the first player gets an advantage over any rolls he or she may perform. But if another player tries to do a different thing, then this creates a disadvantage for both players. Also, players can still disrupt the plans of each other, but this way it will be clear that the character has disrupted the other character and not the player dominated another player.
Actions not plans
Can I do a....? kind of question should be met with a You can try kind of response. Encourage players to try stuff and not plan too much. The moment you have a sequence of actions you might as well say Ok, roll a skill check and it is all done. Ideal flow outside of the combat can resemble the time during the combat: DM asks each player what their character does and describes what happens.
Fair > Exciting
A good concept to think about is this It is not an interesting story why players enjoy D&D, but a possibility of one. Just like imagining the current situation on the board, every participant also predicts where it can all go, all the possible outcomes. It is never wrong to sacrifice an opportunity for something "cool" in favour of the overall consistency of the story, a less cool but fair thing.
When the story makes me happy and engaged - nothing else matters. But when I feel like I should step it up, I have a small list of things to consider. Not actual guidelines of storytelling, but certain realities that one needs to keep in mind and hints:
Take risks. Make it that if players were to know who is who and where is what, they would have propelled their way through the story 10 times the speed. This is a bit of an opposite approach to Collect all the objects of power and befriend all the kings to stop the enemy.
"You asked for it". Dropping a big challenge or straight up hurting a character usually has a bad effect on the play. It just looks like a DM is intentionally introduced something negative into the story. The same goes for hard moral dilemmas, with no right or wrong choices. While popular in RPGs, they are not always fun. Make play fun, nice and smooth... until there is a cave and it says Do not enter! None will survive. And players are like We are scared of nothing. Now it is time to start the pain)
How to write it. I was inspired by The Strange Things Starter Set adventure. It has an example of a story presented as it was prepared by a kid. While preparing for the next session I sometimes imagine that I prepare notes for someone else. Nice and simple ideas.
Reading monster descriptions in Monster Manual is like the ultimate way to give an adventure that true D&D flavour.
A more interesting path. An ancient God is trying to take hold of a powerful relic which will allow him to make light into darkness and darkness into light, souls will be extracted from all living things living them wandering husks - what a horrific possibility, we need to stop it!... but, it is kind of interesting how it will look if we don't... right? Like, darkness will become light? What will it even look like? Often the villain and the bad outcome is more intriguing than the idea of saving the world. Just something to consider...
Additionally, having characters who don't just go by the flow but go above and beyond what can be expected makes for a much richer story. Sometimes it is good to answer "What if he tried really hard to make it work?" or "What would have happened if his plan worked exactly as intended".
More isn't better. While "Make the world feel vivid" may have a compelling ring to it, I'd say: "Don't force it". It may seem like giving an NPC some distinct traits, describing in details the inn, giving a name to everyone you encounter, may make the world a richer place. But it is an interconnectedness of elements, not the abundance of qualities that make it feel real. "O, right, this shop doesn't sell exotic items because we already met this criminal whatever-his-name lord guy at a party who told us that he is controlling all the luxury trade around the city".
Don't get this wrong, but keep players ripe for killing. This came to me with experience. I've put lots of efforts into helping each player to make their character memorable and a crucial part of this story, a proper hero... but maybe I shouldn't have. Now if one dies in combat it will feel wrong, now it has to be meaningful, a glorious sacrifice, or it will betray the story. While I may want to make players feel like this epic team, DM's job is really to show them that they are just a bunch of stupid as&^$ls who are about to get themselves killed.
Tell the story straight
I have a range of habits that I try to get rid of. One of them is to start the sentence with "I assume the party is... " - to signify that this statement can be contested if I am mistaken. I do that to save time, and if there are no objections we go on. "I assume the party kept walking while discussing this so now you are nearing the entrance...". And usually, there are no objections, so in the interest of time, this is a win. A nice solution, but it is also one of the things that harm the overall experience. You need to hear definitively that something happened to start imagining it.
This is probably one of the smallest issues one can have, but I use it as an example to explain that these habits are coming from a good place, from good intentions and they feel like clever solutions, which they are. But they are solutions to the problem that shouldn't be solved. Because there is no need to speed up those moments. Better to wait for the players to ask the DM how the road is going.
What is roleplaying
I was looking for a simple way to explain what mindset is needed for a smooth play. What would an average player say when asked "Where do you want to go?", "What do you want to do?". Some will come up with something but I think the big part will say "I don't know, let's do something". So assume that players at the table don't really care too much about what happens (even if it isn't true, they do care). But if you ask them what their characters want to do, they'll answer. They want to focus on the character, DM's role is to help. This may be counter-intuitive, but asking players about where they want the story to go, actually distracts them from the game. So roleplaying is making sure there is a difference between you and your character. If you ask other players that the party should go somewhere they might say "Sure, no problem, we will find a way to have our characters go there".
Just doing what feels natural and figuring out as it goes is the right way. In most cases, everyone will intuitively try to help each other have fun. But when flow doesn't flow, I have a few general guidelines:
You are all making a story. Imagine that every sentence you say will be written in a book.
Take turns - roleplaying should be respectful. Every time you don't know what to do, ask each player what they are doing.
Make sure that it is always clear where the party is (street, tavern, near the entrance).
When a character decides Logic isn't the most important factor. Here are two reasons:
Going God knows where risking your life is not an optimal course of action. Only a one driven by a strong determination, the deep personal motive would do that. So in a way, having the party go for rational and optimal choices isn't always very logical in terms of the story. Party is not logical by default.
Players are expected to play their characters, so it takes time to say anything or make a decision: putting yourself into the character's shoes, the right mindset, just figuring out what he/she would say. Making the right logical decision often requires players to have a debate and debate takes a lot of cognitive effort that often results in players dropping the roles and arguing outside of the story.
If the party does start to discuss the plans it shouldn't feel like the game is on pause. Ask them to role-play the discussion. For example, instead of "Let's go here because..." the player should start with something like "Legolas comes to the table, points at the desert temple on the map and says: Let's go here because...". Incentivises them to worry more about how the character appears rather than winning an argument. You can ask each to make s speech and give inspiration to the one everyone votes to follow.
For characters and NPCs projecting authority and strength is more important than rational arguments in the world of D&D. It is medieval after all.
To that point, a character who defends the optimal path feels less like a fictional character and more like a player himself. And it takes time to think about what your character thinks and what he/she will do, so having this tension where people aren't eager to talk too fast would provide a more enjoyable role play.
In combat ask them not to discuss strategy. Allow their characters to say around 8 words during their turn.
It is probably worth mentioning that many funny moments happen when someone fails at something. Everyone laughs at one of the characters so it is probably worth being ready to remind yourself that your character isn't you.
While I have these guidelines, I also remember that they aren't something that can be enforced as a rule - it would get too complicated and they aren't specific enough.
World of D&D
Not just interesting but also practical. If the story were to take place in our real world, any supernatural event is expected to have a shattering effect on the psyche of anyone witnessing it.
"You are coming back from groceries store, checking your Instagram feed and suddenly a dragon flies over you"
- it is hard to imagine how a common person can react to this, but shock and panic would be the first step. But an existential crisis, to make the story feel cohesive, is not something players often want to reenact much. Default assumptions of D&D are that magic, monsters, gods - all exist and inhabitants are aware of it. Magic may not have a tangible presence in the day-to-day life of regular people, but when something does appear, it would not flip anyone's worldview. While having a strong role-play element, D&D does a lot to make it as natural as possible to envision oneself in your character's shoes. Understanding why rules and the world are the way they are helped me to feel comfortable with classic tropes and use them to my advantage. Everything that allows players to make confident assumptions makes the world more vivid in their mind.
Rules of D&D
I want to write about why the rules are the way they are. Here are some things that can go wrong when it comes to designing the role-playing game, and how it is solved.
It is not very fun when the player is concerned about failing their character. He can worry about losing the battle, but if the prospect of failing is threatening the fun itself - that isn't cool. We are a bit stressed during board games by default, they can be very punishing, especially the long ones. That is why after playing Starlight Imperium one could feel like it was quite an achievement - the game is emotionally taxing. Role-Play Games offer a very healthy solution: even if you fail, it will still be fun. No player who genuinely wants to play the game needs an incentive not to lose. So, when it comes to balancing and giving players some options, there aren't many wrong choices. Your character will fight to the best of their abilities, options allow you to express the character through their actions, not to give player opportunities to undermine the character.
Most rules tell the player "Don't worry about it" to make the game go smoother. They can worry about their characters but shouldn't think too much about the percentages and probabilities of their actions.
It is assumed that no ability, spell or mechanic can't be fun on its own, only in a context of a story. Also, while the effect of a spell is balanced and can't be changed, its visual context can be anything you decide. Even its name should allow you to be at least 50% correct about its effects. Entangle, Magic Missiles, Hypnotic Pattern.
Action/Bonus action, Reaction, Walk. most games use Action points for this. But with action points a number of options you get are huge, and as a result - a number of choices to consider: "Walk far & shoot", "Hit, Evade, walk away", "standstill, hit a few times", "heal, hit once", "heal, shoot, walk away"... and so on. More options than you can process before your turn comes.
While making the first map I sprinkled all the key plot locations equally around the map and left some space in between for side mission. Which was alright, but after visiting all those locations the map would have looked like there isn't much interesting left. Not to complicate the process by too much, I changed my approach by a bit:
Rivers are super important:
a river doesn't split into two rivers.
A lake doesn't have more than one river draining it.
The river flows from high grounds to low grounds.
A river can't split a landmass into two.
I start from routs - an inconvenient one, not a straight line. Maybe using a ship will be needed. Later I'll just need to figure out how to fill the rest of the map so that the routes are indeed optimal (add hills, mountains, dangerous areas, swamps, etc). Complicated routes and alternative paths for some destinations will actually make the map feel useful.
Instead of plot points, I place landmarks around the map first - places that are more visual: mountains, craters, forests. And then the plot locations go to the side from those landmarks.
Place for eyes to rest. Empty chunks (where something could be placed but isn't) is a good way to avoid making the map look cluttered.
As we made up more stuff, more characters came into play, things happened, I made a set of tables for random encounters. On rolling 6 it says "Roll on the Sins of the past table". And into that table, I constantly add all kinds of things that players did: bad and good (so technically those are not sins, I know, but as they say "No good deed will go unpunished"). Probably should have called the table "Echos". Anyway, here are a few things to consider:
d12+d8 table - an example of a simple probability table. It is different from a d20 table because rolling 9,10, 11 with d12+d8 is around 8 times more likely than rolling 19, 20 or 2, 3 with it. So if you put more likely events in the middle of the table and very unlikely ones closer to the start or the end that will give respective probability distribution.
Sub-tables and sub-probabilities. After you get a result on one table, there could be additional branching based on circumstances. In my case, on a d100 table, rolling 1-20 results in a possible encounter. But if the rolled value is above the number of hours they are travelling, multiplied by the danger level of the area, then they avoid the encounter but notice the tracks or see the potential enemy from the distance. So travelling for 1 hour gives a 1% chance of actual combat encounter in a safe area.
Parallel tables. I have one with interesting locations, one with echoes - good and bad things they did that should catch up to them. And one with characters, groups, kingdoms that players have or will encounter. And I could sometimes roll on 2 of them and try combining the results if possible.
I should note that the first example is not perfect since travelling longer should probably result in more encounters, not just a higher possibility. But those tables don't need to form a comprehensive system that dictates everything. Use of the table should start when DM feels like "I need a random idea right now".
Optional Rules & Homebrew
If life gives you lemons, make lemonade. If D&D doesn't give you enough rules for resting in a dungeon and travelling, make some that are tightly tight to your story. There is a filthy sewer system, resting there will prompt a roll on a custom table, that takes into account your Constitution modifier and swaps some dice based on your lifestyle (Wretched person's immune system may already be well accustomed to most of the filth floating around). Get some disease, wake up with no hit dice.