J.M. Black – Media Shenanigans!

Sound Designer, Writer/Director, Storyteller


20: Natural 20!

Hello hello!

Anyone who knows me, knows it’s inevitable I’ll mention D&D at some point. It’s a matter of time, but it usually does happen pretty early whenever you meet me!

Dungeons and Dragons changed my life. Personally and creatively. So this week for our 20th post we’re going to do two things. This will be split into two separate posts, releasing on the same day.

In this post, I’m going to explain what the game is, and give 20 tips for new Dungeon Masters who may have run a game before, but are needing guidance on improving how they run the game! I’ll also share resources underneath from Game Masters more experienced than me, who I learned from and who make learning about this fun and easy! This is gonna be a long post, get drinks and snacks!

In the second post which will drop this afternoon, I’m gonna take you into a game I’ll be running soon with my regular group, and talk about what needs to happen in the first three sessions in order to set up the wider narrative and orient the players in the world!

But first – a little context if you don’t know! What is this game?

What Is It?

Dungeons and Dragons is a Tabletop Roleplaying game (TTRPG), usually set in a high fantasy world like Middle Earth or Narnia. This world can come from a pre-written adventure (the worlds of The Forgotten Realms, Eberron, Exandria, and so on), or you can make your own world up!

But the core of the game is you (as a player) make a character (your avatar in this world), and you go on a make believe adventure with your friends by acting out what you do! The Dungeon Master (kind of the referee and host of the game) describes where you are, plays the people and creatures you meet, and provides the problems you have to solve. You then describe what you want to do, and roll a dice to see how well you did (natural 1 is the worst outcome, and natural 20 is the best on the iconic 20 sided dice!).

Games can last minutes, or run episodically for years. I’ve played games that wrap up in an evening, or after two years – and it’s always a fun time with the right group of people!

I could talk forever about D&D. You learn a lot of skills both playing in and running these games (depending on your preference). Scheduling, resolving problems, teamwork, managing time, organisation, efficient notetaking, creative thinking – all of these and more! The game’s influenced my creative skillset so much, and continues to enrich my professional life the more I play!

But this post we’ll focus in on the game itself. Relatively new Dungeon Masters/Game Masters, this post we’re going to speed through 20 tips for running the game! The resources at the end will be useful practically for the first game prep wise, but the 20 tips will be general advice for your early days running the game – which I learned through trial and error as I ran my own (from late 2017 to present!)

First – an aside on Organisation!

Okay so something I won’t talk about much in the tips is how to practically organise a session, so I’ll mention quickly how I do it here!

Put simply, I use a word document. At the start I write a paragraph of prose describing where the players are, some story stuff, and just set the mood. Then each encounter will follow roughly the same pattern:

  • We’re in a place! (Describe the place, and have notes on what or who is in the place)
  • Something happens in the place – danger, a puzzle, conflict!
  • Then notes on how the players could approach the thing happening in the place. Once the players resolve the scene, we move onto the next!

However you work best, find your system and organise your notes this way. Some GMs prepare a lot – like Dael Kingsmill, who in her DM binder video shows how she writes entire passages out in blocks in her DM notes for running a session. Other GMs lean more on improv and run games from single sides of A4 and brief notes – like Anthony Burch in some of the Dungeons and Daddies live shows.

As long as you feel confident and have access to the information you need during a session (from memory, on the page, or improvised), you’re doing it right! The players don’t know what you have planned. So if you forget to include anything or have to change things on the fly, they’ll be none the wiser! I’ve ran games on months of prep, or from zero prep on the page – and either game can spark joy in your players because they’re playing and wanna have a good time!

20 Tips For New DMs:

Think Like A DM:

1. Rule of Cool.

The “Rule of Cool” is a well known one in this hobby! If it’s cool, you can allow it to happen! The rules are a guide, and you are the referee. If your player feels like a spell could be used in a creative way that isn’t in the rules as written (RAW), and you wanna see it happen too, then let them do it! This game is SO COOL when you make these rulings!!

2. Yes, And!

“Yes, And!” – there will be exceptions, but the golden rule of improv works very well with D&D (which is essentially improv with dice). If your player makes up that they can see a cool elf in the tavern – make up a cool elf! If they comment that their home town is a little run down but they throw great parties – take note and make sure there’s a party when they visit there! Life’s too short to be precious, let them have their fun too with casual worldbuilding!

3. Redirect Energy.

If you do have to tell a player “No”, try not to shut them down. Take a leaf out of Brennan Lee Mulligan’s book (Dungeon Master for Dimension 20) and redirect their energy. See what kind of effect they’re trying to achieve and figure out a way for them to have fun, while not breaking the game.

New players may be nervous and unsure of what they can do. As their DM, try to make sure they feel comfortable and are getting involved, while letting them know what’s possible in what they’re asking! Check in on them and keep it light, it’s a big game to dive into for newbies!

4. Don’t get attached to your plans.

You’re not the only storyteller at the table! Your players have a say in where it goes too. You can steer them in secret ways (like moving a dungeon they missed to another place, or having a secret revealed by another NPC), but make sure that the players have agency and make decisions for themselves. You can always adjust and plan around what they’re doing, so never get attached to your original plans. They’re gonna change! And that’s what makes the game so exciting!!

5. Follow the fun, but don’t write yourself into a corner!

Absolutely Yes And, and follow where the players go. But if you know that there’s nothing in that stable for them, or you need to subtly turn them around back towards where the session prep is – you’re allowed to do this! An example is this:

Your party is investigating a werewolf sighting in a rural town. They suspect a spooky farmer to be involved in a conspiracy. That may not be true, but sure okay – you adjust and give the players something to find in his farmhouse. A scroll of secrets, maybe. They come to the conclusion that he’s the werewolf!

If this isn’t true, and it’s important that another NPC is the werewolf, absolutely just have them roll a dice to investigate and tell them their hunch is wrong – but tell them something that gives them cause to investigate elsewhere. “It looks like the farmer’s just a human guy, but the notes have handwriting that looks like the mayor’s… Maybe this is a new lead.”

This is redirecting the players’ energy when it comes to story stuff on your end – some ideas they have are cool and you’ll be tempted to make them true. Others you can dismiss and have them look elsewhere for what they need!

Knowing Your Players:

6. Know your players’ backstories.

Player backstories are the fun bit, but writing’s not for everybody, so see what the player’s feelings are on it. If they have pages of backstory – gladly take it, and try to incorporate some hooks into your story! It’ll make their heart sing to hear a reference to a person or place they know, or see them in gameplay. If the player isn’t super into backstory, that’s alright too! We discover these characters during the game anyway, and it may be that some lore is revealed through play – or not at all!

One time I played a character with a two sentence backstory (feral gnome child who lives in the jungle, no one knows where she came from), and this was okay because discovery happened during the game on what the character was like. Most important thing is are they having fun? If the player likes backstory, be open to it. If not, then ask a couple of quick questions if you need them, but otherwise keep the conversation brief!

7. Ask your players what their wants and desires are.

Feel free to ask the players questions like why they adventure, where they’ve come from, and what their wants and needs are – as all of this helps better understand the character.

Do they want money, friends, power, adventure, discovery, to fulfil their curiosity? These are wide base needs that most characters will have, you’ll get a sense from talking about them what camps they may fall into. More specifically do they want to find a certain artifact that will bring them success in their field, or are they looking for a missing family member, seeking revenge on a villain? The specific wants are very powerful for hooking your players in parts of the story.

What they need is different though. But they’ll probably discover that on their own. They may want revenge, but need a group of people around them to heal with. They may want fame and fortune, but only need their close family’s approval after being denied it so long. They may want gold but need the adventuring lifestyle as it makes them feel alive and they wouldn’t trade that for any amount of money!

8. Give the players challenges that let their unique abilities shine!

Have someone playing a rogue? Give them a moment to pick a lock or be sneaky! Have a paladin or cleric? Give them a moment to let their holy power shine through, or a temple to visit. Druid? Surround them with animals to control, a tree to talk to. Bard? Literally give them a stage – let them perform, be they musician, poet, breakdancer, whatever storyteller they are!

Players want to do cool things with the class they chose, so let them do it! Write these moments into your sessions, or improvise them if it feels right. If your players look for these moments, make sure they find them!

9. Give the players reasons to stick around together.

Generally, people playing D&D want to adventure, and there may be a little suspension of disbelief on why five strangers would travel together. But give them reasons. If they’re strangers, have them work for the same person or guild. Or friends of friends with a common personal goal. If the characters know each other – this is fun too! A found family travelling together. Or an adventuring party who worked together years ago and is getting together to solve one more mystery!

World of possibilities! Talk with your players during session zero (which we’ll get to in a bit), and give them reasons to hang out with each other. A way I’m doing this with my current game is giving them each things they’ve heard about the other characters (to build curiosity between them) and having them recruited by the same guy for a secret mission!

10. Use the trinkets table in the Players Handbook!

This is a quick one I like to do. There’s a trinket of 100 trinkets in the Players Handbook (page 160-161, or in this link), and I like to give each player a trinket at the start of the game. This will be a random thing they’ve found on their adventure like “a tiny silver icon of a raven”, “a mummified goblin hand” or “a metal urn containing the ashes of a hero”.

This could help give you, the DM, story ideas – or be something of interest for the players themselves if they find themselves curious about that “book that tells the story of a legendary hero’s rise and fall, with the last chapter missing”…

Running The Game:

11. Balance your combat encounters – use Kobold Fight Club!

Use Kobold Fight Club to balance encounters. Combat is hard to measure, and there’s not a perfect science. With time you’ll know what your players can handle, but Kobold Fight Club, or even premade module encounters from published book adventures can help give you a sense of the kinds of enemies your players can handle at the level they’re at.

12. Track initiative in a way that makes sense to you!

Using the regular initiative system, you’ll be taking down numbers to determine the order the players and monsters go in combat. And there are lots of different ways of doing this!

My favourite comes from how Matt Mercer from Critical Role works, which is he calls for initiative in number brackets (20-25, 15-20, 10-15, 5-10, 0-5) – which gives him time to note down each player and in order from top to bottom.

You can also just go around the table and note things down this way, whatever makes sense for your setup and group – do it!

If using a word doc or digital notes app – I use Initiative-Name-AC-HP as a format for noting character initiative in combat. Like:

15-Theadosia-AC16-HP-74

That way the turn order is first – so reordering a list is easy as its readable, you’ll always be able to see the armour class (how hard they are to hit with an attack!), and HP being last makes it quicker to click to and easily edit as monsters lose health points!

13. Make NPCs distinct – what’s their motive?

When playing NPCs (Non Player Characters), try to give the players a visual, and remember they’re taking in a lot of information. If you can make five NPCs into one, then do it. Tell the players what the NPC looks like, their name, and if you like voices then give them a voice (you don’t have to, but this makes distinguishing them easier).

On voices, even a slight pitch shift, or speaking out the side of your mouth, or a light accent (even if you’re not good at accents) will help bring them to life! Consider what the NPCs want, what they think of the players, and any secrets they might have that could help the players in their journeys. Persuading NPCs will be a flexible gambit – but just follow your gut. DC-5 is easy, 10 for medium difficulty, 15 for hard, and 20 for very hard. DCs can increase or decrease in your head depending on what the players do to sway the NPC’s mood.

14. Plan session for what you need. Ask your players what their plans are!

If your players want to go to the Temple, then the Town Hall, then off to fight the dragon – prep those three places specifically! You can improvise if they go elsewhere, but you know what to expect from either the players talking in character, or discussing out of character.

If you don’t know, and wanna know, it’s okay to ask!

“Hey so I know what to prep, where are you thinking of going next session?”

It saves you prep work, and you won’t have to guess!

15. Pace a session smartly, but always be flexible to change!

With time you’ll get a better sense of how long things take. Combat is long in D&D 5th edition, and was long in editions prior. You could see a combat and think “okay this will take the full session”, and take note of this. You could think “they’ll only spend 10 minutes here” and still be in that tavern talking to “Boblin the Goblin” after an hour.

There’s not an exact science to it, you just gotta make sure the players have fun. I like to end sessions at satisfying points. Cliffhangers are a favourite, but a calm sunset ending where all’s well is nice too.

For pacing especially, I draw a line across a landscape A4 sheet of paper, and draw dotted lines down the page intersecting at where the 1 hour, 2 hour and 3 hour marks would be (if the horizontal line represented “Time” on this graph). Then I’d write out the encounters the players will come across, and track where they are during the session. This may be exact (eg. “They fight the Bugbear!” – 45 mins), or vague (“They investigate the mystery” – 30 mins). But it allows you to look ahead, and mentally shuffle things the players will do or discover so that if story needs to happen, it can happen in what feels like an organic way for them!

Tips on long term running a campaign.

16. Session Zero. Have a chat, safety tools, what the players find fun!

Before you play – meet up and touch base! Safety is important, and it’s important to know what everyone is comfortable with being in the game. Violence (and the level of it), horror and gore, real world topics, sex (yup, that’s a thing in some games!), all of these need to be approved or ruled out ahead of time so folks are comfortable while playing. This consent in gaming form is useful for this.

I also use the traffic light system which makes it clear that if players want to slow down and talk about a scene – they can call out “yellow light” and we can make accommodations based on comfort levels. Or “Red light”, which means we skip a moment entirely and move onto the next thing. no judgement or questions asked (though a follow up afterwards is important).

Making sure everyone feels safe and is having fun is the most important thing. And however you do this with your group, just make sure communication’s open and that y’all are on the same page!

Session Zero’s also a fantastic time to figure out what you enjoy in a game! Mystery, puzzles, monster fights, drama, shenanigans – you can establish tone and what the players can expect in this session, and adjust your game based on what they like if you want! Some players prefer combat, some prefer roleplay, some like both – try to strike the best balance so everyone has fun!

This is also a time, if characters have been rolled up, to figure out how the players may know each other and any backstory links you can find before the first session. Like two fighters knowing each other from an old guild, or a sorcerer knowing a wizard because they studied at the same magic school!

17. Session length, figure out a sweet spot for you and your players.

This depends on a few factors, but you’ll find a sweet spot. It may be that you can only play in evenings, so realistically have 3-4 hours to run a game. You may have longer, and if players are down, longer games can be fun too. Some players, neurodivergent folks for example, may find longer games harder to concentrate on – so would prefer a 3 hour game (with breaks if needed) to a 6 hour one.

It’s all based on what time you have, how much you’ve prepped, and what everyone’s comfortable with! Personally I like a game between 2.5 hours and 3 hours. This gives time for a combat encounter and some story stuff, or just one of those things. You can have combat heavy games, or story/social encounter/exploration heavy ones individually too! But it’s good being able to run a game in the length of the average movie, can do plenty in that time!

18. Scheduling – find a day if you can!

If you can find a common day and time to play – scheduling is the big boss enemy of D&D! Having a slot to play that everyone can comfortably make is the hard part of running games, and the holy grail if you can get a regular game going! Whether it’s weekly, once a fortnight, or monthly – figure out how often you and your players wanna play and see if you can make it happen! Scheduling’s a constant discussion, so keep communication open!

19. Macro level planning – story arcs. Satisfying places to leave the story!

Longer narratives need a pay off every now and then to feel satisfying. It’s why videogames have mini-bosses to defeat, and why TV series have mini story-arcs that resolve every few episodes. In D&D, you may run a game for 10, 20, 30, 40 sessions. You may play a game for years. But the game also may be cut short unexpectedly.

Make sure that there are points in the narrative that make the players feel accomplished, and that would be satisfying to leave the game on a high note. You can have unanswered questions and build up to the big finale – but give them a win every now and then when structuring the wider story! This’ll keep everyone pumped and engaged with whatever comes next, or satisfied if the game runs its course early.

20. Have fun! Always! It’s a game, don’t get too bogged down by things!

This has been a lot of tips, and a lot to take in. But remember that kids play this game. Every kid on the playground is playing characters and making up rules and having fun – this is just that but with dice! As long as you’re having fun, that’s all that matters. You and your players enjoying yourselves (and the DM IS a player, so make sure you’re having fun too), is the most important thing. So go do that! Have fun!!

This was a long one, thanks for reading and I hope there was something useful in there! And thank you to my regular D&D group and to Mika for providing feedback on the tips – this is an ocean of a topic to narrow down, but hopefully the main bases are covered!

Here’s a few more resources that are useful for beginners that I recommend checking out!

Matt Colville’s “Running The Game” Series. – Colville was the first I learned from, his advice is fantastic and the first episode shows you how to plan a full session easily!

Matthew Mercer’s “GM Tips” Series. – Great for improving your skills GMing as you go, a wide range of tips and tricks in short episodes!

Runesmith – Writing an RPG Session. – a checklist of stuff to do every session to keep things fresh!

Aabria Iyengar’s Flowchart Method. – for keeping track of abilities!

Dael Kingsmill – MonarchsFactory – for imaginative ways of thinking about the game and redesigning monsters and lore!

Adventuring Academy – A series of interviews held by Brennan Lee Mulligan, talking with other GMs and figures in the online TTRPG world about their approaches to running their games! (also available as a podcast)

Power Word Spill – some very good tutorials, and interesting uses of tech with running D&D both in person and online.

Learning Roll20 by CrashGem – A brilliant series that teaches you how to use online tabletop software Roll20. If you’re playing with friends online, Roll20 is a good free software that could suit your needs!

I also recommend watching actual play shows to get to know the rules better, and get inspired by GMs doing this professionally! There are so many out there – I’d just have a google around and find a GM who you resonate with and a group you enjoy watching! Here are the ones I watched/listened to that inspired me when I was first learning, and some recent picks I’m enjoying now!

The Adventure Zone – (Podcast) for goofs and bits!

Critical Role (Campaign 2 Episode 1) – (Webseries/Podcast) for nerdy ass professional voice actors!

Dimension 20: Fantasy High (Episode 1) – (Webseries) for fans of John Hughes movies and Dropout (formerly College Humour)

Not Another D&D Podcast – (Podcast) for shenanigans and a small party!

Dungeons and Daddies – (Podcast) for those who like chaotic decisions, game design innovation, and family drama!

DesiQuest (Episode 1) – (Webseries) It’s new, it’s Desi, it’s so much fun!

But honestly, running a game is a leap of faith! You’ll learn by doing it, and as long as your players are having fun – you’re winning! They care more about feeling cool and having a good time than that one rule you forgot, a monster going down too quickly in a fight, or the fact you panicked and called one elf “Brad” because you couldn’t think of a name!

Just have fun!

Until the next time, dear reader, roll ALL the Natural 20s!

-J

Joke of the Day:

Q: What’s a Dungeon Master’s favourite italian food?

A: Dungeon-Pasta!



One response to “20: Natural 20!”

  1. […] read the beginning of Post 20 for setup, but long story short – Dungeons and Dragons is a fantastic game, has changed my […]

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