How to organize your first session as a Dungeon Master

Lucas Taylor
7 min readNov 30, 2018

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So you’ve found a group to play with and you’re ready to schedule your first game?

Congratulations! That’s awesome, and you’ve taken your critical first steps in your journey in playing Dungeons and Dragons!

Now it’s time to plan out your first session.

A good session can be a magical experience for people, with memorable characters, high-stakes action, and spontaneous adventure, as the players meet challenges and create solutions.

This takes a lot of preparation from the Dungeon Master (DM), but once you put in the work, you’re sure to have a fun evening.

Must-have supplies for the game table

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Given the nature of Dungeons and Dragons, there are some supplies you’ll want easy access to while playing.

Rulebooks

You’ll need a copy of whatever rules you’re using, along with any expansions or supplements that deal with a player character’s abilities.

This can add up to a lot of books. Player’s Handbook, Dungeon Master’s Guide and Monster Manual are the basics. If a player used a particular expansion during the creation of their character, it’s fully appropriate to ask them to bring their copy.

Dice

If there are too few dice at the table, the game is still playable, but things can slow down to a hellish crawl. At the very least, every player should have their own full set of dice. A full set means a four-sided, six-sided, eight-sided, 10-sided, 12-sided, and a 20-sided.

Writing implements

Every player (including the DM) needs a pencil and some paper for scribbling notes. Keeping a supply of blank character sheets is also a really good idea.

Minis

A lot of DM’s, myself included, use miniatures to keep track of actions in combat encounters. These work best if you use them with a scale map of the environment. I usually use a gridded battle mat and dry-erase markers, but 1-inch square graph paper works just as well. I’ve also seen 3D battle maps that look amazing and really give players an immersive experience, but I ain’t got that kind of money.

Props

Having physical props like sketches and descriptions of important items and characters, maps for player reference, or written notes are fun tools for speeding up gameplay and keeping the party’s attention.

Essentials for good preparation

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Often when we prepare a game, we can get lost in telling a story, and creating a world. Sometimes it’s easy to forget crucial considerations to ensure a session can be a fun experience for everyone.

Know your players and their characters

It’s a really good idea to study your players’ character sheets and develop an understanding of what they can do in the game. Powers, abilities, skills and motivations can help you create a fulfilling game experience for everyone.

If you’re building a dungeon based around the idea of casting certain spells in the right order to open doors, you might want to make sure there is a member of the party who can cast spells.

Know the environment

Because Dungeons and Dragons allows imaginative freedom for players, you should be very aware of what the environments you encounter are like. Questions like, “how high is the ceiling” or “how far is this window from the water below” will get asked, it’s only a matter of time. Adding details such as temperature, smell, or even taste help immerse players too.

Getting familiar with the adventure’s layout is also really important. What I mean by that is you should know the major features of the adventure and where they are in relation to each other.

In smaller environments it’s hugely important to know where entrances, exits, and changes in terrain are, because your players will be using them to move around.

Know the story

Some games are deep with lore and rich with story, and others are simpler and straight-forward. Neither of these are right or wrong, but regardless, knowing the story is crucial.

Even if your game is straight forward, your game will run better if you consider how and why your player’s opponents stand in the way, what they’re doing when encountered, and how they’ll react to seeing the party.

If you’re running a game that is heavy with story, a comprehensive understanding of its beginning, middle and end is critical. Take special notes of key events and turning points, and pay special attention to developments happening because of your player’s actions.

Know the opponents

A GM needs to pay close attention to the enemies and obstacles that stand in the way of the players. Why are they there, what are they doing, how will they react, are all questions worth asking.

Not every opponent should act the same way. Animals, for example, usually exist in a space because they live there. They may attack player characters if they’re protecting their territory or their young, if they’re starving and there’s no easier prey, or if they have been bidden to do so by a master.

Most all other creatures of greater intelligence will try to assess their situations before attacking. This could mean a few different things depending on the situation.

Unless they are guards standing at their post, most creatures won’t simply stand around in a room and wait for the party to enter and engage them. Take into consideration an enemy’s powers, natural abilities and weapons. What is their view of intruders? Would they immediately attack a stranger, or would they be willing to negotiate? Would they be caught unawares or would they be expecting intruders, and set up early warning systems?

Something to remember is that creatures with nothing to gain from attacking the party, probably won’t. This doesn’t mean you have to fill your sessions with pacifist encounters, but it does mean you should think about why the opponents are after the players.

Know the rules

Of course, nobody needs to have a perfect working knowledge of all the rules. With Dungeons and Dragons, that’s an extensive amount of knowledge that would be unreasonable for anyone to expect another to memorize.

That said, a good DM should be familiar with the rules that come up quite often during the game. How to attack and defend, how to resolve skill checks, and how to determine combat order are probably the major ones to have down.

When I play as the DM for my D&D group I mark pages in the Player’s Handbook and Dungeon Master’s Guide, so I have a quick reference to rules that may come up but aren’t frequent occurrences.

If any of your player’s characters have abilities that use unusual or complicated rules, it’s worth studying. The same goes for creatures, traps or situations the party might come across.

Don’t go crazy with it

Remember that at the end of this you’re getting ready to play a game with your friends. If you prepare too much, you can end up ruining it, and that would be a shame after all that work, wouldn’t it?

I recommend preparing enough that you’re prepared for situations likely to come up, but not scripting so much that your players feel like they don’t have freedom to make their own decisions.

On the same note, you don’t want to have so many notes that you can’t keep them organized, or that the whole session falls apart if your players don’t do what you expect of them. Trust me, your players will surprise you every session.

Keep a few alternate plans in mind

As I mentioned before, there will come times when your players will do things that you don’t expect. If you don’t have any alternative plans in mind, this could absolutely derail the whole session.

Alternative plans don’t have to be extremely complicated. Allow me to present an example of what I mean.

Let’s say you have an adventure in mind for your players to sail to a tropical island in search of pirate treasure. Perhaps, inspired by Treasure Island, you plan to have the players take their treasure map to the navy and sail honestly for the island. However, your players surprise you and they decide that if they want to keep the treasure, they’ll have to avoid official channels.

At this point, if you planned ahead of time, the players could investigate a seedy pub and strike a deal with pirates. Alternatively, they could convince a trading ship to set sail there as well.

With slight changes, the adventure could be more or less the same as you had planned, but under a different context.

Final Thoughts

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If you keep these points in mind and remember that improvisation will be part of the evening regardless of how much preparation you do, you’re setting yourself up for a successful first game session. Best of luck to you.

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Lucas Taylor

Calgary-based writer just living through one thing after another.