Image by Bing N. from Pixabay.

How a Great Dungeon Master Can Be Even Greater

The payoff is a more enhanced roleplaying experience for everyone.

John Teehan
Jan 8, 2020 · 8 min read

If you’ve taken the spot at the head of the table and are ready to lead players into an adventure of derring-do and epic feats, then you’re already a great dungeon master.

Whether DMing is your passion or it’s just your turn, you deserve applause for taking on the responsibility of guiding players through grand adventure. Just sitting in that chair already makes you great.

Do you want to be even greater?

Be a storyteller

I have never met a talented dungeon master who also wasn’t a storyteller of one kind or another.

I say, go with your gut and weave a story.

Every mission has to have a motivation. Every villain has a motivation. Likewise, your player characters need motivation.

The most frustrating thing a DM can hear after presenting the party with their mission is one of the players asking, “Why should I care about this and risk almost certain death?”

It’s a fair question. It’s up to you to give them that motivation.

Could the party’s mission mean life or death for one of the party members or a close member of their family?

Could the reason the party needs to explore that temple is that the horrors lurking within have been coming out and killing innocent villagers?

What if the entire party has fallen under a death curse? If they don’t recover the Jewel of Life before sundown, they could all perish.

Why throw that ring into the mountain of fire? To keep it out of the hands of primal evil who would enslave the world should he get hold of it.

Whether you’re working from a homebrew or store-bought adventure, take a look at the overall story and make sure that it’s compelling for your players and, if not, juice it up a bit and make the adventure personal.

The author at work (back when he had hair). Photo by West Warwick Public Library.

Saying yes more than no

The player characters are on the second floor of a warehouse that is very quickly becoming consumed by fire. And they’re surrounded by vampires. The only way out is a single window…if they can get to it.

It’s the rogue’s turn in combat. A wild look in his eyes, the rogue’s player turns to the DM and says, “I raise my hand toward the vampires and make a holy gesture I saw a priest once make and say ‘TURN!’”

The DM slowly replies, “Umm… oh, what the hell. Give me a persuasion roll.”

The rogue rolled a 12. Not nearly enough to reasonably convince anyone the rogue had the turn undead powers of a cleric, but hey…for a few moments we were all on the edge of our seats wondering what would happen next.

I’ve seen a lot of DMs operate over the years. Without a doubt, the most fun ones are those brave souls who, when asked by the players if they can do something, say yes.

Oh, you can see the hesitation. The thought that a carefully planned encounter is about to go off in a wildly unexpected direction can justify that reluctance. But they say yes nonetheless.

It can be risky, but a DM who asks their players to trust them also needs to trust the players.

Yeah, you’ll run into jerks. Those who try to test the DM with outrageous requests. Not everything is going to be a yes, but saying yes more than no is going to up your DM star power.

Incorporating backstory

Get to know your player characters.

This can be before a campaign starts, or as it’s getting off the ground. The earlier the better. Nearly all players create some kind of backstory — some create pages and pages of backstory.

It seems a shame that it often gets ignored once the game gets started.

A good backstory incorporated into a campaign can add levels to the overall narrative and character development.

Was a human orphaned at a very young age and raised by elves or dwarves? What if he wasn’t orphaned after all, but kidnapped? What if one or both of the character’s parents appear somewhere in their travels?

Say a player character was originally a farmer who lost their family to a bandit attack. Was the bandit chief ever caught? Might that bandit reappear either as a flunky for the main villain or, perhaps, lives in abject poverty and is need of mercy from the player character?

Did that wizard attend a famous wizarding school? Isn’t it weird how old classmates keep showing up?

With a little planning or even just some inspired improv, your players can witness their characters experiencing a living world.

Grimm Bros. LLC. Source: Wikimedia Commons

Doing the voices

This is, admittedly, a tough one. Not everyone is comfortable doing voices for different NPCs in an adventure. It can make one feel very self-conscious, and no one likes to risk mockery.

It helps if you have a group of players who are into voices and even acting out interactions. Should that be the case, you owe it to them to at least try it yourself. Give it some time and some practice, and you’ll become less self-conscious and find yourself actually enjoying it.

If your players aren’t the sort to do voices, try it anyway. They could get inspired and, within a few sessions, you could have everyone getting deeper into the roleplay than ever.

Take a look at how some other DMs do voices. No one expects you to be Matt Mercer — at least not right out of the gate, but he’s not a bad DM to look at. Chris Perkins and Jeremy Crawford aren’t bad either. Also, check out Satine Phoenix. All of these folks can be found on YouTube and Twitch.

Image by Christina Wert from Pixabay

Critical successes and failures

Officially, at least in D&D, there are no such things as critical successes or failures on ability checks.

That’s fine. It’s one of the most ignored rules of the game.


Because when Tess the Paladin rolls a 20 on that persuasion roll, she deserves to have that overly-officious town priest hand her the keys to the temple! And when Swash the Rogue critically fumbles that acrobatic check to jump out the window? Well, he makes a funny splat sound when he hits the wall instead.

Now the “official” ruling is there was a reason. 1 in 20 odds isn’t all that bad over the course of a long gaming session and too much of a good (or bad) thing can make players either too eager to try ridiculous feats or too afraid to take any risks at all.

Solution? Confirm those critical rolls.

If it’s a fairly mundane action the player is trying to accomplish such as jumping out a window, a standard critical success or failure is good enough. But what about that rogue’s attempt to turn the undead that was mentioned earlier?

A natural 20 should not be enough. Two natural 20s in a row and hey…vampire problem solved in an unexpected manner that will live on in legend and song.

Two critical fails for that roll?

More vampires. Lots more vampires.

Preparation and more preparation

This can be a tricky one to nail down.

What do I mean by preparation?

Does it mean having plenty of maps and minis on hand? Does it mean having props and visual aids? Does it mean making sure the dry-erase marker works?

It could. But not necessarily.

A good DM doesn’t need to have any of the above to be great. Sure, it helps, but being prepared means being ready and able to take on whatever unexpected turns your players throw at you.

Players are an unpredictable lot. Even when you’re running a fairly linear adventure path, some player is guaranteed to try something you hadn’t anticipated.

You don’t have to wing it entirely. You can prepare for some of the unexpected by knowing the world you’re playing in.

If the players suspect a bandit ambush ahead and decide to flank it through the forest, ask yourself beforehand what else lives in that forest.

Probably owlbears.

Lots and lots of owlbears.

If the players decide to approach the haunted fort by sea instead of the land path you prepared, ask yourself what the weather is like. Are there hidden reefs? Is there a beach at the base of the fort? Maybe there’s a sewage or drainage gate.

Don’t despair if you haven’t completely prepared for the players to sneak into the fort via the sewers. All sorts of nasty challenges live in sewers and it should be pretty easy to select a monster on the fly. Don’t forget that the smell afterward might attract the attention of guards or monsters.

You’re going to have fun embracing the unexpected so long as you familiarize yourself with your world beyond your pre-planned paths.


Little things mean a lot

Address the players by their character names and encourage them to address each other as such.

Paint a word-picture when describing settings and events. This is hard, granted. Start small and use vivid adjectives to describe things.

An old wooden door becomes “a wide oak door banded with rusting iron barely holding the cracked wood together.”

A large table could become “a grand table blanketed with the dust of centuries.”

From there, move on to describing sounds and smells. A musty smell can be described as “smelling of wet dirt and rotting leaves.” A dragon’s roar can become “a mighty bellow that shakes the very ground.”

And so forth.

As you practice, you will find your power to describe scenes will grow

Any good dungeon master can become a great one with just a little extra work. It’ll be worth it. You’ll enjoy the game more, and your players will eagerly look forward to every session.


Thank you for reading. I’d love to share more with you via my Weekly Word Roundup newsletter sent to subscribers every Sunday. It will feature news, productivity tips, life hacks, and links to top stories making the rounds on the Internet. You can unsubscribe at any time!

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John Teehan

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Writer specializing in tech, business, parenting, pop culture, and gaming. Visit for more info and rates. Twitter: @WordsByJohn2


Outstanding stories objectively and diligently selected by 40+ senior editors on ILLUMINATION

John Teehan

Written by

Writer specializing in tech, business, parenting, pop culture, and gaming. Visit for more info and rates. Twitter: @WordsByJohn2


Outstanding stories objectively and diligently selected by 40+ senior editors on ILLUMINATION

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