Designing Your Dungeons & Dragons Encounters with James Gifford

d&d Sep 14, 2018

James Gifford, author and illustrator of Dungeon Diaries, returns to improve your Dungeons and Dragons encounters (also applicable to any tabletop roleplaying game PATHFINDER FOR LIFE! – Ed: Robin)


Back when I was a baby goblin, I used to play Dungeon Crawler game like Torchlight and Dungeon Siege. I remember thinking they were the best thing ever until I revisited them years later. Facing wave upon wave of monsters, even different varieties, felt more like a dull daytime job.

D&D should never feel like this. Meeting up as a group is hard enough, wasting precious DnD time with ‘random’ encounters rolled from a list gets old real fast. So here are some tips on how to make those encounters more dynamic and meaningful:


Encounter Exposition

The first thing I usually think about when designing Dungeons & Dragons encounters is: Why are there enemies here? What are their motives and morale? How does this contribute to the overall story? Don’t waste precious DnD time by making encounters of ‘fight-to-the-death’ monsters just to fill a dungeon. Use those battles to enhance the narrative of the adventure.

‘Show, don’t tell’ how the monsters react when in a losing battle. Use the encounter to reflect how the campaign’s unfolding events have affected the wider world. The more you can tie your enemies and monsters into the action of the plot, the more rewarding those Dungeons & Dragons encounters will be, especially to players who like to roleplay. Here are some examples:

  • For villain-based adventures, the adversary is constantly showing up in a string of different encounters, each time showing a new low to his wicked depravity…before escaping like a worm, deeper into his lair.
  • The players encounter a fight between two rival kingdoms, one side losing terribly, begging for help and mercy…only to find they are bandits and criminals.
  • The Ogre stumbling through the forest ahead is blinded by a strange disease, or twisted by that magical phenomena the locals were talking about?

Build up anticipation with a breadcrumb trail of trivia.


Encounter Objectives

The second important thing a Dungeon Master should consider is the immediate objective of the Dungeons & Dragons encounters. Treat it like a mini-quest or puzzle. Think beyond the “Just hack it till they’re dead” strategy. Here’s some examples of encounters where the objective at least differs slightly:

  • The Undead are heading towards three different NPC’s far from each other, either split up or choose who to rescue. You have 1 minute to discuss strategy.
  • You are without your weapons at a noble’s party. Defeat/subdue the assassin using the surrounding décor as improvised weapons.
  • Local villagers who you are charged to protect are brainwashed into bloodthirsty monsters. Restrain them, but don’t kill them.
  • You’ve surprised a band of Orcs outside their fortified camp. Chase them down before they get through the gates… and to their ballistas!
  • The trapped chamber is filling with water; the exit key is inside the Golem’s open chest. You have 3 rounds before you’re totally submerged. 4 rounds before the electrical trap is sprung…
  • The summoning ritual will only last so long, hold off the imps and interrogate the demon lord before he vanishes.
  • The fire in the wizard’s scroll archive is spreading. Put out the flames before the loot is destroyed…The fire elemental creates thick fog when doused with water.


These are cases of ‘Only this kind of damage is works/is effective’, ‘Get to this area’, ‘get that thing’. Adding these optional objectives encourages the players to strategize.

Also adding a timed objective ups the tension. Not every encounter needs to be life threatening, at least, threatening to the characters. Timed objectives to obtain perishable treasures, NPC’s with information or attempts to change the plot’s direction are all things worth fighting for… buuuuut, also no BIG loss if they fail. As your player’s watch that Staff of Power and the entire royal family tumble into the demonic void, they can at least be glad that they’re alive. Hey, you win some, you lose some – and that’s the fun of it!



Lets suppose you’re jumping into an unprepared combat encounter and haven’t got anything else planned. Random levels of height and cover provide an easy on-the-fly way to add variation to each fight. A steep hill or cliff, fallen trees, a ruined outlook, trenches, boxes and barrels, large boulders – these are all obstacles that the players can consider traversing to gain height advantage, or defense. A good ol’ tree, rock, or ruined structure is an easy throw-in as they don’t need a lot of context as to ‘why’ it is there. 

Malicious enemies might wait in ambush in areas where they have the terrain advantage: Bandits above a narrow impasse, Harpies roosting up a cliff, Sahuagin’s hiding amongst the coral reef…even ambush under the cover of darkness…


Interactive Elements

These take a little more planning, but give the players…or the enemies…the tools to liven up the encounter. Often part of the dungeon or environment, they aid/hinder movement, damage, protection…etc. Have a look at spells and see what weird effects you can attach to set pieces. Many video games will design entire areas based around one of these ‘game mechanics’. Some examples:

  • A magical Orb with a persistent radius effect, e.g. Shield, Darkness, weakness, healing, raise undead…Perhaps with a few successful ‘Arcana Knowledge’ checks, the wizard can learn how to turn it against his adversary?
  • Levers that activate the dangerous machinery, lifts, and traps around the room…the labels of which are written in Goblin only, of course.
  • A Strange Fungi that is incredibly bouncy, allowing access to higher areas.
  • Natural cave crystals that burst with blinding light / Fire / sound when struck. The bigger the Crystal, the greater the effect.
  • Useful items e.g. A sack full of spiked caltrops, A half-forged flaming sword (cursed), experimental alchemical potion – bombs with random effects, An old siege crossbow mounted on the ruin’s parapet.
  • Fire braziers…and…are those barrels of oil?

Without the right context, a lot of these might seem a bit too ‘convenient’. Only the dumbest of goblins leave barrels of Oil unguarded near open flames…ask yourself, ‘why is this here? Is it out of place?’. Keep it simple and don’t add too many interactive elements at once in your Dungeons & Dragons encounters.


Difficult Terrain/Hazards

As any long-dead army general will tell you, weather effects and terrain can make or break a battle’s outcome. If you’re just throwing in marshy water to reduce movement speed, you’re being lazy. If this is you, slap yourself now and take 1d4 non-lethal damage.

Some areas of marshes are deep enough to sink in entirely. There are areas of flammable natural gasses, fog, rocks, poisonous spores and hallucinogenic mushrooms, and Gods help you if you’re wading in wearing heavy armour…

Bad weather and conditions can spoil provisions, attract disease and fatigue. Raging heat or bone-rattling cold can break even the strongest of resolves. Exaggerate these dangers. If the player’s aren’t quaking at the thought of being caught in a thunderstorm at sea, you’ve gone wrong. Consider what hazards can be found when:

  • Climbing sand-dunes
  • Traversing giant moving cogs
  • Scaling a cliff face
  • Swimming through a coral reef
  • Navigating a tight crawl-space
  • On the deck of a rocking ship
  • Flying through a turbulent storm.
  • Running through a crowded street

Watch some survival and nature documentaries. The creatures that live in these hostile environments have all manner of crazy defense mechanisms and hunting tactics that will give you monster ideas.

And these are my go-to tips for enhancing encounters in Dungeons and Dragons and I’ve had many a fun time experimenting with Dungeons & Dragons encounters and subjecting players to all manner of surprises!



James Gifford – Creator of  Dungeon Diaries. Buy a copy for yourself or check out James Gifford Illustration

Follow James on Twitter – @MrJamesGifford or join his  Facebook Adventuring Party for more D&D, coaching, and geekery!


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