When you are writing an adventure for your Dungeons & Dragons party, there will be fights. This game, at it’s core, is about fighting monsters. That is why 1/3 of the core rulebooks is just monster stats, and why most of the Player’s Handbook is their characters murder-ability. If you want to play without fighting monsters, I’m not going to gatekeep and say that you shouldn’t play D&D, but there are probably other TtRPGs that you are going to enjoy more. Go explore some of those as well.
Anyway, you’re going to be fighting, and it’s possible/probable that it’s going to be monsters you’re fighting. For new players or new Dungeon Masters (DMs), the idea of the fight itself can be exciting on it’s own, as everyone figures out their abilities, initiative order, saving throws, and more. However, once the party gets to about 5th level, sure you keep getting new cool powers and fighting new cool monsters, but standing standing still and hitting each other until someone goes down can become pretty boring, very quickly. So, it’s time to amp up your encounters, and make it interesting again!
Environment
This is the first thing you can begin to look at when mixing up your encounters. A “basic” fight happens on a road, or in a room, that’s big and empty so your players can move around the field like a game of chess. Let’s begin to mix that up.
First, if the fight is happening indoors, is this an empty room? If so, that’s weird. I don’t know of many empty rooms in real life, other than sports arenas, because what’s the point of having a room if you don’t put stuff in it? Does the room have tables that can be turned over for cover? Are there stairs that you can climb on to jump down (onto a chandelier maybe)? Is the room dark, and no one has darkvision, so it’s hard to know where to attack? There are a number of ways to make an indoor fight much more interesting, and a good ol’ tavern brawl is a great place to begin to explore this.
Then, we have fights outside. Instead of a road that is between two sets of trees, are there boulders that take a turn to climb, but then you have advantage on your next attack because of the high ground? Is there a river nearby, and when you fall prone in it you have disadvantage on everything until you manage to get back up? Is it on a cliff, and you can try to drive your enemies back, so they fall off the cliff, and you don’t even need to deal a killing blow? Outside is a varied and chaotic place, who knows what you’ll find.
Lastly, there is the outdoors, but manmade areas to consider. Are there buildings nearby you can run into, bottlenecking your enemies as they chase you in? Are you on a ship, where you can climb the ropes and swing around? Are you and your enemy both on different horse-drawn carriages, and you have to balance, while trying to get a shot off, and directing your carriage to be in a more advantageous position as you race through the woods? So many options! Don’t have fights in open, flat areas anymore. Be interesting!
Time Clock
Next, you can put your encounter on a timer. If the players don’t end the fight in X amount of turns, then the ritual will be complete. The NPC you are trying to save is bleeding out, failing Death Saves, and one of you needs to heal them, which means you have to be defended as well by someone else, until you can get them healed. There’s not a lot of ways to put a timer on a fight, but doing so definitely adds tension, and forces your players to be more creative.
Reinforcements
This goes with the Time Clock above, because your enemy could have reinforcements on the way. Do you need to finish the fight and escape before they show up? Or do you have to stop any of the enemies from reaching a bell, thus alerting their reinforcements to come?
Maybe even, your enemy is smart, and knows that they don’t need to fight to the death in this room, because they can just retreat to the next room, where they have reinforcements that are waiting for you to show up. Once they lose enough hit points, or see their teammates fall, then it only makes sense to retreat, because they are losing this battle, but they might win the next one.
Smart Monsters
A blog that I love to read is called The Monster’s Know What They’re Doing. This is a site dedicated to playing smarter monsters in your D&D game. For example, let’s look at Goblins. In the Monster Manual, Goblins have medium armor class, low hit points, a melee attack, and a ranged attack. A newer GM might run these by putting them in a 2×2 formation, with the front two melee fighting, and the back two ranged fighting, until they all go down quickly. However, The Monster’s Know took a look at their small ability “Nimble Escape” and realized that that ability was put their for a reason. A goblin is going to try their best to start a fight from a hidden position, which gives them advantage, and attack at range. Once they make that attack, their next move will be to move and try to hide again, to get that advantage again. Not only that, but goblins don’t look out for each other, so they aren’t going to stick together. They want to spread out, because if you are looking at one goblin, then the other one can get that hidden position it just ran to. Lastly, if a party member goes down, goblins are more greedy than they are smart. They will run to the body and try to find something to steal from you, which leaves them in the open, and your teammate can run up and hit them when their back is turned.
I highly recommend this site, as it will change the way you think about monsters in your game.
Mixed Type
If you really want to get interesting with your encounters, a great way to do that is to have different kinds of monsters all in the fight, working together.
Let’s stick to goblins for a second. Goblins are a very individualistic monster, who fight together out of necessity. They don’t work together because they are a team, but because you can’t hit them if you’re too busy hitting another goblin. However, they are also very weak, and follow orders by stronger creatures. The Monster Manual tells you that there are Goblin Bosses by putting the stat blocks together, but you have to read the lore to realize that they often work for hobgoblins and bugbears. Hobgoblins are very tactically minded, and will position themselves and the goblins so that you are more likely to get flanked, and even split themselves up so that you can be overwhelmed by attacks coming in different styles, from different directions. There are also hobgoblin captains and warlords, each with their own abilities and styles. Lastly you have the bugbears which are even stronger, but dumber, and so they are great for the front line. Suddenly you have one type of enemy engaged in melee, a weaker, but multitude of enemies peppering you with arrows, and one giving commands in the back. Add in any kind of spellcaster, and your party suddenly needs to make careful decisions about who they need to hit each turn, as opposed to “the one in front of me.”
In order to keep yourself from getting bogged down in the weeds of the fight, it helps to group the types together for initiative. So instead of a different initiative score for each goblin, have all goblins attack together, all bugbears attack together, etc.
Three Way Fight
Let’s say there are multiple types of enemies, but they aren’t working together, and instead are also fighting your enemies. Now everyone is making decisions about who to attack, if you can maneuver yourself so that the person you’re fighting starts fighting someone else, or if you can make a battlefield-truce with one side to attack the other. This can get very hairy very quickly, and is impossible to make sure it’s “balanced” because you don’t know how much is going to be fighting each other vs your party. Also, it can be tricky not to have so much of the fight be you fighting yourself (as the DM) and your players watching you roll dice for 30 minutes before they get a turn again. This is definitely for more advanced DMs, but would be a really cool encounter if done properly.
Kobayashi Maru
Lastly, if you’re not a Star Trek fan, the Kobayashi Maru is a fight that you cannot win. It was intentionally designed for you to lose. This is extremely hard to pull off, because your players got into this game to feel like heroes, and nothing about this is heroic. Never put your players in a situation where they “have” to surrender, because they probably won’t, and blame you for making the fight too hard. The only time I’ve pulled this off, was the party was involved in the sieging of a city, and when the villain won, he was going to go to the next city and do it again, so the leader of the city ordered the party to retreat, to give the next city a warning of what was to come. I think this worked because there was no way that the party alone could have saved this city, and no one blamed them, as they were doing what they could to help a city that wasn’t theirs. In fact, the city that they had to warn was the one that they had a loyalty to, so it was easier for them to retreat.
There are a couple of reasons to run a Kobayashi Maru, and it’s usually to show just how powerful the villain is. Again, be very careful here, because D&D players don’t like to feel like they failed, like they couldn’t win. So as long as they fail forward, fail into a position where they are more likely to win later, that’s the best way to ensure they don’t kill themselves, trying to look like big heroes.
The Nerdd 
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