Making Combat Meaningful

TLDR; I discourage players from just attacking and encourage them to say what their goal in fighting is, so combat is handled like a multi stage puzzle/trap where the various mechanisms are ever in a transient state of being revealed and dissolving.

if my battles don't feel like this i'm failing

 I don't like long drawn out conversations with NPCs. My players rarely go very deep and the times they do I'm often caught off-guard. I do my best world-building secretly, behind a curtain, pouring over old maps and working out complicated historical battles. Don't get me wrong, I enjoy my NPCs, but often I think that might be the problem. We only have so many hours to play this game and I know if I let myself go the whole session could become a conversation with one interesting dude who wears a mushroom for a hat, has a fu-man-chu mustache and rides a sapphire lizard.

The players aren't here for that, and I don't like to encourage that kind of play. If you want to have a game that goes deep into lore come smoke cigarettes with me on the porch and play 'draw the map and talk'. This game is about wresting jewels from fiends in subterranean cesspits and making damning deals with petty gods that might actually be some kind of trans-dimensional AI housed in a quivering hunk of meat.

So instead we act out the first bit of the convo, where I introduce the NPC and say what's memorable about them. Then I cut to the point and describe the gist of what's going on in omniscient narrator style. If the players do something cool or interesting I might jump back to first person and act it out, but mostly I want to get to what the game is really about.

A big way that I do this is with combat. I want to invoke a particular style with my combat. You know in old science-fantasy novels, Vance does this a lot but also in the battle at the end of Dune, when the fighting-men come in and just kill guys? They leap up with their swords and blasters and there's three options 1. die, 2. miss, 3. mortally wound. The author starts you out with fifteen fleshed out heroes and kills ten of them by the middle of the book. The heroes generally get one free miss before they are cut down.

So combat is fast, hard, and gritty. I don't waste time on flowery descriptions. I ask what my players are doing and encourage them to make tactical decisions and plan amongst themselves. The monsters are smart -- they're planning too. I play them nearly as smart as I would play my very own PC. I try to gauge how smart the players are and aim just short of that. Of course, it depends on the monster. Ogres are going to hide and jump out to throw big rocks. Goblins are going to skulk, flank, shoot poisoned arrows, and flee at the first sign of trouble. Orcs blitzkrieg suddenly, creating chaos, using hit-and-run tactics, and are most likely to ambush with burning oil and use prisoners as shields. Skeletons hang back and throw stones, and if the players charge they run out of sight and wait to ambush. Zombies march tight formation and fight like a steam-roller of flailing limbs, focusing on grappling armored opponents.

Combat is deadly, monsters are smart. They look for the weak link and strike there. 

But they're also living things themselves. If they see you first they'll hide or get to higher ground. They take pot-shots from a safe distance. They build barricades or set ambushes. If it looks like they can't win in a couple rounds they beat a fighting retreat and re-group.

My player's aren't advanced. Most of them have never played D&D before. I give them lots of warnings upfront to think about the game world as being real--what would you really do. This often has the effect of making them scared. They do what they'd really do. So I usually send some hirelings along to harass and ridicule them when they're being pansies. Nothing gets the players motivated than a potential mutiny four days from civilization. Suddenly they all turn into dictators. So that's how that happens.

Combat almost never lasts more than three or four rounds because things are always moving. Each round is a pick or push "the monsters are doing this what are you going to do to stop them?"

They're moving to flank you guys, they have bows. You see more coming around the corner.

The wizard starts casting a spell. The magic-user says he thinks it's a fireball. His warriors move into phalanx position, there's no clear shot.

The troll grabs the hobbit and hoists him up into the air. He moves to shove the hobbit into his mouth where he'll start taking automatic damage if you don't stop it.

the orcs are chasing you, hurling spears. The attacks are at a -2 because of the chaos, they all miss, but it's pushing you towards the ledge--in a moment you'll be driven into a corner if you don't think fast.

The wizard launches his fireball--into the pillar, knocking it clean down. The room starts to rumble, bricks are falling from the ceiling. They'll start to fall on you guys next round if you don't figure out how to protect yourselves.

I encourage the players to push back. They talk amongst themselves and come up with a loose plan, or some of them go rogue and start acting on their own. 

I clarify with them and state repercussions: "so you guys are moving back, trying to hide behind the pillars, the fighters are trying to draw attention to themselves -- okay it works, the goblins are going for the fighters with their daggers drawn, the melee will be met next round but it's eight goblins against two, what now?"

But I give them a chance to change their decision once they start to see what might happen:

thief: "I want to run to help him"
me: "Okay so you run over to him and start lifting him up, but he's wearing platemail so he's heavy. The troll sees you and he's there in a bound, lifting his club to strike"
thief: "wait, shit i forgot--I thought I'd just be able to drag him away, I want to run to the door instead"
me: "Okay, so you wanna leave the fighter there and run away like a coward, well the troll sees him and lumbers over"
thief: "shit, sorry dude!"
fighter: "I hate you."

I warn the players when they put themselves in danger. When they come up with a plan, I tell them what might go wrong, or what the monsters will see, or what they're thinking. If they say they want to do something, and doing it won't really change anything, I just say they do it and tell them nothing changes. Or I push back.

team: "we want to try and run up and scare the ogre to see if he'll topple off the cliff"
me: "you all run up screaming, waving your swords. the ogre looks down. he smiles. you can taste his breath. he's not scared at all."
team: "we should run away."
me: "you run. he chases you. he's much faster. you can either make it to the bridge or duck off down the corridor. what now?"
thief:"let's go to the door."
fighter:"no, go across the bridge. I'll cut the ropes and try to swing across."
mage: "you're a fucking idiot"
me:"you can do it fighter, but you'll have to make a saving throw vs paralysis to see if you survive"
fighter:"fuck it, i'm doing it, i only have 1 hp anyway"
thief:"if you die i'm building a statue in town for you. if you live i'm going to shit on your chest while you're asleep"
fighter: "yeehaw! bitches! I rolled a 17!"

and I don't pull punches. We use d6s for health and hits. I roll damage and attacks in the open, where the player's know it's not me. That means you can take maybe one hit per HD. You feelin' lucky punk?

dm: "you're surrounded by bandits with crossbows. the bandit leader has the wiseman around the neck. he says 'give us the gold!'. Honestly, if you can't think a good way out of this you're probably fucked"
fighter:"I tell the bandit leader no fuck you and I try to cut his head off"
dm: "are you sure? you've got like a dozen crossbows pointed at you. you could try something else."
thief: "dude, what are you doing."
fighter: "no fuck him, he's a asshole. I stab his face."
dm: "throw your attack then"
fighter: "4 I miss"
dm: "he parries your blade easily. the bandits all fire the crossbows you knew they were pointing at your face. That's twelve attacks." *clatter* "you get hit six times for 23 damage"
fighter: "avenge me!"
mage: "fuck that we run"
thief: "can i steal his magic sword before we go?"
dm: "if you're willing to risk three of the crossbowers getting free shots at you."
thief: "nevermind."

The question is what are you willing to risk?

We don't show up to the table to throw dice. How many games have you done this?:
*clatter* a miss
*clatter* a miss
*clatter* a miss
*clatter* you hit
*clatter* one damage

Fuck that. If nothing is happening, why are we rolling? When you miss, you fail. Something changes. The attack doesn't just miss, it fails. You lose something. The enemy advances, or re-positions, or you put yourself in a bad position. Another element is added to the combat. It isn't about tracking squares on a game-board, it's about tracking an ever unfolding situation.

On the other hand if the players come out with a great plan, act confidently, make it fun, or do something interesting or unexpected, they gain the advantage. If they surprise me, the world itself it surprised. If the players fight smart I'll force the monsters to make a morale check even if there haven't been casualties. The monsters can tell when they're outmatched. They don't want to fight--they want and EASY target. The sick, small, and old antelope are the ones that get eaten. Most monsters are merely territorial. They'll fight to defend their thing, but they'd rather run away and save their own skins. This is especially true with chaotic monsters, like orcs and ogres. Lawful monsters like hobgoblins are more likely to stay on account of social conduct and expectations. Monsters are even worse than the worst parts of humanity. They're cruel and clever but stupid and mean and selfish and greedy. Selfish first, greedy second, clever third, and cruel when they have the edge.

dm: "the goblines come up, they've got their hands raised, one is waving a white flag"
thief: "i throw the camphene bomb."
fighter: "hell yeah"
cleric: "they're surrendering."
fighter: "i shoot my crossbow."
dm: "you guys are attacking?"
cleric: "this is fucked up."
mage: "I throw my dagger."
me: "okay, they totally weren't expecting this. Roll against AC 9"
*dice are resolved, most of the attacks hit*
me: "ok, you murderate the fuck out of the goblins. they're all dead. do you search the bodies?"
fighter: "yeah, i want my money back"
me: "you find they're armed with poisoned daggers. they were going to trick you and stab you in the back when they had the chance."
fighter: "an ambush!"
cleric: "good job guys."
thief: "no thanks to you."

If it all fails, let the dice fall. If they choose not to heed your warnings, they suffer the consequences. You told them the danger. You even offered alternatives. "swinging on the vine is super dangerous, the other option is to slide down the hill into the water, but that might slow you down." You were up-front and worked with them. Sometimes their plans work out. Sometimes they die horribly.

If your combats are long and drawn out, try implementing some ideas here. That's why you're a REFEREE. You're fair-ish, sort of impartial, and mostly chaotic neutral. The more you act as the eyes and ears and common sense of the players, however twisted, blind, and stupid they are, the meaner and more vicious the world can be in return. If the players have a good idea about their odds, what exactly the risk is, they can make worse decisions. Try to make every single one of those decisions count. Encourage that behavior. Because the payout is worth it.