Whenever you tell a hireling to do anything monotonous, dangerous, or work perceived to be below them; roll under their Loyalty with a d20. If you tell them to do something really dangerous or suicidal, roll with disadvantage. If your group is attacked, then your Hireling will fight in your defense without needing a roll, but picking a fight or making the hireling go above and beyond will require a roll. Whenever you fail the roll, the hireling either refuses or stews on it and loses -1 Loyalty permanently. You might be able to increase loyalty by bribes or if they grow in power.
These rules aren't exactly new. If you want to make them less swingy; calculate the “Loyalty Modifier” of the Hireling instead using your favorite stat array and roll a 2d6 + Loyalty Mod + Commanding Character's Cha Modifier and get a 7 or better to do anything dangerous. Maybe snake eyes on this roll loses -1 Loyalty score permanently.
Whenever you are separated from your Hirelings, or if the Hirelings are instructed to stay behind or guard a location; the Hireling with the highest Charisma has their Loyalty score used for the group; They act as the ringleader. If you seek a more random method to determine the Ringleader; instead have each major Hireling character roll a 1d10 + their Charisma mod and add a bonus +1 or +2 if they are higher level then the other characters. Hirelings who act as Ringleader will command other Hirelings and retainers to perform whatever task was given, or to follow their own path.
If the Hireling was instructed to be left alone to guard something or stay behind, successful Loyalty check means they carried out what they were told to do. Failure means rolling on the relevant table, or simply having the Hirelings make a fatal mistake. Save vs death.
If the Hireling was accidentally separated, such as by a shifting wall or monster ambush, successful Loyalty check means they will attempt to reconnect at the earliest possible opportunity. Failure will mean they assume their leader is dead or lost control of the mission, and the ringleader will take command of their own squad of people to fulfill their own goals. Next time they meet, roll a reaction check using the Hireling's Loyalty roll to see if they seek to return to your group or have permanently decided to leave. Each Hireling gets a Loyalty check to the original party to see if they also abscond, but will get a negative to this roll equal to the Ringleader's Charisma mod.
Roll on the most relevant table. If there is no relevant table, or to roll for a totally random result of Hireling incompetence, roll 1d6 to determine the table and 1d6 again on the table for the result. Low rolls are generally worse results then higher rolls. Exceptionally trustworthy or competent Hirelings may prompt a 1d6+1 roll and ignoring the accident on a roll of 7.
- Guard Duty / Military Force
- Menial Labor
- Holding Captured Prisoners or Monsters
- Ferrying Things to Camp / Carrying Supplies
- Preparing Potions or Spells / Working in the MU's Magical Laboratory
- General Mischief
-Guard Duty- For when Hirelings stay up late to watch camp, watch the dungeon entrance, or otherwise perform any duty relying on watching and fighting off any intruders.
 The Ringleader is dead. All of the Hirelings get a save vs death modified by Con to see which ones are badly injured but still alive; if they fail the roll, they're dead too. Roll a wandering monster for this area; this is the thing that killed them all. The monster is long since fled, but leaves tracks or clues.
 The Ringleader accepted a bribe from a rival adventuring group or intelligent monsters. These beings entered the area or were given information. They deny seeing anyone but have found a fat sack of silver that they refuse to share or talk about.
 Asleep. The Ringleader was on the last shift, and is now fast asleep. They'll claim the enchantment was a magical one wrought by a spell. Roll on the monster table for this dungeon and only if that monster can cast Sleep is their story true. In the meantime, at least one group moved through the weakness to steal something or enter the restricted area.
 Drunk. The Ringleader either broke into your wine stash or brought along ale secretly. They and several other Hirelings and retainers are getting drunk and being useless. 2 in 6 chance something sneaked past them, 1 in 6 chance they lose something important to the expedition.
 Noise. They are sharpening weapons; the loud droning noise of working iron and steel draws nearby enemies. Or they are partying and laughing, or doing anything that makes too much noise and attracts attention. roll a wandering monster check. These are encountered when the party returns.
 When you return, they demand higher pay for long hours of boredom. You can also shut them up with a hearty meal and ale, or a simple magical trinket.
-Menial Labor- For when Hirelings are digging through rubble or building bridges and barricades.
 They've unleashed something. The Ringleader ordered the group to disturb a burial site, the sound attracted a monster, etc. The monster is busy killing the Hirelings and retainers when you encounter them all again. Roll initiative.
 Workplace injury! Hireling with the lowest Strength score is impaled on a piece of wood or trapped under a pile of rubble. The Ringleader is responsible for it. The injured character requires immediate medical attention or they die.
 All their tools are broken. They've hit a rough patch of dirt, or the sarcophagus lid was much more stuck then anticipated. You'll need to replace them, which will be expensive. Ringleader either egged on the other Hirelings or is the one responsible for breaking it for singular important tools.
 Fatal flaw. Something about their work or effort has a glaring flaw, the Ringleader let them use a shortcut. It can be used but has a saving throw associated with it. The barricade can be climbed over by an agile opponent, the trench will flood if a rainstorm comes, the rocks can landslide unsafely, etc.
 Grumbling. The Hirelings and retainers lose -1 point of morale for the rest of this trip, spurred on by the Ringleader's complaints. They joined the party for easy loot and big payouts, not “honest” work, if they wanted that they would have stayed home!
 Ragged and exhausted; the job is done by the Hirelings are overly tired out. They have disadvantage on rolls and other negatives, they need a day's rest for their fatigue.
-Holding Prisoners- For Hirelings watching over your captured humanoids or if you're punishing another Hireling for whatever reason. Also includes non intelligent monsters held down by chains or in cages, ready to be shipped back to civilization for sale.
 Escaped. Corpses nearby the busted cage; 1d4 of the lower paid retainers or camp followers are dead. Ringleader returns from some 'me' time in the bushes, not having any idea what happened.
 Freed. Someone has freed the beast- the Ringleader is the one with the most knowledge on what has happened and who it was. They let it go while nobody was looking, and it killed or destroyed nobody, but is now gone and left few traces.
 Property damage. The beast didn't escape, but the prisoners took their time to ruin something in the camp. Maybe they managed to reach their hand through the bars to grab a key and sit on it, or during a failed escape attempt the monster trampled a bunch of tents and suits of armor. Roll X in 6 to see if you lose anything actually important; X is the value of the prisoner's HD.
 The arm or leg of the Ringleader is caught in the beast's jaw! When you return, you'll have one action to try and prevent the Hireling from losing their limb. You could try to avoid this by offering food, or freeing the beast. For intelligent creatures in your captivity, it may just be a shiv to the back or throat instead, demanding freedom.
 Poor Morale. The beast is whining or the prisoner is begging for freedom. Even if it's a manipulative trick, your Hirelings and the Ringleader are considering letting it go. They will take a hit of -1 morale unless you can prove the prisoner's spitefulness or they are released.
 Feeding time. The imprisoned beast or prisoner has been eating an absolute ton of food. The Ringleader is responsible, perhaps trying to keep the beast tame. You lose 2d6 rations or drinks of alcohol for a intelligent prisoner. The prisoner is sleeping off their food or drunken stupor peacefully.
-Carrying Things- When carrying back loot back to camp or town, OR when carrying supplies to a dungeon or onto the party's ship for an expedition. Ringleader is either first in line or carrying something specific, the reason or this listed below.
 Carrying something shiny, good smelling, or otherwise attractive to monsters. Huge flying beast swoops down or subterranean creature digs up, kidnaps Hireling and what they were carrying.
 Theft. Ringleader was either the theft or encouraged theft; either several worthwhile supplies like alcohol go missing, or a single valuable treasure they were entrusted with goes “missing”.
 Stowaways. Annoying parasite, insect, barnacle, gremlin, or other creature that has snuck into your camp or town. It will be a constant annoyance, up to destroying gear, the party being blamed for the impending infestation of the pest, or even the loss of stats or damage from diseases brought on by the vermin.
 Stowaways. Hiding in the cargo boxes, food bags, wagons, or other places ended up being a young urchin obsessed with adventure. The youth is bright and energetic, but very likely to get herself killed.
 Damage. Some of your common items were damaged. Rations accidentally went bad, bandages dropped in the mud making them dirty and useless, torches thrown on campfire by mistake, etc. These only apply to basic supply items; you lose 75% of a single category of useful tool (most of your rope, most of your light sources, etc.) or 50% of three categories. (Lose half your rations, half your repair kits, half your bedrolls).
 Tripped. Ringleader has fallen and sprained their ankle. They won't be able to walk for the rest of the adventure, and will be useless in combat.
-Preparing Potions/Spells- For whenever the Hirelings are working in the Wizard's laboratory, translating magic books, brewing potions, or otherwise doing mystic stuff. In this instance, use the Intelligence of a Hireling to break ties between the most Charismatic ones.
 Chaos. The magic energies have gone loose! Random elemental explosions scorch, freeze, or electrocute 1d6 Hirelings and camp followers to death, and 1d6 HD worth of otherworldly creatures now ravage the campsite- summoned by mistake.
 Dud. Too much mundanity was mixed in with the latest potion, wand, or scroll. The Ringleader covered up the failure and passed it off as a working magical item. Just when you need to sip a healing potion, it tastes like fruit juice and fails. When you flick your wand to conjure an attack, it fizzles like a sparkler; becoming useless.
 Possession. Somebody got possessed by a demon, ghost, or otherworldly spirit attracted by the arcane and did not follow proper preparations. This is a secret result, nobody will know at first about the possessed person. The Ringleader is possessed, and will use a combination of their standing and natural abilities to try and influence the party to give it more power and feed its unholy desires to sacrifice virgins to its master from beyond the veil.
 Noisy Spirits. Nearby elemental spirits have been awakened by mistake, are now being quiet noisy and arguing with each other. The rock wall you are camping under starts to grovel about the smoke from the fire you started, which is cursing at the wind for constantly trying to put it out, and so on. The spirits may come to blows on a 1 in 6 chance, causing them to act spontaneously; rocks move on their own, sand swallows the cart, etc. This will be local minor catastrophe if it happens. The noise may also attract attention even if you calm them down, forcing a reaction check roll.
 Wild magic. The Ringleader was unfortunate enough to be mutated by an errant surge of wild magical energies. Roll on your favorite mutation table for them- roll a save vs spells. On a failure, the mutation is permanent. Otherwise, it lasts 1d4 days.
 Minor Curse. One random Hireling is hit with a surge of strange magic. The first character to inspect and/or touch them is cursed with bad luck. For the rest of the adventure, treat all rolls of 20 as a 1 instead. If nobody touches the affected person, the Ringleader will contract the curse instead.
-General Mischief- Roll whenever the Hirelings are left alone for a while, giving boring work after already getting tired of it from the Labor or Guard Duty table, or are otherwise distracted and not given much supervision.
 Fatal Accident. Random Hireling with the lowest Con has died from a game or job taken too far. Sparring got too rough, somebody slipped off the ravine, etc. Ringleader had something to do with it, either was the guilty party or is covering for them.
 Idiotic Effigy. Ringleader builds a religious symbol, uses several piles of treasure they were guarding to decorate it. If they are a Cleric, it is to that God. If they are not, then it is too a random God or elder beast. The Ringleader has swayed 2d6 Camp followers to their faith, but each Hireling is a little more resistant and only joins if it makes sense for them too. They will refuse to tear down the effigy and will start to act as a leader.
 Gambling. Ringleader has constructed a illicit gambling operation, is almost certainly cheating. They quickly stealing money from other Hirelings and camp followers; and have gained 1d10x5% of the way to their next level in experience points in value. However, the others are beginning to demand you expel the Hireling or force them to give their money back, grumbling saps morale if not appeased at -1 Loyalty to all characters who were affected. Hirelings with an Int of at least 15 do not buy into the scheme and don't require appeasement.
 Fire. Cooking fire got out of hand, or an idiotic pyromaniac got let loose. Ringleader is trying to organize a defense, poorly. Property is burned; 1d8 tents destroyed and 1d4 mounts break free and ran off in fear of the blaze.
 Rumors. Several bad rumors have come up regarding the player characters, with the Ringleader secretly being the one to start or spread them. Unless these rumors are addressed directly, there is a chance they'll lower the level of respect. 1 in 4 chance for a serious rumor to reduce Loyalty by -1.
 Drama. Hirelings and camp followers are arguing with each other over petty nonsense, chores being ignored, improper split of loot and so on. The Ringleader will instigate a conflict, two random Hirelings will come to blows over it. Both characters take 1d6 damage from punches and kicks unless restrained and some bruised pride.