When each character wants a turn at the same skill check, what do you think you would do most often?

As with everything in D&D, it's rather situational, but off the top of your head, what would be your first instinct when thinking that everyone wants a turn at a skill check.

This is honestly one of the biggest problems at a given D&D table. It’s really very redundant when multiple characters attempt to make checks after each other just because the first person didn’t roll well. The way I handle it is by telling the first character “You think you did a good job at it.”

I established during session 0 that I only allow two players at most to make any given skill check. The exceptions are, obviously, for group checks or occasions when another character's background would warrant a roll.

I use this house rule:

The first character can try, with another character taking the Help action. After that, the same roll is used for anyone who tries again.

Once the roll has been made, any other character that tries uses the same number rolled, but applies their ability modifier. So if the Bard tries to lift a rock, rolls a 13 and has +0 they fail the DC15 check. If the Fighter then tries, then they are also considered to have rolled a 13, but since the fighter has +4 strength their result is 17 and they can lift it.

A new roll is allowed if the characters do something that changes the situation in some way. One time my players were stuck being unable to lift a DC25 stone door, and the Barbarian with +7 athletics had already failed the roll. The Barbarian had a level in Sorcerer, so used Mold Earth to try to shape patterns to use as handholds. That allowed him a second roll, which again he failed. The dwarf cleric then used his mason's tools to improve the handholds further. That allowed an additional roll, which again was failed (and the Help action was being used on each of them). Eventually they figured out another way to improve their chances, reducing the DC and allowing a roll which they managed to make.

I will allow people to make retrospective help actions in these cases. So, for example:

Rogue: "I try to lift the door", rolls poorly.

Barbarian: "I also try to lift the door!"

DM (me): Ok, you can hel pthe Rogue to give them advantage. Rogue, go ahead and roll a second dice!

Rogue: *Rolls poorly, again*

Fighter:"I also assist the rogue!"

DM (Me:) >Rogue<, you try to lift the door, and >Barbarian< sees you struggling and moves to help you, but then the fighter gets involved as well, stepping on your toes and knocking >barbarian< off balance in the tight space, and you fail to lift the door.

Now if they decide to try another way - barbarian lifting and someone else assisting - then I'll allow another go, or if they try different things. If one person "spammed" attempts, I might allow them to succeed but take an exhaustion for doing so (not so relevant on dexterity things like lockpicking). But if 3 people try to perform a task which 3 people cannot fit into, I will make the third person the reason the first two failed, narratively, to dissuade people from such efforts - unless it is in their characters nature to be the likeable idiot of the group!

If it is repeatable, and there is no time pressure:  Sure, let them try again and again. Or you can just allow them to take 20 (as suggested in the DMG). You just narrate that every attempt takes time (or taking 20 takes 10 times as long as a single attempt).

If it is repeatable, but there is time pressure: Now it becomes very important that you clarify how long an attempt takes, and then it's also ok to allow multiple attempts. For example, if in a dungeon your players search a room for hidden treasure, say that every skill check takes 10 minutes of combing the room... If 4 players each take turns searching the room, they spent 40 minutes in that room... and every hour you roll a d6 to determine if a monster wanders in on them and a fight happens.  Then you can leave it up to them to decide whether they will risk spending the time to repeat the skill check. If they insist to all attempt it together (i.e. the 10min for each player happen simultaneously), the Player's Handbook clearly says that you would then ask one player to take charge in the the skill check and let them roll it with advantage, since the others are Helping.

If it is not repeatable:  Then you don't have an issue anyways. One player can try to disarm the trap. If they fail the roll, the trap springs! Unless the trap auto-resets itself, there is no need to try disarming it anymore.

Consequences: I've already listed time as a consequence above, but you can also have other consequences. Maybe your players try to disarm a whirling blade trap. If they fail, they get damage. Sure, you can let them take turns to try to disarm it, but every failure causes damage. It's up to them whether they want to keep risking damage.

Quote from DerManiac >>

If it is repeatable, and there is no time pressure:  Sure, let them try again and again. Or you can just allow them to take 20 (as suggested in the DMG). You just narrate that every attempt takes time (or taking 20 takes 10 times as long as a single attempt).

If it is repeatable, but there is time pressure: Now it becomes very important that you clarify how long an attempt takes, and then it's also ok to allow multiple attempts. For example, if in a dungeon your players search a room for hidden treasure, say that every skill check takes 10 minutes of combing the room... If 4 players each take turns searching the room, they spent 40 minutes in that room... and every hour you roll a d6 to determine if a monster wanders in on them and a fight happens.  Then you can leave it up to them to decide whether they will risk spending the time to repeat the skill check. If they insist to all attempt it together (i.e. the 10min for each player happen simultaneously), the Player's Handbook clearly says that you would then ask one player to take charge in the the skill check and let them roll it with advantage, since the others are Helping.

If it is not repeatable:  Then you don't have an issue anyways. One player can try to disarm the trap. If they fail the roll, the trap springs! Unless the trap auto-resets itself, there is no need to try disarming it anymore.

Consequences: I've already listed time as a consequence above, but you can also have other consequences. Maybe your players try to disarm a whirling blade trap. If they fail, they get damage. Sure, you can let them take turns to try to disarm it, but every failure causes damage. It's up to them whether they want to keep risking damage.

 

 +1 to this

I feel like option 2 is more narratively satisfying because even if it's manufactured, that limitation actually allows for passes and failures, whereas you might as well not ask for a roll if 3-6 people all need to fail it for any negative repercussions to be felt. 

Another way to curtail skill dogpiling is not to habitually put story/mission critical elements behind a roll, but rather, develope adventures with multiple avenues forward that accounts for failure. That way, when your party does fail a roll, they're not going to be afraid of missing out on important content, and know that when they succeed a roll, they've achieved something cool in addition to the story. 

Generally I allow whoever first said to attemp skill check and after that only PCs that have proficiency in that specific skill.

It varies for me.  I usually suggest to the players who should make a skill check.  Also, they are beginning to see, that if you're crap at the skill (our Rogue asking for an Arcana check when the Wizard has rolled a 4) you can roll whatever you want, and STILL get nothing.  I have had the raised eyebrow on a high roll at times, and explain that "You see a bunch of squiggles and swirls faintly etched on the device, and focusing on it, you find you feel queasy and get the beginnings of a headache."  If it's pushed, that headache might give the character disadvantage on Int and Wis checks/saves for a short time.

When it's entirely inappropriate, and someone asks "Can I do an Investigation check" after 2 others, who are usually proficient or at least have solid modifiers, I usually reply "Did I ask you to do a skill check?"  Sometimes the door needs to be slammed.  If you're going to simply let them hammer at it until they get it, why bother with the check in the first place?

I use a number of different systems depending on the situation (the only thing I disallow is dog piling):

In the Now

RAW. In the PHB/Basic Rules  there’s actually rules for group checks: (https://www.dndbeyond.com/sources/basic-rules/using-ability-scores#WorkingTogether)

There Can be Only One.* If my say, everyone wants to try picking the lock, I tell them to decide who will be the one to actually roll the check. They don’t all get to roll, but they do I’ll get to participate by nominating the active roller. And by making the decision there’s, it doesn’t come back on me if it goes pear-shaped. I also employ a house rule that a character can only help with an Ability (Skill) check or Ability Tool check if proficient in that skill or tool.
*That doesn’t apply to situations in which they could each make independent identical checks (not “group checks”), for example, if they are all listening to an NPC and each wants to make an independent Insight checks to see if they each individually believe what that NPC is saying.

Borrowing From the Past

I also use mechanics from older editions (or close enough), but don’t ask me which is from when.

Many Hands, Light Work. I tell them to decide who will make the actual check, and the others roll to lower the DC for that person. (No Helping on top of that though.)

Convince Me (or “BS the DM”). Any PC who wishes to participate can make up to 3 Ability checks, each of which must include a Skill or Tool that PC is proficient with, and the Player must describe each well enough to convince me it applies. Only then do I set a DC for that check. If a player can convince me that ([Tooltip Not Found]) can apply to library research, I’ll allow it. If a player can’t describe how (Investigation) can apply to library research, then that player’s PC cannot investigate the library. The party as a whole must accrue X successes (usually 3-6) before they fit Y failures (usually 3), extra credit is possible.

The hard part for me is that it depends on the problem.

Like... if someone does a Perception check and rolls low... there's no obvious indication of failure, so other characters would have no reason to also do a Perception check, so I don't allow players to make a second check unless they can explain why, without metagaming, their character would want to do a check as well.

If it's a physical task that has an obvious indication of failure... attempting to shove open a door, pick a lock, what have you... in that case I would let someone else make an attempt, but any time constraint gets tighter, and if anyone is looking for them the first attempt will draw attention. If there's no time constraint, it's just a question if one person can get lucky or not.

However, if it's more of a social challenge and a persuasion check fails, I will allow one additional player to make a check, but at a higher DC. I don't know about everyone else, but I sometimes have the problem where a player rolls poorly on Persuasion, and suddenly everyone is just trying to throw Persuasion checks at the problem hoping to just get lucky. That doesn't really make sense to me... unless the players do something to drastically change the playing field (like, offering up something rare or valuable, volunteering for something, etc.), a failed Persuasion check isn't something that can just be worked on by multiple people.

Quote from EricHVela >>

…what would be your first instinct when thinking that everyone wants a turn at a skill check.

Everyone gets a turn, everyone pays the cost (time, resources, danger, as appropriate).

And I roll the encounter dice. :-)

If all six PCs want to try opening the door, then they can. That means up to six lound "thumps" echo throughout the dungeon. 

I run duets, so I don’t really have this problem in my games. :)

 That being said, it really frustrates me when people jump into my skill checks as a player, especially before I roll. Perception or investigation is fine, but if something else is my idea and I’m good at the skill, I want to be the one to do it, at least first. Especially if my character action is what leads to the check.

Depends. Sometimes it is one person that rolls, but I do grant advantage if another person is assisting with the check if they can. I would do this for things like investigation or perception. Knowledge checks I allow anyone interested to roll, but only that one time gets the roll.

Quote from Falwith >>

If you're going to simply let them hammer at it until they get it, why bother with the check in the first place?

This. If it's something they can all get a crack at, let them know up front, and if it's something they can just keep trying at until they succeed, you shouldn't be asking for the check in the first place

I let a player "help" the main player and generally cut it off there. I like the requirement that they should be proficient. I'll have to remember that.

Quote from AntonSirius >>

Quote from Falwith >>

If you're going to simply let them hammer at it until they get it, why bother with the check in the first place?

 

This. If it's something they can all get a crack at, let them know up front, and if it's something they can just keep trying at until they succeed, you shouldn't be asking for the check in the first place

 That's another good point... it can be hard to resist, because rolling dice is fun and is kind of the point of the game, but not everything needs to be rolled for.

I have chits (pre-written notes with respect to story scene) and sticky notes for scenes that could possible demand a check.

For example 5 players examine a destroyed bridge, there is acidic, tar residue. They all roll: anyone rolling 14 or over on history check will get a note that their character only knows about and they have to share their knowledge/recollection. They would read, to themselves when receiving chit, "You recognize this acidic residue - a copper dragon, possible responsible for this carnage and destruction."

If it's an attempt for a particular skill, first they need to have the ability for an attempt can be made at all - for example - using their body weight to crush locked door open - typically anyone with a Strength 11 or less wouldn't be allowed to attempt. But anyone with Strength greater than 11 could (each player)....DC starting at 18, substracting 1 on DC per strength above 12.

Or say they wanted to lift a bolder the size of a small yoga ball that weighted 200 pounds, none could try unless their they had a strength of 15 or greater. DC starting at 18, substracting 2 on DC per strength above 15

Here are some guidelines for the examples above:

I usually limit rolls to PCs that have proficiency in the skill. Not for things like Athletics but knowledge skills like Religion or History.

That alone will limit the number of people able to roll. Then if two or more PCs have the skill, they can choose who will roll and do it at advantage.