Player: Damn .... 3 .... OK, next turn I'm going to ....
Or this
Player #1: I'm going to search for traps
DM: Give me a skill roll
Player #1: Damn .... 3 ....
Player #2: I want to look for traps as well!
Player #3: Me too!
Sometimes the player just isn't supposed to know how well the character is really doing. The character might think they did OK, and be wrong ( evil DM cackle ).
Sure the DM can make such rolls for the Player - but the Player might get cranky if you roll badly for them.
I'm thinking about using a quick "lookup matrix" - as below - for this kind of roll. The player would make a D6 and a D20 roll together for a skill roll. D6 is the column, D20 is the skill roll.
Player: I'm going to use my bonus action to hide
DM: Give me a masked stealth roll
Player: Um ... 5 & 19 ... ?
DM: What's your bonus?
Player: +4
DM (jotting down 8): OK, you duck behind the scrub brushes, and freeze in place.
The D6 roll wouldn't strictly be needed, but if there was only one randomly shuffled columns, then players would start to notice "11 is good, 16 is bad" pretty quickly.
The DM can either do the math for the bonus ... or you could even make a stack of different matrices ( +1 matrix with values 2 through 21, +2 matrix with values 3 through 22, etc.), or even do it "live" in a spreadsheet.
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The stealth roll isn't a problem in combat. The player's character should be able to tell that someone's spotted them; the feedback is immediate. The real problem with Stealth happens out of combat, because you roll for it up front when you start traveling, so if you roll a 3 you know you're going to get caught as soon as you come across a monster. I solve this by rolling secretly for every player when they start moving.
The "search for traps" scenario can be solved easily by changing how you're handling the ability checks. Search is an action you can take in combat, so it's possible roll a Perception check and find a hidden creature, object or trap in 1 round. There's also no consequences for failing; they can try again next round. The same should hold true out of combat.
Ask them to be specific about where they're looking ("under the rug", "in the desk drawers", etc) and take the DMG's advice on repeated checks: if it's possible for them to succeed, they do so after x10 the duration of a single attempt (so, 1 minute). If multiple players want to search, you can divide the time if they're searching in the same place or they can split up the room. If they're searching walls or floor for pressure plates/hidden doors, each 5 foot square takes 1 minute. If they're in a dungeon, they're not going to want to spend an hour per room or they risk having more random encounters.
A couple of counter-points ( by which I mean I'm not arguing against you, I'm just batting the ideas around to see how they hold up, and where things land :) )
I did acknowledge you can roll for the players; but not everyone is happy with that, especially when you screw up on their behalf. Personally, I like the players making as many rolls as possible. That way they can't blame their screw-ups on me :p I know that "random is random", so it doesn't matter who rolls, but they seem happier having their fate in their hands ( apparently ).
Akin to the "take x10 the time" rule, I would say if there's no consequence for failing a skill roll outside of combat, there's no point in making them roll over and over - they will keep rolling until they "get it right".
It's simpler to adopt a "degree of failure" rule based on a single check: E.g. they needed a 12 to pick the lock, they rolled an 8, it will take them 4 x <some unit of base time> to get the lock open. You might ask them, "How long are you going to keep at it?", and if they say they're going to give up after 5 minutes, and you have determined it's going to take 11 minutes for them to puzzle the lock out, then they don't succeed.
It's still a single die roll.
In combat, or some other time pressure ( can they get the hatch open before the water level in the room gets too high? ), absolutely keep making individual rolls going each round. That has dramatic tension.
Additionally, making the players detail each and every place they search, and rolling multiple times for searches seems tedious. I have a tendency to give the players "the benefit of the doubt" - if they're searching, their characters are experienced enough to conduct a thorough search; again, a single roll.
Adopting your example, I might ask how long they're searching, and where each of the players are searching, and again, they make a single roll each.
However,
The problem isn't with multiple players searching, or trying to gain Insight on an NPC, etc. - it's the meta-gaming of players making choices for their characters because they know that someone else failed a roll, when they wouldn't have otherwise acted if they didn't know - and there's no way the character would know.
The only way I see to prevent that is to take away that knowledge.
Either you make the roll for them - which appear to be the standard response, but takes away some of the player agency IMHO - or make their roll not obviously be a success/failure when they wouldn't know if was a success/failure; this idea is a crack at doing the latter.
In your case of combat hiding, then yes - a "normal" skill check would make the most sense. In hiding from the patrol - they wouldn't know right away.
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Unless there's a benefit and a consequence to a roll, there's no real risk-reward to the roll, thus you might as well use passive skills (10 + relevant skill mod), IMO. In combat you get the risk/reward of a skill check by using your action (or in some classes, bonus action) to do the thing. So if you fail, its a waste that you wish you could have used on something else. Outside of combat, rolls can also have risks. Not every roll needs to have these risks, but when your players have a habit of glomming onto a failure, start adding risks instead of creating a strange system to circumvent their knowledge. If your player fails to open a lock, and does it badly enough, maybe they jam the lock. Now, it's impossible to break the lock. If your player fails to disarm a trap, the trap goes off. Your player fails to find a trap? While they were looking they noticed something else, that might convince them to move into a position that sets off the trap.
When there is a risk and benefit, you have them roll, so then you curb the effects of, after the fail, everyone else piling on claiming they'd also like to roll. The most intense moments of D&D can come down to when a roll is risky, whether the result is good or not. The good result the players get the benefit of this cool success that they feel pride in. The bad result, the intensity of the game is increased and the players get more invested. If a bad result is... 'You find nothing' 'You don't open the lock' you're not giving your players reasons to not just say 'oh yeah, i'll try next'. Raise the stakes.
I did acknowledge you can roll for the players; but not everyone is happy with that, especially when you screw up on their behalf. Personally, I like the players making as many rolls as possible. That way they can't blame their screw-ups on me :p I know that "random is random", so it doesn't matter who rolls, but they seem happier having their fate in their hands ( apparently ).
Letting them roll is fine in every other situation, but like I said, Stealth works differently from other rolls and gives players knowledge about the future. It's not unreasonable to handle that one check yourself.
Adding a secret lookup table isn't going to make them feel in control. They're no more in charge than when you roll for them (and in fact you are, because of the d6), since there's no correlation that they can tell between what they roll and what happens. It's no different from you rolling secretly for them.
It's simpler to adopt a "degree of failure" rule based on a single check: E.g. they needed a 12 to pick the lock, they rolled an 8, it will take them 4 x <some unit of base time> to get the lock open. You might ask them, "How long are you going to keep at it?", and if they say they're going to give up after 5 minutes, and you have determined it's going to take 11 minutes for them to puzzle the lock out, then they don't succeed.
And what do you tell them when they decide they want another 5 minutes? There's no in-universe reason why they can't just keep trying. All that accomplishes is increase the amount of time between rerolls and give yourself extra work by having to come up with these degree of failure mappings.
If there's no risk and no consequences for failure, just skip the dice. They're pointless.
Additionally, making the players detail each and every place they search, and rolling multiple times for searches seems tedious. I have a tendency to give the players "the benefit of the doubt" - if they're searching, their characters are experienced enough to conduct a thorough search; again, a single roll.
If you allow them to say "I search the room" and actually get results, they're just going to say "I search the room" every time. There's no decision-making process there, no gameplay.
Unless there's a benefit and a consequence to a roll, there's no real risk-reward to the roll, thus you might as well use passive skills (10 + relevant skill mod), IMO.
For traps and hidden creatures or objects you're already using passive Perception all the time though. You'd only be rolling if passive Perception failed.
Player: Damn .... 3 .... OK, next turn I'm going to ....
Don't roll until it matters (by which I mean when they can't just abandon the attempt or make another attempt without consequence), and that solves this problem.
Or this
Player #1: I'm going to search for traps
DM: Give me a skill roll
Player #1: Damn .... 3 ....
Player #2: I want to look for traps as well!
Player #3: Me too!
That's when I say "Okay, one of the two of you roll with advantage thanks to the other one using the Help action" or enforce a group check - and either way there is no repeated attempts until one finally succeeds because, again, there are no rolls made until the roll matters.
In my experience, once you remove the potential to benefit from the "I'll just do something else/try again next round" and "I'll try too" style of play, players stop looking for it and don't miss anything about it once it is gone - and instead of waiting for one player to fail a check and say "can I try?" they speak up more proactively and ask "can I help?".
Player perception/psychology is a consideration. I will concur with InquisitiveCoder's assertion that obscuring the roll does not solve this. Put a stake in the original idea.
Unrealistic player meta-gaming is to be avoided.
All skill rolls should be treated with the same "game mechanic".
Multiple "press the button to continue" rolls are pointless and tedious. Multiple skill rolls only make sense in time constrained situations like a battle, or a growing environmental threat, or a dramatic story deadline - in which case it's a "race the clock" scenario which has some dramatic worth.
Restrictions on rolls need to have an "in game" explanation.
I think you've all raised some excellent points. I would also agree that:
If an attempt to use a skill has no chance of success, or or failure, it's not a roll.
If an attempt to use a skill has no benefit or consequence, it's not a roll.
I would add the caveat, however, that that time consumed is a cost and that side effects are consequences - unless they're not, in which case they harmless descriptive fluff.
I think 1 & 3 are closely related. A player would ( likely ) be unhappy if you said "I'm going to make your combat rolls for you, but you get to make other rolls". I think the only reason DMs get away with Stealth being any different is that it's a "socially acceptable convention" at the gaming table - but it's no more, or less, fair than rolling any other check for the player.
Realistically, it doesn't matter who rolls a random number, but back to point #1, the player psychology of it is very different.
I like AaronOfBarbaria's idea of "deferring resolution" of "hidden actions" for this: OK, you're hiding - no don't roll yet, and only calling for the roll if/when they might be spotted.
For serial repeats of a skill attempt, I've agreed with the "no, you can't all roll, but you can give someone advantage" in the past - and I've used it myself (even 2 nights ago) - but I've never been sure what the "in game logic" is for preventing follow up attempts by participating individuals. It makes total sense from a game mechanics perspective - not so much from an "in world' one.
I think I like MellieDM's idea of "rising cost of failure" for this better; players can "dog pile" on the problem and make serial skill rolls, but their very involvement in the problem makes it harder. Each success and failure has a tangible consequence. That's brilliant. It works great for active skills - picking a lock, disarming a trap, etc. I did however, struggle with how this can be applied to something socially passive like Insight checks; NPCs don't get "harder to read" just because someone thought about what they said, or did ( the answer is that it's not really the Players that are acting, and that multiple players all acting independently and serially isn't a problem here - they're really all making a perception "saving throw" against the NPC's attempt to Persuade or Deceive, and actually all witnessing characters should roll - but only once).
You can even combine the two: Alice, Bob, & Charlie all cooperate trying to find the Wumpus in the thicket, before the angry crowd catches up to them ( time pressure ). Alice alone rolls with advantage, but they fail, and the Wumpus burrows under a log ( consequence, adding +2 to the next check DC ). Bob manages to outwit the mob, circles back ahead of his pursuers for another quick look ( still time pressure, no artificial restriction on his attempt, but a higher DC ), and rolls a natural 20 - Wumpus found!
I think "picking the lock" and "searching the room" are mechanically the same, and have to be treated the same, just as I think Stealth and Attack rolls should be treated the same.
In all cases, if there is no time constraint, a non-zero chance of success, and no negative consequences for repeated attempts, then I agree that there is almost no need for a roll. There is certainly no need for a roll to determine success, but I think duration of effort, and possible side effects, are important.
In the absence of time pressure, there's no need for a Rogue to make repeated rolls for different lock-picking attempts; there's no need for an investigator to make multiple rolls for different locations. "Do you want to roll again?", and "Did you check under the credenza?" are equally pointless and tedious. There is no decision making, or game play, in either case - they are going to succeed.
However, It is ludicrous to think a 1st level Rogue and a 20th level Rogue are going to have identical experiences and side-effects picking a master-level lock, just because they both have theoretically unlimited undisturbed time. A 20th level Rogue might breeze through it in seconds, leaving the lock pristine, while a 1st level might take hours to crack it, and severely mar the exterior, making it obvious that it has been tampered with. Likewise, a skilled investigator can still search a room quickly and leave it undisturbed, while any thug can "toss" the room and eventually find everything there is to find. Everyone will succeed, no roll ( for success ) needed, but the results and duration are very different.
Personally, I still like the idea of having the time and side-effects scaling with a Player skill roll. It gives random variation, uncertainty, and it gives the player a sense of agency being "involved" in the outcome - but there is no reason why you could not compare the DC of the lock ( or and "obscurity rating" of the hidden items ), against the passive rating of the skill used, and scale according to that.
In cases where there is time pressure, the above system of allowable serial checks, against the same target, with added difficulties - with the rising pressure of the looming deadline, is fine. In the case of multiple people with different targets - for example different people searching different areas of a room - they all roll independently. There's another corner case where there are different items to find, with different DCs, in a single area, against a PCs single search attempt - but I'll take that one away, for now.
In the case of there being no chance of success, again, no roll is needed for success - they fail. But the question still remains - how much time will it take before the PC realizes that it is hopeless, and what side effects will they cause along the way? I think that has significance, and again, I like the idea of a skill roll determining that aspect.
I don't think there's an issue with the player saying "OK, I'll go for another 10 minutes, then", even repeatedly, since there's no more die rolling to be done ( if there ever was any; remember you can do some static skill/DC comparisons ). Realistically, I'd probably say to the player, "OK, enough, what's your absolute outside time limit", and hold them to it, after the third extension, however.
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I realize it might not be for everybody, but I ran a short campaign once where the players made zero rolls, for anything, didn't even have dice. Instead, they described an intended action, I made all rolls secretly, and then described the outcome. "I want to attack the bandit" led to "Your swing your halberd with all your might over your head and it lands into the bandit's shoulder, splitting him in two" or "Your swing completely whiffs" or some such. Or for skills, the players would say something like "We attempt to move silently through the forest" and would get a response like "The rogue glides deftly between the trees, making no sound, while the cleric sounds like a rampaging elephant."
For us, it removed the "mechanics" of playing the game, and let the players focus on describing intent rather than looking up a set of allowed actions and choosing from those. They still got feedback on the results, but rather than just "you rolled a 3" they got a description that then led to more options or alternative actions, or (muahaha) terrible consequences. The monk wants to try to bash down a door? Sure, go ahead and try. Don't focus on a door DC and a strength modifier and a roll, just do it! I mean, sure, if you had known it was DC 20 and you would bust your shoulder even trying, you might not have even done it, but where's the fun in that?
Anyway, I know it's a little outside the norm and may not help with your situation exactly, but the players had fun and I had fun describing the critical successes and failures of their actions removed from the underlying mechanics entirely. I guess my point is that secret rolls should be fine, and if your players take issue with it, tell them to get over it and soon enough they will. :)
According to Matt Colville, that's how the "original DMs" like Gary Gygax originally did it.
It certainly has the advantages you describe - and it would be interesting/fun to try as an experiment some day - but I can't see many modern players being happy with this.
For many people, rolling the dice is part of the fun.
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I'm sure this has happened to us all:
Player: I'm going to use my bonus action to hide
DM: Give me a stealth roll
Player: Damn .... 3 .... OK, next turn I'm going to ....
Or this
Player #1: I'm going to search for traps
DM: Give me a skill roll
Player #1: Damn .... 3 ....
Player #2: I want to look for traps as well!
Player #3: Me too!
Sometimes the player just isn't supposed to know how well the character is really doing. The character might think they did OK, and be wrong ( evil DM cackle ).
Sure the DM can make such rolls for the Player - but the Player might get cranky if you roll badly for them.
I'm thinking about using a quick "lookup matrix" - as below - for this kind of roll. The player would make a D6 and a D20 roll together for a skill roll. D6 is the column, D20 is the skill roll.
Player: I'm going to use my bonus action to hide
DM: Give me a masked stealth roll
Player: Um ... 5 & 19 ... ?
DM: What's your bonus?
Player: +4
DM (jotting down 8): OK, you duck behind the scrub brushes, and freeze in place.
The D6 roll wouldn't strictly be needed, but if there was only one randomly shuffled columns, then players would start to notice "11 is good, 16 is bad" pretty quickly.
The DM can either do the math for the bonus ... or you could even make a stack of different matrices ( +1 matrix with values 2 through 21, +2 matrix with values 3 through 22, etc.), or even do it "live" in a spreadsheet.
Anyone tried anything like this?
01 02 03 04 05 06
01 15 06 11 03 18 01
02 02 19 13 12 10 14
03 03 07 05 17 07 15
04 08 04 03 09 15 07
05 01 01 01 08 11 02
06 05 09 15 14 06 18
07 06 10 12 15 08 20
08 12 14 20 05 03 09
09 11 03 18 02 17 16
10 13 08 10 10 16 08
11 17 18 04 06 09 17
12 19 02 06 16 19 10
13 07 16 02 18 13 12
14 10 05 17 19 12 11
15 14 20 09 01 02 13
16 04 17 14 07 01 05
17 18 15 19 11 20 06
18 09 12 16 13 14 04
19 20 13 07 04 04 19
20 16 11 08 20 05 03
My DM Philosophy, as summed up by other people: https://drive.google.com/file/d/1rN5w4-azTq3Kbn0Yvk9nfqQhwQ1R5by1/view
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The stealth roll isn't a problem in combat. The player's character should be able to tell that someone's spotted them; the feedback is immediate. The real problem with Stealth happens out of combat, because you roll for it up front when you start traveling, so if you roll a 3 you know you're going to get caught as soon as you come across a monster. I solve this by rolling secretly for every player when they start moving.
The "search for traps" scenario can be solved easily by changing how you're handling the ability checks. Search is an action you can take in combat, so it's possible roll a Perception check and find a hidden creature, object or trap in 1 round. There's also no consequences for failing; they can try again next round. The same should hold true out of combat.
Ask them to be specific about where they're looking ("under the rug", "in the desk drawers", etc) and take the DMG's advice on repeated checks: if it's possible for them to succeed, they do so after x10 the duration of a single attempt (so, 1 minute). If multiple players want to search, you can divide the time if they're searching in the same place or they can split up the room. If they're searching walls or floor for pressure plates/hidden doors, each 5 foot square takes 1 minute. If they're in a dungeon, they're not going to want to spend an hour per room or they risk having more random encounters.
The Forum Infestation (TM)
Good points.
A couple of counter-points ( by which I mean I'm not arguing against you, I'm just batting the ideas around to see how they hold up, and where things land :) )
I did acknowledge you can roll for the players; but not everyone is happy with that, especially when you screw up on their behalf. Personally, I like the players making as many rolls as possible. That way they can't blame their screw-ups on me :p I know that "random is random", so it doesn't matter who rolls, but they seem happier having their fate in their hands ( apparently ).
Akin to the "take x10 the time" rule, I would say if there's no consequence for failing a skill roll outside of combat, there's no point in making them roll over and over - they will keep rolling until they "get it right".
It's simpler to adopt a "degree of failure" rule based on a single check: E.g. they needed a 12 to pick the lock, they rolled an 8, it will take them 4 x <some unit of base time> to get the lock open. You might ask them, "How long are you going to keep at it?", and if they say they're going to give up after 5 minutes, and you have determined it's going to take 11 minutes for them to puzzle the lock out, then they don't succeed.
It's still a single die roll.
In combat, or some other time pressure ( can they get the hatch open before the water level in the room gets too high? ), absolutely keep making individual rolls going each round. That has dramatic tension.
Additionally, making the players detail each and every place they search, and rolling multiple times for searches seems tedious. I have a tendency to give the players "the benefit of the doubt" - if they're searching, their characters are experienced enough to conduct a thorough search; again, a single roll.
Adopting your example, I might ask how long they're searching, and where each of the players are searching, and again, they make a single roll each.
However,
The problem isn't with multiple players searching, or trying to gain Insight on an NPC, etc. - it's the meta-gaming of players making choices for their characters because they know that someone else failed a roll, when they wouldn't have otherwise acted if they didn't know - and there's no way the character would know.
The only way I see to prevent that is to take away that knowledge.
Either you make the roll for them - which appear to be the standard response, but takes away some of the player agency IMHO - or make their roll not obviously be a success/failure when they wouldn't know if was a success/failure; this idea is a crack at doing the latter.
In your case of combat hiding, then yes - a "normal" skill check would make the most sense. In hiding from the patrol - they wouldn't know right away.
My DM Philosophy, as summed up by other people: https://drive.google.com/file/d/1rN5w4-azTq3Kbn0Yvk9nfqQhwQ1R5by1/view
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Unless there's a benefit and a consequence to a roll, there's no real risk-reward to the roll, thus you might as well use passive skills (10 + relevant skill mod), IMO. In combat you get the risk/reward of a skill check by using your action (or in some classes, bonus action) to do the thing. So if you fail, its a waste that you wish you could have used on something else. Outside of combat, rolls can also have risks. Not every roll needs to have these risks, but when your players have a habit of glomming onto a failure, start adding risks instead of creating a strange system to circumvent their knowledge. If your player fails to open a lock, and does it badly enough, maybe they jam the lock. Now, it's impossible to break the lock. If your player fails to disarm a trap, the trap goes off. Your player fails to find a trap? While they were looking they noticed something else, that might convince them to move into a position that sets off the trap.
When there is a risk and benefit, you have them roll, so then you curb the effects of, after the fail, everyone else piling on claiming they'd also like to roll. The most intense moments of D&D can come down to when a roll is risky, whether the result is good or not. The good result the players get the benefit of this cool success that they feel pride in. The bad result, the intensity of the game is increased and the players get more invested. If a bad result is... 'You find nothing' 'You don't open the lock' you're not giving your players reasons to not just say 'oh yeah, i'll try next'. Raise the stakes.
Letting them roll is fine in every other situation, but like I said, Stealth works differently from other rolls and gives players knowledge about the future. It's not unreasonable to handle that one check yourself.
Adding a secret lookup table isn't going to make them feel in control. They're no more in charge than when you roll for them (and in fact you are, because of the d6), since there's no correlation that they can tell between what they roll and what happens. It's no different from you rolling secretly for them.
And what do you tell them when they decide they want another 5 minutes? There's no in-universe reason why they can't just keep trying. All that accomplishes is increase the amount of time between rerolls and give yourself extra work by having to come up with these degree of failure mappings.
If there's no risk and no consequences for failure, just skip the dice. They're pointless.
If you allow them to say "I search the room" and actually get results, they're just going to say "I search the room" every time. There's no decision-making process there, no gameplay.
For traps and hidden creatures or objects you're already using passive Perception all the time though. You'd only be rolling if passive Perception failed.
The Forum Infestation (TM)
Don't roll until it matters (by which I mean when they can't just abandon the attempt or make another attempt without consequence), and that solves this problem.
That's when I say "Okay, one of the two of you roll with advantage thanks to the other one using the Help action" or enforce a group check - and either way there is no repeated attempts until one finally succeeds because, again, there are no rolls made until the roll matters.In my experience, once you remove the potential to benefit from the "I'll just do something else/try again next round" and "I'll try too" style of play, players stop looking for it and don't miss anything about it once it is gone - and instead of waiting for one player to fail a check and say "can I try?" they speak up more proactively and ask "can I help?".
OK - some basic premise that I'm sticking to:
I think you've all raised some excellent points. I would also agree that:
I would add the caveat, however, that that time consumed is a cost and that side effects are consequences - unless they're not, in which case they harmless descriptive fluff.
I think 1 & 3 are closely related. A player would ( likely ) be unhappy if you said "I'm going to make your combat rolls for you, but you get to make other rolls". I think the only reason DMs get away with Stealth being any different is that it's a "socially acceptable convention" at the gaming table - but it's no more, or less, fair than rolling any other check for the player.
Realistically, it doesn't matter who rolls a random number, but back to point #1, the player psychology of it is very different.
I like AaronOfBarbaria's idea of "deferring resolution" of "hidden actions" for this: OK, you're hiding - no don't roll yet, and only calling for the roll if/when they might be spotted.
For serial repeats of a skill attempt, I've agreed with the "no, you can't all roll, but you can give someone advantage" in the past - and I've used it myself (even 2 nights ago) - but I've never been sure what the "in game logic" is for preventing follow up attempts by participating individuals. It makes total sense from a game mechanics perspective - not so much from an "in world' one.
I think I like MellieDM's idea of "rising cost of failure" for this better; players can "dog pile" on the problem and make serial skill rolls, but their very involvement in the problem makes it harder. Each success and failure has a tangible consequence. That's brilliant. It works great for active skills - picking a lock, disarming a trap, etc. I did however, struggle with how this can be applied to something socially passive like Insight checks; NPCs don't get "harder to read" just because someone thought about what they said, or did ( the answer is that it's not really the Players that are acting, and that multiple players all acting independently and serially isn't a problem here - they're really all making a perception "saving throw" against the NPC's attempt to Persuade or Deceive, and actually all witnessing characters should roll - but only once).
You can even combine the two: Alice, Bob, & Charlie all cooperate trying to find the Wumpus in the thicket, before the angry crowd catches up to them ( time pressure ). Alice alone rolls with advantage, but they fail, and the Wumpus burrows under a log ( consequence, adding +2 to the next check DC ). Bob manages to outwit the mob, circles back ahead of his pursuers for another quick look ( still time pressure, no artificial restriction on his attempt, but a higher DC ), and rolls a natural 20 - Wumpus found!
I think "picking the lock" and "searching the room" are mechanically the same, and have to be treated the same, just as I think Stealth and Attack rolls should be treated the same.
In all cases, if there is no time constraint, a non-zero chance of success, and no negative consequences for repeated attempts, then I agree that there is almost no need for a roll. There is certainly no need for a roll to determine success, but I think duration of effort, and possible side effects, are important.
In the absence of time pressure, there's no need for a Rogue to make repeated rolls for different lock-picking attempts; there's no need for an investigator to make multiple rolls for different locations. "Do you want to roll again?", and "Did you check under the credenza?" are equally pointless and tedious. There is no decision making, or game play, in either case - they are going to succeed.
However, It is ludicrous to think a 1st level Rogue and a 20th level Rogue are going to have identical experiences and side-effects picking a master-level lock, just because they both have theoretically unlimited undisturbed time. A 20th level Rogue might breeze through it in seconds, leaving the lock pristine, while a 1st level might take hours to crack it, and severely mar the exterior, making it obvious that it has been tampered with. Likewise, a skilled investigator can still search a room quickly and leave it undisturbed, while any thug can "toss" the room and eventually find everything there is to find. Everyone will succeed, no roll ( for success ) needed, but the results and duration are very different.
Personally, I still like the idea of having the time and side-effects scaling with a Player skill roll. It gives random variation, uncertainty, and it gives the player a sense of agency being "involved" in the outcome - but there is no reason why you could not compare the DC of the lock ( or and "obscurity rating" of the hidden items ), against the passive rating of the skill used, and scale according to that.
In cases where there is time pressure, the above system of allowable serial checks, against the same target, with added difficulties - with the rising pressure of the looming deadline, is fine. In the case of multiple people with different targets - for example different people searching different areas of a room - they all roll independently. There's another corner case where there are different items to find, with different DCs, in a single area, against a PCs single search attempt - but I'll take that one away, for now.
In the case of there being no chance of success, again, no roll is needed for success - they fail. But the question still remains - how much time will it take before the PC realizes that it is hopeless, and what side effects will they cause along the way? I think that has significance, and again, I like the idea of a skill roll determining that aspect.
I don't think there's an issue with the player saying "OK, I'll go for another 10 minutes, then", even repeatedly, since there's no more die rolling to be done ( if there ever was any; remember you can do some static skill/DC comparisons ). Realistically, I'd probably say to the player, "OK, enough, what's your absolute outside time limit", and hold them to it, after the third extension, however.
My DM Philosophy, as summed up by other people: https://drive.google.com/file/d/1rN5w4-azTq3Kbn0Yvk9nfqQhwQ1R5by1/view
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I realize it might not be for everybody, but I ran a short campaign once where the players made zero rolls, for anything, didn't even have dice. Instead, they described an intended action, I made all rolls secretly, and then described the outcome. "I want to attack the bandit" led to "Your swing your halberd with all your might over your head and it lands into the bandit's shoulder, splitting him in two" or "Your swing completely whiffs" or some such. Or for skills, the players would say something like "We attempt to move silently through the forest" and would get a response like "The rogue glides deftly between the trees, making no sound, while the cleric sounds like a rampaging elephant."
For us, it removed the "mechanics" of playing the game, and let the players focus on describing intent rather than looking up a set of allowed actions and choosing from those. They still got feedback on the results, but rather than just "you rolled a 3" they got a description that then led to more options or alternative actions, or (muahaha) terrible consequences. The monk wants to try to bash down a door? Sure, go ahead and try. Don't focus on a door DC and a strength modifier and a roll, just do it! I mean, sure, if you had known it was DC 20 and you would bust your shoulder even trying, you might not have even done it, but where's the fun in that?
Anyway, I know it's a little outside the norm and may not help with your situation exactly, but the players had fun and I had fun describing the critical successes and failures of their actions removed from the underlying mechanics entirely. I guess my point is that secret rolls should be fine, and if your players take issue with it, tell them to get over it and soon enough they will. :)
According to Matt Colville, that's how the "original DMs" like Gary Gygax originally did it.
It certainly has the advantages you describe - and it would be interesting/fun to try as an experiment some day - but I can't see many modern players being happy with this.
For many people, rolling the dice is part of the fun.
My DM Philosophy, as summed up by other people: https://drive.google.com/file/d/1rN5w4-azTq3Kbn0Yvk9nfqQhwQ1R5by1/view
Disclaimer: This signature is a badge of membership in the Forum Loudmouth Club. We are all friends. We are not attacking each other. We are engaging in spirited, friendly debate with one another. We may get snarky, but these are not attacks. Thank you for not reporting us.