We have a DM difference of opinion here regarding ability checks. There may not even be a "right" answer -- it may be completely preference-based -- but I want to hear what you all think.
The following assumes a group of experienced D&D players.
School of Thought 1: DMs should never prompt players for ability checks
Ability checks are things players actively decide to do, not something the DM can impose.
If a player says "Can we tell what sigil the mage has upon his crest?," the DM shouldn't request a Perception check, but rather say "It's unclear whether you can tell from this distance" and let the player declare for him/herself that an ability check for Perception will be made.
Any checks a DM would normally prompt ("Go ahead and make a Perception check," "Make a History check," etc.) should just be done using the charaters' passive ability scores. If it's something the player is actively doing ("Okay, I'm going to search the room for clues"), that player should proactively make the appropriate ability check without the DM requesting one ever.
For example, the party is traveling down the road, and the DM asks everyone what they're doing. A few adventurers are being passive, but one player says his/her character is keeping active watch for enemies. If there is an archer slowly creeping out from behind a tree, the DM should use the lead character's Passive Wisdom (Perception) score to see whether they notice the archer poking out from behind the tree.
School of Thought 2: DMs should prompt ability checks when called for
Ability checks are things players actively decide to do, but the DM can prompt a check to make the game run smoother and to establish his/her preferred check
If a player says "What type of berries are on the bush?," the DM's responsibility is to prompt a check so the players don't make assumptions ("Go ahead and make a Nature check").
Passive ability scores should only be used by the DM is when the players are doing anything passively (not paying too much attention while traveling down a road).
For example, the party is traveling down the road, and the DM asks everyone what they're doing. A few adventurers are being passive, but one player says his/her character is keeping active watch for enemies. If there is an archer slowly creeping out from behind a tree, the DM should prompt for a Perception check for the active character to see if they notice the archer in time.
I firmly believe that there is no right or wrong way to do this - it's for each group to play how they prefer.
My personal style when I DM is that I prefer the players to only roll dice for skills when I prompt them to do so and I often don't tell them the exact difficulty number. I often effectively use passive checks to keep the pace going.
My reasoning is such:
If there's some cool roleplay going on, I don't want to break it by asking the player to make a charisma roll. I know what stats and proficiencies each character has and I'll only ask for a roll if I am unsure on the outcome, or I think it unlikely the npc will be persuaded.
It sucks to be the 20 strength barbarian and roll a 2 on your athletics check to smash a door down, only to have the gnome wizard roll a 20 and do it for you.
Players in games I run are always able to ask, "Can I make a roll against <skill x>?" if they want, but I might just say no, if I feel it's not relevant.
With regards DC of checks, I usually mention the difficulty LEVEL of the check, "Climbing up the side of this cliff is going to be difficult, especially for the Wizard" - I may have mentally set the DC at 18 for success, but if, for example, the rogue with expertise in athletics rolls a total of 17, I am not going to say they fall - I'll describe them being near the top and misjudging the last foothold and it giving way and they're about to fall - make a dex save to see if you can hang on, or do you have another plan?
Depends on your flavor of ice cream, I personally don't like when players ask to do skill checks because it often makes no sense. Just like when they want to re roll skill checks for each other. Because what even is a skill check besides a guideline for the DM to adjudicate what is happening.
With a group of new players I let the NPC do a lot more checks to show by example. As well as occasionally ask the players for a check. Over time it becomes a lot less as they learn the possibilities. Then most checks are up to them. Which brings us to the next step.. They have to ask for a check. Players who aren't into RP yet will just say: "I enter a room and want to check for traps with a perception check". Which I allow. Afterwards I just gradually get them to just describe their actions and not think about the checks and leave it to me to decide which check would be appropriate for what they want to do and narrate it as much as possible. That way I can hopefully get them, too gradually, get more into roleplaying habits and less of mechanical gaming approach. I won't let my characters make pro-active rolls. Checking for traps with perception would be the usual thing... but what if the traps I have setup require more of an investigation instead? My players often just roll the D20 then wait for me to tell them which skill to add to it.
During travel when one character has decided to be to look-out/scout it would be odd to use their passive perception to notice an opponent appearing from behind a tree. They're keeping an active watch after all. That said there still is the chance the opponent has high enough stealth to evade that active perception and get an ambush/surprise going. Or the other way around. However when my players are exploring in the woods, and there is smoke rising in the distance, then I do indeed use the passive perception and tell the person with 12+ passive perception what they noticed. Its rather situational and is decided on during preparation what can be done with passive checks and what not.
When it comes to a 20str warrior failing a strength based check on a climb.. Well it depends on situation. If there is no pressure then just auto succeed. The roll is then more too describe if it was easy or barely success, but a success nonetheless. During situations with pressure I would let the dice decide ... its funny to see a strong warrior fail and the scrawny wizard succeed. Creates some nice inter-personal situations where the warrior will get teased for a bit or something. Its often funny. Such as the rogue carefully opening a door. Then the cleric barged in and opened a barrel that unleashed a mephit. Later the cleric carefully opened a hidden door and the barbarian ran in opening the sarcophagus... which unleashed a horde of skeletons on the party. Even out of game teasing weeks later happened. It can add to the fun and involvement.
During conversation I just let it play out naturally and afterwards have the rolls done, instead of in between. Depending on how they spoke and handled themselves I might grant an advantage to their charisma check. Especially since none of them has invested in Charisma to begin with.
Generally I prefer to use passives and call upon character rolls for specialties. "you are asked find an artifact, wizard, roll arcana to see how much you know about what you may be going in to" for example. I find it keeps things going, that they're rolling at all I've generally got a range of what you know depending on how high they roll rather than rolling to see if they know anything at all - the passive intelligence tells me the wizard has a vague knowledge of it. They won't be rolling a 3 and being told "you know nothing" it'll just be a basic "you don't know too much but you're aware that *insert cult here* have been searching for it" giving them a guideline of the enemies. A 20+ will tell them potential enemies, what it can do, who made it and all sorts of information. I find it helps me control the table a little easier and prevents the things I see at the table as a player for other DMs where it's devolved to "I roll perception to see if I see anything" - rolls a 6 and told nothing - next party member says "oh yeah I'll look as well then" - rolls low and continue until someone gets a very high roll and is told there really is nothing there.
I am always happy to let players ask to attempt a roll if they would like to try something and play it by ear though. It's near impossible for a DM to predict exactly how a group of players are going to react after all, as a result I tend to hand over almost total control to them when it comes to a tactical scenario and executing a plan. I will decide the best thing to roll on and sometimes simplify a sequence to just the one roll based on the actions they plan to take but they have their destiny in their hands. It sort of represents a highlight reel. A player doesn't need to spend too long actively calling for and taking extra rolls to find out lore information or something that they'll routinely be able to handle but they have near complete control when they're trying to pull something off on a more impulsive nature. I still won't allow the aforementioned "well X failed so I'll try it instead" circle though!
I'm in neither camp because some of them contradict or conflict within each of the choices.
I much prefer players to just tell me what they're rolling for, before they start rolling. I don't like being 'asked' because it slows down the game and it's just annoying to be a babysitter/gatekeeper. So you find some berries on a bush and say, "I'm rolling a nature check to see if I know what the berries are and if they're poisonous or not. I got... a 15," and then, I decide if a nature check is appropriate to identify the berries (perhaps they're entirely magically created and simply don't exist anywhere in nature, for instance), and if the check is good enough for any information, no information, misleading information, or highly detailed information.
Unfortunately most players seem really reluctant to do things this way so I often end up prompting before I realise I'm doing it, just because I get frustrated when the game slows to a crawl with nothing really happening.
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"Most people are other people. Their thoughts are someone else's opinions, their lives a mimicry, their passions a quotation."
Letting each player roll until one has a success is indeed obnoxious and slows things down to a crawl. If such a situation happens regularly things get out of hand. I just simply won't allow for anymore of such checks and only the ones with a trained skill in it is allowed to do so. Perhaps with advantage if another player helps out looking for something. Thankfully my players aren't like that and have settled into a flow where they know a bit of each other. They know who is better as certain things. Which results in one character asking another to keep their eyes out for something. Or they discuss in which order to go in a room and as such work together more often.
I'd say #2. If a skill check is called for, that's a DM thing.
PCs aren't aware of game mechanics, so asking a player to be responsible for adjudicating what skill is called for, when, is strange.
Plus, as a DM, I have access to the information that the player is asking for. If the player asks me what crest appears on the wizard's robe, I may very well answer "He is wearing the crest of the laughing coffin" and move on from there, short-cutting any need for any one to roll anything. The fact that I've already declared that the information is not immediately available to the player means that I've already decided to put that info behind a skill check wall. Making the player ask the same question multiple times to get a straight answer just seems pointless.
Im of the opinion that DM's should be asking for rolls and checks, this helps the flow of roleplay a lot because the players done need to be thinking 'im looking out so I need to roll perception!' its just 'im on guard looking out for enemies' then they are prompted by the DM. In my opinion and experience it helps to cut down on the perception train that others have been talking about because you can get a list of what people are doing; ask the PC's what they are doing after a battle: 2 rummage through loot, 1 looks out for enemies and the other is trying to unlock a door moving forward. Once you get that list and idea you start doing rolls, 2 investigation, 1 perception and 1 thieves tools, that might prompt others to look out aswell realising there is one look out however most of the time it is done before. If it is a super low roll then I will go off passive perception of the other PCs! The look out gets 3 on their roll but someone is sneaking up with a 8 stealth the others are going to realise them with their passive perception just glancing down the hallway etc.
Got proactive, experienced players who consistently tell you they're making the appropriate checks for the situation they're in? Don't prompt. Have players they never check, or try to handle animal their way past a group of guards or intimidate traps? Prompt.
Don't worry about them, the answer is in the words the players use and their passives.
---
"You walk into the chamber, there's a pile of rubble directly in front of you. You look up and see the ceiling has collapsed here, a large boulder stuck in the hole like an over sized golf-ball. On the walls you see murals, hunters chasing down stags, dogs chasing foxes, pheasants in flight with arrows following. A statue of what looks like a half man, half wolf is displayed in the center of the room, almost as if it's honorific. You're guessing it's a werewolf, but it's odd to see one honored."
*DM steps over to a player and whispers in their ear and passes a note to a second player*
Whisper: "You notice the faint glint of a metallic wire extending out from the pile of rubble in both directions parallel to the door you're in". Note: "You feel like you've heard of a lycanthrope cult, the name Malar is stuck in the back of your mind".
*DM sits back down*
"The rest of the room seems as though it used to have wooden benches as there are rotten planks scattered about the floor on either side of the room. The dust on the floor is thick, leaving you to believe it's been years since someone has been down here. Except the odd depressions that look very much like rat tracks and some sort of very large dog. Those tracks seem fresh, you're guessing weeks old at the most."
---
At this point in time I have looked at a post it note on my DM screen and saw that no one had a passive under 11, and there was one person who had a passive of 15. The person with the 15 was given the information about the wire. The Bard in the group got the note, simply because of the fact that stories are what bards do and remembering odd facts is natural. All of the other information is gleaned using every day common sense, normal experiences one might have, and the assumption that people can put information together without major leaps of logic.
Prompt: Immediate threat or failure: Falling rocks, trying to look into the window of a passing carriage, reading lips.
No Prompt: Action based threat or failure: checking for traps, trying to remember more than what was presented in a description, avoiding detection while sneaking around
Automatic information: Anything that you could discern from spending a moment of looking around and using your grey matter. Common sense information based on any and all media, just because it's a movie to us doesn't mean it can't be a campfire story for them. All passive checks.
It should be clear that #1 is the wrong answer. You should never expect your players to be the sole arbiters of when an ability check is appropriate or to have the sole responsibility for determining the ability check they should make in a situation. They might sometimes request to make a specific check, and that is totally acceptable, but what you absolutely should not do is describe something (in vague terms no less) and then expect your players to figure out what ability check they need to make. If you're doing this, then you're 100% wrong.
To use an example from the original post:
If a player says "Can we tell what sigil the mage has upon his crest?," the DM shouldn't request a Perception check, but rather say "It's unclear whether you can tell from this distance.
If I had a DM that said this to me as a player, it would drive me insane. What does the phrase, "it's unclear whether you can tell from this distance" even mean? As a player, I wouldn't have know whether I was being told a Perception check was not possible here, not appropriate for some reason, not likely to succeed, or if the DM was simply expecting me to decide to do their job for them and figure out that a Perception check was required. This is not the correct way to DM. Please do not do this.
Otherwise, I don't think there's a right answer here. Perhaps the most natural approach is that the players describe their characters' actions and then the DM decides which ability check is appropriate. This also makes it much easier to decide when to apply advantage/disadvantage or other circumstantial bonuses, as these will be determined not just by what a character decides to do but how they decide to do it. But there are other scenarios where the DM should prompt the players to make a check, or where using a passive score is appropriate, or where players might request to make a particular check. These can all be decided on a case-by-case basis.
Several people mentioned cases where several players request to make the same check. There are cases where it makes sense to limit who can make a check based on proficiency or some other aspect of a situation, but in other cases, it's entirely acceptable and realistic that everyone will want to make a check. The "train" of one character asking to make a check, and then another, and then another, is a failure by the DM, not the players; you should be able to anticipate when all players will want to make a check (and when all characters are capable of doing so) and just prompt everyone to make this check from the get-go. If you create a scenario where all characters could attempt to do something, and then you only allow some characters to attempt it, then you've just decided to artificially limit the agency of the players and their characters.
Anyone who says anyone else's DMing style is wrong is wrong. With experienced enough players, you don't need to prompt. A group I'm running now has 3 players, all of them pros and veterans. I have yet to prompt a roll or tell them a roll isn't appropriate for their situation.
I think you may have missed my point. The original poster phrased this an unequivocal statement. "DMs should never prompt their players for ability checks." This is categorically wrong, and it's not a question of DMing style. It is the DM's job to adjudicate ability checks, as with all other rules of the game.
But the caveat is, as you've noted, only when it's required. You're lucky to have players who are experienced enough to not require prompting and who have a very good sense of what ability checks are appropriate for a situation. If players want to be proactive and request to make specific ability checks, more power to them. But this is not true of all players, or even of most players, and the fact remains that you can't expect players to bear this responsibility.
If a DM describes a situation, and the players know what they want to do but are completely unsure of what type of ability check they should make, the DM shouldn't just wait for the players to figure it out.
Hey everyone,
We have a DM difference of opinion here regarding ability checks. There may not even be a "right" answer -- it may be completely preference-based -- but I want to hear what you all think.
The following assumes a group of experienced D&D players.
School of Thought 1: DMs should never prompt players for ability checks
School of Thought 2: DMs should prompt ability checks when called for
I firmly believe that there is no right or wrong way to do this - it's for each group to play how they prefer.
My personal style when I DM is that I prefer the players to only roll dice for skills when I prompt them to do so and I often don't tell them the exact difficulty number. I often effectively use passive checks to keep the pace going.
My reasoning is such:
Players in games I run are always able to ask, "Can I make a roll against <skill x>?" if they want, but I might just say no, if I feel it's not relevant.
With regards DC of checks, I usually mention the difficulty LEVEL of the check, "Climbing up the side of this cliff is going to be difficult, especially for the Wizard" - I may have mentally set the DC at 18 for success, but if, for example, the rogue with expertise in athletics rolls a total of 17, I am not going to say they fall - I'll describe them being near the top and misjudging the last foothold and it giving way and they're about to fall - make a dex save to see if you can hang on, or do you have another plan?
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Depends on your flavor of ice cream, I personally don't like when players ask to do skill checks because it often makes no sense. Just like when they want to re roll skill checks for each other. Because what even is a skill check besides a guideline for the DM to adjudicate what is happening.
With a group of new players I let the NPC do a lot more checks to show by example. As well as occasionally ask the players for a check. Over time it becomes a lot less as they learn the possibilities. Then most checks are up to them. Which brings us to the next step.. They have to ask for a check. Players who aren't into RP yet will just say: "I enter a room and want to check for traps with a perception check". Which I allow. Afterwards I just gradually get them to just describe their actions and not think about the checks and leave it to me to decide which check would be appropriate for what they want to do and narrate it as much as possible. That way I can hopefully get them, too gradually, get more into roleplaying habits and less of mechanical gaming approach. I won't let my characters make pro-active rolls. Checking for traps with perception would be the usual thing... but what if the traps I have setup require more of an investigation instead? My players often just roll the D20 then wait for me to tell them which skill to add to it.
During travel when one character has decided to be to look-out/scout it would be odd to use their passive perception to notice an opponent appearing from behind a tree. They're keeping an active watch after all. That said there still is the chance the opponent has high enough stealth to evade that active perception and get an ambush/surprise going. Or the other way around. However when my players are exploring in the woods, and there is smoke rising in the distance, then I do indeed use the passive perception and tell the person with 12+ passive perception what they noticed. Its rather situational and is decided on during preparation what can be done with passive checks and what not.
When it comes to a 20str warrior failing a strength based check on a climb.. Well it depends on situation. If there is no pressure then just auto succeed. The roll is then more too describe if it was easy or barely success, but a success nonetheless. During situations with pressure I would let the dice decide ... its funny to see a strong warrior fail and the scrawny wizard succeed. Creates some nice inter-personal situations where the warrior will get teased for a bit or something. Its often funny. Such as the rogue carefully opening a door. Then the cleric barged in and opened a barrel that unleashed a mephit. Later the cleric carefully opened a hidden door and the barbarian ran in opening the sarcophagus... which unleashed a horde of skeletons on the party. Even out of game teasing weeks later happened. It can add to the fun and involvement.
During conversation I just let it play out naturally and afterwards have the rolls done, instead of in between. Depending on how they spoke and handled themselves I might grant an advantage to their charisma check. Especially since none of them has invested in Charisma to begin with.
Guess I'm a mix of both methods.
Generally I prefer to use passives and call upon character rolls for specialties. "you are asked find an artifact, wizard, roll arcana to see how much you know about what you may be going in to" for example. I find it keeps things going, that they're rolling at all I've generally got a range of what you know depending on how high they roll rather than rolling to see if they know anything at all - the passive intelligence tells me the wizard has a vague knowledge of it. They won't be rolling a 3 and being told "you know nothing" it'll just be a basic "you don't know too much but you're aware that *insert cult here* have been searching for it" giving them a guideline of the enemies. A 20+ will tell them potential enemies, what it can do, who made it and all sorts of information. I find it helps me control the table a little easier and prevents the things I see at the table as a player for other DMs where it's devolved to "I roll perception to see if I see anything" - rolls a 6 and told nothing - next party member says "oh yeah I'll look as well then" - rolls low and continue until someone gets a very high roll and is told there really is nothing there.
I am always happy to let players ask to attempt a roll if they would like to try something and play it by ear though. It's near impossible for a DM to predict exactly how a group of players are going to react after all, as a result I tend to hand over almost total control to them when it comes to a tactical scenario and executing a plan. I will decide the best thing to roll on and sometimes simplify a sequence to just the one roll based on the actions they plan to take but they have their destiny in their hands. It sort of represents a highlight reel. A player doesn't need to spend too long actively calling for and taking extra rolls to find out lore information or something that they'll routinely be able to handle but they have near complete control when they're trying to pull something off on a more impulsive nature. I still won't allow the aforementioned "well X failed so I'll try it instead" circle though!
I'm in neither camp because some of them contradict or conflict within each of the choices.
I much prefer players to just tell me what they're rolling for, before they start rolling. I don't like being 'asked' because it slows down the game and it's just annoying to be a babysitter/gatekeeper. So you find some berries on a bush and say, "I'm rolling a nature check to see if I know what the berries are and if they're poisonous or not. I got... a 15," and then, I decide if a nature check is appropriate to identify the berries (perhaps they're entirely magically created and simply don't exist anywhere in nature, for instance), and if the check is good enough for any information, no information, misleading information, or highly detailed information.
Unfortunately most players seem really reluctant to do things this way so I often end up prompting before I realise I'm doing it, just because I get frustrated when the game slows to a crawl with nothing really happening.
"Most people are other people. Their thoughts are someone else's opinions, their lives a mimicry, their passions a quotation."
― Oscar Wilde.
Letting each player roll until one has a success is indeed obnoxious and slows things down to a crawl. If such a situation happens regularly things get out of hand. I just simply won't allow for anymore of such checks and only the ones with a trained skill in it is allowed to do so. Perhaps with advantage if another player helps out looking for something. Thankfully my players aren't like that and have settled into a flow where they know a bit of each other. They know who is better as certain things. Which results in one character asking another to keep their eyes out for something. Or they discuss in which order to go in a room and as such work together more often.
I'd say #2. If a skill check is called for, that's a DM thing.
PCs aren't aware of game mechanics, so asking a player to be responsible for adjudicating what skill is called for, when, is strange.
Plus, as a DM, I have access to the information that the player is asking for. If the player asks me what crest appears on the wizard's robe, I may very well answer "He is wearing the crest of the laughing coffin" and move on from there, short-cutting any need for any one to roll anything. The fact that I've already declared that the information is not immediately available to the player means that I've already decided to put that info behind a skill check wall. Making the player ask the same question multiple times to get a straight answer just seems pointless.
Im of the opinion that DM's should be asking for rolls and checks, this helps the flow of roleplay a lot because the players done need to be thinking 'im looking out so I need to roll perception!' its just 'im on guard looking out for enemies' then they are prompted by the DM.
In my opinion and experience it helps to cut down on the perception train that others have been talking about because you can get a list of what people are doing; ask the PC's what they are doing after a battle: 2 rummage through loot, 1 looks out for enemies and the other is trying to unlock a door moving forward. Once you get that list and idea you start doing rolls, 2 investigation, 1 perception and 1 thieves tools, that might prompt others to look out aswell realising there is one look out however most of the time it is done before. If it is a super low roll then I will go off passive perception of the other PCs!
The look out gets 3 on their roll but someone is sneaking up with a 8 stealth the others are going to realise them with their passive perception just glancing down the hallway etc.
Got proactive, experienced players who consistently tell you they're making the appropriate checks for the situation they're in? Don't prompt. Have players they never check, or try to handle animal their way past a group of guards or intimidate traps? Prompt.
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None of the above!
Wait...Both...um...
I actually use option number 3:
Don't worry about them, the answer is in the words the players use and their passives.
---
"You walk into the chamber, there's a pile of rubble directly in front of you. You look up and see the ceiling has collapsed here, a large boulder stuck in the hole like an over sized golf-ball. On the walls you see murals, hunters chasing down stags, dogs chasing foxes, pheasants in flight with arrows following. A statue of what looks like a half man, half wolf is displayed in the center of the room, almost as if it's honorific. You're guessing it's a werewolf, but it's odd to see one honored."
*DM steps over to a player and whispers in their ear and passes a note to a second player*
Whisper: "You notice the faint glint of a metallic wire extending out from the pile of rubble in both directions parallel to the door you're in".
Note: "You feel like you've heard of a lycanthrope cult, the name Malar is stuck in the back of your mind".
*DM sits back down*
"The rest of the room seems as though it used to have wooden benches as there are rotten planks scattered about the floor on either side of the room. The dust on the floor is thick, leaving you to believe it's been years since someone has been down here. Except the odd depressions that look very much like rat tracks and some sort of very large dog. Those tracks seem fresh, you're guessing weeks old at the most."
---
At this point in time I have looked at a post it note on my DM screen and saw that no one had a passive under 11, and there was one person who had a passive of 15. The person with the 15 was given the information about the wire. The Bard in the group got the note, simply because of the fact that stories are what bards do and remembering odd facts is natural. All of the other information is gleaned using every day common sense, normal experiences one might have, and the assumption that people can put information together without major leaps of logic.
Prompt:
Immediate threat or failure: Falling rocks, trying to look into the window of a passing carriage, reading lips.
No Prompt:
Action based threat or failure: checking for traps, trying to remember more than what was presented in a description, avoiding detection while sneaking around
Automatic information:
Anything that you could discern from spending a moment of looking around and using your grey matter. Common sense information based on any and all media, just because it's a movie to us doesn't mean it can't be a campfire story for them. All passive checks.
It should be clear that #1 is the wrong answer. You should never expect your players to be the sole arbiters of when an ability check is appropriate or to have the sole responsibility for determining the ability check they should make in a situation. They might sometimes request to make a specific check, and that is totally acceptable, but what you absolutely should not do is describe something (in vague terms no less) and then expect your players to figure out what ability check they need to make. If you're doing this, then you're 100% wrong.
To use an example from the original post:
If I had a DM that said this to me as a player, it would drive me insane. What does the phrase, "it's unclear whether you can tell from this distance" even mean? As a player, I wouldn't have know whether I was being told a Perception check was not possible here, not appropriate for some reason, not likely to succeed, or if the DM was simply expecting me to decide to do their job for them and figure out that a Perception check was required. This is not the correct way to DM. Please do not do this.
Otherwise, I don't think there's a right answer here. Perhaps the most natural approach is that the players describe their characters' actions and then the DM decides which ability check is appropriate. This also makes it much easier to decide when to apply advantage/disadvantage or other circumstantial bonuses, as these will be determined not just by what a character decides to do but how they decide to do it. But there are other scenarios where the DM should prompt the players to make a check, or where using a passive score is appropriate, or where players might request to make a particular check. These can all be decided on a case-by-case basis.
Several people mentioned cases where several players request to make the same check. There are cases where it makes sense to limit who can make a check based on proficiency or some other aspect of a situation, but in other cases, it's entirely acceptable and realistic that everyone will want to make a check. The "train" of one character asking to make a check, and then another, and then another, is a failure by the DM, not the players; you should be able to anticipate when all players will want to make a check (and when all characters are capable of doing so) and just prompt everyone to make this check from the get-go. If you create a scenario where all characters could attempt to do something, and then you only allow some characters to attempt it, then you've just decided to artificially limit the agency of the players and their characters.
Anyone who says anyone else's DMing style is wrong is wrong. With experienced enough players, you don't need to prompt. A group I'm running now has 3 players, all of them pros and veterans. I have yet to prompt a roll or tell them a roll isn't appropriate for their situation.
Ongoing Projects: The Mimic Book of Mimics :: SHARK WEEK
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I think you may have missed my point. The original poster phrased this an unequivocal statement. "DMs should never prompt their players for ability checks." This is categorically wrong, and it's not a question of DMing style. It is the DM's job to adjudicate ability checks, as with all other rules of the game.
But the caveat is, as you've noted, only when it's required. You're lucky to have players who are experienced enough to not require prompting and who have a very good sense of what ability checks are appropriate for a situation. If players want to be proactive and request to make specific ability checks, more power to them. But this is not true of all players, or even of most players, and the fact remains that you can't expect players to bear this responsibility.
If a DM describes a situation, and the players know what they want to do but are completely unsure of what type of ability check they should make, the DM shouldn't just wait for the players to figure it out.