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What can we either as players or as characters do to be more careful about investigation and reconnaissance without making things slow and boring?

As a party we tend to make poor tactical decisions. One time we didn't set a watch in what should have been obvious as a dangerous situation and we went from asleep to teleporting out barely alive in 5 rounds. Another time we entered a village that we should have been suspicious of and 3 rounds later there's blasted Mind Flayer everywhere and two of our party members have been taken over by Intellect Devourers and have vanished.

However, as a party when we do engage in investigation and reconnaissance, we often spend way too much time discussing it, it is not particularly productive, and we use up a lot of time in ways that aren't interesting or are even boring.

As a group we feel like the game is not as fun as it ought to be because when we carefully investigate it's boring, but when we don't, encounters go sideways and characters are incapacitated and perhaps killed, and we are being set way back in making progress on our goals.

We have had some good discussions about the problem:

  • Missing clues. One concern is that the GM is giving clues that we are missing. We've discussed it and things that the GM thinks are obvious some of us are missing. For instance, from the GM's point of view, the Mind Flayer village was obviously a dangerous trap and we weren't paying attention. We had a good discussion and we the player are going to try to be more mindful, and The GM has agreed to hit us harder with the clue stick.

  • Recon is boring. Some of the players expressly feel being ultra careful is boring, for instance, if every step of the way you check everything for traps the game just devolves into boring trap-checking. We think there should be a healthy balance between tedious paranoia and reckless abandon, but struggle to find it.

  • Recon is unbalanced. As the party wizard, my character is well-equipped for magical recon, with a familiar, arcane eye and other scrying spells, but we don't do much because then my character ends up hogging the limelight. We've talked this over, but haven't really come to much of a conclusion yet.

  • We have no party leader. We think that maybe indecision contributes to taking too long to make decisions, or failing to make them, which leads to overlooking things that are obvious in hindsight, for instance, setting watch. We've discussed having a party leader, probably rotating it, with the idea that, at least tactically, one character would be the decision maker, not coming up with all the ideas, but being responsible for keeping us moving forward. (Typically), we've discussed this but haven't come to a decision, although we might be getting there.

  • Deadly encounters. We've had a lively discussion about the deadliness of encounters. The GM says if you make camp in an obviously hostile location and a monster that is probably unbeatable comes along and you flee for your lives, well you brought it on yourselves. The party has mixed feelings. Some think the encounters are too deadly, others think not. I really think this is a symptom, not a cause. In each case where things have gone pear-shaped it's been clear in hindsight what the mistakes were, and often we'll say to each other, "yeah, I knew that wasn't going to work out", but we did it anyway. Maybe the PCs are deadier to the PCs than the monsters are.

If it's important, the whole party is 14th level, usually with about six characters. The game is fairly high magic and a good bit of homebrew. Probably party level and composition isn't significant one way or another, although perhaps the challenges encountered at higher levels are exacerbating a problem that's been there all along.

We play voice over Discord using D&D Beyond. We are pretty experienced at RPGs and D&D 5e in particular. We struggle at times with some members being on cell phone and sometimes typing instead of talking. This might be a factor in missing clues. I am less concerned about the technology. We have recognized that this occasionally causes communications issues and we're working together to mitigate this.

So here is my question:

What can we either as players or as characters do to be more careful about investigation and reconnaissance without making things slow and boring?

Although GM advice is welcome, I'm mainly asking from the players' perspective. The GM has agreed to be more obvious about the clues and has been very proactive in fostering after-session discussion.

What are we missing? What has worked for you?

I have some concern that this question may invite bad-subjective answers, and possibly closure as opinion-based. To that end I will say I am looking for answers that:

  • Is based on what worked or didn't work for you based on personal experience and/or
  • Something you can back up with a reference
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  • \$\begingroup\$ Is your DM aware of passive perception scores? Maybe your party (in game) realizes their inattentiveness and goes on a (1 or 2 session) quest to find some artifact that boosts their score or "auto scouts" (in a nerved way) \$\endgroup\$
    – Hobbamok
    Commented Apr 20, 2022 at 10:20
  • \$\begingroup\$ Are you sure your group just doesn't like high-level play? D&D encounters at high levels (especially with high magic) are routinely brutal if your GM runs opponents as if they used their intelligence scores fully. Retire those demigods, roll up a zany batch of noobs and go have fun again \$\endgroup\$
    – Gus
    Commented Apr 20, 2022 at 14:47
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    \$\begingroup\$ @Gus Actually we love the high-level play and want to drive it higher. We don't mind the instantly deadly encounters (tbh there are mixed feelings), we don't like getting smacked around, and so some players whinexxxx express concern, but admit that in other circumstances where we were smart, they loved the tough encounters. What we mind is that we self-induce poor outcomes in the deadly encounters. We should have got the drop on the mind flayer, instead it got the drop on us. We are individually smart, collectively dumb. We don't want to play a different game, we want to play this one better. \$\endgroup\$
    – Jack
    Commented Apr 20, 2022 at 14:51
  • \$\begingroup\$ Don't you think the vital point there is "as we ought to…" and that that is quite separate from anything taking too long, or being boring? What you could do differently would most obviously include redefining investigation and reconnaissance… In your game, what powers and what limits are there for investigation and reconnaissance? \$\endgroup\$ Commented Apr 23, 2022 at 22:36
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    \$\begingroup\$ @RobbieGoodwin Thanks for your feedback. I'm reluctant to significantly re-write the question. That it's received 34 upvotes suggests that something in the question is resonating with readers. I may write a new similar one and if I do, I'll take your feedback into consideration. \$\endgroup\$
    – Jack
    Commented Apr 24, 2022 at 16:03

6 Answers 6

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Sounds like your DM isn't communicating dangers effectively.

It sounds like the problem is this: The DM is creating dangers, but leaving it up to the PCs to proactively investigate in order to discover the dangers. The players are responding by being overly cautious for fear of hidden danger.

Making the dangers non-obvious turns them into a kind of secret or puzzle. That means the players can miss the solution entirely. It can be a fun mode of play, if the players are the pro-active sort, and enjoy winning by their own wits. However, not all groups enjoy this mode of play. Combine non-obvious dangers with high lethality, and you have players who are hesitant to do anything.

An adventure that relies on uncovering information for success is similar to another tried and tested model: the mystery or investigation adventure (e.g. a murder mystery). The best approach to investigation adventure design is to have multiple ways to discover each piece of key information. Clues lead to other clues. The DM should consider letting player suggestions work even if it wasn't in their orginal plan. If the DM has only one way to uncover each piece of important information, it ends up like one of those old point-and-click adventure games where each puzzle has one specific solution that's obvious to the game's writer but not to the player.

In my experience, this suggests the DM should be more proactive in presenting dangers, and should probably pivot away from encounters that rely on the players detecting danger ahead of time in order to be successful or safe. That mode of play seems to be not working for your players. The DM may want to shift to more obvious encounters (e.g. dungeon crawl type adventures) or scenarios where failing to find information doesn't kill the party (e.g. investigation adventures where you need to acquire information to progress, but there are many ways to acquire that information, and failing doesn't harm you, but merely serves as a puzzle, and the existence of the puzzle is clear, so the focus of the gameplay becomes everyone working together trying to find a solution to the puzzle).

Perhaps the players can institute standing orders.

In olden D&D when the game was somewhat more deadly, players would sometimes instruct the DM ahead of time to assume they were always using a ten-foot pole to check for pit traps, always moving stealthily, always searching for hidden doors, always having someone watch the party's rear, etc. This would both improve the group's confidence and save the players time.

You might institute standard orders like "assume we always scry on a new town before entering it", "assume we're always being stealthy", etc. The DM can prepare for that and very quickly hand you the answers or let you avoid dangers.

If I were DM I might also very quickly sum all the party's paranoia up in one Investigation roll each or something, although of course this is something you hae to ask the DM if he'll allow you to do.

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    \$\begingroup\$ How would one broach this subject with the DM without making them feel attacked for how they are running the game? \$\endgroup\$
    – NotArch
    Commented Apr 18, 2022 at 10:26
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    \$\begingroup\$ We've talked this out. We have a discussion after every game, and we frequently have at least occasional discussions throughout the week. Last week we had a very good discussion which kept me up way too late and as I said in the question, "the DM agreed The GM has agreed to hit us harder with the clue stick." That might be PART of the problem, but what I'm trying to drive in the question is, "how can we be careful without it being boring"? \$\endgroup\$
    – Jack
    Commented Apr 18, 2022 at 13:03
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    \$\begingroup\$ @Jack To help with the GM side of the problem, we have a question on the stack regarding this problem from the GM side of things. Each of the top 3 answers has good feedback on what the GM can do differently, which is more specific than just hitting you harder with the clue stick: rpg.stackexchange.com/q/112915/15991 \$\endgroup\$ Commented Apr 19, 2022 at 12:59
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    \$\begingroup\$ @Quadratic I like the standing orders. I can even implement a version of that without any GM agreement, just make a list and say it a lot. \$\endgroup\$
    – Jack
    Commented Apr 19, 2022 at 17:54
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    \$\begingroup\$ A slight variation is to make encounters easier if the secret is found, but beatable either way (even if just barely so). Missing the clues means you'll require more consumables/rest/etc. but you're not instantly doomed because you didn't read that one sign. That way you only get catastrophic results when you have multiple mistakes compounding on each other (e.g.: you let the enemy sneak up on you and you forgot to bring the talisman that would repel them). \$\endgroup\$
    – bta
    Commented Apr 20, 2022 at 20:30
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It's not panacea, but do recon offline

Our party is pretty close to what you describe, and so are our experiences. I'm the party wizard, like you, and like you have arcane eye.

I've taken to do sessions outside of the main session with the DM, to scout the map with arcane eye (or clairvoiance, or scrying, or an invisible long-range telepathic contact gazer familiar), note my observations, and then relay this to the party in game as needed.

This has two advantages:

  1. It does not hog the limelight during shared play time
  2. It plays more like it would in the game world: the others do not see what I see, and only experience it through my narrative, which both plays more like the wizard with access to forbidden knowledge, and suffers from me sometimes forgetting stuff I saw.

Clearly this does not solve all the issues, but in our case it helped at least alleviate the pre-recon part.

As a group we preferably stick to areas we have already screened like that, which avoids a lot of the other gotcha-situations. It's not foolproof, as well-hidden, false-appreance, invisible or ethereal traps and enemies still can get you, but it improves the odds quite a bit.

For example, if we are on a dungeon level we have screened, and discover a secret door leading to stairs down, we continue to explore the current, screened level. When we rest I'll let the DM know I'm casting divination spells to check the next level, but we do not play it out at that time, we continue play on the current level. Then I play them out with the DM between sessions, and when we play next time, we know what could be waiting for us, and might go down.

I tend to enjoy these mapping sessions, but even if you don’t, at least they are not boring for all of you, just for the caster who runs them.

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    \$\begingroup\$ Wow, that is definitely out-of-the-box, thanks. How are you maintaining telepathic contact with your gazer familiar? \$\endgroup\$
    – Jack
    Commented Apr 17, 2022 at 21:20
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    \$\begingroup\$ How have you gotten player buy-in/availability for offline? How does offline work for something that's happening now in game time? I think I may be misunderstanding this answer. \$\endgroup\$
    – NotArch
    Commented Apr 18, 2022 at 10:24
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    \$\begingroup\$ @NautArch, we commonly only do this for arcane eye type recon, to avoid having everybody sitting around and only being able to listen. In our group, I am the only one who has access to such spells, so it doesn't come up for the others. We do not generally run side 1-on-1s, although the DM does them on occasion, like when opponents or events catch one of us who is off by themselves shopping or something like that. You can often just mark during play "I'll do arcane eye on the next level we discoverd this night", and continue playing (exploring the current level or such), then do it later. \$\endgroup\$ Commented Apr 18, 2022 at 10:40
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    \$\begingroup\$ @NautArch It has worked out very well for us, we have avoided tons of sticky situations this way. It's just is not a formulaic, foolproof solution, which I think is as it should be. I did add a bit of text explaining in which situations it will fall short. \$\endgroup\$ Commented Apr 18, 2022 at 11:31
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    \$\begingroup\$ I feel like maybe my question isn't clear. This is absolutely self-induced. "Being as careful as we ought to be takes too long and is boring", and then bam! it's a mind flayer and its swarm of intellect devourers. We were in underground caverns in an area where no one ever goes because monsters! There was a cute little village! There were clues! We walked in anyway! \$\endgroup\$
    – Jack
    Commented Apr 18, 2022 at 11:51
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There are a few things you can do:

1. Level the playing field

Part of the problem seems to be technology; different people accessing in different formats/media. I played in a game with a similar issue; we used Roll20 for the VTT and Discord to talk. Except one person could not handle both on their machine (Discord would drop while action was happening on screen). So they resolved to just typing in Roll20 chat. But that meant in the heat of things, we'd have to wait while this other player typed out their message, if they had a message at all. It kept grinding things to a halt. To get around it, we all pitched in and bought a cheap pay-as-you-go phone that would handle Discord while the computer ran Roll20. With everyone communicating in the same way, we got more done.

In your case, I think it is more a matter of just finding one chat client and sticking to it. Find something that everyone can handle and live with; Google Meet, Discord, Zoom, or some other party line. And friends don't let friends don't roll and drive.

2. Predetermine your load-outs

And by that I mean, have a set standard for a number of routine operations. In one campaign, we created a sheet that showed all of our standard formations: single file, side-by-side, protect one character, protect two characters, wall, etc. By having this all done ahead of time, it cut down on the "what's your marching order?" and "where is everyone standing?" You could even go so far as to say, "In single file, character a is always searching forward for traps, and character z is watching our back." Now the DM can just talk quickly to two players and ask for perception checks.

You can take this farther with Standard Operating Procedure (SOP) for other thing:

  • camping for the night (watch/no-watch and order of watch),
  • recon (if character A they use arcane eye, if character B they use stealth, if character C they use an invisible familiar)
  • and any other oft-repeated duty

By setting these up ahead of time, you reduce waste in saying the same thing over again. It will also work as a good reminder to do certain actions. You have a role-call for watch, USE IT. You can also bullet through some sections as everyone knows their role. It also dims the spot light as the DM now only needs to handle things that aren't covered.

This might also reduce the need for a "leader" in the group. With these decisions made ahead of time (out of game) there is less opportunities for people to sit around waiting for someone else to choose a plan of action.

3. Give feedback

The DM and players should talk out of game about what went well and what didn't go so well. You can have "Session Zero" talks more than once. Work with each other to find out why you're not getting the clues. Maybe they need to be more obvious. Or maybe there should be more than one clue. Maybe the characters get the clue, but don't act on them in a timely manner.

Which leads into...

4. Face the consequences

If the characters walk into a dangerous area, it's on them to be cautious. If it looks like a dragon's lair, then don't make loud noises. If you enter a town where everyone is dead, ponder if the perpetrator is still around.

Do not assume that the DM will only run hard encounters right after a good night's rest. At level 14, your party has many avenues for being safe. From tiny hut to private sanctum to word of recall and teleport back.

This mostly boils down to communication issues; both the medium and what is and is not being said

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  • \$\begingroup\$ Thanks for your answer, I particularly like #2. \$\endgroup\$
    – Jack
    Commented Apr 18, 2022 at 10:29
  • \$\begingroup\$ #2 is what I was looking for before writing my own answer. Standard Operating Procedure goes a long way and the players can alter it at any time. \$\endgroup\$
    – goodguy5
    Commented Apr 19, 2022 at 13:10
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From what your are describing the situation can be summarised as follows:

  1. Your current style of play, being careful feels long and boring to you.
  2. Not being as careful usually goes sideways and Is punished heavily.
  3. GM and the group have different views on the enjoyment of the game.
  4. Some technical limitations may make matters worse.

I’ll start from the end. Sort out the technical issues first. Agree on a certain level of quality for your games, ideally by being all in discord with a proper connection, no background noise and distraction free environment. If that’s not possible at least make it so that everyone is under the same conditions, it is not fun to mix voice for 4 people and chat for two or to have someone be driving while playing (not to mention it could be dangerous).

Second, assuming that won’t solve your issue, go back to session 0 and find out what you as players and the GM define by “fun” in the context of the adventure. The GM controls the world, if it feels like when you are not careful and do tons of recon and preparation you always get punished that’s because the GM has decided that’s the kind of world you live in. However that obviously is not fun. An option may be for the GM being more forgiving about your lack of recon and punishing you in other ways. Maybe that trap you failed to account for destroyed precious magic items or you manage to just hold it together on that damn town but you lose all your gold.

Having the conversation is, to me, the second thing to do. And although you mention having had it, I think you each focused on what each of you can do to keep the current style of game going, I suggest you explore changing the style of game.

The third option is to inspire youselves on the benny system on savage worlds or the fate points on Fate or the inspiration points on DND itself. Agree with the GM on a certain number of “get yourself out of jail for free” events. Make it part of the economy so that deciding when to use them and when not to is fun in itself. This may be tricky (finding the right balance), but experiment with it.

I’ve managed the first two personally as a GM. With the 3rd on your particular situation I have no experience but I have experience with bennies and inspiration so I’ll make a suggestion: give one of the players at random one epic inspiration point every two or three sessions. This will enable that player to invoke a deux exmachina event decided by the GM but which will enable the group to likely survive the mess with only minor consequences. Note this is due to the fact that you are explicitly saying the consequences of not doing recon are way to big (go back to section 2 of this answer though).

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  • \$\begingroup\$ Thanks for your answer, there are some good thoughts in there. \$\endgroup\$
    – Jack
    Commented Apr 18, 2022 at 21:49
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    \$\begingroup\$ This is the winner. The core problem is that the DM is presenting an environment that is basically a high-fidelity simulation, while the players are discovering that coping with the simulation is tedious and un-fun. This is what happens when the DM is aiming for "Skyrim done with pen & paper." It can be hard to break out of that mindset. (Especially if the DM is actually playing Skyrim the other 6 nights of the week.) \$\endgroup\$
    – Tom
    Commented Apr 19, 2022 at 2:57
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Your group needs to come to an agreement about what makes a fun game.

There are some players/DMs who view D&D as a realistic simulation, looking for the natural progression of events. If you don't set a watch, you may be ambushed during the night and at a lethal disadvantage. You may run into encounters where you are entirely overmatched while not being aware of it. This is a perfectly fine playstyle.

There are some players/DMs who view D&D as a heroic simulation, akin to a movie or high fantasy novel. If you don't set a watch, there may be an ambush during the night but you're not at any particular disadvantage. You may run into encounters where you are entirely overmatched but will be specifically aware of it. This is also a perfectly fine playstyle.

The goal of the game is to have fun.

Your DM seems to be of the first mindset, whereas the rest of you seem to be of the second. You need to come to an agreement somewhere in the middle, where everyone is enjoying what is going on.

Assuming your DM cares about your enjoyment of the game at all[1], they are undoubtedly having similar concerns about the game -- wanting you to notice the clues, wanting you to make more tactical decisions, etc. It's not fair for their enjoyment to be disregarded, just like it's not fair for your enjoyment to be disregarded.

Actual advice

Most of this requires full DM buy-in; player specific advice follows afterwards because it builds on these items. These all come from my experience in running a number of games (not just D&D). In particular, the philosophy of Dungeon World is strongly represented here.

One note is that absolutely none of this is specific to reconnaissance, and can and should be applied much more generally.

The DM should give more/easier clues. There are a number of well written articles on this, such as The Three Clue Rule, Tips For Creating Good Clues, or Designing A Mystery for DnD, but the general gist is:

  • For any given piece of information, there should be multiple (at least three) clues for it. If there is a secret cult in town, there should be at least three clues that might clue you in (as examples, rumors in town about disappearances, cultist villagers using secret signs or having marks, and encountering cultist villagers in the woods with no good reason to be there). If the party needs to find the secret cult's headquarters, that should have at least three other clues (interrogating a captured cultist, following a cultist, or having a villager that has seen strange things). Every step should have multiple possibilities that lead to the next step.
  • The DM should calibrate the clues according to the players. Since the DM knows what is going on, many things will be obvious to them that simply are not obvious to the players. Perhaps the DM is using tropes that they expect to be common sense that the players are unfamiliar with. Perhaps the DM is expecting more abstract leaps from the players then the players actually make. But if all of the DM's clues are missed, and this happens repeatedly, the DM needs to consciously make the clues easier to get, no matter how hand-holdy it seems to them.

Players should be prompted for interesting choices, and non-interesting choices should be assumed to be automatic. Take setting a watch: in D&D, there is usually no reason to not set a watch (you don't suffer exhaustion, still receive a long rest, etc), so this shouldn't even be a choice -- your characters are 14th level, and presumably extremely competent, adventurers. Unless there's a reason to not set a watch, it should just be assumed they do so. After all, it is incredibly unlikely you are expected to say things like "I clean and oil my armor" or "I sharpen my sword"; it's just assumed that such things are done.

Similarly, if a rogue or someone else skilled in detecting traps is going down a hallway, if there is no reason for them to not check for traps, they should be assumed to be doing so.

Now, perhaps there is something that makes the choice interesting -- "Are you running down the hall to put distance between you and the orcs, or are you taking it slow and steady to look for traps?" is interesting. "You're all exhausted. Anyone who keeps watch will remain exhausted. Are you going to keep watch?"[2] is interesting.

It is best if these choices are explicitly understood by everyone involved: "when we sleep, we keep these watches," "when the rogue scouts, they check for traps", "when we're not under time pressure we search all rooms," but the DM should give the benefit of the doubt to the party that they are competent and automatically do competent things unless there's a reason otherwise.

Parts of the game that focus on a single player should be minimized. This is a group game, after all, and if a majority of the group is not involved it is probably not enjoyable for them.

Whether or not your wizard casts arcane eye or use a familiar are interesting choices (arcane eye burns a spell slot, the familiar may be killed), but the details of the scouting itself aren't particularly interesting. If the arcane eye maps out the entire dungeon / lair / fortress, then that information can simply be provided; there's no reason to make you, the player, say "I check the next room. I check the next room. I check the room through the right door. I go back and check the room through the left door. I investigate the chest. I investigate the desk. I check the next room" if there's nothing that can interrupt the process. The DM can just give you -- and the rest of the party -- the information and get on with the group portion of the game.

Now, maybe there is something that can interrupt the flow -- then it becomes interesting. But even then it can be minimized -- "the archer sees your owl and shoots it dead," or "the wizard notices your arcane eye, and with dispels it, but now they're aware of the party's presence"

The lethality of consequences should be toned down or the consequences should be made incredibly obvious. Analysis paralysis and the like is due to the belief that if the wrong decision is made, the consequences will be drastic, necessitating spending a lot of time making the right decision.

Analysis paralysis is typically boring for everyone involved, so should be minimized unless the consequences are drastic, in which case it is more or less warranted.

This can be done in one of two ways:

  • Making the consequences less drastic. There will be less analysis paralysis if the consequences are not crippling. Starting a party-level-appropriate combat is much less dire than a CR 20 combat (or one where a group of eight mind flayers gets a surprise round) that can potentially wipe the entire party.
  • If the consequences are drastic, they should be explicitly communicated to the players. "If you scout the wizard's tower, you can learn the layout but may lose the element of surprise." "If the dragon wakes up while you're carting out its treasure, it's very likely to eat you." "There is an aura of palpable dread surrounding the Ancient Artifact of Doom, and the lich will know when it is moved. Are you sure you want to pick it up?"

The goal should be to both not spend time on small decisions, and to have the information needed to make important decisions. You may still make decisions that you regret, of course, but you'll be making them aware of the consequences, instead of having to worry about the dozen possibilities, eleven of which are not actually going to happen.

(As previously discussed, if there's one path that is consequence free and no reason for the party to take another path, then the decision should just be assumed.)

Player specific advice

This builds off of the previous section, and are things that you can do without complete DM buy-in -- most of them are essentially prompting the DM to do things that they should otherwise be doing. They do require you to be proactive in your statements, however, so there might be a learning curve in terms of when or what you need to prompt the DM for.

State actions that you take automatically. "We always set a watch unless there's a reason not to. We always check for traps unless there's a reason not to. We always search rooms unless there's a reason not to." If necessary, type it out and pin it in your discord channel or equivalent.

If new situations come up that you don't have automatic actions for, and they seem in general to have one superior choice, then add them to the list going forward.

If the DM complains, you can maliciously comply[3] by asking "What are the consequences of not setting a watch?", and upon learning that there are none, saying "We set a watch," but if it takes more than two or three times then there is a larger disconnect.

Ask the DM broad questions for information that your character would be able to determine. This one is difficult because it requires you to be proactive about what you need to ask, but things like "Where is the best place to set an ambush along the trail?", "What are the ways we can sneak into the castle?", or "As a competent adventurer, what are we missing?" It's the DM's job to convey the information of the world to you, and your characters are hopefully competent in setting up ambushes/sneaking into castles/knowing what competent adventurers do, so leverage that.

The goal with these questions is to narrow down a wide set of hypothetical possibilities into just a few paths that the DM has classified as important. Making the questions broad is to avoid asking the same question repeatedly about different subjects.

If the DM is hesitant to give such information (either because they see it as hand-holdy, or because they value player input on path choosing more than you do), then most can be rephrased in the form of an action: "I scout the best place to set an ambush along the trail," "I case the castle for ways in," or "I go through memories of former adventures looking for similarities to this situation."

State broad or general actions. Not "we search the desk" but "we search the entire room." Not "we talk to the drunk at the inn" but "we talk to the villagers." Not "I scout this room with arcane eye" but "I scout the tower with arcane eye."

The goal is to avoid tediousness of saying the same thing over and over, but specifically to avoid the instance of "You said you searched the dresser and the bed, but not the desk, so you didn't find the key." Again, you can maliciously comply[3] if the DM objects by asking "What are all of the objects in the room?" followed by "I search the desk," "I search the rug," "I search the torch," but if this takes more than two or three times there's a disconnect. If there is an actual consequence, the DM will be sure to let you know when you trigger it.

Ask for the consequences. Again, slightly difficult as it requires you to be proactive, but if the group is dithering between two or three actions, ask the DM what the possible consequence of each one is.

If the DM refuses to say, either continue to dither until the DM is bored, or state your opinion and that you're going to read stackexchange until an agreement is made[3] and to let you know when that happens.

Inform the group when you are not having fun. Though the "going to read stackexchange" statement above is facetious, stating when you are not having fun is not. State when you are not having fun, and ask if anyone (including the DM) is. That is, literally asking "I'm not enjoying this. Is anyone enjoying this?" If no one is having fun, then move on to something that is fun.

If multiple players are having fun, it's probably best to let them (their enjoyment is important, too), but you can still indicate your dropping out of the current situation: "We've been talking about this for ten minutes and don't seem to be making progress. I've stated my position, so I'm going to stay silent until a decision is made." If this goes on for a significant time, then indicate your attention is going elsewhere and ask to be pinged when the situation moves on or your involvement is needed.

An alternative is if the DM is having fun, but no player is, to propose a method to easily resolve the conversation: "We've been talking about this for ten minutes and we're deadlocked. Can we just flip a coin and move on?"

[1] If the DM does not care about your enjoyment as players of the game, that is a separate problem.

[2] I understand this is not a standard rule in D&D, and it is presented simply as an easily-understood example.

[3] The malicious compliance is not actually recommended, but more of a facetious take on why this advice is being given, and what following it avoids.

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    \$\begingroup\$ Thanks! The player-directed portion of what you wrote is pretty good, I will carefully review and keep in mind. (Your DM-directed portion is reasonable, too, but secondary.) Thanks again! \$\endgroup\$
    – Jack
    Commented Apr 19, 2022 at 19:12
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It sounds like the players and the DM have differing opinions on how the game should be played.

It's a fairly common problem in gaming groups - in this instance, your DM seems keen on setting up traps to trip characters up, and your group seems to feel that spending all that time on recon and picking through DM details is boring.

Your group needs to talk about this together - outside of the game itself. And you need to come up with a compromise on how the game should be played.

This type of discussion is usually called Session Zero, but in your case it may be prudent to go over the group dynamics regardless of session number.

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    \$\begingroup\$ Usually pointing a user to session zero is only the beginning of an answer, and as the entirety of the answer it's not great because there's very little advice specific to their situation. Ideally answers should suggest specific changes the DM and/or players could make, specific conversations they should make a point of having about the game (whether during a session zero or not), or so on. Consider for example that if “have you tried having a session zero?” was a good answer to social questions, almost all our social questions would share identical answers. We need to do more than that. \$\endgroup\$ Commented Apr 18, 2022 at 13:39
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    \$\begingroup\$ So, I tried hard to convey in my question that we've actually had multiple discussions. We talk really well after the session, sometimes before, sometimes during the week. While there is SOME disagreement about deadliness, there's no disagreement that we the characters made serious tactical errors that we shouldn't have made. So, my question isn't really about playstyle or communications, it is "What can we either as players or as characters do to be more careful about investigation and reconnaissance without making things slow and boring?" That's my question. \$\endgroup\$
    – Jack
    Commented Apr 18, 2022 at 21:47

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