My players got themselves into a diplomatic problem that they know is probably above their pay grade in terms of difficulty. They spent a session trying to figure out this problem by talking to people, and rolling different Charisma checks in order to try to persuade people they probably had no business persuading (rolls were average, arguments weren't extremely compelling). The party didn't plan any grand schemes, any extraordinary strategies, no clever ideas on the spot, but rather tried very basic head first dialogue.

This has happened in the past in regards to combat. The party has (with a recent deadly encounter) had to think out of the box more (one player even said: "guys we need to plan more and think less about just hacking and slashing sometimes"). Now it's a more diplomatic problem that doesn't seem as easy as rolling a single Charisma check and hoping it works out.

In the end, the party did not manage to solve the diplomatic problem (although there is room in the future for them to try again with the upper hand), and one of the players said that they did not enjoy the session. Player enjoyment is my top priority. But I also think D&D is best when there's risk, when you can fail rolls, when the PCs don't always win (not that I actively seek this out though).

How can I get the party to perform less linearly in dialogue-related problems?

An example problem at our table:

Problem: If trying to outsmart a bad person with a lot of influence in the town

Answer: There are options for framing the person, bribing people, seeking dirt on this person to find their weakness, tarnishing their reputation, trying to prove their wrong doing by seeking out evidence, and a bunch of other possibilities.

I've tried to have a brief session-0 talk again about if they want dialogue-related problems handicapped, and they didn't seem to take to that, but rather felt like they tried everything and didn't know what else to do. I also did a postmortem on this problem and tried to give different options they could have tried, but I get a feeling the players feel like they still tried everything and failed and the session was "a waste" (even though they still got XP, still got some loot, and got some more plot).

I'm kind of at a loss of how to tackle this issue that isn't just: "Go watch some D&D podcasts to get ideas, or go read X, Y, and Z resource on the subject".

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    \$\begingroup\$ Are your players smarter, more charismatic, more genre savvy, and/or more practiced at diplomacy, bribery, blackmail, or criminal investigation than their characters? \$\endgroup\$ Commented Mar 29, 2020 at 18:13
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    \$\begingroup\$ "The party didn't plan any grand schemes, any extraordinary strategies, no clever ideas on the spot" - can you think up grand schemes and extraordinary strategies on the spot, without knowing the situation ahead of time? Characters in books/movies do this because the writers have as much time as they need. NPCs in game have an easier time doing this because the GM knows the situation and all relevant facts ahead of time. Players have neither advantage. \$\endgroup\$
    – Errorsatz
    Commented Jul 21, 2021 at 21:45

4 Answers 4


A: There are options for framing the person, bribing people, seeking dirt on this person to find their weakness, tarnishing their reputation, trying to prove their wrong doing by seeking out evidence, and a bunch of other possibilities.

Did you tell them this?

Did you tell them the pros and cons of each option?

I don’t (necessarily) mean straight out enumerating the options you see (although I have done this) but you need to have scenes where these clues (at least three for each option) get from your head to their head.

Role playing is about making choices but you, the DM, are the source of all knowledge in the world and what’s obvious to you is never obvious on the other side of the screen.

Players that are throwing out imaginative ideas and making progress are having fun. Players who are going around in circles and not making progress aren’t. From time to time part of the fun of DMing is schadenfreude but it’s best in small doses.

When they get stuck - give them a push.

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    \$\begingroup\$ I did tell them this after the fact, but maybe I need to be more helpful during the situation like you mentioned. I feel like it's cheating / unwanted to help them during a problem, but maybe as you mentioned it's better to offer suggestions in the form of more clues so they have more options available to them. \$\endgroup\$
    – Ray C
    Commented Mar 26, 2020 at 13:04
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    \$\begingroup\$ @jay it helps to think of hints as you helping the players understand what their characters know but they don't. Most people in real life don't do blackmail or dig dirt on people, so it's not always obvious \$\endgroup\$
    – SeriousBri
    Commented Mar 26, 2020 at 15:23
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    \$\begingroup\$ @Jay but maybe I need to be more helpful during the situation Bingo - Dale's link to the three clue rule will hopefully offer a good resource. \$\endgroup\$ Commented Mar 26, 2020 at 15:30
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    \$\begingroup\$ @Jay “Player enjoyment is my top priority. “ and “I feel like it's cheating” See that? So, is "not cheating" more important then? No? Then cheat it up! (Just... don't make it look like you're cheating... have the beggar on the street corner go "hah... I've been watching you and you guys are so dumb... you should just...") \$\endgroup\$ Commented Mar 26, 2020 at 16:10
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    \$\begingroup\$ @Jay I find it best to assist the players showing what they're capable of before expecting them to do it on their own. If you want the players to bribe or frame people, give them a short quest where they have to frame someone for a crime and bribe a judge. Giving them an on-rails experience with this interaction lets the players know how to do this in- and out-of-character. \$\endgroup\$
    – JRodge01
    Commented Mar 27, 2020 at 12:16

Make sure everyone at the table is playing the same game

The very first thing that strikes me is that you want to run a political intrigue mission while they want to just roll dice without necessarily thinking too deeply about their choices.

These are two playstyles that are at odds with each other. Based on this and the linked questions, they want to play a hack and slash. If that is their taste, that is perfectly fine. There's nothing wrong with just wanting to swing your sword. The question is, are you willing to run that?

Evaluate your campaign if it has these elements

The following advice rests on the fact that your players have agreed that they want to play the game you want to run, which is a campaign where challenges are not straightforward, and creativity is a requirement.

Do your Player Characters have any motivations?

Everyone in an engaging and exciting narrative has something they want, but they can't have. They are driven to gain that thing, whatever it is, and that fuels them so that they can drive the story forward in turn. Do your player characters have them? And if they do, are they cool, genuinely engaging motivations?

It's not enough to say "my character is an orphan and he wants revenge on his parents' murderers." I mean, that's actually a fantastic motivation, but it should have more detail than that, and the details should be the kind of things that your players are excited about.

What about: "my character is an orphan because my parents owed Torbor Longbeard money, and when they couldn't pay up, he tried to take our house and everything we owned, but they tried to fight back."

Or what about: "my character is an orphan because I poisoned them to inherit the throne, but Lilian Stormwell discovered my plot and exposed me, so now I want to get her back."

I once ran a game for someone who suffered from a chronic disease, and he basically couldn't do a lot of things by himself. So his one fantasy was to be a noble, honorable, capable, handsome, and well-respected general. And you know how he reacted when I let him have that fantasy? He became very engaged in the story. He tried to solve every problem I threw his way no matter how hard it was. He bought into the fiction completely, and whenever he couldn't solve a problem, he would get frustrated, but he had fun regardless. He didn't blame me. He would tell me at the end of the game how much fun that was.

Get your PCs some motivation. If they don't have any, brainstorm with them. This is step one.

Are your Player Characters' motivations grounded in your fiction?

Simply getting your players to have characters motivated to do something is not enough. You might have a character whose motivation is to sleep with every woman in the world, and that's a valid motivation - but they would be out of place in a campaign about rallying the Forces of Light to defeat the Dark Lord, maybe except as the designated comic relief.

You want to tell a story. So you decide on what that story is, who are the main movers and shakers within in, and tie your player characters into it. They don't have to be central to your main plot, but they have to match the tone you're going for.

If you're running a political intrigue campaign, then their motivations should be somewhere that it won't take more than one step for you to connect them to the story you want to tell.

If your campaign doesn't have a backbone plot, if it's not about something, then work on adding one in. How can you ask your players to put in the work when you haven't done so yourself?

Additionally, make sure your player characters are themselves grounded in the world. It's so easy to make an orphan who comes from a town they destroyed because then you don't have to write anything substantial. You become a drifter in the plot, floating along with the tides but with no real stakes and no connection to anything.

Give them a mentor, wife, child, sibling, or - yes! - even a parent that they care about. If possible, align this anchor with who your players are in the real world, so that they can more easily slip into the fiction of becoming the character they're playing at the table.

Anchor your player characters and your players to your fiction. This is step two.

Did you make failure interesting in your puzzles?

Simply including a chance of failure in a task doesn't make it fun by itself. You can, in fact, create an entire puzzle that's impossible to fail, but twist it so that the win is still engaging. You can make a challenge complex but without depth, and then it would still be boring.

Do the characters have something to lose if they fail? What are the stakes? It sounds like though the players failed, you still rewarded them with a lot of stuff. So what does it matter if they couldn't solve it? It feels like an artificial wall that the DM is putting in their way. It doesn't feel like they failed, but it feels like you want them to step to the left, turn around, jump on one leg, and press X before letting them through.

One thing any artist, actor, writer, or creative person in general wants to achieve is to "melt" in the background, to blend with the work so seamlessly that the hand of the author isn't visible. Try aiming for that.

One approach you might want to try to achieve this is to never say "no," but to say instead "no, but." Describe their failure and then create a circumstance to make it worse. Reply to "Do I see any traps?" with "No, but because you didn't see them, you triggered them by accident. Make a Dexterity saving throw."

My personal favorite approach is to exploit the characters' motivations. Place them in a genuine dilemma. To accomplish one thing they want, they have to sacrifice another thing they love. This is...


Thanos sacrificing Gamora to gain the Soul Stone.



Ned Stark choosing to lie about the way Robert Baratheon died and break his code of honor to save his children from persecution.

Define the stakes. What do they have to lose? Do they care about what they have to lose? If the answer is yes, then you're doing good.

In conclusion...

Make sure that:

  1. You are all on the same page, that you all want to play the same game

  2. Your characters are properly motivated

  3. Your characters are properly grounded to the world

  4. Your challenges are innately interesting and engaging

At the core of this, make sure your players are buying your story. Sell the narrative effectively, and if you do that, your players will be engaged, even if they keep failing your challenges.


Make any outcome interesting

In my experience tabletop role play doesn't lend itself very well to a "Here is one problem you have to solve to continue" approach. While this works is many video-games, they are usually equipped with a quick-save and load option, a difficulty-setting, hints or online video-tutorials how to overcome a certain problem.

A usual group does not like getting nowhere or just running in circles. If the group spends 30minutes asking around and has no good ideas and doesn't roll very good you will have to improvise. Sure they failed on their primary task, but can you give them something else? A new lead to another problem? It could also be that a certain organisation heard of their asking around and sends someone to shut them up.

The importan part is player agency - the players have to feel their decisions and actions matter. Their actions should have consequences in the world, they should be feeling like they are moving something and changing something. The thing you should definitely avoid in most groups is an hour playtime after which the group is in the same spot as before.

In addition to this many groups also prefer some form of success over failure. If you have such a group, you should also strive to provide some form of small success with every failure. Failure not meaning an individual roll, but a bunch of tries to overcome an obstacle.


If trying to outsmart a bad person with a lot of influence in the town.

The group confronts him directly and tries to accuse him head-on of his wrong doing - they roll average. This of course fails and he smoothly talks his way out of everything and just laughs at them. He even boasts that they would not be the first "rat he drowned" this week for being an annoyance. And the group sees the major of the town uncomfortably waiting in the adjoining room, fiddling with some small package before he gets called into the room after they leave.

This would leave the group with two solid leads and feeling like the whole encounter was a success even though the direct approach was a failure.


Ask if they want to

The party didn't plan any grand schemes, any extraordinary strategies, no clever ideas on the spot, but rather tried very basic head first dialogue.

They probably can't, or do not want to play this way. You can't blame them for that. D&D 5e is a game about killing monsters and looting treasure*. It is not a game about diplomacy and intrigue, and it doesn't support that kind of cloak-and-dagger story well. No wonder your players prefer more straightforward ways first.

Ensure they have the required information

One of the purposes of game mechanics is giving the players information about what their characters are capable of. While playing D&D, we don't have much tools regarding diplomacy and intrigue, so DM's fiat often becomes the best option. This might be frustrating for players, especially early in the game. As a DM, you should give your players agency, that means players should have enough information to anticipate what consequences might be before making decisions.

You might need another session zero

Ask for feedback about the campaign as a whole. It might turn out that players expected (and still want) a different kind of game. Playing a game of intrigue might be interesting indeed, but so is playing a game of epic fantasy, might and magic.

You might also look for a different game system, with more robust mechanics for things like social interactions, intrigue and influence. DM's fiat is often the best option we have while playing D&D, which might be frustrating for players, especially early in the game.

*Don't get me wrong, I actually like 5th edition, it just doesn't really fit for cloak-and-dagger type of game

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    \$\begingroup\$ I agree that dnd 5e is different in respects to being more new player friendly, more hack n slash, and less available for cloak and dagger type of game, but I've talked to the party: one player enjoys more story / talking, one prefers more combat, so we've chosen a balance. I don't think them "not wanting to play this way" is the issue. I think they have enough information of their characters, but rather lack of knowing what possibilities they can do. As mentioned in the above answer, I think I need to give more clues / hints than I otherwise would. \$\endgroup\$
    – Ray C
    Commented Mar 26, 2020 at 15:57
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    \$\begingroup\$ Also as mentioned above, I did another quick session-0 to confirm or deny the above questions. They said it wasn't an issue of there being a diplomatic problem existing, or the fact that the problem was hard. Rather the lack of feeling of success after they tried a single solution in the session and it didn't pan out. \$\endgroup\$
    – Ray C
    Commented Mar 26, 2020 at 15:59

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