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I'm seeking some newbie GM advice. I'm an experienced rpg player, but am much less experienced as a GM

I was recently running an D&D 5e adventure, where the players would be investigating in a town that had some problems with trade caravans being attacked. They started at the local Sheriffs office who tipped them that a local relatively new thieving guild was active in the area. The thieving guild wasn't raiding the caravans, but I thought it might add a little plot twist to get the guild involved. My thought was to have the PCs eventually figure out that the guild wasn't behind the problem and would need to investigate the local country-side to discover the problem. I had a few encounters written out, but I wasn't fully sure how the PCs would reach their end goal of figuring out the source of the problem. I guess I thought that over-planning would be railroading and I wanted to give the players some freedom.

The players were often confused and unsure what to do. There wasn't quite the excitement I was hoping for. They were eventually invited to a parley with the thieves guild but were not sure what to do with the thieves, so eventually just attacked them. It was ok, but not spectacular.

What do you do when your players seem stuck?

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Players are often stuck because they simply don't know what they should do. Percival's message deals with player engagement very well, but I'd like to offer a slightly different take on this question.

If you can't figure out how the plot might be solved, players definitely won't

Players' ingenuity often amazes GMs, but you can't assume they will figure out the mystery for you. You have to leave them clues and hints pointing them in the right direction. This is especially true in non-railroading games. Think of it this way: if the story is about them tackling highwaymen but there are many paths they can take, you need a lot of signs and pointers to guide them to the destination.

For every mystery, establish three solutions, for every solution, three clues.

That is apart from what the players can invent themselves. There is an excellent article describing in detail why and how you should do it. In general, the players are often overwhelmed in your world - they are not Sherlock Holmes. You need to give them at least three ways to accomplish the narrative goal and for each of those ways, drop three hints that they can gather.

Be open to their own solutions

The players might decide to do something really innovative, like going to a clairvoyant hermit for advice or using bribery to have people rat the true criminals out. It should work and give them at least a clue if not be the solution outright. Unless, of course, it's completely inappropriate, in which case it should fail, but still give them a clue. Reward players' actions with clues, regardless whether they are right or wrong.

The clues have to be obvious

Fencepost to the head levels of obvious. It's not enough that they find a curious dagger, it has to be a dagger adorned with Thieves' Guild symbols, with Thieves' Guild telltale ornaments and screaming Thieves' Guild. Otherwise instead of a clue you present another mystery. You don't want a player saying "Oh, we have the dagger but what does it mean?"

No red herrings

It feels awful to pursue a goal and then discover you're at square one. The players could be hindered, but if you throw their theory out of the window it will be nonetheless frustrating. At least part of the theory should be relevant, so maybe the Guild is not the main criminal, but they helped them?

It all comes down to agency

Your players need to be able to take action. If they don't know what they should do, you need to give them more information. Introduce characters that will help them know how to deal with criminals, what are the success criteria. How about a guardsman who will tell the heroes "Well, the Thieves must know who did it, if they didn't do it themselves." Don't you think the players would act differently (and decisively) if they heard that? More on agency can be found here.

Solving your case

OK, so let's apply these to your adventure. Establishing the facts: The robberies have not been done by the Guild, but by the Cult of Shadow. Of course, you can insert any villain instead of the Cult.

To succeed, they need to find out that it was the Cult of Shadow.

Three solutions:

  1. Set a trap on the trade route or accompany a caravan.
  2. Investigate the robbed caravans, find out robbers are after holy symbols.
  3. Find the Cult's hideout full of stolen wares.

Now, the clues:

1a The Thieves Guild will happily set a trap if it takes the Sheriff's eyes off them.
1b The woods have a certain place where all robberies seem to happen.
1c The merchants are hiring mercenaries as protection for next caravans.

2a The local temple posted a reward for robbed holy symbol.
2b Thieves Guild claims the caravans robbed carried only worthless religious artifacts
2c The remains of a caravan show a left behind reliquary.

3a A priest complains about ghosts in the abandoned mine, where supposedly lights shine in the night.
3b One Thief is found dead, his blood tracks lead to the hideout.
3c The Sheriff says there are masked men witnessed in the hideout area, but doesn't think it's important at the moment.

With this amount of clues, it's unlikely they would get stuck.

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I think partly it may be down to how you're setting up the situation and incentivising the players. You haven't told us what the players are doing, their alignments or their aspirations, so if you could add that it would be helpful.

My assumption is that your players are all relatively good/neutral characters who are primarily playing DnD to have fun. They are playing archetypal heroes and want to feel powerful.

Give the players a reason to want to act

In every quest and every encounter, you need to ask yourself 'why would the players want to spend time and energy on this'. If the answer is not immediately obvious, then you're going to run into situations where the players just don't care enough to get invested. Is there a material reward in it for them? Does it get them something they want (not eventually, but at this moment in time)? Will it hurt their enemies?

Make sure the players know the possible outcomes

If they steal the Sceptre of Ultimate Power, what will it give them? Can they use it on themselves? Can they sell it? Will other people come after it? Will they need to hold on to it for months before it can be useful?

If the players are constantly blindsided by unforeseen consequences, they're going to be more leery in the future. This usually manifests itself as them players not getting too attached to anything because it can be taken away. This is a problem for you as a DM because if you make a quest, and the players aren't 100% sure of the possible outcomes, they'll usually default to 'do nothing, at least then it won't be our fault'. You want your players to trust you and trust your world, so that they know when they can take risks and what's at stake.

Dangle hooks with the right kind of bait

Is your group a collection of lawful good paladins? Then quests that promise them riches and access to vices probably won't be very effective. Are your PCs already rich? Then gold probably isn't a very good motivator (but a rare item probably is). Are your PCs mostly selfish or indifferent to suffering around them? Then you probably can't entice them into protecting a local orphanage for free.

As one of the comments above suggests, it looks like your players are more 'bored' than 'stuck'. It's not that they couldn't figure it out if their lives depended on it, it's more that they don't really seem to care one way or another. Given that, I have some questions you can ask yourself about your posted quest to try to determine where is issue is:

the players would be investigating in a town that had some problems with trade caravans being attacked

Why do the players care that caravans are being attacked? Other than the obvious 'because attacking caravans is wrong', what motivation do they have to find out who is attacking the caravans and how to stop them? Are the caravans carrying supplies to an ally of the player? Do the caravans contain important reagents for the creation of a wondrous magic item that the players are expecting to receive? Could the caravans be concealing a local politician who promises to help the players out if they can get him safely to his destination?

In a general DnD world, it's expected that caravans get attacked. Why would your players risk life and limb, in addition to the time and money required to pull off the defense?

They started at the local Sheriffs office who tipped them that a local relatively new thieving guild was active in the area. The thieving guild wasn't raiding the caravans, but I thought it might add a little plot twist to get the guild involved.

Why should the players go investigate a guild? Why is it important to do the sheriff's job for them? Other than caravans losing some materials, what is the big-picture problem that these thieves are posing?

This also calls into question the logistics of that the PCs can expect. In my mind, a thieves guild is likely to have dozens if not hundreds of members, so walking into their den is likely a bad idea. However, thieves are also generally great at stealth, so trying to sneak an entire party in is probably not going to work. Finally, thieves are usually expert liars, which is going to make any social encounter a real pain to pull off.

Also, having a PC lie to the party can work ('hey, the sheriff lied to us! Maybe he's in on it...'), but it can just as easily backfire ('Great, so we just wasted two sessions investigating a guild that was innocent because the one person we can talk to about this was wrong'). I've played in campaigns where we spent lots of time trying to solve a mystery, only to find out that the 'mystery' was just one person constantly lying to us about what was going on. The end result didn't make us feel cool or heroic, it just made us feel sort of dumb and that we'd wasted our time.

Is there any specific reason that the party would feel driven to solve this crime? What is the party going to learn from the thieve's guild?

My thought was to have the PCs eventually figure out that the guild wasn't behind the problem and would need to investigate the local country-side to discover the problem.

This doesn't sound like an amazing plot-twist revelation ("IT WAS THE BUTLER ALL ALONG!?"). It seems like an annoyance after they trusted the sheriff and spent time investigating. What is the purpose behind them being misled? What would make them think to investigate the countryside? Do they have access to any of the caravan drivers to get additional information about the plot, or would they just have to start wandering around and hoping they stumble into the correct answer? And again, why do they care about this particular caravan issue at all?

The players were often confused and unsure what to do.

Confused and unsure is the perfect time to drop a massive hint on them. They overhear a conversation between two bandit leaders about a third upstart that is poaching their business (and where the upstart is likely located). A wounded merchant stumbles into the party's camp and tells them they've just been waylaid and the bandits are running away right now. A distraught widow offers the party her life savings to avenge her husband who went looking for the real thieves at this specific location. One of the hardest things as a DM is to realize that what might be 100% clear to you is probably 100% opaque to the players. If they're confused, it means they need more clues.

They were eventually invited to a parley with the thieves guild but were not sure what to do with the thieves, so eventually just attacked them.

It sounds like you have some smart players! Who in their right mind would go to a parlay with a group of people who call themselves 'The Thieves Guild'? What would be the purpose of it, given that you can be 100% certain that you couldn't trust a word they said? Are your players the sort of people who would ally themselves with thieves? Would being a 'friend of The Thieves Guild' suit them well in this campaign, or would it lower their social status? Do your party members even need thief friends right now? Is anyone in your party particularly thieve-y?

I think if you look into answering these questions, you'll start to get an idea of why your PCs don't seem to care a whole lot about this.

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The solution I use is let the players do whatever they want, and then act like they did exactly what I expected them to do all along. This tends to work very well for me, mainly because my gaming group has an annoying tendency to to do the one thing I never imagined them thinking of doing.

In your case, it sounds like your players are unsure what to do, so try following these steps:

  1. Pick a player at random (usually the one who looks the most bored) and ask "What would your character do?" Try and get them to come up with an action - any action - based on their character's motivation. You can maybe help them along by providing environmental hints, e.g. "you've been standing there staring at the gates for a an hour now, and your feet are getting tired" or "you are feeling hungry after your long journey" -- that sort of thing. Just get the character to say they do anything. That action becomes your next plot point.

  2. Whatever they just did starts an event.

    e.g. They say: "I sit on a nearby bench".
    So you say: "The bench splits in half, revealing a mouth filled with jagged teeth. It is actually a mimic in disguise!"

    e.g. They say: "I go to the tavern".
    So you say: "You enter the tavern, and see a figure in a dark cloak shrouded in shadows, sitting alone. As you enter, he catches sight of you and leaps to his feet!"

    Then just weave it into your plot.

    • The shadowy figure turns out to be an adventurer from your past, here to help/kill you.
    • Or he's an assassin for the thieves, and he thinks you've blown his cover.
    • Or something like those examples. You had no idea the guy was even there until the crew enters the tavern. The action of them entering the tavern is when you invent him.
      • If they want to talk, he's an adventurer; if they immediately attack, he's an assassin.

The point is, you DON'T need to play out clues in advance - just let the adventurers do whatever they want, and then make what they just did into a clue. This way you guarantee that the players will never be wandering about unsure of what to do.

Responding to player actions and decisions makes the game a lot more fun and dynamic than if you are just sitting there, waiting for someone to randomly wander into your plot.

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The edit was intended to take a well thought out answer and give it some organization (as well as clean up some minor spelling and grammar bits). If this edit introduced errors or made a mistake in your intended meaning, please revert/re-edit. – KorvinStarmast Jan 5 at 15:34

I typically give them an ally, mentor, or sidekick who can make "suggestions" as to what they might try to do next, in case your clues are too obscure or the players are just not getting the hints.

But though I hate to say it, you should never have started the adventure when you yourself didn't know how they could get to the plot resolution. You should have not one but at least two or three ways for things to get from start to finish, and be ready for them to choose a fourth or fifth option you never thought of. It helps to have a range of NPCs that can "shepherd" the plot without railroading things. A criminal informant, a crazy prophet, a talkative bartender or farmer, or others can drop info to the pcs as needed.

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