Been watching Critical Role for the past few months. Wanted to get into D&D, so a couple weeks ago I started a session with my brother and sister. And I got to be the DM, SO...

I don't really have any of the books to use as a reference, just the basic rules. So I've started crafting a setting using old maps and drawings I made as a teenager. And boy is this kinda difficult. I'm starting the party in the red skull city on this map. Ignore the part in the description about country names, I'm not using those.

Currently the party consists of a gnome barbarian (my bro), a tiefling rouge (my sis), and an NPC cleric (they didn't have a healer otherwise).

In short: I've started a necromancer plot in a city that has strictly banned it. Meanwhile, the party is finding every possible avenue to avoid planned content and/or (nearly) get themselves killed.

In long:

 So... my next session is "after summer break", whatever that means. Any help and/or advice you experienced folk could give me and/or point me to would be greatly appreciated.

Now on to the main attraction, what I like to call: How to Herd Your Cats!

First rule of herding cats: you can't.

Second rule of herding cats: when you think you've succeeded, look at rule number 1.

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Ok, that said, you're dealing with the same troubles every newer DM starts with. How do we keep the plan intact after the players are introduced? The answer is: all roads lead to Rome. You're running a simple adventure, as opposed to an open world where anything is possible, so you have to confine the players to the adventure. Yup...I hear the choo choo, and I don't care!

Take your sister's actions for example, she ran off into the woods for no apparent reason...well surprise there's a site that indicates some nefarious necromantic acts took place. She could easily be caught by the town's guards and accused of dark magic.

Your brother visits the mayor, the meeting goes poorly, the mayor's brother, sister, barber, approaches later to give the information the mayor was supposed to. Then the town's guard finds the brother and brings him in, because he was seen travelling with the rogue who's accused of dark arts.

Bingo! You've stuffed the plot down their throat, it feels somewhat organic since their actions caused things to happen, and you can keep guiding them in the right directions.

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That's the approach I've had to take with my kids (9 and 10 yrs old) as they just want to run around and be silly. It's heavy handed, but sometimes necessary, and not wrong. You're there to adjudicate their actions, and push the story along. If your players are going to make poor choices they have to live with them, but you can also use those poor choices to push the story along as well. They fight something they shouldn't...they don't die, but they do find themselves in a situation that gives them more of the story and a new skill to try to lean about D&D.

I hate the phrase "fail forward", but in some cases using a failure as a teaching mechanic can be rewarding to the players.

DMThac0 pretty much sums it up. 

I would try another session and go with the tips you got (shove them on to the next step, no matter what they do - you might be surprised how fun it can be for all). 

Also, since they asked you for background and details, why not provide it? Since it’s your siblings, chose what you know they will think is fun or cool. The bond, flaw and ideal is a good start. Keep it simple. Inspiring one liners. 

Furthermore, start session two with leveling up and finish the session (however it ends, as long as they are alive) with “you gain another level, but we sort it all out next time”.

Consider also just having a chat later on about what is fun and less so. Try to find what you all can agree is entertaining and do more of that. You as a DM should enjoy it, and so should they. In the end, if none or few are having fun, finding other players might be the answer. 

My sister wandering into the woods was both our faults really. She told me she was wandering around town, so I just rolled a d4 to see how long (in hours) it took for her character to notice his surroundings, got a 4 and figured that was probably outside the city. Probably the wrong way to handle that.

I do have some ideas on how to maybe bring them back in, but ultimately I have to react to them. They are both avidly roleplaying as chaotic dispite both of their characters having above average intelligence.

I think, even if they veer too far off this plot, I can still have it continue in the background and get back to it later when it snowballs?

EDIT: Posted from a phone, so didn't see Eggnot's post. Sorry Eggnot!

My brother has certainly mentioned more about his character than our sister, so I can definitely begin to mold a backstory for him. My sister's is a bit more nebulous since she gave him amnesia. Been toying with that one a bit, not sure on what exactly her PC's actually haunted by, but I think we'll cross that bridge eventually- assuming she doesn't get her character killed.

Next session I'll definitely get them to level two at the very least. Maybe even grant them enough partial exp from semi-successful conversations to get there at the start? They were awkward, but did manage to forward some information to certain npcs (that realistically would've gotten that information anyway).

The thing about stumbling and fail forward (which I find a great concept in some cases) is that they don’t really miss the plot. 

Lost in the woods? Stumble on a hideout. 

Fall down the wall? Land right next to a cultist attacking a would be victim. 

Randomly attack someone? He drops a letter intended for plotters against the city. 

Whatever they do, have some reason for adding stuff regarding the plot. Not always, but often. If nothing else, they end up bumbling heroes that get rewarded richly for random acts that everyone else think intentional. 

A final note: don’t despair. Most role players in my experience (me included) starts off without really a clue and just do weird stuff. Some change, some just have fun with it. Nobody, I would say, starts out Crit Role. Aim for it by all means but accept it might be a long road. 😊

There's something to be said for that approach, I like it, but it has to be used sparingly, otherwise the players will feel shafted even if it is because of their actions (or inactions).

Now, on the other hand, you can use their chaotic natures to teach them that just because they can doesn't mean they should.

I had my son's character get called in by the mayor of a city so I could impart on him the plot hook. He wandered off in that direction without saying a word to the rest of the party. His sister's character kept doing what she was, which was wandering around town gawking at this strange place. My son's character made it to the mayor's house, was let in, and promptly sat down and took a nap in the waiting room. I had the mayor walk in, and get angry saying "If you can't show enough respect to stay awake for a meeting with the mayor...you can just leave. Good bye!" While that was happening, my daughter decided that her character was going to stand in the middle of a gnomish city, during morning rush hour and yell "Stampede!". I asked her why, she responded with "It looks like that to me". I promptly had the city go into a panic, the town guards arrested her for being a public disturbance. 

They, my kids, got mad because they got in trouble for "being their characters". To which I explained that just because you can, doesn't mean you should. Just like in real life, there are consequences to your actions. 

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Another time I used a simple example to teach my players, at this time my 2 kids, fiancee and friend, a moral lesson. They camped out for the night, the person on watch, one of the kids, heard a large creature moving through the forest near by. He woke one of the party members, leaving the other 2 asleep and went to investigate. The two found a griffon near the camp on the edge of a river. One of them ran back to camp to wake the others and bring them to the location. As the group got to the location it was just in time to watch as one of the kids said they were going to attack the beast. After a rousing bit of combat, although a bit difficult, they emerged victorious. The next morning they woke to the forlorn cries of 3 griffons, one adult and two babies circling above.

Well, I do have a full month and a half to plan this out. I can at the very least flesh out a few of the shops and npcs they'll encounter around the city (assuming they end up back in the city). As well as some of the surrounding wilderness.

Maybe next time my sis wanders around, instead of rolling to see how long they're walking, I just roll to see which direction she wanders and adapt to that?

Maybe while I'm fleshing out the friendly npcs I can cut down on the number of elves I seem to generate. The archers at the gate, the poor-house manager, at least one shop keep, as well as the guards at the mayor's estate... Actually thinking about it, that's just the ones the players interacted with, that's not the amorphous blob that is regular foot traffic.

At this point I'm more theorizing for the next session. So how's this for ideas:

• The party is camping in the woods currently (between sessions), not far from the city. The gnome barbarian had a partially successful, if awkward as heck, conversation with the Mayor and his Spymaster. I could, in theory, have a messenger or message waiting for them at their camp when they wake up (If I recall correctly, they left the cleric NPC PC to have first watch, and might not be taking any other watches.). The idea being that the spymaster sends them into town to either a suspicious location, or-
• Just realized I'm having to play cat and mouse between a very intelligent wizard (necromancer is an npc pc with 20 INT) and the local spymaster (minotaur wizard stats TBD). The spymaster having the advantage of an information network, and the wizard having some pretty advanced control and stealth spells, as well as the Teleportation Circle. I rolled her up to Level 9, so just high enough to have that. It's possible I'll just try and focus on having the players aid with information gathering, since only one of them casts magic, and that's the cleric npc. I should probably roll up a few locations where she could be hiding, since the city is on alert for her. Although she does have the spells and skill necessary to hide in plain sight...
• I'm just now realizing I'm too focused on the necromancer plot. It's a fun, if large and frustrating puzzle for me, but... I don't know, I guess I'll see what happens in August. (maybe it'd help if I rolled the stats for the spymaster as well?)

I think you're trying too hard. 

What information did the barbarian learn? Give it to them.

Why do you need to know what back and forth is going on between the Spymaster and the Necromancer? The players don't see it, so why work so hard on it?

Is the necromancers spell list important to the Players? if not, don't worry about it until the fight.

Is the Teleportation Circle important to the players/plot? If so, how?

The fact the necromancer can move about freely and has multiple hideouts, is that important, if so how?

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Work on what is front facing at this moment, and what you want your players to learn. Figure out how fast you want them to get information, and pace your sessions to it. Figure out what your players still need to learn, and integrate it into the session. Figure out what game mechanics and structure need to be understood, and integrate it into the session. You only have to work on what's important for the next session, bullet point important events, and let your players tell you how you're going to connect the dots for them.

Good point. I do have a tendency to hyper-focus on one thing for a while. And just dwell on it.

Necromancer's probably gonna lie low for a bit while the city's on a higher alert. The teleportation sigil was a clue that got found and used already. Just a permanent sigil outside the city's southern gate. It's no longer relevant. I already have the stats for when/if the party ever encounters her.

While the players were kinda helpful, they've been obnoxious, so... maybe I should just keep a list of grievances they've committed? I'll do that in a .txt probably. Probably also make the guards more likely to straight up arrest them for disorderly conduct.

As for what they're doing next, um...? I dunno, I've got over a month to plan the next session.

There, that sounds like the perfect place to be as a DM.

You have the important parts in place, you have a couple loose ideas on what you can throw at your players, and you have a way to turn their actions into something that is part of the world. 

I like the idea of them being called out on their "grievances", something to make them realize that they're not immune to consequence. 

I'll toss this idea at you:

Maybe the necromancer has her own spy network...the spy master stumbled across an informant...the players are tasked with helping with that endeavor. Though rather than getting compensated like good little adventurers...this is community service for being a public nuisance.

I like that plan, here's what's been playing in my mind over the last little bit as well:

In the meantime, coming up with more wilderness encounters in case they wander around the woods instead of going back to town.

That's a fun idea, it really makes the world pop when you can tie in things like that.

Apparently my sister's not going to leave for dad's house as early as I thought, and will only be gone during the one week I have to work 6 days in a row. So I don't have nearly as much time to prep the main starting area as I thought, since my next weekend has a day or two where I might be able to squeeze in another game, dependent on the rest of the family's schedule. That's okay I think, since I've some ideas that'll burn a hole in my brain if I don't use them soon.

Since I realized that my players can probably see this thread, vague "Pretty Darn Specific Because I Want To Know If It's A Good Idea" spoilers below.

I hope it's not too much trouble if I just reuse the same thread instead of making a new one every time. Especially if it pertains to pretty much the same thing.

 As for the spoilers. If I find out any of my players have discovered this thread and plan to metagame. I am prepared to change the story by quite a bit. Perhaps that ghost-ship on the map is real after all... (That, or the giant Blooper.)

Edit: Maybe I should wait to resume the necromancer plot until the players are tough enough to not almost get themselves killed at every opportunity.

Edit the Second: We had a talk, and we're probably gonna end up scrapping this campaign. We kinda jumped the gun with this. That first session, I was excited and just wanted to try out the combat. I was then asked by the other two yayhoos to turn it into a full campaign. I wasn't prepared for that. If we do scrap it, we'll do the session 0 like we should've done. That will give me time to properly flesh out this kind of plot in the background, and give them something they can actually handle.