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HELP! I'm a new DM

Some great advice here. I'll drop in again with some more advice regarding improvising.

Don't write the outcome, think up character motivations

When I write an adventure, I don't write the outcome. But I do try to think about, is what the various outcomes could be. See, if I understand the motivation of all the people involved, then it is pretty logical to come up an outcome based on what the players do. So understand the characters that you write, and then their reaction seems simple. If an adventure does not turn out how you thought it would, embrace it. Just run with it. So the players decide that they don't want to help the village besieged by orcs, great! So what would be the logical outcome of that? Most likely the orcs take over the village, killing everyone... perhaps they even establish a base of operations there, because there's an orc chieftain who wants control of the region for his evil master! Ah, but who is this evil master? Now we're getting somewhere. Once you start thinking about these questions, the story writes itself.

Always escalate the situation

My personal rule is that things never go as planned. When the players go on a quest, they always have incomplete information. Things never turns out the way they seemed at first. There are always twists and unexpected turns of events. This is how you keep your adventure lively and exciting! Good guys turn out to be villains, villains turn out to be good guys, and even the most well laid plans never go according to plan.

Why is the dragon attacking a local town? Maybe he has a really good reason? Maybe the king who hired the adventurers to slay the beast, is really a complete bastard, and the dragon asks the players to aid him in his fight against the king instead? Always keep your players guessing!

Don't just tell them what happens, but offer them opportunities to react

The key to any good D&D campaign is not just in a good story, but in the players to be a part OF that story. So don't just spoon feed them pre written cut scenes. But give them things to respond to. You want to involve them in what is going on.

"While player 1 is playing a game of cards, player 2 can see one of the npc's cheating, but she is kind of hot! What do you do?"

"You suspect that the baron may not be giving you all the relevant information, but it would be very rude to demand him to reveal his secrets. What do you do?"

"While player 1 strikes a deal with the innkeeper to return his stolen horses, player 2 notices that a mysterious stranger seems to be listening in on the conversation."

I like giving my players extra things to react to. While one thing is happening, another player will notice something that adds extra complexity to the situation. This is not all that difficult to improvise. Because most likely you were already planning to introduce a new character for this "horse-fetching-quest" anyway, and this is simply a more interesting way to introduce him.

Even unfinished quests can continue to affect the story

Sometimes the players may choose to ignore an obvious dungeon, or ignore a specific quest. Don't feel bad! I know you were looking forward to serving them a delicious monster and trap-filled maze with an epic boss at the end. But players can decide for themselves if their characters would take that bait. Instead, try to think what the likely outcome could be of ignoring said dungeon or quest. If the merchant can't convince the players to help him get back his stolen painting, then maybe he'll hire some bad guys to do it for him. Maybe the city guards trace the crime back to him, and he ends up in jail! Maybe that ignored dungeon slowly becomes a much bigger problem for the nearby town, and it escalates the situation, leading to far more interesting turns of events? Maybe the zombies of the nearby catacombs drive all the people out of town, and leave it to the undead, thanks to the lack of interest of the players? And maybe a quest to rid the town of undead is far more exciting to them then wandering into an underground undead infested maze?
 

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Try to wrap your head around all the different kinds of ways to structure and design adventures, finding the one that fits you and your groups style the best. I agree with the poster who suggested considering situations rather than stories. Given that your group seems to be a bit prone to going off track, you might also look into sandbox adventures (those can be heavier on the prep end though).

A lot of people will give you plenty of good advice on prepping adventures. But I am going to focus on something that has tripped me up every time when I don't pay attention to it (and therefore made prepping and running things on the fly harder): note taking and organization of materials.

One piece of advice that really helped me was to create a master Table of all NPCs, then update that table after every session. You will very quickly amass a large number of NPCs in your game (some important, some less important, but even the latter often come up again). Getting the details about them right are key. It is important to know where an NPC was first encountered, what that NPC did with the PCs, what its attitude towards the PCs is, whether the NPC is still alive (this actually gets hard to remember once your NPC list is over thirty entries), where the NPC lives, what the NPC does, etc). This sounds like a lot of detail, but all my entries are a single paragraph (for more detailed stats and background information I have seperate sheets for important NPCs). This is a huge time saver both in game and during prep. If there is ever any question about someone the players bumped into back in the village who gave them that talisman, then you can look it up real quick.

Similarly don't forget to keep good records of places, especially settlements. I always make entries with maps for my settlements, that include details on the population, inns, shops, organizations, etc. A lot of this may come up on the fly in an adventure (whether you are inventing an inn or the city itself) but it is very important to get the name of that inn down as well as the name of the proprietor because if the PCs go back to the city and want to visit the inn in six months, you'll need to remember those details. You can also add in new details as time passes.

Most importantly, get a 3 ring binder, structure it according to your preparation and running style (this takes a bit of time to figure out). I have a tab for: CALENDAR, EVENTS, ADVENTURES, NPCS, PCS, SECTS, OBJECTS OF POWER, and this is followed by 8 Tabs for each of the Major regions in my campaign (essentially a LOCATIONS section). For my calendar, I have a literal months calendar with one sheet for each month in the campaign world. It includes information on the beliefs surrounding that month (since people get bonuses for certain things each moon phase) but I mainly use it for tracking time and helping figure out when things will happen (if the players send a messenger to a neighboring town asking for help, I can put a note on the day that help would arrive). Events are just a bullet point list of things likely to come up each session based on last session (i.e. Bone Breaker is really mad at the party and sends out parties of soldiers with dogs to track them down, The Qinwen Jade Palace Cult is trying to reach the Face of Vaagu before they do, etc). I don't typically prepare structured adventures, so my Adventures tab is rarely used (mainly my adventures are situational and sandboxy). But I do use it when things in the EVENTS folder are more robust and require a little more page space. So if there is an event that is likely to turn into a mystery or monster hunt, I'll write that out a bit longer and put it in the Adventures folder. However I try to keep my location material in the LOCATIONS section because it can be a huge pain if you have to sift through an adventure folder on the fly for a specific place on the map. So the ADVENTURE folder is more about developments, investigations, elaborate schemes by NPCs, etc. My NPCS folder has my NPC master table plus individual entries for each major NPC. This gets a lot of use during play. My Locations section has my encounter tables and entries for each place on the map, divided by region and each region is organized alphabetically. Once you get a system like this establish it really saves time before, during and after play.
 

Yeah actually, now that Bedrock mentioned it, two things that always helped the longer campaigns I ran were a clipboard list of all the NPCs the players met, and the gist of who and what they were, that I kept behind my screen, and a month by month calendar that we had taped up on the wall of the game room that we'd write on as a Cliff's Notes journal of what they were doing, and where they had been.
 

Yeah actually, now that Bedrock mentioned it, two things that always helped the longer campaigns I ran were a clipboard list of all the NPCs the players met, and the gist of who and what they were, that I kept behind my screen, and a month by month calendar that we had taped up on the wall of the game room that we'd write on as a Cliff's Notes journal of what they were doing, and where they had been.

A rolodex or just a tray with index cards is also a good way to manage NPCs and other setting details (I used to that in 90s). What I like about a rolodex system is it is very easy to find and grab details on the fly, then update the card right there before putting it back. So if you pull out the Old Oak Inn card, and the players smash a wall while they are there, you can note the wall damage.
 

Yeah, the only reason why I used clipboards was because I had a place to hang them along the edge of my old game table so that they weren't eating up table or shelf real estate. Once the NPC became noteworthy enough they'd graduate to a 4x11 character card that I'd hang over the edge of my DM screen, picture on one side, DM info on the back, those I'd keep in a little index card file on a shelf.
 

Yeah, the only reason why I used clipboards was because I had a place to hang them along the edge of my old game table so that they weren't eating up table or shelf real estate. Once the NPC became noteworthy enough they'd graduate to a 4x11 character card that I'd hang over the edge of my DM screen, picture on one side, DM info on the back, those I'd keep in a little index card file on a shelf.

I think the clip board is a great idea (really whatever method works best for you is the one to use). I am curious about the calendar. Mine has always been in my three ring binder, but I've never considered using a wall calendar that everyone can see. Do you find that helps your players get more invested in the passage of time?
 

One thing I found helpful is to draw up a sheet of all the monsters the players might encounter in a session in advance, and roll separate hit points for them to avoid just using the 'standard' HPs. The sheet includes AC, attacks (to hit and damage, multiattack etc), initiative and saving throw modifiers, XP value and for spellcasters I think about what spells they might use (if I were them) and note down number of slots and likely uses, e.g. L3 1 slots - shatter at L3. Of course that might change but it really helps keep things flowing if you don't have to stop and look stats up and read spell descriptions to choose what to cast, and you then also have a ready-written record to chalk hit point losses off on.

I tend to panic if I feel I am delaying things and less prepared than I should be. So doing that work in advance I enjoy the session much more, myself, and it flows without so many delays.
 
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Do you find that helps your players get more invested in the passage of time?

Definitely, more so than even the weekly player-journal emails that we did. Having something physically there to look at, and something that they could use to answer their own questions as to what had happened kept them far more grounded in what was going on.
 

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