Wisdom of the Masters: Winging It

Wisdom of the Masters: Winging It

This article was first broadcast in Episode One Hundred Thirteen on 1st April 2020.

Ostron: I thought you said this wasn’t ever going to happen? 
Ryu: Yeah, I did, but then he taught me some stuff about Thieves’ Cant and here we are.
Ostron: I thought you already knew Thieves’ Cant?
Ryu: Hmm? Oh, uh, yeah. I meant I taught him. He definitely didn’t teach me. Nope. I mean, can you imagine it? Me, a rogue, who doesn’t know Thieves’ Cant?
Ostron: Yeah, that’s highly unlikely, statistically speaking
Ryu: Anyway, stuff and things, here we are. No! Peaches, stay. 
(grumbling sound)
Ryu: Yes, you can play with KayDee’s nightmare after, I just need you to stay. 
Lennon: Okay! Bike is all set, helmet’s on, let’s do this. 
Ryu: Um, Lennon? You have to start up at Peaches’ head. 
Lennon: Right. Ladder? 
Ryu: With a bicycle?
Ostron: Did you plan this out at all beyond “Use Peaches as a bike ramp?” 
Lennon: What for? I mean, that’s about as much planning as I do for D&D on any given day. 
Ostron: What? How?
Lennon: It’s really not that hard. m

A lot of people who see live play shows like Critical Role or Relics and Rarities or other high production value shows assume that DMing a D&D game requires multiple hours of preparation each time to account for plot hooks, NPCs, settings, encounters and everything else.

Now in the interests of full disclosure we should say that in the case of something like Critical Role, you’re 100% right. Matt Mercer has said he does about 3 hours of prep per session, but something to keep in mind is they’re doing a show for the purposes of entertaining the masses. They can’t really afford to go in without preparation because they aren’t just doing the game for themselves; they’ve got an audience of several million people expecting to derive some level of enjoyment from what they’re doing.

However, unless you’re also producing a live play video or podcast show, 3 hours of preparation per session is probably overkill. Resources like Sly Flourishes’ Lazy Dungeon Master books go over in detail how to cut your prep time down to a reasonable amount of time by focusing on general concepts and boiling down what the game sessions will definitely need, rather than trying to fit in everything you want or trying to account for every contingency.

We won’t rehash all of his strategies here, but we will say he doesn’t advocate doing no preparation at all. Some people will say the best games they’ve ever played were the result of having no plan going in and while that may be true for an isolated session, establishing it as a pattern for DMing is risky and relies a lot on having a good understanding of D&D rules, a gift at improvisation, and a tolerant and accommodating group of players. It’s better to have some notes, encounter ideas, monster stat blocks, and some NPC profiles ready to go, even if you don’t have all of the story beats outlined before you start.

But let’s talk about that isolated session. You’re supposed to DM a game that night, but you never got your breaks at work to finalize your notes, a meeting ran late, your commute home was delayed by a wandering herd of turkeys, and this is the one week every player decides they’re actually going to show up early for the session. So you stumble in the door and see a bunch of Role Playing enthusiasts sitting at the table, character sheet in front of them, pizza in one hand, d20 in the other, and expectant smiles on their faces.

Now, collapsing to the floor in a heap of tears and having a nervous breakdown is an option here that will get you off the hook, but it may not solve the problem; there are a bunch of people who want to play D&D, so now one of the players may suddenly find themselves in the role of DM, with just as much prep as the gibbering mess in the other room had.

Point is, assuming the group doesn’t decide to just cancel the session, someone is going to have to DM cold, with barely any notes. It is very possible to still have a good session in this scenario, but a certain amount of crisis management has to occur, and some of it is universal.

First of all, we’re going to turn the normal advice on its head. Talk to your players. Reasonable people, even those who haven’t DMed, should be able to recognize there are unusual circumstances and some extra allowances may need to be made; you are a real person who does something other than D&D, life happens. That said, it’s not like you can expect them to wait for an hour and a half while you write or re-write all your notes, look up monsters, etc. You have to meet them halfway.

Unfortunately if you are not a real person or you do nothing but prepare and play D&D every waking hour of the day, you have no excuse and your players are within their rights to shame you.

Next order of business, what was supposed to be happening that evening? Because the answer to that question dictates your next steps. Boiled down simply, you have three options: try to do what you were going to do anyway, possibly with stripped down or modified circumstances, take the Monty Python approach and do something completely different, or work out some sort of a hybrid.

Picking up what you were going to do anyway is usually done when the group is in the middle of a long-running campaign, and within that campaign they were in the middle of a quest. A lot of DMs will end things on cliffhangers or on big reveals to ramp up player engagement, and players will be expecting some sort of payoff. If it was right before a battle that may be the easiest; even if you can’t remember exactly what enemies you chose before, you can simply and quickly build another encounter of appropriate level using something like D&D Beyond or Kobold Fight club. The setting should be something in collective memory but we’ll also take this opportunity to reinforce the wisdom of having someone other than the DM taking notes during session. If someone wrote down “we were in a junction in the sewers under Waterdeep,” that’s enough for the DM to set the scene.

Similarly, if the characters were wandering around in a dungeon and you don’t have your map handy, find another map online that has geomorphs that make sense for the rest of the dungeon and quickly generate a few encounters.

If it was more of a social situation and you don’t have your notes but you remember the overall path of the campaign, you can try to improvise it. A lot of social encounters are fluid anyway, so all you need to do is come up with key NPCs that are around and what their motivations and goals are. You may not even need stat blocks for them; just have numbers for their persuasion, insight, and deception skills, and values for their wisdom, intelligence, and charisma saves, and you should be able to account for most rolls you’ll need to do, assuming combat doesn’t break out.

In both of those scenarios you may need to retroactively edit your campaign notes, and some NPCs names may need to change but, again, if your players are aware you’re winging it, they’re less likely to be shocked.

Side note; if you’re running an official adventure like Tomb of Annihilation or Waterdeep Dragon heist, this scenario is a good argument for having a spare physical copy of the adventure within the group. That way if the DM misplaces their copy or D&D Beyond is unavailable for whatever reason, you still have access to the module and most of your preparation problems are solved.

Now if you were in the middle of a campaign but not in the middle of a quest, this is a good opportunity for the hybrid approach. The players can use their characters and even the same setting, but instead of whatever was planned, they get involved in whatever one-shot or short adventure you managed to look or make up in the 15 minutes you bought yourself by explaining you need some extra prep time. You will probably need to re-skin a few things like the location, names, or maybe some of the monsters, but then again if you’re running a campaign in the Forgotten Realms you might even be able to skip that part.

This is probably the easiest option where you’re still playing because there’s barely any prep needed on either side of the screen; all the players are still using the characters they’re used to, and the DM has a pre-made adventure they only need to skim over. It is better to fully read adventures before running them for your party but, again, this is why you talk to the players and explain that this session is something exciting and different, and part of the excitement is the players giving you a few minutes to read up here and there when they are invariably presented with options A, B, and C and decide on option Q.

It should be noted that if you are comfortable enough with the system and/or if you’re planning an adventure where character and NPC stats are less critical, it may be possible to make up an adventure in the campaign universe instead of reskinning a released one. However, again, that should realistically only be attempted if you think you can pull something convincing together in 15 minutes or so.

Option number 3 is similar to the previous option in that the DM is probably either finding or very quickly building an adventure for the characters to run, and it’s probably a one shot, but they’re making no attempt to link it to the existing campaign world. This is probably the route many groups will have to go if they’re running certain published adventures and don’t have access to the sourcebook, for example if the characters are deep in Avernus or in the middle of Ascerak’s tomb.

The big thing with this approach is that the players will need to use different characters. That can be quite a time sink itself, particularly if players are not familiar with or not invested in making characters. Most groups have at least one or two players that put together an absolute menagerie of characters just for the exercise, but there are others who agonize over putting a character together and breathe a sigh of relief once the campaign starts and they don’t have to worry about it anymore.

An easy solution to that is to either find a premade adventure that includes pre-made characters, such as the Rolled and Told resource, or find a web site such as fastcharacter.com that can generate fully formed characters with minimal input. As long as the player isn’t picky about specifics, you can very quickly generate a character for any player and get people ready to play without all the time and energy that a normal session 0 involves. Some coaching may be necessary if players get caught up on crafting a complex build or insist on overemphasizing character backstories. Remind them that this is a one-shot, so chances of these characters developing a story arc or even needing to be alive after the adventure finishes isn’t something they need to worry about; playing a D&D game in the remaining time is.

In several scenarios here we mentioned grabbing pre-made adventures. If you don’t have a library of them already, the DMs Guild is a decent place to start, but other resources such as Kobold Press or the One Page Dungeon publication can provide you with a wide variety of quick and easy adventures to grab if you’re stuck in the panic situation we mentioned. The DMs Guild in particular even has categories where authors can link their adventures to existing resources, so if you are in the middle of a campaign, you can specifically search for adventures related to whatever you’re currently playing. Just make sure to pay attention to the target levels for the adventures; you don’t want to suddenly have the characters facing an adventure meant for characters twice their level.


Ryu: Unless your solution to not prepping is to call KayDee in to substitute.
Ostron: That sounds suspiciously like the voice of experience.
Ryu: I don’t know what you’re talking about. Can you just levitate him up there so we can get this over with?
Ostron: Fine. Mount up.
Lennon: Set
Ostron: Aaaaand up to the head and oh boy.
Ryu: No! Peaches, tail up! up!
Ostron: She flattened it.
Lennon: (deleted)!
(sounds of expected humor and pain)
Ostron: Well at least he ended up in the right place.
Ryu: I didn’t even think it was possible to go straight from the back door into the scrying pool room. 
Ostron: I don’t think straight lines came into it. Come on, we should go join him.