When I was new to running D&D games I was often frustrated because I couldn’t get to key moments in the session, the players never did what I wanted, and I often over-prepared material that never saw the light of day unless I forced it on them Clockwork Orange style.
Now that I’m more experienced, those things still happen, except I don’t waste (as much) time preparing stuff that doesn’t get used. I estimate my encounters much like I estimate software, and because I do this I am able to make my sessions very rich and flexible at the same time. Here’s how:
1. Make a list of potential scenes or encounters that could come up in the session
This step is similar to writing stories. We don’t need to get very detailed about it though. At this point keep it high level. Here’s an example using a session where I’m planning for a dragon to attack the city where the players are located. Its their 2nd day there, so I expect them to want to do some town business as well.
Examples:
- Waking at the Inn
- Shopping in the marketplace
- Visiting the potion shop
- Visiting the mayor’s
- Altercation with guards
- Players get arrested
- Encounter with a pickpocket
- Dragon attacks the city
- Players fight the dragon
- Players run from the dragon
2. Estimate encounter size using story points (fibonacci scale)
The number of points I will give each potential scene is based on the fibonacci scale (1,2,3,5,8,13, …). These number are used in estimating work in software development, because the work is often unpredictable. So we measure them in numbers that are relative to other stories, rather than by absolute values, like number of minutes.
This applies well to scenes in D&D because they are equally unpredictable. The “this should be quick” statement is just as wrong whenever its said while prepping a session.
I don’t want to go too deep into story pointing, so I’ll just give you my scale for reference. Keep in mind that I estimate about 12 points per session:
| points | description |
| 1 | Quick exchange with an NPC. A combat encounter that lasts less than one round. A simple trap or obstacle. |
| 2 | An exchange that will probably have some back-and-forth. A combat encounter that lasts 1-2 rounds. A trap or obstacle that will require some interaction to pass. |
| 3 | A lengthy exchange with an NPC or lore drop. A combat encounter that will last a few rounds. |
| 5 | A long series of social encounters that takes up almost half the session. Like a large party or dinner. A long combat encounter that takes up about half of the session. |
| 8 | A combat encounter that takes up most of the session. You might have time for 1 or 2 other quick scenes. |
| 13 | A massive combat encounter that spans multiple sessions. |
Remember, these numbers are totally made up, they’re completely relative to me and my game. Your idea of what makes a 1 or 3 might be different and your budget may be totally different. You also have to consider party size and how long your players take on their turns.
Given this scale, I’ll assign points to each scene I previously brainstormed:
- Waking at the inn – 3 points
For whatever reason the players are always prone to ordering food, chatting with the staff, tipping insanely high amounts of money, and getting distracted at the inn. - Shopping in the marketplace – 3 points
The players already sent me their shopping lists. But I know if they go here they will gab it up with every shopkeeper and haggle on every purchase. - Visiting the potion shop – 2 points
One player has to follow up about a special potion, so I know they will chat a bit here. - Visiting the mayor’s – 5 points
There are so many people to talk to here it will probably eat up half the session. - Altercation with guards – 3 points
The guards here are really strong compared to the players, so I don’t think this encounter will drag out. Either the players will run or they’ll get shut down and arrested pretty quickly. But you know, never underestimate the players, I guess. They could definitely find a way to drag this out. - Players get arrested – 3 points
Them getting arrested could definitely derail things, but with the dragon coming to attack the city, a chance for escape will be easy to present. - Encounter with a pickpocket – 3 points
The pickpocket is not very tough so the players should stop them pretty easily, or they might succeed on escaping the players. - Dragon attacks the city – 1 point
The description of the dragon appearing and attacking the city does not need to draw out. I might present them with a couple of skill checks here. - Players fight the dragon – 8 points
This dragon is a very important NPC that the players have history with. This should be a meaningful battle that the players remember. - Players run from the dragon – 3 points
As much as I hope they don’t run, you never know. But this could be a fun and interesting set of challenges itself. But unless they fail to escape the dragon this should be easier than fighting it.
3. Prioritize Scenes
“Art is the elimination of the unnecessary.”
– Pablo Picasso
Just like stories on our Jira or Trello board, we should consider which stories are at the top of the stack. We’ll judge them by how likely they are to happen and how important they are to the story.
(For this next step, I don’t really write stuff this on paper and do all this math. I just do a a quick mental calculation to help prioritize what to prepare the most and this is what that process looks like broken down)
Here are the encounters listed by the two dimensions.
| In order of priority | In order of likelihood |
| 1. Dragon attacks the city 2. Players fight the dragon 3. Players run from the dragon 4. Shopping in the marketplace 5. Visiting the potion shop 6. Altercation with guards 7. Players get arrested 8. Visiting the mayor’s 9. Encounter with a pickpocket 10. Waking at the Inn | 1. Waking at the Inn 2. Dragon attacks the city 3. Players fight the dragon 4. Shopping in the marketplace 5. Visiting the potion shop 6. Encounter with a pickpocket 7. Altercation with guards 8. Players get arrested 9. Visiting the mayor’s 10. Players run from the dragon |
I can now use a simple formula to order the priority of scenes for preparation: (10 - (order of priority)) + (10 - (order of likelihood)) = score , which when applied to above gives us a new list, ordered by highest score first:
Dragon attacks the city (17) – this is the most important thing to plan. Its going to lead to pivotal changes in the campaign and I know its going to happen as long as the players don’t leave the city. The dragon arriving is just a one point story and should happen even if the players will end up fighting it next session.
Players fight the dragon (15) – I expect the players will take on the dragon and defend the city, so I want to prepare a really cool encounter. This is going to be a well-thought out encounter with maps and environmental hazards.
Shopping in the marketplace (12) – I know this is going to happen because the players are very eager to spend some gold, so I may as well make this as interesting and fun as possible.
Visiting the potion shop (10) – One player let me know he’ll do this. It doesn’t need to be a very memorable scene but I should be prepared for it.
Waking at the Inn (9) – I will try to skip this but will prepare NPC names just in case. Everything else will be improvised.
Players run from the dragon (7) – I don’t think this will happen but I should be prepared with some ideas for an interesting encounter if it does happen.
Altercation with guards (7) – going to have some guard stat blocks prepared, but nothing more than that.
Players get arrested (5) – if this really happens I’m just going to improvise. Jail happens, then a wall crumbles when the dragon attacks and they can walk out.
Encounter with pickpocket (5) – I will prepare a name for the NPC and a few details and will improvise the rest. If there is more to do with underground connections I may set this up to be a hook for other things.
Visiting the mayor’s (3) – At this point I really hope the players don’t go here. Its the last thing I want to prepare. They did mention wanting to meet him but I think if I don’t bring it up it won’t happen. I’ll have a list of NPC names prepared and if they come here I will improvise. If I feel like I’m struggling to improv I’ll drop the dragon attack. I really don’t want to waste time prepping this.
4. Break Scenes Down into Smaller Scenes
Just like with user stories in software development, we want to have smaller stories. So at this point I will consider if anything that is 5 points or higher can be broken down into smaller scenes.
The only scene I have that is 5 points or more is the dragon fight, but I do think I can break that down into multiple scenes that could take place across the course of this fight.
Something like
1. Dragon starts sweeping attack of the city – description of the dragons approach and initial attacks
2. Innocent bystander about to be crushed – as the buildings are coming down a player notices a pile of rubble about to fall on a civilian
3. Soldiers huddling in fear – as the players move through the city they discover a company of soldiers hiding in fear
4. Meet the City Mage – If the players end up unsure what to do they encounter one of the mages who points where the guard is forming at attack on the dragon.
5. Dragon fights the players from the air – the players join the guards in their ranged attacks on the dragon
6. The Dragon speaks – once the players hurt the dragon enough to capture its attention, it will parlay for a moment
7. The Final Confrontation – Once the players have the Dragon’s attention, it focuses on them in a final confrontation.
8. The Dragon Flees – Once the dragon is below half its HP it will attempt to escape
Breaking down big encounters into smaller scenes makes them more interesting and helps keep the players attention. Conversely, huge scenes that take up the whole session without changing the beat are what get players looking at their phones while they wait for their turn to come back around. Another way I could break this up is to have the Dragon move across the city, destroying or looking for something in particular, and the players have to move across town to catch up and fight it. That would break up the scenes in a similar way with less planning. But since this is my #1 focus I will take the time to prepare interesting little challenges throughout the battle.
5. Prepare Each Scene
Now that I have prioritized the scenes and broken them down into smaller scenes, I can prepare each scene in the order of highest to lowest priority. I’ll plan rich details and robust maps for the most important scenes, and may just improvise the scenes with lowest priority.
6. Run the Session and Adjust as you Go
Because we are agile we will reassess and readjust as we go. So imagine the tavern encounter does blow up and takes up half the session. I would consider dropping the dragon scene into the middle of what they’re doing. Since I’ve estimated my prepared encounters, I know which I can bring in for the remainder of the session.
For example, it’s possible the marketplace encounter ends up taking half the session and everyone ends up having such a great time that I no longer have room for an 8 point dragon encounter. That’d take too long. So with about 1/3 of the session left I can pull in the pickpocket encounter and the guard encounter, leaving the 1 point dragon appearance as the final scene, and we end on a cliffhanger. That sounds awesome too.
Either way, by preparing the session in this way I feel ready for the players to turn the session any way they want while making the content detailed and well thought-out. I avoided a lot of wasted time by not over-prepping the tavern, pickpocket, or guard scenes.