How Much to Plan for One D&D Session

You and your companions get off the boat and onto the dock of New Tuyen. You look around letting the sights and sounds greet you. You walk towards the city and allow yourself to acclimate to this new city. 

You first notice all the green. The buildings and roads are all made with a green material. After talking to a local citizen, you learn that the material is actually a moss that is particularly dense and sturdy. You also take in the smells of local street vendors who season their meats with intoxicating spices. Your stomach rumbles and mouth salivates as you pass one particular stall. 

The thing that strikes you the most are the people. You’ve heard about genassi but you weren’t prepared for this. Every person you has the form and shape of humanoids but instead of skin you simply see and element. One man made of fire walks past you without burning you and immediately after a woman made of shifting sand walks by without leaving any sand behind. Each person wears clothing like normal and their bodies are shaped like yours, but they seem so foreign. Especially alien to you are the space genassi. Their bodies looks like fields of stars and hair look like nebula. You’ve never seen anything so beautiful yet strange. 

Welcome to New Tuyen.

What would you like to do?

Welcome back to the 33rd episode of How to Be a Better DM. I’m your host, Justin Lewis. Together, you and I will explore how to tell better stories for yourself and your players as you DM sessions of Dungeons and Dragons 5e.

We all know that planning D&D sessions is tough. Most of us do it only so we can play the session. There are those few of us who are masichists at heart and enjoy the torture, but I’m not talking to those freaks today.

Instead, I’m talking to the other freaks who don’t necessarily love preparing for D&D sessions, but still love playing the game and being a DM anyways.

You’re probably asking the question, “How much should I plan for my D&D session?”

You’ve got lots of things to worry about in your life. You probably have a job, kids, a spouse, other hobbies, your physical fitness, dog, parents, friends, and everything else that’s going on in your life. 

You can’t plan every move your players would ever make. 

Well, I’m gonna give you a simple answer and a more complex answer. 

The simple answer is you should plan more than you think you should but less than your players think you have.

Simple right. 

Well, let’s unravel that just a little bit.

1. Plan to finish what you’ve started.

I’ve covered this before, but you need to plan to finish what has been started in the last campaign. This is the minimum requirement. Right now in the campaign I’m leading with my players, I have two characters who just started two separate combat encounters while the rest of the party is back at camp trying to long rest. So naturally, I have to prepare these two separate encounters. For me that looks like reading into the capabilities of the adversaries that will be fighting my players and making sure I know what they can do and what they will most likely do. This also means thinking of the motives behind my players and their enemies to try and guess the most likely way things will go. But, knowing my players, it’s likely that I can’t predict what they will do and that’s ok.

1. 2 -3 Paths.

After finishing these two encounters, I’ll likely have an opportunity to ask, “What do you want to do now?” That means the players will have to think about all the many options they have to do stuff and pick something. Again, there’s no possible way I can predict everything they are going to do. So I pick three possible paths that the players can choose. I’m not really at liberty to discuss the paths I’m preparing for my group now because one of the players is now a host on the this show (aka Cayden Ottley). 

1. Random Encounter Fodder

It also helps to have some tables for random encounters in your back pocket. If you are playing a premade campaign, they’ll likely have some made for you. I think it’s also fun to add in IF - Then situations. For example. One of my players has a certain homebrew item that I gave to her many sessions ago. Since she attuned to it, I’ve had her keep track of how many monsters she’s killed with it. She finally reached 10 kills. Because of that, it’s triggered something new that will happen in the next session when she falls asleep. You can create all sorts of If - Then situations to help you plan what happens. If Player So and So does This and That then the Unexpected happens. 

1. Finish the next path stepping Stone.

I say a good rule of thumb is to plan past at least one next major stepping stone. There’s a chance you won’t finish it, but on the off chance you do, at least you’re ready. This means that at a minimum you have a general idea of everything that happens in the dungeon for example. You know where the rooms are and you know how it’s all gonna go down (more or less, usually a lot less).

1. Remember it’s a skill.

Planning D&D sessions is above all else a skill and therefore requires practice. There will be sessions where halfway through you realize you have nothing else prepared. That’s ok. There will also be sessions where you finish the night and realize you didn’t get to half of what you had prepared. That’s an awesome feeling. As you go through playing D&D you’ll learn instinctually how much to plan for each session.

1. It all has to relate to the players

In listening to Writing Excuses this week (that’s a podcast about writing books), the hosts talked about world building. They said that everything you build for the world is only interesting in as much as it relates to the characters who are infinitely more interesting. I say prepare as much as you want to, but always make sure it relates back to the characters and the players. Get the essentials down (what’s going to happen next session) and then prepare some fun stuff for your players. 

Some people say if it stops being fun then stop prepping, but at the same time, prepping has to get done, so I say, use your best judgement and just try your hardest with it.

I hoped you liked today’s episode. If you would like more of today’s content, then sign up for our newsletter. https://how-to-be-a-better-dm.captivate.fm/subscribe You can even sign up to play D&D with me!

Thanks again for listening to today’s episode. Come back next week for another amazing show.

Until then, let’s go ahead and roll initiative.

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