A Simple D&D Session Structure to Help Prepare Your Sessions

You all finish your long-rest and you wake up to a bright, if not bitter cold winter morning. The view from the mountaintop lookout on which you slept is breathtaking, as is the chilling wind that blows. You all slept comfortably thanks to the warmth of the fire.

As you all wake up you prepare for the day, memorizing your spells, stretching your sore limbs and generally preparing yourselves for whatever may come next, except one of you.

Roen the druid, as you wake up you are met with the sight of a small brown squirrel sitting before you, patiently waiting for you to awaken. Tied around the squirrels neck is a tiny scroll of parchment.

Naturally, you reach down and untie the scroll and unroll it. As you do, the squirrel scampers off into the trees.

The scroll is very small yet is crammed with writing. The writing is clumsy as if it was written with charcoal rather than a quill and ink. 

On the parchment is a line of text that turns your heart to ice.

“Help. Captured by Xyxyx in Waterdeep. Cynthia.”

And that is where we will end today’s session.

Welcome back to the 29th episode of How to Be a Better DM. I’m your host, Justin Lewis and I’m here to help you craft better stories for yourself and your players as you DM Dungeons and Dragons 5e.

Before we get to the show let’s go through a couple of announcements. 

First, I hope you all enjoyed our last episode where you all met our new team member, Tanner Weyland. If you have any comments or questions for him or me, send us a direct message at @geronimolevis through Instagram.

Next, today’s show is brought to you by our monthly newsletter.You can sign up using the link in the show notes and get access to extra tips on being a DM, behind the scenes content and extra homebrew pieces that you can use in your campaigns. You can also sign up to play a one-shot with myself as your DM. This is first come first serve so sign up for the newsletter and let’s play a session together.

Now, to the show.

Planning your sessions can often be the most difficult part of playing D&D. Sometimes it helps to have a general structure to your sessions. Well let’s look at this simple D&D structure.

1. What happened last time

One of the most important things you can do to start off a good session is a recap of the session before. This gives your players a chance to get into character and into the game. It also serves as a nice way to transition out of friendly chatter and into playing a game where you have to be quiet while the DM talks. Lastly, it’s great to remind your players what happened last because they’ve probably forgotten. 

1. Resolve what happened last time

Finish what you started last time. If you had just started an encounter, then run the encounter. If you left off on a cliff hanger then run through what implied the cliff hanger. Sometimes though, it makes for a nice twist to not resolve what you started but that is an advanced technique.

1. Ask about Character’s Backstories

At this point, ask if every person’s back story has been featured lately. If not, add in something that relates to the backstory of someone. It doesn’t need to be in depth but it can be. 

1. Add the next main plot point

Think about the next logical plot point and prepare that. Pretty simple. Just beware, you will not be able to plan for everything. I like to ask myself the question, “What would I logically do next?” And then I prepare for that. Then I ask myself, “If I didn’t do that, what would I logically do?” Then I prepare for that. Then we end up doing neither of those things and doing something completely random that my players came up with at the moment. Se la vie.

1. Prepare at least one encounter

Most often your players expect to fight something  So I find it helpful to have at least one combat encounter in my back pocket. The best way to do this is using D&D Beyond’s encounter builder. It’s a great way to save an encounter and then go in and tweak it a bit when things have changed but you still need an encounter.

1. Plan for the cliffhanger

The last thing you want to do is plan for a probable cliffhanger. I say probable because there’s no way of knowing exactly where the session will end. You’ll have a lot of input but so will the players. For me good cliffhangers are right before big encounters, or right after a reveal of something, or when there’s a twist. You’ll want to be thinking about your cliffhanger during the session so that you can prepare for it and possibly even change it.

There you go, a simple session structure that should help you figure out what your players will be doing next session.

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Come back next week for an amazing episode but until then, let’s go ahead and roll initiative.

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