Session Planning Checklist: How AI Can Help GMs Plan Epic D&D Sessions

Being a Dungeon Master is both rewarding and challenging. You're responsible for setting the stage, controlling NPCs and monsters, and reacting to players' actions. Now imagine having an AI assistant, like ChatGPT, Gemini or Claude, these "AI familiars," to help with those tasks. AI can support a DM by handling the fine details, enhancing the creative process, and even improvising when things go sideways.

By now I have created a campaign story arc, developed different plots and sub-plots and now, through the process of playing out the encounters, we write the story.

---

Download The Simple AI Guide to Adventure Building >>

---

Session Structure: Balancing Preparation and Flexibility

A typical D&D session lasts between 3-5 hours and involves 4-7 encounters. I plan these encounters in advance, thinking through what each is about and the potential outcomes. While in my mind I think through the order in which the encounters might happen, but in reality, it never happens in this order.

I also include 1-2 random encounters that I can pull out of my bag of tricks. Usually, I prepare these random encounters to happen during travel or in a town, depending on the flow of the session. These encounters are not random in the sense that they are rolled off of some table in a book, but random in the sense that they may or may not happen.

Blog: 5 ChatGPT Prompt Methods to Prepare for Your Next D&D Session >>

Here is my checklist before I begin my session.

Session Preparation Checklist:

1. Train the AI on the campaign, the encounters and the last session notes: Provide the AI with the campaign’s history, player characters (PCs), and upcoming encounters.

   1. Review previous session notes

   2. Review feedback from my players

2. Reminder Emails - Session reminder emails go out to my players 24 hours before the session

3. Session Outcomes: I think through the possible session outcomes that I would like to see happen. Outcomes that align with the story elements and import plot arcs.

4. Review Each Encounter: Here I review the different pieces of the encounter and if need be complete those pieces for the upcoming session.

   1. Name - Name of the encounter

   2. Overview - This is the overview of the encounter and any GM notes that I might save. It also talks about how it relates to the story.

   3. Images - I save off different images that I will share during the session to help me with storytelling. Not to be to cliche, but a picture is worth 1000 words.

   4. Items - I prepare any interesting items that the players may come across, like books, artifacts, or anything that helps move my story forward.

   5. Maps - GM and players maps to help them navigate the world

   6. NPCs/Villains - I think through a lot or a little detail for each NPC depending on their role in the encounter.

5. Converse and save AI chats for each encounter:

   1. Prepare for the encounter with a description - I want to engage all 5 senses if possible and use this opportunity to try and build an emotional connection with my story.

   2. Plan for different twists, dialogs and outcomes - depending on the encounter I like to introduce a twist to create a surprise, incorporate interesting dialog, a puzzle and different outcomes.

   3. Ask the AI to play the roles of the different NPCs or Villains - this is so powerful, having the AI play the role of your villain in the encounter. It can help you think about battle strategy, develop their personality and/or help write dialog.

   4. Prepare the Rule of Cool and a Strong Start – This sets the session up for success by putting the players first and grabbing their attention in the first 5 minutes, making sure the opening is exciting and immediately engaging.

   5. Payoff – Think about the payoff for the characters at the end of the session. It doesn’t always have to be magical items or treasure; it could be new information, the introduction of a key NPC, or even waking up from a dream.

6. 5 encounter outcomes I use AI to help prepare for: Each encounter will result in one of the 5 outcomes, so I, the GM, will prepare for each outcome.

   1. Parley: The players try to talk their way through the encounter

   2. Trick: The players try and trick their way past the encounter using stealth, ambush, or a lure.

   3. Combat: The players fight their way through the encounter

   4. Discover: The players use information to make their way past the encounter

   5. Avoid: The players try and skip the encounter all together.

7. Post Session: This is one of the most important steps that many GMs skip. Capturing session notes and getting feedback from your players.

   1. I like to use AI to draft detailed session notes, not only to keep track of what happened but to train the AI for use in future sessions.

   2. Post session email goes out with a short survey. I want to hear from my players on how the session went and what they would like to do in future sessions. This feedback is invaluable for me to build engaging sessions for my players

Here is a list of prepared encounters that I have worked through for my one-shot session.

AI helps me manage this balance by providing the flexibility to introduce these encounters seamlessly without feeling disjointed. It also allows me to prepare for sessions with detailed encounter descriptions and potential variations to adapt on the fly.

Here is an example of me preparing to run the first encounter called "Message from the Raven." In the image below the AI Assistant is trained on the overall campaign, the encounter overview and I saved off the initial dialog with the Raven.

AI and Encounter Planning: Filling in the Details

For each encounter, AI helps with the small but important elements. I use it to create vivid descriptions that engage all five senses, ensuring players can fully immerse themselves in the environment. Whether it’s the damp smell of an ancient ruin or the clinking of distant chains, AI can craft sensory experiences that add depth.

AI-generated images are also invaluable, helping to visualize maps, settings, and props. For NPCs and villains, AI assists in developing their backstories and personalities. It doesn’t just stop there—AI helps me create dynamic dialogue, anticipating interactions and preparing unique responses to player actions. It’s like having an extra hand guiding the story.

For example, here is an image of a magical painting that the player character came across when exploring a tower.

Improv and Flexibility: When Sessions Go Sideways

Every GM knows that no session goes exactly as planned. Players take unexpected routes, invent solutions, or dive into unscripted moments. This is where AI shines—providing improvisation tools that fill in gaps, generate new challenges, or even create surprising twists in real time. If players decide to break into an unplanned location or interrogate an unexpected NPC, AI can create a new location, NPC or suggest responses and potential outcomes, keeping the session moving without missing a beat.

By having the AI trained on your campaign and encounters, it knows what is happening because you provided it content and context. Now, after a few thoughtful prompts, you can adapt to any situation that the players throw at you.

Here is an example when the players went in a direction that I was not prepared for. I had an idea of what was in that direction, but I did not have a description. On the fly I asked the AI Assistant to write a short description for me and since it new my campaign and location, it provided me a valid description, here it is.

AI, The Rule of Cool and a Strong Start: Tailoring Experiences for Each Player

One of my favorite uses of AI is for “The Rule of Cool.” I like to create special moments for each player based on their style of play, their character’s background or abilities. AI helps suggest moments of awesomeness tailored to each player, from a rogue's daring stunt to a wizard unleashing a previously unknown spell. These moments create unforgettable experiences for players, making each session feel personal and exciting.

A strong start involves the GM intentionally thinking about how to grab the players' attention in the first 5 minutes of the game. This can be achieved by revealing new information, introducing a new NPC, or starting with an exciting fight.

Here is a session overview page that is showing my "Rule of Cool" planning.

Last-Minute Prep and Final Touches

AI is perfect for last-minute preparations, especially when I need to generate content quickly. Whether I need a final encounter description, a new NPC, or an idea for an unexpected ending, AI can fill in the gaps. It’s a great safety net that ensures I’m always ready for whatever the players throw at me.

Post-Session Review: Using AI for Session Notes

AI is a valuable tool for drafting post-session notes, helping both the GM and players remember important events. It can automatically generate summaries of key encounters, NPC interactions, and plot developments. These notes keep everyone aligned and provide continuity for future sessions.

Each player can see the session date, the session notes and their rating for that session. All of this trains the AI for future sessions.

Additionally, AI helps store player feedback, allowing the GM to understand where players want their characters to go next. This feedback can guide future plot points and character arcs, ensuring a collaborative and satisfying story progression for the entire group.

Here the GM can see all feedback provided across all sessions that were run.

Conclusion: AI as the Perfect Co-GM

AI doesn’t replace a Dungeon Master’s creativity—it enhances it. From planning encounters to improvising when things go off course, or writing session recaps, AI provides the tools to keep sessions engaging and flexible. With AI by your side, you can focus on crafting an unforgettable adventure while letting your familiar handle the details.