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Rethinking RPG D&D Session Planning with AI: A New Approach for the Modern GM

Writer's picture: Danny McKeeverDanny McKeever

Updated: 5 days ago

Rethinking RPG Session Planning with AI: A New Approach for the Modern GM
Endless possibilities woven by the storyteller.

Session prep has always been a balancing act—managing time and effort while creating a structured plan that still allows players to take the story in unexpected directions. GMs often face the challenge of preparing enough without over-preparing, ensuring the game stays engaging without becoming rigid. AI tools provide a way to rethink this process, helping game masters streamline their workload while focusing on storytelling, character connections, and meaningful choices.


What’s Inside This Blog:

  • How session planning has changed – A look at traditional preparation methods and their limitations.

  • Using AI to personalize the experience – Ways to integrate player backstories and character arcs into the game.

  • Building encounters with multiple outcomes – Planning for combat, negotiation, stealth, discovery, and avoidance.

  • Creating deeper NPCs and villains – Giving them real motivations, layered personalities, voices and evolving goals.

  • Enhancing in-game improvisation – How AI can assist with on-the-fly adjustments when players take an unexpected path.

  • A new session prep checklist – An updated version of the Lazy Dungeon Master approach, adapted for AI-powered play.


Game masters don’t need to spend hours scripting every detail. With the right tools, preparation becomes faster, more flexible, and more engaging.


 
 

The Traditional Way: Session Preparation with The Lazy Dungeon Master Approach

One of my favorite books is Sly Flourish's Return of the Lazy Dungeon Master. It completely changed the way I approached my session prep. I structured my entire OneNote around his process, using it as a guide to plan each session. If you don't have one, you should pick one up. For it provides a great way to think through the details of each step.


My preparation started days in advance—sometimes even a full week before the game. I would sit down and begin thinking through what the next session would look like. I’d reach out to my players, chat with them about their characters, and gather feedback on what they were interested in exploring. I would write documents, gather images, generate maps, capture notes and organize them in a way that I could access for the next session. This helped me shape the flow of the session well ahead of time, allowing me to outline key events and then step away to let ideas percolate.


A few days later, I’d return to my notes and use Sly Flourish’s session prep checklist to flesh out the details:

  • Review the Characters – Revisit backstories, motivations, and player goals.

  • Create a Strong Start – Plan an engaging opening to draw the players in.

  • Outline Potential Scenes – Structure key encounters, locations, and decision points.

  • Define Secrets & Clues – Scatter bits of information the players might uncover.

  • Develop NPCs – Create allies, villains, and minor characters.

  • Choose Relevant Monsters – Pick enemies that fit the story and challenge level.

  • Select Magic Items – Plan potential rewards for the party.

  • Improvise and Adapt – Be ready to react when things go off track.


While this structure works well, it can be exhausting, for I like details. I always believed in the devil is in the details and taking the time to think through the details matter. There are parts of prep I genuinely enjoy—developing encounters, designing creatures, and tying everything into the larger story arc. But then there are the parts I dread—writing detailed descriptions, crafting dialogue, and making each NPC feel unique.


Take taverns, for example. How many GMs follow the same basic template? Two stories, bar downstairs, rooms upstairs, a bartender, a cook, a couple of waitresses, and a handful of patrons. It’s easy to fall into this routine because creating a truly memorable, well-thought-out tavern experience takes a lot of effort. That’s why I own books filled with premade taverns—sometimes, it’s just easier to pull from a list than to create something from scratch.


The Problem with Traditional Prep

No matter how much I prepared, I seemed to not do enough prep, and the session always went sideways. Players asked unexpected questions. They focused on minor details I hadn’t considered. They skipped encounters, forged alliances with enemies, or latched onto an NPC I had barely named.


That’s where improvisation came in—one of the best parts of running a game. But improvisation is only as good as what I can come up with in the moment.


Flat Encounters & Forgettable NPCs

Some encounters lacked depth. They were straightforward combat or social interactions without layers or alternate solutions. Players either fought, negotiated, or walked away, but rarely was there a moment of real impact.


NPCs were even worse. I would name them on the spot, but they often had:

  • No real personality – Just a voice I had to invent on the fly.

  • No distinct descriptions – A basic role (“merchant,” “guard,” “noble”) but little more.

  • Simple, reactionary dialogue – Responses that lacked depth because I hadn't thought about who they really were.


This made some moments feel flat—like placeholders instead of living, breathing characters.


The "I Should Have..." Moment

About 30 minutes after the session ended, an idea would always hit me:


💡 I should have had the villain say this.

💡 That NPC should have hinted at the deeper mystery.

💡 I could have given them this information in a way that felt more organic.

💡 That random shopkeeper could have been a recurring character instead of a throwaway. 💡 I should have made that combat more memorable by adding a unique twist.


No matter how much time I spent preparing, there was always something I had missed.


How AI Changes Everything

AI became my "what if" assistant. It helps me think through different possibilities long before the session starts. It suggests how I can deepen my story, create interesting twists, build meaningful NPCs, and create tension that feels real.


AI acts as a creative writing tool, helping me refine dialogue, plot twists, and foreshadowing. It does the work that I hate doing.


AI is my image storytelling artist, generating vivid descriptions that make my world feel alive. It allows me to prepare not just better—but smarter.


With AI, I can:

Create Attention Grabbing Tensions – Generate deep and interesting tensions through opposing organizations.

Develop Rich PC Backstories – Generate backstories the tie the players to the world.

Make NPCs richer – Give them goals, relationships, and a real presence in the world.

Build Encounters with Depth – Plan for multiple outcomes, not just one or two.

Create Items with Purpose – Items can now be tied to my story and have meaning.

Generate Descriptions on Demand – No more “uhhh, he looks like... a guy in a cloak.” Develop Amazing Images – They say an image is worth 1000 words, a powerful image really helps to set the tone for the encounter.

Preempt the "I Should Have..." moment – By thinking through scenarios before the session, instead of after.


By using AI to simulate different outcomes, refine character interactions, and generate immersive details, I walk into each session feeling more confident than ever. And even when the game goes sideways (because it always does), I know I have a powerful tool that helps me pivot quickly.


The traditional way worked—but AI takes it to another level.


"AI is a very smart assistant, but it doesn't know about your campaign, session, or specific scenario, thus you need to teach it before you interact with it." - DM

The Ultimate AI-Powered Session Prep Checklist

An updated version of The Lazy Dungeon Master method, enhanced with AI tools to make session prep deeper, smarter, and more adaptable.


1. Review Previous Session Notes & Player Feedback – What Needs to Be Pulled Forward?

🔹 Traditional Method: GMs rely on memory or scattered notes to recall past events.

🔹 AI-Powered Enhancement: AI serves as an organized session tracker, ensuring continuity and narrative depth. I frequently create items, from books to maps, trinkets to scrolls, which often require further development once the players access them.


✅ Identify unresolved story elements – foreshadowed events, plot threads, and open mysteries.

✅ Track player-driven elements – books, artifacts, or knowledge gained that require further development.

✅ Review session notes and player feedback – understand where players want to take their characters next.

✅ AI assists by surfacing forgotten details that should be referenced in the upcoming session.


💡 "AI, summarize key events from the last session and suggest ideas on how I might key elements play out in future sessions that align to my players current story arcs. Give me 3 options for each of my players."



2. Review the Characters – Understanding Their Backgrounds and Motivations

🔹 Traditional Method: GMs manually track character backstories, motivations, and ongoing arcs.

🔹 AI-Powered Enhancement: AI serves as a campaign journal, tracking relationships, unresolved threads, and character development. It helps me create encounters that moves my players through their own story arc. I recently pulled forward an event that happened in session 1, it was a personal experience, into session 38 some 24 months later. The player was blown away.


✅ Encounters that are meaningful for my players tied to their personal quest hooks and/or tied to player choices.

✅ AI can help surface reminders of past events that can resurface in future sessions.

✅ Use AI to think through the Rule of Cool. The Rule of Cool states "Wouldn't it be cool if player x was able to do {insert cool thing} this session."


💡 "AI, remind me of past NPCs Player X has interacted with. How could I bring one back in a dramatic way?"

💡 "AI, in the upcoming session generate for me 3 interesting scenarios that I might present to {player x} to better engage their character."



3. Create a Strong Start – Setting the Hook for the Session

🔹 Traditional Method: GMs pre-plan an opening to draw players into the story.

🔹 AI-Powered Enhancement: AI suggests multiple opening scenes based on past sessions and character actions. AI can help you come up with unique and different openings that avoid cliches and common tropes.


✅ AI-generated openings for the start of the next session that relate to the previous session

✅ Unique alternate opening scenarios prepared if players take unexpected actions.


💡 "AI, generate three unique and compelling opening scenes based on last session’s cliffhanger, avoid common fantasy cliches and tropes. Think through what the players may learn, NPCs we might introduce, or a twist that might be revealed."



4. AI-Powered Encounter Planning – Preparing for All Possible Outcomes

🔹 Traditional Method: GMs plan for one or two encounter resolutions (usually combat or diplomacy).

🔹 AI-Powered Enhancement: AI enables GMs to plan for five possible encounter outcomes and create images that bring to life each encounter. When I run my session, each encounter, NPC, foe, item, or experience has an image that I will share during the session. I can pop that image up on the players screen giving them a sense of what they are experiencing.


✅ AI helps the GM identify the most likely choice players will make and fleshes out that outcome in detail.

✅ AI allows me to easily save pre-planned notes into ready to go chats.

✅ AI allows quick improvisation if players go off-script.

✅ AI generated images to help me story tell around each encounter.


Possible encounter outcomes:

  • Combat – Players fight.

  • Parley – Players negotiate or deceive.

  • Sneaking Past – Players avoid confrontation.

  • Discovery – Players learn something crucial without engaging.

  • Avoidance – Players bypass the encounter entirely.


💡 "AI, generate five different resolutions using the 5 outcomes, (Combat, Parley, Sneaking, Discovery, Avoid) for the bandit ambush and suggest a diplomatic twist."


5. Outline Potential Scenes – Structuring the Flow of Encounters

🔹 Traditional Method: GMs manually plot out key events and transitions.

🔹 AI-Powered Enhancement: AI can suggest possible future encounters and outcomes, generate "random" pre-built encounters and help the GM adapt to anticipates player decisions.


✅ AI suggests encounters and scenes, provides transitions and alternate pathways.

✅ AI adapts to unexpected player actions and fills narrative gaps.


💡 "What happens if the players refuse to go to the haunted ruins? How might I draw them in, give me 3 ideas to make sure the players engage with this encounter that feel natural."


6. Define Secrets & Clues – Laying Breadcrumbs for Discovery

🔹 Traditional Method: GMs create a list of secrets that may or may not be discovered.

🔹 AI-Powered Enhancement: AI generates dynamic secrets that evolve based on player interaction.


✅ AI builds interwoven mysteries based on character choices, histories, or backstories.

✅ AI suggests alternative clues if players miss a critical piece of information.


💡 "AI, suggest three hidden secrets about this ancient temple and how they can be revealed."


7. Develop NPCs – Building Allies and Enemies

🔹 Traditional Method: GMs create static NPCs with pre-determined dialogue and motives.

🔹 AI-Powered Enhancement: AI generates layered NPCs with dynamic motivations, quirks, and real-time dialogue options. Adding the NPC or enemy to an organization that has goals and objectives gives it reason to behave the way it does.


✅ Structured organizations that give NPCs and enemies proper motivation.

✅ AI saved motivations and chats that are trained on important NPCs, AI is the voice of the NPC.

✅ NPCs with evolving goals based on player choices.


💡 "Give me a quiet, friendly merchant NPC who secretly works for the thieves’ guild. What motivates him to work for the thieves' guild, secretly, how does he perceive the PCs and what is he willing to do to thwart their efforts?"



8. Choose Relevant Monsters – Balancing Encounters

🔹 Traditional Method: GMs select monsters that fit the setting and balance the challenge rating.

🔹 AI-Powered Enhancement: AI tailors monster choices to player tactics and character backgrounds. This helps keep their players on their toes.


✅ AI-created complex enemies. From behaviors, dialog, story arc alignment and unique battle tactics all help to bring the enemy to life.

✅ AI-driven encounter pacing adjustments.


💡 "How can I make this werewolf encounter more cinematic and personal for my barbarian player?"

💡 "Generate for me a CR4 werewolf with a complete stat block, ability scores, interesting features and quirk that is related to the campaign."


“A good villain doesn’t see themselves as evil. They see themselves as the hero of their own story.” – Drew Goddard

9. Select Magic Items – Rewarding Players

🔹 Traditional Method: GMs pick items that match the story and progression balance.

🔹 AI-Powered Enhancement: AI generates items tied to character themes and world lore.


✅ AI-created custom artifacts with meaningful lore.

✅ Items that reflect character growth and campaign themes.


💡 "Give me a magical sword linked to my paladin’s lost family and suggest 3 ways in which this aligns with the current campaign story arc."


10. Monster Review – Seeing the Session Through Their Eyes

Another one of my favorite books is The Monsters Know What They’re Doing: Combat Tactics for Dungeon Masters by Keith Ammann. This book changed the way I approach encounters, pushing me to consider not just what monsters are, but how they think and fight. By stepping into their perspective, a GM can make every battle more real, dynamic, and challenging—without just increasing numbers on a stat block.


I once forced a party of five 3rd-level players to turn tail and run when they faced three goblins. Not because the goblins were stronger, but because they used terrain, tactics, and ambush strategies that caught the players off guard. This forced the party to rethink their approach and adapt, making for a far more engaging and memorable encounter.


Traditional Method: Monsters as Set Pieces

Most of the time, GMs select monsters based on difficulty ratings and whether they fit the theme of the encounter. They calculate challenge levels, maybe tweak a stat or two, and move on. But monsters don’t just stand there waiting to be fought. Intelligent creatures strategize, ambush, retreat, and regroup. Even mindless creatures have instinctual survival tactics.


AI-Powered Enhancement: Training AI to Think Like Your Monsters

Instead of simply picking a monster, AI allows the GM to train the AI on how the monster thinks. By tying monsters to organizations, cultures, and battle tactics, AI can help develop:


Layered defenses – How would an intelligent creature fortify its lair? What traps, choke points, or escape routes would they prepare?

Ambush strategies – What would goblins do if they had time to prepare? How would a beholder manipulate the battlefield?

Coordinated group tactics – How does the bandit leader rally their forces? How does a hobgoblin warband position archers and shield-bearers?

Adaptation to player actions – If the players wipe out a scouting party, how does the main force adjust their battle plan?


Instead of increasing hit points, AC, or adding extra abilities, AI helps GMs think through layered, tactical responses. This makes encounters more difficult not because the numbers are bigger, but because the enemies are smarter.


💡 "AI, how would this mind flayer approach a battle where it is outnumbered but has home-field advantage, make sure to include its minions, and intelligence that it might gather ahead of time? Give me 3 options to consider."


By using AI to simulate intelligent monster tactics, GMs can create encounters that force players to think, adapt, and strategize, rather than just roll dice and attack. A well-planned fight with three goblins can be more terrifying than an unprepared brawl against a dragon.


Organizations are not just a collection of NPCs waiting for the PCs to show up. They are living, breathing entities with plans, shifting alliances, and a strong will to succeed. By training AI on what these organizations believe in and how they operate, a GM can easily bring intelligence and complexity to them.


11. Improvise and Adapt – Letting the Players Shape the Story

🔹 Traditional Method: GMs must react in real time with minimal tools for on-the-fly storytelling.

🔹 AI-Powered Enhancement: AI serves as an improvisational tool, generating NPC responses, unexpected twists, and new paths instantly. It helps the GM prepare for those sideways encounters and react to the players actions.


✅ AI-trained NPCs with pretrained conversation trees and reactive NPC conversations.

✅ Adaptive session tools that adjust based on player actions.


💡 "The players just killed the crime boss. AI, how does the underworld react? Give me 3 ways that these organizations, {insert org}, {insert org} and {insert org} would react to the crime boss being killed."



The Future of RPG Prep Is Here

AI isn’t about reducing preparation—it’s about enhancing storytelling and making sessions more immersive, flexible, and engaging.


New Session Checklist:

Review previous session notes & player feedback – Track unresolved plot points, foreshadowing, and character feedback to keep the story moving.

Review the characters – Keep player backstories, motivations, and personal quests at the center of the campaign.

Create a strong start – Generate compelling openings that hook players from the first moment.

Plan encounters with multiple outcomes – Prepare for combat, diplomacy, stealth, discovery, and avoidance so players always have choices.

Outline potential scenes – Anticipate key moments and transitions, while staying adaptable to player decisions.

Define secrets & clues – Ensure mysteries unfold naturally and that missed clues can be uncovered in new ways.

Develop NPCs – Give characters real motivations, evolving goals, and dynamic dialogue that reacts to player actions.

Choose relevant monsters – Select enemies that fit the world and challenge players in strategic ways.

Select magic items – Introduce meaningful rewards tied to character stories and campaign themes.

Monster review – Seeing the session through their eyes – Think like the creatures, build tactical encounters, and make battles feel real without just boosting stats.

Improvise and adapt – Use AI as a real-time assistant to respond to unexpected player choices on the fly.



With AI, GMs don’t just prepare more efficiently—they prepare smarter. The result is a game that feels alive, challenges players in new ways, and stays flexible no matter where the story leads.


Tools of the Trade

Bringing AI into session planning isn’t just about ideas—it’s about using the right tools to make preparation smoother, faster, and more immersive. Here are some of the best tools for building, running, and enhancing RPG campaigns:


The Game Master Platform – A powerful tool for building and running campaigns, managing encounters, and keeping everything organized.

ChatGPT & ChatGPT Projects – Perfect for fleshing out details, generating story ideas, and storing campaign notes in an interactive way.

NotebookLM – A free AI-driven tool that allows GMs to organize, reference, and interact with campaign and session notes effortlessly.

Midjourney – An AI-powered art tool for creating and finding immersive images to bring your campaign world to life.


By combining these tools, GMs can streamline preparation, enhance storytelling, and create deeper, more engaging worlds—without spending hours bogged down in tedious prep work.

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