The GM’s Eternal Struggle with D&D Player Unpredictability
You’ve mapped out the dungeon, built out the villain’s motivations, and prepped for an epic showdown. The party walks in, and instead of fighting the bandits you carefully balanced, they charm the leader into starting a roadside tavern. Or they bypass the whole thing with a clever use of Misty Step and a grappling hook. Sound familiar?
Every GM has been there—the players zig when you expected them to zag. That scramble to adjust on the fly can stall the session, break immersion, and leave you flipping through your notes trying to figure out what happens next. It’s part of the magic of D&D, but let’s be honest: it can also be stressful.
But what if you had a tool that helped you prepare for all those unexpected twists? AI isn’t here to run the game for you, but it can help you stay ahead of the chaos. By using tools like ChatGPT, ChatGPT Projects, NotebookLM, and The Game Master Platform, you can prep encounters that cover multiple player choices—combat, negotiation, stealth, discovery, or even avoiding the encounter altogether. You’ll be ready no matter what wild ideas your players throw at you.
As the old saying goes, “No plan survives first contact with the players.” But with a little help from AI, you can make sure the story keeps rolling, no matter where your players take it.
The Five Outcomes of Every RPG Encounter
In Dungeons & Dragons, players have a reputation for being unpredictable. While their choices might seem endless, most encounters boil down to five broad outcomes. Understanding these categories helps GMs prepare for whatever path the party decides to take, ensuring the session stays engaging and immersive.
Here’s a breakdown of the five outcomes and how they shape the encounter:
1. Combat: When Words Fail, Swords Speak This is the most common and straightforward outcome—players choose to fight. Whether it’s a planned ambush or an argument that escalates into violence, combat encounters need more than just hit points and stat blocks. Think about how enemies use the environment, retreat tactics, or reinforcements to make the battle feel alive.
Example: The party confronts a corrupt city guard. Instead of talking, they draw steel, leading to a brawl in the crowded streets where bystanders flee, and more guards are summoned.
2. Parleying: Talking Their Way Out Sometimes, players prefer words over weapons. They might negotiate, bribe, or deceive their way through an encounter. Parleying adds depth to interactions, requiring GMs to think about what NPCs want, what they fear, and how far they’re willing to bend.
Example: The same corrupt guard might accept a bribe to let the party pass—but at a cost. Maybe he sells them out later or strings them along for more gold.
3. Sneaking: The Silent Approach When players want to avoid confrontation altogether, stealth becomes their tool of choice. Sneaking requires GMs to think about patrol patterns, guard awareness, traps, and the risks of being caught. It’s about building tension and rewarding creative problem-solving.
Example: The party spots the checkpoint ahead and decides to sneak around. AI can help design guard rotations, hidden paths, or environmental obstacles that make the stealth route feel challenging and rewarding.
4. Discovering: Uncovering Hidden Details Curious players often focus on their surroundings, searching for clues, secrets, or lore. Discovery outcomes transform simple encounters into opportunities for world-building. GMs can hide bits of the story in the environment, encouraging players to dig deeper.
Example: While others argue with the guard, a party member notices a strange insignia on his armor. Further investigation might reveal his ties to a local crime syndicate, opening new plot threads.
5. Avoiding: Skipping the Encounter Entirely Sometimes, the players don’t want to engage at all. They might find a clever workaround, use a spell, or simply choose a different path. Avoidance can be tricky for GMs, but when handled well, it keeps the world feeling reactive and alive.
Example: Instead of facing the guard, the party remembers a rumor about an old smuggler’s tunnel beneath the city. AI can help flesh out this alternate route, making sure their choice feels just as meaningful as a confrontation.
"The best GMs aren’t the ones who prepare for everything—the best GMs are the ones prepared for anything." — Matt Mercer, Critical Role
Here is an encounter that I recently ran. Sewn Sisters 1: The Gateway Hall. I saved off a chat just for this encounter, prompting the AI to give me 5 options for each outcome, Combat, Parley, Sneaking, Discovering, and Avoiding.
Check out our free eBook “Taking Your D&D Encounters to the Next Level Using AI” for more tips, tools, and examples.
Why Preparing for Only One or Two Outcomes Falls Short
Most GMs start out planning encounters the same way: expect a fight or a conversation, and maybe prepare a backup plan if things go sideways. This works—until it doesn’t. Players are unpredictable by nature. They’ll climb walls you didn’t describe, negotiate with monsters you thought were unredeemable, or sneak past an encounter you spent hours balancing. When you’ve only prepared for a couple of outcomes, those unexpected choices can throw a wrench in the session.
"The dice might be random, but your players? They're pure chaos." — Every GM Ever
The Traditional Approach: GMs often build encounters around a specific solution. Maybe there’s a monster blocking the path, so combat seems inevitable. Or a suspicious merchant holds vital information, leading to a clear conversation. But what happens when the party refuses to engage? Or tries something unexpected, like bribing the monster or tricking the merchant into a confession with an illusion spell?
When Players Go Off-Script: Let’s say the party reaches a guarded checkpoint. You’ve prepared two outcomes:
Combat – The party fights the guards.
Negotiation – The party talks their way through.
But instead, they choose to sneak through the sewers, or they avoid the encounter all together by taking the long way around. Without preparation for these outcomes, you’re left scrambling to invent details on the fly. This can stall the game, break immersion, and make the encounter feel flat.
The Fallout of Limited Preparation:
Session Flow Breaks: When players choose an unprepared path, GMs may pause the game to improvise, disrupting momentum.
Immersion Takes a Hit: Quickly cobbled-together responses can feel out of place or inconsistent with the world, pulling players out of the story.
Encounters Feel Shallow: If every situation funnels into the same outcomes—fight or talk—players start to feel like their choices don’t matter.
How AI, Like ChatGPT, Helps You Prepare for All Five Outcomes
As GMs, we’re used to juggling possibilities, but there’s only so much we can predict before the session starts. That’s where AI comes in—not to run the game for you, but to act like a co-GM, helping you think through different outcomes quickly and creatively. Tools like ChatGPT, NotebookLM, and The Game Master Platform can simulate player behavior, offering fresh ideas for how encounters might unfold.
"A good GM plans for chaos. A great GM makes chaos part of the plan." — Unknown
Thinking Through Every Possibility AI tools can help you explore how an encounter might play out across the five outcomes—combat, parleying, sneaking, discovering, or avoiding. Instead of only preparing for a fight or a simple negotiation, AI helps you brainstorm what happens if the players try something unexpected. It’s like having a sounding board that doesn’t get tired of your “what if” scenarios.
Simulating Player Behavior Players are unpredictable, but AI can help you anticipate their moves by simulating how different characters might react. Whether you have a sneaky rogue, a silver-tongued bard, or a curious wizard in your party, AI can suggest ways those archetypes might approach an encounter. This lets you prepare for multiple paths without having to invent everything on the spot.
Example: Turning a Bandit Ambush into More Than Just a Fight Let’s say you’ve set up a classic ambush—a group of bandits jumps the party on a forest road. Traditionally, this would lead straight into combat. But with AI, you can explore other possibilities:
Combat: The bandits might use guerrilla tactics, striking from the trees and retreating to lure the party into traps. AI can suggest creative tactics based on the terrain or even the bandits’ personalities.
Parleying: What if the bandits are desperate? AI can help flesh out their motivations, maybe suggesting they’re starving villagers turned to crime, opening the door for negotiation—or betrayal.
Sneaking: The party’s scout might spot the ambush before it happens. AI can help design guard patrols, environmental obstacles, and the consequences of getting caught mid-sneak.
Discovering: Maybe the party notices strange markings on the trees, hinting that this isn’t just a random attack or a location of frequent ambushes. AI can weave in lore or clues that tie the bandits to a larger plot.
Avoiding: The party could find an old hunter’s trail that bypasses the ambush entirely. AI can suggest how this choice impacts future encounters—perhaps the bandits now hold a grudge, setting up a later confrontation.
Save and Organize Notes for Quick Reference During the Session
Once you’ve used AI to prepare multiple outcomes for an encounter, the next step is to organize those ideas in a way that’s easy to access mid-session. There’s nothing worse than flipping through pages of notes while your players stare at you, waiting for the next move. Keeping your notes clear and structured lets you stay in the flow of the game, no matter what direction the players take.
How to Organize Your Encounter Notes:
Label Each Encounter and Outcome Clearly: Break down the encounter into the five possible outcomes—Combat, Parleying, Sneaking, Discovering, and Avoiding. This way, when players make their choice, you can jump straight to the right section.
Use Bullet Points for Key Details: Keep your notes brief but informative. Bullet points make it easy to scan for important info like NPC motivations, environmental hazards, or plot hooks.
Highlight Consequences: For each outcome, jot down how the players’ choices will ripple through the story. This helps you stay consistent and makes their decisions feel meaningful.
Store Digitally for Quick Access: If you’re using tools like ChatGPT Projects, NotebookLM or The Game Master Platform, to keep your notes organized by encounter, each powered by AI allowing for quick reactions and detailed responses to any question. This saves time and keeps everything at your fingertips.
Example: The Party Encounters a Corrupt City Guard at a Checkpoint
Here’s how AI can help you prepare for all five outcomes and organize the results for quick reference during the session.
Combat:
The guard calls for reinforcements from nearby outposts.
AI suggests using the city’s narrow alleyways to create chokepoints, forcing the party into a trap and combat.
Consequence: The party becomes wanted criminals, making future city encounters more dangerous.
Parleying:
The guard hints at accepting a bribe but has ulterior motives.
AI suggests he takes the gold but later tips off a local crime boss about the party’s presence.
Consequence: The party gains a temporary ally in the guard but earns a new enemy in the crime syndicate.
Sneaking:
AI helps design the guard’s patrol schedule and suggests specific environmental obstacles (e.g., loose cobblestones that could give away footsteps).
If caught, the guard sounds an alarm, leading to a tense chase through the streets.
Consequence: Successfully sneaking past avoids immediate conflict but leaves the guard suspicious, tightening security for future encounters.
Discovering:
While interacting with the guard or exploring the area, players might find hidden documents linking him to a larger crime network.
AI helps flesh out these connections, providing clues that tie into the campaign’s bigger story arc.
Consequence: The party gains leverage over the guard, opening up new roleplaying opportunities.
Avoiding:
AI suggests an old, crumbling tunnel beneath the checkpoint that offers a risky way around.
The tunnel might be unstable or inhabited by something worse than the guard.
Consequence: The party bypasses the checkpoint but faces new dangers underground.
The Benefits of Preparing for Multiple D&D Encounter Outcomes
When you prepare for every possible player decision, your game runs smoother, feels richer, and keeps everyone more engaged. Here’s why thinking through multiple outcomes is a game-changer:
Confidence: There’s nothing more stressful than scrambling for ideas when your players throw you a curveball. With AI-assisted prep, you’re ready for anything. You’ll feel more in control, even when the session takes an unexpected turn.
Engagement: Players thrive when they know their choices matter. When the world reacts naturally to their decisions—whether they negotiate with the villain, sneak past the guards, or uncover hidden clues—it keeps them invested in the story.
Depth: Encounters stop feeling like one-off events and start feeling like part of a living world. When each outcome ties into the broader story, your players experience a game that’s not just reactive but deeply connected.
Check out our free eBook “Taking Your D&D Encounters to the Next Level Using AI” for more tips, tools, and examples.
"A D&D campaign isn’t just a series of battles and treasure hunts—it’s a story where the players shape the world, and the world shapes them right back." — Chris Perkins, Dungeons & Dragons Lead Story Designer
Conclusion: Embracing the Chaos with AI as Your Co-GM
Unpredictability is what makes D&D unforgettable. It’s the wild plans your players hatch, the unexpected alliances, and the moments where you, as the GM, sit back and think, “I didn’t see that coming.” That’s the magic of the game. But keeping up with that chaos can be exhausting.
AI tools like ChatGPT, NotebookLM, and The Game Master Platform don’t take the creativity out of your hands—they amplify it. They help you prepare for the twists and turns, giving you the flexibility to lean into your players' choices without missing a beat.
So, the next time your party decides to talk to the dragon instead of fighting it, or bypasses the dungeon entirely, you’ll be ready—not just to react, but to make their unexpected choices feel like part of the story all along.
Call to Action: Want to take your encounters to the next level? Check out our free eBook “Taking Your D&D Encounters to the Next Level Using AI” for more tips, tools, and examples. And if you're ready to bring your stories to life, explore The Game Master Platform to see how AI can transform your sessions.
Great article! As a long-time DM, AI is demonstrated to be great at creating "stuff." It's also good, like you've said here, for alternate outcomes. I'm pretty good at ad-libbing for crazy player ideas, but are there good tools for running, maintaining, and documenting my campaign?