Creating Unforgettable D&D Encounters: 9 Critical Tips
Today, it’s time to roll for initiative. Crafting challenging and engaging D&D encounters is not as simple as it may seem. As a New DM it is easy to fall into the pit trap of making your first few encounters fall flat because you simply find a monster you’re stoked to unleash upon your PCs and that is as far in the planning as you get. While it will still be fun, I’ll tell you, from personal experience (whoops) that no matter how badass your monster might be, it takes much more thought and prep to craft a solid encounter that your players will remember, and if you do it right that battle against a dozen gnomes can be more fun, and dynamic than going toe to toe with a Tarrasque. So, here’s nine ways to transform your encounters from bad to rad!
Strike a Balance: Like a skilled bard crafting the perfect melody, finding the right balance in your encounters is crucial. In order to do this, you must first have a solid knowledge of your players’ abilities. By knowing what each Player Character (PC) can do, you can tailor the challenges to, well, challenge them. You want to be able to keep them on their toes with foes that exploit their weaknesses while allowing them to also utilize their strengths.
This means, if you have a villain who is attempting to escape, you make sure you pick something with high wisdom so your sorcerer’s Hold Person spell doesn’t immediately end the chase while making sure it has a lower intelligence so her Tasha’s Mind Whip can lash out 90 feet and deal some serious damage.
By balancing in this way, you will keep them fully engaged and feel rewarded when they eventually leave initiative. Remember, a well-balanced encounter is the foundation of an epic tale, and that’s what we’re all trying to craft as DMs.
Craft Dynamic Battles: There are few things more boring than a battle encounter that is purely hack-and-slash until all the baddies are dead. When crafting a fight, it is important to make sure that there is more for your players to do than just fight, another goal, or obstacle.
Maybe one of your PCs’ friends or family members is being held captive and they have to focus on saving them while also dealing with attackers, and, if they don’t save them in a particular amount of time things get more dire. Or they’ve been tasked with recovering an object, but if they kill the big bad of the week before they recover it it is lost forever.
Having secondary goals will make the battles dynamic and will avoid that terrible feeling when your players pull out their phones until it’s their turn to swing a sword or cast a spell.
Build Purposeful Encounters: This ties directly to dynamic encounters; your encounters should not be mere obstacles to overcome. Infuse them with purpose and meaning, they should always be driving the story forward or dropping a little bit of world-building knowledge that the players can extract later.
Each battle should leave a mark on your players' journey, propelling them forward or revealing hidden truths that shape their destiny. That secret wooden shrine to a group of druids where they battled a group of dryads and blights, well, that wood is a unique wood that they find they need two sessions later, and those druids, if they find them, hold the cure to an illness that is ravaging the countryside 10 sessions from now.
Use your encounters to expand your world, add hints to future missions, and tie in your PCs’ backstories to keep them invested and intrigued.
Mix It Up: Variety is the spice of … adventure! Your encounters should be as diverse as the landscapes they unfold in and the characters that take part in them. Not every encounter needs to be a fight, sure, D&D mechanics lean a little battle-heavy, but there is so much more that you can do in this game.
Thrilling combat is a good mainstay, but alternate in some other options that fit you and your players. Build in some mind-bending puzzles, put those high Charisma PCs in the driver’s seat with diplomatic negotiations, and test those other epic skills with unique, skill-based challenges. Give your players a taste of different flavors, leaving them hungry for more.
Give Your Enemies Personalities: No more one-dimensional foes! Can it be fun to go through and lay waste to a horde of nameless goblins, sure. And that will never stop being fun. But, there needs to be at least one goblin, or their bugbear leader, that your players can interact with. It will seriously up your encounter if you make your baddies as dynamic and interesting as your player characters.
Think about their backgrounds, what drives them, and what makes them tick. Infuse them with real motivations that go beyond just being obstacles to overcome. How about adding some twists during the battle? Maybe they reveal some hidden secrets that surprise your players? Maybe they aren’t that loyal to their cause and they will aid your players if they let them live?
Let your enemies be more than just cannon fodder – make them memorable, and your players will remember the epic clashes for sessions to come.
*A treasure trove of info on this topic can be found over at the wonderful blog by Keith Amman, The Monsters Know What They’re Doing. I highly suggest keeping it in your bookmarks as a regular DM tool.
Be Descriptive: As a Dungeon Master, you are partially a storyteller. A surefire way to have dull encounters is: “Does an 18 hit? It does. Nice. You take 7 piercing damage. Next in initiative is …” It’s easy to be this DM and I’ll admit I have fallen to it myself, especially in battles with tons going on.
Don’t make that mistake. While it may not come naturally to you, a skill you can hone to bring the battlefield to life and watch as your players become fully engrossed in the world you've created is being descriptive. Enhance your encounters with vivid descriptions, immersive details, and atmospheric cues. “That’s an 18 to hit. Fwip! Fwip! Two crossbow bolts soar through the air, and wham! pierce your armor, sending searing pain through your right arm. You take 7 points of piercing damage and look into the tree above to see a shadowy figure reloading. Next up is…”
So much better. And it paints a picture for your players, pulling them, and yourself, deeper into the encounter. I know it’s easier said than done, but with enough experience, your storytelling modifier will increase sooner than you think.
Embrace the Unexpected: Never forget that mischievous third party that accompanies most every TTRPG campaign, the dice. All the planning in the world can’t take into account how those little devils will be rolling on any given day and so when they throw a wrench in your works be ready to capitalize on that unforeseen event.
Your players will demolish your session’s main villain before they get to do anything cool, a nat 20 investigation roll or insight check will let them figure out your big mystery, they’ll walk right past that big encounter you spent hours planning, it’s going to happen. So, be prepared to adapt and improvise as the dice roll, for the most memorable encounters often arise from the unlikeliest of situations.
Build the Stakes: The DMG and Monster Manual have encounter ratings and monster ratings, and when I started out I followed them. I threw some easy and medium-difficulty encounters their way and that was nearly a waste, I did zero damage to anyone in our first encounter and barely any more in our next few.
My suggestion, even if it sounds a bit scary for those of us who don’t want Total Party Kills, is always, always go Deadly. Unless your party is rolling atrociously and/or playing stupidly, they will make it through, and yet, maybe one, maybe two go down and have to be healed during the battle.
And those death saving throws, those, in the end, are what we want. Aren’t they? We want this game to be exhilarating, to give us an adventure that we can’t have in real life, to make us feel alive in a way that life somehow can’t (and if life does get to feeling that way, well, that’s all too terrifying in itself). We want stakes, and nowhere else in this game is it easier, or more fun as a DM to give your players stakes and let them feel the glory of victory once they beat them.
Seize the Drama: On a similar note to raising the stakes, this is what D&D is all about, making moments to remember. Every campaign has its defining moments, those heart-pounding, hair-raising instances that resonate with players long after the session ends. Craft your encounters in ways to make it possible for your characters to seek out and capitalize on these moments. Epic showdowns, character-defining choices, and unexpected alliances can create cinematic scenes that your players will cherish for years to come.