How to Say Yes Without Turning Your D&D Game Into a Joke

In my last post, I explained how challenging myself to say yes to players made me a better dungeon master, even though I sometimes said no.

Sometime in the 90s, I returned gaming conventions after more than a decade away. Some folks played Dungeons & Dragons differently than I remembered. I played with a DM who said yes to more gifts than Santa Claus. Any time a player wanted to try some lame scheme, the DM would permit it—and grant a big bonus for creative thinking. His game held no challenges. It only existed for his players to show off.

My DM’s habit of saying yes should have created a collaborative story that enchanted me, but instead I felt bored.

Some folks equate saying yes with good storytelling. From this perspective, characters are the foundation of story. Players control the characters. Only bad DMs keep the storytelling to themselves. Saying yes to the players lets them contribute to a shared story.

Say yes to deeds that reveal a character’s unique abilities. In one convention game, a water genasi monk’s fast swim speed let her breeze through this encounter.

Except good storytelling rests on characters who face obstacles. If you make obstacles that just enable characters to demonstrate how great they are, then you create a certain, notoriously dull sort of story. Your story features a Mary Sue who can only impress everyone by being wonderful.

In D&D, players never ask a DM to say yes to something that adds obstacles. Players ask for advantages. Players see a high Performance skill on their character sheet, and then ask to sing a cave-in away because maybe the right note starts a landslide. Saying yes isn’t the route to compelling stories.

But D&D isn’t really a storytelling game. Nobody wants to hear a story about your D&D character. The fun of D&D comes from playing the game. For most of us a big part of that fun comes from a chance to feel wonderful and impressive in our character’s shoes.

I often meet players who want to win D&D when they devise a superior character. The play at the table, for them, just offers a victory lap.

So does my desire for a game that challenges me and my characters make me an oddity?

For most players, credible obstacles help make role-playing games compelling. Call of Cthulhu typically ends in insanity or death, but you still get to thwart a dark god against overwhelming odds. Your characters’ losses make them more heroic than the D&D characters who always come out of scrapes better than before.

Nobody sits at a D&D table for vicarious insanity or death. In D&D, characters improve by gaining experience and magical gear. That steady improvement makes the game addictive. D&D players relish chances to show off.

I suspect most players crave a mix of challenges, chances to show off, and chances to feel powerful by overcoming real challenges.

Case in point: My friend Tom is a by-the-book DM with stronger mastery of the rules than anyone I know. Some have called him a dick DM, and he wears that label with a note of pride. He doesn’t try to win against players, but he won’t say yes to a brazen attempt to use Performance. Tom is an expert at running monsters so they make tough, canny foes. Sometimes Tom kills characters. He killed one of mine. If D&D players favored DMs who simply let characters show off, then Tom would rate as a bad DM. Not Tom. As a DM, he reached an elite, level-4 ranking in the Heralds Guild of DMs. This means Tom served a DM at conventions for table after table of strangers, and earned nearly perfect scores on their feedback forms. In his games, when characters show off, they earned it.

D&D works best when DMs find a balance between credible challenges and letting each player feel like a bad ass.

NFL star Cam Newton dominates pee-wee football

Sometimes finding the right mix just requires the players and DM to focus on their roles: Players work to make their characters awesome, while their DM takes charge of posing challenges. In this role, the DM acts as the characters’ biggest fan. As a fan, I want the characters to triumph against real tests. I want a 6’5” 250 pound NFL quarterback to face elite athletes rather than pee-wee football players. Let the Fantastic Four beat Doctor Doom rather than Paste-Pot Pete.

So as a DM, when the players ask you to say yes to something that ruins a challenge, you can say no without feeling like a bad DM who refuses to share the game with players. They have their part, you have yours.

Sometimes, your role as fan of the characters might call for a yes. I can think of three perfect occasions:

1. Say yes to inventive solutions.

When I started as a DM, I followed Gary Gygax’s model. I pitted my players against the most devious deathtraps I could invent. I would build in ways for the players to surmount the obstacles, but the players’ solutions rarely matched mine. The 6 or more brains across the table always proved more clever than me. Soon I stopped including solutions to the predicaments. The players across the table still escaped every impossible pinch. Their invention surprised me and I relished it.

I don’t recommend pitting players against impossible situations, but I do recommend learning to love an ingenious solution. Some DMs grow so attached to a “correct” solution to a predicament, that they reject their players’ ingenuity.

For more, see Player Skill Without Player Frustration.

2. Say yes to stunts and exploits that go outside the rules.

A few years ago I ran the Confrontation in Candlekeep delve at Gen Con. At the end, a dragon flies from Candlekeep tower to tower, table to table, exchanging attacks. At one stop, a character jumped atop the dragon and rode it table to table. After the event, the player giddily recounted the tale to anyone who would listen. He wasn’t alone. Players loved riding the dragon so much that DMs made it part of the adventure. Designer Teos Abadia remembers, “The result was great fun, a nice mechanic for players ending up at other tables, and some really spectacular falls!”

In Mike Shea’s post, A Collection of Awesome Events, he asks players to recount an awesome D&D moment, and then reaches a surprising conclusion: Players love it when they get to break the game. Riding the dragon steps outside the usual exchange of blows in a D&D battle. The Player’s Handbook offer no rules for it. But for players of Candlekeep, it created unforgettable moments.

When players suggest a bold or clever idea that ends a big encounter or that wrecks a major villain, I feel tempted to reject it. I worked to set the stage and a sudden end feels like a waste of effort. But for players, an ordinary battle can’t match the excitement of that one time when they broke the game.

3. Say yes to deeds that reveal a character’s unique qualities.

At a convention, I ran an adventure where a pack of wolves confronted the characters. One player tried to make friends with the beasts and I asked for an Animal Handling check.

The player showed his character sheet. “My background happens to be Raised by Wolves.”

“Turns out, you know these wolves.”

Obviously, if some unique quality grants an advantage that threatens to regularly upstage the other characters, you can still say yes, once. After that, the wolves the player meets might be rivals.

8 thoughts on “How to Say Yes Without Turning Your D&D Game Into a Joke

  1. alphastream

    Thanks for mentioning Candlekeep! One of the things we try to do with these kinds of events is to create space and opportunities for players to come up with fun ideas. The recent Epic, DDEP05-02 The Ark of the Mountains, really did a great job of this. Will Doyle seemed to load each encounter with fun terrain and situations that encouraged players to experiment and employ unique tactics. I enjoy trying to design those situations, in part because I love to play through them.

    A simple thing for home DMs is to add 1-2 interesting terrain bits in encounters. They can be straightforward: a hay loft with a block/tackle, a stack of books, a bubbling cauldron, an open door with foes approaching from the distance and the bar for the door just sitting there, a catwalk or ledge, etc. You don’t need specific rules for them… just place them in encounters and see what the players do. A general rule of thumb I follow is to lean towards just having the cool thing happen, but if it seems too powerful or would be employed all the time (“I want to climb this thing to jump down on the foe”) give them a no-action skill check to see if they can pull off the maneuver and then grant them advantage or a similar benefit.

  2. alphastream

    Oh, I had to come back and add how much I love the way the amazing Rob Heinsoo runs a game. He absolutely loves it when a player has a clever idea. So much so, that he cackles with glee. A player in a 13th Age game might say, “could my PC use my One Unique Thing to do this…” and Rob’s eyes will go wide and he will smile and say, “Yes! And here is how that could work and what might happen…” and what follows is a blend of a deal with the devil (you agree to this course of action, but if you fail then this might happen) and just pure fun in that it might be actually way stronger than the player originally intended.

    That approach is actually a lot of fun, because it is enabling but also chaotically full of possibility. It grabs the interest of everyone at the table, makes the player look cool (even if they go on to fail, because then they are an agent in the developments), and is just plain interesting. I highly recommend hunting Rob down at conventions and watching him run a game. But, otherwise, just experiment with turning Yes into a bargain. “You can climb the wall to get onto the ogre’s back… in fact, you are pretty sure that if it works, the ogre won’t be able to attack you… but the wall looks crumbly… if you fail, it might come down on top of you and maybe even one of your companions!”

  3. Jay Elmore

    When it comes to one-off games like Adventurers League play, I find that saying “yes” to reasonable requests, especially when it’s early in a game session, makes it easier to say “no” to an unreasonable one later. You’ve established that you’re not just dismissing your player’s ideas out of hand.

  4. rileyvann

    This is absolutely the balance I strive for at the table. I have no interest in killing characters, but I want to challenge them so the players as well as the characters have to work to survive. I know as a player, the best memories I have are from such struggles. I say yes, but you’ll have to work for it.

  5. Chris Wachal

    Although I agree with your general philosophy here, which is that saying yes all the time is a bad idea, I question whether you need to have a “say yes” philosophy at all.

    To discuss your points:

    1. Saying yes to inventive solutions is great…if they are actually inventive and actually would work. You say you decided to stop coming up with solutions on your own and just accept the answers the PCs come up with. To me, this counters your earlier point about challenging players with obstacles. If the challenges are so easy that 6 players ALWAYS find away around them, then the obstacles are too easy and there’s no fun in defeating them because they always win.

    To me, that’s exactly why you come up with a bunch of valid solutions and try to limit the players to those solutions unless the idea they came up with is truly innovative. The answer here isn’t “Say Yes”, it’s “Say yes or no depending on how innovative the solution is. Lean towards no so that when you do say yes, it’ll be special.”

    2. This one concerns me the most. Players love bypassing the rules, of course they do. But just because they love it doesn’t make it the sort of thing that should be encouraged. I have friends who still talk about the time they defeated the Doom computer game by not defeating any enemies because they entered the cheat code to walk through walls and god mode. It was hilarious that monsters couldn’t hurt them and they could just run past all of the challenges. But ask them if they want to do it a second time and most of them would say “No, I’ve done that, it’s boring now.”

    This is how I feel about most attempts to bypass the rules. It makes one player feel awesome about how they managed to break the game and win in a way other than what was intended. But it often makes the other players at the table feel cheated that one player got the break the rules in order to do something awesome and got to be the hero because of it. While one player was looking at their abilities and thinking “I need to be able to do 30 damage this round or the monster is going to kill us, what abilities do I have that might be able to do that?” another player is thinking “How do I outright kill this monster, doing essentially infinite damage by bypassing the rules?”

    Once they’ve bypassed the rules, a couple of things happen: A) That player will attempt to bypass the rules at every chance they can get because it has proven to be more effective than following the rules. B) The other players at the table will either be super happy that their ally came up with a way to cheat the game and win or they will feel like an idiot for having tried to follow the rules because breaking them is more effective. This likely ends up with them attempting to bypass the rules at every available opportunity.

    All this does is encourage all of the players at your table to continually ignore the rulebook and their character sheets and come up with other solutions to every problem. Plus, they get bored at using the same way to break the rules twice. So, they have to continually come up with new and innovative ways to break the rules that they haven’t used before to keep themselves satisfied. This makes it very difficult as a DM to make rulings since the things the players are attempting are so far outside of the rules that there is nothing to base those rulings on any longer. It also makes it difficult to determine the difficulty of an encounter since it’s just as likely that a monster could be a 5 round slog through hitpoints as it is a 1 round cakewalk because someone finds a way to defeat the monster outright.

    Since, as you wrote in your article, the goal is for them to overcome challenges that feel like challenges, this is a bad thing. You want them to feel like the monsters almost beat them.

    It also means that the players are searching for more and more wild ideas to try to bypass the rules. Which is the easiest way to turn your game into a joke. Down that road lies trying to sing a cave-in away. If the players think there is a chance you’ll say yes because you’ve said yes to other things that break the rules, then they’ll try it. Then you’re either faced with saying yes to singing the cave-in away or continually having things suggested and having to say no nearly constantly. Which can really bog down a game.

    3. I have less problem with this one. But it can come off as extremely coincidental. Sure, they were raised by wolves…but that was halfway across the world, why would they know these wolves? Also, if every wolf they run into is an old friend, then this risks turning your game into a joke.

    I think the key thing to note is that all of these techniques are a good idea…from time to time. But they should be rare. The “Say Yes” philosophy says that the game is always more fun when you say yes. But I argue that the game is actually more fun when you say no way more often than you say yes. It encourages them to really think and come up with good ideas instead of the first thing that comes to mind. It makes the times their plans work way more fun because normally their plans fail.

    1. Andy Gibson

      Saying yes is fine, but I’ll point out that the original is “say yes *or roll the dice*”. Rob Heinsoo’s approach, as an example, is the epitome of this. He’s saying yes to a “deal with the devil” roll, not an auto-success. As a guideline, I suggest thinking about increasing or decreasing the swinginess without changing the average too much. If the base attack option has a 2/3 chance to do 6 damage, let an “innovative solution” do a certain 4 points, or have a 1/3 chance of doing 12 damage. You can vary up or down a bit, but as a guideline this will stop you being too much of a “dick GM” or too much of a “giveaway GM”.

    2. alphastream

      A skill that I think is overlooked in DMing is clear communication. If players are misunderstanding why you say Yes or No, tell them. It’s okay to break through the wall and say, “Hey, look, I want your cool ideas to work, but that will always be balanced with not breaking the game. The more you work with me towards fun ideas that are reasonable, the more we can make them happen. I’m on your side. Now, sometimes I might make the wrong call. Maybe I give you something too weak, or maybe I give you something too strong. I’m looking at us to have the mutual respect that we work together in common interest around such situations.”


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