When we think about the skills Dungeon Masters require to run great D&D games, many come to mind. We might think we need to have mastery of the rules or a keen mind for combat tactics. We might assume we need to build out a world from scratch including its history, religion, and politics. The reality of the game is much different. We don’t need those skills to run great games. One skill, however, stands out when it comes to running awesome D&D games.
Games never go according to plan. The players latch on to ideas we never thought of ourselves. They make decisions we never considered. They head east into the great unknown when we have reams of maps for the well-charted west. They fall in love with NPCs we made up on the spot and kick the most important quest-giving NPC over a cliff thinking they were a doppelganger. Reacting to these on-the-spot changes and still managing to keep the game running smoothly is the difference between mediocre DMs and great ones.
We might be tempted to push the game back on track and force events to go the way we expected they would go. Doing so, however, can be a mistake. Pushing the game in one direction removes the agency of the players to guide the story. Second, it’s fun when things don’t go where we expected. It feels magical when the story expands beyond the minds of any individual at the table. It’s up to us to weave that magic and the spell we’ll use is improvisation.
When we talk about improvisation, we're not talking about using funny voices or falling into character. Those are certainly fun skills to develop but they aren’t the core of what we’re talking about here. We’re talking about the skills required to keep the story going and making sure it’s fun regardless of the choices the characters make or the unexpected events that unfold. We don't force the characters to go one way or another, we adapt based on the choices they make.
Improvisation is a skill that gets better over a lifetime. Whether we’re just starting out or have run D&D for forty years, we can always improve this skill. We pick up tricks. We learn new techniques. We figure out new ways to riff with our players and come up with wild ideas we never would have thought of before it happened at the game. We get better at improvisation the more we do it because the more we do it, the more confident we become. Practice builds confidence which is the foundation of good improvisation.
Delegating Rules Mastery
As you get started running D&D games, you might find yourself overwhelmed by the sheer rules of the game. D&D is a complicated game to run. Instead of taking on the role as the full arbiter of the rules, ask the players to help. Did you forget how much damage thunderwave does? Ask someone to look it up for you rather than do it yourself. The more we rely on the players to help us answer rules questions, the less likely they’ll think of us DMs as their opponents and understand that the DM, like the rest of the players, is there to watch the story unfold.
This doesn’t get you off the hook from understanding the basics of how D&D runs, though. You don’t have to master the rules but you should be proficient enough for the game to run smoothly. Give yourself enough time to read through and understand how the game works before you begin to run it for your group.
Learn to Let Go
Much of the struggle to get better at improvisation revolves around letting go of our expectations. When we sit down to plan and prepare our game, we build in our mind how we expect things to go. Then, when we’re at the table, things don’t always go the way we planned. If we hang on too tight to these expectations, we lose the opportunity to be surprised by the direction the story goes. We’re not building a video game, filming a movie, or writing a story here. We’re experiencing the story as it unfolds.
Commonly this will happen when we expect a fight to break out but the characters instead figure out how to get around it through a discussion with the potential combatants or by subverting the confrontation some other way. Say the characters run into a small hobgoblin camp. We assume they’ll go in and fight some hobgoblins but what if, instead, they end up pretending to be mercenaries hired to join the band? What if they end up sneaking right past the camp with a series of great Stealth checks? What if they lure the guards of the camp away with a huge bonfire some distance away? We might not have expected any of these things but all of them could lead to an interesting story. We’d miss out on that if we simply force the confrontation and make the fight happen the way we expected it to in the first place.
Building interesting situations for our characters to explore and letting go of our expectations about how they will approach it is a huge step forward towards improvisational DMing.
Ask Questions and Listen to the Answers
Those who study improvisation say a great deal of the art of improvisation comes from listening. We can’t improvise if we’re not listening to what the players say and how it can change the game. One of the easiest tricks to steer the game is to ask players guided questions and use their answers to move the game forward.
Here are some examples:
“Mao, what object do you find irresistible in this curio shop?"
“Warryn, what interesting event unfolds as you travel through the jungles of Chult?”
“Tysabri, what are the three things you notice first about the city docks?”
“Diva, what drives you to protect your dwarf companion from the undead knight?”
You’ll notice that all of these questions help steer the characters but in a way that lets us learn something more. They’re not too general or open-ended. We know Mao the rogue is going to want something in this shop, but we don’t know what. We know that Diva is going to aid her friend, but we might not know what drives her to do so. This might seem like we’re steering the story too heavily but sometimes it’s up to us to guide the story down a fun path instead of asking too vague a question such as “what do you do?” without context.
Asking questions also gets us involved in the characters in the game. It helps us hear what the players are hoping for as the game unfolds. Asking questions and listening to answers helps us break out of the story we have in our head and gets us to recognize, realize, and embrace the stories of the characters as they travel through the world.
One of the most common topics of improvisation surrounds the idea of “yes, and...” This improvisational technique has two people build a story by passing ideas back and forth, continually accepting and adding on the ideas of the previous by saying “yes, and...” This can work well in D&D though sometimes “no, but” is more appropriate when a character wants to try something impossible but we DMs can offer an alternative. Many times this might start with a player’s question:
“Can I break through the prison bars?”
“No, but you notice that the guard holding the keys has fallen asleep and the keyring on his belt may be just within reach.”
This is the back-and-forth storytelling that lies at the core of D&D. DM’s describe the situations, players describe what they want to do, and the DM describes how they might do it. Using “yes, and” and “no, but” builds in a negotiation into the game. What are the characters willing to risk to accomplish their goals?
Read the Books
Loading our brain up with great fiction improves our ability to improvise. Books, movies, TV shows, video games; all of these serve as great sources of inspiration for our D&D games. The D&D books themselves, however, offer a tremendous value for improvisational gaming. The Monster Manual is packed with wonderful stories, hooks, and ideas you can drop right into your game at the right moment. If you read no other D&D book from cover to cover, read this one. The Dungeon Master’s Guide too is full of inspirational ideas. In particular, the random tables in the DMG serve as a wonderful inspirational aid while preparing our games. Random tables can break us out of stereotypical ideas and give us fresh ideas for our game. If you’re running a published adventure, read it through so you can drop in foreshadowing and feel comfortable if the characters take a different direction from what the adventure expects.
The Mechanics of Improvisation
When we run our D&D games, some key mechanics can help us improvise situations and offer potential actions to the characters: skill checks, advantage, disadvantage, and inspiration. These mechanics work together to help facilitate improvised situations. They also fit into the ideas of asking questions and offering options.
If you aren’t familiar with these mechanics, take a few minutes to read about them either in the D&D Players Handbook or on D&D Beyond before continuing.
When we run our games, we describe the situations in which the characters attempt to overcome obstacles to accomplish goals. Sometimes, if the actions the characters try are particularly easy, the characters can just do them. If they’re challenging, however, we can set a Difficulty Class (DC) to the challenge based on how difficult it is. Easy yet fallible actions are about a 10 and really hard challenges are about a 20. We DMs pick this Difficulty Class, between 10 and 20, depending on the difficulty of the situation and the action the characters want to take. Stealing keys off of the belt of a sleeping guard is probably a 13. Bending the iron bars of the cell is probably a 20.
In some situations, particularly in combat, we can make offers to the players. If they succeed at a particular skill check, they can gain advantage on an attack. For example, if a character is willing to leap up on the stone table and dive in on the ogre, they can get advantage on their first attack if they make a DC 13 Acrobatics of Athletics check. If they fail, they’ll slide on the table and land at the ogre’s feet prone.
These sorts of deals can work either way: DM to player or player to DM. If a player wants to try something awesome, we can give them a DC to achieve it and grant them advantage if they succeed. Likewise, in order to add some excitement to a situation, we might let the player know of a potential option they can take, the difficulty to do so, the advantage they’ll receive if they succeed, and the disadvantage they’ll receive if they fail.
Finally, if we find that a player is acting in character and moving the story forward, we can reward them with inspiration. Inspiration is a tricky mechanic to remember and work in but it can serve very well to reward players for making choices true to their character that also keep the story moving forward. I personally like to award inspiration when characters take risks or will offer it as a reward if they are willing to do so.
Continuing our Lifelong Quest
This article barely scratched the surface of what it takes to be a great improvisational DM. It takes practice and work to get good at it. When it works, our games truly become something magical—a story none of us had individually considered but instead built together. In future articles we’ll talk about some of the tools that help us run our D&D games including tools that help us improvise right at the table.
About the Author
Mike Shea is a writer, technologist, dungeon master, and author for the website Sly Flourish. Mike has freelanced for Wizards of the Coast, Kobold Press, Pelgrane Press, and Sasquach Games and is the author of the Lazy Dungeon Master, Sly Flourish’s Fantastic Locations, and Sly Flourish’s Fantastic Adventures. Mike lives in Northern Virginia with his wife Michelle and their dire-warg Jebu.