17 Easy Ways to Develop Improv Skills for D&D

Dice photography by the talented Timothy Miller.
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Premise

In addition to my six years of D&D experience, I am also an accomplished improvisational comedian with ten years of experience (as of 2020). I perform regularly for paying audiences. Though I relish making audiences giggle, the improvisational skill set is useful for many things beyond comedic performance. One such application of improv is found within D&D. In fact, improvisation is an integral skill for any hobbyist of tabletop RPGs.

Improvisation’s benefits go beyond mere humor, allowing pure collaboration between players, DMs, and dice. There are countless stories and memes about DMs drastically adapting their plans after players deviate from expectations. Collaboration means the game is unpredictable even before the dice roll.

I intend to impart lessons I’ve learned from improv that have enhanced my ability to enjoy D&D. What I share is based on principle, not absolute laws. Do not allow exceptions to distract you from the principles. Principles should be mastered before embracing calculated exceptions. I know some principles won’t immediately seem improvisational, but I assure you they are. Many of these skills overlap, so I recommend reading the entire article to discover which principles speak to your understanding.

Yes, and…

You’ve probably heard this one before. “Yes and” is a principle of positive reciprocation; you receive a gift and show your gratitude and care for that gift by building upon it with an additional gift. When I say ‘gift’, I’m referring to an idea or established imaginary fact that has been created by someone else. When you roll a “1” on your d20, you avoid anger to instead play with the new reality by describing the failure as if it’s fun to lose.

A famous example of “yes and” occurs in The Lord of the Rings: The Fellowship of the Ring. In this scene, Frodo informs the group that he’ll take the one ring to Mordor, but he doesn’t know the way. The future-fellowship characters yes-and Frodo with their responses. Aragorn declares that Frodo has Aragorn’s sword (his help in the fellowship), followed by Legolas offering his bow and Gimli offering his axe. Frodo might have sounded crazy, but they yes-anded him. It’s an iconic scene.

An even simpler example is this:

• Rogue: I will infiltrate the Beholder’s lair.
• Sorcerer: Yes, and it’s gonna be tough. I’ll cast Invisibility on you.
• Ranger: Yes, and you don’t have darkvision, so I’ll go with you as your wingman.
• Wizard: Yes, and I’ll give us all telepathy with Rary’s Telepathic Bond so we can silently coordinate the infiltration.

When a party member declares intent that initially seems ‘dumb’, it’s your job to make sure the idea succeeds. Treat your allies as geniuses with brilliant ideas. You’ll be surprised by the frequency at which bad ideas can become memorable and fun. 

Yes-anding can also up the ante for your goals. A king tells you to retrieve the head of a hill giant that is plaguing his trade roads. You declare to the king that you’ll additionally learn the hill giant’s name for a victory ballad. Bards will spread the word around the kingdom that the king is safeguarding the city’s roads, economy, and overall safety. It’s a subtle change to merely accepting a quest. It also makes the quest more interesting for your party.

You can yes-and during narration as well. Long rests and other boring moments that are usually glossed over can become noteworthy. Your dungeon master will love having you in the group as you spice up these game mechanics with jovial substance. Describe your long rest with descriptions of snoring, food quality, and degrees of restlessness.

One common question about yes-anding is how to handle a disagreeable situation. When this occurs, pause to ask yourself why you feel that way. If you remain at odds with the situation, you can attempt a ‘no-but’. The no-but works like a martial artist turning an attacker’s momentum on itself, but this involves turning a divisive situation into an agreeable one: “No, I can’t do that, and here’s why. I have an alternative idea that I think we can agree on.” Hopefully, you and the other players know each other well enough to make choices that will not provoke discomfort (sessions zero should help prevent this problem too).

Make Others Look Good

One of the great keys to happiness applies to D&D as well. Everyone else in the game is in a partnership with you. Making other people look and feel brilliant will make you irresistibly likable as a player. Gaming tables are no exception to the rule of selflessness. People who seek their own spotlight will often find themselves less prone to find friends, and their ideas will be less valuable. Players will reciprocate your positive paradigm.

Don’t neglect the DM as a player themself. Interact with elements they’ve taken the time to add to the story. Pay attention to what everyone says and does; they’ll treasure your company because you listen and react positively to their ideas.

Let Go and Play

Let it go; leave it at the door. I’m referring to ego and fear. Let them go, and play unbound. Ego makes you judgmental of the ideas of yourself and others, and fear is intertwined with the preservation of ego.

Those who struggle with fear and ego can practice an exercise: when it’s time to play, go find a rubbish bin in which you can toss your metaphysical ego and fear. This exercise will physically symbolize your commitment to having fun. Think of it as a ritual to get into the desired mindset.

Fear is often based on the fear of rejection. Here is a trick for letting go of fear. Remember people are preoccupied with what people think of them, so they don’t have the mental bandwidth to fret about what they think of you. Most people are living in fear that their ideas will be rejected while admiring people who overcome this fear to actualize their ideas. Be the type of person who realizes people are waiting to look up to heroes that take chances and make mistakes (like Miss Frizzle).

You should also let go of the outside world while you’re playing D&D (unless something urgent is requiring your attention). Texting and browsing the internet for anything that isn’t game-related will pull you out of the game, and you won’t be able to contribute through improvisation. Get your head in the game (like Zach Efron).

Find Common Ground

Memorable roleplaying happens when characters discover their commonalities. Fans of Critical Role, I challenge you to watch for times that the cast finds common ground between their characters to seize a special moment in their collective story. You can do this too. Evil characters can common ground with the righteous.

Try this method when you next find yourself at a loss for things to say to other characters: ask an open-ended question, listen intently, and respond with your character’s thoughts. Don’t literally say ‘we have more in common than I thought”, but your in-character response can be about how your character has had similar thoughts and experiences, even if they’re frivolous. Share details of a romantic crush or a delicious meal you once had. This is an opportune time to invent something new about your past that was not previously established. Doing this allows you to bond with other players and characters while opening you up to long-term character relationships that feel organic and rewarding.

Seek Themes

The best improv scenes focus on themes: greed leading to ruin, hard work being more important than talent, or love conquers all (to name a few). Themes can also be about opposite concepts squaring off, such as justice and chaos, freedom and safety, or love and loss. The DM may tell you what themes they’re trying to seed throughout a campaign, but you’ll typically detect themes independently. Be vigilant for themes built into player characters’ backstories, too. In my experience, players don’t realize they have opportunities to explore themes. You can verbalize an emerging theme to make sure other players don’t miss it, but I’d try an organic approach first.

Practice finding themes by analyzing your favorite stories. Star Wars and Harry Potter use themes about the importance of a parent’s love. The Hobbit and The Lord of the Rings use themes about small people with massively impactful deeds. Octopath Traveler has a theme for each of its eight characters to explore in their storylines. Acquaint yourself with your favorite themes, then employ them to enrich D&D.

Play on Assumptions

Expectations and assumptions are natural to the human brain, aiding in the constant processing of the world around us. We seldom notice when our brain is making these predictions, especially about people. This unspoken assumption becomes an unspoken joke when you defy the expectation. One of the best examples of this concept is from SpongeBob Squarepants when a tough guy gets into the Salty Spitoon after boasting about his breakfast: a bowl of nails… without any milk. The unspoken joke is that we assume a bowl of nails is a tough breakfast, enough to warrant entry to a tough-guys-only tavern. When he’s initially denied entry, it’s surprising; when he adds the detail of no milk, the bouncer appears frightened and grants him entry.

Another example of this is in the movie Elf when the hot-shot children’s book writer that everyone is scared of is actually a dwarf of diminutive height. We expect a tall man in a power suit, but we get a small man with a chip on his shoulder in a power suit. This subverts our subconscious assumption of what a demanding, intimidating writer looks like.

Another way to apply this is to make strange concepts become mundane. Bizarre scenes will be more interesting if they’re grounded in realism. For example, I once played the role of a piece of paper in a subway tunnel in an improv scene. I enjoyed portraying the life of a discarded piece of paper blowing around with every draft of wind, but it became incredibly enjoyable when my scene partners and I grounded it in character reality. The piece of paper was tired of just being blown around to wherever the world wants it to go, a people pleaser. This piece of paper was tired of being written upon, wanting instead to write its own destiny. The subway rats were naysayers who thought the paper should accept its lot in life.

One additional example is anthropomorphic movies like Zootopia that use human character traits in the context of animals. Jokes in that movie are unspoken as we the viewers enjoy seeing which animals would fulfill different careers in the real world. The sloth working at the DMV is a great example of this concept. Humanoid animals are a strange concept compared to real life, so giving them real-life jobs is an easy path to humor.

If you lack the instincts or insightfulness to notice the assumptions and expectations I’m describing, or if you’re not sure you understand, you can also think of this as an attraction of opposites. A famous example of seemingly opposed characters becoming best friends is found with Gimli and Legolas in The Lord of the Rings. Opposites attract in improvised storytelling:

• A barbarian with a checkered past of savagery and war can have a night job as a dancer.
• A wizard overestimates her strength as she constantly challenges people to arm wrestle when she’s frustrated.
• A bard is an inspiring leader of men but fumbles over his words when women are present.

When you catch yourself falling back on an easy assumption or expectation, try twisting it to have some fun.

Prioritize Preparation

It’s infinitely irritating to experience a person telling a comedian to ‘say something funny’ or ‘make me laugh’ on command. Improv thrives with preparation as the framework. This is a concept I discussed in this other article if you’re interested. Comfort with improvisation doesn’t exempt DMs or players from proactive preparation. Think about what’s coming up in the game. Improv scenes typically begin with prompts to get started, building from that starting point. Your D&D improvisation should be backed up by preparation. Without preparing yourself, you risk improvising in a void of mediocre ideas. Here are examples of valuable preparation: backstory development, considering what’s to come, reviewing accents, reflecting on what has happened in past sessions, and even writing out specific dialogue ideas.

Setting goals for yourself is a form of preparation. Goals may include new vocabulary words you want to use or other characters with whom you want to spark up a conversation. This will push you to find opportunities for improvisational growth as you’ve already visualized what you want to achieve.

You can also prepare songs and playlists for your character moments that you anticipate; play the perfect music when your character reveals secrets of their past, and your DM will love you forever. Just make sure you don’t take up time looking up the song. Load the song ahead of time if you think it’ll come up.

There will be times when departure from preparation is prudent. Don’t tie yourself down to your goals and preconceived ideas. You may be playing in a session where it does not seem natural to bring up your prepared ideas. Do not force it! Write down ideas so you can use them in future sessions when the moment feels right.

Groups struggling to roleplay can consider learning and playing warm-up games used by improv troupes. Warm-up games vary in purpose, such as getting a group’s energy up, group bonding, or getting a group’s minds to loosen up with ideas. You can readily find ideas for warm-up games on the internet, but here is a list that I like for the sake of giving you a suggestion. Here is a larger list for which I can’t verify that all the games are useful.

Be 100% Present

Pay attention beyond merely listening or remembering what has happened in the game. Be aware of what is going on below the surface of this social game. Are other players not having fun, needing more moments to shine? Find ways to bring them into the spotlight. This will help your group squeeze fun out of tough D&D sessions. When you succeed at committing your full attention, you can respond meaningfully to such situations.

Taking notes is ever helpful, even if you’re note-taking is poor. Writing down details will help you to recall details later. The palest ink is better than the sharpest memory, and recall is crucial to your game. Try to recall plot points, meaningful dialogue, and even rules. Note-taking also incentivizes you to pay attention while you capture what’s happening. With strong memory, you’ll avoid slowing down the game by asking your DM and other players about details and rules. If your DM gives you a map, study it. The DM won’t have to stop the game to help you and the group work out what to do next because you’ll be keeping your party on track.

Part of being present is listening with intent. You should know when to sit out of a conversation. Other players won’t appreciate your interruption as you interject what your character wants to say. Letting players complete their own character moments. Don’t chitchat on the side while other players are handling a situation. I know it’s not realistic to demand your full attention for hours of game time, but you should attempt to lend your attention and energy throughout your game sessions.

Maybe most importantly, don’t get stuck in your head. It’s commonplace to think about other things in your life that you can’t control and that are irrelevant to the game you’re playing. Stay focused and avoid distraction. Don’t be on your phone if it’s not important. I’m often surprised at how much my boredom or lack of connection to a game is fixable. The fix is committing to paying attention and adding my energy to the game instead of brooding about what I’d rather be doing or how I wish the game was going. Dungeon masters love players that commit to making the game a success instead of judging what the DM has prepared.

Approach Resolutions

Improvisation can result in meandering. To avoid meaningless improvisation, seek micro-resolutions. I say “micro-resolutions” to make it clear that I’m not talking about a grand, singular resolution to a story. You’ll find micro-resolutions in character conversations, character arcs, and more. A resolution presents itself in many forms, including new information, relationship developments, foreshadowing, or discovering common ground between characters.

Roleplaying is only as good as its results. Comically speaking, some of the best resolutions appear as big laughs that come from a particularly clever idea or a satisfying full-circle development to the scene. I’ve seen many roleplaying instances wasted because players don’t seek a resolution; they don’t work toward anything. You don’t have to know the resolution to get started, but you have to know you’re trying to discover one. This is actually a conversational skill for real life. People need to learn when to end a conversation, but they must also learn how. Resolutions are often initiated by a statement summarizing the conversation in the context of takeaways or lessons. Here are several examples:

• “You’ve inspired me. I’ll look to your example next time I feel like quitting.”
• “This event has hurt us both more than I realized. Let’s agree to never let this happen again to anyone.”
• “Ha! We’re both after the same thing then. I owe you a flagon of ale if you beat me to it.”

Don’t Fear Silence

The average person believes it’s their social failing if they experience silence. They’ll frantically spout words in order to cover up the silence. It takes mental fortitude and confidence (as well as patience from people around you) to use silence as a form of communication. A dramatic pause at a proper moment will allow a point to sink in. When you’re not the one talking, you’ll know that you don’t have to jump in at every point of silence. Trust yourself and trust other players to use silence effectively. It’s true that some people pause because they lack silver tongues, so give them a chance to formulate responses. You’ll find that you’re relieving the pressure to speak quickly, freeing them up to contribute meaningful dialogue.

Dungeon masters are common offenders, fearing silence since they feel it’s their responsibility to keep things moving. It’s correct for a DM to step in and help when things stagnate, but they shouldn’t be too hasty. Silence can give weight to what’s happening. Silence is the sound of thinking. Be careful not to misdiagnose silence as an absolute problem that requires intervention. Make silence your ally; acquaint yourself with silence.

Contrasting Energy

Interact with characters that contrast your own energy without making the obvious choice of criticizing your differences in characterization. When I say energy, I mean character traits like fast or slow, peppy or subdued, and graceful or sloppy. Opposites are fun to work with. You’ll be amazed at the fun you can have if you’re yes-anding characters that are not just like you. This concept is applied by evaluating the character you’re playing. Identify what kind of energy the character possesses. Then seek with a purpose to interact with opposite-energy characters.

A word of caution: you will experience a natural pull to interact negatively with your opposites. Do not fall for this trap. Speak in open dialogue to find common ground, and compliment whatever you discover to be praiseworthy. This positive paradigm will prevent you from all talking to one another in condescending, brooding manners that lead nowhere. Again, apply this in your real life as well to become more likable and exude confidence.

Speak Names

Use characters’ names when addressing them. You might think you’ve heard this advice before, but let me explain the difference: use names more often than you normally would. Say names by throwing them into your sentences even when it does not seem natural to do so. There’s an emotional response to using someone’s name, so use names when you want to spice up a conversation.

As a tip for dungeon masters, you can diversify who in the party is speaking by having an NPC address a particular party member. This gives speaking opportunities to players who aren’t usually the first to speak up. Use names instead of addressing the party as an ambiguous group. This will also cut down on instances of an NPC ending their statement only to be met with awkward silence from the party as they wonder who will speak next like a standoff in a western movie (but with speaking instead of guns).

Statements over Questions

It’s easy to get stuck talking in circles by asking too many questions; make statements instead. A statement is strong and decisive, while a question is often weak and uncertain. It’s normal for players to lose sight of what they’re actually working toward, but statements backed by goals will help players to remember what they’re doing and why.

A DM will make a huge difference with this simple trick. Instead of asking the party what they want to do next, a DM can summarize optional suggestions for the players’ next course of action in a strong statement about what’s happening. Don’t overuse this method or they’ll feel railroaded (maybe once or twice in a session). A party’s DM can also address each character by name and summarize what the character might be interested in. Best of all, the DM can premise a question with a strong statement like this: “Tony the Squealer looks at you with an inquisitive look, and says ‘Are you going to tell me where you were last night, Joey?’ before sitting down to wait for your answer.’

Players too can state their intentions before asking questions. I find parties are often hesitant to surrender information, so they end up dancing around questions to prolong social encounters by approximately 5x (just my estimate). Every once in a while, skip the run around by talking with straightforward intent. This will free you up for interesting situations rather than paranoia. Do this and you’ll find your creativity flowing as you have spicier social encounters and more time to play. You’ll actually find this to be a boost to your game’s positive flow. DMs will notice the party liking the NPCs more as well.

Fail Big

There are improvisation exercises designed to convince people to celebrate failure. These failure exercises are some of the hardest to teach because the will to win is deeply ingrained in people. Failure should not be feared. Failure is your friend. Own and embrace failure. Games of dice rolls will always result in failures. Dice need yes-anding as well as people. Failure is integral to improv, and it makes success sweeter. I’d bet a handful of your favorite D&D memories include botched plans and low dice rolls.

I once had my character disabled due to Mass Suggestion. He was ordered to watch the spellcaster intently without taking action. Instead of just getting mad and passing my turn, I described calling forth my familiar so it could enjoy the enthralling display that I was charmed into perceiving. The DM felt bad for disabling my character, but I assured him I still enjoyed the battle. Improvising what my character would do during his inaction transformed misfortune into fun.

Additionally, don’t hastily shoot down the ideas of your comrades. You can yes-and with ease if you’re willing to fail. Yea, I know, some of you will be thinking of stupid ideas that have gone awry. The point is to shift your paradigm and aim for positive interactions with fellow players. Your goal is not to ‘win’ this game of D&D.

Start in the Action

This one is for dungeon masters. Many D&D sessions begin with shaky recaps from the previous session followed by the meandering question of what the party wants to do next. Instead, apply this improv principle: skip beyond the dead time. Cut straight to what happens next. Ask the party to discuss what will happen in a session ahead of time so you can anticipate where to start. Episodic television shows are often written this way. Beginning amidst the next task will cut out the fluff that costs D&D players dozens of accumulated hours over the years.

To make sure you understand what I mean, here’s an example of an average D&D session (I’ll indicate where you can consider starting the session):

• Players arrive and chat (6:05 PM)
• “Who wants to recap the last session?” (6:12 PM)
• “What do you want to do now?” (6:15 PM)
• Discussion about what to do, accompanied by clarifying questions as players remember what’s going on. (6:20 PM)
• Decide what to do next. (6:22 PM)
• Do something. (6:23 PM) This is where we want the session to begin, saving you nearly 20 precious minutes of session time.
• Keep doing things and having fun. 
• End session. (9:00 PM)

Be Specific

This is a slight change to the way you present information. Instead of your character telling others about how they enjoy cheese, be more specific; they love goat cheese from the southern dairy farms because that’s where they were raised. Be a meaningful ‘specific’ instead of a wandering ‘generality’. Visualize your character as an empty bag; it can’t stand upright until it’s filled, so you must fill it with personality and story elements. Ideas of specificity create a framework for you to explore while enriching the ideas that follow. Your next idea is enriched as you ask ‘why’ to the previous ideas you’ve established. Going back to the goat cheese example, you could next establish that you love goat cheese because it helped you sleep at night, or because you enjoyed creating it with your mother. “Why do I love goat cheese? Because it reminds me of my childhood with my mother.”

I find that backstories are often developed during in-game improvisation more than in the prepared, written backstory. Let go of inhibitions about what the DM will be ok with. Take your creative license and run with it during a session. Your DM will stop you if you overstep, so push your limits! Don’t overreach with your creative license and the DM will love you. When an NPC asks where you’re from, make up a city name and spout a few specific ideas about it. The DM will appreciate the idea and probably make it canonical, (maybe with slight vetoes or retcons to make it fit the setting). Be specific with the details. Here’s an example of a backstory I made up a moment ago with the intent to add specifics (details in bold):

“I come from a farming town called Plopperton. It’s known for its vast groves of cotton trees, enabling the main trade but discouraging tourism due to allergens in the air. The Snail River runs through Plopperton and has never flooded. People there fear the local feudal lord, Ross Stanton, because of what he did to New Bopperville, a neighboring town. New Bopperton was sacked after its theater troupe created a play criticizing the governor’s infidelities. The play was called Nights and Knights. Stanton claimed the town was planning a coup. Now the people of Plopperton stockpile rusty scythes and sickles as weapons in the old church of Waukeen just in case Governor Stanton ever turns his paranoid violence on them.”

Sound interesting? Read the statement again but remove the finer details in bold text. Notice how this basic backstory would be dulled if I left out specifics like names, types of weapons, political titles, gods, etc? You can try this exercise for yourself. Write a paragraph about one of your characters, then read it again to add specifics. Practice making statements, and then make the same statement again with greater detail. This repetition and revision is excellent practice for improvisation.

Describe Movement and Posture

While your character is speaking, you have an opportunity to describe how your character is moving. Is your character eating a sandwich while questioning people at a tavern? Is your rogue juggling a dagger or two while they threaten a corrupt merchant? Describe it and have fun with the movement. Disappointment can be portrayed when your strong Fighter is lacking his usual upright posture. Fear can be described in several ways (I wrote about fear roleplaying in this other article). If you’re comfortable with it, you can demonstrate your character’s movement physically to your other players. Stand up and show them what your character is doing. An added bonus to doing this is that someone standing up to visually demonstrate their narration will provide a change in sensory stimuli, causing other players to perk up if they’re bored or distracted.

Conclusion

Like I said before, this advice is about principles. Mastering these fundamental principles will make you a full-blown improviser at your D&D table. You’ll know when to make exceptions once you’ve mastered the fundamentals. While these principles are basic, I promise they’ll help you to become a better collaborative storyteller, RPG player, and genuine friend. Apply these principles at your gaming table and I promise you’ll become a popular person to game with.

Let me know how it goes! I’m happy to provide insights to anyone who leaves a comment or sends us a direct message, so feel free to do so. May your improv be mighty, gamers!