How to Write a DND Heist One Shot

Welcome back to How to Be a Better DM, I’m your mastermind for today, Justin Lewis, and you’re here with me to learn how to tell better stories for yourself and your friends as you DM sessions of Dungeons and Dragons 5e. aHow to Be a Better DM is presented to you by Session 0 Studios, D&D podcasts and shows to sate your ever deepening hunger.

I’m excited for today’s show because it’s actually something that I’ve been working to improve personally. I’ll explain a little later in today’s show, but I’m really excited to get into today’s show. Before we do, I don’t know who needs to hear this, it’s probably you, the DM listener that I’m currently pointing at, but you need to hear this.

You’re doing wonderfully. You may think you aren’t a great DM or you may have had a session recently that was less than encouraging, but know that you are doing well. First of all, most players could never do as well as you are as a DM. Second, being a DM is hard and it is a skill that requires practice. You’re doing splendidly so don’t give up.

Now, I hope that wasn’t too sappy for you because today we are going to talk about doing a DND Heist One Shot!

Why Do One Shots at All

Before we talk about heists, I want to take a moment and talk about why you would even consider doing a one shot. Back on episode 82, https://session0studios/captivate-podcast/reserve-1/, we talked about 10 reasons why you should one shots. Let me just summarize one of the points and also explain why this particular topic appeals to me. You see, with one shots you can try new mechanics, and new scenarios that might be intimidating to pull off in your actual campaign. Doing one shots challenges you.

Why Do a Heist One Shot

Now the next question is why you should do a heist one shot?

Well the first answer is that, it’s fun. Think about all of the heist movies you’ve seen. There’s the Italian Job. Oceans 11, 12, 13 and so on, Army of Theives (which if you’ve seen, then in our upcoming live play Show, Calignos, the character played by Tanner Weyland, my cohost on this podcast, resembles the main character of Army of Thieves so much it’s delightful).

The list of fun movies is endless.

The second reason is that I think a heist, more than other types of one shots, is somewhat more technically challenging. Let me explain. In order to make any particular one shot as good as it can be, there requires a certain level of believability. You must also strike a balance of difficulty. If the crown jewel of Tethrezrembot is only moderately difficult to steal, then your party will likely think the one shot was more a joke than an actual challenge.

To that end, the thing that the party is trying to heist has a perceived value proportional to the difficulty of stealing that object. That means if the party is to believe the value of the target, then the defenses need to be difficult and believable. Also the party will want a sense of accomplishment.

Original Characters or New Characters?

So the first question you need to ask when doing any one shot is whether or not it will be canon in your campaign or not, and whether or not your players will create new characters. These are generally two separate questions.

For example, in my current campaign, I am planning an extra special one shot for my players. This is a spoiler so if any of my players are listening please stop listening. In my campaign the BBEG is named Dreamtaker, and he was a very powerful Fey Creature who was split into pieces in order to be stopped previously. The pieces of Dreamtaker are all items. 

In my current campaign the party has fought against Dreamtaker a little here and there, and one of the characters has actually been possessed by Dreamtaker essentially and works for him.

I am planning a heist one-shot, where, somewhere else in the universe, another group of mercenaries has been hired to steal an artifact. Unbeknownst to those new characters, that artifact is a piece of Dreamtaker. This one-shot will still be cannon, but it will take place far away from the main plot line and with totally different characters. I’m going to use this one-shot to explain why Dreamtaker has assembled another piece of himself without simply saying so to my players.

When you do your heist one-shots, or your one-shots in general, ask yourself whether it will just be a non-canon, fun experience, or if it will be salient to the main plot. 

The advantage of making it non-canon is that anything that happens doesn’t have to really make sense in the grand scheme of things. You can be more loose and have fun with how you do certain things. On the flip side, one of the advantages of making your one-shots canon is that your players will take things a little more seriously.

Once you’ve made your choice you can move onto the next consideration, whether or not to make your one-shot an Ensemble one-shot.

Ensemble

An Ensemble is, simply put, a group where everyone has a unique and specific role. This plays very well with the heist because generally, in a heist you want as few people as possible, but you still want every job taken care of, and you often need the best at doing any particular job. Think about all your favorite Heist type movies or shows. One of the best examples that I can think of is called Leverage. It’s a show about a group of people who used to be thieves who decided to use their talents to help people in need. It’s a fun show and it shows off the Idea of the ensemble beautifully. There are 5 characters in the group and each character has a specific job. There is the mastermind, the grifter, the acrobat, the techie and the muscle. 

So why do I bring this up?

In your Heist, you’ll need to consider how the ensemble will be created. Even if you don’t help create it actively, it will be created. For example, let’s say you decide to have your party keep their same characters. Each member of the party will find a part to play. Most often this will mean that the party will sort of split up responsibilities during the planning phase of the heist. This is a good thing because it should actually help you in your planning phase. What I mean by that is that you’ll likely match the challenges of the heist to your party. You’ll create opportunities for each member to feel like they are the only person that can handle that particular obstacle. Conversely, you’ll likely put in some roadblocks that seem party specific that they’ll have to think their way out of.

If you decide to have your party make new characters, it might be fun in the outset to have them pick roles within the ensemble that you want them to fulfill. That way they would make their character specific to the role.

Some examples of role that could be fulfilled are:

Mastermind

Grifter

Con-man

Techie

The Muscle

The Impersonator

The Getaway Driver (Depending on your world)

The Acrobat

The Sneak

The Safecracker

The Demolitions Expert

The Distraction

The Forger

The Artificer (For building things like replicas or special contraptions)

The Face

And those are just to name a few. If you want more ideas, just watch any good ensemble show and you’ll get a good idea.

The Target

Now that we’ve talked about the party and the roles they’ll be playing in our one-shot, we need to talk about the prize, the target, the booty. As any good thief knows, it doesn’t matter what you get, only what you keep. Similarly, why would you want to keep something that doesn’t have much value?

In order for any heist to make any sense, the target must be valuable. Since you are devoting a one-shot to the heist, I would say that the target has to be pretty valuable. If you want to turn the one-shot into like a mini-campaign, the target would be even more valuable.

Often, you’ll likely make your own target but you can also choose artifacts from any of the sourcebooks that have already been published.

As a general rule of thumb, it’s generally best not to make the object of the heist a world-ending relic, unless that happens to be part of your overall plot if the one-shot is going to be campaign cannon. I say when in doubt, just make it a priceless object of monetary value, that way the only motivations are greed rather than world domination.

When making the target, you also want to make it have a nice backstory itself. In a way, the object of the heist is also a character and it needs fleshing out. Think about the Pink Panther movies (more so old ones) where the Pink Panther diamond almost seemed to have its own mind and will. The Pink Panther itself was a character in that series. That’s why the opening credits always started with some smooth jazz and cartoons depicting the Pink Panther evading and generally getting the better of Jaque Clouseau.

So maybe in your one-shot you want to make your target have a life of its own. You could even go so far as to even make the target sentient, whether it’s an object or a person. Adding this sort of complication adds another layer into the story and can make for a more dynamic experience for your players.

The Owner of the Target

Now, the next big consideration is the person who owns or is in charge of the object of the heist. If the target is a person, (a kidnapping) then the owner of the target would be someone in charge of their safety or someone really close to them.

Thinking about the owner of the target is important because all of the planning that happens hereafter will take into account who the Owner is and what resources they have at their disposal. It also incorporates the willingness of the Owner to kill to protect whatever the target is. Really flesh out the owner because when you come to the planning phase, and really everything after this phase, you’ll be in a much better situation.

So let’s go through a quick example so far. If you are in my current D&D campaign and you are listening, stop listening for a second because I’m going to reveal some spoilers.

Great.

So, I am currently planning a heist one-shot. As I’ve mentioned, my players will be creating new characters, but the one-shot will actually be canon within the universe of my campaign.

First, some things you need to know about my setting. I’ve sort of stolen some ideas from Aerois, the High Rollers’ 2nd campaign. Specifically, instead of the Astral Sea being a sea, for my campaign it is all of space, and other planets are considered planes. Some planes do also exist as well though. So because of this there are magical Astral Space ships and such. So theirs sort of an element of higher technology within the universe. That’s important.

The party will be creating characters who are essentially a group of thieves for hire. They will be hired to acquire an object that, unbeknownst to them is actually a piece of the BBEG. That part will be a small reveal to my players at the end. The person who possesses the target is actually a Celestial named Hezriel. I’ve yet to determine exactly what Hezriel is, but he has been keeping vigilant against the BBEG to prevent the BBEG from rising to power again. Hezriel will reside on a planet that is maybe a little more advanced that we are in our reality. The heist will take place in Hezriel’s skyscraper.

So with that example, already, we have a lot to go off of. Because Hezriel is a celestial, and he has some fortune and power, we can plan some things in the next phase that will make a lot of sense. We also know the motivations that Hezriel has for keeping the Target Object and the motivations that the party will have to acquire it.

This is the importance of fleshing out the Target and the Owner of the Target.

The Adversarial Forces

Somewhat tangential to the Owner of the Target, you’ll want to flesh out both the forces that the Owner has at their disposal, and also any other rival groups who might be competing to acquire the Target Object. In every Indiana Jones movie, there are the rival groups, and while it isn’t a heist in the traditional sense, Indie is always on the hunt for knowledge. National Treasure is another great example of a heist with a rival group.

Especially in a one-shot, adding in another rival group can keep the plot and the action going. People act differently when they realize that everything they are doing is technically a race with another group or another person.

That said, adding in another group does add another layer that you must create and if this is one of your first one-shots, you can easily choose to forgo the competitor group and that’s ok.

Going back to my previous example with my weekly campaign, I don’t plan on having an adversarial group compete with my party to steal the Target object. I feel like that would detract from them being able to fully enjoy the experience of new characters and a new situation.

Now that we’ve down all the ground work, let’s hop into the actual planning phase of the one-shot!

Your Planning Phase

For many people, planning something like this can be quite daunting. In fact, for me, planning something like this is daunting, because compared to other one-shots, this requires technical DM skills. But guess what, you’re listening to How to Be a Better DM, where you are going to learn how to do all of the technical stuff. So thank you. Thanks for putting your trust in us and letting us have the chance to make or break it. We never forget you, whether you’re at the gym right now, washing dishes, driving to work or out walking your dogs. We appreciate you and wish we could sit in on all of the games you DM.

Location Location Location

In the meantime, let’s dig into planning the actual nuts and bolts of the one-shot. The first thing you need to figure out is the Location of the target object. This means where in the Universe, in the realms or on the world is your target object located. This is very important because stealing the ancient artifact of a hidden Gumuchi Tribe is very different from stealing a Piece of Dreamtaker from Hezriel Tower within the technologically advanced Pomalen City. 

So think about where your object would be. Extrapolate, logically from who owns it, what it is and why people would want it, to figure out the best location for your one-shot.

From there you can hone in to specifically the building the object is in. For heists, the building always matters. In heists, you need to sneak in and sneak out or getaway fast. That means that you need to know where all the exits are and where everything important is relative to everything else.

I would say, in order of operations do this:

  1. Pick the object
  2. Pick the owner
  3. Pick the location of the building the object is stored in
  4. Create a layout of that building


Once you have a map, it will be much easier to let your players plan through the heist. 

With the map, there are somethings you might want to consider noting on a personal copy of the map. For example, in a large skyscraper like I am working on, I’m going to want to note air ducts and how they connect, but also secret passages that wouldn’t necessarily be on public government records. I can choose if and how the party could uncover those depending on how they plan and the actions they take. You can obviously forgo this step if you feel that the building the target object would be in wouldn’t have anything like that.

Technology Level

Obviously, you’ll need to plan the level of technology that your party will be dealing with. You’ve probably already made this decision when you chose the location of the target object, but let’s talk about a couple of considerations.

  1. Low Tech:


  • If the party is doing a heist in a low-tech area, they will likely have access to magic, this is D&D afterall. You need to decide if the owner of the target object also has access to magic. It would be pretty strange if your party could use spells like invisibility but the person protecting a very important object didn’t have access to spells like See Invisibility. I would at the least make both of them to be on the same footing, though it makes more sense for the Owner of the Target Object to have more resources available.


  1. High Tech:


  • If the party is facing off against a high-tech opponent, then you as the DM will need to worry about things like alarm systems, CCTV security cameras, elevators and stuff like that. You’ll also need to make it so simple things like disguise self or minor illusion can’t just easily disrupt the whole system. If magic is a thing then the high-tech needs to be able to see through it.


I personally think it would be very interesting to have a high-tech party go up against a low-tech Target Object owner and discover that it’s very difficult somehow. Having chosen a tech level, it should be pretty easy now to start to visualize some of the traps and things that you would naturally use.

The Vault

The next thing you need to decide on is the vault. Since before this step, you’ve already made the layout of the building that the heist will take place in, knowing what the vault looks like will be easy.

Also, for context, when I say vault, I actually just mean the final spot that the party must pass through in order to get the object. The Vault could just be a room, it could even be a person if the target is constantly on someone’s person.

The idea here is that this is theoretically the final stage before Target Acquisition and Escape. We are gonna work backwards a little and think about the things starting from the end.

So, combine what you know about the layout of the building with what you know about the resources of the Owner of the Target. That combination of knowledge should help you be able to think about things like “what sort of protections could this owner afford?”

Going back to my example, let’s flesh out the Vault. So we know that the building and the world that the heist is going to take place on is somewhat high-level tech. I’ve decided that the vault will be 3 or 4 levels underground in this massive skyscraper. 

Now, as far as the owner of the object is concerned, Hezriel, the celestial, is quite powerful and has quite a few resources at his disposal. He could theoretically have any sort of protection device that I could think of. This means that I don’t need to limit what I can think of in terms of laser alarms, security cameras, and things like that.

Hezriel is lawful good though, so really anything he employed would be forthright and not sneaky. He wouldn’t have a legion of invisible imps hanging around for example. Instead he would just have strong technology and then a legion of guards on call that could be called upon at a moment’s notice.

So with all of those considerations, I’ve decided to make the vault a suspended room on underground level 3 or 4. The basic idea is that if something trips a major alarm, then the suspended vault is released and falls along rails to underground level 10 where more guards are waiting.

Inside the vault is just a very large room with shelves and stands for different artifacts. None of the other artifacts matter that much. In this case, I don’t mind if the party steals a little something extra because it’s not going to affect the rest of my campaign.

Guards

Now might be...

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