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...

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:

Pick the object

Pick the owner

Pick the location of the building the object is stored in

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.

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.

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 a great time to think through the Guards a little bit. I know we’ve spent time thinking about the owner of the object, and that should help some, but we can spend some time to flesh out the guards a little more.

For example, are the guards actually loyal to the Owner? Are they just hired muscle? Would any one guard consider taking a bribe? Could one of the party members infiltrate the Guards and pretend to be one.

It can change things dramatically if a party member can be a guard. That party member would likely need to look for clues of how the guards act and treat each other and try to mimic those. Maybe the guards belong to a race of people that have special codes about guarding things. If the party wanted to infiltrate the guards, then they would need to know the rules and requirements dictated by the code of the guards in that instance.

In this step of the planning process, you’ll also need to identify the guard spots, how often they change out and where they patrol. I know it’s a lot. If you don’t feel like a criminal mastermind yourself, just wait. You really are the brains behind it all, but I digress.

Make a copy of your map or blueprint of the layout and draw the posts of the guards and where they come and where they go. You can even go so far as to make a schedule.

Some of you out there might be wanting to skip some steps in favor of just winging it when the one-shot comes. That’s fine. Different strokes. In my opinion, with a heist one-shot, you want to make sure you’re buttoned up really nicely, again because the party is going to use everything they have, and that will likely make it pretty difficult to make it feel real without some planning beforehand.

So going back to my example for my campaign:

Hezriel is a celestial, which means he would likely be able to tell if someone is lying, so he wouldn’t hire a group of lawless mercenaries. Also, since he only has this artifact to prevent the BBEG from rising to power, he would employ guards who believe in the same cause.

So it can be reasonably assumed that the guards of Hezriel’s tower aren’t bribable and won’t be corrupted by normal means.

Now, if the party wanted to try and blackmail one of the guards, that might be possible, but I’ll leave the party to think up that plan of attack. If they do, I’ll improvise the backstory of the guard and away we’ll go.

Since Hezriel is in constant vigil against the forces of Dreamtaker, the BBEG, then it’s very likely he would keep his guards in tip-top fighting shape. Therefore, the guards would have fairly advanced weaponry and would prove to be a threat to the party in an all-out fight.

The heist then should likely resemble games like MIrror’s Edge where you can fight some of the adversaries, but if you stay and fight for too long, you’ll just be overrun from their firepower.

The guards also won’t be just pushovers or imbeciles. They’ll be smart and resourceful. Because the guards are that good, and also that trustworthy, it is safe to assume then that Hezriel would have such high standards, that he wouldn’t be able to fill the ranks as fully as he would like. To me this means that he’ll have less guards than I’d originally planned overall.

Because Hezriel is a celestial, it’s very likely he would supply the guards with celestial type weapons. So we can reasonably imagine them with light rifles, light swords (swords made of light), flashbang grenades, and at least a couple of magic users with healing spells and cleric type spells.

I’ve been just sort of thinking out loud here but you get the idea. Now, we’ve really fleshed out the ideas behind the guards and when it comes time to actually make the homebrew guards, I’m ready.

The Actions of the Owner

We’ve got the location, we’ve got the guards, now let’s talk about the owner.

In any good heist movie or show, the owner gets a little suspicious about what the party is up to. Maybe he doesn’t know exactly that its your party that’s doing something, but the owner will certainly think something is going on and therefore do something. That might mean that the owner will simply cycle the security cameras to see if anything was going on, or maybe the owner will get extremely paranoid, and take the target object to a backup location, foiling all of the plans of the party.

Thinking in these terms is a great way to make the entire scenario a little more dynamic, even if it’s just the rote situation that you create. To your players it will seem like the Owner is actively making a decision, which will help them feel like the owner is a real character.

This is also where you might consider adding in a mechanic like a General alert level or something like that. Many video games have something like this, but the idea is that with particular checks at particular points in the game, if the PC fails the check, then the general alert level goes up. The higher the alert level, the more guards there are and the more skittish the guards and the owner of the target object become.

With the owner, you could decide that at a certain alert level, they will do one of a few pre-written actions that will make the game harder for the PCs.

Remember, you want to provide for the possibility for your party to fail and succeed. Make them feel like there are real consequences to their actions.

Another thing you might just decide to do is have the owner take an action, or one of a few actions at a certain point in the game regardless of what the party does. This will also make the Owner of the Target Object feel real because they are making their own decisions like a real person would. Maybe you might set a timer in real life and once that timer goes off, the Owner does something. Or you could say after a certain amount of time once the characters are in the vault. Some common actions might include going to check on the object, or just closing down the building and sending all the non-guard personnel home for the day.

In my example with Hezriel, I’m somewhat torn between the Alert Level type mechanic and just having Hezriel do something just by himself. On one hand the alert level is fun, but on the other hand, I’m never good at remember homebrew mechanics like that. I just forget they are there.

So I think what I might do is actually have Hezriel already have scheduled an inspection from a security expert of the entire system. So basically, at a certain point, the security expert will arrive and then he or she will walk around the entire building with Hezriel (and obviously a grapple of guards) which may make things more difficult for the party.

The Complication

That brings me into another great topic for heists: the complication. Rule #1: No plan survives contact with the enemy. Rule #2: The enemy gets a vote. Two variations on the same theme. What they mean is that you can spend all day planning until you are blue in the face. You could create the perfect foolproof plan, but then the second you start putting it into action, the free agency of other beings will muck it all up.

In heist shows and movies, the Complication is sometimes the best part. It’s the twist. It adds tension to the plot and that tension draws us in, it envelopes us.

So, I would say that you can create complications a number of ways. I think the two simplest ways are choosing 1 complication no matter what, or creating a small random table and rolling on that during the one-shot.

Let me also note that sometimes the actions of the Owner are the complication if you haven’t already figured that out

So going back to my example with Hezriel’s Skyscraper, one of the complications might be that the whole security system is down, so instead of having cameras and lasers, Hezriel has decided to post guards at all of the places that would required cameras or lasers. This means that all of the planning the party did to circumvent digital security measures are useless.

That should give you an idea of some of the things that are possible with a complication.

The cool thing about that fact that magic exists in these one-shots is that the complication could be something else entirely. Like maybe your party member has a werewolf in it, and randomly, there’s a full moon and now you party has to deal with a party member being a werewolf and unpredictable. You can really let you imagination go wild with these complications.

Optional: The Getaway Chase

I know that I’ve been talking a lot and that today’s episode is gonna be a really long one. Hopefully you’re still hooked and I’m not boring you. Hopefully …

In any case, I’m almost done so stick with me.

The last thing that you may or may not want to plan is stuff in case there is a getaway chase. Now, this portion is optional depending on how much time you have with your players for the one-shot. If one of the players is the getaway driver, then it’s much less optional and you should definitely plan for this. If that is the case, then make sure they have other skills that are worthwhile and that they aren’t just waiting the entire session until it gets to their part.

So the first thing to plan is the layout of their escape. Basically, know where the driver is going to go. You don’t necessarily need to know the exact layout, but if you wanted to you could get that granular.

Keep in mind also the terrain. A chase scene through a city is much different than through abandoned catacombs.

You can also spend some time working on the vehicle of escape. If the vehicle is just the party running, then you’re done. Otherwise, you might want to put some thought into it to make it fun. If someone is driving a wagon, you might say that the wagon has been souped up to be a little faster and maybe it has mounted crossbows for the other party members to get in on the action.

However you soup up the getaway vehicle, make sure the pursuing vehicles can still stand a match for it. So if you do have a souped up wagon, then maybe flying machines are what are chasing the party? However cool the party makes their getaway vehicle, it’s still a challenge to actually getaway.

You’ll also want to come up with a fair bit of chase complications, as you naturally would for any singular chase. In this case, one of the worse chase complications could be one of the party falls off or out of the getaway vehicle and gets caught. That could make for some really fun roleplaying later or perhaps another heist/jail break one-shot.

To there you have it, a DND Heist One shot. Now the only thing left is to actually play the one-shot, and let me tell you, that’s also a very fun part.

Your Players’ Planning Phase

Because you’ve done all of the work, we won’t go through playing the entire one shot. That said, Heist one-shots might have a little bit more involved beginning than other one-shots. That’s because unless you are a merciful DM and you decide to give your party the plan, your party needs to do the planning to pull off the heist.

This planning phase might be a separate session (probably preferable that way) or if you think you can squeeze it in, the first thing you do in the session. The way I see it, the planning phase will likely include 3 facets; Research, Plan Making, Resource Gathering.

Research

Again, unless you decide to be a benevolent DM (boo!) your players won’t have very much knowledge of the target location. This is pretty standard when it comes to heist shows. Usually, they start with just an idea (let’s steal XYZ) and then the party spends a good deal amount of time getting information so that they can make their plan. There are a few ways that your party can get information.

Informants: The party could rely on informants to tell them important aspects of the location where the target object is stored. There is an inherent risk to using an informant. If the informant is not loyal then this naturally leads to the party being double crossed, an excellent mid-heist complication. On the other hand, using an informant could grant the party special information that they would never get otherwise. An informant can be willing or unwilling. What that means is in one case they know that they are giving up information and in another case they are either doing it under duress or have been fooled into a false sense of security. Both have their pros and cons. If the party wants to try and talk to an informant, ask them specifically what type of informant they want to reach and how they would get the informant to talk. Common examples are guards, building staff, criminal informants, passersby that can get access because they aren’t criminals.

Staking Out the Location: One of the simplest ways to get information about the target location is simply to watch and observe the location, learning what they can. If your players choose this option, then either skip over it really fast because it is literally just watching and waiting, or make it so there is an actual threat of being discovered. Maybe the head of security ends up having lunch at the restaurant where most of the party is sitting, or perhaps their stakeout vehicle is getting towed or something. Just make it interesting or skip over it and get to the good stuff.

A Minor Heist: Another way the crew can go about researching and obtaining information for the heist is with a smaller, lower-risk heist. This is actually what I’m making some provisions for in my game with Hezriel’s tower. I figure the party will need a layout of the building so they could decide to sneak into City Hall, into the Records Department and just steal a copy of the blueprints of the building. Obviously, this isn’t the full heist so it won’t be as in depth and I will probably wing a lot of it, but the idea is that your party can go somewhere and steal (or purchase I guess) some valuable information about the location of the heist or some of its defenses.

There are likely a few other ways the party could do research, but you get the general idea. Because a lot of this is going to be pretty boring, you could just have your party do this stuff before the actual session of the one-shot. Basically send texts or such and have your party make rolls and then you can supply them with the information they need, or tell them they weren’t able to get it.

Plan Making

The next phase of the Plan phase is the actual planning itself. A heist is a complicated thing with lots of moving parts. So you’ll want to give your players some time to make a plan and see if they can put it all together. You might consider giving them a time limit in real life to make it a little more challenging or just let them go at it. Because the planning phase could be drawn out and possibly take a long time, I wouldn’t recommend doing it on the same day of the actual one-shot. Try doing it on a separate day or over text or email or something. That way when the one-shot comes, you get all the time to mess with the party haha.

Resource Gathering

An optional phase is the resource gathering phase. Naturally, your players will have hatched a plan by now. If you choose to do the resource gathering phase, you simply tell your players that they have a certain amount of money. With that money they can acquire certain items that may be useful to them in the heist. For example, your group may want a Ring of Invisibility for one of its members, or perhaps an Anti-Magic Gun. Each of those items will cost different amounts. If your party runs out of money or just chooses to not use their gold, you could have them attempt to steal such weapons. Remember, there are consequences with everything. If my party wants to steal an item for their heist, I’ll fulfill that request with a simple check. But then I’m going to have the people my party stole from show up during the heist and muck it all up as a complication. Everything has consequences.

After resource gathering, you’re all set to play the game.

Whether you intend to pull-off a serious one-shot like Oceans Eleven, or one that’s a little more light-hearted like Logan Lucky, I’m here for it. I love heists and ensemble shows and I would love to hear how yours goes. Hopefully with these tips and this frameworks, you are more willing to try creating a session like this. Regardless, my hope is that together, we’ve been able to help you be a better DM.

Thanks for listening to today’s show. As always, we appreciate your massive support (and yes, if you listened this far, you’ve been a massive support). If you want to do more to support us, just leave a rating and review which will help us be found by other prospective DMs. make sure to follow us on Instagram at how to be a better DM and on Tik Tok at session0studios. Finally, make sure you’re taking care of yourself and your loved ones and that you have a little bit of fun every single day. I’ve been your host, Justin Lewis and we’ll be back next week with another amazing episode. Until then, my friends, let’s roll initiative.

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Subject Line: DM now stands for Devlish Mastermind 👿

Hey there

Justin from Session 0 Studios and the host of How to Be a Better DM.

This week, we published an episode about why and how to write a D&D Heist One-Shot. If you haven’t listened to it already, here’s the link for you:

Regardless of if you have listened to it, I learned a couple tips, myself, for basically any type of adventure that you create. Let me share them real quick.

Start with the Layout: It is so much easier to visualize things when you make a map of the world, continent, country, region, city, building or location. Once you have that, you can fill it with details easily.

Pick the major players: Once you have the location, if you can decide who the characters are (for the most part, of course some will be “discovered” naturally), then you are well on your way to a very good plot

Decide on the Complication (The Twist): Generally having the location and the characters will naturally lead into the plot of the story. The last thing to do is turn the plot on its head by introducing a major complication that makes things much more difficult for the party.

With those 3 simple steps, writing one shots or any adventure can become a lot easier and hopefully take you a lot less time.

Thanks for your weekly and even daily support. You are why we do this.

Justin Lewis