Dragon Heist for D&D is out, and in several locations I've seen and heard people complain that the story is just not "heisty" enough. Beyond that, heists are a common thing a lot of groups want to pull off in their game, but they're tricky things. With that in mind, I want to go over some of the key elements of a good heist and how that can look in your game.
Three Main Story Beats
A heist breaks down to three main story beats: the plan, the execution, the escape.
The plan involves not just making a literal plan, but also the legwork and research involved in making a viable plan. Legwork is something a lot of Shadowrun players are familiar with - and some even love it - but it's not something super common in D&D in my experience. Legwork can be a lot of fun, but also involves a lot of prep by the GM. You need to know things like location, key NPCs, schedules for said NPCs, defenses, guards, and other obstacles that can come up. The players then figure out how they're going to find that information, and go do it to various degrees of success. Once they have the information they can gather resources and allies, and make their plan.
The execution is the actual performance of the heist. In movies this often gets less story time than the planning because a well executed plan is often less interesting than the formation of the plan. That said, we'll come back to execution in the next stage because as I just said, a plan that goes exactly to plan can be kind of boring.
The escape is the other part a lot of movies and stories for heists focus on. How the characters get away with the goods, or if they even do get away with the goods makes for an interesting tale. This is often the climax of a good heist story where the tensions are thickest, things happen fast, and you're left wondering if the characters will get away clean or not. More on this later too.
First, a safety note: think of complications in a heist story more like monkey wrenches than obstacles. Obstacles are things found with legwork and worked around in planning. Complications are monkey wrenches being thrown in to gum up the works of a machine in motion.
Things that go to plan are boring. Complications make boring things less boring. In general, every solid heist story should have several complications. Movies often like to throw one complication in right at the end of the planning phase. Some bit of information the characters were planning on is wrong. It's not an SMX 9000 safe but a Seculock 9950 which is a whole different breed of insane to get into. The town guard isn't whose watching over the meseum at night, but the King's elite unit of assassins and counter-spies. The point is, the first major complication comes when things are almost set and thus have to be pivoted around. Even better if these complications bring up character moments - that's the safe that got the Rogue busted before, or the unit of guards is the enforcer's old buddies with a grudge to settle.
Other complications happen during execution. Someone goes off routine. Someone is suspicious. Either way, something happens and while it doesn't knock the plan off the rails it threatens to do so. This means then that a character has to improv something to keep the plan going - often leaving someone else carrying an extra load too. These complications keep the execution fun, and people on their toes as the plan threatens to unravel, but the characters fight to keep everything going well if not smoothly.
Finally, by the escape, things are generally a mess. Maybe this is planned for. Maybe it's not. Either way, this stage is often full of small and major complications that people have to juke around or they're not getting out. If everything else has gone smooth, this is where you really want to go for it. This is also where you frequently see double crosses happen. Why? Because it's the best time. Other threats have been avoided, the prize is out in the open, so make the move now or lose the reward forever.
A Touch of the Absurd
A touch of the absurd can often be the difference between a good heist story and a great one. This is largely up to the players in their plan, but it's something to encourage. A bunch of Minis racing through sewers loaded down with gold is a little absurd. Matt Damon's giant prosthetic nose in Ocean's 13 is absurd. A souped up VW Bug doing things no VW Bug should ever be able to do is absurd. However, they are also a lot of fun and make for memorable moments.
Just remember, the idea is for a touch of the absurd, not a whole heaping spoonful. Absurdity is a spice, a pinch adds flavor but too much can spoil the whole meal.
Competition isn't needed for a heist. After all, just the idea of stealing from a group means there is opposition. That said, having a competing interest also going for the same thing can add a layer of complexity and fun that is something to behold.
This gives the players something dynamic they have to work around. They have their plan, their execution, and their escape, but so too does this other group. This means there is something in play, as dynamic as them, looking to do the same goal. Keep things set so that neither group can just murder the other, and let the hillarity ensure.