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As a Dungeon Master, I historically steered clear of extensive use of chance during my D&D sessions. I preferred was for the plot and what happened in a game to be determined by deliberate decisions instead of the roll of a die. That said, I chose to try something different, and I'm very pleased with the outcome.

The Catalyst: Seeing 'Luck Rolls'

An influential podcast showcases a DM who regularly asks for "luck rolls" from the participants. This involves picking a polyhedral and outlining possible results contingent on the number. While it's fundamentally no distinct from rolling on a random table, these get invented on the spot when a course of events doesn't have a obvious resolution.

I chose to experiment with this technique at my own session, mostly because it seemed interesting and offered a break from my usual habits. The experience were fantastic, prompting me to reflect on the perennial balance between planning and randomization in a tabletop session.

A Powerful In-Game Example

During one session, my players had concluded a large-scale fight. Later, a player asked about two beloved NPCs—a brother and sister—had lived. In place of deciding myself, I let the dice decide. I instructed the player to make a twenty-sided die roll. The possible results were: on a 1-4, both were killed; on a 5-9, only one would die; a high roll, they both lived.

Fate decreed a 4. This triggered a profoundly emotional moment where the characters found the bodies of their allies, still holding hands in death. The cleric conducted a ceremony, which was uniquely meaningful due to prior roleplaying. As a final reward, I improvised that the remains were miraculously restored, revealing a enchanted item. I rolled for, the item's contained spell was precisely what the party needed to address another critical story problem. It's impossible to script such magical moments.

Improving DM Agility

This event led me to ponder if improvisation and thinking on your feet are actually the beating heart of this game. While you are a meticulously planning DM, your ability to adapt can rust. Groups frequently take delight in derailing the most detailed plots. Therefore, a good DM needs to be able to adapt swiftly and create scenarios in real-time.

Using on-the-spot randomization is a excellent way to train these skills without straying too much outside your comfort zone. The trick is to deploy them for minor circumstances that don't fundamentally change the overarching story. For instance, I would avoid using it to decide if the king's advisor is a secret enemy. However, I might use it to decide if the PCs arrive just in time to see a major incident occurs.

Empowering Shared Narrative

This technique also helps keep players engaged and create the impression that the adventure is alive, shaping according to their choices in real-time. It prevents the sense that they are merely characters in a DM's sole script, thereby strengthening the collaborative aspect of storytelling.

This approach has historically been part of the original design. Original D&D were enamored with random tables, which made sense for a playstyle focused on exploration. Although current D&D frequently prioritizes story and character, leading many DMs to feel they need exhaustive notes, this isn't always the only path.

Achieving the Right Balance

There is absolutely no problem with doing your prep. Yet, it's also fine no issue with stepping back and allowing the whim of chance to decide some things rather than you. Control is a major part of a DM's role. We need it to manage the world, yet we often struggle to give some up, even when doing so could be beneficial.

My final recommendation is this: Don't be afraid of letting go of control. Try a little improvisation for inconsequential story elements. It may discover that the organic story beat is far more memorable than anything you could have planned by yourself.