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When I am a game master, I historically shied away from heavy use of chance during my Dungeons & Dragons adventures. My preference was for story direction and session development to be shaped by character actions as opposed to random chance. That said, I chose to alter my method, and I'm very happy with the result.

The Spark: Observing a Custom Mechanic

A popular actual-play show features a DM who regularly requests "chance rolls" from the adventurers. The process entails picking a type of die and outlining potential outcomes contingent on the roll. While it's at its core no distinct from consulting a pre-generated chart, these are created in the moment when a course of events lacks a predetermined conclusion.

I chose to experiment with this approach at my own session, mostly because it seemed interesting and provided a departure from my standard routine. The outcome were fantastic, prompting me to reflect on the perennial tension between planning and randomization in a tabletop session.

An Emotional In-Game Example

At a session, my group had just emerged from a large-scale conflict. Afterwards, a cleric character asked about two key NPCs—a pair—had made it. Instead of choosing an outcome, I asked for a roll. I instructed the player to make a twenty-sided die roll. The stakes were: a low roll, both died; a middling roll, only one succumbed; a high roll, they both lived.

The die came up a 4. This resulted in a profoundly moving moment where the party found the remains of their allies, still holding hands in death. The group performed last rites, which was uniquely significant due to prior roleplaying. As a parting reward, I decided that the forms were miraculously restored, revealing a enchanted item. I randomized, the item's magical effect was exactly what the party required to resolve another critical situation. You simply orchestrate this type of serendipitous coincidences.

Improving On-the-Spot Skills

This incident led me to ponder if improvisation and thinking on your feet are actually the beating heart of this game. Although you are a prep-heavy DM, your skill to pivot need exercise. Adventurers often excel at upending the most detailed narratives. Therefore, a good DM needs to be able to adapt swiftly and invent details in the moment.

Employing similar mechanics is a great way to train these talents without straying too much outside your preparation. The strategy is to deploy them for low-stakes decisions that have a limited impact on the session's primary direction. To illustrate, I would not employ it to decide if the main villain is a secret enemy. Instead, I would consider using it to decide if the characters enter a room moments before a major incident unfolds.

Enhancing Player Agency

Spontaneous randomization also serves to maintain tension and foster the impression that the adventure is responsive, shaping according to their choices immediately. It reduces the feeling that they are merely pawns in a pre-written story, thereby strengthening the shared nature of storytelling.

This approach has historically been embedded in the original design. The game's roots were enamored with random tables, which made sense for a playstyle focused on dungeon crawling. Although contemporary D&D tends to prioritizes story and character, leading many DMs to feel they need exhaustive notes, it's not necessarily the best approach.

Finding the Right Balance

Absolutely nothing wrong with doing your prep. Yet, equally valid no issue with stepping back and permitting the dice to decide some things in place of you. Direction is a significant factor in a DM's role. We use it to manage the world, yet we frequently find it hard to cede it, in situations where doing so could be beneficial.

My final recommendation is this: Don't be afraid of relinquishing a bit of your plan. Try a little improvisation for smaller story elements. The result could discover that the unexpected outcome is infinitely more memorable than anything you could have pre-written on your own.