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As a Dungeon Master, I traditionally steered clear of significant use of chance during my D&D games. I preferred was for narrative flow and session development to be shaped by character actions rather than pure luck. Recently, I chose to try something different, and I'm incredibly glad I did.

The Inspiration: Observing an Improvised Tool

A well-known actual-play show utilizes a DM who frequently requests "fate rolls" from the players. The process entails picking a specific dice and assigning consequences contingent on the result. While it's at its core no unlike consulting a pre-generated chart, these are devised in the moment when a course of events has no predetermined outcome.

I chose to experiment with this technique at my own game, mostly because it looked novel and provided a departure from my normal practice. The outcome were fantastic, prompting me to think deeply about the ongoing dynamic between preparation and spontaneity in a D&D campaign.

A Memorable Session Moment

During one session, my party had survived a large-scale conflict. Afterwards, a cleric character asked about two key NPCs—a brother and sister—had made it. In place of choosing an outcome, I handed it over to chance. I told the player to roll a d20. The stakes were: on a 1-4, both would perish; on a 5-9, a single one would die; on a 10+, they survived.

Fate decreed a 4. This triggered a deeply poignant sequence where the characters found the corpses of their companions, still holding hands in death. The cleric performed a ceremony, which was uniquely meaningful due to previous roleplaying. As a final touch, I improvised that the remains were strangely transformed, containing a spell-storing object. I randomized, the item's magical effect was precisely what the group required to resolve another pressing story problem. It's impossible to plan this type of perfect story beats.

Honing Your Improvisation

This event led me to ponder if chance and spontaneity are in fact the core of this game. While you are a meticulously planning DM, your improvisation muscles can rust. Adventurers often excel at upending the most carefully laid plans. Therefore, a effective DM must be able to pivot effectively and fabricate scenarios on the fly.

Employing luck rolls is a excellent way to practice these talents without venturing too far outside your comfort zone. The strategy is to deploy them for minor situations that have a limited impact on the campaign's main plot. As an example, I wouldn't use it to determine if the central plot figure is a secret enemy. But, I would consider using it to determine whether the characters reach a location right after a major incident takes place.

Empowering Shared Narrative

Spontaneous randomization also serves to maintain tension and create the impression that the story is responsive, progressing in reaction to their decisions as they play. It combats the sense that they are merely characters in a rigidly planned narrative, thereby strengthening the shared nature of the game.

Randomization has historically been embedded in the original design. Original D&D were reliant on random tables, which suited a playstyle focused on dungeon crawling. Although modern D&D frequently prioritizes plot-driven play, leading many DMs to feel they require detailed plans, this isn't always the only path.

Striking the Sweet Spot

It is perfectly no problem with doing your prep. Yet, equally valid no issue with letting go and allowing the whim of chance to determine certain outcomes rather than you. Direction is a significant factor in a DM's role. We need it to facilitate play, yet we often struggle to cede it, even when doing so could be beneficial.

My final recommendation is this: Do not fear of temporarily losing your plan. Try a little chance for smaller outcomes. It may create that the organic story beat is infinitely more memorable than anything you might have pre-written by yourself.