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As a Dungeon Master, I historically steered clear of heavy use of chance during my D&D games. I tended was for story direction and session development to be guided by character actions instead of the roll of a die. However, I opted to try something different, and I'm very happy with the result.

The Catalyst: Watching a Custom Mechanic

A popular actual-play show utilizes a DM who often calls for "fate rolls" from the adventurers. He does this by picking a type of die and defining potential outcomes tied to the result. It's at its core no unlike rolling on a pre-generated chart, these are created in the moment when a course of events doesn't have a predetermined outcome.

I decided to try this method at my own game, primarily because it looked engaging and provided a departure from my standard routine. The outcome were eye-opening, prompting me to think deeply about the perennial tension between preparation and spontaneity in a roleplaying game.

A Memorable In-Game Example

At a session, my group had just emerged from a large-scale battle. Afterwards, a player wondered if two beloved NPCs—a brother and sister—had made it. Instead of picking a fate, I asked for a roll. I instructed the player to make a twenty-sided die roll. The possible results were: a low roll, both would perish; on a 5-9, only one succumbed; on a 10+, they made it.

The player rolled a 4. This triggered a deeply emotional moment where the characters came upon the remains of their allies, forever holding hands in death. The party conducted last rites, which was uniquely powerful due to earlier character interactions. As a final touch, I chose that the remains were miraculously restored, showing a magical Prayer Bead. By chance, the bead's contained spell was exactly what the group needed to address another pressing story problem. It's impossible to plan such serendipitous moments.

Sharpening DM Agility

This incident led me to ponder if randomization and making it up are in fact the essence of this game. Even if you are a meticulously planning DM, your skill to pivot need exercise. Players reliably take delight in upending the most detailed plots. Therefore, a good DM needs to be able to think quickly and fabricate scenarios on the fly.

Employing similar mechanics is a fantastic way to practice these skills without going completely outside your comfort zone. The trick is to deploy them for small-scale situations that don't fundamentally change the session's primary direction. For instance, I would avoid using it to establish if the king's advisor is a secret enemy. However, I could use it to decide if the PCs arrive right after a critical event occurs.

Enhancing Collaborative Storytelling

Luck rolls also serves to make players feel invested and foster the sensation that the game world is alive, progressing based on their decisions in real-time. It prevents the sense that they are merely actors in a DM's sole narrative, thereby bolstering the cooperative aspect of storytelling.

This approach has always been part of the core of D&D. The game's roots were filled with charts, which made sense for a game focused on treasure hunting. Although current D&D tends to emphasizes narrative and role-play, leading many DMs to feel they require detailed plans, that may not be the only path.

Striking the Right Balance

Absolutely no problem with doing your prep. But, it's also fine no issue with relinquishing control and permitting the whim of chance to determine certain outcomes instead of you. Control is a major factor in a DM's role. We need it to facilitate play, yet we often struggle to give some up, at times when doing so might improve the game.

A piece of recommendation is this: Do not fear of letting go of your plan. Experiment with a little randomness for inconsequential story elements. The result could discover that the organic story beat is significantly more memorable than anything you would have planned by yourself.