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When I am a game master, I usually steered clear of heavy use of luck during my D&D sessions. My preference was for the plot and what happened in a game to be shaped by deliberate decisions as opposed to the roll of a die. However, I decided to try something different, and I'm very glad I did.

The Catalyst: Observing 'Luck Rolls'

A popular actual-play show showcases a DM who regularly calls for "luck rolls" from the participants. This involves picking a specific dice and assigning possible results contingent on the number. It's at its core no distinct from consulting a pre-generated chart, these get invented spontaneously when a player's action lacks a clear outcome.

I chose to experiment with this technique at my own session, mostly because it looked engaging and presented a departure from my usual habits. The outcome were eye-opening, prompting me to think deeply about the ongoing balance between planning and spontaneity in a D&D campaign.

A Memorable Session Moment

At a session, my players had concluded a city-wide battle. Afterwards, a cleric character inquired after two beloved NPCs—a sibling duo—had lived. Rather than deciding myself, I asked for a roll. I asked 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 incredibly poignant sequence where the adventurers came upon the remains of their friends, forever united in death. The group held funeral rites, which was particularly significant due to previous character interactions. As a final gesture, I decided that the forms were suddenly transformed, revealing a magical Prayer Bead. I rolled for, the bead's contained spell was perfectly what the party required to solve another major quest obstacle. You simply plan such serendipitous story beats.

Improving Your Improvisation

This event led me to ponder if chance and making it up are truly the beating heart of this game. While you are a detail-oriented DM, your improvisation muscles need exercise. Adventurers often excel at upending the best constructed narratives. Therefore, a skilled DM must be able to pivot effectively and invent details in the moment.

Using on-the-spot randomization is a excellent way to train these talents without venturing too far outside your comfort zone. The key is to apply them for small-scale decisions that don't fundamentally change the session's primary direction. To illustrate, I would avoid using it to determine if the main villain is a traitor. Instead, I would consider using it to determine if the party reach a location moments before a critical event takes place.

Strengthening Shared Narrative

Spontaneous randomization also helps keep players engaged and create the impression that the story is dynamic, shaping according to their choices in real-time. It prevents the feeling that they are merely pawns in a DM's sole narrative, thereby enhancing the collaborative aspect of roleplaying.

Randomization has historically been part of the original design. The game's roots were reliant on random tables, which fit a playstyle focused on dungeon crawling. While contemporary D&D tends to prioritizes plot-driven play, leading many DMs to feel they require detailed plans, this isn't always the only path.

Striking the Right Balance

It is perfectly nothing wrong with doing your prep. However, there is also no problem with relinquishing control and allowing the whim of chance to determine certain outcomes in place of you. Authority is a big part of a DM's role. We need it to run the game, yet we often struggle to give some up, at times when doing so might improve the game.

My final advice is this: Don't be afraid of relinquishing a bit of control. Try a little improvisation for minor details. The result could find that the surprising result is far more rewarding than anything you would have planned by yourself.