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As a DM, I historically steered clear of significant use of luck during my D&D sessions. My preference was for narrative flow and session development to be determined by player choice as opposed to pure luck. That said, I chose to alter my method, and I'm truly glad I did.

The Spark: Seeing an Improvised Tool

An influential podcast features a DM who frequently requests "luck rolls" from the players. He does this by picking a specific dice and assigning consequences contingent on the number. While it's fundamentally no unlike using a pre-generated chart, these get invented in the moment when a course of events has no predetermined conclusion.

I chose to experiment with this approach at my own table, primarily because it seemed novel and provided a break from my usual habits. The experience were remarkable, prompting me to reconsider the ongoing tension between planning and spontaneity in a tabletop session.

A Powerful Session Moment

During one session, my party had just emerged from a city-wide conflict. When the dust settled, a player asked about two beloved NPCs—a pair—had made it. Rather than picking a fate, I handed it over to chance. I instructed the player to make a twenty-sided die roll. I defined the outcomes as: on a 1-4, both died; on a 5-9, a single one succumbed; on a 10+, they survived.

The die came up a 4. This triggered a deeply moving scene where the characters came upon the corpses of their allies, forever clasped together in death. The group conducted funeral rites, which was particularly powerful due to earlier character interactions. As a final reward, I improvised that the NPCs' bodies were miraculously restored, showing a spell-storing object. I randomized, the item's magical effect was precisely what the party lacked to solve another critical situation. One just script these kinds of serendipitous story beats.

Honing Your Improvisation

This experience caused me to question if chance and thinking on your feet are in fact the essence of tabletop RPGs. Although you are a prep-heavy DM, your improvisation muscles can rust. Adventurers often find joy in derailing the most detailed plots. Therefore, a good DM must be able to think quickly and invent content in the moment.

Using luck rolls is a excellent way to practice these abilities without going completely outside your usual style. The trick is to deploy them for minor circumstances that won't drastically alter the session's primary direction. As an example, I would not employ it to determine if the king's advisor is a secret enemy. However, I might use it to figure out whether the PCs arrive right after a major incident unfolds.

Strengthening Shared Narrative

This technique also helps keep players engaged and cultivate the impression that the adventure is dynamic, evolving based on their choices in real-time. It reduces the perception that they are merely actors in a rigidly planned script, thereby enhancing the cooperative aspect of the game.

Randomization has long been embedded in the core of D&D. Original D&D were enamored with encounter generators, which fit a game focused on dungeon crawling. While current D&D tends to prioritizes story and character, leading many DMs to feel they require detailed plans, that may not be the required method.

Striking the Sweet Spot

There is absolutely nothing wrong with thorough preparation. However, it's also fine no issue with letting go and allowing the rolls to determine certain outcomes instead of you. Direction is a significant part of a DM's responsibilities. We require it to run the game, yet we frequently find it hard to cede it, even when doing so might improve the game.

The core suggestion is this: Have no fear of relinquishing a bit of your plan. Experiment with a little improvisation for minor story elements. You might just find that the unexpected outcome is significantly more memorable than anything you would have pre-written in advance.