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In my role as a DM, I historically avoided significant use of randomization during my tabletop roleplaying adventures. My preference was for story direction and session development to be determined by character actions instead of random chance. That said, I chose to alter my method, and I'm truly glad I did.

The Catalyst: Watching an Improvised Tool

A popular streamed game features a DM who regularly requests "chance rolls" from the participants. The process entails choosing a specific dice and defining possible results contingent on the number. It's essentially no distinct from rolling on a pre-generated chart, these get invented in the moment when a player's action doesn't have a obvious resolution.

I opted to test this method at my own table, mainly because it looked interesting and provided a change from my usual habits. The results were eye-opening, prompting me to reconsider the perennial dynamic between planning and spontaneity in a roleplaying game.

An Emotional Session Moment

During one session, my players had survived a massive battle. Afterwards, a cleric character wondered if two key NPCs—a brother and sister—had survived. In place of choosing an outcome, I handed it over to chance. I asked the player to roll a d20. The stakes were: on a 1-4, both were killed; on a 5-9, only one would die; a high roll, they both lived.

Fate decreed a 4. This triggered a deeply moving moment where the adventurers found the corpses of their allies, still united in death. The cleric held a ceremony, which was uniquely significant due to prior story developments. As a final reward, I decided that the forms were strangely restored, containing a enchanted item. By chance, the bead's contained spell was exactly what the party required to address another pressing quest obstacle. It's impossible to script these kinds of magical coincidences.

Honing Your Improvisation

This incident caused me to question if randomization and making it up are truly the essence of this game. While you are a detail-oriented DM, your skill to pivot can rust. Groups frequently excel at derailing the most carefully laid plots. Therefore, a skilled DM must be able to pivot effectively and invent content in the moment.

Using luck rolls is a fantastic way to practice these talents without venturing too far outside your comfort zone. The strategy is to deploy them for small-scale circumstances that won't drastically alter the session's primary direction. For instance, I would not employ it to decide if the king's advisor is a traitor. Instead, I would consider using it to figure out whether the characters enter a room just in time to see a critical event occurs.

Enhancing Shared Narrative

Luck rolls also serves to keep players engaged and create the feeling that the adventure is dynamic, shaping in reaction to their actions in real-time. It prevents the feeling that they are merely actors in a pre-written story, thereby bolstering the shared nature of storytelling.

Randomization has historically been embedded in the core of D&D. Original D&D were enamored with charts, which made sense for a playstyle focused on exploration. While contemporary D&D frequently focuses on story and character, leading many DMs to feel they require detailed plans, it's not necessarily the only path.

Finding the Right Balance

It is perfectly nothing wrong with being prepared. But, there is also no issue with letting go and letting the rolls to determine certain outcomes rather than you. Authority is a significant part of a DM's job. We need it to run the game, yet we can be reluctant to give some up, in situations where doing so can lead to great moments.

The core recommendation is this: Do not fear of letting go of your plan. Embrace a little randomness for minor details. It may discover that the organic story beat is far more powerful than anything you would have pre-written in advance.