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As a Dungeon Master, I traditionally steered clear of extensive use of chance during my D&D games. I preferred was for story direction and session development to be guided by deliberate decisions rather than the roll of a die. Recently, I chose to try something different, and I'm incredibly glad I did.

The Spark: Watching an Improvised Tool

A popular actual-play show features a DM who frequently calls for "chance rolls" from the players. He does this by choosing a polyhedral and outlining potential outcomes tied to the number. It's fundamentally no different from rolling on a random table, these are created in the moment when a character's decision has no clear outcome.

I opted to test this technique at my own session, primarily because it seemed interesting and offered a departure from my standard routine. The results were eye-opening, prompting me to reconsider the often-debated dynamic between planning and improvisation in a tabletop session.

An Emotional In-Game Example

In a recent session, my party had survived a massive conflict. When the dust settled, a cleric character inquired after two key NPCs—a pair—had made it. Instead of deciding myself, I let the dice decide. I told the player to roll a d20. I defined the outcomes as: on a 1-4, both would perish; on a 5-9, a single one succumbed; a high roll, they survived.

The die came up a 4. This triggered a incredibly poignant scene where the party found the corpses of their friends, forever united in their final moments. The group conducted a ceremony, which was especially meaningful due to prior roleplaying. As a parting gesture, I decided that the forms were miraculously transformed, showing a magical Prayer Bead. I rolled for, the bead's contained spell was precisely what the group required to resolve another pressing story problem. It's impossible to orchestrate such perfect moments.

Improving On-the-Spot Skills

This event led me to ponder if improvisation and thinking on your feet are in fact the essence of this game. While you are a prep-heavy DM, your skill to pivot may atrophy. Players frequently excel at derailing the most detailed plans. Therefore, a skilled DM must be able to pivot effectively and fabricate scenarios in real-time.

Using on-the-spot randomization is a great way to practice these skills without venturing too far outside your preparation. The trick is to use them for low-stakes circumstances that have a limited impact on the session's primary direction. As an example, I wouldn't use it to establish if the central plot figure is a secret enemy. However, I could use it to determine whether the characters arrive right after a major incident takes place.

Strengthening Player Agency

Spontaneous randomization also helps maintain tension and cultivate the impression that the adventure is responsive, progressing according to their decisions immediately. It combats the perception that they are merely actors in a pre-written story, thereby bolstering the shared nature of storytelling.

Randomization has historically been integral to the core of D&D. Early editions were enamored with encounter generators, which made sense for a game focused on exploration. Although contemporary D&D often prioritizes narrative and role-play, leading many DMs to feel they must prep extensively, that may not be the best approach.

Striking the Healthy Equilibrium

There is absolutely no issue with thorough preparation. But, equally valid no issue with stepping back and letting the dice to guide minor details in place of you. Direction is a significant part of a DM's responsibilities. We require it to manage the world, yet we can be reluctant to give some up, at times when doing so can lead to great moments.

My final suggestion is this: Do not fear of relinquishing a bit of control. Try a little randomness for smaller outcomes. It may discover that the surprising result is infinitely more rewarding than anything you might have pre-written by yourself.