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In my role as a DM, I historically steered clear of significant use of chance during my D&D sessions. I preferred was for story direction and session development to be determined by character actions as opposed to pure luck. Recently, I opted to try something different, and I'm very pleased with the outcome.

The Spark: Seeing an Improvised Tool

An influential streamed game utilizes a DM who often requests "chance rolls" from the adventurers. This involves selecting a polyhedral and assigning potential outcomes contingent on the number. While it's at its core no different from consulting a random table, these get invented spontaneously when a course of events doesn't have a clear resolution.

I chose to experiment with this approach at my own session, mostly because it seemed engaging and presented a change from my usual habits. The outcome were remarkable, prompting me to reflect on the ongoing dynamic between preparation and spontaneity in a tabletop session.

A Powerful In-Game Example

In a recent session, my party had survived a massive conflict. Later, a cleric character wondered if two key NPCs—a sibling duo—had survived. Rather than picking a fate, I asked for a roll. I asked the player to roll a d20. The stakes were: on a 1-4, both would perish; on a 5-9, a single one would die; a high roll, they both lived.

Fate decreed a 4. This resulted in a incredibly moving scene where the adventurers discovered the bodies of their companions, forever united in their final moments. The group held a ceremony, which was particularly meaningful due to prior character interactions. As a final touch, I improvised that the NPCs' bodies were strangely transformed, showing a enchanted item. I rolled for, the bead's contained spell was precisely what the group needed to solve another major story problem. It's impossible to script these kinds of magical coincidences.

Sharpening DM Agility

This experience caused me to question if improvisation and making it up are truly the core of tabletop RPGs. Although you are a detail-oriented DM, your ability to adapt may atrophy. Adventurers frequently find joy in upending the most carefully laid plans. Therefore, a good DM needs to be able to think quickly and fabricate scenarios in the moment.

Using luck rolls is a great way to develop these abilities without venturing too far outside your usual style. The strategy is to deploy them for minor decisions that don't fundamentally change the campaign's main plot. For instance, I would avoid using it to establish if the central plot figure is a secret enemy. Instead, I would consider using it to figure out if the party arrive just in time to see a major incident occurs.

Enhancing Shared Narrative

This technique also serves to maintain tension and create the sensation that the story is dynamic, evolving based on their choices as they play. It combats the perception that they are merely characters in a DM's sole script, thereby enhancing the collaborative foundation of storytelling.

This approach has historically been integral to the original design. Original D&D were enamored with encounter generators, which fit a game focused on dungeon crawling. Although modern D&D tends to emphasizes plot-driven play, leading many DMs to feel they need exhaustive notes, this isn't always the only path.

Achieving the Sweet Spot

Absolutely no problem with doing your prep. But, equally valid nothing wrong with stepping back and permitting the dice to guide minor details instead of you. Control is a big aspect of a DM's role. We require it to run the game, yet we frequently find it hard to release it, at times when doing so could be beneficial.

My final recommendation is this: Have no fear of relinquishing a bit of your plan. Embrace a little improvisation for inconsequential story elements. You might just find that the organic story beat is significantly more powerful than anything you might have pre-written on your own.