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In my role as a game master, I usually steered clear of extensive use of chance during my D&D adventures. My preference was for the plot and session development to be guided by deliberate decisions rather than random chance. Recently, I opted to change my approach, and I'm very glad I did.

The Inspiration: Seeing 'Luck Rolls'

An influential actual-play show utilizes a DM who regularly calls for "chance rolls" from the players. This involves picking a polyhedral and outlining possible results tied to the result. It's essentially no different from using a pre-generated chart, these are devised spontaneously when a player's action has no obvious conclusion.

I chose to experiment with this method at my own game, primarily because it appeared interesting and offered a departure from my normal practice. The results were eye-opening, prompting me to reflect on the ongoing balance between preparation and randomization in a D&D campaign.

A Powerful Session Moment

During one session, my group had survived a massive conflict. Afterwards, a cleric character inquired after two friendly NPCs—a pair—had survived. In place of choosing an outcome, I handed it over to chance. I asked the player to make a twenty-sided die roll. I defined the outcomes as: a low roll, both would perish; on a 5-9, only one succumbed; on a 10+, they both lived.

The player rolled a 4. This triggered a incredibly emotional moment where the adventurers found the corpses of their friends, still united in death. The party conducted last rites, which was especially significant due to earlier character interactions. In a concluding reward, I improvised that the forms were suddenly restored, revealing a enchanted item. I randomized, the item's magical effect was exactly what the group required to solve another pressing quest obstacle. You simply plan these kinds of perfect coincidences.

Honing On-the-Spot Skills

This incident caused me to question if randomization and spontaneity are in fact the essence of this game. Even if you are a meticulously planning DM, your skill to pivot can rust. Adventurers frequently excel at derailing the most detailed plans. Therefore, a skilled DM needs to be able to adapt swiftly and fabricate scenarios in the moment.

Using on-the-spot randomization is a great way to develop these abilities without straying too much outside your preparation. The key is to apply them for minor decisions that won't drastically alter the session's primary direction. For instance, I would not employ it to determine if the central plot figure is a secret enemy. But, I would consider using it to determine if the PCs enter a room moments before a major incident takes place.

Enhancing Player Agency

Spontaneous randomization also serves to make players feel invested and cultivate the impression that the game world is dynamic, progressing in reaction to their choices immediately. It combats the feeling that they are merely pawns in a rigidly planned script, thereby bolstering the cooperative nature of the game.

This philosophy has always been part of the core of D&D. Original D&D were filled with random tables, which fit a playstyle focused on treasure hunting. Although contemporary D&D often prioritizes story and character, leading many DMs to feel they require detailed plans, it's not necessarily the only path.

Achieving the Sweet Spot

Absolutely no problem with doing your prep. Yet, equally valid no problem with relinquishing control and letting the whim of chance to guide minor details rather than you. Control is a big part of a DM's role. We require it to manage the world, yet we often struggle to release it, at times when doing so could be beneficial.

A piece of suggestion is this: Do not fear of relinquishing a bit of your plan. Try a little randomness for smaller outcomes. You might just create that the surprising result is significantly more rewarding than anything you would have planned on your own.