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In my role as a DM, I traditionally steered clear of heavy use of randomization during my tabletop roleplaying sessions. I tended was for story direction and session development to be guided by character actions instead of pure luck. Recently, I opted to alter my method, and I'm truly happy with the result.

The Catalyst: Seeing an Improvised Tool

A well-known actual-play show features a DM who regularly asks for "fate rolls" from the participants. He does this by selecting a specific dice and outlining potential outcomes based on the roll. It's at its core no distinct from consulting a pre-generated chart, these get invented spontaneously when a course of events has no obvious outcome.

I opted to test this technique at my own game, mainly because it looked engaging and provided a break from my standard routine. The results were eye-opening, prompting me to think deeply about the often-debated balance between preparation and spontaneity in a roleplaying game.

An Emotional Session Moment

During one session, my group had just emerged from a large-scale battle. Afterwards, a player inquired after two key NPCs—a brother and sister—had survived. In place of choosing an outcome, I asked for a roll. I instructed the player to roll a d20. The possible results were: on a 1-4, both would perish; on a 5-9, a single one would die; on a 10+, they made it.

The player rolled a 4. This resulted in a profoundly emotional sequence where the adventurers found the remains of their companions, forever clasped together in their final moments. The cleric performed funeral rites, which was particularly significant due to prior story developments. As a parting touch, I improvised that the remains were miraculously restored, showing a magical Prayer Bead. I randomized, the item's magical effect was exactly what the group needed to solve another pressing story problem. You simply orchestrate these kinds of magical moments.

Honing Your Improvisation

This experience caused me to question if improvisation and making it up are actually the core of D&D. Although you are a meticulously planning DM, your skill to pivot can rust. Adventurers frequently take delight in upending the most detailed plots. Therefore, a good DM needs to be able to pivot effectively and fabricate details in the moment.

Utilizing similar mechanics is a excellent way to develop these talents without straying too much outside your preparation. The trick is to apply them for minor situations that don't fundamentally change the campaign's main plot. For instance, I would not employ it to decide if the king's advisor is a traitor. But, I would consider using it to determine if the PCs enter a room moments before a critical event occurs.

Strengthening Player Agency

Spontaneous randomization also serves to make players feel invested and cultivate the impression that the adventure is dynamic, shaping according to their choices immediately. It combats the perception that they are merely pawns in a rigidly planned story, thereby strengthening the cooperative nature of roleplaying.

This approach has historically been part of the original design. Original D&D were enamored with encounter generators, which suited a playstyle focused on exploration. Although contemporary D&D tends to emphasizes plot-driven play, leading many DMs to feel they require detailed plans, it's not necessarily the only path.

Achieving the Right Balance

Absolutely nothing wrong with thorough preparation. Yet, equally valid no issue with relinquishing control and permitting the whim of chance to determine certain outcomes instead of you. Authority is a major factor in a DM's job. We need it to run the game, yet we often struggle to cede it, in situations where doing so might improve the game.

My final recommendation is this: Don't be afraid of relinquishing a bit of control. Experiment with a little randomness for smaller details. The result could discover that the surprising result is infinitely more rewarding than anything you would have pre-written on your own.