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When I am a DM, I historically shied away from extensive use of randomization during my tabletop roleplaying games. My preference was for the plot and session development to be guided by player choice instead of random chance. That said, I opted to try something different, and I'm truly glad I did.

The Inspiration: Watching an Improvised Tool

An influential actual-play show utilizes a DM who frequently requests "luck rolls" from the adventurers. He does this by selecting a polyhedral and assigning consequences based on the result. It's essentially no unlike consulting a random table, these are devised on the spot when a player's action lacks a clear outcome.

I chose to experiment with this approach at my own table, mostly because it appeared interesting and provided a departure from my normal practice. The outcome were fantastic, prompting me to reconsider the ongoing tension between planning and improvisation in a D&D campaign.

A Powerful Session Moment

At a session, my group had survived a massive fight. When the dust settled, a player asked about two beloved NPCs—a brother and sister—had made it. Instead of choosing an outcome, I let the dice decide. I instructed the player to make a twenty-sided die roll. I defined the outcomes as: a low roll, both died; on a 5-9, only one succumbed; on a 10+, they made it.

Fate decreed a 4. This resulted in a deeply poignant scene where the party discovered the bodies of their friends, forever holding hands in death. The cleric conducted funeral rites, which was especially powerful due to earlier character interactions. In a concluding touch, I improvised that the forms were miraculously transformed, containing a spell-storing object. By chance, the item's magical effect was perfectly what the party needed to resolve another major situation. One just orchestrate this type of serendipitous coincidences.

Honing Your Improvisation

This experience led me to ponder if chance and spontaneity are truly the essence of tabletop RPGs. While you are a detail-oriented DM, your ability to adapt can rust. Adventurers frequently take delight in upending the best constructed plans. Therefore, a skilled DM has to be able to adapt swiftly and create content on the fly.

Utilizing luck rolls is a fantastic way to train these talents without venturing too far outside your preparation. The trick is to apply them for low-stakes situations that don't fundamentally change the session's primary direction. As an example, I would avoid using it to establish if the king's advisor is a secret enemy. Instead, I could use it to figure out if the PCs enter a room just in time to see a critical event takes place.

Empowering Player Agency

Spontaneous randomization also helps keep players engaged and cultivate the feeling that the story is dynamic, evolving according to their decisions in real-time. It reduces the perception that they are merely characters in a rigidly planned script, thereby strengthening the collaborative aspect of the game.

This approach has historically been part of the game's DNA. The game's roots were filled with charts, which fit a game focused on treasure hunting. Although contemporary D&D frequently focuses on story and character, leading many DMs to feel they must prep extensively, this isn't always the best approach.

Striking the Healthy Equilibrium

Absolutely no problem with doing your prep. But, there is also no issue with letting go and letting the rolls to determine certain outcomes instead of you. Direction is a major part of a DM's responsibilities. We need it to run the game, yet we often struggle to cede it, in situations where doing so could be beneficial.

A piece of advice is this: Have no fear of temporarily losing the reins. Embrace a little randomness for smaller outcomes. It may find that the surprising result is far more powerful than anything you would have scripted in advance.