Yes, I know—“better manager” is obviously a self-assessment. But hear me out.
I discovered Dungeons & Dragons late, in 2023, after watching Dungeons & Dragons: Honor Among Thieves and playing Baldur’s Gate 3. What followed in 2024 and 2025 was a full-blown obsession. I spent almost every weekend playing D&D—at the local game shop, online, anywhere I could find a table.
It’s hard to describe D&D as just a game. It has mechanics, sure, but it’s really shared storytelling and bonding between people who might have nothing else in common. Shared adventure, problem-solving, empathy—it teaches you how to truly be with others, to build connection through experience and memory. It might be one of the most natural ways we have to connect as humans, something we’ve maybe forgotten in modern times. But I digress (I could talk about D&D all day).
At the start of 2025, I decided to try being a Game Master. Thinking back, I had literally no idea what I was doing — the first sessions were probably terrible (thank you to everyone who stuck around). On the surface, GM-ing seemed like it was mostly about enforcing mechanics. I was very wrong.
I read some GM guides but ended up improvising most of what I know now. What I didn’t expect was how much GM-ing would make me a better manager at work—or at least, help management make a lot more sense (to me). The two seem to feed into each other in a continuous feedback loop.
Stepping Back Without Losing Control
One thing I’m most grateful for as a GM is how comfortable it’s made me with “letting go” as a manager. This isn’t the same as abandoning goals or roadmaps. But I’ve gotten comfortable setting context, defining a “clear enough” goal, and then stepping back to watch how people journey toward it.
The path might be a straight line. It might be squiggly. It might fall off the edge entirely. But learning to nudge indirectly and let players find their own way is a huge part of storytelling—show, don’t tell. In management, it’s equally powerful. Nothing sticks with people more than discoveries they make themselves. You just have to gently nudge them toward it.
To do this effectively as a GM, I have to be crystal clear on where the story is meant to go—the “checkpoints.” At work, those are goals and deliverables. This clarity makes it easy to figure out what’s actually important (the objective, the north star) versus what’s just part of the journey (the storytelling). The goal isn’t meant to be prescriptive. The journey tells the story. And just as players are the heroes journeying through your D&D world, your team members are the heroes of the team’s journey at work.
If this was obvious to everyone I guess I was just behind. To me this is one of the most useful skill that D&D GMing has taught me and life in general.
Keeping Track of Parallel Threads
As GM you are keeping track of a lot of things:
- Each players’ journey
- Players journey overlap with each other
- NPC journey(s)
- NPC journey overlap with players
- Major story arcs
- Minor story arcs, and side quests
- Worlds, in each their parallel timelines
- … (everything else like items, and especially in custom campaigns like mine, custom lore details, history, descriptions, …)
I used to think of project dependencies like layers of maps in a 3D cube. D&D took this to a whole new level — meshes within meshes across meshes, with no perfect cubes but amorphous graphs. You get incredibly good at mentally tracing connections, predicting outcomes, rearranging pieces on the fly. One player’s choice ripples through everything like a butterfly effect. It’s become something I genuinely enjoy, almost like a superpower.
I haven’t found a perfect tool for this yet (I’m making do with scattered notes and my brain doing most of the heavy lifting). But the mental exercise has drastically improved my memory and pattern recognition across all of life.
Being Patient with Reveals
I’ve become comfortable with gradual surprises — details that may take weeks, months, or even a year to unfold. Letting players discover things through their own choices, at their own pace, is what makes the story theirs. Sometimes the story doesn’t move as fast as I’d like. Sometimes it takes unexpected turns. But that’s the beauty of shared storytelling—and it often makes the reveals even better than I’d planned.
Staged, incremental reveals rather than relying on one “big bang moment” mirrors how life actually works. I’ve translated this into management too, whether I’m delivering great news or hard news. Either way, it makes things easier for people to digest and understand.
Learning to Love the unexpected
Like most people, I used to fear the unexpected - that sense of being out of control, and I’d be lying if I said I stopped fearing entirely. But if D&D has taught me one thing above all else, it’s learning to love the unexpected.
No D&D session is ever the same, even with the same plot and players. Random decisions, dice rolls, chaos — sometimes you just have to relax and let it reign. Things don’t always go the way you hoped and you have to puzzle solve your way out of it, just like in life. Sometimes things go really badly; sometimes all the dice rolls are in your favor - you just never know, but you can certainly try to line up factors that are within your control to increase the chances of getting the outcome you want. I’ve never been more comfortable with things going sideways than I am now. Embracing the mess, appreciating the human experience of it all, and turning it into something we’ll laugh about later — that’s why we play, why we live, how we have fun. I suppose this last part isn’t about just D&D, or managing - but living in general.