For almost 6 years, I've had a weekly game of Dungeons & Dragons going with a close group of friends. Usually the task of running the game has been something that I've taken on myself. In acting as the group's Dungeon Master, I find a lot of enjoyment in both the creative outlet it provides and the opportunity to participate in a shared storytelling experience.
If you’ve ever sat behind a Dungeon Master’s screen, you already know one of the best-kept secrets in creative leadership: success comes from balancing preparation with improvisation.
On paper, Dungeons & Dragons is a game built on rules, numbers, and probabilities. Players agree to operate within a shared framework. But once the adventure begins, no session has ever gone exactly as planned. Characters go left when you built encounters to the right. They charm the villain you expected them to fight. They throw you curveballs you could never have scripted.
A Dungeon Master’s real job isn’t to control the story, it’s to guide a group of people through an experience where the unexpected is guaranteed.
And that’s exactly what creative leaders do every day.
Knowing the Rules Well Enough to Break Them Gracefully
A DM doesn’t memorize every rule. They understand just enough of the system, and the story they want to tell, to stay one step ahead of the players. That foundation gives them the freedom to respond to surprises without derailing the adventure.
Creative leadership works the same way.
You don’t need exhaustive documentation, pixel-perfect plans, or airtight certainty. In fact, over-planning can trap you in rigidity, forcing you to drag a team back to a predetermined path long after the world around you has changed.
On the other hand, under-planning leads to chaos: no direction, no momentum, no sense of purpose.
The real craft is finding that sweet spot, planning just enough to create structure, while leaving room to adapt as new information rolls in.
Improv, but Informed
The best DMs aren’t surprised that surprises happen. They’re prepared to be surprised.
They embrace the moment when a player asks, “What if I try this?” They know the world well enough to riff, respond, and turn that unexpected idea into a story beat that feels intentional. And if the players trust the DM, they’ll never know the ending wasn’t planned from the start, they’ll just remember how the journey felt.
Creative leaders operate in the same space. Projects evolve. Client needs shift. Teams discover ideas mid-stream. You can’t plan for everything, but you can build the confidence to say:
“I didn’t expect that but we can roll with it.”
That’s not luck. It's practice and presence. It's knowing where the boundaries are, so you can bend everything inside them.
The Adventure that is Built on Trust
The greatest campaigns aren’t memorable because nothing went wrong, they’re memorable because everyone at the table trusted each other enough to take risks, pivot, and keep moving when things did go wrong.
Creative teams need the same trust:
- Trust that you’ve prepared enough to steer the ship
- Trust that they can bring ideas you didn’t expect
- Trust that the story is co-created, not dictated
- Trust that the ending can change without feeling like a failure
When people feel that trust, they stop trying to “get it right” and start trying to make something great. They take chances. They contribute more freely. They follow the fun.
Leading Like a Dungeon Master
The crossover is simple but powerful:
Creative leadership isn’t about control, it’s about guided collaboration in a world that refuses to stay on script.
A good Dungeon Master (and a good creative leader) must:
- Prepare enough to be confident
- Adapt quickly when the world shifts
- Accept new information gracefully
- Keep the experience moving
- Invite the team into the story
- Build trust by honoring contributions, not dictating outcomes
Because whether it’s a product launch or a dungeon crawl, the goal isn’t to force everyone down the path you planned. It’s to help your team believe the ending you arrive at together is exactly where the story was always meant to go.
The magic happens in the unexpected. The skill lies in how you respond.
And the journey? That’s where real creative leadership is forged.