How D&D Makes Me a Better CEO
I’ve been running D&D campaigns for decades. I currently DM “Eberron: Oracle of War” for 4-6 players. We started during the pandemic and we’re still going. The characters are level 16 now, basically invincible, and about to lead a war against The Lord of Blades. I also run multiple companies. These are not unrelated facts.
The main thing D&D has taught me about leadership: don’t try to control the game. Let it play out. Roll with the punches. Make sure everyone’s having fun. Build up ideas instead of tearing them down.
That’s it. That’s the whole lesson. Everything else is just examples.
”I’ll Allow It”
My players are adorable chaos monkeys. Someone will announce they want to try something completely insane. Grapple the dragon mid-flight. Convince the war criminal he’s actually a ghost. Use a bag of holding as a tactical weapon in a way that technically doesn’t violate the laws of physics (but definitely violates their spirit).
I’ll pause. Figure out how to make it work in an interesting way. Then: “I’ll allow it.”
It’s my version of “yes, and.” Matt Mercer calls it the “rule of cool.” I just think of it as “that’s so crazy it just might work,” which is something I say in both D&D and business more often than I probably should.
A bad DM hears an unexpected idea and looks for reasons to say no. A good DM hears an unexpected idea and figures out how to say yes in a way that makes the story better. The same is true for CEOs. When someone on your team brings you a wild approach, you have two options: shut it down because it wasn’t in the plan, or pause, figure out how it might work, and say “I’ll allow it.”
The second option produces better companies. It also produces better D&D sessions. The correlation is not a coincidence.
Don’t Control the Game
I plan my sessions. I build maps, write NPC dialogue, design encounters with balanced challenge ratings. Then my players talk their way past the dragon, befriend the villain, or burn down the building I spent an hour detailing.
(Six years into this campaign, my players have refined the art of finding the one solution I didn’t prepare for. At level 16, they have enough power to make almost any terrible idea actually work, which makes my job both harder and more entertaining.)
New DMs make the same mistake new CEOs make: they try to force the story. They have a plot they wrote, and they’re going to make the players follow it whether they like it or not. The players can feel it. They disengage. The sessions get flat. The DM works harder and harder to maintain control, and the game gets worse and worse.
The fix is counterintuitive. Let go. Stop trying to control where the story goes. Your job isn’t to write the story. Your job is to create a world interesting enough that the story writes itself.
I ran interRel for 25 years. The best ideas almost never came from me. They came from people who felt safe enough to pitch something unexpected. My job was to build the world those ideas could happen in, then get out of the way. Same thing I do behind the DM screen every week.
Make Sure Everyone’s Having Fun
Every D&D party needs a mix. Tank, healer, damage dealer, someone who can pick locks and charm guards. You don’t build a party of six barbarians. (I’ve seen someone try. They solved every problem with violence and couldn’t open a single door. The campaign lasted three sessions.)
But having the right mix isn’t enough. The DM has to make sure every player gets their moment. The fighter needs combat. The bard needs social encounters. The rogue needs something to steal. If half your table is bored because the session only caters to one play style, you’ve failed as a DM regardless of how clever your plot is.
A CEO who only creates opportunities for one type of contributor is running a bad campaign. My Clifton StrengthsFinder says my top result is Competition. That’s useful in a founder. A full company of people whose top strength is Competition would be a nightmare. You’d have a team that excels at winning arguments against each other and ships nothing.
The most important DM skill isn’t rules mastery or storytelling or encounter design. It’s reading the table. Noticing when a player hasn’t talked in twenty minutes. Picking up on someone who’s frustrated, even when they’re not saying so. Every effective CEO I know has this same skill. They walk into a room and immediately sense who’s engaged, who’s checked out, and what’s not being said.
The Safe Space to Practice
Here’s the part that makes D&D genuinely special as leadership training: it’s a structured social environment where you get to practice all of this with zero real-world consequences.
When your carefully planned encounter falls apart, nobody loses their job. When a player makes a terrible decision, the consequence is a character sheet, not a quarterly earnings call. When you fail to read the table and half your players check out, you can fix it next week. You get unlimited reps at building a shared world, resolving conflicts, improvising under pressure, and keeping a diverse group of people engaged and moving forward together.
(Also, you get to fight dragons. Most MBA programs do not include this, which feels like an oversight.)
You can learn leadership from management books (and I have a Master of Data Science from SMU, so I’m clearly not anti-education). But D&D taught me to read a room, build up ideas instead of shutting them down, and let go of control, every week, for years. That’s a lot of reps. More than any leadership seminar offers, and considerably cheaper.
My father used to say “if you’re going to laugh about it someday, laugh about it now.” D&D is leadership lessons you can laugh about in real time, in a world you built together, with people who keep showing up because the game is worth playing.
So if you ever have an idea that’s so crazy it just might work, tell me. Knowing me, I’ll allow it.