Roll to scale: Five entrepreneurial lessons from playing Dungeons & Dragons

Navigating the business world can feel treacherous. There are countless unforeseen obstacles, a glittering treasure awaiting those who survive, and the constant looming threat of ferocious fire-breathing … investors!

Don’t believe us? Check out this episode of Masters of Scale where founding host Reid Hoffman sits down with Hasbro CEO Chris Cocks to discuss the 50th anniversary of Dungeons & Dragons, how Hasbro has helped scale the brand to new heights, and the unexpected entrepreneurial lessons that you can take from playing the beloved game.?

A long-time player, Cocks credits D&D with teaching him important business skills as a 10-year-old.?

“It taught me about design, and about systems that underlie design,” Cocks says. “It really structured my thinking, and I became much more successful in school as a result. And it's kind of been foundational to how I approach business, how I approach problems, how I approach creative endeavors. And I'm not alone in that.”

So, grab your D20 and dust off your character sheets as we set off on a mini-adventure to explore the five best business lessons Reid and Chris mined from their decades of tabletop game play.

The importance of diverse teams

You find yourself in a tavern. As you approach the bar, a wealthy patron eyes the battered sword hanging from your belt and correctly identifies you as an entrepreneur. He’s got a job that’s perfect for someone of your skillset. Minimal risk, high dividends, and the opportunity to finally establish your brand.

But first, you’ll need a crew. You scan the bar and survey the motley collection of ruffians, sellswords, and digital marketers. As you assemble your party, remember that a variety of skills will be needed on this business venture.?

“Let's make sure we're not all a bunch of wizards going off to fight an army of orcs,” Cocks says, recounting his own realization that diverse teams breed success. “We're probably going to need … someone who can be like a barbarian or a warrior. We're probably going to need a healer to help back us up…a smooth talker, like a bard.”

In a good adventuring party, just like in business, team members should all have different strengths and weaknesses, allowing them to support and play off each other on their journey towards scale.?

Leadership requires charisma

Your party assembled, you set off on the first leg of your journey. Things go well at first. You slash through vines, traverse craggy mountain slopes, and by the next morning you’ve completed your first round of funding.?

Unfortunately, morale within the party is low. Disagreements break out about the direction of the adventure. People begin to question whether you’ll make it back alive. The barbarian is looking for other employment on his lunch break.?

It’s time to tap into one of your most useful skills as a leader — charisma.?

“As a DM [Dungeon Master] — especially if you're DMing [for] 12 year olds — you’ve got to work really hard to keep their attention and kind of read the room,” says Cocks. “That's a powerful aspect of leadership —?being an attentive leader and always having a portion of your mind focused on the table around you and on a common goal.”?

There’s a reason charisma is one of the five main ability scores at the top of your character sheet. It’s an essential skill for leading a team, keeping them focused, energized, and excited about the future of your business.?

Be ready for anything

SNAP! THWIP! TWANG!

Your ranger wasn’t paying attention and stepped on a hidden trap. Before you know it, half your party is strung up in tangled nets, a noxious mist is filling the immediate area, and the prototype for your killer app is riddled with bugs.?

The entrepreneurial journey is full of unforeseen and unexpected challenges. You’ve got to stay agile and ready to pivot at a moment’s notice. But, as Chris Cocks says, solutions aren’t always obvious in gaming or in life.

“The problems usually are really ambiguous. And figuring out what the problem is is actually a big part of the problem,” Cocks says. “D&D really helps with that unstructured problem solving and that creative thinking. It leads to these unexpected outcomes and probably some of the biggest laughs of the night.”

Just remember to stay on your toes, and before long, you’ll all be laughing about this minor hiccup on your path to success.

Disagree and commit

Finally, the entrance to the dungeon stands before you. You’ve come a long way, but the hardest part of your entrepreneurial journey still awaits. Soon, you’ll be braving the scariest terrain of all: the open marketplace.

Before you charge headlong into the fray —?sword in one hand, sound business plan in the other — you have one last huddle with your team. You discuss your options, your plans of attack, and the benefits and risks associated with each person’s idea. But in the end, you can only choose one path.

Seasoned players like Chris and Reid know that, regardless of how many plans get thrown out in the pitch phase, there’s one cardinal rule of D&D and business —?”Don’t split the party.”

“Or in modern parlance — disagree and commit,” Cocks says. “There's nothing more powerful in business than having unity in terms of action. Having really strong dialogue and even disagreement about what you do ultimately leads to conviction about what the right approach is, and then how you execute that conviction.”

Your party commits, and you charge ahead. The ensuing days, weeks, and months are filled with hard-fought victories, costly failures, and plenty of laughs along the way.?

Everyone is on a hero’s journey

You push the last boulder out of the way and shield your eyes from the glaring sunlight. You emerge from the dungeon, beaten and battered but still standing, and ready to report back to your shareholders with good news. You did it! Mission complete!

As your journey draws to a close, you look around at your party members and see that they too are glowing with pride. Not only did you defeat the monster, secure the treasure, and successfully scale your enterprise, you also learned the most valuable business lesson of D&D.

“We are all heroes in this journey, right?” says Reid Hoffman, thinking back on his time playing D&D and his storied career as an entrepreneur. “We're heroes collaborating, working together. [We should always ask,] How do we have a collaborative heroship, a mission, a goal?”

Bask in your glory or prepare for the next adventure ahead. The choice is yours. And if you’ve never played Dungeons & Dragons before, it might be time to start. You just might discover your next great business idea — and some trusted co-founders — along the way.?

Watch the full interview between Reid and Hasbro CEO Chris Cocks on YouTube, or listen on Apple Podcasts, Spotify, or wherever you get your podcasts.?