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Real Leadership for Real Humans

Roll for Insight blends real-world leadership theory with the group dynamics of roleplaying games to help managers and team leads get results without burning out or burning bridges.

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Built on Real-World Experience

Roll for Insight didn’t come from a boardroom brainstorm session. It was hammered together in warehouses that smelled like diesel, bike shops where nobody ever scheduled a lunch break, and training rooms full of people who’d rather be anywhere else.

This is leadership forged under fluorescent lights and held together with caffeine, sarcasm, and trial by fire. It draws from group dynamics at the gaming table and management theory from actual research—not just what sounds inspirational on a coffee mug.

The result? A leadership system that works on real people. Even the ones who seem like glitchy NPCs. 

Our services

Leadership Training for the Real World (and the Gaming Table)

Leadership Workshop

Learn how to lead real people without turning into a cartoon villain. 

A live, in-person workshop that trains new leaders how to handle conflict, earn trust, communicate clearly, and get results--even if nobody gave you a manual. Built for frontline managers, leaders of small teams, and anyone who woke up one day and found themselves in charge.

GM Workshop

Run better games by becoming a better leader.

A training session for Game Masters who want to level up their group management skills. Learn how to manage different player types, keep a campaign on track, and avoid full-party meltdowns--all using real leadership principles that apply at the table and beyond.

Team-Building Adventures

A one-shot RPG experience for teams that learn by doing.

Build trust, sharpen communication, and practice decision-making in a totally unexpected way: by adventuring together in a custom fantasy world. Perfect for teams who are tired of awkward icebreakers and want something more collaborative, more memorable, and a lot more fun.

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A Real Leadership Book for the Humans in the Room

 

This upcoming book explores what happens when you take academic leadership theory and test it in the wild—specifically, at the head of a D&D table full of unpredictable players. It’s a practical, irreverent guide for anyone trying to lead real people.

Think of it as the missing link between management textbooks and the GM’s chair, where communication, motivation, and problem-solving are never theoretical.

 

Learn More
Sometimes It’s a Metaphor, Sometimes It’s Tuesday

When You’re in Charge and It’s Already On Fire

The Roll for Insight blog delivers real-world leadership lessons from behind the GM screen and the supervisor desk. It’s where tabletop chaos meets frontline management—full of stories, strategies, and things that didn’t go according to plan (but still taught something worth knowing).

 

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Standing Out Isn’t the Problem. Leading Is.

Built by Someone Who's Been There and Led That

 

The philosophy behind Roll for Insight

This isn’t a theory lab or a buzzword farm. It’s a leadership philosophy forged from long hours, bad bosses, impossible teams, and the table where I ran my first game of D&D. Everything here connects academic leadership principles to real-world chaos—whether that chaos comes with spreadsheets or spell slots. If you’ve ever felt unprepared, outnumbered, or just plain tired of pretending you have all the answers, you’re in the right place.


 

See the Difference

This isn’t about handing you a script. It’s about helping you develop the clarity, empathy, and leadership instincts to adapt to any team—and any situation.

Ready to Stop Rolling with Disadvantage on Your Leadership Checks?

Leadership doesn’t come with a rulebook—but it does come with people who need you at your best. Roll for Insight helps you build the clarity, empathy, and adaptability to lead any team, in any situation.
 
 
 
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