About CEO Hats
The Thinking Behind the Toys
The Unscrapable Insight
"Warm-up exercises for strategy workshops are often fun but add little to the thinking. CEO Hats is a fun and safe way to explore what participants would do if they ran the company—through the lens of notable CEOs whose styles they can apply to their thinking."
The Joy of Roleplaying
Brainstorming is hard. When people are asked to solve complex business model challenges, they often default to safe, conventional ideas. However, when we give someone a "hat" (a new identity), we bypass their internal editor.
By adopting the persona of a celebrity business leader like Steve Jobs or Yvon Chouinard, participants are granted permission to be ruthlessly simple, purpose-driven, or radically candid without personal risk.
Keep the Friction Tactile
While the card deck is digital, the collaboration is physical. CEO Hats intentionally avoids capturing ideas inside the application.
Instead, we force teams to communicate, debate, and document their thoughts on physical Post-it notes. This keeps people looking at each other—not down at screens—and keeps the workshop high-energy and conversational.
The Blended Provocation Formula
Each card display utilizes a strict 1+2 provocation structure to keep thinking focused and prevent cognitive overload:
A core question regarding client/customer experience or internal organization structure that appears on every single card. This anchors the strategic baseline.
Hyper-focused questions based on the specific CEO's unique style (e.g. Canva's Melanie Perkins regarding removing approval gatekeepers, or Reed Hastings on the "Keeper Test").