Crazy Ideas Doc

Annual company-wide solicitation of high-risk, high-reward ideas

Eeke de Milliano
How to foster innovation and big thinking

Crazy Ideas Doc

"At the beginning of every year, David will send out a blank doc to the org and it's titled Crazy Ideas. And the prompt is, 'Crazy ideas are ideas that we shouldn't, obviously, do. There's a 90% chance that they make no sense. But in the 10% chance that they do, they will make a 10x to 100x difference for the business.'" - Eeke de Milliano

What It Is

The Crazy Ideas Doc is an annual tradition where leadership sends a blank document to the entire organization requesting ideas that have a 90% chance of being wrong but would create 10-100x impact if they work. Unlike hackathons that often produce ideas that go nowhere, this practice is explicitly tracked and reviewed year-over-year.

The format originated at Stripe and was adopted at Retool. The key insight is that giving people explicit permission to think big—with the understanding that most ideas won't work—unlocks creativity that normal planning processes suppress.

How It Works

  1. The Prompt: At the beginning of each year, send a blank doc to the organization with this framing:

    • "Crazy ideas are ideas we shouldn't, obviously, do"
    • "There's a 90% chance they make no sense"
    • "But in the 10% chance they do, they will make a 10x to 100x difference"

  2. The Request: Ask for crazy ideas from everyone—not just product ideas but organizational ideas, marketing ideas, anything

  3. The Follow-Up: At the start of each new year, review the previous year's doc and identify what actually got done

  4. The Tracking: Typically 3-8 ideas from the list get implemented each year

How to Apply It

  1. Create the ritual - Schedule the doc to go out at a consistent time each year (beginning of year works well)

  2. Make it leadership-sponsored - Have the CEO or a senior leader send the doc to signal importance

  3. Keep it low-friction - Accept any format: bullets, full demos, half-formed thoughts

  4. Review and act - Close the loop by showing what got implemented; this validates the practice

  5. Use it for morale - When you have a down day, scroll through the doc for energy and inspiration

When to Use It

  • When teams are stuck in incremental thinking mode
  • When you want to capture innovation energy across the entire organization
  • When hackathons aren't producing lasting impact
  • When you need to surface ideas that wouldn't make it through normal planning

Source

  • Guest: Eeke de Milliano
  • Episode: "How to foster innovation and big thinking"
  • Key Discussion: (00:25:21) - Introduction of Crazy Ideas tradition
  • YouTube: Watch on YouTube

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