Think Bigger in Planning

Ask 'what would you do with 20% more time or double the team?' to surface ambitious ideas

Eeke de Milliano
How to foster innovation and big thinking

Think Bigger in Planning

"At the bottom of every team charter we have a section called, Think Bigger. 'With 20% more time, what would you do that isn't on this list already?' ... The other question was, 'Look, if you doubled the team today, what would you do?' I think it really helps people kind of break out of this... I think you end up planning towards the team that you have and not the team that you should have." - Eeke de Milliano

What It Is

Think Bigger in Planning is a technique for surfacing innovative ideas that teams wouldn't normally include in their roadmaps. By embedding hypothetical resource questions directly into planning documents, you create permission and structure for people to articulate ambitious ideas that go beyond their current constraints.

The key insight is that teams naturally plan toward the resources they have, not the resources they should have. This constraint-based thinking filters out potentially transformative ideas before they're ever articulated. By explicitly asking what teams would do with more resources, you capture these ideas for future consideration.

How It Works

Add to Every Team Charter/Plan: At the bottom of team planning documents, include a "Think Bigger" section with prompts:

  1. The 20% Question: "With 20% more time, what would you do that isn't on this list already?"

  2. The Double Question: "If you doubled the team today, what would you do?"

Why It Works:

  • Gives explicit permission to think beyond current constraints
  • Captures ideas that would otherwise be self-censored
  • Creates a pipeline of future initiatives
  • Helps leadership understand where teams would invest if given resources
  • Low friction—doesn't require separate meetings or processes

Format Guidelines:

  • Let people express ideas however they want (bullets, demos, half-formed thoughts)
  • Less structure is better—don't pigeonhole creativity
  • Review these sections during resource allocation discussions

How to Apply It

  1. Add the section to your planning template - Include "Think Bigger" as a required section at the bottom of team charters and quarterly plans

  2. Make it genuinely optional - Don't force detailed plans; accept rough ideas

  3. Review during allocation - When you have resources to allocate, check these sections first

  4. Fund occasionally - Sometimes just say "take an engineer and go do it" to validate the practice

  5. Track what gets done - Like the Crazy Ideas doc, review what actually shipped from these sections

When to Use It

  • During quarterly or annual planning cycles
  • When setting up team charters for new teams
  • When you sense teams are thinking too incrementally
  • When allocating additional resources to teams
  • When planning sessions feel constrained or uninspired

Source

  • Guest: Eeke de Milliano
  • Episode: "How to foster innovation and big thinking"
  • Key Discussion: (00:25:09) - Think Bigger section in team charters
  • YouTube: Watch on YouTube

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