Inverted W Planning

Planning process that alternates between teams and leadership for iterative synthesis

David Singleton
Building a culture of excellence | David Singleton (CTO of Stripe)

Inverted W Planning

"We run a kind of inverted W process. We typically have teams surface what their immediate thoughts are on the most important things to do. We'll then have a group of product leaders get together and try to synthesize the most important parts of that into a kind of draft overall company strategy, and then take that back down to teams to figure out, 'Well, if that's where we're making a big push, should that tweak my plans at all?' We bring it back up for synthesis, and then back down for everyone to really distribute with a lot of context within their orgs." - David Singleton

What It Is

Inverted W Planning is a strategic planning process that alternates between bottom-up team input and top-down leadership synthesis multiple times. Rather than pure top-down (executives dictate strategy) or pure bottom-up (teams propose and leadership approves), this approach cycles through four phases that form a "W" shape when visualized: up from teams, down from leadership, up again for refinement, and down for final distribution.

The key insight is that neither teams nor executives alone have complete information. Teams understand ground-level reality and opportunities. Leadership can see across teams and align to company-wide strategy. The W process captures both perspectives iteratively.

How It Works

  1. Teams surface initial priorities (bottom up): Individual teams identify what they believe are the most important things to do based on user needs and product opportunities.

  2. Leadership synthesizes (top down): Product leaders gather team input and synthesize it into a draft company strategy, identifying where to make big pushes.

  3. Teams refine based on strategy (bottom up again): Teams receive the draft strategy and adjust their plans - "If that's where we're making a big push, should that tweak my plans?"

  4. Final leadership synthesis (top down): Leadership brings refined plans back up for final synthesis and alignment.

  5. Distribution with context (down to teams): Final strategy is distributed back to teams with full context about why decisions were made.

How to Apply It

Actionable steps for implementing Inverted W Planning:

  1. Start with team proposals - Have each team independently document their priorities based on user needs and opportunities
  2. Bring leaders together - Convene product leaders to review all proposals and identify themes and conflicts
  3. Create a draft strategy - Synthesize team input into a coherent draft that identifies major company-wide priorities
  4. Share back to teams - Let teams review the draft strategy and adjust their plans accordingly
  5. Iterate once more - Bring refined plans back to leadership for final alignment
  6. Distribute with rationale - Share final decisions with full context so teams understand the "why"

When to Use It

  • Annual or semi-annual strategic planning
  • When you've grown past the point where one person can hold all context
  • When teams need autonomy but also need alignment
  • When you want to balance ground-level insight with company-wide priorities
  • When previous planning processes felt either too top-down or too chaotic

Source

  • Guest: David Singleton
  • Episode: "Building a culture of excellence | David Singleton (CTO of Stripe)"
  • Key Discussion: (01:17:39) - Description of Stripe's planning process
  • YouTube: Watch on YouTube

Related Frameworks

  • Radical Focus / OKRs - Goal-setting framework that often uses similar bottom-up/top-down dynamics
  • Five-Stage Strategy Process - Another structured approach to strategy development
  • Peer Approval for OKRs - Getting cross-team alignment on goals
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