Essay
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City Planning

City Blocks and the Flow of Information Through Organizations

Urban planning principles applied to how organisations route information — and what most get wrong.

The Grid Problem

Most cities evolved organically — narrow streets, irregular blocks, paths that follow geography rather than geometry. But when cities are planned from scratch, designers face a fundamental question: how do you structure space so people can move efficiently without creating bottlenecks?

Organizations face the same problem with information instead of people. And they make the same mistakes.

What Urban Planners Learned

1. Hierarchy matters, but only to a point

Cities need major arterials and minor streets. Information highways and side channels. The mistake is thinking more hierarchy means more efficiency.

Too much hierarchy creates the same problem as a city with one main road — everything funnels through a bottleneck. Urban planners learned this in the 1960s when highway-centric design created traffic nightmares. Organizations are still making the mistake with approval chains and information gatekeepers.

2. Redundancy enables resilience

Grid systems work because there are multiple paths between any two points. If one street is blocked, traffic reroutes.

Organizations that route all information through single channels — the manager who must approve everything, the meeting that everyone must attend — create fragility. When that channel fails (and it will), everything stops.

3. Mixed-use beats zoning

Cities that segregate functions — residential here, commercial there, industrial over there — require people to travel long distances for basic needs. Cities that mix uses reduce unnecessary movement.

Organizations do this with departmental silos. Marketing sits on floor 3, Engineering on floor 5, Sales in a different building. Then we wonder why cross-functional collaboration is hard. The structure makes it expensive.

The Information Routing Problem

When I map how information flows in most organizations, I see the same patterns that urban planners identify in poorly designed cities:

Congested intersections: All decisions funnel through a single approver or meeting

Dead ends: Teams that produce work no one downstream uses, but everyone's too polite to say it

Long commutes: Information traveling through three departments to reach someone two desks away

Gated communities: Teams that hoard information because sharing requires navigating bureaucracy

What Good Routing Looks Like

The best-designed cities — Barcelona's Eixample, Copenhagen's bike infrastructure, Tokyo's mixed-use density — share common principles:

  1. Clear primary paths, flexible secondary routes: Major decisions have defined processes, but day-to-day work flows through lightweight channels
  2. Local autonomy within global structure: Teams can make decisions without escalation, but within clear boundaries
  3. Visibility without surveillance: Information is accessible without forcing everyone to consume everything

Organizations that apply these principles look different:

  • Decisions are pushed to the edge, not the center
  • Information is published in shared spaces, not gatekept in inboxes
  • Approvals are exceptions, not defaults

The Uncomfortable Question

If you drew a map of how information moves through your organization — who talks to whom, who approves what, where decisions get made — would it look like a well-planned city or a medieval town that grew by accident?

Most organizations are medieval towns with skyscrapers awkwardly inserted. Functional, but inefficient. The structure made sense when the organization was 20 people. At 200, it's showing cracks.

Urban planners figured this out decades ago. Organizations are still learning.

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