Companies mistakenly bundle management with authority, forcing top performers onto a management track to gain influence. Separate them. Define management's role as coordination and context-sharing, allowing senior individual contributors to drive decisions without managing people.

In large organizations, messages get distorted as they cascade down ('the telephone game'). Leaders must personally own and repeat the core story, not delegate it. This ensures clarity, prevents 'message packet loss,' and forces simplification of the strategy.

A successful reorg simplifies work, but delayering often does the opposite. Pushing management, QA, and coordination tasks onto developers dramatically increases their cognitive load, harming their primary function and leading to burnout. This is a key failure metric for any flattening initiative.

Removing middle management doesn't speed up decisions; it slows them down. Senior leaders become overwhelmed with the volume of tactical requests they previously delegated, causing 'decision latency' across the entire organization as they become a bottleneck.

As leaders rise, direct reports are less likely to provide challenging feedback, creating an executive bubble. To get unfiltered information, leaders should schedule regular one-on-ones with employees several levels down the org chart with the express purpose of listening, not dictating.

Feedback often gets 'massaged' and politicized as it travels up the chain of command. Effective leaders must create direct, unfiltered channels to hear from customers and front-line employees, ensuring raw data isn't sanitized before it reaches them.

In his review of thousands of org charts, serial acquirer Brad Jacobs flags managers with only one direct report as a key indicator of organizational bloat. He calls this "companionship" rather than management, highlighting it as an inefficient layer that slows communication, adds cost, and ultimately harms shareholder value.

When companies approach delayering as a cost-cutting measure driven by spreadsheets and salaries—without considering the capabilities being lost—they are committing 'organizational vandalism.' This approach ignores the complex web of interactions and processes that middle management supports, leading to systemic failure.

Companies like Amazon and Meta that cut middle management are not necessarily wrong to flatten their organization, but they err by doing so without first redesigning the underlying system. The true mistake is removing the people responsible for coordination and decision-making without fixing the processes they managed, leading to chaos.