Jack Dorsey and Sequoia’s Roelof Botha just published a very interesting article on organisational design. “From Hierarchy to Intelligence” traces a line from Roman legions through Prussian staff officers to the modern org chart, and arrives at a striking thesis: middle management exists to route information, AI now routes information better, so middle management can be replaced.

The historical sweep is genuinely compelling. And on the coordination question, I think they’re right. But the essay treats coordination as the whole of what middle management does — and that’s where I part company.

Focus On: What the Middle Actually Does

The essay’s practical application is already visible. Block cut 40% of its workforce in February, restructured around three roles (individual contributors, DRIs, player-coaches), and eliminated permanent middle management entirely. The stock rose 24%. Wall Street loved it.

The “world model” concept — a continuously updated operational picture that replaces the context a manager used to carry — is a real contribution to how we think about coordination at scale. Where I think the argument overreaches is in treating coordination as the entirety of the middle-management function. It’s one of three jobs. It’s the most visible, the most tedious, and — yes — the most automatable. AI can track what’s blocked, who’s building what, where resources sit. Conceded.

The second job is judgment apprenticeship. Middle management is where future executives learn to make decisions with incomplete information, negotiate competing priorities across functions, and recover from being wrong. Northeastern University researcher Ravi Kalluri calls what happens when you automate these moments away the “Judgment Gap Crisis” — algorithmic management creates checkers, not leaders. When Amazon’s warehouse algorithms set quotas that managers can’t override, those managers stop practising the very skills that would qualify them for senior roles. The system improves. The human plateaus.

The third job is ethical safeguarding. An IMD analysis published the same week as Dorsey’s essay described what happens when the judgment layer becomes a rubber stamp: Cigna’s medical directors, employed specifically to review insurance claim denials, signed off on algorithmic decisions in batches — one physician denied over 60,000 claims in a single month, spending 1.2 seconds per case. That’s not management failure. That’s management elimination disguised as management.

The Double Squeeze

Even granting the full coordination thesis, there’s a question the essay doesn’t engage: who leads these companies in 2035?

The pipeline is collapsing from both ends simultaneously. On one side, companies are eliminating the middle-management roles that historically served as the training ground for executives. Gartner predicts that by the end of this year, organisations using AI to flatten their structures will have removed roughly half of their middle-management positions. On the other side, the generation entering the workforce doesn’t want the roles that remain. Only 6% of Gen Z workers say their primary career goal is reaching a leadership position. Seventy percent dismiss middle management as high-stress, low-reward. DDI’s Global Leadership Forecast reports that 77% of CHROs already lack confidence in their leadership bench strength — and that was before the current wave of AI-driven restructuring.

This isn’t a distant concern. It is a compounding structural deficit.

The Flatter Middle, Not the Empty Middle

I don’t think Dorsey is wrong that the middle will get flatter. It will. The status-meeting chairs, the slide-deck consolidators, the human routers of weekly updates — those roles are already gone in well-run organisations, with or without AI. The question is what you build in the space that remains.

My argument: the surviving middle layer must be deliberately reconstructed as a leadership forge. Not fewer managers doing the same job. Fewer managers doing a fundamentally different one — training judgment, connecting functions, providing the ethical override that no world model can supply. Dorsey’s own “player-coach” concept is one of the most promising ideas in the essay — but it needs a structure around it to fulfil its potential. A player-coach without a deliberate leadership development architecture risks becoming a senior IC who mentors on the side. Put that same player-coach inside a system designed to produce the next generation of executives as a primary output, and you have something genuinely different.

Companies that eliminate the middle wholesale will save on headcount for three years and face a succession crisis in seven. Those that redesign it — compressing layers while intensifying the developmental density of the roles that remain — will have a structural advantage that compounds as aggressively as any AI model.

The real test of any AI-flattened structure isn’t whether it ships faster this year. It’s whether, in 2035, anyone inside it will have practised leading long enough to run the company. The centurion wasn’t just routing information to the legate. He was turning raw recruits into commanders. Remove the centurion and you get a more efficient army — until you need a new general.

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Disclaimer: The views and opinions expressed in Chronicles of Change and on my social media accounts are my own and do not necessarily reflect the official policy or position of S&P Global.