Jack Dorsey, a rich man who many mistake for a smart man, wants to use A.I. to help eliminate middle management. According to this article:

Jack Dorsey wants all 6,000 Block employees to report directly to him — with zero management layers — using AI to replace the coordination and oversight work that middle managers have historically done.

Block already cut 4,000 jobs — nearly half its workforce — in February 2026, shrinking the company from roughly 10,000 to 6,000 employees. Dorsey says most other companies will follow the same path within a year.

Wow. Sounds impressive. You can read the article to see how he plans to do it, but it sounds like a bunch of hand waving to me, amounting to not much of anything.

People have been talking about how computers would eliminate middle management since the 1950s. Indeed, as you can see in this PC Mag piece from 1984, the belief that middle management could be eliminated resurfaced with the surge of personal computers coming to organizations. And yet organizations, including IT organizations, continue to have multiple layers of management despite the omnipresence of personal computers.

So no, I don’t believe AI will allow Jack Dorsey or any CEO to eliminate middle management completely, any more than AI will eliminate bullshit jobs. It didn’t happen in the 1980s and it won’t happen in the 2020s.

P.S. I think Dorsey used AI — AI washing — to cover for the bad management decisions that led up to the 4000 job cuts. The Guardian mentions: ‘overstuffed teams outside of the “bitcoin hardware team” and the company’s “bloated headcount era”, which began in 2020, fueled by nearly nonexistent interest rates in the US’. Dorsey denied this, but I’m inclined to believe Jason Karsh who used to work there. Dorsey has a talent for being in the right place at the right time and spouting ideas that make him look like a leader, but both his decisions at Block and his poor leadership at Twitter makes me say one should never look to him for ideas on how to run an organization.