Leadership & The Future of Work Will AI Replace Your Manager? What Block's Radical Restructure Is Really Telling Us

By KK Harris

March 31 2026

I know some of you will read this and think it has nothing to do with you — and that's okay. For those paying attention to what's happening right now in the world of work, please keep reading.

Things are getting very serious in the world of work.

I was recently at a networking event talking with a sharp professional who told me her boss fully agrees her next move is into people management. I smiled, encouraged her, and kept it moving, however something wasn’t sitting with me. But after reading a particular article, I had remembered why and I sent her that article about what Block was doing that has the potential to be a game changer in the middle management layer.

Who Is Block — and Why Should You Care?

Block is the company behind Square, Cash App, and Afterpay. Founded by Jack Dorsey — the co-founder of Twitter — it is one of the most prominent fintech companies in the world, processing payments for millions of businesses and consumers every single day. When Jack Dorsey speaks, the business world listens. And what he just said should have every professional in middle management paying very close attention.

"Within the next year, I believe the majority of companies will reach the same conclusion and make similar structural changes."
— Jack Dorsey

The Essay That Changed the Conversation

Dorsey co-authored an essay with Sequoia Capital's Roelof Botha titled "From Hierarchy to Intelligence." The argument is both simple and seismic: the traditional management structure — the org chart that generations of professionals have built entire careers inside of — is a 2,000-year-old relic that AI is now making obsolete.

According to Dorsey and Botha, corporate hierarchy was never really a management philosophy. It was an information routing system — borrowed from the Roman Army, refined by Prussian military reformers, and imported into American business in the 1840s. And honestly? That last part was news to me. It existed because humans can only effectively manage a limited number of people at one time. That constraint, they argue, no longer applies when AI can handle the coordination work that middle managers have always done.

This is not a think piece. It’s a blueprint — and it arrived weeks after Dorsey cut 40% of Block's workforce, more than 4,000 people, while the company was profitable and growing.

Middle Management Jobs at Risk: What the New Model Looks Like

At Block, the traditional management layer is being replaced with 3 roles: 1. Individual contributors who own deep technical work, 2. Directly Responsible Individuals (DRIs) who own specific outcomes for defined periods, and what Dorsey calls 3. player-coaches — people who can build and develop others simultaneously. There is no permanent middle management layer. The future of middle management, at least at Block, is not a promotion. It is an elimination.

The market rewarded this decision immediately. Block's stock rose nearly 25% on the announcement. Morgan Stanley upgraded the company. Goldman Sachs raised their price target. Wall Street is not just watching — it is applauding.

And Dorsey made clear he does not believe Block is alone in this conclusion. In other words, he’s just saying what others aren’t.

Is This the Blueprint for Every Workplace?

That is exactly the right question. Other companies are already moving in the same direction, just at different speeds. Meta is concentrating talent among elite AI roles while flattening everything else. Salesforce is reframing AI as workforce augmentation rather than replacement — for now. Amazon has spoken openly about needing fewer layers as AI evolves.

The future of middle management is not being debated in boardrooms as a distant possibility. It is being decided right now.

As an executive coach, I genuinely hope this is not happening where you work. But it could. And I would rather you hear it from me. If you are able to take this information you can use it as a strategic advantage. It’s what I talk about in my RECLAIM framework. When we know whats going on, not only inside of the business we work for, but in the macro, then we can become strategic in positioning ourselves.

What I Would Do Today If I Felt My Role Was at Risk

Four Pivots Worth Making Right Now

01

Stop managing and start building. If your entire value sits in coordinating people and running meetings, that function is exactly what AI is being designed to absorb. Pick up a skill. Own an outcome. Get your hands back in the work.

02

Get AI-fluent — not familiar, fluent. Block now tracks daily AI usage in employee performance reviews. I hope your company handles this transition with far more grace. But the expectation is coming, and you want to be ahead of it, not scrambling to catch up.

03

Become a player-coach before someone decides you don't need to be in the room. The new model rewards people who can execute deeply and develop others at the same time. Be both — intentionally.

04

Do not wait for the company announcement to start preparing. By the time a restructure is announced, you’re already too late. Your pivot needs to happen now, quietly, and on your own terms.

The 2030 workforce displacement predictions are no longer a distant warning sitting in a research report somewhere. They are walking into the building.

The question is not whether AI will reshape middle management. Based on what Block has just shown us, the question is whether you will be ready when it reaches your industry, your company, and your floor.

What are you doing right now to make yourself irreplaceable?

If this resonated with someone in your network who needs to read it — please share it with them. Sometimes the most caring thing we can do is pass along the information people haven't found yet.