Jack Dorsey just restructured Block so that all 6,000 employees report directly to him, essentially eliminating middle management.

People are losing their minds about it.

I say bravo.

And I say that as someone who spent time in middle management. I know what the job actually does — and one of the things it does, is filter.

The Filter Problem

When you join a company, you want to know where you're going. You want to hear from the person who built the thing, the one who knows why the decisions were made and what the company is actually trying to become.

The person who has everything at stake.

What you usually get is a middle manager. Someone who themselves heard it from someone, who heard it from someone, who maybe once sat in a meeting with a person who was two degrees from the founder.

I wasn't sitting there deciding to corrupt the message when I was managing people.

But you interpret things through your own lens.

You emphasize what feels urgent to you.

By the time the vision reaches someone three or four layers down, it's been translated so many times it barely resembles what started.

Your job as an employee is to execute against a direction. But if the direction you're getting is already a diluted version of what the founder actually meant — you're not executing against the vision. You're executing against an interpretation of it.

That always bothered me, even when I was the one doing it.

The Part People Push Back On

Here's the counter argument. Six thousand people cannot literally have one manager. You need someone to handle day-to-day coordination — feedback, the logistics of getting work done across teams and time zones. Not everyone can walk into the CEO's office when the shit hits the fan.

But there's a difference between needing coordination and needing interpretation layers.

Most middle management arguments conflate the two.

"Who will give people feedback?" is a real question. "Who will translate what the strategy means for your team?" is the one I'd actually want to eliminate. That second job should be unnecessary if the vision is communicated well enough in the first place.

The question isn't whether the org needs structure. It's which parts of the structure are adding signal and which ones are subtracting it.

What I Actually Wanted When I Was on the Receiving End

When I was coming up and someone had a message to deliver, what I always wanted — and rarely got — was to hear it from the person who made the decision.

Because when you hear things secondhand, you're always wondering what got left out. What the real reason was. What nuance got smoothed over to make the message more palatable.

When you hear it from the person with the actual context, you can ask questions. You can push back on the actual reasoning. You can understand the tradeoff, not just the conclusion.

That's what I think Dorsey is reaching for.

Whether it works at 6,000 people — I genuinely don't know. That's the interesting experiment. The math might not work out and he might end up building a different kind of management structure to compensate. But the instinct behind it feels right to me.

It's going to be hard for people who built their careers in middle management, and I understand that. It's not a place to stay forever, and hopefully it won't be much of a stop moving forward.

It's not comfortable to be told the role you've held is the problem.

But I think it's worth being honest about. Every layer you add between the vision and the person executing it is a place where something can go sideways. That's true even when everyone involved has the best intentions.

Especially then, actually.