by ttul | 2026-01-08 23:23:15+00:00
Lots of great replies - thank you, everyone.

I think most of these objections are valid against a “ChatGPT-in-a-box is your manager” framing. That’s not what I meant by “AI replaces middle management”.

What I did mean is: within ~36 months, a large chunk of the coordination + information-routing + prioritization plumbing that currently consumes a lot of EM/PM time gets automated, so orgs can run materially flatter.

A few specifics to the questions:

“Where does the AI get the information?”

Not from vibes. From the same places managers already get it, but with fewer blind spots and better recall: issue trackers, PRs, incident timelines, on-call load, review latency, meeting notes, customer tickets, delivery metrics, lightweight check-ins. The “AI manager” is really a system with tools + permissions + audit logs, not a standalone LLM.

“How does it notice burnout / team health?”

Two parts: (1) observable signals (sustained after-hours activity, chronic context switching, on-call spikes, growing review queues, missed 1:1s, reduced throughput variance), and (2) explicit human input (quick pulse check-ins, opt-in journaling, “I’m overloaded” flags). Humans are still in the loop for the “I’m not okay” stuff. The AI just catches it earlier and more consistently than a busy manager with 8 directs and 30 Slack threads.

“Who sets objectives / what about conflicting goals?”

Exactly: humans. Strategy is still human-owned. But translating “increase reliability without killing roadmap” into day-to-day sequencing, tradeoff visibility, and risk accounting is where software can help a lot. Think: continuous, explainable prioritization that shows its work (“we’re pushing this because it reduces SEV risk by X and unblocks Y; here are the assumptions”).

“What about historic experience?”

You don’t “download” a manager’s career. You encode the org’s policies, past decisions, and constraints into an accessible memory: postmortems, decision records, architecture notes, norms. The AI won’t have wisdom-by-osmosis, but it will have perfect retrieval of “what happened last time we tried this” and it won’t forget the quiet lessons buried in docs.

“Will we reinvent office politics / will people game it?”

We already do. The difference is: an AI system can be designed to be harder to game because inputs can be cross-validated (tickets vs PRs vs customer impact vs peer feedback) and the rules can be transparent and audited. Also: if you try to game an AI that logs its reasoning, you leave a paper trail. That alone changes incentives.

“Relationships and trust can’t be automated.”

Agree. And that’s why I don’t think “management disappears.” I think it unbundles the human part (trust, coaching, hard conversations, hiring/firing accountability, culture) - that part stays human.

The mechanical part (status synthesis, dependency chasing, agenda generation, follow-up enforcement, draft feedback, metric hygiene, “what should we do next and why”) becomes mostly automated. But did everyone love that part anyway? I don't.

So the likely outcome isn’t “everyone reports to an API”. It’s: fewer layers, more player-coaches, and AI doing the boring middle-management work that currently eats the calendar.

In other words: I’m not claiming AI becomes the perfect human manager. I’m claiming it makes the org need less middle management by automating the parts that are fundamentally information processing.