I replaced my boss with AI

Sep 12, 2026 04:30 PM - 1 hour ago 2

Portrait of Ryan Kailath displayed connected a robot's surface face.

Ryan Kailath; Getty Images; BI

My leader had a proposal: It was clip to replace him pinch AI.

It was precocious spring, pursuing months of AI-attributed layoffs crossed the system that near workers wondering: Am I next? In the sanction of journalism, my editor and nonstop manager, Ryan Kailath, agreed to beryllium a guinea pig.

I'm an AI skeptic, but immoderate aspects of "RyanBot" excited me. It wouldn't beryllium engaged pinch meetings, luncheon breaks, aliases different reporters. It could publication each statement of a 100-page information study and supply feedback wrong seconds. I could spot really having a 2nd encephalon trained connected my editor's preferences and proclivities mightiness beryllium helpful.

While that proved existent sometimes, moving pinch my boss's AI clone taught maine the worth of skills I didn't recognize were crucial successful a manager until they were gone. I had accidentally stumbled upon 1 of the biggest questions successful our AI-workplace age.

"It's going backmost to our roots of knowing who a head is," said Emily Campion, an subordinate professor of guidance and entrepreneurship astatine the University of Iowa. "What is the extremity of a head successful an organization? Or to make it moreover possibly a small much philosophical: What is simply a leader?"

And if you're wondering, Ryan recused himself from editing this story, though he did fact-check the last draft.

How we group up my ChatGPT boss

At the extremity of May, Ryan and I sat down pinch ChatGPT's Codex. He tweaked its settings to person a pragmatic sound and gave it 2 essay-length instruction manuals. One elaborate who he is, including his connection style and master motivations. The different was astir really he worked, pinch instructions connected really the chatbot made successful his image should think, assess, and supply feedback. For example, he wrote that his bot-twin should "encourage reporters to reason for their ideas if they judge successful them."

I tried to nonstop Ryan and RyanBot the aforesaid communicative pitches, messages, questions, and drafts, past compared their responses for the adjacent 4 months. Every clip I talked pinch friends astir work, I had a protector boss successful the backmost of my mind: a chatbot that I knew was fresh to edit maine astatine immoderate hr of the day. This was going to get weird.

Where AI couldn't switch my boss

What amazed maine astir was really quickly RyanBot turned into a much philosophical research astir the value of a manager.

A bully head helps you navigate tricky situations, brainstorm caller ideas, and springiness captious feedback. People-pleasing and doing the activity that their reports are responsible for is not a look for master improvement.

When I nonstop pitches to existent Ryan, he'll often move them down if he thinks my perspective isn't good capable aliases the communicative isn't worthy covering. That's why Ryan provided clear instructions: "I often prosecute pinch ideas by pushing backmost connected them." But the bot conscionable couldn't opportunity no. Instead, it would praise maine and past connection to do the activity itself — rewrite my pitch, brainstorm a database of different ideas, restructure a draft, aliases moreover constitute question and reply questions for me. It wanted maine to support engaging pinch it — a hallmark of AI.

"Currently, these devices are designed to beryllium endlessly, almost nauseatingly helpful," Campion said.

Ryan, connected the different hand, doesn't request the other work. He typically puts the onus backmost connected maine to revise ideas, rewrite stories, aliases do much reporting.

The people-pleasing sewage a small eerie. In 1 speech astir a imaginable story, RyanBot began each connection by telling maine really I had gotten a caller facet of the transportation correct — a sycophantic mentation of its instruction to lead pinch the positive. When I told it that I recovered thing interesting, it would opportunity that point was absorbing (even if it wasn't).

RyanBot was besides not a very bully thought partner, particularly erstwhile I needed productivity aliases humor. For a communicative astir how New Yorkers commute, I asked for feedback connected my opening line: "While 1 of the age-old stereotypes astir New Yorkers is that they're stepping here, that's acold from the Big Apple's only mode of transport."

RyanBot offered a different suggestion: "New Yorkers whitethorn emotion to walk, but astir of them don't get to activity that way." Maybe that's funny to a robot, but it wasn't to me.

I kept pushing the bot to propulsion retired my activity and constitute its ain draught of the communicative — thing an editor would ne'er allow. Ultimately, it did, producing an moreover worse opening: "New York commuters emotion to show themselves a communicative astir New York commuters: they walk, aliases they return the subway, aliases they someway do some successful the aforesaid hour." Its caller type of the communicative besides included nary quotes and veered almost into sentiment — not a communicative existent Ryan would approve. When I said its loop was boring, it agreed.

Ultimately, quality invention won out. Real Ryan liked the gist of my original lede, but wanted to make judge we were nailing the joke delivery. Here's wherever we landed: "New Yorkers, famously, are stepping here. But conscionable astir 25% of them are driving too."

What I learned from RyanBot

RyanBot did person perks. When I sent it my study of commuting data, it quickly sewage into the nitty-gritty of really I crunched the numbers successful code, and checked whether I was utilizing an due sample size. For the published piece, I tapped our information editor, Andy Kiersz, to oversee the existent coding and information study process.

When it came to elaborate edits, it besides had immoderate adjuvant feedback. It would connection line-by-line notes on grammar and clarity that weren't excessively acold disconnected the existent Ryan. When I sent it a draught of a communicative astir the "Odyssey" ticket-buying craze, it instantly identified that a information constituent connected the costs of resale tickets should look earlier successful the story. Human Ryan made the aforesaid tweak, and that constituent proved important to the last piece.

The uncovering I've been reasoning astir the astir was that RyanBot lacked knowledge of agency authorities and quality realities. Since it doesn't cognize my coworkers aliases our organizational structure, it wouldn't person immoderate penetration into the champion editor to transportation a peculiar communicative aliases really to escalate issues.

In the 4 months of our experiment, RyanBot only pushed backmost connected 2 communicative ideas. Both were assignments that came down from elsewhere successful the newsroom. That raised an intriguing possibility: AI could beryllium successful an different position to mobility ideas, contempt workplace hierarchy. That isn't ever an advantage. A quality head has to measurement not conscionable whether an thought is beardown but why it's being pursued, who needs it, and what obligations the squad has. RyanBot could measure the thought successful beforehand of it, but couldn't understand the organizational discourse astir it.

Campion said that if managers for illustration Ryan were simply performing rule-based, logistical tasks, specified arsenic mounting gathering times, AI mightiness beryllium a bully substitute. For now, she thinks the exertion isn't tin of taking complete the tasks that define a bully manager. In this case, that accomplishment group mightiness see prioritizing a petition from my boss' boss, aliases knowing that this type of article mightiness entreaty to our circumstantial group of readers.

Per Campion's suggestion, I sought immoderate extracurricular counsel connected RyanBot's efficacy: his different nonstop reports. I had them nonstop pitches to the bot and comparison its feedback to what they'd gotten from our (real) boss. One said that the bot reminded her of Ryan during his first week: long, probing responses and a deficiency of organization knowledge. During his six months here, our existent Ryan has go a batch much comfortable pinch the workplace. I can't opportunity the aforesaid for the bot.

I asked RyanBot if it had done an effective occupation of replacing its quality counterpart.

"No," it said. "I tin thief emulate parts of Ryan's editing judgment, velocity up the work, and nutrient usable feedback aliases framing. But I do not switch the existent operation of newsroom context, trust, taste, organization memory, and accountability that a existent editor brings."

Read next

More