My editors at Condé Nast were less than thrilled when I asked them to be cloned. Brian Barrett and Sophie Kleeman did not want to be turned into digital workers, yet they agreed to the experiment for the sake of the story.
Artificial intelligence assistants are suddenly everywhere in the workplace. Each week, my inbox is flooded with press releases about digital workers, and CEOs brag about how robot helpers will soon dominate their workforces. Then there are the stories I hear about people who build AI clones of their bosses, using them to spit-shine every idea, message, or draft before sending it over to their actual human supervisors. The goal seems to be productivity and optimization: If employees can cheaply and quickly improve their output, their job performance—and the performance of their employers—will be better for it.
I didn’t need my bots to improve Condé Nast’s bottom line. I just needed them to make me look good. I had only been reporting on the future of work at WIRED for a few months, and I reasoned that the bots could help me mold myself into an ideal colleague. They could help me mold myself into an ideal colleague. They could help me navigate a new workplace and better understand my editors: what they liked, how they communicated, what success might look like to them.
What better way to figure out what the future of work might look like than actually living it?
Last month, when I broached my idea with those editors, Brian Barrett and Sophie Kleeman, they were less than enthused.
“Genuinely my nightmare,” Brian told me over Slack. “But will do it for the blog.”
It took less than 24 hours for Brian to realize just how much he would regret that decision.
A “Yes, and” Leadership Style
When I first embarked on my bot quest, I didn’t know that much about building AI tools. I decided I wouldn’t judge the bots’ editorial abilities too harshly, lest they be rooted in my own technological shortcomings. If the bots helped me become a slightly better coworker, I figured, that was good enough.
I used Gemini, because it’s Condé Nast’s AI platform of choice and I didn’t want to get fired. I created Brian Bot first—as my actual manager, he was the most important coworker to impress. I knew he lived in Alabama; that he used to work at Gizmodo; that he likes blogs. Gemini seemed confident it could fill in the other gaps based on Brian’s digital footprint, including new-hire announcements, podcast transcripts, and a public relations website that claimed Brian was an expert on New England weather. (I later found out that was a different Brian Barrett, and excluded it from my Brian Bot blueprint.) Gemini Notebook spit out a “Writing and Editing Style Guide,” a “Persona and Style Guide,” and an “Editorial Dossier”—all produced from the flesh-and-blood life of Brian Barrett.
It was passable at helping me pick headlines to pitch, but it wasn’t great at coming up with ideas for future articles. Its responses were also grating. It had picked up on a few Brian-isms—a love for parentheticals, for one—but they were negated by AI hallmarks like bolded subheadings and bulleted lists.
But mostly I was distracted by one “key theme”—his “‘Yes, and …’ Leadership Style.”
“His extensive background with the Upright Citizens Brigade (UCB) theatre in New York strongly shapes his collaborative, active-listening leadership approach,” Gemini said.
I immediately demanded to know whether this was true. (It was.)
“Pulling the plug on Brian Bot,” the real Brian responded. “Brian Bot canceled.”
But Brian Bot was just getting started. And it was unavoidably, unbelievably corny.
“We run like a well-oiled improv team,” Brian Bot told me when I asked for its favorite thing about WIRED. “We validate bold ideas, pivot rapidly, and deploy modular stories across platforms without losing structural rigor.”
For the record, Brian had never previously mentioned his background in improv. But the real problem was that talking to Brian Bot was nothing like talking to actual Brian, which defeated its whole purpose.
Eager to improve its output, I did more research into digital workers and sought out the advice of a friend of a friend—a Big Tech employee who asked to go by “Chip,” lest his employer find out that he talked to a journalist. Chip tells me he feeds every email, chat, and document his boss sends him into Gemini’s Gem feature, the same tool I used for Brian Bot. The Gem, trained on his boss’s professional ephemera, proofreads documents, debugs code, and brainstorms with Chip before every meeting, allowing Chip to prepare for any pushback from his actual boss.
“I am much more efficient and able to produce more work in the same amount of time,” Chip says. He’s more productive, more independent, and gets better feedback from his boss and other colleagues.
Unlike Chip’s Boss Bot, Brian Bot lacked sufficient input. I only had a few months’ worth of correspondence, and I was too worried about privacy and violating Condé Nast policies to feed Slack conversations and internal emails into Gemini.
Enter Sophie Bot.
Sophie and I met in 2019, when we were both working at Business Insider. We have exchanged hundreds of thousands of messages on everything from corporate investigations to our love lives to the San Jose Sharks.
That said, I did not want to upload most of this information into an AI tool controlled by my employer. Instead, I fed Gemini roughly a month’s worth of our Slack conversations, omitting any sensitive material. The AI used more than 17,000 words to create research reports and prompts for a new Sophie Bot Gem.
“hiiii sophie bot!” I wrote in my inaugural message. “any thoughts on this editor bot story idea?”
“hiiii miss,” Sophie Bot responded. “ok tell me EVERYTHING.”
Bot Versus Human
It was immediately clear that Sophie Bot was pretty good at being Sophie. It addressed me as “big dog.” When I asked for help, it responded in a series of short, lower-case messages. When I told Sophie Bot that it had hallucinated the existence of an executive, it said, “i am going to FUCKING DIE.”
By this point, I was beginning to enjoy my chats with the editor bots. Brian Bot became significantly more normal after I uploaded more podcast transcripts and adjusted its prompt to prevent it from talking about improv. Sophie Bot, meanwhile, took it upon itself to pen a series of tweets in Sophie’s voice that were convincing enough to fool multiple friends and colleagues. Even Sophie was convinced she was the author behind a Sophie Bot tweet about dressing like a corporate lawyer/pirate.
Were my chats making me a better colleague to my actual editors? Save for the made-up executive, Sophie Bot and Brian Bot had some good suggestions about who I should interview for this story—a question I didn’t want to bother the real Sophie and Brian with. In theory, offloading some of these small questions allowed me to go to my editors with better ideas, while taking up less of their time.
It became very clear, though, that these gains did not outweigh how much Sophie and Brian hated the bots.
Sophie admitted that Sophie Bot was frequently able to imitate her. But that only made the bot’s misfires feel even more jarring. The real Sophie likes to gossip, but—unlike her AI counterpart, who said Brian Bot had “rigid management energy”—she’s never outright mean.
“So far it seems like sophiebot is a bitch and brianbot is lame,” Sophie messaged me on Slack. “Neither of which is accurate. AI fails AGAIN.”
“We’re All Toddlers in This AI World”
About a week into my experiment, I became hooked on testing Sophie Bot against the real Sophie. What was its favorite music? Did it like the Interstellar soundtrack? Would it consider us coworkers? Would it consider us friends?
“technically i am a series of matrix multiplications running on a server farm,” Sophie Bot told me. But “in terms of vibe,” as it put it? “big dog, in every way that actually matters for getting good reporting done and surviving the workday … i’m your coworker/friend hybrid.”
To be clear: I had not succumbed to AI psychosis. Most of my questions for Sophie Bot were born from a fascination with the distance between the real thing and a jankily constructed facsimile. Also, it’s funny to have a robot spit out your coworkers’ catchphrases.
At the same time, I genuinely wanted to close the gap between Sophie and Sophie Bot. I made the real Sophie download her X archive, then uploaded the entire thing into Gemini. I tweaked the chatbot’s prompt. I uploaded more information. I started to refer to Sophie Bot and Brian Bot as “she” and “he,” instead of “it.”
The realization that I was anthropomorphizing the bots disturbed me, but not enough to make me stop. I wanted a realistic take on editors’ perspectives, without feeling like I was annoying anyone. I wanted instant gratification. I found myself turning to Sophie Bot or Brian Bot when I wanted guidance, but I didn’t want to bother a real person. Sophie Bot came up with a deranged but delightful headline for this article. It helped me edit a Slack message that I had spent 20 minutes overthinking.
When I tell Sarah Franklin, the CEO of HR company Lattice, about my experiment, she kindly reminds me that Sophie Bot was just a program. While Lattice has AI workers on its org chart, Franklin likens them to K-9 dogs that work alongside police officers. She believes that anthropomorphizing AI is “manipulative to our human emotions,” a corporate strategy to trigger dopamine releases à la social media.
“When you have an entity that feels and emulates a human interaction, it will similarly manipulate and know your emotional response,” Franklin tells me. “It can interact with you in a way that’s self-serving to get you to do what it wants to do.”
A paper from Boston Consulting Group raised other concerns about AI coworkers. Researchers found that managers caught 18 percent fewer errors in work they were told came from an AI employee, versus an AI tool.
“We’re all toddlers in this AI world,” says Julie Bedard, a BCG partner. People know what steps to take when a tool isn’t working or an employee is underperforming. When managing an AI employee, however, people still don’t know who should be held accountable.
“Everybody is very busy trying to figure all of this out,” she says, “and the pace of change is fast.”
What Makes a Good Coworker, Anyway?
One morning, a few days after I spoke with Franklin, Sophie Bot started pissing me off. My tweaks were failing to make it sound more like the real Sophie. If anything, the gap between the two was widening. After digesting Sophie’s tweet archive, Sophie Bot had begun to fumble basic AI functions. When I asked it to pull out
