Economics/Class Relations

Judging an AI career coach

October 28, 2023 • 5 min read
with Diamond Naga Siu
Happy weekend, buds. Sometimes, I think about how people who marry rich have found the ultimate cheat code. But TikTok star Dixie D’Amelio is being labeled out of touch for saying her “biggest goal professionally is probably to marry rich.”

In case it doesn’t work out, I tried using an AI assistant career coach — released as part of Meta’s new series of AI assistants — to see what advice it’d give. More on that in today’s big story.

What’s on deck
But first, is it even real?


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The big story
An AI career coach


Instead of AI taking away your job, what if it could help you find a new one?


That’s potentially the concept behind @levelupwithleo, an AI-powered career coach. He’s one of the dozens of new AI assistants that Facebook’s parent company Meta rolled out.


Many of them resemble celebrities like Naomi Osaka and Snoop Dogg, but Leo isn’t based on anyone famous.


I messaged him on Instagram about different career advice and then broke down what I liked and didn’t like about “him.”


Let’s start with the negatives:

  • It feels like a game. I tested Leo by asking a bunch of basic but specific questions: What’s the journalism job market like? What’s a good cover letter structure for a reporter? Who’s most at risk of being laid off at a digital media company? A lot of his answers were generic — and not advice I would likely follow or share with others. Instead of coming across as an expert, Leo felt like a conversational search engine with lukewarm search results.
  • Leo is very cautious. ChatGPT, Google’s Bard, and other AI chatbots received a lot of attention for giving inappropriate answers. Leo, on the other hand, would just skirt a lot of my questions. That was even the case for career-related questions on sensitive subjects like diversity and pay disparity.
  • It doesn’t have a memory of past conversations. Every time I asked a question, I needed to provide context that I might have previously shared. He remembered specifics from a few messages earlier, but not if the conversation happened a few hours ago.
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And now for the pros:
  • Solid résumé feedback. After some prodding, Leo offered helpful advice for making changes to my long untouched résumé. He suggested I describe the impact of my work, and also helped me decide where I could cut some past experiences for space.
  • Answers are fast. Most AI chatbots I’ve used (like Bing and ChatGPT) are fast but take a few moments to respond. But it felt like Leo responded even faster and with pretty long answers.
  • Occasionally strong insight. I was sometimes pleasantly surprised by Leo’s answers. For example, I asked for three logical next roles after being a senior newsletter reporter. He recommended a news editor, content strategist, or journalism professor. Leo was also able to describe how to transition to each role and provided a solid game plan for each one.
I wouldn’t seriously take or follow career advice from @levelupwithleo. But, interacting with a themed AI assistant gave me a peek of how they could be utilized at the future.
3 things in
1. Nissan is trying to make minivans cool again. The carmaker unveiled a flashy minivan concept that’s like a futuristic, rose-gold living room on wheels. The Hyper Tourer boasts swiveling seats, an LED screen on the floor, and mind-reading capabilities.


2. Photos show what it’s like to visit Alcatraz Island. The National Historic Landmark is famous for housing some of America’s most notorious criminals, including Al Capone. During its 29-year operation as a prison, 34 prisoners attempted to escape, and five were never found.


3. A celebrity stylist explains how to use colors while packing light for a trip. She suggested packing mostly neutrals and adding a few versatile pieces with a pop of color. Plus, she recommended considering location, environment, and personal style.

3 things in
dickcraft/Getty Images
1. The biggest career mistakes to avoid, according to a former VP of HR at Microsoft. Some top mistakes — among both employees and leaders — include asking for a raise and threatening to quit the company.


2. Raising the stakes of return-to-office isn’t the way to go. Major companies like Amazon and Meta are heavily enforcing their RTO mandates — they’ve threatened to fire or lower performance ratings for not going into the office. But employers could do better by focusing on keeping employees engaged instead.


3. The shock and upset of working a 9-to-5. A recent college graduate said she has little time for her personal life while working a full-time job. Many people said they could relate, and some are calling for reform to the 40-hour workweek.

3 things in
SOPA Images/Getty Images
1. Herds of wild javelinas keep ripping apart an Arizona golf course. The herbivorous beasts — also known as collared peccaries — have been on the prowl for food. And the assistant superintendent of the course has been documenting the weeks-long battle.


2. It’s getting spicy — ranking Trader Joe’s seasoning blends. The eight seasoning contenders were: everything but the elote, sriracha sprinkle, seasoning in a pickle, ranch, ketchup flavored sprinkle, Cuban style citrusy garlic, cheesy, and chile lime.


3. Walmart shoppers experience shame and embarrassment with self-checkout. The retail giant rolled out automated missed-scan detection technology to reduce theft. But customers say they’ve felt “treated like thieves” due to honest mistakes and technical glitches.


In other news


Joseph Hendrickson/Shutterstock
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Kitchen trends
RIP to these kitchen trends that interior designers say went out of style this year. They say trends like open floor plans and modern-farmhouse looks are becoming outdated.

News Quiz
Answers for the quiz from Friday’s edition
  • From Monday: This type of workout with a weighted backpack has become popular in Silicon Valley. Answer: Rucking
  • From Tuesday: Name the $3 billion edtech darling that threw lavish parties, struggled to vet tutors, and laid off hundreds of staffers. Answer: GoStudent
  • From Wednesday: An off-duty pilot is being accused of trying to shut off the engines of this airline’s plane mid-flight. Answer: Alaska Airlines
  • From Thursday: This infamous crypto founder plans to testify in his criminal trial. Answer: Sam Bankman-Fried
  • From Friday: This famous fast-food chain is scrapping an iconic spoon that’s a staple of one of its desserts. Answer: McDonald’s
Let me know how you did at

The Insider Today Saturday team

Diamond Naga Siu, senior reporter, in San Diego. Dan DeFrancesco, senior editor, in New York City. Hallam Bullock, editor, in London. Lisa Ryan, executive editor, in New York City.


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