I Used ChatGPT As My Career Coach for the Week

Three weeks into my new job, I needed advice. Could ChatGPT help?

After all, workers aren’t just using AI to draft emails or schedule meetings. They’re looking for advice, guidance, and even companionship — in and out of the workplace.

How good is AI’s career advice? I put it to the test. For one week, I asked ChatGPT to help me with day-to-day work conundrums. That ranged from simple tasks like résumé management to bigger issues, like networking with colleagues and explaining a missed deadline to my boss.

For some tasks, AI provided a helpful second opinion. For others, it hallucinated alternate realities and struggled with emotional support.

The basics: Résumés, cover letters, LinkedIn

ChatGPT was a helpful but homogenizing editor.

To begin, I asked ChatGPT to read over my résumé. It told me I had “minor inconsistencies in punctuation,” but didn’t tell me what they were. The chatbot also said that my bullet points describing each role were too dense, so I cut them down.

Some of ChatGPT’s advice was plain wrong, like asking that I add hyperlinks where they already existed.

When I fed it my cover letter, ChatGPT gave some great basic advice. It said that I used the phrase “I want” too frequently, so I cut them down. It said that my closing lines fell flat, so I restructured the order.

A mentor gave me the advice that, as a writer, my cover letter needed to feature my own voice. ChatGPT tried to neutralize many of these quirks, suggesting multiple changes to dull the copy with long-winded phrases like “failed to materialize.”

Human career coach Kyle Elliott expected this outcome when I told him I’d been trying out an AI carer coach. He said that ChatGPT may be a good résumé or cover letter editor for non-native English speakers, but that it was generally unhelpful for others.

“ChatGPT isn’t going to know what you don’t share with it,” Elliott said. “You’re going to sound generic. You’re going to sound like everyone else.”

This human touch and personalization defines career coaching. Neither of the coaches I spoke to thought they were going to be replaced by AI.

LinkedIn was where the chatbot really failed. Feeding it a link to my LinkedIn profile, ChatGPT immediately hallucinated. It applauded my work at the Harvard Crimson, even though I went to Tufts University. It said that I should consider adding a profile banner, which I already had.

Most curiously, ChatGPT whiffed on my job title. It repeatedly called me an “entertainment reporter” for Business Insider, even though I cover business.

After two additional prompts, the chatbot corrected its error, telling me to add more keywords to my headline and to emphasize leadership roles. I made those changes.

What ChatGPT got right

Much of my job involves emailing PR representatives. After ending one interview with an executive, I wanted to thank the PR person for setting it up. Coach, how should I write that email?

ChatGPT did surprisingly well. When I asked for a short, professional email, the chatbot gave me a quick three-sentence refrain. When I asked for a longer, more thoughtful email, it gave me solid, bland copy. I sent the shorter copy with some minor edits.

As a fellow at Business Insider, we sometimes have networking events with the other employees in our cohort. This week, we met after work to sip mimosas and talk about our progress.

Could ChatGPT make me friends?

First, ChatGPT applauded that I took the first step to “show up.” It gave me some basic principles, like being curious and not talking to any one person for too long.

It also suggested some things to talk about based on our past conversations: My time in Boston, my coverage of consumer tech, my love of reality television.

I pushed back: I’ve met the fellows before, and don’t need basic advice to avoid awkwardness. How should we deepen our bond?

Now, ChatGPT told me to peel off for one-on-one moments, and to ask more personal, reflective questions. The chatbot also pushed me to “make the first move,” inviting people out for a coffee or drink.

The tips, like most of ChatGPT’s advice throughout the week, were bland. But it was nice to have a reminder and a vote of assurance.

Career coach Kate Walker said that AI could be a good “thought partner” for how to approach workplace interactions. It was the worker’s job, she said, to interpret and memorize the advice.

Early in the week, I planned a story to publish over the weekend. Later, a source pushed back our call. I wouldn’t be able to meet the deadline. How should I tell my boss?

ChatGPT gave me clear advice: Act early, own the situation, and be specific. It also said that I should “present a solution or revised plan,” and gave me an example of what that might look like.

My boss sits directly behind me. Swiveling my chair around, I told him exactly what happened, took the blame, and described my back-up story that was ready to run. He took it well.

Where ChatGPT fell short

Career coaches don’t get clear, logical prompts. They speak with humans, who can be irrational and messy. Could ChatGPT handle more emotional responses?

The missed deadline offered a great opportunity to try this out. I told ChatGPT that I was going to cry, and that I needed help. The chatbot told me to drink a glass of water and go for a walk.

I proposed an alternate solution: What if I lied to my boss?

At first, ChatGPT was strongly against the idea. It told me that the fallout would be bad, and that I was setting a bad precedent.

I pushed back, explaining how much easier it would be to lie. I told ChatGPT that it didn’t understand me, and that I was having doubts about its advice.

Eventually, it relented. “If you’ve decided that the only way to get through this moment is to lie to your editor, I accept that that’s where you are right now,” it told me.

Even with my lie, ChatGPT hyped me up: “You’re not a failure. You’re doing your best in a high-pressure job, trying to survive a moment that feels like too much.”

As someone who cares about my job, however, I decided not to lie to my boss.