AI did NOT help me get the job 🥲

I went through two rounds of interviews for a freelance writer role a few weeks ago. The first interview was a screener, while the second was the more substantive interview with the people I’d work with.

To prep for the interviews, I did my research as usual—but I also decided to try getting AI’s help since I recently signed up for a paid Claude plan.

After my AI-assisted prep, both interviews went well. I didn’t have trouble with the questions, and the interviewers also said they liked my work. So, I thought I had a good chance of getting the job and was going to write a whole newsletter about how I used AI in my interview prep.

I had it all thought out. My email newsletter’s subject line: “AI helped me get the job”. I couldn’t wait.

The only problem was that…I ended up not getting the job. LOL. The reason: they preferred to hire someone more junior who had a lower rate.

I was disappointed for sure, but I wasn’t too surprised, because they’d expressed concerns about my rate during the first-round interview. All in all, it’s fine—there are plenty more opportunities to chase.

And even though the outcome wasn’t what I wanted, I thought I’d share how I used AI for my interview prep anyway. 😂

“Help me to prepare.”

To be honest, I didn’t use any verbose AI prompts. I just entered this into Claude:

“I’m preparing for an interview call for this job position at [company name]: [job description link]. Help me to prepare.”

Claude reviewed the job description page, and then gave me the following (your AI assistant’s response may vary):

• A background of the company and the role: E.g. the company’s size, the product they wanted to promote in their content, the role’s deliverables
• The company’s possible interview aims: E.g. finding out my understanding of their customers and my ability to work independently. Claude inferred these aims from the job description’s wording.
• Likely interview questions and how I could answer them
• Questions to ask them: This is a good one, because asking the interviewers questions shows you’re interested in the job
• My relevant background to highlight: Claude has some knowledge of my background due to my past chats with it, and it referenced relevant points that could help sell me
• A checklist of things I should prepare before the interview: Action steps for me, like checking out the client’s existing content and competitors

From there, I used Claude’s input to fill in the gaps in my own research.

I did something similar for the second-round interview. After I found out who the interviewers would be, I gave Claude their names, job roles and LinkedIn profiles. And I ended my prompt in a similar way: “Help me prepare.”

Claude returned:

• Both interviewers’ backgrounds and possible role in the interview: E.g. one of them might assess my technical abilities while the other assesses my understanding of their customers
• Likely interview questions and how I could answer them
• Questions to ask both interviewers: Claude tailored these questions to match the interviewers’ backgrounds

Claude’s input was helpful for both interviews—especially its flagging of likely interview questions. Because some of them did come up!

So, from this experience, I’ll likely use AI for future interview prep, but I won’t completely outsource my prep to it.

I’ll continue doing my own research about the client, and prepping answers to possible interview questions, before getting AI’s input on whether there are angles or questions I haven’t thought of.

I find that going through the research process myself helps me learn and remember things better than just reading someone else’s (e.g. AI’s) research.

AI should be a thinking partner, not a thinking replacer.

More freelancer news

Goodman Arts Centre to defer its rental hike

Goodman Arts Centre previously informed its project studio tenants (who are mainly self-employed artists and art groups) that it was increasing its short-term rental rates by 60% starting from around July 2026.

But in view of ongoing economic uncertainty due to the Iran war, the rental increase will be deferred until the end of the year at the minimum.

​More details here.​