I Let AI Interview Me to Rewrite My Resume

I've been job hunting for about two months now. If you've read my earlier posts, you'll know it hasn't been smooth. The rejections have been consistent, the feedback generic, and the pattern frustratingly clear: my experience isn't the problem - my resume is.

That's a hard thing to admit when you've spent weeks refining it. But the evidence was difficult to ignore. Roles I was genuinely qualified for were filtering me out before a human ever read a word. And when I did get through to a screening call, the outcome was the same polite, non-specific rejection that tells you nothing useful.

So I tried something different. I sat down with Claude - Anthropic's AI assistant - and asked it to help me rewrite my resume. What I didn't expect was how the process would unfold.

The resume I started with

My original resume was pretty good. It listed my roles, my titles, my skills. It had bullet points that described what I did at each company. It was accurate - but it was completely failing to land.

The problem, I think, is that I wrote it the way most of us write resumes: as a factual record. Here's where I worked, here's what my title was, here's a sanitised summary of my responsibilities. It read like a job description, not a story. And in a market where your CV has about six seconds to make an impression - assuming it gets past the ATS at all - "accurate but unremarkable" is a death sentence.

The interview

I expected Claude to take my resume, sprinkle some stronger verbs on it, and hand it back. Instead, it started asking questions. A lot of questions.

Not surface-level ones either. It wanted to know what was actually broken when I joined Company X. How bad was the codebase? What did the team look like? What specific changes did I make, and what happened as a result? It asked about team sizes, revenue figures, client numbers, reporting lines. It pushed on the gap between my job titles and what I was actually doing. It asked about people I'd mentored, performance reviews I'd conducted, difficult conversations I'd had to have.

It was, honestly, closer to a good interview than a writing exercise.

And that's where things got interesting. Because when you're forced to articulate the full story - not just "stabilised delivery" but "inherited a failing rebuild with two departing developers, recruited a new team, introduced structured communication, and regained executive confidence to the point where the CEO stopped attending our update meetings" - you realise how much you've been underselling yourself.

I found myself explaining how I rearchitected a marketing platform from hard-coded campaign types that took months to deliver into a config-driven system that cut that to two to four weeks. How I walked into a startup with no CTO, no engineering process, and an agency-built codebase, and built the entire function from scratch. How I ended up as the sole technical and product lead across two products worth two million dollars in combined annual revenue, after successive restructures stripped away every other support role around me.

None of that was on my original resume. Not really. The facts were there in outline, but the impact was buried under vague, cautious language.

What came out the other side

Claude produced two separate resumes - one aimed at engineering manager roles, the other at senior technical lead positions. Same career history, but framed very differently.

The engineering manager version leads with a leadership capabilities section that front-loads hiring, performance management, mentoring, and delivery practices before getting into the role history. It's designed to get past the keyword filters that have been screening me out, while telling a coherent story about someone who's been doing engineering management for years under titles that didn't reflect the scope.

The technical lead version leads with the tech stack and puts the architectural decisions, system rescues, and hands-on engineering front and centre. It reads as a strong individual contributor who leads from the front.

Both are significantly longer and more detailed than what I started with. But every bullet point has a concrete claim behind it - a number, a before-and-after, a specific outcome. That's the difference between a resume that describes responsibilities and one that demonstrates impact.

What I actually learned

The exercise surfaced a few things I hadn't fully reckoned with.

First, I'd been protecting companies that no longer need protecting. I was writing carefully neutral descriptions of situations that were, frankly, messy. Stalled rebuilds, overpromised clients, departing teams, repeated restructures. The instinct is to smooth all of that over. But the mess is the story. Walking into chaos and creating order is the most valuable thing on my resume, and I was barely mentioning it.

Second, I'd been assuming that the reader would infer impact from context. They won't. If you grew a client base to 750 agencies across three markets, you need to say that. If you cut feature delivery time from months to weeks, you need to say that. The reader isn't going to do the maths for you.

Third - and this is the one that connects back to my earlier post about the title trap - I'd been letting my job titles frame the narrative instead of framing it myself. Claude pushed me to describe what I actually did, not what the contract said. That shift in framing changed everything about how the experience reads.

A note on using AI for this

I want to be straightforward about something: I didn't ask Claude to fabricate anything. Every claim in both resumes is true and I could back it up in an interview. What Claude did was act as an interviewer - pulling out details I wouldn't have thought to include, asking follow-up questions that forced me to be specific, and then structuring the result in a way that's optimised for how resumes are actually read in 2026.

I should also be clear: I didn't take what Claude produced and submit it unchanged. The output was a strong draft, but it was still a draft. I read through both versions carefully, adjusted phrasing that didn't sound like me, toned down anything that felt overstated, and made sure the final document was something I'd be comfortable defending line by line. AI is a useful collaborator for this kind of work, but your resume represents you - not your tools. Final editorial control matters.

Could I have done this myself? Probably, eventually. But there's something about being interviewed - even by an AI - that bypasses the instinct to be modest. When someone asks you directly "what was broken and what did you fix?", you answer honestly. When you're writing about yourself, you hedge.

I don't know yet whether these new resumes will change my results. I'll find out soon enough. But for the first time in two months, I feel like my CV actually represents what I've done - not just where I've been.

If you're in a similar position - experienced but struggling to land interviews - I'd genuinely recommend trying this approach. Not because AI is magic, but because the interview format forces you to say out loud what you've been too careful to write down. And sometimes that's all it takes.