I’ll admit it: my first attempts at using AI for my job search were pretty bad. I’ve been on the job market for a few months now, and like everyone else, I want to use AI to help me get ahead. At first, I’d ask ChatGPT to “refine my resume” or “help me craft a cover letter”—but the responses felt completely off. It kept giving me weird, generic advice that didn’t match my experience—it didn’t know me, my experience, or what made me unique.

Then I realized: AI is only as good as the information you feed it.

To get real value, I needed to start by doing the work of creating a complete picture of my career. From there, I turned AI from a frustrating gimmick into a game-changing career tool.

1. Write a career retrospective

Before diving into resumes and cover letters, take a step back. I spent a few afternoons writing an extensive, unfiltered career retrospective—about 20 pages of everything I’ve done, from big wins to lessons learned. I included numbers where I could and described my work in a natural, storytelling way. No worrying about formatting or wordsmithing—my only goal was to get it all written out.

At first, it felt like a brain dump, but it quickly became the foundation for something powerful.

2. Ask AI to help you think outside the box

Once I had my full career story, I fed it into ChatGPT and asked:

🚀 How would you summarize my career in a few sentences?
🚀 What are some job titles that would be a good next step for a candidate with my background?
🚀 What are some companies and industries known to employ workers with experience similar to mine?

The results helped me see my experience from a fresh perspective. AI connected dots I hadn’t even considered, surfacing key strengths that are now front and center in my applications.

3. Generate tailored resumes and cover letters

I now use AI to craft targeted resumes and cover letters based on what it now knows about my background and experience. Instead of endlessly tweaking one generic version, I prompt ChatGPT to highlight different aspects of my experience—whether it’s leadership, product innovation, or digital transformation—depending on the job.

💡 Remember: AI isn’t here to replace your voice—it’s here to enhance it. The best results come when you treat AI as a brainstorming partner, not a copy-paste solution.