Leveraging AI in your Job Hunt

As recently as December 2024, nearly 40% of job seekers have been looking for work for more than 15wks (source). For those of us who don’t have an uncle at the c-level, even knowing where to look for a job is very challenging. Add in the modern landscape of AI-augmented terrain, and it’s easy to feel overwhelmed. Hiring teams have been using some form of technology to help them screen candidates since the 90s, but with broad public adoption of AI models, and the arms race has begun in earnest. Job seekers now have the ability to fire off several, high-quality applications with the click of a few buttons. How do we handle this power tool at our disposal, and when (if ever) would it be better to use the reliable hand tool?


The New Workshop: AI Tools in Your Kit

A power tool exists to amplify your capabilities, but it requires skill and judgment to use effectively. Here's how to approach AI job-seeking from a craftsperson's mindset:

Resume Refinement

Don't: Blindly stuff your resume with AI-generated keywords

Do: Use AI to analyze job descriptions and identify core competencies that genuinely match your experience

Example Process:

  1. Feed the job description to an AI tool

  2. Ask for key themes and required skills

  3. Cross-reference with your actual experience, and if necessary, bolster your resume and cover letter with those skills.

Crafting Cover Letters

Don't: Generate generic cover letters

Do: Use AI to brainstorm structure and talking points, then craft your authentic narrative

Example Process:

  1. Feed your resume and job description into an AI tool

  2. Ask for a cover letter template and key matches between skills

  3. After drafting your own letter, run it through the AI tool again to analyze it’s match

Quality Control: Human-in-the-loop

If it’s honest, and comes from your own source materials, there’s no harm in using the time-saving benefit of AI. Even still, it’s best to keep one hand on the wheel before you click the submit button:

  1. Always verify AI suggestions against your actual experience

  2. Cross-reference AI insights with industry knowledge

  3. Maintain your authentic voice

  4. Test your materials with human readers


The Blueprint

Here's my tested approach for using AI in your job search:

Initial Research Phase

  • Input: Resume

  • AI Prompt: Attached is my resume. Highlight key skills and trends in my working experience. Ask me no less than 10 questions until you can suggest 10 matching job titles for someone of my ability.

  • Your Task: Answer the questions, start to search those job titles online

When you find a job

  • Input: job description

  • AI Prompt: Attached is the job description for a position I’d like to apply for. Please note the desired skills with those in my resume. Suggest areas of strong match, and areas with a weak match.

  • Your Task: Tweak your resume (if needed to better highlight skills) and draft a Cover letter based on results.

Interview Phase

  • Input: job description

  • AI Prompt: you are a world-class recruiter who won’t hire anyone unless you absolutely can’t say no to their outstanding interview. Use the attached job description to ask me five questions that would come up in my interview. After I’ve given my response, analyze my answers in terms of 1) how it matched the answer you were looking for, and 2) how polished my response was.

  • Your Task: Respond to the mock interview on-the-spot

Common Pitfalls to Avoid

Like any tool, AI can be misused. Watch out for:

  • Over-optimization that sounds robotic

  • Claiming skills you don't have

  • Losing your authentic voice

Work out the kinks in your process by mastering one AI tool at a time. I’ve found claude by Anthrop\c to be among the best in terms of user-friendliness, and love the ability to customize it’s response “voice".” When your confidence is up, try this out on some throwaway job descriptions. Adjust the output, save the best prompts, and keep whittling down the process until it matches you.

The Next Steps

Remember: A master craftsperson knows when to use power tools and when to reach for hand tools. Start by analyzing one of your recent job applications using AI tools. What insights emerge? What could be refined?

For a deeper dive into job searching, check out our ebook There’s No Perfect Job. It’s full of tips, processes, and templates to take you from aimless to authentic in your pursuit of meaningful career. Be sure to check out all of our ebooks at the Career-Craft store.