How to Level Up Your Job Hunt With AI
Using AI to find, evaluate, and apply for jobs.
I’ve recently been invited to do a guest talk on using AI for job hunting.
That’s when it struck me: In the entire two years of writing this newsletter, I’ve never touched upon this use case.
Yet there are many areas of job search where AI can help.
To many of us, the first thing that immediately springs to mind is, “I’ll just get ChatGPT to write my CV and cover letter for me. Boom! #lifehack”
And, well, yes.
That’s certainly one way to use AI.
But—much like my advice in “The Skeptical Writer's Guide to AI”—you’ll get more value by staying in the driver’s seat rather than outsourcing everything to AI.
AI is best seen as a sparring partner that helps you through all stages of the job hunt.
Here are the ones I’ll cover:
Self-discovery: What are you good at and what are your values?
Upskilling: What gaps exist in your skillset and how can you close them?
Job search: What existing jobs fit your profile and expectations?
Company research: What can you learn about a specific company before applying?
Application process: How do you tailor your CV and cover letter to the job?
Job interview prep: How do you prepare and practice for job interviews?
Feedback analysis: What insights can you gain from any feedback from potential employers?
Decision and negotiation: How do you evaluate job offers and negotiate the best terms?
Now let’s look at each phase in detail and see how AI can help.
Note: I share some “starter prompts” for each step, but they’re mostly there for inspiration. Go ahead and expand them or modify them for your needs. (I’ve been pretty vocal about my stance on copy-pasting off-the-shelf prompts without review.) And remember: You can instantly improve almost any prompt with the “Ask me questions” line.
👀 1. Self-discovery
I know. This sounds like some vague guru mumbo-jumbo.
But before your job hunt even begins, you’ll probably want to take a step back and figure out what you’re after:
What are your professional strengths and weaknesses?
What are your interests and aspirations?
What do you value in a potential employer?
And so on.
The goal is to figure out what career path or type of job best fits your skills and personality.
How AI can help
Any chatbot used in combination with the “Ask me questions” method could make a great sparring partner, helping you with stuff like:
Asking probing questions about your skills, values, etc.
Analyzing your responses to extract insights you might’ve overlooked
Suggesting career paths based on what it learns about you
Relevant AI tools
Most LLMs will work well for this step, but you’ll get the most out of those built especially with empathy and conversations in mind. Some ideas:
ChatGPT with Advanced Voice Mode: If you prefer talking instead of typing, Advanced Voice Mode is the best there currently is. Even as a free user, you get 15 minutes per month to try it. (Here’s how you can get the most out of those 15 minutes.)
Pi: Inflection’s Pi is perhaps the friendliest, most empathetic chatbot out there. That’s exactly what you’ll need at this stage. As a bonus, Pi comes pre-equipped with a decent voice mode, so you can have a regular voice chat with it about yourself.
Starter prompt
"I’m looking to discover my ideal career path. Ask me questions about my skills, interests, values, and goals. Then suggest potential job options that align with my answers."
👨🎓 2. Upskilling
Now that you know what you’re looking for, you might find out there’s a gap between your skills and what your dream job requires.
In this step, you’ll want to uncover these gaps and create a learning plan:
What are the specific skills this kind of role calls for?
How does your current background align with these?
What courses and learning opportunities are out there?
The goal is to move from simply identifying skill gaps to actionable learning opportunities.
How AI can help
You can turn AI into your personal mentor and development coach, getting it to help with:
Comparing your current skills to job requirements to identify knowledge gaps
Finding relevant courses and educational resources
Creating a structured learning plan
Testing your knowledge and giving you feedback
Relevant AI tools
You'll want tools that can find relevant study materials and help you practice. Some options:
Claude: Claude’s great at extracting fresh insights from documents, and its “Artifacts” feature can turn learning materials you upload into a visual and interactive course with quizzes, etc. (See how to do that here.)
NotebookLM: Perfect for turning long info sources into tailored study materials. Its ability to handle almost any input format is great: Throw a video lecture or a PDF of a research paper at it, and it’ll have no issues.
Perplexity: This AI-powered search engine is great for vague, complex queries (e.g. “What courses are best suited for a junior programmer who wants to learn how to lead a team of developers?”)
Starter prompt
“Based on my current background [insert insights from #1], what additional skills will I need for a job as a [job role]. Please suggest some specific learning courses and create a study plan."
🔍 3. Job search
At this point, you know what you’re after and you’ve brushed up on those critical job skills.
Look at you, so productive!
Now comes the part where you actually look for jobs that fit your requirements:
How’s the job landscape looking?
What open positions match your criteria and competencies from steps #1 and #2?
Ideally, you’ll find the perfect match between your experience and available jobs.
How AI can help
AI is great at translating broad queries into searches for specific jobs. It can help you:
Turn broad queries into concrete job titles
Browse for job openings that match your criteria
Spot any emerging trends or patterns in the job market
Relevant AI tools
For this task, you’ll want AI with Internet access, like:
ChatGPT with web browsing.
Perplexity, for the same reasons as point #2.
Starter prompt
"Help me find current job listings that match my profile [key insights from step #1]. Focus especially on roles that require [skills from step #2]. Explain why each job might be a good fit."
🏢 4. Company research
Once you’ve made a shortlist of jobs, it’s time for a closer look at your potential employers. You’ll want to know what makes them tick before you work on your application:
What do current employees say about working there?
What projects and challenges is the company tackling?
How is the business going overall?
Hopefully, you’ll find a few golden nuggets of info to help you make an informed decision and make your application stand out.
How AI can help
Think of AI as your research assistant who actually enjoys reading annual reports.
It can:
Parse and summarize any amount of publicly available info about the company
Spot patterns in employee reviews
Find curious details to mention in your cover letter
Relevant AI tools
It’s best to look for large language models that can handle a lot of context.
NotebookLM, for largely the same reasons as point #2. You can feed it details about a company in almost any format (docs, video, audio, etc.). Gemini’s 2-million-token context window ensures it can absorb lots of info without losing key facts.
Perplexity is great for additional information search to supplement NotebookLM, which doesn’t have direct Internet access.
Starter prompt
"I am applying for [job position from #3]. Please research [company], review [attached files] and provide a summary of its culture, recent achievements, employee satisfaction, and any other insights relevant for crafting an effective application.”
📝 5. Application process
This is it!
It’s time to update your CV and put together that fancy cover letter.
Thanks to everything you’ve done so far, you should have all the building blocks you need.