AI versus AI: 60 Job Search Prompts

Start your 2025 job hunt with help from the robots.

January 09, 2025

Hi BoTs,

I use AI a lot - to refine emails, break tasks down, plan my day, and like a search engine across the web. I usually use ChatGBT as my default AI assistant, but my friend told me recently she only uses Claude and that it’s “so much better.” I was planning on doing a blog post on how to use ChatGBT to job hunt, but then I decided to make it better with a little AI versus AI action: ChatGBT versus Claude. I declared a winner at the bottom. Read on for 60 job search you can use in your AI assistant of choice, and the one I think is the clear winner for this prompt.

THE PROMPT: “please write 30 specific prompts divided by stages of a job search on how to use AI to get a job. be as detailed as possible”

ChatGBT’s response (no editing by me or follow-up questions for clarification):

Here’s a list of 30 detailed AI-powered prompts divided by stages of a job search:

Stage 1: Self-Assessment and Goal Setting

  1. "What are some potential career paths for someone with [skills, degree, and experience]?"

    1. Provide a list of your skills, degrees, and experiences for AI to suggest relevant career paths.

  2. "Based on my strengths in [list strengths], weaknesses in [list weaknesses], and interests in [fields], what jobs should I consider?"

  3. "How do I evaluate whether my skills in [specific area] are competitive for roles in [industry]?"

  4. "What are the top in-demand skills in [industry or job role] in [current year]?"

  5. "Create a plan for transitioning from [current role/industry] to [desired role/industry] over [timeframe]."

Stage 2: Resume and Portfolio Creation

  1. "Can you write a resume tailored for [specific role] based on these details: [list of your experiences, skills, and accomplishments]?"

  2. "Generate strong bullet points for my resume using this input: [describe a specific role and responsibilities you held]."

  3. "What keywords should I include in my resume to pass applicant tracking systems for [job title]?"

  4. "Create a compelling LinkedIn summary for someone pursuing a career in [field]."

  5. "Analyze this portfolio content: [paste portfolio or project details]. How can I make it more appealing for [specific audience or job role]?"

Stage 3: Job Search Strategy

  1. "List 10 companies that are leaders in [industry] and likely to hire for [specific role]."

  2. "How can I find job openings that aren’t posted online for [specific role or industry]?"

  3. "Suggest networking strategies to connect with professionals in [field] on LinkedIn or at industry events."

  4. "What are the most effective job boards for finding [type of role] in [location or industry]?"

  5. "How do I optimize LinkedIn’s job search filters to find opportunities for [specific role]?"

Stage 4: Application Writing

  1. "Write a tailored cover letter for this job description: [paste job description] and my background: [list relevant experience and skills]."

  2. "Suggest ways to personalize my application for a job at [specific company] based on their mission and culture."

  3. "How do I address gaps in employment in my cover letter?"

  4. "What is the best format to present my freelance/contract work in applications for full-time roles?"

  5. "Draft a professional follow-up email for a job application at [company name] submitted [X days] ago."

Stage 5: Interview Preparation

  1. "Generate a list of common interview questions for [specific role] in [industry]."

  2. "What are the best ways to answer behavioral questions like 'Tell me about a time you handled a challenging situation'?"

  3. "How can I explain my career shift from [industry/role] to [new industry/role] in interviews?"

  4. "Help me practice for an interview. Simulate the role of an interviewer for [specific position]."

  5. "What questions should I ask at the end of an interview for [specific job]?"

Stage 6: Offer Negotiation

  1. "How do I research and benchmark salaries for [specific role] in [location] to prepare for negotiation?"

  2. "Write an email asking for time to review a job offer while remaining professional and enthusiastic."

  3. "Draft a counteroffer email that asks for [specific salary or benefit adjustment] based on my qualifications and market trends."

  4. "How do I evaluate multiple job offers and compare them based on compensation, growth, and company culture?"

  5. "Provide strategies to professionally decline an offer from [specific company] while keeping the door open for future opportunities."

Claude’s response (no editing by me or follow-up questions for clarification):

# AI-Powered Job Search Guide: Strategic Prompts by Stage

## Stage 1: Self-Assessment & Career Direction

1. "Analyze my attached resume and work history. What are the top 5 transferable skills I've demonstrated across roles? For each skill, provide specific examples from my experience that showcase this capability."

2. "Based on my current skill set [list skills], what emerging or adjacent career paths should I consider? Please analyze market demand, required upskilling, and potential salary ranges for each suggestion."

3. "Review my attached LinkedIn profile and compare it to 3-4 job descriptions I'm interested in. Identify any significant gaps in my experience or skills, and create a detailed action plan to address each gap."

4. "Help me identify my unique value proposition as a professional. Analyze my experience in [industry/role] and create a compelling narrative that differentiates me from other candidates."

5. "Based on my career goals [specify goals] and current market conditions, what specific industries or companies are experiencing growth and would be a good fit for my background? Please provide detailed reasoning."

## Stage 2: Resume & Application Materials Optimization

6. "Review my resume for [specific role]. Rewrite each bullet point using the STAR method (Situation, Task, Action, Result) and incorporate relevant keywords from this job description [paste description]."

7. "Create a master list of achievement metrics from my work history that I can use across different versions of my resume. Format each achievement using 'Accomplished [X] as measured by [Y], by doing [Z]'."

8. "Analyze this job description [paste description] and create a keyword frequency list. Then, help me naturally incorporate the most important keywords into my resume while maintaining readability."

9. "Generate 5 different versions of my professional summary, optimized for different types of roles I'm targeting [list roles]. Each summary should be ATS-friendly and highlight relevant transferable skills."

10. "Review my cover letter for [company name and role]. Rewrite it to better align with the company's stated values and culture [paste company values], while maintaining a professional yet personable tone."

## Stage 3: Job Search Strategy & Research

11. "Research these 3 companies [list companies] and create detailed comparison matrices of their culture, values, recent news, growth trajectory, and potential red flags. Include specific questions I should ask during interviews."

12. "Based on my target role [specify role], generate a list of 20 companies that match these criteria: [industry, size, location, culture]. Include reasoning for each suggestion and potential networking connections."

13. "Analyze current market conditions and salary data for [specific role] in [location]. Create a negotiation strategy document including target salary range, benefits to prioritize, and specific talking points."

14. "Help me create a targeted networking strategy. Analyze my LinkedIn connections and identify 10 key professionals who could provide introductions or insights into [target companies/industry]."

15. "Generate a weekly job search schedule template, including daily tasks, time blocks for different activities, and metrics to track progress. Include specific action items for both active and passive job searching."

## Stage 4: Interview Preparation

16. "Based on this job description [paste description], generate 30 potential interview questions, categorized by type (behavioral, technical, cultural fit). Include suggested STAR-format responses based on my experience."

17. "Review my answer to 'Tell me about yourself' for a [specific role]. Rewrite it as a compelling 2-minute narrative that highlights relevant experience and naturally transitions to why I'm interested in this role."

18. "Create a comprehensive preparation guide for a technical interview in [specific field], including key concepts to review, practice problems, and common pitfalls to avoid. Base this on my current skill level [specify level]."

19. "Help me prepare questions to ask my interviewers at [company name]. Generate role-specific questions, company-specific questions, and questions tailored to each interviewer's background [paste LinkedIn profiles]."

20. "Analyze my previous interview performance [describe feedback] and create a targeted improvement plan. Include specific strategies for handling nervous behaviors and techniques for stronger responses."

## Stage 5: Networking & Personal Branding

21. "Review my LinkedIn profile and optimize it for [target role]. Generate suggestions for headline, about section, and experience descriptions that incorporate relevant keywords while maintaining an authentic voice."

22. "Create 10 engaging LinkedIn post ideas related to my industry [specify industry], showcasing my expertise and thought leadership. Include suggested hashtags and ideal posting times."

23. "Help me craft a networking message template for cold outreach on LinkedIn, specifically for connecting with [target audience]. Include 3 variations and follow-up message templates."

24. "Generate a content calendar for professional social media presence, including topics, formats, and scheduling for LinkedIn, Twitter, and industry-specific platforms. Focus on establishing expertise in [specific areas]."

25. "Review my personal website/portfolio and suggest improvements for better personal branding. Include specific content suggestions, layout improvements, and ways to better showcase projects."

## Stage 6: Offer Evaluation & Negotiation

26. "Compare these two job offers [paste details]. Create a comprehensive analysis including total compensation, growth potential, company stability, and work-life balance. Generate specific questions to clarify any ambiguous points."

27. "Help me prepare a salary negotiation script for [specific offer]. Include multiple counter-offer scenarios, specific talking points about my value proposition, and professional ways to address potential pushback."

28. "Analyze this benefits package [paste details] and identify areas for negotiation beyond salary. Create a prioritized list of requests and suggested language for discussing each item."

29. "Generate a decision matrix for evaluating this job offer against my current role. Include both quantitative factors (compensation, benefits) and qualitative factors (culture, growth, work-life balance)."

30. "Help me craft a professional acceptance/rejection letter for [company name] that maintains positive relationships and leaves the door open for future opportunities. Include specific appreciation points and key discussion items from the interview process."

## Tips for Using These Prompts Effectively:

- Customize each prompt with your specific details, experience, and target role/industry

- Provide as much context as possible to get more tailored responses

- Use the outputs as starting points and customize them to maintain authenticity

- Always verify AI-generated information with official sources, especially for market data and company information

- Save and organize AI-generated content for future reference and iteration

- Regularly update your prompts based on feedback and results from your job search

OVERALL WINNER: CLAUDE

My friend was right. I think the prompts Claude came up with are better, and I like that it showed you in-prompt how to make the answer more tailored for you. It also referenced STAR, decision matrixes, and ATS (applicant tracking systems), showing a more detailed understanding of what I was asking IMO.

You can sign up for Claude for free here: https://claude.ai/

And ChatGBT for free here: https://chatgpt.com/

Pretty cool time to be alive. Now go get that new job!

-Molly Beck