Event Recap
February 7, 2026
ChatGPT Job Search Playbook
# ChatGPT Tips
# Future of Work
# Upskilling
ChatGPT Job Search Playbook
Chris Nicholson
This playbook is for job seekers who want to use ChatGPT as a practical assistant across their entire search, from picking target employers to closing interviews. You can use it to move faster while staying accurate, specific, and true to your voice. Each move includes what to do, prompts to copy, and quick checks so the output stays high-signal. It works especially well for career changers and busy candidates who need structure, better storytelling, and tighter alignment with job descriptions.
High-leverage setup
- Create one dedicated ChatGPT thread for your job search
- Keep everything in one place so context stays consistent
- Build a small input bundle once that includes
- Current resume
- 2 to 5 target job descriptions (copy-paste text, or keep links and paste the key sections)
- 2 writing samples that reflect your real voice (email, memo, LinkedIn post, anything you wrote)
- 8 to 12 work wins, projects, or proud moments (bullets are fine)
- Constraints and non-negotiables (location, pay needs, schedule, mission, manager style, travel, values)
- Set your ground rules up front
- “Preserve my voice based on these samples.”
- “Do not invent metrics, titles, tools, timelines, or scope.”
- “Flag anything that sounds generic, inflated, or unverifiable.”
- Use a simple working format for all outputs
- One version you can paste into a resume or cover letter
- One version with notes explaining why each change was made
- One list of clarifying questions when information is missing
Move 1: Direction and focus
- Outcome
- A one-pager describing your target roles to guide your applications
- What to do
- Ask ChatGPT to interview you before you apply widely
- Answer fast and honestly, then ask for patterns and a shortlist
- Prompts
- “Interview me about career motivators. Ask 20 questions, then summarize energizers, drainers, deal-breakers, and non-negotiables.”
- “Based on my answers, propose 6 to 8 role types that match. Include 3 role types to avoid and why.”
- “List likely bridge roles between what I do now and my target domain. Explain the overlap in skills and responsibilities.”
- Make it concrete
- Turn insights into a target profile with these fields
- Top 3 role types
- Top 2 industries
- Top 10 keywords to search
- 5 strengths you will lead with
- 5 non-negotiables written as rules
- Quality checks
- Non-negotiables written as testable statements
- Example: “No on-call rotation” or “Manager gives direct feedback weekly”
- Target list small enough to tailor applications without thrashing
Move 2: Role discovery and title translation
- Outcome
- A shortlist of job titles and keywords that match your transferable skills
- What to do
- Give ChatGPT your skills inventory plus a short description of what you actually did day to day in previous roles
- Ask for alternate titles, adjacent functions, and keyword variants
- Use the output to search job boards and LinkedIn more effectively
- Prompts
- “Given this skills inventory and experience summary, propose 12 job titles across industries. Include alternate titles and keyword variants recruiters use.”
- “For each title, list the top 8 keywords to search and the top 5 keywords to avoid because they pull irrelevant roles.”
- “Map my experience to the top 10 responsibilities in these job descriptions. Produce a skills translation table with evidence from my background.”
- Make it concrete
- Pick 2 role types to pursue first
- Save the keywords as a reusable search string
- Keep a list of titles that are synonyms so you stop missing roles due to label mismatch
- Quality checks
- Every suggested title backed by evidence from your wins list
- Bridge roles included when the domain shift is large
Move 3: Resume and cover letter that survive a first skim
- Outcome
- One tailored resume version per role type, plus a reusable cover letter skeleton
- What to do
- Treat your resume like a fast-scanning artifact
- Tailor by selecting and reordering bullets for each role type
- Rewrite bullets to show impact and judgment, not task lists
- Keep language clear for recruiters and still credible for hiring managers
- Prompts
- “Act as a recruiter with just 30 seconds. Here is the job description and my resume. List knockout risks, missing signals, and the top five fixes.”
- “Rewrite these bullets for clarity and impact. Keep facts unchanged. Keep voice consistent with this writing sample.”
- “Replace generic phrasing with specifics: scope, constraints, decisions, outcomes. Ask questions where details are missing.”
- How to implement the edits
- For each bullet, force these fields into the rewrite
- What problem you solved
- What you did that mattered (decision, trade-off, approach)
- What changed (result, measurable impact, cost, time, quality, risk)
- Keep a “spare bullets” list
- Extra bullets you swap in when a job description changes
- Quality checks
- First third of the resume matches the job description’s priorities
- Every bullet answers “so what” in one line
- Voice sounds like you, not generic template text
- Technical detail readable by non-specialists while staying accurate
Move 4: Interview prep that compounds
- Outcome
- A story bank you can draw on, plus practiced delivery to build confidence
- What to do
- Brain-dump raw stories from your wins list
- Convert each into STAR format (situation, task, action, result)
- Practice out loud using voice conversations
- Stress-test with follow-up questions and tighter versions
- Prompts
- “Turn this raw story into STAR. Ask clarifying questions first. Produce a concise version and a longer version.”
- “Create a story bank of 8 STAR stories that cover leadership, conflict, ambiguity, failure, speed, collaboration, judgment, and learning.”
- “Run a mock recruiter screen for this role. Ask follow-ups. Score me on clarity, concision, and evidence of impact. Then rewrite my best answers.”
- How to practice with voice mode with ChatGPT as mock interviewer
- Ask for a real interview cadence
- One question at a time
- Follow-ups when you ramble or skip results
- Ask for feedback on delivery
- Too fast, too long, missing stakes, missing results
- Quality checks
- Story starts with stakes and context in 1 to 2 sentences
- Actions include decisions and trade-offs
- Results are measurable where possible, or clearly observable
Move 5: Projects and portfolios with a compelling why
- Outcome
- Project narratives that convert into resume bullets and interview answers
- What to do
- Lead with the problem and why it mattered
- Highlight constraints, trade-offs, and impact
- Prepare a crisp “project proud of” answer tied to the role
- Prompts
- “Draft a portfolio summary for this project. Lead with the problem and why. Include constraints, trade-offs, impact, and what changed because of it.”
- “Generate interview talking points for this project that map directly to this job description.”
- Quality checks
- Motivation and problem clarity stronger than feature lists
- Project demonstrates judgment, initiative, and learning
Move 6: Active networking toward ideal roles
- Outcome
- Warm outreach that leads to conversations and credible referrals
- What to do
- Start with people who have seen your work directly
- Past managers, peers, cross-functional partners
- Draft relationship-first messages with specific context
- Use coffee chats to learn about hiring signals and reality of roles and process
- Prompts
- “Create a network map from this list. Prioritize people who have seen my work and are closest to these target roles.”
- “Draft outreach messages that reference shared context and a low-pressure ask for advice, not a referral.”
- “Write 10 coffee-chat questions that reveal interview focus areas, team expectations, and what stands out in candidates.”
- Quality checks
- Outreach avoids transactional referral requests
- Each message includes a specific reason you reached out to that person
Any time: Confidence & resilience support from ChatGPT
- Practical uses
- Pep talk before interviews
- Naming your feelings and identifying what feels risky
- Rehearsing recovery lines for curveballs
- Prompts
- “Give a short pep talk grounded in what I prepared and the evidence in these stories.”
- “Simulate three curveball questions for this role and coach calm recovery lines.”
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