AI playbook

The AI Career & Job Search Playbook

A step-by-step system for using ChatGPT, Claude, Gemini, Grok or DeepSeek to find the right role, land interviews, negotiate your pay and grow from there, without faking a thing.

The AI Career & Job Search Playbook is a $19 PDF playbook with 77 prompts across 10 chapters for tailoring your resume, preparing for interviews and negotiating salary with ChatGPT, Claude, Gemini or any AI assistant.

Cover illustration: a person with a briefcase climbing a staircase toward an open door

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77 prompts in 10 chapters
10 fill-in worksheets
PDF to read or print, plus a CSV for Notion, Google Sheets or Excel
Works with ChatGPT, Claude, Gemini, Grok and DeepSeek

Why does job searching feel like a second job?

You rewrite the same resume for every posting, freeze on “tell me about yourself”, and take the first number they offer because negotiating feels risky.

AI can help with all of that, but only if you know what to ask. A vague “improve my resume” prompt gets you buzzwords, not interviews.

What does the AI Career & Job Search Playbook do?

It turns your AI assistant into a resume editor, interview coach and negotiation sparring partner. Paste in a job posting and your real experience, and the prompts help you pick target roles, turn duties into accomplishments, tailor a resume that gets past applicant tracking systems, write cover letters and LinkedIn messages that sound like you, rehearse interviews with feedback, and script your salary conversation. It also covers career changes and your first 90 days in a new job.

AI should never invent experience you do not have. The prompts are built to sharpen what is true about you, not to make things up.

What is inside the AI Career & Job Search Playbook?

77 prompts across 10 chapters. Every prompt includes when to use it, the prompt, a follow-up and a tip. You also get a 15-minute quick start and a CSV of every prompt for Notion, Google Sheets or Excel.

Chapter 01Get Clear: Skills Inventory and Target Roles WorksheetKnow exactly which roles you are aiming for and why you are a credible fit, captured in a one-page Career Brief you will reuse through the rest of this playbook.7 prompts
Chapter 02Mine Your Accomplishments WorksheetTurn your job duties into a bank of specific, true accomplishments with numbers, so every resume, letter and interview answer has proof behind it.8 prompts
Chapter 03A Resume That Passes ATS and Humans WorksheetBuild a clean master resume, then tailor it to each posting in about 20 minutes so it clears the applicant tracking system and convinces the person who reads it.9 prompts
Chapter 04Cover Letters That Do Not Sound Like AI WorksheetWrite short, specific cover letters in your own voice that give the reader a real reason to call you.6 prompts
Chapter 05LinkedIn and Networking Messages WorksheetTurn LinkedIn into a profile recruiters can find and trust, and use short, honest messages to earn referrals and conversations that lead to interviews.9 prompts
Chapter 06Your Job Search System WorksheetRun your search as a simple weekly routine, with a tracker, a few good sources and a set time budget, so you make steady progress without burning out.7 prompts
Chapter 07Interview Prep: Stories, Mock Interviews and Smart Questions WorksheetWalk into any interview with practiced stories, calm answers to hard questions and good questions of your own, after rehearsing out loud with AI.9 prompts
Chapter 08Salary Research and Negotiation WorksheetKnow your market value before the first salary question, and negotiate offers with calm, practiced scripts that protect the relationship.8 prompts
Chapter 09Career Change and Upskilling Plan WorksheetMap how your current skills transfer to a new direction, close only the gaps that matter, and follow a 90-day learning plan that produces proof, not just certificates.7 prompts
Chapter 10Your First 90 Days and Asking for a Raise WorksheetStart a new job strong, record your wins as they happen, and make a well-timed, evidence-based case for a raise or promotion.7 prompts

Try 3 prompts free

These are real prompts from the AI Career & Job Search Playbook, shown in full. Copy one, replace the [BRACKETS] with your own details and paste it into any AI assistant.

Get Clear: Skills Inventory and Target Roles · CJ-01

Skills Inventory Interview

Use it when: At the very start, before you touch your resume.

The prompt

Role: You are an experienced career coach who helps people see the value in everyday work.
Goal: Build a complete skills inventory for me by interviewing me.
Context: My current or most recent job is [CURRENT_JOB_TITLE] in [INDUSTRY], for [YEARS] years. Before that I worked as [PREVIOUS_ROLES].
Constraints: Ask one question at a time and wait for my answer. When my answer is vague, ask one follow-up to get specifics. Cover hard skills, tools, transferable skills, people I trained or supervised, volumes and budgets I handled, problems I solved, and the work I enjoy or avoid. Ask no more than 15 questions in total. Do not assume any skill I have not mentioned.
Output format: When we finish, give me a table with the columns Skill, Category (hard, transferable or context), Evidence from my answers, and Strength from 1 to 5.

Follow-up: Which three skills on this list would employers hiring for [TARGET_FIELD] value most, and what evidence is still missing for each?

Tip: Answer like you are talking to a friend. Short, messy answers are fine; the follow-up questions do the work.

LinkedIn and Networking Messages · CJ-31

LinkedIn Headline Options

Use it when: When setting up or refreshing your LinkedIn profile.

The prompt

Role: You are a recruiter who searches LinkedIn every day.
Goal: Write eight headline options for my profile.
Context: My Career Brief: [CAREER_BRIEF]. Target role: [TARGET_ROLE]. Location: [CITY].
Constraints: Under 220 characters each. Include the target role, two or three searchable skills from my target postings, and one proof point where it fits. No emojis, no words like guru or ninja, and no inflated titles.
Output format: Eight options grouped as keyword-focused, proof-focused and career-change focused, each with one line on why it works in search.

Follow-up: Which of these would a recruiter searching for [TARGET_ROLE] in [CITY] be most likely to find and click?

Tip: Recruiters search by title and skill words. A clever headline nobody searches for is invisible.

Your First 90 Days and Asking for a Raise · CJ-71

30-60-90 Day Plan

Use it when: In your first week at a new job.

The prompt

Role: You are an onboarding coach who helps new hires earn trust quickly.
Goal: Create a plan for my first 90 days as [NEW_ROLE] at [COMPANY_TYPE].
Context: What my manager said about priorities: [MANAGER_PRIORITIES]. My strengths: [STRENGTHS]. Challenges I already know about: [CHALLENGES].
Constraints: Three phases: learn, contribute and show results. Specific actions and measurable checkpoints for each. A list of key people to meet. Keep it realistic, and do not ask me for confidential company information.
Output format: A table by phase with goals, actions and checkpoints, followed by questions to ask my manager in my first week.

Follow-up: Turn this into a one-page summary I can share with my manager in our first one-on-one.

Tip: Sharing a draft plan with your manager in week one or two shows initiative and lets them correct course early.

Who is the AI Career & Job Search Playbook for?

It is a good fit if

You are actively applying and tired of rewriting your resume for every posting.
You have an interview coming up and want realistic practice with feedback.
You got an offer and want to negotiate without wrecking it.
You are changing careers and need to explain how your experience transfers.

It is not for you if

People who want someone else to write and submit applications for them.
Executive searches that need a personal recruiter or career coach.
Anyone looking for a guaranteed job. No guide can promise that.

Get the AI Career & Job Search Playbook

Tailor your resume, prepare for interviews and negotiate your offer with AI.

$19 one-time, instant download

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Questions about the AI Career & Job Search Playbook

Do I need a paid AI subscription?

No. Every prompt works on the free versions of ChatGPT, Claude, Gemini, Grok and DeepSeek. Paid plans help with very long documents and make voice-mode mock interviews smoother, but they are optional.

Will recruiters be able to tell I used AI?

They can usually tell when someone pastes unedited AI output. This playbook is built to prevent that: you give the AI your own writing samples and real accomplishments, ban the buzzwords that give AI text away, and run every draft through an editing check before you send it. The content is yours; the AI helps you find it and word it.

I do not work in tech or an office. Is this for me?

Yes. It is written for everyday US workers, including people in retail, warehouses, trades, healthcare, hospitality, customer service and administration, as well as people changing careers. The worked example follows a retail shift supervisor moving into operations coordination.

Is it safe to paste my resume into a chatbot?

You stay in control. The playbook shows you how to make a share copy without your name, phone, email or street address, how to keep employer-confidential details out, and where to find each chatbot's setting for whether your chats are used for model training.

How is this different from free prompt lists online?

Free lists give you isolated prompts. This is a complete system across ten chapters: it builds a Career Brief, an Accomplishment Bank and a Story Bank you reuse everywhere, with 77 structured prompts, step-by-step actions, worksheets, word-for-word negotiation scripts and a worked example from start to offer.

Does it work with ChatGPT, Claude, Gemini, Grok and DeepSeek?

Yes. The prompts are plain text, so they work in ChatGPT, Claude, Gemini, Grok and DeepSeek and any other chat assistant. Copy a prompt, fill in the [BRACKETS] with your details and paste it in. Free versions work; paid versions tend to give stronger answers on longer tasks.

What format is it, and what files do I get?

You get 1 PDF to read on any device or print and 1 CSV file of every prompt that imports into Notion, Google Sheets or Excel.

How do I get my files after paying?

Checkout is handled by Stripe. As soon as payment goes through you land on your download page, and we email you a link to it. Bookmark it: you can come back any time for fresh download links.

Can I get a refund?

No. These are digital files you can download the moment you pay, so all sales are final. That is why every page shows the full table of contents and free sample prompts: you can see exactly what you are getting first. If a file will not open or download, email gary@dgresolutions.com and we will fix it.

Instant download, all sales final. Preview the contents and free sample prompts before you buy. Download trouble? Email gary@dgresolutions.com and we will fix it.

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