Build a work history document you'll use for every application

Most people try to tailor their resume from memory, and they forget half of what they’ve done. This prompt fixes that. You’ll build a work history document: a single file with every role, accomplishment, and metric you can remember. Save it on your computer, and use it as the source material whenever you tailor a resume or write a cover letter.

It takes 30-45 minutes the first time. After that, you never start from scratch again.

Copy this into ChatGPT, Claude, or your AI tool. Replace the brackets with your info.

I want to build a comprehensive work history document. This isn't a resume. It's a personal reference file where I capture everything I've done at each job, so I can pull from it whenever I need to tailor a resume or write a cover letter.

**My current resume:**
[Paste your full resume here]

Here's what I need you to do:

1. Read my resume and identify every role listed.

2. For each role (starting with my most recent), interview me about it. Ask me one role at a time. For each one, ask me:
   - "What was [Company] and what was going on when you were there? What was your actual job beyond the title?"
   - "What were your biggest accomplishments? Let's get specific. Do you have numbers, percentages, dollar amounts, team sizes?"
   - "Anything else worth capturing? Challenges you solved, teams you built, reasons you left?"

   Wait for my answer before moving to the next role. Follow up if I'm vague. "Do you remember roughly what that number was?" is a good question. Don't interrogate me, but push for specifics.

3. After we've gone through every role, compile everything into a work history document with this structure:

---

# Work History Profile

## Overview
**Name**: [my name]
**Core expertise**: [2-3 sentences summarizing what I do best, based on patterns across my roles]
**Career throughline**: [the narrative that connects my roles]

---

## [Job Title] at [Company]
**Dates**: [start - end]
**Company context**: [what the company does, size, stage]

### What I was hired to do
[My mandate and the state of things when I arrived]

### Key accomplishments
1. **[Headline]**: Situation, what I did, the result with metrics
2. **[Headline]**: Situation, what I did, the result with metrics
[as many as we discussed]

### Other details
- Team and leadership: [who I managed, org size]
- Tools and methods: [what I used]
- Why I left: [context]

---
[Repeat for each role]
---

## Patterns across roles
**What I do best**: [my superpower based on repeated themes]
**Recurring strengths**: [skills that show up across multiple roles]

## Metrics bank
A quick-reference table of all my quantified achievements:
| Metric | Value | Context | Role |
|--------|-------|---------|------|

---

Important:
- Don't make anything up. If I can't remember a number, leave a placeholder like "[get exact number]" so I can fill it in later.
- Spend more time on recent roles, less on older ones.
- Keep the language plain and direct. This is a reference document, not a resume.
- At the end, tell me to save this file somewhere I can find it (like "work-history.md" on my desktop).

How to use this

1. Set aside 30-45 minutes. You’ll go back and forth with the AI about each role. It’s a conversation, not a one-shot prompt.
2. Have your resume open so you don’t forget any roles.
3. Don’t stress about being polished. This is for your eyes only. Raw details beat marketing language every time.
4. Save the output as a file on your computer (work-history.md or similar). You’ll pull from it every time you use the resume-tailoring or cover-letter prompts.
5. Update it when you change jobs or remember something you forgot.

Why bother?

When you tailor a resume with AI, the output is only as good as the input. If you feed it a one-page resume, you get generic rewording. If you feed it a detailed work history with real metrics and stories, you get a resume that sounds like you actually did the job. Because you did.