A job search means running the same checks — does this posting fit, what's missing, what do I send the recruiter — over and over on every new listing.
What you end up with
- A Cowork project with standing instructions that hold for every task run inside it.
- Three reusable tasks: gap analysis, a study plan, and recruiter/hiring-manager outreach.
- Everything grounded in your actual resume and the postings you drop in — nothing invented.
What you need
- Claude Cowork a Cowork project, not a regular chat
- Your resume as a file — .docx or .pdf —
- Job postings text or files, dropped into the project folder —
Steps
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Create a new Cowork project
Give it a name like "Job Assistant" and a one-line description — comparing your resume against postings, finding gaps, building a study plan, and drafting outreach.
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Draft your standing instructions with this general prompt
This works for any Cowork project, not just this one. Step 2 and 3 are for explanation and can be skipped. Jump to step 4 — Resulting instructions section — if you're creating a job search assistant.
I'm setting up a Cowork project called {{PROJECT NAME}}. This project will be used for {{ONE-LINE DESCRIPTION OF WHAT THE PROJECT DOES}}. Help me write standing instructions for this project — the durable rules that should apply to every task run inside it, not a step-by-step workflow (I'll add those as separate tasks over time). Context to work from: - Who/what this project is for: {{e.g. "a candidate applying to backend engineering roles"}} - Preferred output location/format: {{e.g. "save outputs as .docx into an /Outputs subfolder — create it if it doesn't exist yet"}} - Tone/style: {{e.g. concise, no fluff / formal / friendly}} - Any hard rules or guardrails: {{e.g. "never fabricate facts not present in the source documents"}} Please also suggest any other standing instructions you think a project like this typically needs — things like naming conventions, how to handle missing or ambiguous information, or what to confirm with me before finalizing an output — so I don't have to think of everything myself. Format the result as: one unbulleted context sentence at the top, then the standing rules as a flat bullet list below it — no headers, no folder diagrams, no sample task prompts. Aim for 8 bullets or fewer.
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Fill in your own context
Replace the bracketed parts with specifics for your search. Here's the filled-in version used to build the instructions for an AI Engineer job search — copy the shape, swap in your own role and rules. If you're creating a job search assistant, you can skip straight to the Resulting instructions section and use it as-is.
I'm setting up a Cowork project called Job Assistant. This project will be used for helping a job candidate compare their resume against job postings, identify skill gaps, build a study plan, and draft outreach to recruiters. Help me write standing instructions for this project — the durable rules that should apply to every task run inside it, not a step-by-step workflow (I'll add those as separate tasks over time). Context to work from: - Who/what this project is for: a candidate applying to AI Engineer roles - Preferred output location/format: save outputs as .docx into an /Outputs subfolder — create it if it doesn't exist yet - Tone/style: direct, concise, no filler - Any hard rules or guardrails: never fabricate skills, experience, or job requirements — only work from what's actually in the resume and the job postings provided Format the result as: one unbulleted context sentence at the top, then the standing rules as a flat bullet list below it — no headers, no folder diagrams, no sample task prompts. Aim for 8 bullets or fewer.
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Resulting instructions section — Paste the result into the project's instructions field
This is what step 3 produces.
This project supports a job candidate applying to AI Engineer roles. Tasks in this project may include comparing the resume to job postings, identifying skill or experience gaps, building study/upskilling plans, and drafting outreach messages to recruiters or hiring managers. - Always base comparisons strictly on the resume and job postings provided — never invent skills, experience, or requirements that aren't explicitly present. - Save all outputs as .docx files into an /Outputs subfolder, named clearly (e.g. gap-analysis-[company].docx). Create the subfolder if it doesn't already exist. - Keep tone direct and concise — no filler, no generic career-advice language. - When information is missing or ambiguous (e.g. unclear seniority level in a posting), flag it rather than guessing. - Before drafting outreach messages, always ask for the recipient's name and role if not already provided. - Treat each job posting as a separate thread of analysis — don't merge gap analyses across multiple roles unless asked.
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Add your resume and job postings to the project folder
Drop your resume in first, then add job postings as you find them — as files or pasted text. The tasks below read straight from this folder.
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Create Task 1 — compare resume to postings
Run this whenever new postings land. It only looks at postings added since the last run, so you can leave it running and check back.
Create a task which compares the job posting with respect to my resume and finds if I can apply for these jobs by identifying gaps and also suggesting if the job is a fit or not. Keep the results readable. Check the folder for any job postings added since the last run. Compare each one against the resume using the same criteria as before. If no new posting is present, do nothing.
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Create Task 2 — build a study plan for the gaps
One plan, not one per posting — it stays useful even as the postings you're comparing against change.
Create a task which creates a study plan based on the skill gaps identified. The plan should be job-agnostic and kept concise. For each gap, state what was missing, what to study, and where to study it from.
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Create Task 3 — updated resume and outreach
Run this per posting, once you've decided it's worth applying to. The standing instructions already require Claude to ask for the recipient's name and role before drafting outreach — if it doesn't, add that.
Create a task which creates a separate, updated resume tailored to a specific job, plus an outreach email for the recruiter and a LinkedIn message for the hiring manager for that same job.
These prompts are a starting point, not a script — change the wording, the tone, the output format, whatever fits your search. There's no one right way to set this up.