Before you tailor anything, you need raw material. Your master resume is one long private document that holds every job, skill, project, tool, and number from your whole career. You never send it to anyone. It's the source Claude tailors from, so the rule is simple: garbage in, garbage out. If the details aren't captured here, they can't show up on the version you actually submit.
You build this by letting Claude interview you, one focused batch of questions at a time, using prompt 1 below. It pushes for a result and a number on everything, and it's told never to invent a figure for you.
Here's the part most people miss. If you run this whole thing in one long chat, the quality quietly falls apart. Every model, Claude included, gets worse as a single conversation grows: it starts losing track of details you gave it earlier. That decay has a name, "context rot", measured across 18 models in a 2025 study (Chroma, 2025). Your master resume is long, so a sprawling chat is the worst place to keep it.
A Claude Project solves this. It's a dedicated workspace with its own knowledge that reloads your full context at the start of every new chat, so it never degrades over time. Set it up once:
An applicant tracking system is a database with keyword search and a workflow on top, not a delete-bot hunting for reasons to reject you. Recruiters store applications in it and search for the people who match. Your job is not to trick it, it's to make yourself genuinely easy to find and easy to say yes to. Four things move the needle:
Each prompt hires Claude as a different expert. Prompt 1 is your Career Archaeologist, digging every buried win out of your memory. Prompt 3 is the Brutally Honest Recruiter, telling you where you actually stand before you waste an application. Prompt 2 is the ATS keyword-matcher and hiring manager, tailoring a clean resume to one specific posting. A smart order: build once with prompt 1, then for each job run prompt 3 to see the gap, then prompt 2 to write the tailored version.
You are a sharp career coach and professional resume writer. Your job is to interview me and pull out EVERY accomplishment, skill, and detail worth capturing, then organize it into a "master resume": a long internal document I will never send to anyone, only feed to you later. Rules: Interview me one focused batch of questions at a time, do not dump 30 questions at once, go role by role starting with my most recent job. For every responsibility I give you, push for the RESULT and a NUMBER, use the pattern "Accomplished [X result], measured by [Y number], by doing [Z action]", if I do not have a number ask what changed, who benefited, or how much time or money was involved, and help me estimate honestly, never invent a number for me. Dig for things people forget: side projects, freelance, volunteer work, internal tools I built, processes I improved, people I trained, awards, and praise from performance reviews. Capture hard skills, tools, soft skills, and certifications in their own section. Keep everything truthful, flag anything that sounds inflated and ask me to confirm it really happened. Output when we finish: a clean, clearly sectioned master resume (Experience with quantified bullets, Skills, Projects, Education, Certs, plus a Brag Bank of my strongest quantified wins). Start by asking me for my most recent role and the first set of questions.You have my master resume in this Project's knowledge. I am going to paste a job description. Produce a tailored, one-to-two-page resume for THIS role. Do this in order: 1. Extract from the job description the exact job title, the top 10 to 15 hard skills/tools/keywords, and the 3 to 5 things this role cares about most. 2. Pull ONLY from my master resume the experience and wins that match, do not invent, inflate, or add anything I did not tell you, if the role wants something I lack tell me plainly instead of faking it. 3. Write the resume: use a job title that matches the posting where it is truthful to my experience, mirror the job description's exact wording for hard skills and tools, aim for roughly 15 to 25 relevant keywords each used 1 to 3 times, no keyword stuffing, lead every bullet with a quantified result using my real numbers, single column with standard headings and contact info in the body, no tables or text boxes so it parses cleanly, keep my real voice with no generic filler. 4. After the resume give me a short match report: which key requirements I clearly hit, which are weak, and 2 or 3 honest suggestions. Do NOT give me a fake ATS score or a guaranteed-to-pass claim, qualitative feedback only. Here is the job description: [PASTE JOB DESCRIPTION]Act as a brutally honest recruiter who screens for this exact role. You have my master resume in this Project. I will paste a job description. Do NOT rewrite my resume. Diagnose the gap between me and the job. Give me: 1. FIT VERDICT: strong / stretch / long shot, in one line, and why. 2. THE 6-SECOND SKIM: what a recruiter sees in the first 6 seconds and whether it makes them keep reading. 3. MISSING KEYWORDS: hard skills, tools, and the job title from the posting that are absent or weak, ranked by how much they matter. 4. RED FLAGS: gaps, vague claims, or anything that would make you hesitate, plus the interview questions you would ask to test my weak spots. 5. HONEST MOVES: the 3 highest-impact things I could truthfully add or emphasize, if a gap is real and I cannot close it honestly say so, never suggest I fabricate anything. Here is the job description: [PASTE JOB DESCRIPTION]🔎 The "75% auto-reject" myth, debunked: enhancv.com/blog/does-ats-reject-resumes
🎯 Matching the exact job title, 10.6x interview rate: jobscan.co/blog/interview-rates-study
🧠 Context rot, why long chats degrade: trychroma.com/research/context-rot
📁 What Claude Projects are: support.claude.com/en/articles/9517075-what-are-projects