Prompts to Tailor Your Resume to a Job Description
Tailoring is mostly deciding what to move up, what to cut, and which of your words to swap for the posting's words. These prompts take 2 inputs — your current resume and the full posting — and return a reordering plan with reasons, rather than a rewritten document you have to trust line by line. Where the posting asks for something you have never done, the output says so plainly. That gap list is the useful half: it tells you whether to apply at all, and what to address in the cover letter.
Before you paste any of these
Paste the whole posting, boilerplate included — Requirements and context often sit in the "about the team" paragraph rather than the bullet list. Trimming the posting down to its requirements removes the detail that tells the model which of your projects is closest to the work.
Ask for a diff, not a document — Request a list of changes — "move the Kafka bullet from role 3 to role 1", "cut the volunteer section" — so you can apply them one at a time. A returned full resume hides which lines it quietly rewrote along the way.
Cap it at 8 edits — Tell the model you will make at most 8 changes and ask it to rank them. Unlimited tailoring turns every application into a rewrite, and the applications you never send cost you more than an imperfect one.
Keep the gap list between applications — Save the requirements you do not meet in a separate note. After 2 or 3 postings the same missing skill repeats, and that pattern is a better guide to what to learn next than any course catalog.
7 prompts to copy
Every prompt ends with the same rules: use only what you give it, and mark a missing number with a placeholder instead of guessing one.
Before you decide whether a posting is worth applying to, or what your cover letter has to account for
What to have ready
•the full text of the job posting
•your current resume, pasted as Markdown or plain text
You are reviewing my resume against one job posting. Do not rewrite anything yet.
JOB POSTING:
[PASTE THE FULL POSTING]
MY RESUME:
[PASTE YOUR RESUME]
Return 3 Markdown lists:
1. Evidenced — every requirement in the posting my resume already supports, each with the exact line that supports it.
2. Underweighted — requirements my resume supports but buries, with where that evidence currently sits.
3. Not evidenced — requirements nothing in my resume supports.
For list 3, name the gap plainly and stop there. Do not draft bullets to cover those items, do not suggest wording for experience I have not described, and do not soften a gap into a partial match.
Finish with one sentence per gap: is it something a cover letter can address, or is it a hard requirement I do not meet.
Rules — these override everything above:
- Use only the experience I give you. Do not invent employers, job titles, dates, degrees, certifications, skills, or metrics.
- If a number would strengthen a line and I have not given you one, write a placeholder like [X%] or [$X] for me to fill in. Do not estimate it.
- Do not add a tool, skill, or credential I did not list, however standard it is in my field.
- Rewrite, reorder, tighten and re-emphasize what is already there. Where I have given you too little to work with, ask me for it or leave [add detail].
Send this next
Take list 2 only. For each item, quote my line and tell me which section and which position it should move to.
Gemini: Gemini may follow a job posting link and answer from the live page instead of the text you pasted — check that the requirements it lists back match what you sent.
Open inCopies the prompt, then opens the assistant
When your resume already holds the right evidence but the best of it sits on the second page
What to have ready
•the job posting
•your full resume with every bullet in its current order
Act as an editor with one instruction: reorder, do not rewrite.
POSTING:
[PASTE THE POSTING]
RESUME:
[PASTE THE FULL RESUME]
Return my resume in Markdown with:
- Sections in the order that serves this posting, and one line under each heading explaining why it sits there.
- Bullets within each role reordered so the most relevant to this posting comes first.
- Every bullet kept word for word. If a bullet would read better worded differently, list it under a separate heading called Rewrite candidates, keeping every fact in it unchanged — do not edit it in place.
- A closing list called Cut candidates: bullets that do nothing for this posting.
Do not add bullets, roles, tools, or skills. If the posting asks for something my resume does not cover, list it under Not evidenced and leave it there.
Rules — these override everything above:
- Use only the experience I give you. Do not invent employers, job titles, dates, degrees, certifications, skills, or metrics.
- If a number would strengthen a line and I have not given you one, write a placeholder like [X%] or [$X] for me to fill in. Do not estimate it.
- Do not add a tool, skill, or credential I did not list, however standard it is in my field.
- Rewrite, reorder, tighten and re-emphasize what is already there. Where I have given you too little to work with, ask me for it or leave [add detail].
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Now show me the first 12 lines a reader would see, and tell me what impression they give before anything else is read.
Claude: Claude's context window holds a long posting and a full resume in one message, which matters here — the ordering is only right if it read every bullet.
Open inCopies the prompt, then opens the assistant
When the same summary is going to every posting and it reads like it belongs to nobody in particular
What to have ready
•the job posting
•your current professional summary
•the 3 to 5 bullets from your resume you would defend in an interview
Write 3 versions of a professional summary for this application, using only the material below.
POSTING:
[PASTE THE POSTING]
MY CURRENT SUMMARY:
[PASTE IT]
MY STRONGEST BULLETS:
[PASTE 3 TO 5]
Each version: 2 to 3 sentences of Markdown, no heading of its own, and never opening with "I am a".
- Version A leads with years and domain.
- Version B leads with the accomplishment closest to what the posting asks for.
- Version C leads with the problem this team appears to have in the posting's own words, then the line of mine that speaks to it.
After each version, put the source line it came from in parentheses so I can check it. Where a number would sharpen a sentence and I have not given you one, write [X] and ask me for it at the end. Then tell me which version you would send, and what it gives up.
Rules — these override everything above:
- Use only the experience I give you. Do not invent employers, job titles, dates, degrees, certifications, skills, or metrics.
- If a number would strengthen a line and I have not given you one, write a placeholder like [X%] or [$X] for me to fill in. Do not estimate it.
- Do not add a tool, skill, or credential I did not list, however standard it is in my field.
- Rewrite, reorder, tighten and re-emphasize what is already there. Where I have given you too little to work with, ask me for it or leave [add detail].
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Give me the same 3 versions cut to a single sentence each, for the top of a one-page resume.
Open inCopies the prompt, then opens the assistant
When you and the posting are describing the same work in two different vocabularies
What to have ready
•the job posting
•the bullets from your resume that describe the relevant work
The posting below and my bullets below describe overlapping work in different words. Build the mapping before anything is rewritten.
POSTING:
[PASTE THE POSTING]
MY BULLETS:
[PASTE THEM]
Return a Markdown table with 3 columns: the posting's term, my current wording, and whether they name the same thing (Yes / Partly / No).
Then for the Yes rows only, rewrite my bullet in the posting's term — same facts, same scope, same scale, nothing new. Show old and new side by side so I can compare.
For Partly rows, explain the difference in one line and let me decide.
Any term in the posting with no row at all goes under a heading called No matching work. Leave those alone. Do not stretch a bullet to reach a term, and do not add a term to my skills section because the posting uses it.
Rules — these override everything above:
- Use only the experience I give you. Do not invent employers, job titles, dates, degrees, certifications, skills, or metrics.
- If a number would strengthen a line and I have not given you one, write a placeholder like [X%] or [$X] for me to fill in. Do not estimate it.
- Do not add a tool, skill, or credential I did not list, however standard it is in my field.
- Rewrite, reorder, tighten and re-emphasize what is already there. Where I have given you too little to work with, ask me for it or leave [add detail].
Send this next
For the No matching work list, tell me which terms are core to the role and which are nice-to-have boilerplate.
Open inCopies the prompt, then opens the assistant
When tailoring has pushed your resume onto an extra page and something has to leave
What to have ready
•the job posting
•your full resume
•the page count you are aiming for
I need this resume down to [1 OR 2] pages for the posting below. Help me choose what goes.
POSTING:
[PASTE THE POSTING]
RESUME:
[PASTE THE FULL RESUME]
Score every bullet and every section from 1 to 5 on relevance to this posting alone, and show the score beside each line in a Markdown list.
Then propose cuts in this order: all 1s, then 2s, then any 3 that repeats a point already made elsewhere.
Rules:
- Never cut employment dates, employer names, or an entire role. A missing role reads as a gap.
- Flag any cut that would remove the only evidence for something the posting asks for, and recommend keeping it.
- Do not merge two bullets into one claim that neither of them supports on its own.
Finish with the trimmed resume in Markdown and a plain list of everything you removed.
Rules — these override everything above:
- Use only the experience I give you. Do not invent employers, job titles, dates, degrees, certifications, skills, or metrics.
- If a number would strengthen a line and I have not given you one, write a placeholder like [X%] or [$X] for me to fill in. Do not estimate it.
- Do not add a tool, skill, or credential I did not list, however standard it is in my field.
- Rewrite, reorder, tighten and re-emphasize what is already there. Where I have given you too little to work with, ask me for it or leave [add detail].
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Save the cut list as a separate Markdown block I can keep for other applications, grouped by role.
Open inCopies the prompt, then opens the assistant
When you are applying to another team at your current employer and the reader already knows part of your work
What to have ready
•the internal posting
•your current resume
•notes on projects at this company the hiring manager may already know about
I am applying for a move to another team at my current employer. The reader knows the company, may know some of my work, and does not need the context an outside reader would.
INTERNAL POSTING:
[PASTE IT]
MY RESUME:
[PASTE IT]
WHAT THIS AUDIENCE ALREADY KNOWS:
[PASTE YOUR NOTES]
Return a Markdown resume adjusted for this reader:
- Keep internal system, product, and team names where they carry meaning here, and expand any acronym only my current team uses.
- Move cross-team work, and anything touching the hiring team's area, to the top of the relevant role.
- Cut the company-explaining context an external reader would need.
Then, separately: list what the posting asks for that my material does not evidence. For each one, ask me whether it is something I have done here and never wrote down. Ask the question — do not answer it for me.
Rules — these override everything above:
- Use only the experience I give you. Do not invent employers, job titles, dates, degrees, certifications, skills, or metrics.
- If a number would strengthen a line and I have not given you one, write a placeholder like [X%] or [$X] for me to fill in. Do not estimate it.
- Do not add a tool, skill, or credential I did not list, however standard it is in my field.
- Rewrite, reorder, tighten and re-emphasize what is already there. Where I have given you too little to work with, ask me for it or leave [add detail].
Send this next
Turn the unanswered items into 5 short questions I can bring to a coffee chat with the hiring manager.
Open inCopies the prompt, then opens the assistant
When your most recent job is not the one that matches the posting
What to have ready
•the job posting
•each role you are weighing, with its title, dates, and your existing bullets
More than one of my roles could carry this resume, and I want the ordering argued rather than guessed.
POSTING:
[PASTE THE POSTING]
ROLE 1: [TITLE, DATES, BULLETS]
ROLE 2: [TITLE, DATES, BULLETS]
ROLE 3: [TITLE, DATES, BULLETS]
For each role give me: its relevance to this posting in 2 lines, the single strongest bullet for this reader, and the strongest objection a hiring manager would raise about leading with it.
Then recommend one of 3 structures — strict reverse chronological, a relevant-experience section above the rest, or grouped by theme — and say what your choice costs me.
Keep every date visible in whatever structure you propose; hidden dates read as concealment. If your case for the lead role depends on something I did not give you, name what is missing instead of assuming it.
Rules — these override everything above:
- Use only the experience I give you. Do not invent employers, job titles, dates, degrees, certifications, skills, or metrics.
- If a number would strengthen a line and I have not given you one, write a placeholder like [X%] or [$X] for me to fill in. Do not estimate it.
- Do not add a tool, skill, or credential I did not list, however standard it is in my field.
- Rewrite, reorder, tighten and re-emphasize what is already there. Where I have given you too little to work with, ask me for it or leave [add detail].
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Write the section heading and the 2-line framing paragraph for the structure you recommended, in Markdown.
Open inCopies the prompt, then opens the assistant
More prompts that also cover tailor your resume to a job description
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