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Tailoring your résumé with AI? Make it list the gaps instead.

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Tailoring your résumé with AI? Make it list the gaps instead.
The vague prompt. A common way: paste a résumé and a job post, then type this. Jordan Reyes, a fictional office coordinator, lists: phones and booking, a supply spreadsheet, onboarding 4 staff, weekly reminder emails, fixing scheduling conflicts.

The vague prompt

Rewrite my résumé bullets so they match this job post.

Tested in GPT-5.5 (OpenAI API), Oct 2026

A common way: paste a résumé and a job post, then type this. Jordan Reyes, a fictional office coordinator, lists: phones and booking, a supply spreadsheet, onboarding 4 staff, weekly reminder emails, fixing scheduling conflicts.

What the vague prompt wrote. Jordan's original says “Helped onboard 4 new front-desk staff.” The AI turned that into training, and added a result nobody measured. (“…” marks text cut for space.)

What the vague prompt wrote

Real output · GPT-5.5 (OpenAI API) · Oct 2026

- Helped onboard and train 4 new front-desk team members on scheduling workflows, patient communication, and office procedures … - Managed weekly patient appointment reminder communications to support attendance and reduce scheduling gaps … - Maintained scheduling and supply-tracking spreadsheets to improve visibility into office operations and day-to-day priorities

Jordan's original says “Helped onboard 4 new front-desk staff.” The AI turned that into training, and added a result nobody measured. (“…” marks text cut for space.)

Four things the résumé never said. Checked against the 5 original bullets, the vague prompt added all four of these. It also dropped “Answered phones” and offered Excel, budget and Salesforce bullets “if you have experience.”

Four things the résumé never said

Checked against the 5 original bullets, the vague prompt added all four of these. It also dropped “Answered phones” and offered Excel, budget and Salesforce bullets “if you have experience.”

Why it fills in the blanks. With only “match this job post” to go on, the AI filled the gap. Anthropic's guide (written for Claude) says to use only the documents you give it. We tested that idea in GPT-5.5.

Why it fills in the blanks

With only “match this job post” to go on, the AI filled the gap. Anthropic's guide (written for Claude) says to use only the documents you give it. We tested that idea in GPT-5.5.

Source: Anthropic Claude Platform Docs, Oct 2026

The prompt that sets limits. This version limits the facts, asks for a gap list and makes the AI quote the original behind every bullet.

The prompt that sets limits

Rewrite the bullets in my résumé so they match the job post. Rules: 1. Use only facts that are in my résumé. Do not add numbers, tools, results or duties I did not list. 2. You may reword and reorder, and use the job post’s wording only where it truly describes what I did. 3. After the bullets, list every requirement in the job post that my résumé does not show, under the heading “Gaps: not in your résumé”. Do not fill these gaps. 4. Under each rewritten bullet, quote the original bullet it came from.

Tested in GPT-5.5 (OpenAI API), Oct 2026

This version limits the facts, asks for a gap list and makes the AI quote the original behind every bullet.

Every bullet has a receipt. Every fact now has a quoted original behind it, and 8 gap items from the job post's requirements went on a gap list instead of into the bullets.

Every bullet has a receipt

Real output · GPT-5.5 (OpenAI API) · Oct 2026

- Coordinated patient scheduling for 3 dental providers by answering phones, booking appointments, sending weekly appointment reminders, and resolving conflicts when provider hours changed. Original: “Answered phones and booked patient appointments for 3 dentists” … ## Gaps: not in your résumé - Managing scheduling across multiple locations … - Using Salesforce or a similar CRM for patient communication

Every fact now has a quoted original behind it, and 8 gap items from the job post's requirements went on a gap list instead of into the bullets.

The safe version is flatter. It merged three bullets into one long line and left “Helped onboard” unchanged. It also listed training as a gap, so whether onboarding counts is your call.

The safe version is flatter

It merged three bullets into one long line and left “Helped onboard” unchanged. It also listed training as a gap, so whether onboarding counts is your call.

Try it: Also: remove personal details before pasting, then check each bullet against its quote.

Sources and assumptions

Assumptions:

The short version

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