Ask It SimplyHi friend,
By the end of this email, you'll know how to turn your resume into one that fits a specific job, plus a short cover letter, in about ten minutes.
You know the feeling. You find a job you really want, then stare at a resume you haven't touched in years. Every posting asks for something a little different, and rewriting it each time takes an evening you don't have. So the same old resume goes out, again and again.
This is a job AI is genuinely good at. Give it your real resume and the job posting, and it rewrites your experience in the words that employer is using. You stay in charge of the facts. Here are three free tools to try, one for each step.
1. ChatGPT: the first draft
chatgpt.com
The free plan includes unlimited everyday text chats (within fair-use rules), so you can keep asking for changes until it reads right. You can also upload your resume file instead of pasting it. Uploads are limited on the free plan, but one resume and one job posting is a small ask.
Best for: turning your old resume and a job posting into a matched first draft.
2. Claude: getting the tone right
claude.ai
Claude has a Free plan you can use on the web, on your computer, or on your phone, with usage limits. Paste in the draft and ask it to sound like you: warm, confident, and not stiff. It's a good second opinion on a cover letter that feels too formal or too much.
Best for: making the cover letter sound like a real person wrote it. You.
3. Microsoft Copilot: the final polish
copilot.microsoft.com
The basic Copilot is free to use on the web and helps with writing. Since August, you need to sign in with a free Microsoft account to use it. If you own a Microsoft 365 Personal, Family, or Premium subscription, Copilot also lives inside Word, where you can select a line and ask it to rewrite it, adjust the tone, or make it more concise.
Best for: tightening wording right before you save the final file.
Try these prompts (copy and paste)
Prompt 1: the resume
Here is my current resume: [paste resume]. Here is the job posting: [paste posting]. Rewrite my resume for this job. Use only the jobs, dates, skills, and results that are already in my resume. Do not add any job, skill, degree, certificate, or number I did not give you. Use words from the posting where they truly match my experience. Keep it to one page. At the end, list any requirement in the posting that my resume does not show, so I can decide what to do about it.
Prompt 2: the cover letter
Using only the facts in the resume above, write a cover letter for this job in under [200] words. Open with why I want this role at [company name], give two real examples from my resume that match the posting, and end with a friendly ask for an interview. Sound [warm and confident], not stiff.
Fill in the brackets and paste them into any of the three tools. Want changes? Reply with "shorter," "less formal," or "lead with my customer service experience."
One mistake to avoid
Never send a line you can't back up. AI can "helpfully" invent a job title, a skill you don't have, or a number that sounds impressive. Read every single line out loud before you send it. If you couldn't explain it in an interview, delete it. Never invent jobs, skills, dates, or results. And before you paste anything in, leave out private details like your Social Security number or home address.
That's it for this week
Try it on one job you actually want this week. Then hit reply and tell me: what's the job you're going for? I'd love to cheer you on.
Talk soon, Dontè, Ask It Simply
P.S. Know someone job hunting right now? Forward this to them. They can join free at askitsimply.com.
Sources: ChatGPT plans and pricing · Claude plans and pricing · Microsoft Copilot terms of use (sign-in required, Aug 18, 2026) · Microsoft Copilot free vs. Copilot in Microsoft 365 · Draft and add content with Copilot in Word