Quick question: how many hours did you spend last week customizing applications?

I'm guessing too many. And I'm also guessing at least half of them still felt kinda generic because you were tired and just trying to get them submitted.

Here's what I want you to try instead.

You're gonna build yourself an AI agent that actually knows your story. Not a template that spits out corporate word soup. Something that helps you move faster and sound like yourself.

Most people are using AI wrong for this. They're asking it to "write a cover letter" from scratch every single time. That's exhausting and the output sounds like everyone else's ChatGPT cover letter.

What you want is a system you set up once, then use over and over.

Here's how:

First, create your master document. Write down your 3-5 biggest wins with actual numbers. What you're really good at—not how a job description would say it, how YOU'd say it. What kind of role you want. Maybe 2-3 companies you respect and why.

Then open Claude or ChatGPT or whatever you're using. Start a conversation just for job search stuff. First message: paste that whole master doc and tell it "This is my background. When I share job descriptions, help me customize my pitch."

Now train it on your voice. Grab 2-3 paragraphs you've actually written—emails, LinkedIn posts, anything—and paste them in. Say "This is how I sound. Match this."

Test it. Share a real job description. Ask for a customized pitch or cover letter. Read it back. Does it sound like you? If not, tell it what's wrong. It'll adjust.

You'll know it's working when applications take you 15 minutes instead of 2 hours, and when you read them you think "yeah, that's what I'd say."

You're not trying to trick anyone. You're trying to move faster without sounding like a robot. Big difference.

Try it this week. Let me know how it goes.

—Jacqueline

P.S. If this feels weird, remember: you're not asking AI to be you. You're asking it to help you communicate what you already know about yourself, faster. That's fair game.

Reply

Avatar

or to participate

Resilient Leader Insder Newsletter