Writing this from the airport, running on very little sleep, and still recovering from last night’s Boston Admin Awards Gala! A few of us ended up camped out in front of the venue until about midnight because we didn’t want the night to end. It was a FAB evening and SO great to meet a lot of you in real life!!

Anyway! Confession time: I used to tell people to throw their resume into ChatGPT and say "tailor it to this job." Turns out that's the career equivalent of asking a stranger to pack your suitcase. You'll get a suitcase. It just won't have your stuff in it. Consider this my formal retraction.

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"Tailor my resume" is a vague instruction, and vague instructions get vague results. The chatbot rewrites everything, sands off the specifics that made you interesting, and occasionally invents a skill you've never touched. You end up sounding like every other AI-polished resume in the pile, and you get IGNORED!

I’m certainly not suggesting you don’t use AI, but you’re telling it to do the wrong thing. Here's the better one, in three steps:

You cannot tailor your way out of a bad resume. If the foundation is weak, AI is just rearranging furniture in a house with no walls.

What you need is a base resume: a strong, complete, honest version of your experience that acts as a living, breathing document. This is your master copy. You don't send it anywhere. You duplicate it for every role you apply to, then make quick, targeted edits to the copy.

A good base resume has specific accomplishments (not job duties), real numbers where you have them, and clean formatting an ATS can actually read. If yours was last updated during a different presidential administration (ahhhh simpler times), it's time.

Now, the natural plug (cough cough): if you want a base resume built properly, that's literally what I do. But if you're not sure whether you even need one, just reply to this email with your resume attached. I'll tell you honestly. If yours is solid, amazing, go forth and apply. If it needs work, I'm happy to help, or at the very least I'll send you a few quick tips you can fix yourself. No pitch-slapping. Promise!

I wrote a whole issue on this recently (read it here), but here's the short version.

Recruiters pass a handful of candidates to the hiring manager each day. By day three, everyone involved is quietly hoping and praying the winner is already in that first batch so they can keep it moving. And in this market? They usually are.

The perfect resume submitted on day five is competing for a seat that's already been filled. Speed is a strategy. Set job alerts, check them daily, and apply early. FIRST 24 HOURS!

This is where the magic happens. Instead of asking AI to rewrite your resume, you ask it to diagnose your resume. Where would the ATS rank you lower? What's missing? What's there but described in words the system won't recognize?

Once you know your gaps, you fix only those. Surgically. Your resume stays yours, and it now checks the boxes the ATS is scoring you on.

Open ChatGPT or Claude, upload your resume, and paste this in:

That last line matters. You want a diagnosis, not a makeover.

Now look at your gaps. For each one, ask yourself: have I done this thing, or the closest possible version of it?

Most of the time, the answer is yes. You just never wrote it down, or you wrote it down in your words instead of theirs. The job description says "stakeholder management" and your resume says "kept everyone on the same page." Same skill. The ATS doesn't know that.

So brain dump it. Messy is fine. Then paste this prompt into the same chat:

Pick the bullet that sounds most like you, drop it into your tailored copy, and repeat for your top gaps. Three to five targeted bullets will do more for your ATS ranking than a full AI rewrite ever will.

And please, read every bullet before it goes on your resume. If you can't talk about it confidently in an interview, it doesn't belong there.

"Tailor my resume" asks AI to guess. A Gap Audit tells it exactly where to aim. Stop asking the wrong question, and the right roles start answering.

P.S. Not sure if your base resume is up to the job? Hit reply and attach it. I'll give you an honest answer either way.

Stuck in your job search? Not sure how to handle a tricky interview question or navigate the hiring process? Submit your question anonymously, and I’ll answer it in an upcoming newsletter.

Was any of this helpful?! Hit reply and let me know :)